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

[00:00] If people were to look at your resume, they would infer that you are like a cold-blooded killer, basically. I got to the White House in July of 2002. 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, I remember my phone.

[00:30] 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 four or five [01:00] to a section 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. He's had a year of investment banking experience. I've had seven 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 [01:30] to 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. [01:40] 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,, 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, [02:10] 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 of humanity. He is an amplifier of people, whether it be the leader of the free world, [02:40] 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, 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 an honor and privilege to go down to Birmingham and hear him tell his story. [03:10] and to think about the ways that you can contribute to [03:13] the people you want to amplify, the institutions and communities you are a part of, and the way you can bring humanity together.

[03:19] into the work. You can find more at fm slash Jared Dush Weinstein, the transcript, all the links. And if you like the episode, please give it a thumbs up, five stars, or subscribe wherever you're watching or listening. [03:31] 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.

[04:01] 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 slash dialectic. And if you are using it for all kinds [04:31] things I would love for you to share with me. With that said, here is my conversation with Jared Weinstein. [04:37] Mr. Weinstein, we're here. Mr. Dahl, thanks for coming. I'm so glad to be here. Down in the deep south, as you said. [04:46] Not my first time in Alabama, but first time in Birmingham. It's good to be here. We're excited you're here. We need more Jackson Dahl energy down here. It's an honor. We are going to go a bunch of places today.

I'm going to start with... [04:59] I think... [05:01] actually it's worth setting the context, you have spent your life across a bunch of different worlds. [05:07] 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 lie pretty low. 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...

[05:29] 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. [05:40] And I think that's something that is kind of a funny thing to look at. I also noticed your logline on LinkedIn is... [05:50] founder, advisor, friend. Uh, one of your former colleagues at thrive said, Jared is a friend in the truest sense. Well, [05:59] And so my first question is, what does it mean to be a friend?

[06:01] Thank you. [06:03] Wow, that's really kind. What does it mean to be a friend? I think it means... [06:09] Showing up. [06:10] I think it means... [06:12] Um, [06:14] assuming the best of... [06:16] 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. [06:24] I like championing other people. [06:27] I like seeing other people... [06:30] um, 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.

Um, [06:41] I get tons of energy from being around other people. And I also know... [06:46] And [06:47] for as long as I can remember, think about how much other people have played a role in supporting me. And, uh, [06:54] And how good of friends they were to me along the way. And whether they were peers or managers or whomever. [07:03] There's an obviously related component there. [07:06] Thank you. [07:07] 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.

And I don't mean to say like, I think, again, as we'll talk about, you certainly know how to get serious when things need to be serious. [07:24] 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 Birmingham. And certainly, [07:37] 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, [07:45] There are people who kind of cleanly separate these things.

Yeah. [07:49] And for you, it seems to be a little bit more... [07:52] Overlapped yeah, 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 is [08:03] led by President Bush, but also led by Chief of Staff Andy Card. [08:09] It was incredibly, of course, serious place. [08:13] and also a joyous place, even in the most challenging of times. And I think President Bush recognized that you can, you know, [08:22] have to take that job incredibly seriously.

But you can do that with joy and you can do that with warmth. And frankly, you can get... [08:32] Mm-hmm. [08:32] the best out of people if you have that kind of environment, a supportive environment, a challenging environment. [08:41] And. [08:42] 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. Yeah. [09:12] all these different people, but also, you know, [09:14] 22-year-old Jared Weinstein and whatever you're supposed to do, like bring your A-game. And you can do that with... [09:22] I mean, he has a... [09:24] President Bush had a great sense of humor, but he was in there at 6.30, 6.45 m. and being like, man, we only have maybe four years, eight 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. [09:54] colleagues got to experience and felt that. Yeah, it's interesting. I think there's a [09:59] Default. [10:01] It's like the X, Y axis of seriousness and... [10:05] camaraderie or whatever, family vibe or any of those types of things, even joy, to use your word. [10:12] those two things don't tend to be correlated. There's a certain kind of feeling that as the stakes rise, we all have to become more robotic.

Yeah. Shift it the other way. I... [10:24] 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 top behavior. And yeah. [10:37] 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, in kind of multi-decade organizational and culture building, it doesn't feel like something that's going to be long-term sustainable or long-term excellence.

Let's start with... [10:57] The beginning, though. I'm curious, like, you're in college at Duke, and you decide to work on... [11:02] a political campaign, um, [11:05] Thanks. [11:06] 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. [11:17] 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. Sure. Sure.

[11:26] So I got to Duke in 1998, and I learned two things right away. One is there's a... [11:33] 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 and 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 [12:03] And so I needed to get that done after my sophomore year.

[12:06] And I went to the intern coordinator and said, um, [12:10] 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 and said, but yeah, if you get there, we'll give you credit for your internship. And so I, I, [12:26] Started, I think, in October of my sophomore year, cold calling down to Austin, Texas. I didn't know people. [12:32] Um, but something about him and I can, and, and what he was standing for just kind of spoke to me.

I wasn't deeply involved in politics. Um, [12:41] 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 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 eight 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.

[13:11] for something to do this summer. And I was very prepared for an interview. It was 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. You need 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. [13:41] And by the end of the summer, I was supposed to go abroad for my junior fall. And they said... [13:48] 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. And they kind of look at me like, [13:55] You're an idiot. You're working for the next president. Why don't you stick around? And so that led to the campaign and then – [14:03] continued on from there.

Did it feel... [14:07] In any way, did it feel risky? Either on the dimension of just, I don't know, doing something that's slightly divergent and or related to the fact that it wasn't a sure thing. Like... [14:18] And obviously very much came down to the wire in the end. [14:22] It definitely came down to the wire. It did not feel risky. It became a little riskier after we won because – [14:30] I was going to go back to Duke for my junior spring, and some buddies on the campaign started to say, why don't you come to

C. with us? [14:39] And I was kind of like, what? Drop out of school? Like, that feels a little riskier, at least at a time. And fortunately... [14:47] my parents who played such a role in my life, [14:51] said, if this is what you want to do, we support you. And the fact that 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 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 – [15:16] uh, to DC with us.

And I said, yes, sir. And he said, Jared, I'm going to [15:20] 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. [15:34] And I think if I had gone up there, they would have 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.

Yeah. [15:46] 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, and [15:56] I worked for Carl. I was the only intern in the West Wing, which was pretty exciting and special. [16:02] And then when I graduated in 02, [16:04] he helped and they created an entry-level job for me. What did your friends think, particularly when you were in school? I don't think... [16:13] The... [16:14] George W. Bush fan club at Duke was, was that big, uh, certainly during the campaign.

Um, um, [16:21] 9-11 happened my senior year. [16:25] So... [16:25] 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. [16:35] 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.

Yeah, yeah, yeah. They didn't know what it would look like. And I didn't even know what – [16:52] whether a job would come until almost the last week of college. Right. 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, like, how did I get here? 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.

You think more people should work in government? [17:21] aspire to [17:22] Absolutely. [17:25] I think that... [17:28] we have a really special thing here in our country and it's not perfect. Um, it hasn't been perfect ever, but we, um, [17:36] aspire for it to be great and it has done a lot of amazing things and i don't think that's um [17:45] 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. [18:02] And, [18:03] Yeah. [18:04] What game have you played? What organization have you been a part of where if... [18:09] you know, if you don't have the best people, a part of it, um, you have a good chance of winning. And so, um, [18:16] 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 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 President Bush not only looked to people he knew from Texas, but people across the private sector. Yeah. [18:41] Um, [18:43] 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 till you've worked in something like government, maybe a nonprofit sector. [18:59] And that's really special. And I think even if you do it for two, four, six years in the arc of a long career, I think you'll grow from the experience and I think the country benefits from it.

[19:11] You started to talk about it. Your first job, I think, was working on... [19:16] Effectively in like scheduling? Scheduling. [19:20] When you found that out, how did you feel? Yeah, well, you know, it's not the thing that draws most people to government. And I got a call of kind of a few weeks or so before graduation, and they said... [19:33] Jared, we have an opportunity we want to talk to you about. Oh, it's national security or economic policy or what's it going to be? And they said a scheduling office and like – [19:43] 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 [19:54] kind of precious resource at the White House than the president's time. I mean, there are so many issues that the president... [20:01] 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 [20:09] 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. [20:23] 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.

[20:53] operational execution thing that you cited. I think that was very much the early days of it. Yeah, it's kind of an amazing way to get a bird's eye view from like the bottom. Totally. Kind of in a way that might be unexpected. What do you think... [21:11] Have you spent much time thinking about what you did... [21:15] or what you showed when you were working on the campaign that not only – [21:22] had them excited to bring you back, but [21:25] led to that seat to the extent they were thinking about what that seat meant?

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. [21:46] Um, [21:47] 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 I knew I could work really hard. I... [22:05] 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. [22:15] 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 is, [22:23] You know, certainly in a White House is pretty important. [22:26] Um, [22:28] I think whatever judgment a young 22 year old can show around the job that they're tasked to do.

I, I think I had pretty good judgment. I could, there was, um, [22:38] a lot of balls to juggle, to say the least. And I think they felt I probably did that with... [22:45] a kindness, a compassion, but also a, you know, near zero failure rate, I think. Um, [22:53] And that led after a year and a half or so in the scheduling office to 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.

[23:06] almost the CEO of the White House in a way. [23:11] And his job isn't 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, you know, the food staff, the floral shop, like the White House grounds, the Secret Service, the advance team. I think I was had very much like a service orientation of no job too big, no job too small. Do it with discretion. [23:41] was this nice guy, Andy Card, who...

[23:46] enough good things can't be said about Andy and also our second chief of staff, Josh Bolton. Andy was – [23:53] 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.

Yeah. [24:20] And, uh, [24:22] He was first to the White House in the morning, so I had to beat him into the White House to be ready. What time did you shot? I targeted 5, which was the alarm went off at 4.12 m. Someone asked me one time, like, why 4.12? It's such a particular time. I said, well… [24:41] 4.10 was too early. I got two more minutes of sleep, and if I waited until 4.15, I wouldn't be there at 5. Starbucks wasn't open. I had to stop at the 7.11 for a good 7.11 coffee.

How much were you sleep? [24:55] My guess is I kind of like... [24:58] Got in bed around [25:00] 11:30 or so, 11, 11:30 and kind of popped up and- - Matthew Walker wasn't pleased with this strategy. - Right, right, no, no. [25:12] Sleep was not up. That's what being 22 is for. Totally do it. When, at what point did, because presumably you're working on a campaign, that's one thing, you're an intern, whatever. When did the radical stakes and radical pressure happen? [25:27] 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. [25:50] Right. [25:52] Right, there's other environments. Silicon Valley failure is the thing. DC, you know, failure is not the thing. I think that...

[25:59] I was so fortunate to just see [26:02] a campaign especially that was [26:06] 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 going to deal with it. You know, and so I think I just saw these, I don't know, adults in the room. I realized those adults made decisions. [26:28] have been younger than I am now, but like they felt like the leaders of the campaign and they were, uh, [26:34] 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 – [26:45] We've kind of been there before. Act like you've been there before a little bit. [26:51] The night of the election in 2000, when Vice President Gore, he thought Florida had gone for him, you know, [26:58] There were election parties happening. Hey, guys, we've got to stop this party. We've 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 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 2002. So 9-11 had already happened, and there were early – [27:27] I guess, signals that, you know, the Afghanistan war was already in place. [27:33] And then Iraq was kind of on the horizon. Iraq, I think, started in March of 2003.

[27:42] 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 – [27:52] hey, we trust you to do the job we've hired you to do. They're kind. It's kind of – [27:58] 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. Hmm. [28:09] You mentioned the White House chief of staff being the CEO. I guess the assumption there is that the president is the CEO of the government?

CEO of the government, chairman of the White House. I mean, the president... [28:21] Can't... [28:23] 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. [28:38] the whole White House and the president is kind of like teed up to make decisions at the right time. And so [28:44] 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?

[28:57] not too early to where it becomes stale and not too late that a book is kind of irrelevant. And so how do you ensure that whole thing works? [29:07] 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 and I think with the chief of staff, he he's really looking for someone that makes the system work. [29:21] is the... [29:23] To what extent is the White House as an organization like this? [29:26] other companies or startups?

Is it part, part of what you maybe you were alluding to too is like, [29:33] and maybe we'll get to this, is like the president... [29:36] maybe in some sense, like doesn't do that much. [29:40] And what I mean by that is the president's job is almost explicitly, I would assume, like judgment and people. [29:47] And like... [29:49] If they're too in the weeds on anything. You will never hear me say that the president doesn't do that. Yeah, it's a ridiculous statement in some sense. I guess what I mean is like, [29:58] I would imagine...

[30:00] It's very, very costly. Anytime the president has to go into the weeds. [30:05] I think it's very costly for the present 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 – [30:16] 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 is view or support or. [30:39] 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 giving him leverage. [30:51] giving him leverage, 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 the president. And so – [31:01] 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 newspaper that is critiquing me written by a 26 year old op ed person. [31:31] the most important thing. It's, are we operating from principles? Are we operating and making the best decision possible with...

[31:40] imperfect information and, um, [31:44] And then executing on it. Yeah. You... [31:47] We're working for the chief of staff, I think the second chief of staff. [31:51] And then you got a call. [31:52] down to the White House, excuse me, down to the Oval Office. Can you tell me that story? [31:57] Sure. So I was the chief of staff's aide and I was kind of the backup of [32:02] to the president's aide, um, who's, uh, was, and is, and remains a great friend of mine. Um, so if he was ever sick, I would fill in.

So the, the president kind of knew me and this is what, like two, three years in, [32:15] This is... [32:16] Three years into being the chief of staff state and, um, [32:20] And you needed a backup. I mean, the president had to keep going. If Blake, who was the president's aide at the time, got sick or needed help, [32:27] help, you needed someone that could [32:29] seamlessly drop in. [32:31] And Blake was going off to business school. And so you knew that there was a new personal aid that was likely to.

[32:39] And I think it was... [32:42] Um, [32:43] likely that I was... [32:45] 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, um, [32:53] So on May 1, 2006, at like 7.04, I remember my phone. It rings and it says... [33:01] kind of 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, you know, 30 feet down to the Oval Office, and I popped in and say, Hey, Karen, what do you need? [33:18] She said, I don't need you. He does. And the next thing I hear is, Jared, get in here. And he's in there with chief of staff. It 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. How was that walk back to wherever you were going? [33:48] uh [33:50] I think as early back to the campaign of which at the time would have been six years prior, [33:56] 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 that 20 something could have.

And I didn't call my parents a lot during the White House experience. I didn't want to. [34:16] be bragging and I think I was worried that if I shared too much with them, they would brag to people. Um, [34:24] But I think I sat with it for a little bit and then called him and told him. [34:29] in that job [34:31] White House or excuse me, the president's aide, sometimes called the body man, like what actually is the job? [34:36] It's not really a JD. It's kind of whatever... [34:41] makes sense for the president.

For our president, for President Bush, [34:46] It was... [34:50] deeply understand his day, deeply understand the kind of, [34:55] Um, [34:57] details of the day, the movement of the president. And I can walk through what a day look like and also understand his preferences. I mean, you wanted him always operating at his best. And that didn't just mean, you know, uh, 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 them?

Um, um, [35:24] 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 – [35:36] too much information. I'm 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. Yes. Yeah. 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. And as the personal aid, you're trying to do this, you know, being that he, he would always remind you, you know, Jared, you're not [36:06] here to help all of us be successful and really like within earshot out of camera shot was a bit of our, uh, personal aid motto, um, you know, stay behind the scenes and make it work. [36:17] How much did you sleep when you had that job? About the same. About the same. I mean, I tried to get in by five, and what that looked like was I would get a duplicate copy of his nightly briefing binder, 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, etc.

[36:41] 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 [36:53] Is this going to 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 the Super Bowl champions are coming in?

Why did we do this this way? Just very – Keep the flow, basically. Keep the flow. Keep the flow. [37:11] And, you know, [37:12] If I was in sync with him, I would have fired off a bunch of emails in the morning asking people for clarification, maybe suggesting changes. [37:21] And then he would come in at 630 or so and start going through things. And he'd say, you know, Jared, why are we doing this event this way? And, you know, if I had nailed it, I would have been like, sir, actually, I saw that as well.

[37:31] you know, I'm going to work on a change, make sure it's, you know, and, and part of it was that, you know, so much of it was like, he wanted to be considerate of others. I think everyone kind of, um, 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, you know, wait, you know, so how do you make it such that their experience at the white house is not, Oh my gosh, we're here to kind of, [37:53] make the president happy.

The president was welcoming people to the white house, but, um, I, [37:58] That was what a morning looked like at 8 m. 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, 930. It's OK. 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 brief for five 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 five minutes and take a photo. Then we're going to go down and have lunch, you know, with. [38:28] economic policy leaders and then we're going to 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. And you're like the primary interface for all of the things happening basically at a very operational level, right? You know, like just, and you'd say to, you know, um, 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 a, and it was the, the other staff in the [38:58] just making the [39:00] minute by minute operations and logistics happen. How much time do you spend together? I mean, I guess it's in these 10-second... [39:09] You're spurs sometimes, but you're basically just with him the entire day. Unfortunately for him, he had to spend a lot of time with me. 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. [39:32] Um, [39:34] So, [39:35] Most of the waking hours, you know, but then he would leave. [39:39] usually to go back to the residence by – [39:42] Late afternoon, he'd maybe get a workout in, start working again on the next day's materials. He'd call over for stuff. 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. How much consistency – [40:02] I guess I'm curious how much consistency and structure there is to the president's time versus just reacting to... [40:09] Obviously, crazy things happen and then you're just reacting. But are most days relatively similar to... [40:15] In terms of you're being the CIA guy and then it breaks if there's chaos or like. Yeah, he's I don't know what other White Houses operate. He was a very disciplined, you know, basically everything in five minute chunks was planned out throughout the day.

And he ate at the same time. And 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. [40:43] two to three months out or so. [40:46] 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 themes, but... [40:58] I mean, so many things show up in the world that you have to be prepared for.

[41:06] 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 – [41:15] A Supreme Court justice passes away, so you've got to be ready to nominate a new Supreme Court justice. [41:23] you know, various, uh, [41:24] I don't want to call them crises because they don't feel like crises, but they're things that throw off your planned schedule. You're very used to divert. Yeah, totally. [41:36] How many... [41:38] Um... [41:39] How much of his, like, maybe this is a dumb question, but like, how many decisions is he making in a day?

[41:47] presumably all anybody ever wants is just like, what should we do? What should we do? What should we do? What should we do? [41:53] Hopefully some of that's getting abstracted away. I think he's making the big decisions. He's certainly making decisions on who's in his cabinet, who are not other kind of leadership roles across those agencies. They're recommending we want to put in this person as the undersecretary for this issue. [42:13] 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 make.

[42:23] 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 [42:34] He wasn't going to be secretary of state. Like that was her skill set. And Hank Paulson is, 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 he wanted to create the environment that he got the best ideas and then made the decision.

In what ways? [42:59] did he model excellence and in what ways do you think he was a particularly good leader? I readily admit that... [43:05] probably [43:07] No other person other than my parents and grandparents have affected me more positively than George W. Bush. [43:16] I'll come back to as a leader, but... [43:20] Hiesam. [43:22] He's a great father to his daughters. It was really fun, frankly, watching him as a husband to Mrs. Bush, their friendship and partnership and... [43:35] sense of humor between each other was, was, um, [43:39] Maybe I'll call it beautiful.

He was a great friend. I thought it was really neat. I'm pretty sure like, [43:46] He had dinner before he became president with the same friends that he had dinner with the day after he left the presidency. [43:55] He wasn't someone that needed to come to C. and, you know, care about, you know, being out of the restaurants on that. 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 – [44:14] He was [44:16] I think, incredibly consistent.

I knew what mattered to him. I knew what he was looking for. I knew what he wanted. [44:27] Wanted out of me and his and others and so you kind of knew what the bar was there was no Guessing no ambiguity no ambiguity he was [44:39] 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 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, behind a podium, saying words, giving a long speech. [45:09] him in like an environment where he's kind of a 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, [45:26] 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 like, that's exactly the right question he should be asking at the right level. And so he's an incredibly acute question asker. In a way that's intuitive? 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. [45:56] And I think that was a – [45:58] a skill that I saw and I really admired and it kind of, um, [46:03] 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. Right, right, right. 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 we, I think, [46:21] 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. Based on your experience with him. [46:41] Do you have a particularly and maybe just an experience inside? Do you have an [46:47] model of what you think is important in a president that might be... [46:53] different from everyone kind of looking at it from the outside or even just like what leads to success and actually doing the job? I think that I think the culture of the White House really matters. Um, I [47:05] I think that ensuring you have...

[47:08] great people who can bring you, [47:11] 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... Not getting, like, filtered. Not getting filtered, not having people come in, Mr. 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 [47:41] the best people willing to serve, if only for a short time, really matters.

It needs to be a well-oiled machine. [47:50] Because the president... [47:53] 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. Like cabinet secretaries or 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. What do you – [48:17] think people get wrong about him? I mean, one, he's a...

[48:22] he's really like a heart led person. [48:24] person. Um, he is really compassionate. Um, [48:29] He's a bit of a softy. I'm a softy sometimes. He's a softy too. I think people created this frat guy image of him. I think he was a guy that was really well-liked by both the frat crowd and the more academic, nerdy crowd. He loves people and he loves seeing the best in people. I think they think that, again, as I said earlier, people are like, what a nice guy. I really want to have a beer with him.

The have a beer with him comment, [48:59] to me always, um, [49:01] It felt like it was signaling for like he's just like a funny guy to be around and I think it misses – [49:08] Again, how... [49:10] acute of a question asker when it's business time you snapped into business time and It's not because it's in his best interest. It's like [49:19] 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 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 – [49:39] But, you know, you have to make really good decisions. And he's responsible and put in place the apparatus to have the information to make decisions. [49:47] you know, all those decisions. And I think history will look [49:52] Fonder and fonder on him. Obviously related, maybe a similar answer, but I'm curious what you... [49:57] hope he is remembered for. I... [50:01] Think...

[50:02] I hope he is remembered for... [50:06] you know, kind of who he truly is. I think he's a deeply, he loves our country. He happened to be president at Washington, [50:16] one of the [50:17] kind of most unimaginable attacks in our home line that really changed how we think about security and things coming to our shores. [50:27] And it wasn't obvious on September 12th that another one wouldn't happen once. [50:33] days later, months later, years later, and he protected us for a long time. Um, and, [50:39] 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. [50:51] 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, if you're chasing popularity, like it's, 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. There were a couple other people you had mentioned, uh,