44: Jared Weinstein - Within Earshot, Out of Camera Shot

Speaker A: If people were to look at your resume, they would infer that you are like a cold-blooded killer, basically. Speaker B: I got to the White House in July of '02. So, I mean, you get there, there's no kind of playing around. I mean, the stakes are high. But I think when the stakes are high and those leaders showed up with, we trust you to do the job we've hired you to do, I think I aspire for high-stakes environments that are psychologically safe too. So on May 1st, 2006, at like 7:04 AM, I remember my phone, it rings and it says Oval Office, Karen Keller, who was the President's Secretary.

And she said, hey, can you come down here. And so I walk 30 feet down to the Oval Office and I pop in and say, hey Karen, what do you need? She said, I don't need you, he does. He said, Blake's going off to business school, what do you think about riding shotgun with me for the rest of administration? And I said, let's do it. I had an incredibly rich experience. My desk was, you know, 10 feet from the Oval Office. So I'm not sure I wanted to go be a junior lobbyist in town.

I went to what is called analytics at Harvard, and I think there was 4 or 5 section and you're assigned to a section and you have an assigned seat. And I get to the section and I turn to the guy next to me and I said, hey, I'm Jared Weinstein. And he said, hey, I'm Josh Kushner. He's had a year of investment banking experience. I've had 7 years of government. I'm like, of course we should start a venture capital firm. From like 1870s until kind of 1950s, Birmingham was like the next city or the city of the South.

In 15, 20 years, places are changeable. And I think a lot about what tools can I use from the nonprofit space to investing here in companies to culture cultural but kind of attitude changes that don't make Birmingham try to be anything that it's not. It's not trying to be Austin, it's just trying to be a better Birmingham. Speaker A: Welcome to Dialectic, episode 44 with Jared Weinstein. Jared's work spans technology, business, government, investing, and community impact, and he's made stops across Washington, DC, where he was the personal aide to President Bush, San Francisco, where he worked early with the team at Palantir, and New York, where he spent over a decade building the now legendary VC firm Thrive Capital.

These days, he's focused on Overton, where he's seeding new investment managers, backing high conviction entrepreneurs, and working with myriad folks shaping the future of Birmingham, Alabama, the place he grew up. You might guess from his resume that Jared is a very serious dude, and I think he's certainly someone who rises to the occasion, especially in moments of crisis. I think anyone who knows Jared well, and I've been fortunate to have gotten to know him a bit over the past year, would tell you that he is just absolutely full role of humanity.

He is an amplifier of people, whether it be the leader of the free world, to the team and entrepreneurs he worked with at Thrive, to the investment managers he now backs, to again the people working on Birmingham, whether it be early childhood development or placemaking or whatever else it might be. Jared is a confidant, a friend, a supporter, an advisor, and most importantly is focused on smoothing the curve of risk-taking and helping people become their best self. This was a true honor. Jared has done very little press. I don't think he's done an interview, and it was honor and privilege to go down to Birmingham and hear him tell his story.

I hope you were inspired to be intentional and to think about the ways that you can contribute to the people you want to amplify, the institutions and communities you are a part of, and the way you can bring humanity into the work. You can find more at fm/jared-weinstein, the transcript, all the links. And if you like the episode, please give it a thumbs up, 5 stars. Or subscribe wherever you're watching or listening. Dialectic is presented by Notion. Jared is a collaborator through and through, and so I think it's fitting that Dialectic's presenting partner, Notion, is a tool for how we think together.

They recently launched a campaign around this idea, and I think it's such a fitting frame for how we use software and increasingly how we use AI in the modern age in a way that isn't just about automating things, giving more individuals leverage, but specifically how we work together and do more together. Notion is a collaborative tool for your life's work, and whether you're working with one or two collaborators or a large team, they have built a tool over the last decade that is an amazing place to collaborate. And now, thanks to Notion AI and custom agents, aka little guys who live in your workspace and help you, you can use and get the benefits of AI in a way that is actually aligned with doing the work you and your collaborators care most about and being able to automate away the busy work.

If you don't use Notion or haven't checked it out in a while, you can learn more at com/dialectic. And if you are using it for all kinds of interesting things, I would love for you to share it with me. With that said, here is my conversation with Jared Weinstein. Mr. Weinstein, we're here. Speaker B: Mr. Dahl, thanks for coming. Speaker A: I'm so glad to be here down in the Deep South, as you said. Not my first time in Alabama, but first time in Birmingham. It's good to be here. Speaker B: We're excited you're here.

We need more Jackson Dahl energy down here. Speaker A: It's an honor. We are going to go a bunch of places today. I'm going to start with— I think, um, actually it's worth setting the context. You have spent your life across a bunch of different worlds, um, obviously starting here in Birmingham, going to DC, Silicon Valley, a lot of time New York City, back to Birmingham. I also think if people were to look at your resume, you, you lie pretty low. Uh, we're changing that a little bit today, but if people were to look at your resume, they would infer that you are a, like, a cold-blooded killer, basically.

Like, you are somebody who, like, goes into situations and is operationally excellent and makes things happen. And I think the thing that they wouldn't see on the resume that almost anyone who has ever met you would say is that you are just, like, radiating warmth. And I think that's something that is kind of a funny, funny thing to look at. I also noticed your, like, logline on LinkedIn is Founder, advisor, friend. Mm-hmm. One of your former colleagues at Thrive said Jared is a friend in the truest sense. Well, and so my first question is, what does it mean to be a friend?

Speaker B: Wow, that's really kind. What does it mean to be a friend? I think it means showing up. I think it means assuming the best of the other person. I think it means listening. I love listening. Frankly, I like listening a lot more than I like talking, which is why this is new for me. I like championing other people. I like seeing other people reach places that maybe they don't even realize they could reach. And if I can play a small role in helping them do that, that's really exciting.

I get tons of energy from being around other people. And I also know, and for as long as I can remember, think about how much other people have played a role in supporting me and how good of friends they were to me along the way. And whether they were peers or managers or whomever. Speaker B: Wow, that's really kind. What does it mean to be a friend? I think it means showing up. I think it means assuming the best of the other person. I think it means listening. I love listening.

Frankly, I like listening a lot more than I like talking, which is why this is new for me. I like championing other people. I like seeing other people reach places that maybe they don't even realize they could reach. And if I can play a small role in helping them do that, that's really exciting. I get tons of energy from being around other people. And I also know, and for as long as I can remember, think about how much other people have played a role in supporting me and how good of friends they were to me along the way.

And whether they were peers or managers or whomever. Speaker A: There's an obviously related component But it might not be totally obvious. There are a lot of people who are incredibly warm in their personal lives, and in their professional lives there's like a switch. Um, and I don't mean to say like— I think again, as we'll, we'll talk about, you, you certainly know how to get serious when things need to be serious, but you seem to bring a deep amount of humanity into work, whether it be again in the civic kind of political realm or in all the work you do here in Burning Man, and certainly everyone you talk to at Thrive about Jared Weinstein, that is a common thread.

And so I'm curious how you think about that, maybe where that comes from. There are people who kind of cleanly separate these things. Speaker B: Yeah. Speaker A: And for you, it seems to be a little bit more overlapped. Yeah. Speaker B: Well, there were some pretty formative experiences early, which was being in the West Wing of the White House at 22 years old. And at least our White House, led by President Bush, you know, but also led by Chief of Staff, um, Andy Card. It was an incredibly, of course, serious place, and also a joyous place, even in the most challenging of times.

And I think President Bush recognized that you can, you know, have to take that job incredibly seriously, um, but you can do that with joy, and you can do that with warmth, and frankly, you can, get the best out of people if you have that kind of environment, a supportive environment, a challenging environment. And the White House Chief of Staff, Andy Card, he was kind of a nice guy finishes first kind of person. And that so set the culture for our White House. It was never about any one person. It wasn't even about President Bush.

I mean, he was very much like, we're here for a very short time, stewarding this office of the presidency that the American people, whether they voted for us, or not expect us to do. So you better bring your A game. Speaker A: Yeah. Speaker B: And that's the president and the vice president and Condi Rice and all these different people, but also, you know, 22-year-old Jared Weinstein and whatever you're supposed to do, like bring your A game. Speaker A: Yeah. Speaker B: And that's the president and the vice president and Condi Rice and all these different people, but also, you know, 22-year-old Jared Weinstein and whatever you're supposed to do, like bring your A game.

Speaker A: Yeah. Speaker B: And you can do that with compassion. I mean, he has a, President Bush had a great sense of humor, but he was in there at 6:30 AM, 6:45 AM and being like, man, we only have, maybe 4 years, 8 years to do this job. So we better be sprinting and we better be really intentional about what we're trying to do. And we can do it with friendship. And these are friendships that now, 20 years later, I'm still in touch with these people. They've touched me in amazing ways.

They were great mentors to me. And so I think that's where I learned it. And I'm glad that my Thrive colleagues got to experience and felt that. Speaker A: Yeah, it's interesting. I think there's a default, like the XY axis of seriousness and camaraderie or whatever, family vibe or any of those types of— even joy, to use your word. Those two things don't tend to be correlated. There's a certain kind of feeling that like as things, as the stakes rise, like we all have to like become more robotic. Yeah, I shifted the other way.

Speaker B: I I get it. I think there's cultures. I imagine a lot of my buddies who maybe started their career in the intense New York City hierarchy of banking, it was just, it was a taught behavior. And it's not obvious to me that it works. I think it can in the short run get stuff out of you. It's probably like a dirty fuel kind of orientation. But in the long run and kind of multi-decade organizational and culture building, it doesn't feel like something that's gonna be long-term sustainable or long-term excellence.

Speaker A: Let's start with the beginning, though. I'm curious, like, you're in college at Duke and you decide to work on a political campaign. Mm-hmm. I don't know if it was different then compared to today, but it doesn't seem like most smart, ambitious people are, like, jumping to go work on government. And so I'm curious, and maybe it was slightly different on the campaign versus eventually going to actually work in the White House, but I'm curious what drew you to that in the first place. Speaker B: Sure. So I got to Duke in 1998, and I learned two things right away.

One is there's a sport with a stick with a basket on the end that all the cool guys played, which was not a big sport in the Southeast. I also learned that in order to be successful in life, you left Duke and you worked for these two guys named Goldman Sachs. And if you didn't work for them, like, your life was kind of over. And I was willing to— sign up for that. And I actually thought that I would need to go work for Goldman Sachs or somewhere like that after my junior year.

But I was a public policy major and that required an internship to fulfill the major. And so I needed to get that done after my sophomore year. And I went to the intern coordinator and said, um, could I go work for the Bush campaign? Her face changed a little bit and said, I'm not totally sure why you would want to do that. She may have used different words. Yeah. And said, but yeah, if you get there, we'll give you credit for your internship. And so I started, I think, in October of my sophomore year, cold calling down to Austin, Texas.

I didn't know people, but something about him and I can— and what he was standing for just kind of spoke to me. I wasn't deeply involved in politics. I think there was an aspect of his career that had spanned both business sector prior to going to be governor. That whether he was Republican or Democrat at the time, like it, that kind of career, I think, interested me. And so I was a bit compelled by him. Austin, Texas sounded like a fun place to go, maybe spend a little bit of time.

And after 8 months of cold calling, they rejected me once for an internship. They passed me to someone else. They finally called me kind of toward the end of my sophomore year. I got a call and they said, hey, are you still looking for something to do this summer? And I was, very prepared for an interview. It was much, hold it to me, much easier than I thought it would be. And they said, "When can you be here?" And I said, "I think I can be there in [redacted address] overnight."

In a body, basically. And I got there. I thought I would stuff envelopes for the summer and put up bumper stickers and yard signs. And fortunately, I think really by chance, they put me into a really neat office on the campaign. Karl Rove, the president's kind of strategist, and I was the low man on the totem pole. And by the end of the summer, I was supposed to go abroad for my junior fall. And they said, we think you're doing a good job, why don't you stick around? And I said, well, but I'm going abroad.

Like, that's what I'm supposed to do. Speaker A: This is my plan. Speaker B: And they kind of look at me like, you're an idiot. Like, you're working for the next president, why don't you stick around? And so that led to the campaign and then continued on from there. Speaker A: Did it feel— In any way, did it feel risky? Either on the dimension of just, I don't know, doing something slightly divergent and/or related to the fact that it wasn't a sure thing, like, and obviously very much came down to the wire in the end.

Speaker B: It definitely came down to the wire. It did not feel risky. It became a little riskier after we won because I was gonna go back to Duke for my, junior spring, and some buddies on the campaign started to say, why don't you come to DC with us? And I was kind of like, what, drop out of school? Like, that feels a little riskier, at least at the time. And fortunately, my parents, who played such a role in my life, said, if this is what you want to do, we support you.

And the fact that, you know, these authority figures said, that's okay, that's an okay path to go on, it still may have been risky, but at least I had this kind of like loving support to choose what I wanted to choose. Now, fortunately, one of the more compassionate acts and kind acts was Karl Rove called me and said, I hear you want to drop out of school and come to C. with us. And I said, yes, sir. And he said, Jared, I knew a guy who dropped out of school for politics and he couldn't get his bachelor's degree and he couldn't get his law degree.

And by the grace of God, I'm where I am today. Go back to college and I promise I'll make sure you get up here when you graduate. And I think if I had gone up there, they would've given me like a courtesy job probably in the, you know, I don't know, lead paint division of, you know, some department or something. But I waited, I went back to college. I didn't go to Goldman Sachs. I went up the next summer and interned in the West Wing just before 9/11. I worked for Karl.

I was the only intern in the West Wing, which was, which was pretty exciting and special. And then when I graduated in '02, he helped and they created an entry-level job for me. Speaker A: What did your friends think, particularly when you were in school? Speaker B: I don't think the George W. Bush fan club at Duke was, was that big. Yeah, certainly during the campaign. 9/11 happened my senior year. So then people were kind of like, you know, his popularity went to whatever it was, 80, 90% for that year.

And I think people thought of things a little differently, but people were 21, 22 years old. They were doing their banking interviews and their consulting interviews. I don't think they could, I think they thought it was neat, but they couldn't really imagine it in any way. To your point earlier, there weren't a lot of people that pursued those careers. Speaker A: Yeah, yeah, yeah. Speaker B: They didn't know what it would look like. And I didn't even know what, whether a job would come until almost the last week of college.

Right. Speaker A: I also just think, like, I don't know, interning on a presidential campaign, one thing. Interning in the White House when you're in college is kind of— independent of the political party or whatever, like, kind of insane. Were you like, oh my God, like, how did I get here? Or did I? Speaker B: Absolutely. I mean, if you don't pinch yourself every day when you walk into the West Wing and through those gates, then you're probably in the wrong place. Speaker A: Yeah. You think more people should work in government?

Aspirar to? Speaker B: Absolutely. I think that we have a really special thing here in our country, and it's not perfect. It hasn't been perfect ever, but we aspire for it to be great, and it has done a lot of amazing things. And I don't think that's necessarily kind of like predestined to continue. And it's kind of, I think the words like for the people, by the people, of the people kind of get like lost as this like no big, and there's a lot of countries though where it's not of the people.

And so we actually have a pretty fortunate thing here. And what game have you played? What organization have you been a part of where if, you know, if you don't have the best people a part of it, you have a good chance of winning. And so, I, you know, I think whichever president is in office, I hope that the best people who are passionate about and believe in that president's vision go join in. I think, you know, I didn't agree with everything that President Obama did, but I thought it was great that he brought so many people into government.

I think, you know, President Bush not only looked to people he knew from Texas, but people across the private sector. And so, I think it's an amazing experience. People talk about working in mission-aligned organizations and they talk about how, you know, their Silicon Valley startup is mission-aligned. And I think that's true, but I mean, you haven't seen mission-aligned until you've worked in something like government, maybe the nonprofit sector. And that's really special. And I think even if you do it for 2, 4, 6 years in the arc of a long career, I think you'll grow from the experience and I think the country benefits from it.

Speaker A: You started to talk about it. Your first job, I think, was working on effectively in like scheduling. Speaker B: Scheduling. Speaker A: When you found that out, how did you feel? Speaker B: Yeah, well, you know, it's not the thing that most draws most people to government. And I got a call of kind of a few weeks or so before graduation and they said, you know, Jared, we have a, we have an opportunity we want to talk to you about. I'm like, oh, is it national security or economic policy or what's it going to be?

And they said, scheduling office. And like, what was scheduling office like? Am I going to be responding to, you know, wedding and bar mitzvah invitations from around the country? I think they knew what they were doing. And there's no more kind of precious resource at the White House than the president's time. I mean, there are so many issues that the president could be spending time on, but he needs to be spending time on the most important thing. And really what the scheduling office is, is working to ensure that his very finite time is spent on the most important things.

And so the way it worked is we would get all the requests from across the White House to— for the president's time, and then we'd work with the chief of staff. And so I very quickly got to see what was important. Not everyone at the White House really worked across his schedule. They'd work on their narrow issue. And I was seeing that, okay, we're putting this on the schedule or that on the schedule. And so you kind of see what the priority list is. You see maybe who has more power and relevancy at the White House based on getting things on the calendar.

And so it was really helpful in learning kind of how the whole White House worked and what mattered. And really the kind of probably the early days of my— to the extent I have this operational execution thing that you cited, I think that was very much the early days of it. Speaker A: Yeah, it's kind of an amazing way to get a bird's eye view from like the bottom. Speaker B: Totally. Speaker A: Kind of, uh, in a, uh, yeah, in a, in a way that might be unexpected. Um, what do you think— have you spent much time thinking about like what you did or what you showed when you were working on the campaign that not only had them excited to bring you back but led to that seat, to the extent they were thinking about what that seat meant?

Speaker B: Yes. And I feel so lucky to have had that experience and that they, you know, a few times asked me to take on a next role. And I don't know that I would have worked in any white— I don't know that I would have been the right fit for any president. I think part of it was I was never the smartest kid growing up. I was smart enough. I think I was a very hard worker. And as early as the campaign, you know, I kind of knew and even had bosses that told me stories of how they had been the early person into the office.

And so So I knew I could work really hard. I never cared about, you know, President Bush would call it like peacocking, you know, kind of like showing your own feathers. Like that was never interesting to me. And so I didn't need never to brag about my work or talk about my work either inside the campaign or to people out there. And so I think discretion, you know, certainly in a White House is pretty important. I think whatever judgment a young 22-year-old can show around the job that they're tasked to do, I think I had pretty good judgment.

I could, there was a lot of balls to juggle, to say the least. And I think they felt I probably did that with a kindness, a compassion, but also a, you know, near zero failure rate, I think. And that led after a year and a half or so in the scheduling office to the, the president's chief of staff asking me to join him as his special assistant or kind of. And that is a fascinating role because the chief of staff is really almost the CEO of the White House in a way.

And, and his job is to ensure the White House works in service of the president. And by the White House, I mean everything from policy formulation to legislative strategy to the communication apparatus to the food staff, the floral shop, like the White House grounds, the Secret Service, the advance team. I think I had very much like a service orientation of no job too big, no job too small, do it with discretion. And again, this chief of staff was this nice guy, Andy Card, who Enough good things can't be said about Andy and also our second chief of staff, Josh Bolton.

Andy was, you know, treated the president and the janitor the same way. And Andy had worked in other White Houses. I think he had seen where internal politics didn't serve White Houses particularly well. And so he was very much a, you know, kind of one team, one dream chief of staff. He was very much a, I'm here to make sure other people are successful. Maybe kind of like the first glue guy I experienced in many ways. And, you know, he was first to the White House in the morning, so I had to beat him into the White House to be ready.

Speaker A: What time did you show up? Speaker B: I targeted 5:00 AM, which was a— the alarm went off at 4:12 AM. And someone asked me one time, like, why 4:12? It's such a particular time. And I said, well, 4:10 was too early. I got 2 more minutes of sleep. And if I waited till 4:15, I wouldn't be there at 5:00. And Starbucks wasn't open. I had to stop at the 7-Eleven for a good 7-Eleven coffee. Speaker A: How much would you sleep? Speaker B: My guess is I kind of like got in bed around 11:30 or so, 11, 11:30, and kind of popped up.

Speaker A: Matthew Walker wasn't pleased with this strategy. Speaker B: Right, right, no. No, I sleep with my eyes closed. Speaker A: 22 is for you. Speaker B: Totally do it. Speaker A: When, at what point did, 'cause presumably you're working on the campaign, that's one thing, you're an intern, whatever. When did the like radical stakes and radical pressure, first, like most people get paralyzed when there is high stakes, let alone crisis. Talk to anybody who spent time with you, and I think like one of the things they say is that Jared is a riser.

I have to imagine a huge part of that was how you started your career, but I'm curious like what that was like initially and kind of like navigating that when you're 22 and just trying to succeed in your first job, but also there isn't room for failure. Speaker B: Right, and right, there's other environments, Silicon Valley, failure is the thing. DC, you know, failure is not the thing. I think that I was so fortunate to just see a campaign especially that was, focused, that was not finger-pointing, that was, you know, campaign was a tight race with Vice President Gore.

Things came up during the campaign of, you know, crisis stories. Hey, we're gonna deal with it, you know? And so I think I just saw these, I don't know, quote, adults in the room. I realized those adults may have been younger than I am now, but like, they felt like, the leaders of the campaign, and they were cool, calm, and collected. I mean, President Bush surrounded himself with people who had been there. A lot of people in the campaign had been in previous White Houses, whether it was in his father's White House or other White Houses.

And so it was, you know, we've kind of been there before, you know, act like you've been there before a little bit. The night of the election in 2000, when Vice President Gore, he thought Florida had gone for him, you know, there were election parties happening. Hey guys, we got to stop this party. We got to go back to campaign because Florida is about to be in— and it was not chaos. It was, we've got a job to do. We're sending planes to Florida with lawyers. And, you know, it's like, okay, back, back to your desk.

And it was as if like it was another day of work and the stakes were high. But, and I got to the White House in July of '02. So 9/11 had already happened and there were early I guess, signals that, you know, the Afghanistan War was already happening and then Iraq was kind of on the horizon. Iraq, I think, started in March of '03. So, I mean, you get there, there's no kind of playing around. I mean, the stakes are high. And but I think when the stakes are high and those leaders showed up with, hey, we trust you to do the job we've hired you to do, they're kind.

It's kind of I don't know, like a psychologically safe environment while still having high stakes. And, um, I think I aspire for high-stakes environments that are psychologically safe too. Speaker B: Right, and right, there's other environments, Silicon Valley, failure is the thing. DC, you know, failure is not the thing. I think that I was so fortunate to just see a campaign especially that was, focused, that was not finger-pointing, that was, you know, campaign was a tight race with Vice President Gore. Things came up during the campaign of, you know, crisis stories.

Hey, we're gonna deal with it, you know? And so I think I just saw these, I don't know, quote, adults in the room. I realized those adults may have been younger than I am now, but like, they felt like, the leaders of the campaign, and they were cool, calm, and collected. I mean, President Bush surrounded himself with people who had been there. A lot of people in the campaign had been in previous White Houses, whether it was in his father's White House or other White Houses. And so it was, you know, we've kind of been there before, you know, act like you've been there before a little bit.

The night of the election in 2000, when Vice President Gore, he thought Florida had gone for him, you know, there were election parties happening. Hey guys, we got to stop this party. We got to go back to campaign because Florida is about to be in— and it was not chaos. It was, we've got a job to do. We're sending planes to Florida with lawyers. And, you know, it's like, okay, back, back to your desk. And it was as if like it was another day of work and the stakes were high.

But, and I got to the White House in July of '02. So 9/11 had already happened and there were early I guess, signals that, you know, the Afghanistan War was already happening and then Iraq was kind of on the horizon. Iraq, I think, started in March of '03. So, I mean, you get there, there's no kind of playing around. I mean, the stakes are high. And but I think when the stakes are high and those leaders showed up with, hey, we trust you to do the job we've hired you to do, they're kind.

It's kind of I don't know, like a psychologically safe environment while still having high stakes. And, um, I think I aspire for high-stakes environments that are psychologically safe too. Speaker A: What is— you mentioned the White House Chief of Staff being like the CEO. I guess the assumption there is that the president is like the CEO of the government. Speaker B: CEO of the government, you know, like chairman of the White House. I mean, the president can't You know, he can't be so in the weeds operationally of everything the government does.

The president doesn't decide what color to paint the, you know, Navy ships. He doesn't choose everything. And so I think in many ways, the chief of staff's job is to ensure that the whole White House and the president is kind of like teed up to make decisions at the right time. And so if the legislative session is starting in a few months, are you going through a policy debate process around certain issues and having the cadence of meetings such that the decision is made not too early to where it becomes stale and not too late that it is kind of irrelevant.

And so how do you ensure that whole thing works? And, you know, the president puts the right people in place. I mean, he chooses the chief of staff and he chooses his national security advisor and he, And I think with the chief of staff, he's really looking for someone that makes the system work. Speaker A: Is the— like, to what extent is the White House as an organization like other companies or startups? Is it part— part of what maybe you were alluding to, too, is like— and maybe we'll get to this— is like the president maybe in some sense, like, doesn't do that much.

And what I mean by that is the president's job is almost explicitly, I would assume, like judgment and people. Um, and like, if they were— Speaker B: if they're too in the weeds on anything, you will never hear me say that the president doesn't do that much. Speaker A: Yeah, it's a ridiculous statement in some sense. What I guess what I mean is like, I would imagine it's very, very costly anytime the president has to go into the weeds. Speaker B: I think it's very costly for the president to spend time on anything other than the most important stuff, and there is a lot of important stuff out there, and it's not just stuff in America, the president doesn't get to choose like pet issues, you know, like, oh, I want to do, you know, libraries or I want to work on forests, like maybe, but like the president, you know, the, it's not just American issues that get to his desk.

Like the whole world is looking for what the president of the United States' view or support or of any issue is. And so the White House has to decide, and I think the chief of staff plays a real important role of kind of, are we spending our time on, the right things. And so— Speaker A: and giving him leverage, giving him leverage. Speaker B: But the buck stops with him. I mean, the only two people voted on were him and the vice president. And really, you know, it's, it's the president.

And so he has to make decisions. He, he was not a, like, let's throw people under the bus if things aren't going well, especially with staff. I mean, it was hard times, obviously. Like, there were challenging times with foreign affairs and the wars. There were challenging times with his polls. I think more than the president had to remind us, like, don't focus on the polls, don't focus on the editorial in the, you know, newspaper that is critiquing me written by a 26-year-old op-ed person. Like, that's not the most important thing.

It's, it's are we operating from principles? Are we operating and making the best decision possible with imperfect information and, and then executing on it. Speaker A: Yeah. You were working for the chief of staff, I think the second chief of staff, and then you got a call down to the White House. Excuse me, down to the Oval Office. Can you tell me that story? Speaker B: Sure. So I was the chief of staff's aide and I was kind of the backup to the president's aide, who was and is and remains a great friend of mine.

So if he was ever sick, I would fill in. So the president kind of knew me. Speaker A: And this is what, like 2, 3 years in? Speaker B: This is 3 years into being the chief of staff's aide. And, and you needed a backup. I mean, the president had to keep going. If, if Blake, who was the president's aide at the time, got sick or needed help, you needed someone that could seamlessly drop in. And Blake was going off to business school. And so you knew that there was a new personal aide that was likely.

And I think it was likely that I was potentially going to get the job. But, but the president needed to consider a range of people and what was best. And you understood that. And so on May 1st, 2006, at like 7:04 AM, I remember my phone, it rings and it says, Oval Office, Karen Keller, who was the president's secretary. And she said, "Hey, can you come down here?" And that was pretty normal because I would do tasks for them or go take stuff. And so I walked the 30 feet down to the Oval Office and I pop in and say, "Hey, Karen, what do you need?"

And she said, "I don't need you, he does." And the next thing I hear is, "Jerry, get in here." And he's in there with chief of staff, it had moved on to Josh Bolton at the time. And he was going through his morning papers and stuff. And he said, you know, Blake's going off to business school. What do you think about riding shotgun with me for the rest of administration? And I said, let's do it. And that was the end of the job interview and offer. Speaker A: How was that walk back to wherever you were going?

Speaker B: You got the tingles. I mean, it was, I think, I think as early back to the campaign of which at the time would have been 6 years prior. Something about that job spoke to me. I mean, it could have been that the West Wing show and Charlie, who was this character that served on the show in this similar role. I mean, it was just, it just felt like, and I think it was the neatest job a 20-something could have. And I didn't call my parents a lot during the White House experience.

I didn't want to be bragging. And I think I was worried that if I shared too much with them, they would brag to people. Right, right, right. But I think I sat with it for a little bit and then called him and told him. Speaker A: In that job, the White House, or excuse me, the president's aide, sometimes called the body man, like what actually is the job? Speaker B: It's not really a JD. It's kind of whatever makes sense for the president. For our president, for President Bush, it was, deeply understand his day, deeply understand the kind of details of the day, the movement of the president.

And I can walk through what a day looked like and also understand his preferences. I mean, you wanted him always operating at his best. And that didn't just mean, you know, the biggest issues. It also means like, hey, from 6:45 AM when he gets into the Oval until he goes to bed, like, Does he have the right information? Are the right people in there to brief him? You know, he is famous for being a punctual— and by punctual, I mean 15 minutes early— kind of person. And so we were always keeping things moving.

He never wanted to be briefed with too much information of like, Jared, why are you telling me this? And at the same time, he wanted— you needed to give him just the right information for him to be successful. Speaker A: Yes. Speaker B: Yeah. Speaker A: You're feeding this like incredibly high-stakes, super complicated machine and just like trying to like any, like no, no speed bumps. Oh gosh. Speaker B: And as the personal aide, you're trying to do this, you know, being that he would always remind you, you know, Jared, you're not the Secretary of State, you're not the, you know, like you are kind of here to help all of us be successful.

And really like within earshot, out of camera shot was a bit of our personal aide motto. you know, stay behind the scenes and make it work. Speaker A: How much did you sleep when you had that job? About the same. Speaker B: About the same. I mean, I, I tried to get in by 5, and what that looked like was I would get a duplicate copy of his briefing, his nightly briefing binder, and which meant his schedule, the briefing materials on his events, the memos that he would receive, whether those were policy time on tax policy or education policy, copies of his speeches, anything that he was receiving, I would get a duplicate copy mainly to just have with me if he needed it.

But, I use that as a, you know, I would consume it every morning and I would start to think about, is this gonna work for him? How was this day laid out? How was even the event laid out? Why did we do the press at the start of this meeting versus the end of this meeting? Why is, you know, the Super Bowl champions are coming in. Why did we do this this way? Just very— Speaker A: Keep the flow, basically. Speaker B: Keep the flow. And, you know, if I was in sync with him, I would've fired off a bunch of emails in the morning asking people for clarification, maybe suggesting, testing changes, and then he would come in at 6:30 or so and start going through things, and he'd say, Jared, why are we doing this event this way?

And if I had nailed it, I would've been like, sir, actually I saw that as well. I'm gonna work on a change, make sure it's, and part of it was that so much of it was like he wanted to be considerate of others. I think everyone kind of tries to like do whatever the president wants, but he doesn't want people waiting in line for an hour. He doesn't want people, How do you make it such that their experience at the White House is not, oh my gosh, we're here to kind of make the president happy?

The president was welcoming people to the White House, but that was what a morning looked like. At 8:00 AM, the CIA briefers would come in. He'd do a briefing for that, then maybe an FBI briefing, then kind of a news communication briefing. And then it was, you know, 9:30, it's okay, the, you know, the prime minister of this country is coming in and the press is going to do that. And he'd need to be briefed for 5 minutes before that. And then after that, you know, I'd say, sir, the It's time to go.

We need to go over and, you know, see Future Farmers of America are here for you to speak to for 5 minutes and take a photo. Then we're gonna go down and have lunch, you know, with economic policy leaders. And then we're gonna fly to Michigan and I'll make sure the helicopter lands on the South Lawn at just the right time so that it doesn't disturb things. Speaker A: Keep the flow, basically. Speaker B: Keep the flow. And, you know, if I was in sync with him, I would've fired off a bunch of emails in the morning asking people for clarification, maybe suggesting, testing changes, and then he would come in at 6:30 or so and start going through things, and he'd say, Jared, why are we doing this event this way?

And if I had nailed it, I would've been like, sir, actually I saw that as well. I'm gonna work on a change, make sure it's, and part of it was that so much of it was like he wanted to be considerate of others. I think everyone kind of tries to like do whatever the president wants, but he doesn't want people waiting in line for an hour. He doesn't want people, How do you make it such that their experience at the White House is not, oh my gosh, we're here to kind of make the president happy?

The president was welcoming people to the White House, but that was what a morning looked like. At 8:00 AM, the CIA briefers would come in. He'd do a briefing for that, then maybe an FBI briefing, then kind of a news communication briefing. And then it was, you know, 9:30, it's okay, the, you know, the prime minister of this country is coming in and the press is going to do that. And he'd need to be briefed for 5 minutes before that. And then after that, you know, I'd say, sir, the It's time to go.

We need to go over and, you know, see Future Farmers of America are here for you to speak to for 5 minutes and take a photo. Then we're gonna go down and have lunch, you know, with economic policy leaders. And then we're gonna fly to Michigan and I'll make sure the helicopter lands on the South Lawn at just the right time so that it doesn't disturb things. Speaker A: And you're like the primary interface for all of the things happening basically. Speaker A: And you're like the primary interface for all of the things happening basically.

Speaker B: At a very operational level, right? Speaker A: Right. Speaker B: You know, like just, and, and you'd say to, you know, Secretary Rice, he's, he's gotten the information you've passed on because she's have her own schedule. Or the Chief of Staff would say, hey, have we told him about this yet? But, but, and it was the, the other staff in the Oval Office, his secretary, and like, we were basically just making the minute-by-minute operations and logistics, you know, happen. Speaker A: How much time do you spend together? I mean, I guess it's, it's in these like 10-second spurts sometimes, but you're basically just with him the entire day?

Speaker B: Unfortunately for him, he had to spend a lot of time with me. You, he, you, you don't sit in every meeting. When he would go into a meeting, I would make sure it was working and he had what he needed and the right people were in the room. And then I would go out and be thinking about the next meeting or getting the press ready to come into that meeting. So most of the waking hours, you know, but then he would leave usually to go back to the residence by late afternoon.

He'd maybe get a workout in, start working again on the next day's materials. He'd call over for stuff. Speaker A: Yeah. Speaker B: Every now and then I had to wake him up in the middle of the night to sign a bill before midnight or get something done. That's not the most fun part of the job. Speaker A: How much consistency? I guess I'm curious, like how much consistency and structure there is to the president's time versus just reacting to— obviously, there are crazy things happen and then you're just reacting, but are most days relatively similar in terms of you're meeting with the CIA guy and duh-duh-duh, and then it breaks if there's chaos or like?

Speaker A: How much consistency? I guess I'm curious, like how much consistency and structure there is to the president's time versus just reacting to— obviously, there are crazy things happen and then you're just reacting, but are most days relatively similar in terms of you're meeting with the CIA guy and duh-duh-duh, and then it breaks if there's chaos or like? Speaker B: Yeah, he's a— I don't know what other White Houses operate. He was a very disciplined, you know, basically everything in 5-minute chunks was planned out throughout the day, and he ate at the same time.

The briefings in the morning were consistent and you tried to plan out in a— you probably knew his schedule down to an event-by-event level 2 to 3 months out or so. And you knew the themes, like maybe a theme of a week could have been economic prosperity. So you're going to this factory in Ohio or Silicon Valley to talk about things. And so you knew the like themes, but I mean, so many things show up in the world that you have to be prepared for. And it's not even— it's certainly there's the massive stuff, there's the 9/11, and there's the wars, and there's the financial crisis, but even other stuff that just, you know, a Supreme Court justice passes away, so you've got to be ready to nominate a new Supreme Court justice, or, you know, various many, um, I don't want to call them crises because they don't feel like crises, but they're things that throw off your kind of planned schedule.

Speaker A: You're very used to like divert— Speaker B: yeah, totally. Speaker A: How many, um, how much of his— like, maybe this is a dumb question, like, how many decisions is he making in a day? Like, presumably all anybody ever wants is just like, what should we do, what should we do, what should we do, what should we do? Hopefully some of that's getting abstracted away. Speaker B: I think he's making the big decisions. He's certainly making decisions on, you know, who's in his cabinet, uh, who are not other kind of leadership roles across those agencies.

They're recommending, you know, we want to put in this person as the undersecretary for this issue. Um, absolutely is responsible for the senior staff of the White House, but you don't want him making decisions, and he didn't want making decisions that other people Could there's also energy fatigue, which is like you're doing these small things and then you have to. Yeah, but I don't think the Condi Rices of the world, you know, incredibly impressive people want to be micromanaged either. Like he, you know, he wasn't going to be Secretary of State.

Like that was her skill set. And Hank Paulson is that, you know, you wanted great people in there, but when it came to, okay, sir, we've got our banks are failing, our financial markets are, you know, tailspinning. Here's a set of recommendations. And got it. He wanted to create create the environment that he got the best ideas and then made the decision. Speaker A: In what ways did he model excellence, and in what ways do you think he was a particularly good leader? Speaker A: In what ways did he model excellence, and in what ways do you think he was a particularly good leader?

Speaker B: I readily admit that, um, probably no other person other than my parents and grandparents have affected me more positively than George W. Bush. Um, I'll come back to as a leader, but He is a great father to his daughters. It was really fun, frankly, watching him as a husband to Mrs. Bush. Their friendship and partnership and sense of humor between each other was, maybe I'll call it beautiful. He was a great friend. I thought it was really neat. I'm pretty sure, like, He had dinner before he became president with the same friends that he had dinner with the day after he left the presidency.

And he wasn't someone that needed to come to DC and, you know, care about, you know, being out at the restaurants all night. Like, he kind of didn't sweat the small stuff and focused on the big things, which was his family, for him, his faith, and certainly this incredible responsibility that was given. As a leader, he was, I think, incredibly consistent. I knew what mattered to him. I knew what he was looking for. I knew what he wanted out of me and his and others. And so you kind of knew what the bar was.

There was no guessing. Speaker A: No ambiguity. Speaker B: No ambiguity. He was, It's funny because I recognize that his public speaking maybe wasn't always his strong suit. And I think that was really unfortunate because that's how so many people saw him. And that can lead you to make assumptions about, you know, intelligence or judgment or all this kind of stuff. And it's too bad. And I think as the White House staff, sometimes we put him in the wrong setup, you know, behind a podium saying words, giving a long speech.

If you ever see him in like an environment where he's kind of a, uh, just a general free-flowing fireside chat. I mean, not only everyone says, oh, he's funny, or I want to have a beer with him. Sure, it is fun to be with him, but he is incredibly wise and sharp. And Secretary Rice used to say, you know, I would get so prepared for my meetings with him, and I thought I would have every issue left and right dissected and understood, and I'd come in and I'd tell him and he'd ask a question and it was always, it was like, that's exactly the right question he should be asking at the right level.

And so he's an incredibly acute question asker. Speaker A: In a way that's like intuitive? Speaker B: In a way that just gets to the heart of the issue. And it's kind of like, that's the thing that really matters. And I think that was a skill that I saw, I really admired and it kind of, It also is really efficient. It doesn't waste a bunch of time talking about things that we don't need to be talking about. Speaker B: In a way that just gets to the heart of the issue.

And it's kind of like, that's the thing that really matters. And I think that was a skill that I saw, I really admired and it kind of, It also is really efficient. It doesn't waste a bunch of time talking about things that we don't need to be talking about. Speaker A: Right, right, right. Speaker B: And to do that in a way that is still motivating and inspiring to incredibly smart people who are in those rooms, who've now gone on to do amazing things in their career. Like, so he, I think he is someone that people who worked for him only became fonder and fonder over time.

It wasn't someone that, oh gosh, wow, I just want to work with him. And then you realize, I mean, no one's perfect. He's never claimed to be perfect, but you grew in admiration for him as you worked with him more. Speaker A: Based on your experience with him, do you have a particularly— and maybe just an experience inside— do you have a model of what you think is important in a president that might be different from everyone kind of looking at it from the outside, or even just like what leads to success in actually doing the job?

Speaker B: I think that— I think the culture of the White House really matters. I think that ensuring you have great people who can bring you their best recommendations and that you can have an environment— I mean, in that Oval Office, when the president, the vice president, everyone— like, that's an intimidating place. So can you ensure that you're getting— Speaker A: it's not getting, like, filtered, not getting filtered, not having people coming, Mr. Speaker B: President, you look great today, that's a beautiful tie. I mean, like, sycophantic behavior doesn't help the White House and doesn't help the president make the best decisions.

And so I think that really matters. I think it's why, as we were talking earlier, ensuring you get the best people willing to serve, if only for a short time, really matters. It needs to be a well-oiled machine. 'Cause the president really, if the president is getting a decision that's like a 90/10 obvious decision, like that's a bad use of the president's time. Like other people can make that decision. Yeah, yeah, yeah. Like cabinet secretaries others. The president is really only getting the decisions that are like 50/50 and that really smart people are making very good points on either way.

And you just ultimately have to go with one. Speaker A: Wow. What do you think people get wrong about him? Speaker B: I mean, one, he's a, he's really like a heart-led person. He is really compassionate. He's a bit of a soft— I'm a softie sometimes. He's a softie too. I think people created this like frat guy image of him. I think he was a guy that was really well-liked by both the frat crowd and the, you know, more academic nerdy crowd. Like he's just, he loves people and he loves seeing the best in people.

I think they think that, you know, again, as I said earlier, people are like, ah, like what is, you know, what a nice guy, really want to have a beer with him. And the have a beer with him comment, to me always, it felt like it was signaling for like, he's just like a funny guy to be around. And I think it misses again how acute of a question asker. When it's business time, you snap into business time. And it's not because it's in his best interest. It's like, Jared, this is the United States people like we're talking about here.

This is serious. And so I don't think people fully appreciated that. Speaker A: Yeah. Speaker B: Because ultimately our White House, which, Again, you can debate, and he talks often about like, I'm going to be long gone by the time they figure me out. And so I can't worry about the popularity thing. But, but he, you know, you have to make really good decisions. And he, and he's responsible and put in place the apparatus to have the information to make, you know, all those decisions. And I think history will look fonder and fonder on him.

Speaker A: Obviously related, maybe, maybe a similar answer, but I'm curious what you hope he is remembered for? Speaker B: I think— I, I hope he is remembered for, you know, kind of who he truly is. I think he's a deeply— he, he loves our country. He happened to be president at one of the kind of most unimaginable attacks, uh, in our homeland that really changed how we think about security and things coming to our shores. And it wasn't obvious on September 12th that another one wouldn't happen days later, months later, years later.

And he protected us for a long time. I think that he really led with what he believed was in the best interests of the country. I think he motivated great people to come into government. I do think values matter in all of this, and he's a very values and principles-oriented person. If you're— he never chased popularity. I mean, he would say if you're chasing popularity, like, it's fleeting, you're going to chase your tail and it's going to change with the wind. And so you've got to have a set of principles that you follow.

Speaker A: There were a couple other people you had mentioned being influential on you while you were in the White House: Kaplan, Dina Powell, Kevin Warsh. I'm curious Any things that come to mind about those people or other folks? Speaker B: You know, at its best, the White House does attract the best and the brightest. I don't know how I kind of like slipped through the cracks, but, you know, there were people 5, 10, 15 years older than me, separate from the president, that were around. And, you know, Joel Kaplan was kind of Deputy White House Chief of Staff, and Dina Powell was first in the White House and then went over the State Department.

I 2 of them are like top leaders at Meta now. Kevin Warsh, who's now nominated to lead the Fed, like whip smart and also like, Jared, let me teach you about this. Or, you know, and so like to get to kind of watch these people, I think when you talk about the president, that feels so far away. He's, you know, decades older than you. But to have people who are like 5 to 10 years where you could somehow see a path in what they did very recently and to get to model your behaviors at a young age in your career.

I mean, what a, what a total amazing experience. Speaker A: You mentioned there are some people who are— maybe I misunderstood this— are staff who stay in the White House through every administration. What is that? Who are those people? Speaker B: Yeah, it's actually the majority of not only the White House staff, but government broadly. I mean, there's amazing people who've committed their careers to helping government work. And that can be, you know, Secret Service doesn't change with administrations. A lot of national security people don't change. I mean, you don't want like, oh, the people providing you information on what's going on in North Korea are kind of like political.

Speaker B: Yeah, it's actually the majority of not only the White House staff, but government broadly. I mean, there's amazing people who've committed their careers to helping government work. And that can be, you know, Secret Service doesn't change with administrations. A lot of national security people don't change. I mean, you don't want like, oh, the people providing you information on what's going on in North Korea are kind of like political. Speaker A: Right, right. Speaker B: You add political leadership or, And that, that comes and goes. But you want people who, again, it is an organization, it is a machine, it is a company, and that needs to keep working.

And so I've been back there a few times since, and I'll sometimes see, you know, people that, you know, again, Secret Service or other people, and they're like, what, you know, what are you doing? It's great to see you. What are you doing back here? And it's kind of a really nice thing that like, despite administrations there is a set of people that are keeping the machine kind of going as new leaders come in. Speaker A: You mentioned the word political. People outside of politics use political in a— with a negative connotation.

I'm curious, particularly maybe in the context of like since, since the White House, you've mostly been in the business world. To what extent that word can be positive. Is there a time when being political in business is useful? Speaker B: Yeah, well, it's funny, people said, you know, you think you'll go back to politics or something? And I didn't feel like, I felt politics was like the campaign. That feels like politics in a narrow sense. And I was in government service, you know, there's politics around it and there's certainly, you know, a Capitol Hill of like debating, you know, bills and Republicans versus Democrats.

You know, especially, you know, the White House and the issues that we had, that felt like government service. And I think politics kind of gets laid over that, but it's not really what you're thinking about when you're there. I think on the campaign, you're thinking about, you know, how do we win these votes? What are the poll numbers? Set polls, like that feels like more politics. And I think that it probably pushes people away 'cause they think it's all about that. And I'm not naive. I mean, that is, in many ways the sport of aspects of DC.

And we see that on the news as much as we see anything else. But there is a ton of work day to day and the majority of the work that is not service, it's like the workings of government and whether that's the National Park Service or, you know, the embassy in Tanzania or the, you know, energy overseeing of nuclear facilities. I mean, that's like government service. That's not like politics. And so I spent a number of months on the campaign and then I spent years in White House in service. Speaker B: Yeah, well, it's funny, people said, you know, you think you'll go back to politics or something?

And I didn't feel like, I felt politics was like the campaign. That feels like politics in a narrow sense. And I was in government service, you know, there's politics around it and there's certainly, you know, a Capitol Hill of like debating, you know, bills and Republicans versus Democrats. You know, especially, you know, the White House and the issues that we had, that felt like government service. And I think politics kind of gets laid over that, but it's not really what you're thinking about when you're there. I think on the campaign, you're thinking about, you know, how do we win these votes?

What are the poll numbers? Set polls, like that feels like more politics. And I think that it probably pushes people away 'cause they think it's all about that. And I'm not naive. I mean, that is, in many ways the sport of aspects of DC. And we see that on the news as much as we see anything else. But there is a ton of work day to day and the majority of the work that is not service, it's like the workings of government and whether that's the National Park Service or, you know, the embassy in Tanzania or the, you know, energy overseeing of nuclear facilities.

I mean, that's like government service. That's not like politics. And so I spent a number of months on the campaign and then I spent years in White House in service. Speaker A: Yeah. From the outside looking at it, it does feel that things feel more political across the board today. Speaker A: Yeah. From the outside looking at it, it does feel that things feel more political across the board today. Speaker B: Yes. Speaker A: And it's like, I don't know, you always wanna be a little careful of being like, this current time is different.

Like, but it, yeah, it does feel that. That, I don't know, I wonder if the pendulum— Speaker B: I mean, I think there's— does feel concerning that, you know, it feels like our districts are either getting more red or more blue and there's less meeting in the middle coordination. It feels like it is more zero-sum and it feels more of kind of like attacking the person kind of orientation. I mean, there was a really neat experience I had towards the end of the time in the White House when Tony Blair, Prime Minister Blair, was visiting the White House and he was, the president was busy with some meetings and he said, Jared, go check on Prime Minister Blair, see if he needs anything.

And I just thought I'd like go get him a water or coffee. I didn't really know. And I walked out there and he said, why don't you sit down? I was like, oh my gosh, like, you know, what is about to happen here? And we were talking and he was near the end of his career. And I asked him what's changed since he got into service politics and now. His immediate answer was that it used to be very much about like debating ideas. And certainly over there, there's a lot of debate that's part of their system.

And he really felt like it had moved to kind of more ad hominem attacks on the person. And it feels like that's a really, that's the easier game to play. And in some ways, I guess all of us allow that on X and the new, it's like that's easier to play. It's harder to kind of debate the ideas, but that's actually what matters. Speaker A: Totally. Speaker B: And it— Speaker A: and that's also easier to root for a person than an idea. Speaker B: Yeah, yeah, yeah, absolutely. Speaker A: Like lower hanging fruit.

Speaker B: Lower hanging fruit. And I think that's also why probably a lot of good people are like, why do I want to sign up for that? I don't need to go have a bunch of arrows thrown at me. Speaker A: What do you think C. does really well compared particularly to Silicon Valley and New York? Speaker B: People may, may chuckle at this comment. I left less cynical than I arrived. And I think DC, you can look from the outside and feel pretty cynical about it. There are some incredible— I mean, we talked about the career people in government.

I mean, deeply committed to doing a job for our country. I think people are really trying to get to the right answer. I actually believe that even at the most highest political level, I think it— the system Unfortunately, it does kind of move you to horse trade and negotiations and, and, and so it's not great. I think that it is a, it is really mission aligned. I don't, I think the other markets that I've lived in, like there's ambition in New York and, and excitement and there's certainly, you know, a future looking frontier in Silicon Valley.

But, but mission alignment is real in DC. Speaker A: Yeah. People would say that Silicon Valley is super mission aligned. But you've made that comment twice now that there's a different weight maybe to the— Speaker B: I do think that there are, that great organizations in Silicon Valley have missions to them. And I think that is a positive force. In my time with Palantir, I saw what was a very, you know, hard software, you know, data integration analytics, like, but I think that company did, help remind people that despite that work, there was like an exciting mission behind it.

But I just think it's a different level. And by the way, at the time Silicon Valley, that I was in government and then left for the West Coast, the connectivity between Silicon Valley and DC, it was like, you know, speaking different languages. Whereas now obviously there's increasing in an exciting way, there's more connectivity. Speaker A: Yeah. People would say that Silicon Valley is super mission aligned. But you've made that comment twice now that there's a different weight maybe to the— Speaker B: I do think that there are, that great organizations in Silicon Valley have missions to them.

And I think that is a positive force. In my time with Palantir, I saw what was a very, you know, hard software, you know, data integration analytics, like, but I think that company did, help remind people that despite that work, there was like an exciting mission behind it. But I just think it's a different level. And by the way, at the time Silicon Valley, that I was in government and then left for the West Coast, the connectivity between Silicon Valley and DC, it was like, you know, speaking different languages. Whereas now obviously there's increasing in an exciting way, there's more connectivity.

Speaker A: You worked for the president briefly, post-White House. Speaker B: Correct. Speaker A: You decided to go to business school. Speaker B: Correct. Speaker A: Before we get into where you decided to go, I guess I'm curious, like, back to the theme of risk, what was going through your head at that point? What felt like the obvious choice? What was business school? Did it feel risky? Did it feel like you had to kind of go do something different? Speaker B: So the president was very much a sprint to the finish kind of leader, and I and a lot of us were committed.

I mean, we had the financial crisis, we had wars going on. We were sprinting to January 20th, 2009. And not only were we sprinting to the end, we were also really committed to setting up the White House for whomever became president, ultimately President Obama. So it was all hands on deck until the last day. And January 20th came, I was the last person in the Oval Office with him on January 20th, 2009, when President Obama was getting inaugurated in. And we went up to Capitol Hill and then flew back to Texas that day.

And everything was gone from Texas, all of the, you know, the military trailers and the Situation Room down there. And it was like, I think I stayed in a motel that night versus what I would have stayed in when he was president. I mean, what was really fascinating is that that day that President Obama, and at 12 o'clock when he's sworn in, President Bush was president until 11:59. I was his personal aide. And right at 12 o'clock noon, my BlackBerry stopped working. It's like they just switch over to the new administration.

So crazy. It was fascinating. And timing was really interesting because the next day, I almost think, I think the 21st and the 22nd, the business school notifications came out and it was almost kind of like your next chapter was starting. Speaker B: So the president was very much a sprint to the finish kind of leader, and I and a lot of us were committed. I mean, we had the financial crisis, we had wars going on. We were sprinting to January 20th, 2009. And not only were we sprinting to the end, we were also really committed to setting up the White House for whomever became president, ultimately President Obama.

So it was all hands on deck until the last day. And January 20th came, I was the last person in the Oval Office with him on January 20th, 2009, when President Obama was getting inaugurated in. And we went up to Capitol Hill and then flew back to Texas that day. And everything was gone from Texas, all of the, you know, the military trailers and the Situation Room down there. And it was like, I think I stayed in a motel that night versus what I would have stayed in when he was president.

I mean, what was really fascinating is that that day that President Obama, and at 12 o'clock when he's sworn in, President Bush was president until 11:59. I was his personal aide. And right at 12 o'clock noon, my BlackBerry stopped working. It's like they just switch over to the new administration. So crazy. It was fascinating. And timing was really interesting because the next day, I almost think, I think the 21st and the 22nd, the business school notifications came out and it was almost kind of like your next chapter was starting. Speaker A: But notifications like admittance?

Speaker B: Admittance. Speaker A: So you had already applied? Speaker B: I had applied in the fall of '08. I actually remember I went into the president's cabin on Air Force One and said, it was probably August or September, and said, sir, I'm thinking about business school. And I think he kind of, he is like, yeah, you want me to write a recommendation for you? And I said, well, if you're open to that, I'd be honored and would mean a lot. Speaker A: It probably helps. Speaker B: It was nice.

I mean, he wrote like 3 hand— a long handwritten note to both, to the schools I applied to. But I also, it was really fascinating. I remember the experience. I said to him, and if you're open to it, I'd be happy to or honored to come to Dallas and help you build the post-presidency. And he kind of was taken aback in this really kind and humble way, as if like he was like, you'd do that? And it was like, for him, it was so obvious why someone would work at the White House in support of the president, but to go and work for him post-presidency, it really, I think that was my, that's how I took it of like, wow, if you're willing to come down there when I'm no longer president and help me in this new chapter for a bit, that'd be amazing.

And so a lot of, in addition to sprinting to the finish during the, fall of 2008 and early days of 2009, we were also building his team down there. And I, and I mentioned Blake Gottesman, his, his prior aide, he had gone off to business school and then actually came back to the White House for the last few months of the administration. And he and I teamed up to think about the Dallas office and his post-presidency office. And so I was thinking about people in the White House that could come down there and people that the president probably knew or had seen around the White House but didn't know well.

And I said, well, this person could be your assistant or this person could be your chief of staff or, you know, chief. And that was really fun. That was kind of my first org building experience. Speaker A: Yeah. Speaker B: And so it was really neat because we got to Dallas and he knew the president appreciated me, but he knew me as like his personal aide. And then we get to Dallas and like the, the Condi Rices are gone and the Karl Roves and the Hank Paulsons. And he's like, I got Jared who's gonna figure this out and Blake's gonna figure this out for me.

It's like, gosh, like how the mighty have fallen. Like, you know, he has to rely on us. But we built a really good team down there. And we also started thinking about what this post-presidency institute and life for him would be like. And, you know, these presidents usually build libraries and stuff like that. And we actually hosted a session a month or two after he left office. A bunch of former advisors came down to talk about what could this Bush Institute look like? And I remember, one of his good friends kind of raised his hand and the president was in the room and people were talking about doing a think tank and all this kind of stuff.

And his friend said, you know, Mr. President, with all due respect, there's something about like the George W. Bush think tank that doesn't really like seem like on brand for you. He's like, it's like the George W. Bush, let's get something done tank, you know? And I think that was, you know, it was, it was a joke in many ways, but it also was very much of like, how do you build something that is very much about doing things and not just putting out white papers. I mean, the president's not a white paper kind of guy.

And so that was this incredible 6 months and a really new relationship that I developed with him. And I'm really glad I did it. And it changed, I think, my friendship with him. And then the summer of '09 came and it was time to figure out business school. Speaker A: Yeah, like, you had applied to business school before. What was the calculus on whether to kind of double down on DC? I mean, when you applied to business school, were you thinking you would go back into politics? Like, how were you thinking about— Speaker B: If you think back to, you know, college, like, I was drawn to work for this president and see where this journey took me.

But I think I even— what initially drew me to George W. Bush was that he had had a career in business and before he went into service. And yes, it started in my 20s. But, you know, there were two other personal aides before me in the White House, and they had all gone to business school, and, and president had gone to business school earlier in his career. And so I, I said I was less cynical about DC than when I arrived, but I still wasn't sure that that's where I wanted to spend my whole career.

I had an incredibly rich experience. My desk was, you know, 10 feet from the Oval Office. So I'm not sure I wanted to go be a, you know, junior lobbyist in town or go work on Capitol Hill, like at that point. Speaker A: Totally. Speaker B: I, I, maybe it would come back at some point, but I, I thought I wanted, I knew I wanted to do something different. I wanted to try the private sector. That's broad. I didn't know what that totally meant. I was a little nervous that if I, that the easy job for me in the private sector would've been like going to work for the, you know, a chief of staff to some CEO at, Facebook or Goldman Sachs or stuff like that.

And that's right. Not really the direction. I didn't want to go do the same thing I had done for a private sector leader that felt maybe a little administrative or, you know, too oper— kind of too paper pushing. I mean, those are important jobs and the, and the chief of staff role in the private sector certainly evolved. But I, so I didn't know, and I thought business school was an interesting way to, arguably, I don't know if I'd say it wasn't a step back, but it was a little bit of like a pause.

And yes, you're in class, but you're getting so much is coming at you from incredibly impressive peers who have come from different industries. And you get a chance to kind of like think about the landscape before you make your next move. Speaker A: It's also a little bit of like a structured sabbatical. Like I'm sure on some level you were like, yes. Speaker B: I mean, especially at Stanford, which is, I think there was a great line from a dean of Stanford, which is, I mean, you are out here in Silicon Valley, like don't let school get in the way of getting an education.

You know, unfortunately you go to class for 12, 15 hours a week. I was working 18-hour days, you know, in DC. So you have plenty of time to go explore and soak up all that's in Silicon Valley. Speaker A: Were you feeling, how was your ego at that point kind of coming into like, presumably, I mean, one person's reaction to where you were coming from would've been like, I can do anything. I just literally work for the most important person in the world. Did you have a feeling of that? Were you more like, oh, I actually, I don't know anything about the business world?

Speaker B: I was the personal aide to the president. I don't know that I had like the I could do anything kind of thing. I had the probably a little fear of there's a big world out there and I don't think I want to stay in the world that actually I'm pretty well suited for. After that experience, I want to do something else. I want it to be big and bold. I think probably what I most loved about the White House that I wanted to take elsewhere was that it was big and bold.

And so I was looking for another stage that had that in it. And I yet, but I didn't yet know exactly what the stage was. And I didn't know what the role would be. Speaker A: Right. Why Stanford? In some sense, it was like very far away from DC, I suppose. Speaker B: It was far away from DC. Many peers had kind of done the, you know, White House to Harvard Business School and kind of maybe more of like an East Coast path. And I think especially for the kid from Alabama, like, you know, people knew Harvard much more than maybe kind of like this out west path that did feel far.

There was probably something of it, it was different. It had like a kind of less known aspect to where I grew up. It felt to stretch me a little more differently. I think Harvard's an amazing place and I have great relationships from, people there, but it felt more that Stanford was different. And in some ways, it just, when I went out there, I'm like, this feels right. And wasn't always good. And maybe not at the time of like acting on the, it just feels right, jump at it. But I'm glad I ultimately made the decision to go there.

It was a, I got there and it was a very uncomfortable pair of pants at first that became my like favorite pair of pants because I, I was much more used to what I would call like East Coast ambition. Yeah, yeah, yeah. And I think of East Coast ambition as I'm on floor 7 and I'm trying to get to floor 57, like the top office. Whereas West Coast ambition felt to me like, I don't even want to be in that building. I want to build my own building. And that was very new to me.

Speaker A: Right. Why Stanford? In some sense, it was like very far away from DC, I suppose. Speaker B: It was far away from DC. Many peers had kind of done the, you know, White House to Harvard Business School and kind of maybe more of like an East Coast path. And I think especially for the kid from Alabama, like, you know, people knew Harvard much more than maybe kind of like this out west path that did feel far. There was probably something of it, it was different. It had like a kind of less known aspect to where I grew up.

It felt to stretch me a little more differently. I think Harvard's an amazing place and I have great relationships from, people there, but it felt more that Stanford was different. And in some ways, it just, when I went out there, I'm like, this feels right. And wasn't always good. And maybe not at the time of like acting on the, it just feels right, jump at it. But I'm glad I ultimately made the decision to go there. It was a, I got there and it was a very uncomfortable pair of pants at first that became my like favorite pair of pants because I, I was much more used to what I would call like East Coast ambition.

Yeah, yeah, yeah. And I think of East Coast ambition as I'm on floor 7 and I'm trying to get to floor 57, like the top office. Whereas West Coast ambition felt to me like, I don't even want to be in that building. I want to build my own building. And that was very new to me. Speaker A: Totally. Speaker B: And within a few months of being at Stanford, I was like, whoa, this is new and different and is stretching me in a neat way. Speaker A: Totally. Speaker B: And within a few months of being at Stanford, I was like, whoa, this is new and different and is stretching me in a neat way.

Speaker A: That's cool. That's a great metaphor. I'm just curious about like anything else about, about the kind of culture of being in that world that has stuck in your mind? Speaker B: Yeah, I mean, I do think like what real risk is when you get out there. I mean, people would say to me from back home or DC, like, oh, you're at Stanford, you know, all those startups, like, have you been to Google yet? And like, to them, Google was a startup, you know, at that point it was like already a public company.

It felt like, you know, kind of, And out there, you know, people are like, Google's like kind of like, I mean, great company. It's like, oh, it's the empire. Like a startup is, you know, two guys in the garage working, you know, on Red Bull and Cheerios and like building the thing and seeing that normalized. I had never seen startups in that way. And that kind of behavior, you know, it's pretty cool to be on your third startup and two have failed. And so like, that's not a failure out west.

Totally. Speaker A: Yeah, at least DC, ever. Speaker B: That was a total new thing. I mean, even in New York, it feels like, like to be a failed hedge fund manager isn't a particularly champion thing. Speaker A: Right. What was, what drew you or how did you kind of end up falling into the Palantir situation and what was unique or special about those guys? Speaker B: Yeah, I had a classmate. We became friends, a guy named Steve Laughlin, who's now an Accel partner. He started a company called RelateIQ after business school, and I think he heard my story I wasn't really talking a lot about the White House when I got to Stanford, but he said like, there's some guys I think you would enjoy meeting.

And this was in a month or so of getting out to Stanford. And we had a dinner with Joe Lonsdale and Sham Sonkar. And I was like, man, I don't want to have anything to do with like, you know, walking government software through government. That's not interesting to me. Speaker A: Right. What was, what drew you or how did you kind of end up falling into the Palantir situation and what was unique or special about those guys? Speaker B: Yeah, I had a classmate. We became friends, a guy named Steve Laughlin, who's now an Accel partner.

He started a company called RelateIQ after business school, and I think he heard my story I wasn't really talking a lot about the White House when I got to Stanford, but he said like, there's some guys I think you would enjoy meeting. And this was in a month or so of getting out to Stanford. And we had a dinner with Joe Lonsdale and Sham Sonkar. And I was like, man, I don't want to have anything to do with like, you know, walking government software through government. That's not interesting to me.

Speaker A: That'll pigeonhole me almost. Speaker B: That'll pigeonhole— I like, I just left that for the sole reason of coming out here. And they said, "Well, come by the headquarters. Let us tell you what we're doing." And then they said, "Will you map DC for us?" And I was like, "Guys, I may be the best person to do this within like a half a mile radius of Palo Alto, but I'm not actually the best person. I've got a bunch of friends that probably would love to do this for you."

So I introduced them to some people in DC that I thought could help, national security, congressional strategists, kind of lobbyist. And I think I forgot about it for a few months and I, I think I ran into Sham somewhere in Palo Alto and he's like, Jared, those were incredibly helpful people. Like, you've gotta come, let us tell you more about what we do and maybe there's something you could be helpful on. So I said, okay, like, and I went there and it's right in downtown Palo Alto, the headquarters of Palantir were at the time.

And they were telling me not only more what they were doing in government and national security, but early days of some private sector work. And I was like, this is pretty interesting. And the timing was interesting 'cause all the Bush administration people have actually gone off into the private sector and they were now in big banks or pharmaceutical companies or different companies. And I was like, well, maybe we could just go do kind of a, here's what we do, is this interesting to you? And it seems so obvious now, but you know, the idea of a, upstart data analytics, like that was not obvious.

And it kind of got going and Cham said, you know, we really should give you like a consulting contract. I was like, I don't need that. He's like, you know, you can get stock options. And I was like, stock options? Like we didn't even have bonuses in government, let alone like equity. So I didn't really know. I mean, now I'm glad I took the stock options, but, and it was really neat because it was, certainly like an engineering culture at its core. And that, that was totally new to me. I mean, I had not been around that world at all, and I certainly hadn't been around the like, this is messy and it doesn't work perfectly well.

Like I had, there had been one government software project in my world at the White House, and it was like, you know, 17 months of contractor and all this kind of stuff. And Palantir building this stuff in days. Kind of stuff. Speaker A: Was there a— was an element of like, this is like, how credible did you think— like, Thiel was involved, but maybe certainly not as high profile as he is now. Like, was there— were you just kind of like, this is just like, I don't know, they're startups, might as well help?

Speaker B: Like, it was— it was really interesting because we had— we were making some interesting progress and we would go to these banks and I'd teed up some conversations and then the banks And this was, we were doing some interesting work in the mortgage crisis times of helping Bank of America and JP Morgan work through, I mean, they had gotten into those banks, Palantir had, through security, 'cause that's what they were known for. But security was a much smaller problem than their mortgage book. And if we could help with work on that, and, you know, I remember we went down to LA for a meeting with, I think it was Countrywide, which Bank of America owned.

And it was some engineers that I was friends with and Sham and Karp, and then Michael Ovitz showed up on his way in, as always, you know. And I'm like, and Michael Ovitz is someone I admired since I was a kid. And so I was like, whoa, like, what is going on here? And but I, it was, it was a little difficult for me because I didn't know how to assess, right? Speaker A: You didn't have a bar. Speaker B: I didn't have a bar, right? I thought the people, the people were incredibly sharp.

There was a mission alignment, but it was also, I'm kind of like, am I selling or advocating for software? And like, is this stuff work? And You know, I think the messiness of it is more a feature of Silicon Valley often than I was— that was new for me to not have it be perfect day one. Speaker A: Totally. I suspect also very useful, kind of like almost like crash course on just a bunch of things that would be going to be useful for like understanding this world. We kind of skipped over it, but you, I believe you went to Harvard orientation, as I understand it, and you met somebody.

Despite not going— Speaker B: That's true. I went to what is called analytics at Harvard, which is the pre-class for like non-finance people. And so they get you up the curve with— Speaker A: Oh wow. Oh, so it's almost like a bootcamp. Speaker B: It's a bootcamp. And I go to analytics and I think there was 4 or 5 sections, which is about 100 people. And you're assigned to a section, one of those 5 classrooms. And you have an assigned seat. And I get to the section and I turned to the guy next to me and I said, "Hey, I'm Jared Weinstein."

And he said, "Hey, I'm Josh Kushner." And he said, "What's your story?" And I said, "What's your story?" And, you know, over a week he became my buddy, my, you know, my kind of like friend at analytics. And at the end, he may have taken it a little personally. I said like, "I like you, you're great, but I'm gonna go to Stanford." And it was like, And I think, you know, he had been a quick career in banking a year or two at Goldman and then had come to business school and I was coming for government.

I think we connected. I think we were both big dreamers a little bit. I mean, I think there, I could see his ambition at an early age. I think he had seen my experience. You know, there could have been something. I mean, we'd both come from, you know, like Jewish immigrant families, different stories. But also just like we liked each other a little bit. And, but I said like, let's, I'm gonna go to Stanford, you know, we'll keep in touch. And I had no idea what, I mean, he wasn't really doing venture investing at the time.

And we kind of, we were super young, right? Speaker A: Like he was like 24. Speaker B: He was 24. He was 24. And I was— Speaker A: In some sense you were both kind of slightly abnormal in that you hadn't really worked in a real environment. And he, like, Are you saying the White House wasn't a real environment? In some sense, yes. Like, it wasn't normal, standard. Yeah, the president doesn't do anything. Did you guys stay in touch initially? Speaker B: We did kind of texting. And then there was a totally serendipitous moment over the Christmas break or holiday break of that first year.

I think I texted him, how was your year? How was your semester? Great. I'm in Miami. I'm in Miami. We happened to be that night at the same restaurant with our families, which was a weird fate here. So, so weird. And we kind of, hey, how you doing? And I think the next summer between our two years, I came to New York for his 25th birthday and it was a paintball tournament. A lot of his friends that I still see, Chris Pack was there, like 25 years old. I mean, like none of this stuff was on the horizon, right?

And second year of business school, probably halfway through, we were— we had— we did stay in touch and we had, I think, brunch in New York. And he said, what are you thinking about doing after school? And I had done a private equity job. I had thought about— I'd been doing a little bit of the Palantir stuff. I had almost gone to kind of do a like a COO track at a hedge fund at Viking Global. And I was like, I was interested, but I didn't know. And we were kind of talking and he said, you know, I'm thinking about building a venture capital firm.

Would you ever wanna partner with me and do that? And I was like, you know, he's had a year of investment banking experience. I've had 7 years of government. I'm like, of course we should start a venture capital firm. That's so obvious. But you know, he, he had some good reasons for doing it. He made a really compelling case of the opportunity to build a firm in New York. We talked about how we complemented each other with experience. And, you know, I think maybe we didn't have any business starting a venture capital firm, but I don't think that is really the bar.

It's like we wanted to do it and we were ambitious and excited about doing it and passionate about doing it. And we stayed in touch over the next number of months. And he was talking about raising kind of this first institutional fund and, um, and, and ultimately said this would be an exciting thing to do. Speaker A: Sounds like you and Josh knew each other relatively well, but like not that well. What, what was special to you about him? And what do you think he knew other people at Harvard— like, obviously there was— you had some credibility, or, or maybe a ton of credibility in a different world given your past experience, but like What do you think it was value-wise or competence or ability-wise that allowed you to— you guys hadn't worked together.

Like, why, why was that the draw? Speaker B: Yeah, well, I think that I was really drawn to Josh's curiosity. I mean, he talked a lot about why there was an opportunity to do a New York-based early-stage venture capital firm. His excitement of, you know, Josh would talk about like, this is the most change since the Industrial Revolution. And it was like, this is exciting. And he had made some early angel investments that were companies that you started to know about. And then you just think of the concept of a venture capital firm, which is, wow, we are gonna go meet all day with people who are optimistic, ambitious, you think they can change the world, and you, get to help them do that, not only with capital, but with advice and support.

And that spoke to me. And we started to have LP conversations and that looked like that was gonna work out. And so I think I saw, you know, that he was, could set such a big ambition. He could bring other people along. He, had other people. Chris was thinking about joining. Will Gabrick, who's incredibly sharp, was joining. And so there was something— both the excitement of it, the unknown of it was exciting to me. What he saw in me, you have to ask him. I think he saw someone that was, you know, understood from the White House experience, the hard work, the trust, the Managing, juggling tons of balls, the ability to like build a real organization, which I'm so grateful we found each other and decided to do it.

Speaker A: I think, I don't know how old Will is, but it was like, those guys were kind of kids. Like, was there an element of like, oh my gosh, am I doing, am I getting in here with the Rugrats? I mean, obviously you, not like you were, I think you were probably 30. Mm-hmm. Or were there other people in your life, like, who were like, this is what you're going to go do? Speaker B: Yeah, I think there were like, oh, that sounds cute. Start your own little venture capital firm.

Speaker A: Also in New York where there's New York venture capital firms. Speaker B: Yeah, I think there was a little of that. I think I ultimately had to, you know, trust my instincts. I took some time to think about it. And Palantir was interesting. And I did stay involved with them for a number of years, but Thrive was exciting and it was fast. I mean, you know, it was very different obviously than the White House, but between Chris and Will and Josh, I mean, I think all 4 of us, it's like, wow, this is a committed, smart, driven group of people.

Let's see where this can go. Speaker A: It's just, it's interesting on the theme of risk because in in some sense you could say that the White House is like the highest— and I realize like for a lot of reasons different, but like in some sense the highest pedigree thing you could imagine doing. Um, or at the very least it is like consensusly like a place to be. And this was like the exact opposite. Speaker B: Yeah, it, it was at the time. I mean, and certainly we— our brand was below the radar for a long time too.

Speaker A: Um, but you, you didn't have any like, um, there's a thing of like, after you've had a little bit of success in your career, there's a little bit of like scarcity, I think, that can be tempting to have, which is just like, wow, I don't really want to climb down from this local maximum, like, correct? And I gotta parlay this thing into the next thing lest I fall. And somehow you— and granted, it wasn't a straight line, but like, and you had gone to business school and there's Palantir, but like, that was in some sense from the outside looking in, super, super risky, or at the very least taking a huge step down to try something.

Speaker B: Yeah, it, it was at the time. I mean, and certainly we— our brand was below the radar for a long time too. Speaker A: Um, but you, you didn't have any like, um, there's a thing of like, after you've had a little bit of success in your career, there's a little bit of like scarcity, I think, that can be tempting to have, which is just like, wow, I don't really want to climb down from this local maximum, like, correct? And I gotta parlay this thing into the next thing lest I fall.

And somehow you— and granted, it wasn't a straight line, but like, and you had gone to business school and there's Palantir, but like, that was in some sense from the outside looking in, super, super risky, or at the very least taking a huge step down to try something. Speaker B: It felt like a different step, not a step down. Yeah. It felt, I mean, I do, I remember thinking, saying things like, gosh, I, in some ways I hit a grand slam with the White House. And my biggest fear is, I don't know what the next it could be, which was not knowing was scary.

I think that Thrive I saw the potential in it. I mean, years in, we used to say like, can you believe we got here? Or some people would say like, can you believe this thing that was like so small when y'all started? And in no way, like, it's like, yes, we wanted to build this. Like, did we have any business doing it? No. Did it take now 15 years? Yes. But at least we were aiming to do something really great. And that was inspiring and worth trying. Speaker A: And do you know what you're aiming at?

Like, was there a reference point? Would you guys like know about Sequoia Capital or whatever? And you were— Speaker B: Yes, I think. And there were people, you know, there was Tiger Global that what they had built was pretty inspiring in the kind of 2010 times. You know, I think where— I think what one of the things we maybe got right was that we balanced ambition and doing something different with a ton of curiosity and admiration for those who had done it excellently, excellently before us. And so I was, I mean, I had come from zero like finance world and, and the only finance adjacency experience that had been at the White House in 2008 when it felt like, you know, Wall Street was burning down, you know, everything.

And so it was a little bit of skeptical curiosity as I dove into the world and started building Thrive, I was like a student of what people had done. And I would go and ask people if I could sit in on their Monday meetings or if, and the good thing was we were not a threat to anyone at the time. And we were also curious and wanted to partner and maybe write a small check along a Sequoia or Tiger. And I'm really grateful that so many people, you know, supported us along the way and let me learn from them.

And really also to Josh's credit, it was that it is good to know those things and we can do things different. And I think we balanced out those dynamics of the firm really well. Speaker A: Yeah, it takes a certain kind of conviction and self-knowledge to like know where to toe that line. Why was New York important, being in New York? Speaker B: I think that, That was more of Josh believing that it was a market to start in. I think he knew the market. There was, and Josh has seen a lot of things early and made good bets.

And I think there was a feeling that there's this emerging ecosystem. And it was also exciting to see, you know, back when software was more of a category versus what it is now, there were these kind of, traditional industries getting enabled by software. There was entertainment, there was fashion, there was healthcare when we started Oscar. There was just, and so like, I think our core competency was perhaps to be a like interesting way of thinking about enabling these traditional industries. And that was a, certainly for a while, that was a theme that Thrive very much leaned into.

Speaker A: Yeah, yeah. Aside from maybe a couple of things you just said and, that group, which obviously I think in hindsight was quite special. Is there anything else you guys did, maybe not quite right at the beginning, but early on, structurally, culturally, fund setup, LP, like anything that you think was really in hindsight, like really, really important, even if it wasn't completely deliberate? Speaker B: I think there were a number of things. I One, no one outworked Josh or me. So the two top leaders were not advancing their career and thus kind of sitting back and letting other people do the work.

And I think that was setting that, um, goal, setting that example was really important. Um, I think I refused to ever use the word back office at Thrive. I never understood that as like a finance term, that there's like an investing team or, and then there's a back office. It seems so demeaning to me. Speaker B: I think there were a number of things. I One, no one outworked Josh or me. So the two top leaders were not advancing their career and thus kind of sitting back and letting other people do the work.

And I think that was setting that, um, goal, setting that example was really important. Um, I think I refused to ever use the word back office at Thrive. I never understood that as like a finance term, that there's like an investing team or, and then there's a back office. It seems so demeaning to me. Speaker A: Mm-hmm. Speaker B: And at the White House, we didn't have like the important people in the back office. Like we needed excellence. And so I wanted us to have the best investors, absolutely. But I wanted the best general counsel and I wanted the best CFO and I wanted the best receptionist and I think bringing that intentionality to it, both of how we find great talent, but also at like a one team orientation.

Speaker A: Yeah. Speaker B: Was super important. I wanted the assistants, the executive assistants in the room as much as possible in the investment discussions. Not 'cause they would advance the discussion, but that they would then have better context of what we did and they could show up more. I mean, I think we had, you know, great custodial staff and, wonderful man named Ramon who made our office great. And you could say there's that great NASA story of like President Kennedy walking through the halls of NASA and he runs into a janitor and the guy asked him, "What's he doing here?"

And the janitor says like, "I'm working to put a man on the moon." It's like everyone plays a role in the mission. And I wanted that kind of culture there. I think that, I think Josh also always asked the kind of like, Why do we have to do it this way? Like, Josh was always good at questioning things and I think, and also open to the answer of, well, this is why. Speaker A: Yeah, yeah. Speaker B: And I think he trusted that I would drive that forward or also like, let's think differently about things.

Speaker A: One of the things that maybe I alluded to earlier and that certainly comes up when you talk to some people about you is your ability to work under pressure. I'm curious what it was like to go into another really high-stakes environment, maybe post-business school, but also like maybe like, was it just that any crisis or stakes just felt tame compared to what you'd done before? It's just, I think riding on that forever. Speaker B: I think there, you know, there's some of our, you know, Thrive colleagues that would say, gosh, you know, like you got to see crisis Jared, crisis management Jared.

And I'm just like, like, is, you know, is this person leaving? You know, when Will left for Stripe, like, is this really a crisis? Like, doesn't feel like a crisis based on, you know, seeing what I saw at the White House. It's something different and unexpected that you have to manage. Yes. But going into kind of like panic mode never felt like the right strategy to effectively solve it. Or, you know, I don't know, something happens with a company or an LP. Of just, okay, let's get grounded in what actually is going on here and what's the next step and the step after that.

And the sun will come up tomorrow and let's go do something. And kind of like a little bit of like self-trust of, hey, we got here and things will, like, let's get back to our values a little bit. Let's get back to, you know, it's never as bad as it looks. And maybe sometimes I'm never as good as it looks either, and I try to stay level-headed. Speaker A: Yeah. Speaker B: But I'm glad my colleagues enjoyed seeing me in that. Speaker A: It's funny, it's almost like when you've experienced a certain kind of pain, like other pain, but you only, like everyone's, the worst pain anyone's experienced to them is the worst possible.

It's all relative. Speaker B: Yeah, I mean, when I got a call from the Situation Room in like 2000, I don't know, I was 6 or 7 and they said, you know, "Can you track down the chief of staff? Like the vice president has shot somebody on that like hunting trip." And I was like, "Okay, that feels like something that is important to manage and to stay calm." And so some of the Thrive stuff felt not really like— Speaker A: When it comes to any kind of time-based intense period, Do you have any advice on just like how to think about the— assuming you can sort of tolerate— like, I think what you were saying earlier about just like, okay, we've gotten here before, whatever, self-trust, confidence.

What about the sort of tension between collecting information and seeing the room and seeing the kind of chips on the board and speed of action? Like, how do you calibrate that? Obviously depends so much on the situation. Speaker B: So much on the situation. And I think humans are capable of a lot of things and we probably don't appreciate that. We probably like think it's, and it can be paralyzing and stuff like that, but you have to move forward and you probably oftentimes have more information than you realize to take the action.

And I'm probably guilty of that too in a number of cases. I think at times I try to capture all the information. And oftentimes when I look back, like the initial, you could have acted, was like, you know, combination of that and your instinct, you could have acted. Speaker B: So much on the situation. And I think humans are capable of a lot of things and we probably don't appreciate that. We probably like think it's, and it can be paralyzing and stuff like that, but you have to move forward and you probably oftentimes have more information than you realize to take the action.

And I'm probably guilty of that too in a number of cases. I think at times I try to capture all the information. And oftentimes when I look back, like the initial, you could have acted, was like, you know, combination of that and your instinct, you could have acted. Speaker A: Yeah. Yeah. How important was, again, a little bit of a hazy word, but how important was like vision over the course of the period of building Thrive and at what points did it like, was it something that was pretty incremental? Was it something that kind of like had slugs of periods of time and there was a first era and a second era?

Speaker B: Yeah, I think vision, I mean, I think it's in some ways it's never changed, which is to be an exceptional, not just a great, but like be an exceptional firm for the time period that we're in business and around like, and go be a part of the most transformative companies. It took us a while to name it in that way. I think it's now expressed as, you know, be the most impactful partner to the most transformative companies or some version of that. But that whether we could articulate it or not, it felt that that would have been consistently what we were aspiring to do.

Now, in the early days, could you have gotten into the best companies? Not always. Could you have been the most impactful partner? Not yet. But we were looking toward that. And over time, you know, the industries that were most interesting changed and the scale of the ability to invest changed. But I think that's always been the orientation of the firm. And I think in a good way, the firm has been stubborn on that vision. And that's, that's one of the takeaways that I have from the Thrive Experience is, um, for an organization and for individuals, say, stay super stubborn on your vision.

It is, it's your vision, it's your life. Don't live someone else's dream or vision. Like, live and like own and be selfish about your vision, period. And the other thing, and I think people get this wrong, founders get this wrong, is like don't be stubborn on your strategy. Be flexible and nimble and like, you know, and adapt. And I think Thrive was also, we were very good at adapting. And certainly, I mean, think of all the founders who start with something and they want to operate in a certain way, You know, the initial product wedge doesn't make sense or the go-to-market strategy doesn't make sense, but that's where adaptability and flexibility really need to exist.

Speaker A: Right, right, right. What made, what makes, made, makes, 'cause I think it seems to broadly still be true today, that place so good at particularly identifying talent early? Speaker B: I think it's a great question. In some ways, I wish it were more scientific, 'cause then it would feel like something more— Speaker A: But it does seem repeatable. Speaker B: It has been repeatable. I think that we maybe didn't overcomplicate it. There were things that it was, you know, who are your smartest friends? Go ask them who their smartest friends are and go spend time with those people and see if they are values fit, for the firm.

I think it is, yes, intelligence matters, but work ethic is a real thing at Thrive. And you wanted to see people who demonstrated that. I think there's something, you know, I remember talking to a Sequoia partner one day about, about talent and the framing was something like, like, look at their past career, like, people will explain away things, but like, did they make good decisions? Like, did they choose the right place to go? Like, have they, you know, have they won before in sports? Have they? And, you know, you can make a bunch of reasons why things didn't go someone's way, but there's something about like, you know, they, in their situation, they made the right outcome happened.

And I think there was a lot about that. I think there was a, this orientation of like nothing's given to you and you've gotta make it happen or you've gotta create it. And I think that's very much like the immigrant mentality aspect of Thrive. We used to talk about like the biggest fear would be the person who's like joins because Thrive's made it versus the one who, you know, kind of this Thrive always had more of the, like, we wanna storm the castle, not be the castle orientation. Speaker A: That's going to be an interesting challenge for them over the next decade.

Speaker B: I'm long, long the firm. Speaker A: From a leadership standpoint, how did you go about maintaining that kind of like incredible rigor and high bar while bringing in this kind of warmth and humanity that we talked about earlier, maybe even camaraderie? Speaker B: Yeah, I mean, to me, I don't think we were ever going to lower our bar. And I think the risk was more that we lowered our humanity, lowered our camaraderie and compassion. And I just believe that, you know, Thrive, it's not great if a place is a, you know, kindness is honesty.

Kindness is pushing someone. Kindness isn't like letting people get away with stuff. And I think we were, I thought we would get the best out of people if we were, you know, one team aligned of around the mission. And if I could play a role in helping everyone at the firm be the best version of their, theirself, if we had chosen the right people, then that would lead to good outcomes. I think maybe there was a little bit of Andy Card, White House Chief of Staff role of like, my job is to make everyone else successful, like a Shane Battier kind of orientation there.

And I think we did a good job with that. Speaker A: What was the Monday question? Speaker B: The Monday question was in an attempt to, you know, I don't know, take ourselves seriously, take our job seriously, but not always ourselves seriously to that point on like our humanity. When COVID started and we were all on Zoom and in disparate places and it was, became a little bit, I don't know, monotonous and, you know, kind of just giving updates and it was exhausting. Speaker A: What was the Monday question? Speaker B: The Monday question was in an attempt to, you know, I don't know, take ourselves seriously, take our job seriously, but not always ourselves seriously to that point on like our humanity.

When COVID started and we were all on Zoom and in disparate places and it was, became a little bit, I don't know, monotonous and, you know, kind of just giving updates and it was exhausting. Speaker A: Very transactional, mostly. Speaker B: Very transactional. And it's like you miss being in the office with everybody. My thing was, let's ask a different question of the whole team to start off the Monday. And it was everything from, I mean, I think I even used years ago the Patrick O'Shaughnessy question, what's the kindest thing anyone at Thrive's ever done for you?

I asked, you know, like, what's your favorite pizza topping? I mean, there was silliness, there was funniness, but it was about like, let's just stay in the fact that we are people who like each other and need to know each other. And we're not in each other's lives as much as we had been when we were all in New York. And, you know, when we were 40, 50 people at that point in time. Speaker A: I was gonna say, it was like 50 people on a Zoom. Speaker B: I'm grateful that people leaned in.

There was like at times some eye rolling, but I think even for the eye rollers, was like, God, that was like great. And you know, we used to ask people on their first day, I think this question has remained despite Josh fighting the question, you know, what's your favorite Girl Scout cookie? Like a ridiculous question, but like, come on, you know, like let's keep things light. And then there were other firms that would be like, I heard if you ask this Monday question, it feels like a great way to like keep the team engaged.

I'm like, should I trademark the Monday question? Speaker B: I'm grateful that people leaned in. There was like at times some eye rolling, but I think even for the eye rollers, was like, God, that was like great. And you know, we used to ask people on their first day, I think this question has remained despite Josh fighting the question, you know, what's your favorite Girl Scout cookie? Like a ridiculous question, but like, come on, you know, like let's keep things light. And then there were other firms that would be like, I heard if you ask this Monday question, it feels like a great way to like keep the team engaged.

I'm like, should I trademark the Monday question? Speaker A: The little things. Speaker B: Little things. Speaker A: In what ways did you guys use— and I guess, I guess, I mean, this is leaders primarily, meaning you and Josh, like, in what ways was some kind of healthy competition amongst the young stable of star investors? Like, was that a useful— like, what is the balance there? Venture capital is a weird thing in that it's some— obviously Thrive as well as many other great firms talk about how it's one firm, it's one team.

In some ways it's a little bit like a swim team though, in that like there is a— Speaker B: I tried to fight that. Okay. I did never wanted us to apply for the Midas List, for example, because I thought that we had all worked on deals and maybe so-and-so had sourced it and someone had supported on underwriting and someone else had helped win it and You know, we were always meeting and discussing deals, and it wasn't just in the Monday meeting. We were getting on the phone at midnight and we were, you know, flying places as a group to go sell ourselves to people.

And so I do think there was that. I don't, you know, we didn't really focus on, I think it was more intuitive around performance, and we wanted everyone to feel like you have your path at Thrive. And everyone has come from different backgrounds and they all have their trajectory and their path. Do not compare yourself to someone else. Now, there's a— these are competitive, ambitious young people. They will self-compare. You don't have to encourage them to do that. I think the people that succeeded at Thrive over the long term took the long view and their goal wasn't to do a deal you know, in the first 6 months of being at the firm.

It was, how do I learn what the strategy and the orientation and the, the way that this firm shows up? How do I learn how the more senior people underwrite and win deals, how they support companies? And if I can take my own intelligence and style and mold it with and meld it with that, I can ultimately then get my sea legs and go off and and do my thing. And you think about people like, you know, Kareem and Miles and Vince and Phillip, like they started and they were willing to say like, this is a great place for me to be.

I've got a lot to learn. I've got a lot to bring also. And I'm gonna play the long game. And I mean, look at how successful those guys have been. Speaker A: And all in pretty different, like individuated kind of flavors. Speaker B: Totally different flavors. Speaker A: Right, right, right. As a, again, very human-oriented, people-oriented person, I'm curious what your lens broadly is on great founders and great companies and to what extent you can kind of understand or even underwrite an investment by understanding the people inside of a situation.

Speaker B: You know, as you said, like every investor has like a different flavor. And I, what I loved about my investing time at Thrive was the founders I got to back. And I think there's a lot of people say, you know, you need to know you need 10 years before you know if you're any good at it or what you're good at. And as the firm scaled to more growth deals, I find myself also gravitated still towards early founders and being that first call, first partner. As I said earlier, I love listening.

And I think in the early days, you know, be careful not to like dictate to a founder exactly what they should do and really listen and put yourself in that seat. There's a lot of great people who start businesses that don't work out. So I don't think it's it's only a founder thing. They have to make the right decisions on their business and their product. But a lot of mistakes we made at Thrive, all of us were probably choosing the wrong setup for a founder, you know, like, and ultimately ideas are amazing.

I love inspiring ideas and concepts and visions, but it's leaders who have to make them a reality. And thinking about, people talk about product-market fit. There's also, you know, founder-opportunity fit in many ways. And thinking about, is this the right founder? And there's so many different kinds of founders out there. I mean, there are consistent things, the tenacity, the ability to like, I think, learn and growth-oriented aspects, but then it's very dependent on the opportunity. Speaker A: There is a thread that I think is quite obliquical applicable to your time at Thrive, but I think broadly applies and certainly is relevant to the work you do today too, which is just— I mentioned it briefly earlier, like being an amplifier, also a confidant, also an advisor, like this role that you continue to find yourself in.

I think a part of it that I want to get to is actually like the person-situation-fit, the self-knowledge that actually allows for somebody to flourish. But I think one place to start that came up as I was talking to people was the way that you seem to enter situations with a great amount of humility and not in this sort of like, whatever, woe is me or I'm lower, but specifically like, what do I not know about this? What do I, what do I, what like knowledge, what context do I have to gain before I'm ready to kind of bring a point of view forward?

And I'm curious what, to the extent you've identified that, like where you think it comes from. Is it a White House thing? Is it an Alabama thing? Is it a faith thing? Is it a family thing? Speaker B: That's a really good question. I, you know, maybe could be better served by having kind of blind confidence that I just know the path and just you'll figure it out. I feel like, I'm rarely the expert on anything. My career has been very horizontal across different things. And so maybe I bring a similar skill or orientation or disposition as a leader to those things, but I've gotta learn the context of the place.

And also like everyone has their own reality, even within Thrive, you know, I deserve this much compensation or this deal is right and you don't know. And so you've gotta, pull out and kind of try to drive for the best conversation and be curious. I mean, I remember when early days of Thrive, when Chris called me and said we had passed on Twitch and he said, we're making a mistake. And I said, well, you've done a really poor job of articulating why this is interesting and let's talk about it because I'm not hearing it.

And so I'm not saying it's uninteresting. I actually believe in your conviction, but the rest of the team isn't deep in the space. And, and, and, and, you know, I think by maybe creating a container and a place where he could better articulate it for me allowed him to then better articulate it and went back to the team and ultimately did the deal. Speaker A: Hmm. Maybe a similar question around, uh, a service orientation and kind of just broad-based generosity. It's a hard question to answer, but I'm curious if there have been influences for you in your life that that you can trace that back to?

Speaker B: My hero is my grandfather, and he was a World War II veteran who came back and built a business here in Birmingham and then served his community in different ways. He was a stoic man. Maybe I take some of that from him, but he was a really big heart. And people would over the years tell me like, I loved your granddad. And like, he was always so kind to me. You know, I always experienced him a little bit as like kind of the like silent, but I think people, he was maybe magnetic in a really inspiring way.

My parents were certainly, I think, you know, philanthropic in a certain way. And then as I said, you know, working for President Bush, you had a huge heart and I see the best in people. I don't wanna confuse that with, you know, that people, that I'm too naive to people's motivations or stuff, but I do see the best in people and I hope for the best in people. And I think through all those experiences, sometimes I can look at a situation and see where someone is in their own way and talk them through to a better place.

Speaker A: Right, right. One of the things that continues to come up with anyone who has, I think, benefited from you as an advisor of any kind, is that you are deeply empathetic and understanding and not soft. So it's just this like unique tension. Chris Pack put it as like he cares with the right weighting about the people and the outcomes. And there are people who kind of swing to one direction or another, but that balance being really effective. Another way of putting this maybe is like Jared, like he does— most people hedge because they're like concerned about how you're going to react.

Isn't like you don't hedge, but you're on the person's team. Speaker A: Right, right. One of the things that continues to come up with anyone who has, I think, benefited from you as an advisor of any kind, is that you are deeply empathetic and understanding and not soft. So it's just this like unique tension. Chris Pack put it as like he cares with the right weighting about the people and the outcomes. And there are people who kind of swing to one direction or another, but that balance being really effective. Another way of putting this maybe is like Jared, like he does— most people hedge because they're like concerned about how you're going to react.

Isn't like you don't hedge, but you're on the person's team. Speaker B: Yeah, well, I think I'm more interested in being effective than being right. I think, and I've certainly not always been effective. I think that as an empathetic person and a good listener, I think I have a, that's a good combination to understand where the other person is coming from. And I find myself oftentimes setting the table a little bit for conversations that maybe have more of that tough love and directness. I think I've grown in the ability to be on the nail directness, but kind of being on the nail but not being effective feels wasted energy.

And sometimes I have to be, it's like my instinct on what the right answer is, that's almost the easy part sometimes. How do I, how do I take this other person like on a journey to that point? I probably don't get it right that as much as I would like, but that's, I think, the orientation. Speaker A: Yeah, your advice, all good advice is shaped to the receiver in a way that maybe another element of what you were just saying, which is sort of like understanding that actually the answer may not be as important as delivery is like seemingly you are good at not projecting yourself into the situation as you are.

You're just kind of like giving it like a clean inspection or something. It's weird though, 'cause maybe the attention I was speaking about earlier, it's like a combination of being incredibly personal and somewhat impersonal, like having distance. Speaker B: Well, I think, you know, especially now as I'm sometimes more in these advisor seats, I'm able to kind of be a little more, I deeply care about them, but I'm in some ways dispassionate to the situation a little bit and able to give clearer advice. Yeah, yeah, yeah. Speaker A: It seems like also you're, you're good at keeping people accountable to themselves in the sense that you're not pushing them in a direction.

You're helping them not get in their own way on the way they actually already want to go. Speaker B: Yeah, I mean, one of One of the kindest things that when I stepped back from Thrive, Josh called me, you know, and said, "We have something for you." And he had put together a book of letters from everyone on the team about, I don't know, the role I'd played or where I'd been most helpful. And it was neat 'cause there were individual stories, but a thread to this topic that I don't know that I fully appreciated it until I got the book was, gosh, Jared, you know, sat on the same side of the table as me, even if he was technically on the other side, even if he was my manager or we were in a disagreement.

I kind of always felt like he put himself on my side of the table and tried to kind of, you know, at a whole human level, get the best of the situation and best of the outcome. And that was really nice to hear. And it was also interesting to digest that and reflect on it and see Wow, maybe there's something that you can lean into more. And yeah, that's meant a lot. I'm glad that people benefit from that and find that valuable. Speaker A: There's a, it's not maybe quite this, but it's sort of like a benefit of the doubt or something, or like taking people, it's what you said earlier, it's seeing the best in people and then also saying like, you can be better or something.

Speaker B: Yes. Speaker A: Do you have any advice or thoughts on how most people really struggle with like saying the hard thing or like moving into conflict, in part because it is wrapped up in so many of these emotions? Speaker B: It is really hard, and it's hard when they're wrapped up in the situation or it's not a great environment. There is a it's almost always the right thing. It's almost always, it's almost known by everyone too. And you're just, you're cut, it's like you just get to the other side of it and there's almost this like, it's like everyone's almost glad that it's like come out, even if it's a little shocking.

And it's like, 'cause it's probably the truth and it needs to be said. It's usually not meant personally, but it's important. I think delaying those conversations just breeds worse energy or resentment or things like that. And so it's really valuable to get that stuff out on the table. Speaker A: We talked about it briefly with the founder thing around the kind of founder market fit. You have a, like a packet that you've sent me and I presumably send other people called "When Do I Use My Best Stuff?" Can you talk about why that both literally that specific example, but also the concepts behind it is so important?

And maybe broadly, like, there's a bunch of themes in this kind of wheelhouse of like, authenticity and self-knowledge and alignment or like leaning into your genius. But like, what is inside of that? And why is it so important? Speaker A: We talked about it briefly with the founder thing around the kind of founder market fit. You have a, like a packet that you've sent me and I presumably send other people called "When Do I Use My Best Stuff?" Can you talk about why that both literally that specific example, but also the concepts behind it is so important?

And maybe broadly, like, there's a bunch of themes in this kind of wheelhouse of like, authenticity and self-knowledge and alignment or like leaning into your genius. But like, what is inside of that? And why is it so important? Speaker B: Yeah, well, at the simplest level, I think if all of us are doing whatever the best version of ourselves are, things are going to be, you know, pretty great. And I oftentimes think about, and I'd use in in one-on-ones with people on the team, like, you know, like, Michael Jordan was put on this earth to play basketball.

Now, it was fine that he went and played baseball for 18 months, but we're all really fortunate that Michael Jordan played basketball for as long as he did. And like, what's your basketball? And like, what's your zone of genius? And the best stuff exercise, as you recall, is, you know, kind of over your largely, you know, teenager to adult years, When were you at your best? And you kind of list the categories and then that's interesting, but what's more important is you kind of say, well, what about those things was your best self?

And I actually think what's most interesting is those sub-bullets. And usually those rhyme with each other a lot more oftentimes than the top level. And so you're kind of given this instruction booklet of what aspects of an experience usually bring out the best version of myself. And it can be wide ranging. It can be the kind of people you're with. It can be the, aspect of the project. It can be the function that you were asked to do. And, and I think what I try to push people with, and what I've pushed myself, is not that every decision and every experience you sign up for has to be perfectly the best stuff, but think about how far are you deviating from what this amazing, like, past that says, well, this is your best—

Speaker A: the correlation line or something, you know. Speaker B: And so if— just be careful if you're veering too far off on it. Speaker A: What I like about it too is, at least the example you gave me, it's like some of the examples are literally like stuff when you're like a little kid or like in high school, or, and seemingly quite trivial. I think there are multiple parts of that. One of them mainly just being that we often like forget, we get far, far away from ourselves. But the other part about it that is interesting is it's like, uh, almost inside— maybe I'm misremembering or projecting a little bit, but part of what it felt like inside the questions is like, when do I actually like, like myself?

What am I really proud proud to have been me. Speaker B: Yeah. Speaker A: And it— one of the things I found, and granted it was a unique time in my life when I was doing it, but I found it was a little hard at first to actually do it. Like, it shouldn't be that hard, but like, you— we, we abstract ourselves from these things. Speaker B: Yeah. And I think we oftentimes like want to like examine and diagnose others versus ourselves. And oftentimes the people that we think are causing us friction.

And that's worth doing and understanding, well, why is this setup not working and how can I? But like, come on, like you're, you know, it's self-examination, self-growth. And you know, one of Josh's great lines that I love is, you know, like, if I'm not embarrassed about the person I was 2 years ago, I'm not growing. And like, what an amazing approach to like, I was trying my best and I've worked to get better. And being okay with kind of knowing that you have made mistakes in the past and need to grow from those.

Speaker A: Right. Yeah. I mean, there's also just an element of just, I think a lot of people spend, their reluctance to self-knowing is so strong that they'll just spend their life chasing like what somebody else thinks is good. Speaker B: Well, right. The self-knowing thing is like, well, then you have to do something with it. And almost when you put it on someone else, you're like, well, that's for them to figure out. It's not my responsibility. I've told them. Speaker A: Right. There's a, um, a kind of trio of things that tend to bubble together in, um, very successful people, um, of ego, ambition, and impact.

Um, and those things are almost like— obviously they, they aren't totally at odds, but they can kind of be in tension with each other. And my sense is you've spent a lot of your life being a mirror and supporter and advisor to people with incredible ambition, um, and you're like helping them balance— you're helping amplify them in some ways, you're helping them balance those things in other ways. And I'm curious, like, what, what goes into helping those people see clearly and keep those things? Speaker B: That's like a 6-degree black belt kind of human psychology question.

I, I think it's easy to try to dismiss ego or like fight ego. And I think that's pretty dangerous. I think having a healthy understanding and awareness of your ego is important. I think kind of looking at it and saying like, this is the way you've served me well, this is the way, you know, and it's just a thing and it's a fuel. It's probably more of a dirty fuel than a clean fuel. Speaker A: It's probably a critical one for almost anyone who does anything. Speaker B: But a clean fuel.

I think it, right, it's maybe the fuel to like get you off the launch pad, but like not to continue the like total direct journey. I think ambition is, I don't know, it's kind of a combination of all of it. It feels like it's kind of like what kind of ambition? Is it ambition to build the biggest company? Is it to make the most money? Is it to have the, kind of encompasses almost a lot of it. Impact is this other thing. I think impact is self-defined also. And it kind of comes, a lot of times it comes into people's, comes in when I think maybe they realize that the ego fuel has served its purpose or something.

And maybe a little bit of more secure, orientation that they have, like more like, okay, I'm here, I don't need all this other, I don't need someone else saying I'm great again, or I don't need maybe more money. I like, you know, I'm like, I wanna do something good. Maybe impact also the other side of the coin is like this legacy orientation, which may come back to ego. Speaker A: This is what I mean. I think these things are actually always revolving. It's like a three-body problem. Speaker B: Yeah, and it also can be like a little dizzying to try to tease it all out and separate it.

I think that you probably ultimately get back to like the what is true for me, what is the life I wanna live. I think back to my vision point, like don't live someone else's life. Don't like, I think you start to realize like the popularity or the recognition, like what does that really serve? Ultimately, what do you wanna do with this limited amount of time you have here and who do you wanna surround yourself? What brings out the best version of you? There's probably all of that a little bit in there, but if you kind of simplify it to how do you wanna live the best days possible?

And there's, you know, that's a really fortunate question to get to ask. And I think people need to reckon, not everyone gets to ask themselves that question. And so, So just being in that place to get to think about that is a luxury. Speaker A: This is what I mean. I think these things are actually always revolving. It's like a three-body problem. Speaker B: Yeah, and it also can be like a little dizzying to try to tease it all out and separate it. I think that you probably ultimately get back to like the what is true for me, what is the life I wanna live.

I think back to my vision point, like don't live someone else's life. Don't like, I think you start to realize like the popularity or the recognition, like what does that really serve? Ultimately, what do you wanna do with this limited amount of time you have here and who do you wanna surround yourself? What brings out the best version of you? There's probably all of that a little bit in there, but if you kind of simplify it to how do you wanna live the best days possible? And there's, you know, that's a really fortunate question to get to ask.

And I think people need to reckon, not everyone gets to ask themselves that question. And so, So just being in that place to get to think about that is a luxury. Speaker A: You— one component of this, and I want to talk about the work you're doing now in Birmingham and looking ahead, but the extent to which we use legibility to feed those things. And by the way, legibility can feed ego, it can feed ambition, it can feed impact. You're someone who I think historically tends to lie low. And if not outright be in the shadows.

There's not a lot of R. Weinstein on the internet. I'm grateful you're doing this with me today. Yeah. How do you— in what ways is legibility— and I don't just mean that in the like super public internet, whatever media sense, even just talking about what you're doing. Like there's some people who kind of skew one way and just say like, put your head down and do the thing. And there's people who skew the other way, which is like, like all good, all press is good press. Speaker B: Yep. Speaker A: How have you evolved your view on that?

Speaker B: I think that oftentimes if you want to do, let's call it big stuff, important stuff, like other people need to be on the bus with you. And if you want to go, you know, fast, go alone. You want to go far, go together, that kind of thing. And so if you want to bring other people on the bus, legibility at some level. And that can be in a one-to-one sense, that can be in a, you know, mission statement of a company or an orientation of what we working on.

And ultimately you have outside stakeholders, probably partners, collaborators, funders, the general public. And so I think that I hear you on, there's not a lot about me on the White House, on the, on the, in the public domain, but also like for my 20s, I was at the White House. It's a very legible place. Like people, you know, hey, I'm Jared Weinstein calling from the White House, I need the following. Speaker A: Right, you don't need to explain yourself. Speaker B: You don't need to explain it. And I also know, you know, Thrive, we were, even if we were below the radar for a while, we were intentional that a brand was being built and the relevant people were starting to learn about us.

I didn't feel like that they needed, that the people that needed to know about me knew about me, and that was fine. And I also do think that if you're, if you stick your head in the sand and don't share your work, you may not be as effective because there may be people out there that wanna come collaborate with you or come along. I don't think for me it's an ego thing. I don't think, but I'm like aware it could be. It's ultimately an effectiveness thing. And, you know, I want the work to speak for itself.

And sometimes people need to know about the work. Speaker A: You left Thrive in 2022. Did that feel like a risk? Speaker B: Yes. I mean, it was— someone told me like, people look and think people do like courageous things. And then you talk to the person and they're like, I just like had to do it. It like wasn't courage. It was just the time to do the thing. I mean, as I think you know, and as this conversation says, like, I love Thrive. I am so proud of it. I'm so proud of the people there across all aspects of the firm.

And as I think we talked about, like, I'm an all-in kind of guy. My mom got terminally sick in 2007. 21. And I was down with her a lot. And it became a little harder to become all in, but I think I was still all in. It also totally changes your perspective on a lot of things. There is— has been no bigger champion of Jared Weinstein in this world than Brenda Weinstein. And, you know, she needed a champion. And I was really glad that I was in a place to be a champion for her.

And it's been a— She's in an unfortunately different kind of place. She's not the same kind of bubbly person she used to be, but she's still with us and it's given me this amazing time. But it also was, I was gonna step back from something that I cared a ton about and I'm really proud of in many ways. Thrive, I had so much confidence at that point that we had built something that worked and had amazing people and could carry on and was like doing great things that it was, it was, you know, a little bit easier to like hand it off.

And I had like tons of confidence, like, you know, they were like, you know, who's gonna do this and who's gonna do that? I was like, yeah guys, you're good. Like, you've got this, you know, like everyone can like move on. And so I stayed on some boards and I still take phone calls and help with things and invest in the firm and all of that kind of stuff. But yeah, it felt, I don't know, It felt like the thing to do. And it was once I made the decision and we talked about it, it just, it also felt, it felt right.

It felt okay, like a little bit of the unknown. I mean, I, we talked about should I stay on more of like a venture partner kind of role? And I was like, I don't know, like I just think the right thing is to step back and I will, I mean, everyone, like I will always be a champion and a helper and whatever I can do. And Josh Ash will remain like a close— has remained a close friend. I mean, whereas— and all the people there were close friends. And yeah, I mean, I think when you're operating at that level and involved in everything we were building, it feels a little kind of like, whoa, like you're stepping off the platform and, you know, a little bit like, not what is your— what will your identity be a little bit, but I really trusted that the right thing to do was to step back and to focus at first on my mom and a little bit like, where did I, where would I be drawn to spend time?

And, and I, you know, I'm really happy with it. Speaker A: You've had two very critical, long identity-consuming professional experiences. I helped start a startup and was there for 4 years and leaving felt like it was like my entire life. And so I imagine that is it. How long were you at Thrive? 12 years? Speaker B: And, uh, like 11 to, you know, 11, 11-plus years. Speaker A: That's, uh, it's a whole thing. You, I think, as maybe as, as a prelude to returning to Birmingham, you spent time in 3 very distinct places I referred to earlier:

, Silicon Valley, and then New York. You seem to be a remarkably consistent person, and so I'm curious how you've kind maintain— what you've maintained and to what extent you've remained consistent across moving across these very different worlds. And maybe even like what you think is consistently relevant or valuable as you've gone through those different kind of— you've worn different hats. Speaker B: Yeah. Well, you know, I do think at least in the time I was in all of those different places, they are wildly different places. In many cases, I feel like the same person I've always been.

And I sure hope I've grown and changed and been positively impacted by all those places. I think that, you know, I've been a hard worker since I was a kid. I have been a curious and like friendly and compassionate person since I was a kid. I've been an ambitious person since I was a kid. I've like wanted big things and exciting things and in some ways maybe novelty and difference and trying new things. I mean, DC, it had very much, as we've discussed, a kind of a zero, you know, like the, you know, you get the speech to the podium, the words have to be right.

You were making changes of like, you know, this many people got this kind of government aid and you change it just to make sure he was saying the exact right thing and that his tie was perfect and the schedule It's like almost how high can we get the floor? Not entirely though. Yeah, it's just like, you know, and mistakes are always made, but like it's really about like flawless execution kind of thing and ensuring that machine works. And, you know, Silicon Valley and the time out there was, you know, as I said, like a different pair of pants.

Like, whoa, like this is real risk-taking. This is, you don't have to figure it out and you just have to put one foot in front of the other. Keep going. And, you know, what starts as an idea and a pitch deck and some capital can become a massive enterprise. And it's like, whereas in government, these are institutions that have been around for a really long time. You know, New York was incredible. I love New York. I'm there a lot. I think just the, you know, kind of the boldness and the ambition and the, you know, things are possible and the speed, the creativity.

I'm really glad I lived in DC first. I think like it would've been hard to be in DC after living in New York. And then, and Birmingham is, you know, the fourth place is very different now that I'm here a lot more. Speaker A: What is special about this place? Speaker B: Birmingham, I mean, certainly it's a place that, that kind of my family experienced the American dream. We came over from Europe and down from New York and started a kind of like peddler business that grew into aluminum metal manufacture.

And so it provided a ton for my family. And it also was a place that formed me. And I'm really grateful for what I got to see in it. It's a place where I think family is really important. It's a place that, it's a really interesting city because Birmingham kind of came out of nowhere after the Civil War. It wasn't around. It was an industrial thing that kind of came out and there were some railroads that crossed here and that's why everyone congregated here after the Civil War. And it was on like a tear.

I mean, from like 1870s until kind of 1950s, Birmingham was like the bet as like the next city or the city of the South. There's this fascinating history of like, they actually wanted to put what is now the Atlanta Airport in Birmingham in the 1950s. Wow. And we like pushed in a different direction. Now, unfortunately, in the 1960s, it was a pretty ugly time in Birmingham. And the country was watching that. And I think that has been an identity struggle for Birmingham in many ways since then. And I think it's important, and I understand why people acknowledge that past and think about that past, and yet you have to acknowledge and move forward.

Speaker A: Yeah. Speaker B: And I get a lot of, I'm very interested in cities. Cities are super fascinating to me. I mean, I think maybe not for us who are moving around globally, but for a huge amount of the population, cities are their kind of atomic unit of opportunity, and it's where they have to work and their family and their school and their experiences there. And so, you know, companies are complex and making companies work, but cities are massively more complex. And it's been really interesting. And I think there's a thread since I was kind of younger, going to Duke was really interesting unexpectedly.

I mean, Raleigh-Durham was this place that was maybe not overly dissimilar from Alabama, kind of a rural, place that with Research Triangle and these universities has kind of figured out some things to do. And so I think a lot about how can cities like a Birmingham change? And people sometimes, you know, one, they say that sounds really hard and can you really do it? And then I think about a Detroit where, you know, if you had read an article that said, you know, Amazon was putting an engineering center here and, this, you know, cultural activity is happening in Detroit.

Like 15 years ago, 20 years ago, that's like an Onion article, right? You know, and now it's like reality. So in 15, 20 years, places are changeable. And I think a lot about what tools can I use from the nonprofit space to investing here in companies to real estate to, you know, both like cultural but kind of attitude changes that don't make Birmingham try to be anything that it's not. It's not trying to be Austin, it's just trying to be a better Birmingham. And stay true to your identity, but also move forward toward, you know, making it, you know, the best place possible that it can be.

Speaker A: Before we talk about what maybe can be done looking ahead, as I understand it, you started getting involved here much, much earlier than when you moved back, like almost like 2013 or something, like pretty early into Thrive. And again, maybe there's an element of some kind of civic duty going back to the White House days, but like, what went in? Was it obligation? Was it duty? Was it love? Was it gratefulness? Like, what caused you to start doing that? And how did you, by the way, like, you weren't not busy.

Speaker B: Right. Well, I think I was a few years into Thrive, which was exciting, and Palantir was still going on, and I was like, I was like, I could have been a little subconsciously worried that I was just becoming like a finance guy. I don't know. And I was like, I was, you know, you weren't in government service anymore. And I think maybe back to my granddad as like a business leader that was civic and community focused, I was kind of like, what part of my identity, like there's something thirsting there.

And New York is amazing as we both know, but I think I probably felt like my efforts like a drop in the bucket here and probably like my heart's not here. Right. And I was also looking at a city in Birmingham that, um, I mean, the reality is like growth has been slower here. There, there are things happening, but it also felt like I could take my experiences from DC and Silicon Valley and New York and things I saw, things that people were doing, and almost like geographically arbitrage kind of like the things that were working in those markets and bring them here.

And That started with an education program in 2013. And we called up this education program in San Francisco and said, "I'd like you to come to Birmingham." And it was like, click, you know, like, "We're not coming to Birmingham, Alabama." I was like, you know, kind of, "What do you need to see? What would the goalposts be? Like, if you did hear about these things?" And so for a number of years, as I was in New York, I was kind of playing this like matchmaker where I think I was legible to some of these national places of like, oh, he's like in New York and he's in venture capital.

And so like maybe he understands us and he can help us think about Birmingham. And to people in Birmingham, I was identifying interesting, innovative programs. And I think they were saying, oh, Jared's seeing a wide spectrum of things. Maybe let's support him in bringing them here. Speaker A: When it comes to Cities, as you said earlier, cities are— companies are complicated, cities are much more so. Um, there are companies that are effectively run like dictatorships. Um, in fact, we like often glorify them. Um, you can't run a city or even probably significantly affect a city in a super top-down way.

When it comes to like a theory of change for affecting a place that you care a ton about. Obviously, I think one thing we were talking about the other day was just like how the timescale is very different than, than other problems. But I'm curious, one of the things as we were prepping for this too, you— I had mentioned something about nonprofits and, and you maybe made a comment that like nonprofit is conflated with impact and like I'm tool agnostic. Um, but across these sort of types of things, I, I'd love for you to just talk a little bit about whether it be the infrastructure side, the civic side, the government side, the business side, the cultural and storytelling side.

Like, what have you learned as you've started to— I mean, you've been working on the problem for a long time, but what have you learned as you try to like sink your teeth into it in terms of like what can happen, how long it takes things to happen, how these things kind of fit together? I realize that's a really open-ended question, but yeah, I love it. Speaker B: I mean, I think I think you probably, you know, top-down needs to meet bottoms-up. I think like Singapore is probably an amazing top-down example in many ways, probably maybe some like Middle East cities that have more top-down.

My, let's call it like work on Birmingham 1.0, the first 10 years was, in short, it was going to find these national models in education and early childhood and workforce development. Entrepreneurial support, maybe in coding, I'm like, oh, these work, they have the most efficacy, they're very compelling strategies. And so I'm gonna bring the best strategy here and execute on it. And I think that did have impact. I think like the programs were good, our outcomes were good. I also think that maybe a downstream unexpected example was, or it was an example to others of like, oh, you can go bring things here.

And it was, It was kind of social entrepreneurship in many ways. I think that that was and remains like a compelling part of the theory of change. Speaker B: I mean, I think I think you probably, you know, top-down needs to meet bottoms-up. I think like Singapore is probably an amazing top-down example in many ways, probably maybe some like Middle East cities that have more top-down. My, let's call it like work on Birmingham 1.0, the first 10 years was, in short, it was going to find these national models in education and early childhood and workforce development.

Entrepreneurial support, maybe in coding, I'm like, oh, these work, they have the most efficacy, they're very compelling strategies. And so I'm gonna bring the best strategy here and execute on it. And I think that did have impact. I think like the programs were good, our outcomes were good. I also think that maybe a downstream unexpected example was, or it was an example to others of like, oh, you can go bring things here. And it was, It was kind of social entrepreneurship in many ways. I think that that was and remains like a compelling part of the theory of change.

Speaker A: And those things, to be clear, are like, they don't need to be that tailored to Birmingham as part of it. Speaker B: Well, I think they need to be local. I think anything needs to be localized. I don't think you can cookie cutter— Speaker A: Got it. Speaker B: —everything. There's gradients, but you have to meet the community a little bit where it is and then push the community. And that's what these programs did. But they were largely national models that I was kind of incubating debating the Birmingham version of it.

Continue to do that. Always interested in ways to do more of that. As I started to spend more time down here, I, and I was also doing start, uh, investing and there would be startup founders and there was some real estate projects where I was thinking, okay, this would be neat to have downtown be more dynamic in this way and this kind of thing also that I may see in other markets. Oh gosh, like this thing exists in Brooklyn, it would be fun to have a Birmingham version of it and people would like that.

And also like humans are humans, we kind of all like a similar, largely the same kind of thing. Right, right. As I was down here more, I think I said, okay, Jared, you could keep finding the strategies yourself and bringing them here, but maybe you want to approach it a little differently, which is instead of taking national strategies and bringing them to Birmingham, Why don't you take people in Birmingham who are exhibiting versions of what you see at a kind of founder mode orientation and unleash them? And that's been kind of a new leg of the stool of my work, which is I don't care what you're working on here.

I just care that you're like going for it. And there's great institutions here and there's companies that make sense for some people to work for. But I want to balance that with people who are saying, I want to go off and start this new tech company. I want to start this wind power company. I want to start a food pantry. I want to start a restaurant. I want to start a sports youth league. I don't really care. It's kind of like a bottoms up, let me unlock your potential and support you.

Give it some thrust maybe. Yeah, and kind of like a little bit like, I don't know, A Thousand Flowers Blooming or something of just like more create the conditions for people who show a risk mindset relevant relative to the community. Or, you know, we can say agency and unleash that agency and then support them on the journey as a venture investor would. It's kind of like we invest in a lot of sectors. This is kind of, you know, I don't know, impact venture. Some of them are companies. I invest in a ton of companies down here in a tech sort of way.

I've invested in restaurant groups, I've invested in real estate developments, and I've invested in, nonprofit initiatives. It's kind of— that's when I say tool agnostic. Yeah. Speaker A: Got it. Speaker B: —everything. There's gradients, but you have to meet the community a little bit where it is and then push the community. And that's what these programs did. But they were largely national models that I was kind of incubating debating the Birmingham version of it. Continue to do that. Always interested in ways to do more of that. As I started to spend more time down here, I, and I was also doing start, uh, investing and there would be startup founders and there was some real estate projects where I was thinking, okay, this would be neat to have downtown be more dynamic in this way and this kind of thing also that I may see in other markets.

Oh gosh, like this thing exists in Brooklyn, it would be fun to have a Birmingham version of it and people would like that. And also like humans are humans, we kind of all like a similar, largely the same kind of thing. Right, right. As I was down here more, I think I said, okay, Jared, you could keep finding the strategies yourself and bringing them here, but maybe you want to approach it a little differently, which is instead of taking national strategies and bringing them to Birmingham, Why don't you take people in Birmingham who are exhibiting versions of what you see at a kind of founder mode orientation and unleash them?

And that's been kind of a new leg of the stool of my work, which is I don't care what you're working on here. I just care that you're like going for it. And there's great institutions here and there's companies that make sense for some people to work for. But I want to balance that with people who are saying, I want to go off and start this new tech company. I want to start this wind power company. I want to start a food pantry. I want to start a restaurant. I want to start a sports youth league.

I don't really care. It's kind of like a bottoms up, let me unlock your potential and support you. Give it some thrust maybe. Yeah, and kind of like a little bit like, I don't know, A Thousand Flowers Blooming or something of just like more create the conditions for people who show a risk mindset relevant relative to the community. Or, you know, we can say agency and unleash that agency and then support them on the journey as a venture investor would. It's kind of like we invest in a lot of sectors.

This is kind of, you know, I don't know, impact venture. Some of them are companies. I invest in a ton of companies down here in a tech sort of way. I've invested in restaurant groups, I've invested in real estate developments, and I've invested in, nonprofit initiatives. It's kind of— that's when I say tool agnostic. Yeah. Speaker A: What I mean when you say conditions, like, how important is money? And then like, what are other— what else matters for these types of like, if you, if you had $100 billion just to deploy, like what would be solved and what would not be solved?

Speaker B: Going to be my $100 billion investor. I think that— Speaker A: and for what it's worth, like, I don't know how much of— my sense is Dan Gilbert being worth almost $100 billion or whatever it is has been really helpful for Detroit. But that's clearly not the only thing. Speaker B: Well, I think it's helpful because the time horizon by which he can make his investments, he doesn't, you know, external capital may not work on that time horizon. Yeah. So I think that is important. I think you can think in, in more decades and you can take, you know, buying the buildings that he did that didn't have a market return at the time and then create the conditions where that real estate will be valuable.

I think that, um, resources, financial resources are helpful. They, they can align people and drive things forward. I, a lot of people, there's a debate in markets like Birmingham that like, oh, there's an access to capital problem and you don't have venture capital the way other markets. And I think that's directionally true. And yet I know from our time at Thrive, it's like I can wire money to a founder in any market in the world in 30 seconds. And, and we are incentivized as anyone to go find those opportunities. And why, while they may not bump into you on, you know, Lafayette Street the way things do in New York, like we, we do go and hunt those things and venture investors are out there looking for them.

So I, I sometimes push back in Birmingham on the, like, it's just an access to capital. And we do have founders here who have built billion-dollar businesses, and they've found capital outside of Birmingham. So I think it's ultimately like, we need to keep developing our founders to be not excellent just for Birmingham, but to be excellent in the global marketplace of whatever they're building. And that's where some of my more recent work is like, hey, Hey, don't just look around town at your competition, you know, like let's make, let's normalize what people are doing to, to kind of go for it.

And what is, what does it mean to really that growth mindset? Like what does it mean to compete on that global level with founders everywhere? And it's scary, but I like supporting people and I don't really care what they're working on. And, and hopefully to your earlier point, I do the like, I listen and then also give the, like, tough advice when they need to hear it. Speaker A: Right, right. Another component of this is a huge part of expanding beyond a local maximum is, like, being able to see the other peak.

And it, it does seem that maybe especially for young people, like, the most ambitious thing you can conceive of is the most ambitious thing you've seen. Absolutely. Speaker B: It starts with being comfortable taking risk. So I'm, I'm trying to lay the ground for people to feel more comfortable taking risk. I think that we have been in a time where the tech startup is the like sexy thing, right? And that is important, but I don't know that every market has to be Silicon Valley, can't be Silicon Valley. And company creation in general and entity creation, I think, makes for a more dynamic place.

And so, um, I'm glad we have a set of people who are trying tech companies, but I'm just as interested in people trying non-tech-specific companies or new restaurants. We have, you know, it's pretty good food scene, and we have people that are trying to be, you know, who are inspired not by just the people here, but the Keith McNally's and the others in the world. Like, think bigger. Speaker A: There's an element of this that is like culturally reflexive, meaning the— Yeah. The best thing you've seen is— And that can compound in both directions.

Right. Speaker A: There's an element of this that is like culturally reflexive, meaning the— Yeah. The best thing you've seen is— And that can compound in both directions. Right. Speaker B: Yeah. And I think that in many ways, kind of like the internet is making the world flatter and people see all these things. But I, I think it was like half the battle. It's like you still, that feels far away. You know, Brian Charski feels far away. Exactly right. Exactly right. And I think that's why examples here locally that work are so compounding.

And so I think I want to create as many great outcomes. And then I also want to highlight that work so that the— Make the proximity feel like— Make the proximity, make like, oh, I saw that guy at the coffee shop. Like I can do that. It's not just this fairytale thing far away. Speaker A: This is why representation is like not a woke thing. Like it's like, like being able to see a person who looks like you or is from the same place as you or whatever the thing might be, there's like a psychological element of it that it's like, oh wait, I could do that.

Absolutely. It's, it's really, really powerful. I think it'd be cool to hear you talk a little bit more about the other stuff you've been actively working on. It sounds like, and I know one of the main projects, maybe it goes all actually farther back to the Birmingham Talks days, but can you talk a little bit about Small Magic and why that is a version, at least as I understand around like the kids experiencing language part, like a version of this kind of reflexivity? Speaker B: Yeah, so we started working on Birmingham, or started working Birmingham 2013, and as I said, I was like begging these national organizations to think about Birmingham, and you know, it was, you know, tiring, but we would get 'em here.

And then one day in New York, I get a call or an email and it's like, hey, we're Bloomberg Philanthropies. "Are you like the Birmingham guy?" I was like, "What?" Like, I was like, "Have I made it finally?" And they said, "We found a program out of Providence, Rhode Island that focuses on early childhood kind of brain word development, and we're looking to take it to other cities. We've heard you've done a version of taking models to Birmingham." And it was neat 'cause it was like, wow, I've been begging people so long to think about Birmingham and maybe we're making progress, maybe there's something to this.

And so the general concept is, um, um, lower-income kids hear 30 million less words by the age of 5 as higher-income kids. And that is so important for— Speaker B: Yeah, so we started working on Birmingham, or started working Birmingham 2013, and as I said, I was like begging these national organizations to think about Birmingham, and you know, it was, you know, tiring, but we would get 'em here. And then one day in New York, I get a call or an email and it's like, hey, we're Bloomberg Philanthropies. "Are you like the Birmingham guy?"

I was like, "What?" Like, I was like, "Have I made it finally?" And they said, "We found a program out of Providence, Rhode Island that focuses on early childhood kind of brain word development, and we're looking to take it to other cities. We've heard you've done a version of taking models to Birmingham." And it was neat 'cause it was like, wow, I've been begging people so long to think about Birmingham and maybe we're making progress, maybe there's something to this. And so the general concept is, um, um, lower-income kids hear 30 million less words by the age of 5 as higher-income kids.

And that is so important for— Speaker A: we mean 30 million less words. Speaker B: Parents, caregivers talk to them less. They're just not— they've heard 30 million less words. Correct. And how much that specific interaction— and not just like TV words, but also like conversational turns and the engagement with an adult. Literal reps. You know, just reps. And so they, it had some early progress in Providence and Bloomberg had identified and wanted to bring it here. And so we partnered with them and partnered with the mayor's office here in Birmingham.

And it was kind of an incubation in the same way we would do at Thrive where conceptually is an interesting idea. We needed to find a way to make it work for Birmingham. Absolutely found the right founder in a woman here named Ruthann Moss. And I played kind of venture investor, board chairman, co-founder. We are now the largest implementer of this solution in the country. The mission is to make Birmingham the best place to raise a kid under 5, and it's a huge aspiration. And that certainly goes beyond just this talks program.

We've got to think about how are we providing are we talking, you know, childcare and how are we talking early childhood education tools broadly, you know, health-related things. And so it's big and it's bold, but I also think it's, I mean, we have a responsibility to put kids on the highest trajectory we can. And schools are hard to influence, the K-12 system. And so early childhood is maybe an interesting, you know, more— Almost like an arbitrage. Yeah. Box for to be entrepreneurial in versus trying to change the schools. Um, and so it's, it's one of the initiatives here that I spend the most time on and really proud of.

Speaker A: You said to me recently you're busier than you've ever been. Speaker B: How is that? It's— I, I've never had a problem with having a lot on my plate. I— well, sorry, I should clarify. Speaker A: I guess I mean twofold. I mean, how is it? And I also mean, like, how, how is that possible? Yeah, like, that's not intuitive for the So there is a person from the outside looking in who's like, oh yeah, Jared left Thrive and he like came back to Birmingham and he's kind of hanging out.

Speaker B: Well, I'm, for a while, for a year or so there, I was like, just slow down, see what that feels like. And then I had this incredibly high bar for if this interests me, it deserves to be on the calendar and it better interest me a lot. And I'm interested in a lot of things and that certainly goes beyond Birmingham. There's, you know, I, I, I remain super interested in investing in general. I think investment firms are fascinating. I love supporting Thrive however I can. And then there's new people and not even just in venture, like emerging people building funds and, and they're interested in me helping them.

And that's exciting. I guess I think the, maybe what I meant by that is I have, a lot of big things across the spectrum from Birmingham to, there's some other investments, there's investment firms, and I'm trying to stay at the most like strategic level of those things. I think sometimes in the other jobs there was a lot of like busy work and this feels like I'm, I'm really trying to stay at the like not busy work but very high ROI work. And I have as much as that on my plate as I've had.

Speaker A: You, maybe a little in the weeds, but you have both the maybe discretion and also like ability to not get into the quote unquote busy work. But also I think what people seem to say about you is that you're like very willing to roll up your sleeves. Like how, what is the threshold on that? Maybe it's just about the top level choices. Speaker B: Yeah, I mean, you had to do that. And I think when I took on the responsibility at the White House, certainly, and even even at Thrive, it was like, you know.

Speaker A: But I don't necessarily even mean like in those contexts. I mean. Speaker B: Yeah, well, I think I learned that it was important. And I think I learned, as I said, Andy Card was like, you know, yes, strategic and you have to do stuff. So that would prep me for, and it's like, you know, it's like who wants to be about a big shot that like won't roll up their sleeves? Like, it's just kind of like, it's like such a high status kind of move. And, you know, like, I don't know, that's just not my energy.

Yeah. Speaker A: How do you think about, presumably you are less, you are more distributed, like you have more seeds or things growing now. Like, what are the costs and what are the benefits of concentration? Speaker B: You know, two experiences in the White House and Thrive where I was deeply concentrated. Right. Like, I really love those. And yet, you know, it's funny, it's like you were at a thing at the White House, but you had 1,000 things going on. And Thrive, you have a portfolio of companies and projects. Speaker B: You know, two experiences in the White House and Thrive where I was deeply concentrated.

Right. Like, I really love those. And yet, you know, it's funny, it's like you were at a thing at the White House, but you had 1,000 things going on. And Thrive, you have a portfolio of companies and projects. Speaker A: So concentrated frames, but within those. Yeah. Speaker B: And I think now, you know, I feel, yes, there are a number of projects, initiatives, investments, you know, people that I'm trying to help, but I'm also like deeply concentrated and disciplined on like, almost being selfish in a way of like, what am I most interested in?

And if I'm interested in it, like, I'm going to be unapologetic and go explore it. And it, however long it serves me and I remain excited and think I can help, great. I get that from perhaps an external view that can look like, I don't know, spread thin. And I don't, I don't, I frankly get de-energized by being spread too thin. And that's why I've started to build a, you know, a team that can lever me up more and help me be sufficiently effective at this broad range of, of things I've got going on.

I do imagine that I will continue to concentrate and narrow, um, whether that ends up being, you know, a firm one day or a role leading something. I'm not totally sure. I'm really— I'm more okay with that. I think earlier in my career I would have been very nervous about like, what, you know, what am I— what's the right thing to do? What's the the, you know, the world or I've been out of the game, quote unquote, for a long time. Yeah. I don't feel, yeah. Speaker A: There's an element too of like one good way to find a really concentrated thing is to plant a lot of seeds.

Speaker B: Absolutely. And I think reap, I got some advice from an amazing mentor named Tom Tierney who was an early leader of Bain Capital and Bain Consulting. And I had actually brought him down to sit with the president about, about, you know, what a post-presidency life could look like. He had helped leaders think about that. And I remember him saying like, Jared, I've always found like repotting myself has been an incredibly valuable way to live my life. And, you know, potted myself in DC and then potted myself and, you know, we're potting some things going on now and that'll change too.

Speaker A: Did you, we didn't talk about it when we were speaking about it earlier. When did you first come across the, How did, when do you use your best stuff idea? Speaker B: I was fortunate to be introduced to like a coach, you know, which I'd never known much about the like executive coaching world. And someone said, you know, you know, Tiger Woods still has a coach and he's at the top of his game. And so like leaders should try coaches. And so I met someone and she gave me the exercise and I've since sent it around a lot.

It's probably helpful in the— Speaker A: in approaching the, like, combo of self-knowledge and happiness quotient. Yeah, absolutely. Do you think about your life in, like, acts or in, like— like, at the very least, you could retroactively look back and you have— there's some, like, pretty clear chunks. And I'm curious if that's still resonant. Do you feel like you're in a third one of those? Is it a pause? Is that not the right way to think about it? Speaker A: in approaching the, like, combo of self-knowledge and happiness quotient. Yeah, absolutely.

Do you think about your life in, like, acts or in, like— like, at the very least, you could retroactively look back and you have— there's some, like, pretty clear chunks. And I'm curious if that's still resonant. Do you feel like you're in a third one of those? Is it a pause? Is that not the right way to think about it? Speaker B: I mean, I think it set my set of experiences being quite different from each other. I think that sets up that way. And I think about it because they were very different for me too.

I mean, DC and Thrive and now has this more kind of focused on, you know, things outside of work a little more. So I think so, but I don't know that I think that like this act will look book, you know, oh, it'll be 10 years just like the previous 2 were kind of 10 years, or that'll have, you know, a story that the outside world finds as interesting. I mean, like, and I'm sure someone's like, oh, he's, you know, Thrive and the White House, like, what's the next thing? And that's like a lot of external pressure to put on, you know, like my story.

And I don't, you know, it's like, I think it may have it because I think if I explore and go after things that are interesting to me, Doesn't seem like you guys said the two other things via super— Speaker A: I don't want to say not deliberate, but it wasn't like very— Speaker B: Wasn't for the purpose of the story. Yeah. Yeah. That feels like, you know, there's a lot of pressure that people have to do that. And yet, gosh, that's like someone else's, you know, that's kind of doing it for someone else.

Speaker A: I don't want to say not deliberate, but it wasn't like very— Speaker B: Wasn't for the purpose of the story. Yeah. Yeah. That feels like, you know, there's a lot of pressure that people have to do that. And yet, gosh, that's like someone else's, you know, that's kind of doing it for someone else. Speaker A: Yes. A few other things. We talked about a handful of kind of people who have been influential on you and mentors. Um, two we didn't speak about explicitly in the context of Thrive, um, John Winkelried and Nitin Nohria.

I'm curious to the extent those guys were influential on you personally or on Thrive, what, what you learned from them. Speaker B: I want to give them both like appropriate time. I mean, John Winkelried is such a special person, and he was special for Thrive in our early days where we you know, as I said, we tried to learn from others who had done things, but John was like there in the weeds with us. And he's a, he now leads TPG. He is such a motivating individual to be around. He absolutely, you know, was in the trenches of Goldman Sachs for his career, helped scale that organization, And the fact that he was willing to sit with us when we were not a big firm that was well known, and he's a great listener.

He, I think, helped both the firm and also Josh and me individually think about our own leadership style. You know, he could pick up the phone and call me and ask, you know, like, I'm thinking about, I don't know, going to buy some, from dollar stores, and I'll be like, I'm in, you know, like, I'm thinking about doing this. Like, I, you know, John is, is really special, and I know everyone, whether at Goldman or Thrive or TPG, has kind of loved working with him. And, and I think for me also, at that time in Thrive, I had always— I had lived in a very strong mentor environment in the White House, and so many different individuals, the ones we've talked about who are a few years the president, and then we get to Thrive and it's like, just gotta figure this out.

And so having John as kind of this guide in all of that and, you know, never put his finger too strong on what we were doing, was more, you know, someone to talk to and listen and work through things with was really special. And Nitin came into Thrive, you know, Josh and Nabil had known him when they were at Harvard Business School. And stayed in touch with him. And Nithin is like a Yoda kind of figure. Like, there's just so much wisdom in Nithin, and he sees things very clearly. He is a straight talker.

I mean, he's very strategic and he sees all the dimensions of organizations. And, you know, a person not only was dean of Harvard Business School, but he's been on boards of massive companies and leaders go to him. And the fact that, you know, I had a few years with Nithin and he's still around the organization today and he, and fortunately he's stayed in my life and he's spent time with Birmingham entrepreneurs, which I'm so grateful for. Because it's like every, you know, his kind of wisdom to words ratio is so high.

And he's also a great, great human being. Speaker A: It's telling that you guys found a way to have people like that around over the course of building the firm. Do you, this might be too personal, in which case it's fine, but do you, if, what, causes you, if you do, to reach out to the president for advice or otherwise? Speaker B: Well, I'll start. I remember when we were working, when I was working for him and people would call him, his friends or people that had left, and he'd make time for them.

But then they'd maybe like call a few weeks later and be like, I just talked to that person. So I kind of try to like use my time with him. I know, you know, that he cares about me and he has my best interest at heart. And there's been some times with big decisions I've had in life and some work stuff, and he was willing to listen, speak, you know, he's an instinctual person. And he said, "This is what I think." And it was so perfect advice. He called me earlier this year about my mom And I didn't make it very long without getting a little sniffly, but he wants the best for me and that means a ton.

And I feel like the relationship has evolved from me working for him to being someone he cares about, friendly with, I would do anything for him. As I said, other than my parents and grandparents, like, no person has had more of a positive impact on me. Speaker A: Not obviously to be compared, and not someone you, to my knowledge, you know at least well, but what do you admire about Nick Saban? Speaker B: Well, I'm really grateful that he brought us as many national championships as he did, and I think his commitment to excellence, to competing not with others but with his self, like, he's motivated to just be better.

And even when he was on the top of his game. He wanted to be better. A number of years ago, actually, I was sitting with, with Nithin at Thrive, and I said like, we should get a Saban case study. And so I called some people down in Birmingham and he called the sports HBS, you know, case study person. And we ended up putting this case study together that I went and saw delivered. And, you know, I think he's, The process orientation there is incredibly successful. It's worked, it's worked for him.

He like refined it. I think also, think, look at all the coaches that have gone on to do great things. I mean, he set an example. I'm sure it wasn't an easy environment always to work in, but I also imagine those coaches are incredibly grateful that they got to see what excellence looks like and now, you know, are clearly benefiting from that. Yeah, the tree is bananas. Speaker A: What are you drawn to in sports broadly? Sports on one hand are totally trivial. Right. And on the other hand are like one of the more human things we have, but I'm curious.

Speaker A: What are you drawn to in sports broadly? Sports on one hand are totally trivial. Right. And on the other hand are like one of the more human things we have, but I'm curious. Speaker B: Yeah, I think I've thought about that, 'cause right, it's like, it's, I actually, I think I wrote my college essay on like the Alabama-Auburn game as a kid, and it was both like, —like, it's amazing that it takes up so much attention in the state, and yet, like, it sure does take up a lot of attention in the state.

And, you know, I do think it is, it's an interesting, like, community bring-together thing. I think you can have, I mean, one, I enjoy it, and that's, like, maybe enough. And also, historically, I think sports organizations haven't always been the some of the best-run organizations relative to other industries in the economy. And now you're seeing with so many dollars in there, a lot more investment. And so I'm kind of curious, like, in what ways can excellent leadership and organizational stuff impact sports organizations? Speaker A: What do you hope to be known for, or most hope to be known for?

Maybe it comes back. Speaker B: I mean, I hope that I'm known as like a great friend. Um, someone who brought out the best in other people, someone who— I don't want to say pushed in a hard way, but, you know, encouraged people to bring out their best self. Um, someone who was, was good energy to be around. And any of the other, like, accolades separate from that just feel like kind of details. Yeah. Hm. Speaker B: I mean, I hope that I'm known as like a great friend. Um, someone who brought out the best in other people, someone who— I don't want to say pushed in a hard way, but, you know, encouraged people to bring out their best self.

Um, someone who was, was good energy to be around. And any of the other, like, accolades separate from that just feel like kind of details. Yeah. Hm. Speaker A: My last question: what have you learned from and what do you most admire in your mom? Speaker B: I've learned what unconditional love is. Um, I've learned what it means to like fully champion a person, and the way she championed me I've learned to like dream big. And I admire how much she loved me and my sister and, you know, how she showed up to like just want the best for us.

Speaker A: Those last two, I think, go together. Speaker B: Thank you, Jerry. This was great. Thanks, Jackson. Speaker A: Appreciate it. Of course. Thanks again to Notion for presenting Dialectic. And thank you for listening. Notion is a tool that you can use with your collaborators and with the incredible power of AIs to work deeper, to think together, and to produce more. I think the best tools amplify us, and Notion is a tool that is focused on doing that, specifically on enabling you to more deeply immerse yourself in the work that matters, to do it with the people who inspire, who improve, and who expand you, and get help from AI along the way so that you can do even more.

Once again, you can find more at com/dialectic, and they are shipping new updates. Seems like every week at this point, pushing the bar for all of the ways you can use different AIs. One of the things that's great about Notion is that it's a bit of a Switzerland, so you can cycle between all of the models that you might use, whether it's Anthropic's models or OpenAI's or otherwise. Thank you again for listening. And if you enjoyed this episode, please share it with a friend. And thanks again to Notion. I will see you next time.

Speaker B: Thank you, Jerry. This was great. Thanks, Jackson. Speaker A: Appreciate it. Of course. Thanks again to Notion for presenting Dialectic. And thank you for listening. Notion is a tool that you can use with your collaborators and with the incredible power of AIs to work deeper, to think together, and to produce more. I think the best tools amplify us, and Notion is a tool that is focused on doing that, specifically on enabling you to more deeply immerse yourself in the work that matters, to do it with the people who inspire, who improve, and who expand you, and get help from AI along the way so that you can do even more.

Once again, you can find more at com/dialectic, and they are shipping new updates. Seems like every week at this point, pushing the bar for all of the ways you can use different AIs. One of the things that's great about Notion is that it's a bit of a Switzerland, so you can cycle between all of the models that you might use, whether it's Anthropic's models or OpenAI's or otherwise. Thank you again for listening. And if you enjoyed this episode, please share it with a friend. And thanks again to Notion. I will see you next time.