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

·Investor, Operator
Jared Weinstein - Within Earshot, Out of Camera Shot

44-Jared_Weinstein.png

Description

Jared Weinstein (LinkedIn, X) is an investor, advisor, civic leader, and founder of Overton. This is his first interview.

Jared spent his twenties in the George W. Bush White House, starting as a scheduling intern and rising to become the President's personal aide. He went on to Stanford GSB, consulted for Palantir in its early days, and was a founding partner of Thrive Capital in NYC, helping build it into one of the most respected venture firms in the world over eleven years. After leaving Thrive in 2022, Jared returned to Birmingham to focus on Overton, where he invests in local founders, leads civic initiatives including Small Magic — an early childhood language development program — and works to make his hometown the best version of itself. He also continues to invest in startups, serve on boards, and seed and advise new investors. By his own words, he is busier than ever.

Despite his very serious resume, anyone who knows Jared will tell you that he radiates humanity. He has spent his career amplifying people and helping them become the best version of themselves.

We trace the arc of his career, talk about what it's really like inside the Oval Office, what he admires about the President, and the unlikely pivots that led him beyond a prodigious start. We also discuss what he and Josh got right at Thrive in the early days, how high stakes environments can be psychologically safe, and how to support incredibly ambitious people. Then we talk about his theory of change for Birmingham, the work he is doing now, and his reflections on where he's been and what he'd like to be known for.

I hope this conversation gives you a model for what it looks like to bring your full humanity into high-stakes work and inspires you to commit yourself to the people, institutions, and communities you believe in.

**Dialectic is presented by **Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic.

Timestamps

  • 00:00 - Opening Highlights
  • 01:40 - Intro to Jared
  • 03:32 - Thanks to Notion
  • 04:38 - Start: Being a "Friend" and Bringing Humanity to Serious Work
  • 10:55 - From Duke to the West Wing
  • 31:45 - Riding Shotgun with President Bush
  • 59:27 - Starting Over Out West: Post-WH, Stanford, and Palantir
  • 1:16:05 - Meeting Josh Kushner and Building Thrive Capital
  • 1:44:37 - Founders, Humility, and the Three-Body Problem of Ego, Ambition, and Impact
  • 2:06:41 - Leaving Thrive, Coming Home to Birmingham, and Overton
  • 2:32:40 - Busier Than Ever: Mentors, Life in Acts, and What You Hope to Be Known For
  • 2:49:11 - Thanks Again to Notion

Links and References:

Transcript

(0:00) Opening Highlights

(1:40) Intro to Jared

(3:32) Thanks to Notion

(4:39) Start: Being a "Friend" and Bringing Humanity to Serious Work

Mr. Weinstein, we're here.

Jared: (4:39) Mr. Dahl, thanks for coming.

Jackson: (4:40) I'm so glad to be here in the Deep South. As you said, it's not my first time in Alabama, but it is my first time in Birmingham. It's good to be here.

Jared: (4:49) We're excited you're here. We need more Jackson Dahl energy down here.

Jackson: (4:53) It's an honor. We are going to cover a lot of ground today. It's worth setting the context first. You have spent your life across a bunch of different worlds, starting here in Birmingham, then going to D.C., Silicon Valley, spending a lot of time in New York City, and returning to Birmingham. If people were to look at your resume, you lie pretty low, though we're changing that a little bit today. They would infer that you are basically a cold-blooded killer. You seem like somebody who goes into situations, executes with operational excellence, and makes things happen. What they wouldn't see on the resume, but what almost anyone who has ever met you would say, is that you simply radiate warmth. It's a fascinating contrast. I also noticed your logline on LinkedIn is "Founder, Advisor, Friend." One of your former colleagues at Thrive even said that you are a friend in the truest sense. So my first question is, what does it mean to be a friend?

Jared: (6:03) That's really kind. What does it mean to be a friend? I think it means showing up and assuming the best of the other person. It also means listening. I love listening. Frankly, I like listening a lot more than I like talking, which is why this format is new for me. I enjoy championing other people. I love seeing people reach places they didn't even realize they could reach. Playing a small role in helping them do that is incredibly exciting. I get tons of energy from being around others. For as long as I can remember, I've thought about how much other people have supported me. Whether they were peers, managers, or anyone else, they have been incredibly good friends to me along the way.

Jackson: (7:03) There's a related component, though it might not be totally obvious. There are a lot of people who are incredibly warm in their personal lives, but there's a switch when it comes to their professional lives. You certainly know how to get serious when things need to be serious, but you bring a deep amount of humanity into your work, whether in the civic and political realm or in all the work you do here in Birmingham. Everyone you talk to at Thrive says that is a common thread with you. I'm curious how you think about that and where it comes from. Some people cleanly separate these things, but for you, they seem to be a little bit more overlapped.

Jared: (7:52) There were some pretty formative experiences early on, like being in the West Wing of the White House at 22 years old. Our White House, led by President Bush and Chief of Staff Andy Card, was an incredibly serious place, but also a joyous place, even in the most challenging times. President Bush recognized that you have to take the job incredibly seriously, but you can do it with joy and warmth. You get the best out of people if you have a supportive and challenging environment. Chief of Staff Andy Card was a "nice guy finishes first" kind of person, and that set the culture for our White House. It was never about any one person, not even President Bush. He was very clear that we were there for a very short time stewarding the office of the presidency, which the American people expected us to do, whether they voted for us or not. You had to bring your A-game. That applied to the president, the vice president, Condi Rice, and 22-year-old Jared Weinstein. Whatever you were supposed to do, you had to bring your A-game, and you could do that with compassion. President Bush had a great sense of humor. He was in there at 6:30 or 6:45 in the morning, saying that we only had four or eight years to do this job, so we better be sprinting and intentional about what we were trying to do. We could do it with friendship. Twenty years later, I'm still in touch with these people. They touched me in amazing ways and were great mentors to me. That's where I learned it, and I'm glad my Thrive colleagues got to experience and feel that.

Jackson: (9:57) It's interesting. There is a default feeling that as the stakes rise, we all have to become more robotic. Seriousness and camaraderie, or joy, to use your word, don't tend to be correlated. You've shifted it the other way.

Jared: (10:24) I get it. I imagine a lot of my buddies who started their careers in the intense hierarchy of New York City banking learned that behavior. It's not obvious to me that it works. It can get things out of you in the short run, like a dirty fuel orientation. However, for long-term, multi-decade organizational and culture building, it doesn't feel sustainable or lead to long-term excellence.

(10:55) From Duke to the West Wing

Jackson: (10:55) Let's start at the beginning, though. You were in college at Duke and decided to work on a political campaign. I don't know if it was different then compared to today, but it doesn't seem like most smart, ambitious people jump to work in government. What drew you to that in the first place?

Jared: (11:25) I got to Duke in 1998 and learned two things right away. First, there was a sport with a stick and a basket on the end that all the cool guys played, which was not a big sport in the Southeast. Second, in order to be successful in life, you left Duke and worked for Goldman Sachs. If you didn't work for them, your life was basically over. I was willing to sign up for that and thought I would need to work for Goldman Sachs after my junior year. I was a public policy major, which required an internship. I needed to get that done after my sophomore year, so I went to the intern coordinator and asked if I could work for the Bush campaign. Her face changed a little bit, and she said she wasn't entirely sure why I would want to do that. She agreed that if I got there, they would give me credit for my internship. In October of my sophomore year, I started cold-calling down to Austin, Texas. I didn't know anyone, but something about him and what he stood for spoke to me. I wasn't deeply involved in politics, but his career spanning the business sector prior to becoming governor interested me. I was compelled by him, and Austin sounded like a fun place to spend some time. After eight months of cold calling, they rejected me for an internship and passed me to someone else. Toward the end of my sophomore year, they finally called and asked if I was still looking for something to do that summer. I was prepared for an interview, but it was much easier than I expected. They simply asked when I could be there. I told them I could be there in 48 hours and drove overnight. I assumed I would stuff envelopes for the summer and put up bumper stickers and yard signs. By chance, they put me into a really neat office on the campaign with Karl Rove, the president's strategist. I was the low man on the totem pole. By the end of the summer, I was supposed to go abroad for my junior fall. They told me I was doing a good job and asked me to stick around. I told them I was going abroad because that was my plan. They looked at me like I was an idiot and pointed out that I was working for the next president. That led to the campaign, and I continued on from there.

Jackson: (14:05) Did it feel risky? Was it divergent from the norm, or did it feel risky because it wasn't a sure thing and obviously came down to the wire in the end?

Jared: (14:23) It definitely came down to the wire. It did not feel risky. It became a little riskier after we won because I was going to go back to Duke for my junior spring. Some buddies on the campaign started to say, why don't you come to D.C. with us? I thought, drop out of school? That feels a little riskier, at least at the time. Fortunately, my parents, who played such a role in my life, said if this is what you want to do, we support you. The fact that these authority figures said that was an okay path to go on was incredibly reassuring. It still may have been risky, but at least I had loving support to choose what I wanted to choose. Fortunately, one of the more compassionate and kind acts was Karl Rove calling me. He said, I hear you want to drop out of school and come to D.C. with us. I said, yes, sir. He said, Jared, I knew a guy who dropped out of school for politics. He couldn't get his bachelor's degree and he couldn't get his law degree. 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. If I had gone up there, they would have given me a courtesy job, probably in the lead paint division of some department. 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 pretty exciting and special. When I graduated in 2002, he helped create an entry-level job for me.

Jackson: (16:08) What did your friends think, particularly when you were in school?

Jared: (16:11) I don't think the George W. Bush fan club at Duke was that big, certainly during the campaign. 9/11 happened my senior year. His popularity went to 80 or 90% for that year, and people thought of things a little differently. But people were 21 and 22 years old. They were doing their banking and consulting interviews. 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 who pursued those careers. They didn't know what it would look like. I didn't even know whether a job would come until almost the last week of college.

Jackson: (16:57) Interning on a presidential campaign is one thing. Interning in the White House when you're in college is kind of insane, independent of the political party. Were you wondering, how did I get here?

Jared: (17:11) Absolutely. If you don't pinch yourself every day when you walk into the West Wing and through those gates, you're probably in the wrong place.

Jackson: (17:19) Do you think more people should work in government and aspire to?

Jared: (17:23) Absolutely. We have a really special thing here in our country. It's not perfect, and it hasn't ever been perfect, but we aspire for it to be great. It has done a lot of amazing things, and I don't think that's necessarily predestined to continue. The words "for the people, by the people, of the people" often get lost. There are a lot of countries where it's not of the people. We actually have a pretty fortunate thing here. What game or organization have you been a part of where if you don't have the best people, you have a good chance of winning? Whichever president is in office, I hope the best people who are passionate about and believe in that president's vision go join in. I didn't agree with everything President Obama did, but I thought it was great that he brought so many people into government. President Bush not only looked to people he knew from Texas, but people across the private sector. It's an amazing experience. People talk about working in mission-aligned organizations, and they talk about how their Silicon Valley startup is mission-aligned. I think that's true, but you haven't seen mission-aligned until you've worked in government or the nonprofit sector. That's really special. Even if you do it for two, four, or six years in the arc of a long career, you'll grow from the experience, and the country benefits from it.

Jackson: (19:11) You started to talk about it. Your first job was effectively working in scheduling.

Jared: (19:18) Scheduling.

Jackson: (19:20) When you found that out, how did you feel?

Jared: (19:22) It's not the thing that draws most people to government. I got a call a few weeks before graduation, and they said, Jared, we have an opportunity we want to talk to you about. I wondered, is it national security or economic policy? What's it going to be? They said, a scheduling office. I thought, what is a scheduling office? Am I going to be responding to wedding and bar mitzvah invitations from around the country? I think they knew what they were doing. There is no more precious resource at the White House than the President's time. There are so many issues the President could be spending time on, but he needs to be spending time on the most important things. The scheduling office works to ensure that his very finite time is spent on the most important things. We would get all the requests from across the White House for the President's time, and then we'd work with the Chief of Staff. I very quickly got to see what was important. Not everyone at the White House worked across his schedule. They'd work on their narrow issue. I was seeing that we were putting this on the schedule or that on the schedule, so you see what the priority list is. You see who has more power and relevancy at the White House based on getting things on the calendar. It was really helpful in learning how the whole White House worked and what mattered. To the extent I have this operational execution thing that you cited, that was very much the early days of it.

Jackson: (20:59) It's an amazing way to get a bird's-eye view from the bottom in a way that might be unexpected. Have you spent much time thinking about what you did or 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?

Jared: (21:29) Yes. I feel so lucky to have had that experience and that they asked me a few times to take on a next role. I don't know that I would have been the right fit for any president. Part of it was that I was never the smartest kid growing up, but I was smart enough. I was a very hard worker. As early as the campaign, I had bosses who told me stories of how they had been the early person into the office, so I knew I could work really hard. President Bush would call it peacocking, showing your own feathers. That was never interesting to me. I never needed to brag or talk about my work, either inside the campaign or to people out there. Discretion in a White House is pretty important. Whatever judgment a young 22-year-old can show around the job they're tasked to do, I think I had pretty good judgment. There were a lot of balls to juggle, to say the least. They felt I probably did that with kindness and compassion, but also a near-zero failure rate. That led, after a year and a half in the scheduling office, to the President's Chief of Staff asking me to join him as his special assistant. That is a fascinating role because the Chief of Staff is almost the CEO of the White House. His job is to ensure the White House works in service of the President. By the White House, I mean everything from policy formulation and legislative strategy to the communication apparatus, the food staff, the floral shop, the White House grounds, the Secret Service, and the advance team. I had a service orientation of no job too big, no job too small, and do it with discretion. This Chief of Staff was Andy Card, and enough good things can't be said about Andy, as well as our second Chief of Staff, Josh Bolten. Andy treated the President and the janitor the same way. Andy had worked in other White Houses where internal politics didn't serve the administration particularly well. He was very much a one-team, one-dream Chief of Staff. He was there to make sure other people were successful. He was maybe the first glue guy I experienced in many ways. He was first to the White House in the morning, so I had to beat him into the White House to be ready.

Jackson: (24:28) What time did you show up?

Jared: (24:30) I targeted 5 a.m. The alarm went off at 4:12 a.m. Someone asked me one time why 4:12 was such a particular time. I said 4:10 was too early, so I got two more minutes of sleep. If I waited until 4:15, I wouldn't be there at 5. Starbucks wasn't open. I had to stop at 7-Eleven for a good 7-Eleven coffee.

Jackson: (24:53) How much would you sleep?

Jared: (24:55) My guess is I got in bed around 11:30 and popped up.

Jackson: (25:05) And Matthew Walker wasn't pleased with this strategy, right?

Jared: (25:09) No. When you're 22, it's for you. Totally do it.

Jackson: (25:16) At what point did you feel the radical stakes and radical pressure? Presumably, you're working on the campaign. That's one thing when you're an intern. Most people get paralyzed when there are high stakes, let alone a crisis. Talk to anybody who spent time with you, and 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. I'm curious what that was like initially. How did you navigate that when you were 22 and trying to succeed in your first job, where there wasn't room for failure?

Jared: (25:51) In other environments like Silicon Valley, failure is the thing. In DC, failure is not the thing. I was so fortunate to see a campaign that was focused and not finger-pointing. The campaign was a tight race with Vice President Gore. Things came up during the campaign with crisis stories, and the attitude was that we were going to deal with it. I just saw these adults in the room. I realize those adults may have been younger than I am now, but they felt like the leaders of the campaign, and they were cool, calm, and collected. President Bush surrounded himself with people who had been there. A lot of people on the campaign had been in previous White Houses, whether it was in his father's White House or other White Houses. It was an attitude of acting like you've been there before. The night of the election in 2000, Vice President Gore thought Florida had gone for him. There were election parties happening, and they told us we had to stop the party and go back to the campaign because Florida was about to come in. It was not chaos. We had a job to do. We were sending planes to Florida with lawyers, and we were back to our desks. It was as if it was another day of work, even though the stakes were high. I got to the White House in July of 2002, so 9/11 had already happened. There were early signals that the Afghanistan war was already happening. Iraq was on the horizon, which started in March of 2003. When you get there, there is no playing around. The stakes are high. When the stakes are high, those leaders showed up trusting us to do the jobs we were hired to do. It created a psychologically safe environment while still having high stakes. I aspire to create high-stakes environments that are psychologically safe, too.

Jackson: (28:09) You mentioned the White House Chief of Staff being like the CEO. I guess the assumption there is that the President is the CEO of the government.

Jared: (28:17) The CEO of the government, or the Chairman of the White House. The President can't be so in the weeds operationally with everything the government does. The President doesn't decide what color to paint the Navy ships. He doesn't choose everything. In many ways, the Chief of Staff's job is to ensure that the whole White House and the President are teed up to make decisions at the right time. If the legislative session is starting in a few months, are you going through a policy debate process around certain issues? Are you having the cadence of meetings such that the decision is made not too early where it becomes stale, and not too late that it is irrelevant? How do you ensure that the whole thing works and the President puts the right people in place? He chooses the Chief of Staff and his National Security Advisor. With the Chief of Staff, he's really looking for someone who makes the system work.

Jackson: (29:21) To what extent is the White House as an organization like other companies or startups? Part of what you were alluding to is that the President maybe in some sense doesn't do that much. What I mean by that is the President's job is almost explicitly judgment and people. If they're too in the weeds on anything...

Jared: (29:51) You will never hear me say that the President doesn't do that much.

Jackson: (29:54) It's a ridiculous statement in some sense. I imagine it's very costly anytime the President has to go into the weeds.

Jared: (30:04) I think it's very costly for the President to spend time on anything other than the most important stuff. There is a lot of important stuff out there. It's not just stuff in America. The President doesn't get to choose pet issues like libraries or forests. It's not just American issues that get to his desk. The whole world is looking for the President of the United States' view or support on any issue. The White House has to decide, and the Chief of Staff plays a really important role in ensuring we are spending our time on the right things.

Jackson: (30:49) And giving him leverage.

Jared: (30:51) Giving him leverage, but the buck stops with him. The only two people voted on were him and the Vice President. Really, it's the President, so he has to make decisions. He was not someone to throw people under the bus if things weren't going well, especially with staff. It was hard times, obviously. There were challenging times with foreign affairs and the wars. There were challenging times with his polls. The President had to remind us not to focus on the polls or the editorial in the newspaper critiquing him, written by a 26-year-old op-ed person. That's not the most important thing. The most important thing is whether we are operating from principles. Are we making the best decision possible with imperfect information and then executing on it?

(31:45) Riding Shotgun with President Bush

Jackson: (31:45) You were working for the second Chief of Staff. Then you got a call down to the Oval Office. Can you tell me that story?

Jared: (31:57) I was the Chief of Staff's aide and the backup to the President's aide, who was and remains a great friend of mine. If he was ever sick, I would fill in, so the President knew me.

Jackson: (32:13) And this is two or three years in?

Jared: (32:15) This was three years into being the Chief of Staff's aide. The President had to keep going, and if Blake, who was the President's aide at the time, got sick or needed help, you needed a backup who could seamlessly drop in. Blake was going off to business school, so you knew there was a new personal aide likely coming. It was likely that I was going to get the job, but the President needed to consider a range of people and what was best. On May 1, 2006, at 7:04 a.m., my phone rang. It said Oval Office, Karen Keller, who was the President's secretary. She asked if I could come down there. That was pretty normal because I would do tasks for them or take things over. I walked the 30 feet down to the Oval Office, popped in, and asked, "Hey, Karen, what do you need?" She said, "I don't need you. He does." The next thing I hear is, "Jared, get in here." The President was in there with the Chief of Staff, which had moved on to Josh Bolten at the time. He was going through his morning papers and said, "Blake's going off to business school. What do you think about riding shotgun with me for the rest of the administration?" I said, "Let's do it." That was the end of the job interview and offer.

Jackson: (33:43) How was that walk back to wherever you were going?

Jared: (33:45) You got the tingles. As early back as the campaign, which at the time would have been six years prior, something about that job spoke to me. It could have been the show The West Wing and Charlie, who was a character that served in a similar role. It just felt like the neatest job a twentysomething could have. I didn't call my parents a lot during the White House experience. I didn't want to be bragging, and I was worried that if I shared too much with them, they would brag to people. I sat with it for a little bit, and then called them and told them.

Jackson: (34:29) In that job, the President's aide is sometimes called the body man. What actually is the job?

Jared: (34:36) It's not really a job description. It's whatever makes sense for the President. For President Bush, it was deeply understanding his day, the details, and his movements. I can walk through what a day looked like, but you also had to understand his preferences. You wanted him always operating at his best. That didn't just mean the biggest issues. It also meant ensuring from 6:45 a.m. when he gets into the Oval Office until he goes to bed, he has the right information and the right people in there to brief him. He was famous for being punctual, and by punctual I mean 15 minutes early. We were always keeping things moving. He never wanted to be briefed with too much information. He'd ask, "Jared, why are you telling me this?" At the same time, you needed to give him just the right information to be successful.

Jackson: (35:46) You're feeding this incredibly high-stakes, super complicated machine and trying to ensure there are no speed bumps.

Jared: (35:55) As the personal aide, you're trying to do this while remembering you're not the Secretary of State. He would always remind you that you are there to help everyone be successful. "Within earshot, out of camera shot" was our personal aide motto. Stay behind the scenes and make it work.

Jackson: (36:18) How much did you sleep when you had that job?

Jared: (36:20) About the same. I tried to get in by 5:00 a.m. I would get a duplicate copy of his nightly briefing binder, which included his schedule, briefing materials on his events, memos on tax or education policy, and copies of his speeches. Anything he was receiving, I would get a duplicate copy to have with me if he needed it. I would consume it every morning and start to think about whether it was going to work for him. I looked at how the day and the events were laid out. I questioned why we scheduled the press at the start of a meeting versus the end, or why we were handling the Super Bowl champions' visit a certain way.

Jackson: (37:07) Just very minute details to keep the flow.

Jared: (37:10) Keep the flow. If I was in sync with him, I would fire off a bunch of emails in the morning asking people for clarification or suggesting changes. He would come in around 6:30 a.m. and start going through things. He'd ask, "Jared, why are we doing this event this way?" If I had nailed it, I would tell him I saw that issue as well and was working on a change. So much of it was because he wanted to be considerate of others. Everyone tries to do whatever the President wants, but he didn't want people waiting in line for an hour. You had to figure out how to make their experience at the White House enjoyable, rather than just being there to make the President happy. He was welcoming people to the White House. That was what a morning looked like. At 8:00 a.m., the CIA briefers would come in, followed by an FBI briefing and a news communication briefing. By 9:30 a.m., a Prime Minister would be coming in. The press would be there, and he'd need to be briefed for five minutes before that. After that, I'd tell him it was time to go see the Future Farmers of America for five minutes and take a photo. Then we would have lunch with economic policy leaders, fly to Michigan, and I would make sure the helicopter landed on the South Lawn at just the right time so it didn't disturb things.

Jackson: (38:36) And you're the primary interface for all of the things happening.

Jared: (38:40) At a very operational level. I would tell Secretary Rice that he received the information she passed on, since she had her own schedule. The Chief of Staff might ask if we had told him about a certain issue yet. Working with the other staff in the Oval Office and his secretary, we were basically making the minute-by-minute operations and logistics happen.

Jackson: (39:04) How much time did you spend together? I guess it's in these ten-second spurts sometimes, but you're basically with him the entire day.

Jared: (39:13) Unfortunately for him, he had to spend a lot of time with me. You don't sit in every meeting. When he went into a meeting, I would make sure it was working, he had what he needed, and the right people were in the room. Then I would go out and think about the next meeting or get the press ready to come in. We were together most of his waking hours. He would usually go back to the residence by late afternoon to get a workout in and start working on the next day's materials. He would call over for things he needed. 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 was not the most fun part of the job.

Jackson: (39:58) How much consistency and structure is there to the President's time versus just reacting? Obviously crazy things happen and you're reacting, but are most days relatively similar in terms of meeting the CIA guy and then it breaks if there's chaos?

Jared: (40:20) I don't know how other White Houses operate, but he was very disciplined. Everything in five-minute chunks was planned out throughout the day. He ate at the same time, and the briefings in the morning were consistent. You knew his schedule down to an event-by-event level two to three months out. You knew the themes. A theme of a week could have been economic prosperity, so you're going to a factory in Ohio or Silicon Valley to talk about things. However, so many things show up in the world that you have to be prepared for. There's the massive stuff like 9/11, the wars, and the financial crisis. Then there are other things, like a Supreme Court justice passes away, and you've got to be ready to nominate a new one. 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.

Jackson: (41:33) You're very used to diverting.

Jared: (41:35) Totally.

Jackson: (41:36) How many decisions is he making in a day? Presumably, all anybody ever wants is to ask what we should do. Hopefully, some of that's getting abstracted away.

Jared: (41:55) He's making the big decisions. He's certainly making decisions on who is in his cabinet and other leadership roles across those agencies. They're recommending who to put in as the undersecretary for an issue. He is absolutely responsible for the senior staff of the White House, but you don't want him making decisions that other people could make.

Jackson: (42:22) There's also energy fatigue when you're doing these small things.

Jared: (42:25) I don't think the Condi Rices of the world want to be micromanaged either. He wasn't going to be Secretary of State. That was her skill set. You wanted great people in there like Hank Paulson. When it came to our banks failing and our financial markets tailspinning, they brought him a set of recommendations. He wanted to create the environment to get the best ideas and then make the decision.

Jackson: (42:58) In what ways did he model excellence, and in what ways do you think he was a particularly good leader?

Jared: (43:03) I readily admit that no other person other than my parents and grandparents have affected me more positively than George W. Bush. I'll come back to him as a leader, but he's a great father to his daughters. It was really fun watching him as a husband to Mrs. Bush. Their friendship, partnership, and sense of humor was beautiful. He was a great friend. He had dinner before he became president with the same friends that he had dinner with the day after he left the presidency. He wasn't someone that needed to come to D.C. and care about being out at restaurants all night. He didn't sweat the small stuff and focused on the big things: his family, his faith, and the incredible responsibility he was given as a leader. He was incredibly consistent. I knew what mattered to him, what he was looking for, and what he wanted out of me and others. You knew what the bar was. There was no guessing and no ambiguity. His public speaking wasn't always his strong suit, which was unfortunate because that's how so many people saw him. That can lead you to make assumptions about intelligence or judgment. As the White House staff, sometimes we put him in the wrong setup behind a podium giving a long speech. If you ever see him in a general free-flowing fireside chat, everyone says he's funny and they want to have a beer with him. It is fun to be with him, but he is also incredibly wise and sharp. Secretary Rice used to say she would get so prepared for her meetings with him and have every issue dissected and understood. She would come in, and he'd ask exactly the right question he should be asking at the right level.

Jared: (45:45) He's an incredibly acute question asker in a way that's intuitive and gets to the heart of the issue. That's the thing that really matters. It was a skill I really admired. It is also really efficient and doesn't waste a bunch of time talking about things we don't need to be talking about. He did that in a way that was still motivating and inspiring to the incredibly smart people in those rooms who've now gone on to do amazing things in their careers. He is someone that people who worked for him only became fonder of over time. No one's perfect, and he never claimed to be, but you grew in admiration for him as you worked with him more.

Jackson: (46:39) Based on your experience with him, do you have a model of what you think is important in a President that might be different from everyone looking at it from the outside? What leads to success in actually doing the job?

Jared: (47:00) The culture of the White House really matters. Ensuring you have great people who can bring you their best recommendations is crucial. The Oval Office is an intimidating place when the President and Vice President are there.

Jackson: (47:23) How do you ensure you're not getting filtered?

Jared: (47:24) You don't want people coming in and saying, "Mr. President, you look great today. That's a beautiful tie." Sycophantic behavior doesn't help the White House and doesn't help the President make the best decisions. Ensuring you get the best people willing to serve, even if only for a short time, really matters. It needs to be a well-oiled machine. If the President is getting an obvious 90/10 decision, that's a bad use of his time. Other people, like cabinet secretaries, can make that decision. The President should really only get the 50/50 decisions where really smart people are making very good points either way, and you just ultimately have to go with one.

Jackson: (0:00) What do you think people get wrong about him?

Jared: (0:04) One, he's a really heart-led person. He is really compassionate. 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 just loves people, and he loves seeing the best in people. As I said earlier, people say what a nice guy he is, and how they really want to have a beer with him. The "have a beer with him" comment always felt like it was signaling he's just a funny guy to be around. I think it misses how acute of a question asker he is. When it's business time, you snap into business time. It's not because it's in his best interest. He would say, "Jared, this is the United States people we're talking about here, this is serious." I don't think people fully appreciated that. Ultimately, you can debate our White House, but he often talks about how he will be long gone by the time they figure him out, so he can't worry about popularity. You have to make really good decisions. He is responsible and put in place the apparatus to have the information to make all those decisions. I think history will look fonder and fonder on him.

Jackson: (1:38) Obviously related and maybe a similar answer, but I'm curious what you hope he is remembered for.

Jared: (1:44) I hope he is remembered for who he truly is. He loves our country. He happened to be president at one of the most unimaginable attacks in our homeland that really changed how we think about security and things coming to our shores. It wasn't obvious on September 12th that another attack wouldn't happen days, months, or years later. He protected us for a long time. I think he really led with what he believed was in the best interest of the country. 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. He never chased popularity. He would say if you're chasing popularity, it's fleeting. You're going to chase your tail, and it's going to change with the wind. You have to have a set of principles that you follow.

Jackson: (2:53) 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 if anything comes to mind about those people or other folks?

Jared: (3:05) At its best, the White House does attract the best and the brightest. I don't know how I slipped through the cracks, but there were people five, 10, 15 years older than me, separate from the president, that were around. Joel Kaplan was deputy White House chief of staff, and Dina Powell was first in the White House and then went over to the State Department. Two of them are top leaders at Meta now. Kevin Warsh, who's now nominated to lead the Fed, is whip-smart. He would say, "Jared, let me teach you about this." Getting to watch these people, I think when you talk about the president, that feels so far away. He's decades older than you. But to have people who are five to 10 years older, 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, what a total amazing experience.

Jackson: (4:06) You mentioned there are some staff who stay in the White House through every administration. Who are those people?

Jared: (4:17) It's actually the majority of not only the White House staff, but government broadly. There are amazing people who have committed their careers to helping government work. The Secret Service doesn't change with administrations. A lot of national security people don't change. You don't want the people providing you information on what's going on in North Korea to be political. You add political leadership, and that comes and goes, but you want people who keep the organization working. It is an organization, a machine, a company, and that needs to keep working. I've been back there a few times since, and I'll sometimes see Secret Service or other people, and they'll ask, "It's great to see you. What are you doing back here?" It's a really nice thing that despite administrations, there is a set of people keeping the machine going as new leaders come in.

Jackson: (5:21) You mentioned the word political. People outside of politics use political with a negative connotation. I'm curious, particularly in the context of you mostly being in the business world since the White House, to what extent can that word be positive? Is there a time when being political in business is useful?

Jared: (5:47) It's funny, people ask if I think I'll go back to politics, and I feel like politics was the campaign. That feels like politics in a narrow sense. There's politics around government service, and there's certainly a Capitol Hill debating bills with Republicans versus Democrats, but the White House and the issues we had felt like government service. Politics gets laid over that, but it's not really what you're thinking about when you're there. On the campaign, you're thinking about how to win votes and what the poll numbers say. That feels like more politics. I think that probably pushes people away because they think it's all about that. I'm not naive. That is in many ways the sport of D.C., and we see that on the news as much as anything else. But there is a ton of work day-to-day, and the majority of the work is the workings of government. Whether that's the National Park Service, the embassy in Tanzania, or overseeing nuclear facilities, that's government service. That's not politics. I spent a number of months on the campaign, and then I spent years in the White House in service.

Jackson: (7:13) From the outside, it does feel that things are more political across the board today.

Jared: (7:20) Yes.

Jackson: (7:22) You always want to be a little careful of saying this current time is different, but it does feel that way. I wonder if the pendulum will swing.

Jared: (7:32) It does feel different and concerning. It feels like our districts are either getting more red or more blue, and there's less meeting in the middle. It feels more zero-sum, and more oriented toward attacking the person. I had a really neat experience towards the end of my time in the White House when Prime Minister Tony Blair was visiting. The president was busy with some meetings and told me to go check on Prime Minister Blair and see if he needed anything. I thought I would just go get him a water or coffee. I walked out there and he said, "Why don't you sit down?" I thought, "Oh my gosh, what is about to happen here?" We were talking, and he was near the end of his career. I asked him what had changed since he got into politics. His immediate answer was that it used to be very much about debating ideas. Over there, there's a lot of debate; that's part of their system. He really felt like it had moved to more ad hominem attacks on the person. It feels like that's the easier game to play. In some ways, I guess all of us allow that on X and the news. It's easier to play, and it's harder to debate the ideas, but that's actually what matters.

Jackson: (57:12) It's also easier to root for a person than an idea. It's lower hanging fruit.

Jared: (57:19) That's also why a lot of good people ask why they would want to sign up for that. They don't need to have a bunch of arrows thrown at them.

Jackson: (57:29) What do you think D.C. does really well compared particularly to Silicon Valley and New York?

Jared: (57:34) People may chuckle at this, but I left less cynical than I arrived. You can look at D.C. from the outside and feel pretty cynical about it. We talked about the career people in government. They are deeply committed to doing a job for our country. People are really trying to get to the right answer. I believe that is true even at the highest political levels. Unfortunately, the system does move you to horse trades and negotiations, which is not great. However, it is really mission-aligned. In the other markets I've lived in, there is ambition and excitement in New York, and there's certainly a future-looking frontier in Silicon Valley. But mission alignment is real in D.C.

Jackson: (58:31) People would say that Silicon Valley is super mission-aligned. You've made that comment twice now that there's a different weight to the mission.

Jared: (58:39) Great organizations in Silicon Valley have missions, and that is a positive force. In my time with Palantir, I saw very hard software data integration and analytics work. That company helped remind people that despite the difficult work, there was an exciting mission behind it. I just think it's a different level in D.C. At the time I was in government and then left for the West Coast, the connectivity between Silicon Valley and D.C. was like speaking different languages. Now there is more connectivity in an exciting way.

(59:27) Starting Over Out West: Post-WH, Stanford, and Palantir

Jackson: (59:27) You worked for the President briefly post-White House, and then you decided to go to business school. Before we get into where you decided to go, I'm curious about the theme of risk. What was going through your head at that point? What felt like the obvious choice? Did business school feel risky, or did you feel like you had to go do something different?

Jared: (59:51) The President was very much a sprint-to-the-finish kind of leader. A lot of us were deeply committed. We had the financial crisis and wars going on, so we were sprinting to January 20, 2009. We were also really committed to setting up the White House for whomever became president, which was ultimately President Obama. It was all hands on deck until the last day. When January 20th came, I was the last person in the Oval Office with him while President Obama was getting inaugurated. We went up to Capitol Hill and then flew back to Texas that day. Everything was gone from Texas. All of the military trailers and the situation room were gone. I stayed in a motel that night, which was very different from where I would have stayed when he was president. What was really fascinating is that President Bush was president until 11:59 a.m. I was his personal aide, and right at 12:00 noon when President Obama was sworn in, my BlackBerry stopped working. They just switched over to the new administration. The timing was really interesting because the next day, the 21st or 22nd, business school notifications came out. It felt like my next chapter was starting.

Jackson: (1:01:23) You mean admittance notifications? So you had already applied?

Jared: (1:01:27) I had applied in the fall of 2008. I remember going into the President's cabin on Air Force One around August or September and telling him I was thinking about business school. He asked if I wanted him to write a recommendation for me. I told him I would be honored and it would mean a lot if he was open to that.

Jackson: (1:01:45) That probably helps.

Jared: (1:01:47) It was nice. He wrote a long, handwritten note to both of the schools I applied to. I also remember saying to him that if he was open to it, I would be honored to come to Dallas and help him build his post-presidency. He was taken aback in this really kind and humble way. He asked, "You'd do that?" For him, it was obvious why someone would work at the White House in support of the President. But to go and work for him post-presidency, he was amazed that someone would be willing to come down there and help him in his new chapter. In addition to sprinting to the finish during the fall of 2008 and early days of 2009, we were also building his team in Texas. His prior aide, Blake Gottesman, had gone off to business school and then came back to the White House for the last few months of the administration. We teamed up to think about the Dallas office and his post-presidency. I thought about people in the White House who could come down there. There were people the President probably knew or had seen around the White House but didn't know well. I would suggest who could be his assistant or his chief of staff. That was really fun. It was my first organization-building experience in many ways. It was really neat because the President appreciated me, but he knew me as his personal aide. Then we got to Dallas, and the Condi Rices, Karl Roves, and Hank Paulsons were gone. He realized he had me and Blake to figure this out. For me, it felt like asking how the mighty have fallen now that he had to rely on us. But we built a really good team down there. We also started thinking about what this post-presidency institute and life would look like for him. Presidents usually build libraries and similar institutions. We hosted a session a month or two after he left office where a bunch of former advisors came down to discuss what the Bush Institute could look like. I remember one of his good friends raising his hand while the President was in the room. People had been talking about doing a think tank and things of that nature. His friend said, "Mr. President, with all due respect, a George W. Bush think tank doesn't really seem on brand for you. It should be the George W. Bush let's-get-something-done tank." It was a joke in many ways, but it highlighted the need to build something focused on action rather than just putting out white papers. The President is not a white-paper kind of guy. That was an incredible six months where I developed a really new relationship with him. I'm really glad I did it because it completely changed my friendship with him. Then the summer of 2009 came, and it was time to figure out business school.

Jackson: (1:04:59) You had applied to business school before. What was the calculus on whether to double down on D.C.? When you applied to business school, were you thinking you would go back into politics? How were you thinking about it?

Jared: (1:05:16) If you think back to college, I was drawn to work for this president and see where this journey took me. What initially drew me to George W. Bush was that he had a career in business before he went into service. Yes, it started in my twenties, but there were two other personal aides before me in the White House, and they had all gone to business school. The president had gone to business school early in his career. I was less cynical about D.C. than when I arrived, but I still wasn't sure that's where I wanted to spend my whole career. I had an incredibly rich experience. My desk was ten feet from the Oval Office. I wasn't sure I wanted to be a junior lobbyist in town or work on Capitol Hill at that point. Maybe it would come back at some point, but I knew I wanted to do something different. I wanted to try the private sector. That's broad, and I didn't totally know what that meant. I was a little nervous. The easy job for me in the private sector would have been going to work as a chief of staff to a CEO at Facebook or Goldman Sachs. That wasn't the direction I wanted to go. I didn't want to do the same thing I had done for a private sector leader that felt a little administrative or too paper-pushing. Those are important jobs, and the chief of staff role in the private sector has certainly evolved, but I didn't know. I thought business school was an interesting way to take a pause. Yes, you're in class, but so much is coming at you from incredibly impressive peers who have come from different industries. You get a chance to think about the landscape before you make your next move.

Jackson: (1:07:19) It's also a structured sabbatical. I'm sure on some level you felt that way.

Jared: (1:07:24) Especially at Stanford. There was a great line from a dean of Stanford: "You are out here in Silicon Valley. Don't let school get in the way of getting an education." You go to class for twelve to fifteen hours a week. I was working eighteen-hour days in D.C., so you have plenty of time to explore and soak up all that's in Silicon Valley.

Jackson: (1:07:47) How was your ego at that point coming in? Presumably, one person's reaction to where you were coming from would have been, "I can do anything, I literally just worked for the most important person in the world." Did you have a feeling of that? Or were you thinking you actually didn't know anything about the business world?

Jared: (1:08:07) I was the personal aide to the president. I don't know that I had the feeling that I could do anything. I probably had a little fear that there's a big world out there. I didn't think I wanted to stay in the world that I was actually pretty well suited for. After that experience, I wanted to do something else. I wanted it to be big and bold. What I most loved about the White House that I wanted to take elsewhere was that it was big and bold. I was looking for another stage that had that. I didn't yet know exactly what the stage was, and I didn't know what the role would be.

Jackson: (1:08:41) Why Stanford? In some sense, it was very far away from D.C.

Jared: (1:08:45) It was far away from D.C. Many peers had gone from the White House to Harvard Business School on more of an East Coast path. Especially for the kid from Alabama, people knew Harvard much more than this out-West path. It did feel far. There was probably something to the fact that it was different. It had a less-known aspect to where I grew up, and it felt like it would stretch me differently. Harvard is an amazing place, and I have great relationships with people there, but it felt like Stanford was different. When I went out there, it just felt right. I'm glad I ultimately made the decision to go there. When I got there, it was a very uncomfortable pair of pants at first that became my favorite pair of pants. I was much more used to what I would call East Coast ambition. I think of East Coast ambition as, "I'm on floor seven and I'm trying to get to floor 57," the top office. West Coast ambition felt to me like, "I don't even want to be in that building. I want to build my own building." That was very new to me. Within a few months of being at Stanford, I realized this was new, different, and stretching me in a neat way.

Jackson: (1:10:18) That's a great metaphor. I'm curious about anything else regarding the culture of being in that world that has stuck in your mind.

Jared: (1:10:26) I think about what real risk is when you get out there. People from back home or D.C. would say to me, "You're at Stanford. Have you been to Google yet?" To them, Google was a startup. At that point, it was already a public company. Out there, people viewed Google as the old empire. A startup is two guys in a garage working on Red Bull and Cheerios, building the thing. Seeing that normalized was incredible. I had never seen startups and that kind of behavior. It's pretty cool to be on your third startup and to have failed. That's not a failure out West. That was a completely new thing. Even in New York, being a failed hedge fund manager isn't a particularly championed thing.

Jackson: (1:11:28) What drew you or how did you end up falling into the Palantir situation? What was unique or special about those guys?

Jared: (1:11:36) I had a classmate who became a friend, a guy named Steve Laughlin, who is now an Accel partner. He started a company called RelateIQ after business school. 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 there were some guys he thought I would enjoy meeting. This was within a month or so of getting out to Stanford. We had a dinner with Joe Lonsdale and Shyam Sankar. I thought, "Man, I don't want to have anything to do with walking software through government. That's not interesting."

Jackson: (1:12:09) That'll pigeonhole me, almost.

Jared: (1:12:10) That'll pigeonhole me. I just left that for the sole reason of coming out here. They said, "Come by the headquarters. Let us tell you what we're doing." Then they asked, "Will you map DC for us?" I said, "Guys, I may be the best person to do this within a half-mile radius of Palo Alto, but I'm not actually the best person. I've got a bunch of friends who would probably love to do this for you." I introduced them to some people in D.C. that I thought could help with national security, like congressional strategists and lobbyists. I forgot about it for a few months. Then I ran into Shyam somewhere in Palo Alto. He said, "Jared, those were incredibly helpful people. You've got to come let us tell you more about what we do. Maybe there's something you could be helpful on." I said okay and went there. The headquarters of Palantir was right in downtown Palo Alto at the time. They told me more about what they were doing in government and national security, but also the early days of some private sector work. I thought it was pretty interesting. The timing was interesting because all the Bush administration people had gone off into the private sector. They were now in big banks or pharmaceutical companies. I thought maybe we could just show them what we do and see if it was interesting to them. It seems so obvious now, but the idea of an upstart data analytics company like that was not obvious then. Things got going, and Shyam said, "We really should give you a consulting contract." I told him I didn't need that. He said, "You can get stock options." We didn't even have bonuses in government, let alone equity. I didn't really know much about it. Now I'm glad I took the stock options. It was really neat because it was certainly an engineering culture at its core. That was totally new to me. I had not been around that world at all. I certainly hadn't been around the reality that things are messy and don't work perfectly well right away. There had been one government software project in my world at the White House, and it involved 17 months of contractors. Palantir was building things in days.

Jackson: (1:14:28) How credible did you think Palantir was? Thiel was involved, but certainly not as high profile as he is now. Were you just thinking, "I don't know, there are startups, I might as well help"?

Jared: (1:14:41) It was really interesting because we were making some interesting progress. We would go to these banks and I teed up some conversations. We were doing some interesting work during the mortgage crisis, helping Bank of America and JPMorgan work through their issues. Palantir had gotten into those banks through security, because that's what they were known for. But security was a much smaller problem than their mortgage book, and we thought we could help work on that. I remember we went down to LA for a meeting with Countrywide, which Bank of America owned. It was some engineers that I was friends with, Shyam, and Karp. Then Michael Ovitz showed up.

Jackson: (1:15:28) On his way in, as always.

Jared: (1:15:30) Michael Ovitz is someone I had admired since I was a kid. I was wondering what was going on here. It was a little difficult for me because I didn't know how to assess software.

Jackson: (1:15:41) You didn't have a bar.

Jared: (1:15:42) I didn't have a bar. I thought the people were incredibly sharp. There was mission alignment. But I wondered, am I selling or advocating for software? Does this stuff even work? The messiness of it is often more a feature of Silicon Valley. That was new for me, to not have it be perfect on day one.

(1:16:05) Meeting Josh Kushner and Building Thrive Capital

Jackson: (1:16:05) I suspect that was also very useful. It was almost like a crash course on a bunch of things that would go on to be useful for understanding this world. We kind of skipped over it, but I believe you went to Harvard orientation and you met somebody, despite not going there.

Jared: (1:16:22) That's true. I went to what is called Analytics at Harvard, which is the pre-class for non-finance people. They get you up the curve.

Jackson: (1:16:36) Almost like a boot camp.

Jared: (1:16:37) It's a boot camp. There were four or five sections, which is about 100 people. You're assigned to a section in one of those five classrooms, and you have an assigned seat. I got to the section, turned to the guy next to me, and said, "Hey, I'm Jared Weinstein." He said, "Hey, I'm Josh Kushner. What's your story?" I said, "What's your story?" Over a week, he became my buddy at Analytics. At the end, he may have taken it a little personally, but I said, "I like you. You're great, but I'm going to Stanford." He had a quick career in banking, spending a year or two at Goldman before coming to business school. I was coming from the government. We connected because we were both big dreamers. I could see his ambition at an early age, and he had seen my experience. We both come from Jewish immigrant families. We had different stories, but we also just liked each other. I told him I was going to Stanford, but that we should keep in touch. I had no idea what he would end up doing. He wasn't really doing venture investing at the time.

Jackson: (1:17:56) He was super young, right? He was 24.

Jared: (1:17:58) He was 24.

Jackson: (1:18:01) In some sense, you were both slightly abnormal in that you hadn't really worked in a real environment.

Jared: (1:18:08) Are you saying the White House wasn't a real environment?

Jackson: (1:18:09) In some sense, yes. It wasn't a standard environment. The president doesn't do anything. Did you guys stay in touch?

Jared: (1:18:21) Initially, we texted. Then there was a totally serendipitous moment over the holiday break of that first year. I texted him asking how his semester was. He said it was great and that he was in Miami. I told him I was also in Miami. We happened to be at the same restaurant with our families that night.

Jackson: (1:18:40) That was a weird twist of fate.

Jared: (1:18:42) So weird. We caught up. The next summer between our two years, I came to New York for his 25th birthday. It was a paintball tournament. A lot of his friends that I still see, like Chris Paik, were there. None of this stuff was on the horizon. Halfway through our second year of business school, we stayed in touch and had brunch in New York. He asked what I was thinking about doing after school. I had done a private equity job, been doing a little bit of the Palantir stuff, and almost went to do a COO track at a hedge fund, Viking Global. I was interested, but I didn't know what I wanted to do. We were talking, and he said, "I'm thinking about building a venture capital firm. Would you ever want to partner with me and do that?" He had one year of investment banking experience, and I had seven years of government experience. I thought, of course we should start a venture capital firm. That's so obvious. But he had some good reasons for doing it. He made a really compelling case for the opportunity to build a firm in New York. We talked about how we complemented each other with our experience. Maybe we didn't have any business starting a venture capital firm, but I don't think that is really the bar. We wanted to do it. We were ambitious, excited, and passionate about it. We stayed in touch over the next number of months. He was talking about raising this first institutional fund, and ultimately said this would be an exciting thing to do.

Jackson: (1:20:28) Sounds like you and Josh knew each other relatively well, but not that well. What was special to you about him? He knew other people at Harvard. Obviously, you had some credibility—or maybe a ton of credibility—in a different world, given your past experience. What do you think it was value-wise, competence-wise, or ability-wise that allowed you to work together? You guys hadn't worked together before. Why was that the draw?

Jared: (1:21:01) I was really drawn to Josh's curiosity. He talked a lot about why there was an opportunity to build a New York-based, early-stage venture capital firm. Josh would talk about how this is the most change since the Industrial Revolution. It was exciting. He had made some early angel investments in companies you were starting to know about. Then you just think of the concept of a venture capital firm, which is that we are going to go meet all day with people who are optimistic, ambitious, and think they can change the world. You get to help them do that, not only with capital, but with advice and support. That spoke to me. We started to have LP conversations, and it looked like it was going to work out. I saw that he could set a big ambition and bring other people along. Chris was thinking about joining. Will Gabric, who's incredibly sharp, was joining. Both the excitement and the unknown of it were exciting to me. As for what he saw in me, you'd have to ask him. I think he saw someone who understood hard work from the White House experience. He saw the trust, the ability to juggle tons of balls, and the ability to build a real organization. I'm so grateful we found each other and decided to do it.

Jackson: (1:22:53) I don't know how old Will is, but those guys were kind of kids. Was there an element of wondering if you were getting in here with the rugrats? Obviously, you were probably around 30. Were there other people in your life who were questioning if this is what you were going to go do?

Jared: (1:23:12) I think there were people saying, "Oh, that sounds cute. Start your own little venture capital firm."

Jackson: (1:23:17) Also in New York, where there are more venture capital firms.

Jared: (1:23:21) I think there was a little of that. I ultimately had to trust my instincts. I took some time to think about it. Palantir was interesting, and I did stay involved with them for a number of years, but Thrive was exciting and it was fast. It was very different from the White House, obviously. But between Chris, Will, and Josh, I think all four of us realized this was a committed, smart, driven group of people. We wanted to see where it could go.

Jackson: (1:23:56) It's interesting on the theme of risk, because in some sense, you could say that the White House is the highest pedigree thing you could imagine doing. I realize it's different for a lot of reasons, but at the very least, it is consensually a place to be. This was the exact opposite.

Jared: (1:24:16) It was at the time. Our brand was below the radar for a long time, too.

Jackson: (1:24:23) After you've had a little bit of success in your career, there is a bit of scarcity that can be tempting to have. You start thinking, "Wow, I don't really want to climb down from this local maximum, and I have to parlay this into the next thing lest I fall." Granted, it wasn't a straight line. You had gone to business school and there was Palantir. But from the outside looking in, that was super risky, or at the very least taking a huge step down to try something.

Jared: (1:24:59) It felt like a different step, not a step down. I remember saying things like, "Gosh, in some ways I hit a grand slam with the White House, and my biggest fear is I don't know what the next one could be." Not knowing was scary. I saw the potential in Thrive. Years in, we used to say, "Can you believe we got here?" Or people would say, "Can you believe this thing that was so small when you started?" Yes, we wanted to build this. Did we have any business doing it? No. Did it take 15 years? Yes. But at least we were aiming to do something really great. That was inspiring and worth trying.

Jackson: (1:25:49) Did you know what you were aiming at? Was there a reference point? Did you know about Sequoia Capital?

Jared: (1:25:53) Yes, there were people like Tiger Global. What they had built was pretty inspiring in 2010. One of the things we got right was balancing ambition and doing something different with a ton of curiosity and admiration for those who had done it excellently before us. I had come from zero finance background. My only finance-adjacent experience had been at the White House in 2008 when it felt like Wall Street was burning down. So I had a little bit of skeptical curiosity as I dove into the world and started building Thrive. I was a student of what people had done. I would go and ask people if I could sit in on their Monday meetings. The good thing was we were not a threat to anyone at the time. We were curious and wanted to partner, maybe writing a small check alongside Sequoia or Tiger. I'm really grateful that so many people supported us along the way and let me learn from them. To Josh's credit, he believed it was good to know those things while also doing things differently. I think we balanced those dynamics of the firm really well.

Jackson: (1:27:22) It takes a certain kind of conviction and self-knowledge to know where to toe that line. Why was being in New York important?

Jared: (1:27:32) That was more of Josh believing it was a market to start in. He knew the market there. Josh has seen a lot of things early and made good bets, and there was a feeling that this was an emerging ecosystem. It was also exciting to see back when software was more of a category, versus what it is now. Traditional industries were getting enabled by software. There was entertainment, fashion, and healthcare when we started Oscar. Our core competency was perhaps an interesting way of thinking about enabling these traditional industries. For a while, that was a theme Thrive very much leaned into.

Jackson: (1:28:25) Aside from a couple of things you just said and that group, which in hindsight was obviously quite special, is there anything else you guys did early on? Structurally, culturally, fund setup, LPs—is there anything you think was really important in hindsight, even if it wasn't completely deliberate?

Jared: (1:28:50) I think there were a number of things. First, no one outworked Josh or me. As the two top leaders, we were not advanced in our careers, just sitting back and letting other people do the work. Setting that example was really important. I refused to ever use the word back office at Thrive. I never understood that as a finance term, where there's an investing team and then there's the back office. It seemed so demeaning to me. At the White House, we didn't have the important people in the back office; we needed excellence. I wanted us to have the best investors, absolutely. But I also wanted the best general counsel, the best CFO, and the best receptionist. Bringing that intentionality to how we find great talent, while maintaining a one-team orientation, was super important. I wanted the executive assistants in the room as much as possible during investment discussions. Not because they would advance the discussion, but so they would have better context of what we did and could show up more. We had great custodial staff and a wonderful man named Ramon who made our office great. There's that great NASA story of President Kennedy walking through the halls and running into a janitor. He asks the man what he's doing here, and the janitor says he's working to put a man on the moon. Everyone plays a role in the mission, and I wanted that kind of culture there. Josh always asked why we had to do things a certain way. He was always good at questioning things, but also open to the answer of why. He trusted that I would drive that forward, or that we would think differently about things.

Jackson: (1:30:54) One of the things I alluded to earlier, which certainly comes up when you talk to 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 post-business school. Was it just that any crisis or stakes felt tame compared to what you'd done before?

Jared: (1:31:23) Some of our Thrive colleagues would say you have to see crisis management Jared. When Will left for Stripe, people wondered if it was really a crisis. It didn't feel like a crisis based on what I saw at the White House. It's something different and unexpected that you have to manage, but going into panic mode never felt like the right strategy to effectively solve it. If something happens with a company or an LP, you just get grounded in what is actually going on. You figure out the next step, and the step after that. The sun will come up tomorrow. You need a little bit of self-trust that we got here and things will be okay. Let's get back to our values. It's never as bad as it looks, and sometimes it's never as good as it looks either. I try to stay level-headed. I'm glad my colleagues enjoyed seeing me in that.

Jackson: (1:32:39) It's funny, it's almost like when you've experienced a certain kind of pain. Everyone's worst pain they've experienced is the worst possible to them. It's all relative.

Jared: (1:32:53) When I got a call from the Situation Room in 2006 or 2007, and they asked if I could track down the Chief of Staff because the Vice President had shot somebody on a hunting trip, that felt like something important to manage and stay calm about. Some of the Thrive stuff didn't really feel like that.

Jackson: (1:33:16) When it comes to any kind of time-based, intense period, do you have any advice on how to think about that? Assuming you have the self-trust and confidence you mentioned earlier, what about the tension between collecting information, seeing the chips on the board, and the speed of action? How do you calibrate that?

Jared: (1:33:50) It depends so much on the situation. Humans are capable of a lot of things, and we probably don't appreciate that. It can be paralyzing, but you have to move forward. You often have more information than you realize to take action. I'm probably guilty of that too in a number of cases. At times I try to capture all the information. When I look back, I realize that with the initial 80% and your instinct, you could have acted.

Jackson: (1:34:29) How important was vision over the course of building Thrive? At what points was it incremental, and at what points did it have different eras?

Jared: (1:34:49) In some ways, our vision has never changed, which is to be an exceptional firm for the time period that we're in business and be a part of the most transformative companies. It took us a while to name it that way. It's now expressed as being the most impactful partner to the most transformative companies. Whether we could articulate it or not, that was consistently what we were aspiring to do. In the early days, you couldn't always get into the best companies. We weren't the most impactful partner yet, but we were looking toward that. Over time, the industries that were most interesting changed, and our scale and ability to invest changed. That has always been the orientation of the firm. The firm has been stubborn on that vision. One of the takeaways I have from the Thrive experience is for an organization and for individuals to stay super stubborn on your vision. It's your vision, it's your life. Don't live someone else's dream or vision. Own it and be selfish about your vision. The other thing people and founders get wrong is being stubborn on their strategy. Don't be stubborn on your strategy. Be flexible, nimble, and adapt. Thrive was very good at adapting. Think of all the founders who start with something and want to operate in a certain way, but the initial product wedge or the go-to-market strategy doesn't make sense. That's where adaptability and flexibility really need to exist.

Jackson: (1:36:48) What makes that place so good at identifying talent early? It broadly seems to still be true today.

Jared: (1:37:02) It's a great question. In some ways, I wish it were more scientific because then it would feel like something.

Jackson: (1:37:10) But it does seem repeatable.

Jared: (1:37:12) It has been repeatable. We maybe didn't overcomplicate it. We asked, who are your smartest friends? Go ask them who their smartest friends are, spend time with those people, and see if they are a values fit for the firm. Intelligence matters, but work ethic is a real thing at Thrive, and you wanted to see people who demonstrated that. I remember talking to a Sequoia partner one day about talent. The framing was to look at their past career. People will explain away things, but did they make good decisions? Did they choose the right place to go? Have they won before in sports? You can make a bunch of excuses for why things didn't go someone's way, but there's something about making the right outcome happen in whatever situation they were in. There was this orientation that nothing is given to you and you have to make it happen or create it. That's very much the immigrant mentality aspect of Thrive. We used to talk about how our biggest fear would be the person who joins because Thrive has made it. Thrive always had more of an orientation that we want to storm the castle, not be the castle.

Jackson: (1:38:52) That's going to be an interesting challenge for them over the next decade. I'm long the firm from a leadership standpoint. How did you go about maintaining that incredible rigor and high bar while bringing in the warmth, humanity, and camaraderie that we talked about earlier?

Jared: (1:39:15) I don't think we were ever going to lower our bar. The risk was more that we lowered our humanity, camaraderie, and compassion. Kindness is honesty. Kindness is pushing someone, not letting people get away with stuff. I thought we would get the best out of people if we were one team aligned around a mission. If I could play a role in helping everyone at the firm be the best version of themselves, and if we had chosen the right people, then that would lead to good outcomes. There was a little bit of an Andy Card, White House Chief of Staff role—my job is to make everyone else successful. It was a Shane Battier kind of orientation. We did a good job with that.

Jackson: (1:40:15) What was the Monday question?

Jared: (1:40:17) The Monday question was an attempt to take our jobs seriously, but not always ourselves seriously to that point on our humanity. When COVID started, we were all on Zoom in disparate places. It became a little monotonous just giving updates, and it was exhausting.

Jackson: (1:40:45) Very transactional.

Jared: (1:40:46) Very transactional. You miss being in the office with everybody. My idea was to ask a different question of the whole team to start off Monday. I even used the Patrick O'Shaughnessy question: What's the kindest thing anyone at Thrive has ever done for you? I asked about favorite pizza toppings. There was silliness and funniness, but it was about recognizing that we are people who like each other and need to know each other. We weren't in each other's lives as much as we had been when we were all in New York. At that point we were 40 or 50 people.

Jackson: (1:41:30) It was like just going on a Zoom.

Jared: (1:41:33) I'm grateful that people leaned in. There was some eye-rolling at times, but even for the eye-rollers, it ended up being great. We used to ask people on their first day what their favorite Girl Scout cookie is. I think this question has remained, despite Josh fighting it. It's a ridiculous question, but let's keep things light. Other firms would tell me they heard about this Monday question and that it felt like a great way to keep the team engaged. I thought about trademarking it.

Jackson: (1:42:03) The little things.

Jared: (1:42:04) Little things.

Jackson: (1:42:05) In what ways did you and Josh use healthy competition amongst the young stable of star investors? What is the balance there? Venture capital is a weird thing. Thrive, and many other great firms, talk about how it's one firm and one team, but in some ways, it's a little bit like a swim team.

Jared: (1:42:39) I tried to fight that. I never wanted us to apply for the Midas List, for example, because we all worked on deals. Maybe someone sourced it, someone else supported underwriting, and another person helped win it. We were always meeting and discussing deals. We were getting on the phone at midnight and flying places as a group to sell ourselves to people. We didn't really focus on competition. It was more intuitive around performance. We wanted everyone to feel like they had their own path at Thrive. Everyone came from different backgrounds with their own trajectory. We told them not to compare themselves to someone else. Of course, these are competitive, ambitious young people. They will compare themselves; you don't have to encourage them to do that. The people that succeeded at Thrive over the long term took the long view. Their goal wasn't to do a deal in their first six months. It was about learning the strategy, the orientation, and the way the firm shows up. They wanted to learn how the senior people underwrite and win deals, and how they support companies. If they could meld their own intelligence and style with that, they could ultimately get their sea legs and go do their own thing. Think about people like Kareem, Miles, Vince, and Philip. They started and were willing to say, "This is a great place for me to be. I have a lot to learn, I have a lot to bring, and I'm going to play the long game." Look at how successful those guys have been.

Jackson: (1:44:32) And all in pretty different individuated flavors.

Jared: (1:44:36) Totally different flavors.

(1:44:37) Founders, Humility, and the Three-Body Problem of Ego, Ambition, and Impact

Jackson: (1:44:37) As a very human-oriented, people-oriented person, I'm curious what your lens broadly is on great founders and great companies. To what extent can you understand or even underwrite an investment by understanding the people inside of a situation?

Jared: (1:44:57) Every investor has a different flavor. What I loved about my investing time at Thrive was the founders I got to back. A lot of people say you need ten years before you know if you're any good at it or what you're good at. As the firm scaled to more growth deals, I found myself still gravitating towards early founders and being that first call, first partner. I love listening. In the early days, you have to be careful not to dictate to a founder exactly what they should do. You really have to listen and put yourself in that seat. There are a lot of great people who start businesses that don't work out, so I don't think it's only a founder thing. They have to make the right decisions on their business and their product. A lot of mistakes we made at Thrive were probably choosing the wrong setup for a founder. Ideas are amazing. I love inspiring ideas, concepts, and visions, but leaders have to make them a reality. People talk about product-market fit, but there's also founder-opportunity fit in many ways. Is this the right founder? There are so many different kinds of founders out there. There are consistent things: tenacity, the ability to learn, and growth-oriented aspects. But then it's very dependent on the opportunity.

Jackson: (1:46:30) There is a thread that is quite applicable to your time at Thrive, but broadly applies and is certainly relevant to the work you do today. I mentioned it briefly earlier: being an amplifier, a confidant, and an advisor. You continue to find yourself in this role. I want to get to the person-situation fit and the self-knowledge that allows somebody to flourish. One place to start that came up as I was talking to people was the way you seem to enter situations with a great amount of humility. Not in a "woe is me" way, but specifically asking: What do I not know about this? What knowledge and context do I have to gain before I'm ready to bring a point of view forward? I'm curious to what extent you've identified where that comes from. Is it a White House thing? Is it an Alabama thing? Is it a faith thing? Is it a family thing?

Jared: (1:47:42) That's a really good question. Maybe I could be better served by having blind confidence that I just know the path and will figure it out. I feel like I'm rarely the expert on anything. My career has been very horizontal across different things. I bring a similar skill, orientation, or disposition as a leader to those things, but I've got to learn the context of the place. Everyone has their own reality. Even within Thrive, someone might feel they deserve a certain compensation or that a deal is right, and you don't know. You have to pull out, try to drive for the best conversation, and be curious. I remember in the early days of Thrive when Chris called me and said we had passed on Twitch. He said we were making a mistake. I told him he had done a really poor job of articulating why it was interesting and that we needed to talk about it because I wasn't hearing it. I wasn't saying it was uninteresting, and I actually believed in his conviction, but the rest of the team wasn't deep in the space. By creating a container and a place where he could better articulate it for me, it allowed him to then better articulate it to the team. He went back to the team and ultimately did the deal.

Jackson: (1:49:08) I have a similar question around a service orientation and broad-based generosity. It's a hard question to answer, but I'm curious if there have been influences in your life that you can trace that back to.

Jared: (1:49:24) My hero is my grandfather. 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 had a really big heart. People would over the years tell me how much they loved my granddad and how he was always so kind to them. I always experienced him as silent, but he was magnetic in a really inspiring way. My parents were certainly philanthropic in a certain way. As I said earlier, working for President Bush, he had a huge heart. I see the best in people. I don't want to confuse that with being too naive to people's motivations, but I do see the best in people and I hope for the best in people. Through all those experiences, sometimes I can look at a situation, see where someone is in their own way, and talk them through to a better place.

Jackson: (1:50:33) One of the things that continues to come up with anyone who has benefited from you as an advisor is that you are deeply empathetic and understanding, but not soft. There is this unique tension. Chris Paik put it as caring with the right weighting about the people and the outcomes. There are people who swing to one direction or another, but that balance is really effective. Another way of putting this is that most people hedge because they're concerned about how you're going to react. You don't hedge, but you're on the person's team.

Jared: (1:51:12) I'm more interested in being effective than being right. I've certainly not always been effective. As an empathetic person and a good listener, I have a good combination to understand where the other person is coming from. I find myself oftentimes setting the table for conversations that have more of that tough love and directness. I've grown in the ability to be direct. Being on the nail but not being effective feels like wasted energy. My instinct on what the right answer is is almost the easy part. The challenge is figuring out how to take this other person on a journey to that point. I probably don't get it right as much as I would like, but that's the orientation.

Jackson: (1:52:24) Your advice is shaped to the receiver. That connects to another element of what you were just saying: understanding that the answer may not be as important as the delivery. You are good at not projecting yourself into the situation. You're just giving it a clean inspection. It's a combination of being incredibly personal and somewhat impersonal, having distance.

Jared: (1:53:03) Especially now as I'm more in these advisor seats, I deeply care about them, but I'm in some ways dispassionate to the situation and able to give clearer advice.

Jackson: (1:53:19) It seems 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 path they already want to take.

Jared: (1:53:34) One of the kindest things was when I stepped back from Thrive, Josh called me and said, "We have something for you." He had put together a book of letters from everyone on the team about the role I'd played or where I'd been most helpful. It was neat because there were individual stories, but there was a thread to this topic that I didn't fully appreciate until I got the book. The thread was that Jared sat on the same side of the table as me. Even if he was technically on the other side, or he was my manager, or we were in a disagreement, I always felt he put himself on my side of the table and tried at a whole human level to get the best of the situation and the outcome. That was really nice to hear. It was interesting to digest that, reflect on it, and see that maybe there's something you can lean into more. That meant a lot. I'm glad people benefit from that and find it valuable.

Jackson: (1:54:45) It's sort of a benefit of the doubt. It's what you said earlier. It's seeing the best in people and then also saying you can be better.

Jared: (1:54:57) Yes.

Jackson: (1:54:59) Do you have any advice or thoughts on that? Most people really struggle with saying the hard thing or moving into conflict, in part because it is wrapped up in so many of these emotions.

Jared: (1:55:12) It is really hard, especially when they're wrapped up in the situation or it's not a great environment. Saying the hard thing is almost always the right thing to do. It's almost known by everyone, too. When you get to the other side of it, everyone's almost sad that it has come out, even if it's a little shocking, because it's probably the truth and it needs to be said. It's usually not meant personally, but it's important. Delaying those conversations just breeds worse energy or resentment. It's really valuable to get that stuff out on the table.

Jackson: (1:56:03) We talked about it briefly with the founder market fit. You have a packet that you've sent me, and presumably other people, called, "When do I use my best stuff?" Can you talk about why that specific example, but also the concepts behind it, are so important? There are a bunch of themes in this wheelhouse of authenticity, self-knowledge, alignment, and leaning into your genius. What is inside of that, and why is it so important?

Jared: (1:56:35) At the simplest level, if all of us are doing whatever the best version of ourselves is, things are going to be pretty great. I often think about Michael Jordan. He was put on this earth to play basketball. It was fine that he played baseball for eighteen months, but we're all really fortunate that he played basketball for as long as he did. What's your basketball? What's your zone of genius? The "best stuff" exercise looks at your teenager to adult years and asks when you were at your best. You list the categories, which is interesting, but what's more important is asking what about those things brought out your best self. I actually think the sub-bullets are the most interesting part. They usually rhyme with each other a lot more than the top level. You're given this instruction booklet of what aspects of an experience usually bring out the best version of yourself. It can be wide-ranging. It can be the kind of people you're with, the aspect of the project, or the function you were asked to do. What I try to push people with, and what I've pushed myself on, is not that every decision and experience you sign up for has to perfectly match your best stuff. Just think about how far you are deviating from this amazing past that dictates your best.

Jackson: (1:58:06) The correlation line.

Jared: (1:58:08) Just be careful if you're veering too far off on it.

Jackson: (1:58:13) What I like about it is that some of the examples are from when you were a little kid or in high school, and they seem quite trivial. We often get far away from ourselves and forget those moments. The other interesting part is what it feels like inside the questions. It asks, "When do I actually like myself? When am I really proud to have been me?"

Jared: (1:58:44) Yes.

Jackson: (1:58:46) One of the things I found, granted it was a unique time in my life when I was doing it, was that it was a little hard at first. It shouldn't be that hard, but we abstract ourselves from these things.

Jared: (1:59:01) We often want to examine and diagnose others instead of ourselves, especially the people we think are causing us friction. That's worth doing to understand why a setup isn't working, but it ultimately comes down to self-examination and self-growth. One of Josh's great lines that I love is, "If I'm not embarrassed about the person I was two years ago, I'm not growing." What an amazing approach to acknowledge that you were trying your best and have worked to get better. You have to be okay with knowing you've made mistakes in the past and need to grow from them.

Jackson: (1:59:44) There's also an element of reluctance to self-knowing. That reluctance is so strong that a lot of people will spend their lives chasing what somebody else thinks is good.

Jared: (1:59:55) When it comes to self-knowing, you actually have to do something with it. When you put it on someone else, you can tell yourself it's for them to figure out. It removes your responsibility because you've already told them.

Jackson: (2:00:04) There's a trio of things that tend to bubble together in very successful people: ego, ambition, and impact. Obviously they aren't totally at odds, but they can be in tension with each other. My sense is you've spent a lot of your life being a mirror, supporter, and advisor to people with incredible ambition. You're helping amplify them in some ways, and you're helping them balance those things in other ways. What goes into helping those people see clearly and keep those things in balance?

Jared: (2:00:49) That's a 6-degree black belt human psychology question. I think it's easy to try to dismiss or fight ego, but that's pretty dangerous. Having a healthy understanding and awareness of your ego is important. You have to look at it and say, "This is the way you've served me well." It's just a thing, and it's a fuel. It's probably more of a dirty fuel than a clean fuel.

Jackson: (2:01:23) Probably a critical one for almost anyone who does that.

Jared: (2:01:25) It's maybe the fuel to get you off the launch pad, but not to continue the total direct journey. Ambition is a combination of all of it. What kind of ambition is it? Is it to build the biggest company? Is it to make the most money? Impact is this other thing. I think impact is self-defined. It comes in when people realize the ego fuel has served its purpose. They have a more secure orientation where they feel, "I'm here. I don't need someone else saying I'm great again. I don't need more money. I want to do something good." The other side of the coin is this legacy orientation, which may come back to ego.

Jackson: (2:02:40) This is what I mean. These things are always revolving. It's like a three-body problem.

Jared: (2:02:45) It can be a little dizzying to try to tease it all out and separate it. You ultimately get back to asking what is true for you and what life you want to live. Going back to my vision point: don't live someone else's life. You start to realize popularity or recognition doesn't really serve you. Ultimately, what do you want to do with this limited amount of time you have here? Who do you want to surround yourself with? What brings out the best version of you? If you simplify it to how you want to live the best days possible, that's a really fortunate question to ask. Not everyone gets to ask themselves that question, so just being in a place to think about it is a luxury.

Jackson: (2:03:49) One component of this is the extent to which we use legibility to feed those things. Legibility can feed ego, ambition, and impact. I want to talk about the work you're doing now in Birmingham and looking ahead. You're someone who historically tends to lie low and be in the shadows. There's not a lot of Jared Weinstein on the Internet, so I'm grateful you're doing this with me today. How do you view legibility? I don't just mean that in the super public media sense, but even just talking about what you're doing. Some people put their head down and do the thing, while others think all press is good press. How have you evolved your view on that?

Jared: (2:04:47) Oftentimes, if you want to do big, important stuff, other people need to be on the bus with you. If you want to go fast, go alone. If you want to go far, go together. If you want to bring other people on the bus, you need legibility at some level. That can be in a one-to-one sense, a mission statement of a company, or an orientation of what you're working on. Ultimately you have outside stakeholders, partners, collaborators, funders, and the general public. I hear you on there not being a lot about me in the public domain. But for my twenties, I was at the White House, which is a very legible place. I could say, "I'm Jared Weinstein calling from the White House. I need the following."

Jackson: (2:05:43) You don't need to explain yourself.

Jared: (2:05:44) You don't need to explain it. At Thrive, 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. The people who needed to know about me knew about me, and that was fine. If you stick your head in the sand and don't share your work, you may not be as effective. There may be people out there who want to collaborate or come along. I don't think it's an ego thing for me, though I'm aware it could be. It's ultimately an effectiveness thing. I want the work to speak for itself, but sometimes people need to know about the work.

(2:06:41) Leaving Thrive, Coming Home to Birmingham, and Overton

Jackson: (2:06:41) You left Thrive in 2022. Did that feel like a risk?

Jared: (2:06:46) Yes, it was. Someone told me that people look at others and think they do courageous things, but then you talk to the person and they say they just had to do it. It was just the time to do the thing. I love Thrive and I am so proud of it. I'm proud of the people across all aspects of the firm. I'm an all-in kind of guy. My mom got terminally sick in 2000, and I was down with her a lot. It became a little harder to be all in, but I think I still was. It also totally changes your perspective on a lot of things. There has been no bigger champion of Jared Weinstein in this world than Brenda Weinstein, and she needed a champion. I was really glad I was in a place to be a champion for her. She's in a different kind of place now. She's not the same bubbly person she used to be, but she's still with us, and it's given me this amazing time. It meant stepping back from something I cared a ton about and was really proud of. I had so much confidence that we had built something that worked. We had amazing people doing great things, so it was easier to hand it off. I had tons of confidence. People wondered who was going to do what, and I just told them, "Guys, you're good. You got this." I stayed on some boards. I still take phone calls, help with things, and invest in the firm. It just felt like the right thing to do. Once I made the decision and we talked about it, it felt right. There was a little bit of the unknown. We talked about whether I should stay on in more of a venture partner role, but I thought the right thing was to step back. I will always be a champion and helper in whatever way I can. Josh has remained a close friend, and all the people there are close friends. When you're operating at that level and involved in everything we were building, it feels a little like you're stepping off the platform. You wonder what your identity will be. But I really trusted that the right thing to do was to step back, focus first on my mom, and see where I would be drawn to spend my time. I'm really happy with it.

Jackson: (2:09:58) You've had two very critical, long, identity-consuming professional experiences. I helped start a startup and was there for four years, and leaving felt like my entire life. How long were you at Thrive? Twelve years?

Jared: (2:10:18) Eleven plus years.

Jackson: (2:10:21) That's a whole thing. As a prelude to returning to Birmingham, you spent time in three very distinct places that I referred to earlier: D.C., Silicon Valley, and New York. You seem to be a remarkably consistent person. I'm curious what you've maintained and to what extent you've remained consistent moving across these very different worlds. What do you think is consistently relevant or valuable as you've worn those different hats?

Jared: (2:11:02) At least in the time I was in all of those different places, they were wildly different. I feel like the same person I've always been, and I sure hope I've grown, changed, and been positively impacted by all those experiences. I've been a hard worker since I was a kid. I have been a curious, friendly, and compassionate person since I was a kid. I've been an ambitious person since I was a kid. I've wanted big things and exciting things, and in some ways novelty and difference, trying new things. D.C. had very much a zero-margin for error. You get the speech to the podium, and the words have to be right. You were making changes to ensure this many people got this kind of government aid, that the exact right thing was being said, his tie was perfect, and the schedule almost...

Jackson: (2:12:06) How high can we get the floor?

Jared: (2:12:08) Not entirely, and mistakes are always made, but it's really about flawless execution and ensuring that machine works. Silicon Valley was a different pair of pants. This was real risk-taking. You go out to figure it out, and you just have to put one foot in front of the other and keep going. What starts as an idea, a pitch deck, and some capital can become a massive enterprise. In government, these are institutions that have been around for a really long time. New York was incredible. I love New York, and I'm there a lot. Just the boldness and the ambition, the things that are possible, the speed, and the creativity. I'm really glad I lived in D.C. first. It would have been hard to be in D.C. after living in New York. Birmingham is the fourth place and is very different now that I'm here a lot more.

Jackson: (2:13:17) What is special about this place, Birmingham?

Jared: (2:13:20) My family experienced the American dream here. We came over from Europe, down from New York, and started a peddler business that grew into an aluminum metal manufacturer. It provided a ton for my family. It was also a place that formed me, and I'm really grateful for what I got to see. It's a place where family is really important. It's a really interesting city because Birmingham came out of nowhere after the Civil War. It was an industrial thing that came out of the railroads that crossed here, and that's why everyone congregated here. It was on a tear from the 1870s until the 1950s. Birmingham was the bet as the next city, or the city of the South. There's this fascinating history where they actually wanted to put what is now the Atlanta airport in Birmingham in the 1950s, and we pushed in a different direction. Unfortunately, in the 1960s, it was a pretty ugly time in Birmingham, and the country was watching that. That has been an identity struggle for Birmingham in many ways since then. It's important to understand why people acknowledge and think about that past, yet you have to acknowledge it and move forward. I'm very interested in cities. Cities are super fascinating to me. Maybe not for us who move around globally, but for a huge amount of the population, cities are their atomic unit of opportunity. It's where they have to work, and their family, school, and experiences are there. Companies are complex, but cities are massively more complex. There's a thread since I was younger. Going to Duke was unexpectedly interesting. Raleigh-Durham was a place that was not overly dissimilar from Alabama. It was a rural place that, with the Research Triangle and these universities, figured out some things to do. I think a lot about how cities like Birmingham can change. Sometimes people say that sounds really hard, and wonder if you can really do it. Then I think about Detroit. If you had read an article 15 or 20 years ago that said Amazon was putting an engineering center there, and all this cultural activity was happening, that would read like an Onion article. Now it's reality. In 15 or 20 years, places are changeable. I think a lot about what tools I can use, from the nonprofit space to investing in companies and real estate. I look for cultural and 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, stay true to its identity, but also move forward toward making it the best place possible.

Jackson: (2:16:44) Before we talk about what can be done looking ahead, as I understand it, you started getting involved here much earlier than when you moved back. Almost around 2013, pretty early into Thrive. Maybe there's an element of civic duty going back to the White House days. What went into it? Was it obligation? Was it duty?

Jared: (2:17:12) Was it love?

Jackson: (2:17:12) Was it gratefulness? What caused you to start doing that? And how did you manage it? You weren't exactly not busy.

Jared: (2:17:23) I was a few years into Thrive, which was exciting, and Palantir was still going on. I might have been subconsciously worried that I was just becoming a finance guy. I wasn't in government service anymore. Thinking back to my granddad as a business leader who was civic and community-focused, I realized a part of my identity was thirsting for that. New York is amazing, as we both know, but I felt my efforts were a drop in the bucket there, and my heart wasn't in it. I was looking at Birmingham, and the reality was that growth had been slower here. There were things happening, but it felt like I could take my experiences from D.C., Silicon Valley, and New York, take the things that were working in those markets, and geographically arbitrage them by bringing them here. That started with an education program in 2013. We called up this education program in San Francisco and asked them to come to Birmingham. They basically said they weren't coming to Birmingham, Alabama. I asked what they needed to see and what the goalposts would be to consider it. For a number of years while I was in New York, I was playing matchmaker. I was legible to these national places. They saw I was in New York in venture capital, so maybe I understood them and could help them think about Birmingham. To people in Birmingham, I was identifying innovative programs. They saw I was exposed to a wide spectrum of things, and they supported me in bringing them here.

Jackson: (2:19:17) As you said earlier, companies are complicated. Cities are much more so. There are companies that are effectively run like dictatorships, and in fact, we often glorify them. You can't run a city or significantly affect a city in a super top-down way when it comes to a theory of change for affecting a place that you care a ton about. One thing we were talking about the other day was how the timescale is very different than other problems. I mentioned something about nonprofits, and you made a comment that nonprofit is conflated with impact and you're tool agnostic. Across these types of things, I'd love for you to talk a little bit about whether it be the infrastructure side, the civic side, the government side, the business side, or the cultural and storytelling side. What have you learned? You've been working on the problem for a long time, but what have you learned as you try to sink your teeth into it in terms of what can happen, how long it takes things to happen, and how these things fit together? I realize that's a really open-ended question.

Jared: (2:20:34) I love it. Top-down needs to meet bottoms-up. Singapore is an amazing top-down example in many ways, and there are probably some Middle East cities that have more top-down approaches. My work on Birmingham 1.0 for the first ten years was, in short, going to find these national models in education, early childhood, workforce development, and entrepreneurial support in coding. I realized these work, they have the most efficacy, and they're very compelling strategies. I decided to bring the best strategy here and execute on it, and I think that did have impact. The programs were good, and our outcomes were good. An unexpected downstream effect was that it served as an example to others that you can bring things here. It was social entrepreneurship in many ways, and that remains a compelling part of the theory of change.

Jackson: (2:21:41) To be clear, those things don't need to be tailored to Birmingham.

Jared: (2:21:46) I think they need to be local. Anything needs to be localized, because you can't cookie-cutter everything. There are gradients, but you have to meet the community where it is and then push the community. That's what these programs did. They were largely national models where I was incubating the Birmingham version. I continue to do that and I'm always interested in ways to do more of it. As I started to spend more time down here, I was doing startup investing. There were startup founders and real estate projects where I thought it would be neat to have downtown be more dynamic. I would see things in other markets and think about how they existed in Brooklyn, so it would be fun to have a Birmingham version. People would like that, because humans are humans and we all largely like the same kind of things. As I spent more time down here, I realized I could keep finding the strategies myself and bringing them here, but maybe I wanted to approach it differently. Instead of taking national strategies and bringing them to Birmingham, I decided to take people in Birmingham who are exhibiting versions of a founder-mode orientation and unleash them. That's been a new leg of the stool of my work. I don't care what you're working on here, I just care that you're going for it. There are great institutions here and companies that make sense for some people to work for, but I want to balance that with people who are saying they want to start a new tech company, a wind power company, a food pantry, a restaurant, or a youth sports league. I don't really care. It's a bottoms-up approach to unlock their potential and support that thrust. It's about letting a thousand flowers bloom and creating the conditions for people who show a risk mindset or agency relative to the community. We unleash that agency and support them on the journey as a venture investor would. We invest in a lot of sectors. This is impact venture, and some of them are companies. I invest in a ton of tech companies down here, but I've also invested in restaurant groups, real estate developments, and nonprofit initiatives. That's what I mean when I say I'm tool agnostic.

Jackson: (2:24:29) When you say conditions, how important is money? What else matters? If you had $100 billion to deploy, what would be solved and what would not be solved?

Jared: (2:24:46) You're going to be my $100 billion investor.

Jackson: (2:24:50) My sense is Dan Gilbert being worth almost $100 billion has been really helpful for Detroit, but that's clearly not the only thing.

Jared: (2:25:00) It's helpful because of the time horizon by which he can make his investments. External capital may not work on that time horizon.

Jared: (2:25:11) I think that is important. You can think in decades. You can buy the buildings he did that didn't have a market return at the time, and then create the conditions where that real estate will be valuable. Financial resources are helpful because they can align people and drive things forward. There's a debate in markets like Birmingham that there's an access to capital problem and we don't have venture capital the way other markets do. I think that's directionally true. Yet I know from our time at Thrive that I can wire money to a founder in any market in the world in 30 seconds. We are incentivized to go find those opportunities. While founders may not bump into you on Lafayette Street the way they do in New York, we do go and hunt those things, and venture investors are out there looking for them. I sometimes push back in Birmingham on the idea that it's just an access to capital problem. We have founders here who have built billion-dollar businesses and found capital outside of Birmingham. Ultimately, we need to keep developing our founders to not just be excellent for Birmingham, but to be excellent in the global marketplace of whatever they're building. That's where some of my more recent work is focused. I tell them not to just look around town at their competition. We need to normalize what people are doing to go for it. What does it mean to really have that growth mindset? What does it mean to compete on a global level with founders everywhere? It's scary, but I like supporting people and I don't really care what they're working on. Hopefully, to your earlier point, I listen and also give the tough advice when they need to hear it.

Jackson: (2:27:09) Another component of expanding beyond a local maximum is being able to see the other peak. It seems that especially for young people, the most ambitious thing you can conceive of is the most ambitious thing you've seen.

Jared: (2:27:33) It starts with being comfortable taking risk. I'm trying to lay the groundwork for people to feel more comfortable taking risk. We have been in a time where the tech startup is the sexy thing, and that is important, but every market can't be Silicon Valley. Company and entity creation in general makes for a more dynamic place. 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 a pretty good food scene, and we have people who are inspired not just by the people here, but the Keith McNallys and others. We need to think bigger.

Jackson: (2:28:29) There's an element of this that is culturally reflexive. The best thing you've seen compounds in both directions.

Jared: (2:28:40) In many ways, the internet is making the world flatter and people see all these things, but that is only half the battle. It still feels far away. Brian feels exactly right. That is why local examples that work are so compounding. I want to create as many great outcomes as possible and highlight that work.

Jackson: (2:29:11) It makes the proximity feel closer.

Jared: (2:29:12) It makes the proximity feel real. You realize, "I saw that guy at the coffee shop. I can do that." It's not just this fairytale thing far away.

Jackson: (2:29:19) This is why representation is not a woke thing. Being able to see a person who looks like you or is from the same place as you has a psychological element where you realize, "Wait, I could do that."

Jared: (2:29:33) Absolutely.

Jackson: (2:29:33) 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. I know one of the main projects goes farther back to the Birmingham Talks days. Can you talk a little bit about Small Magic and why that is a version of this reflexivity around kids experiencing language?

Jared: (2:29:57) We started working in Birmingham in 2013. I was begging these national organizations to think about Birmingham. It was tiring, but we would get them here. One day in New York, I got an email saying, "We're Bloomberg Philanthropies. Are you the Birmingham guy?" I thought, "Have I made it?" They said they found a program out of Providence, Rhode Island that focuses on early childhood brain and word development, and they were looking to take it to other cities. They heard we had done a version of taking models to Birmingham. It was neat because I had been begging people for so long to think about Birmingham. We were finally making progress. The general concept is lower-income kids hear 30 million less words by the age of five than higher-income kids. That is so important for brain development.

Jackson: (2:30:54) You mean 30 million less words?

Jared: (2:30:56) Parents and caregivers talk to them less. They're just not involved.

Jackson: (2:30:59) They've heard 30 million less words.

Jared: (2:31:01) Correct. It's about that specific interaction. It's not just TV words, but conversational turns and engagement with an adult. Just little reps. The program had some early progress in Providence, and Bloomberg wanted to bring it here. We partnered with them and the mayor's office in Birmingham. It was an incubation in the same way we would do at Thrive. Conceptually, it was an interesting idea, but we needed to find a way to make it work for Birmingham. We found the right founder, a woman here named Ruth Anne Moss. I played venture investor, board chairman, and 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 five. It's a huge aspiration that goes beyond just this talks program. We have to think about how we are providing childcare and early childhood education tools broadly, including health-related things. It's big and it's bold. We have a responsibility to put kids on the highest trajectory we can. Schools in the K through 12 system are hard to influence. Early childhood is almost like an arbitrage. It's a better sandbox to be entrepreneurial in versus trying to change the schools. It's one of the initiatives here that I spend the most time on, and I'm really proud of it.

(2:32:40) Busier Than Ever: Mentors, Life in Acts, and What You Hope to Be Known For

Jackson: (2:32:40) You said to me recently you're busier than you've ever been. How's that?

Jared: (2:32:44) I've never had a problem with having a lot on my plate.

Jackson: (2:32:48) I should clarify. I mean that twofold. How is it, and how is that possible? That's not intuitive for a person looking in from the outside. They think Jared left Thrive, came back to Birmingham, and is just hanging out.

Jared: (2:33:04) For a year or so, I just slowed down to see what that feels like. Then I set an incredibly high bar. If something interests me, it deserves to be on the calendar, and it better interest me a lot. I'm interested in a lot of things, and that certainly goes beyond Birmingham. I remain super interested in investing in general. Investment firms are fascinating, and I love supporting Thrive however I can. There are also emerging people building funds who are interested in my help, which is exciting. I have a lot of big things across the spectrum, from Birmingham to other investments and investment firms. I'm trying to stay at the most strategic level of those things. In other jobs, there's a lot of busy work. Now, I'm really trying to stay focused on high-ROI work. I have as much of that on my plate as I've ever had.

Jackson: (2:34:17) You have the discretion and ability to not get into the busy work. However, people seem to say that you're very willing to roll up your sleeves. What is the threshold on that? Maybe it's just about the top-level choices.

Jared: (2:34:41) You had to do that. When I took on the responsibility at the White House, and even at Thrive, it was—

Jackson: (2:34:48) But I don't necessarily even mean in those contexts.

Jared: (2:34:53) I learned that it was important. As I said, Andy Card was strategic. You have to do stuff to prepare for it. Who wants to be a big shot that won't roll up their sleeves? It's such a high-status move, and that's just not my energy.

Jackson: (2:35:18) How do you think about the costs and benefits of concentration? Presumably, you are more distributed and have more seeds growing now.

Jared: (2:35:33) I had two experiences in the White House and at Thrive where I was deeply concentrated. I really loved those. It's funny, you were at the White House, but you had a thousand things going on. At Thrive, you have a portfolio of companies and projects.

Jackson: (2:35:48) So concentrated frames within those.

Jared: (2:35:51) Now I feel there are a number of projects, initiatives, investments, and people that I'm trying to help. But I'm also deeply concentrated and disciplined on life. I'm almost being selfish in a way of asking what I am most interested in. If I'm interested in it, I'm going to be unapologetic and go explore it. However long it serves me, and I remain excited and think I can help, great. I get that from an external view that can look spread thin. I frankly get de-energized by being spread too thin. That's why I've started to build a team that can lever me up more and help me be sufficiently effective at this broad range of things I've got going on. I do imagine that I will continue to concentrate and narrow. Whether that ends up being a firm one day or a role leading something, I'm not totally sure, and I'm okay with that. Earlier in my career, I would have been very nervous about what the right thing to do is, or what the world expects.

Jackson: (2:37:06) Or that you've been out of the game, quote-unquote, for too long.

Jared: (2:37:08) I don't feel that way.

Jackson: (2:37:09) One good way to find a really concentrated thing is to plant a lot of seeds.

Jared: (2:37:15) Absolutely. I got some advice from an amazing mentor named Tom Tierney, who was an early leader of Bain Capital and Bain Consulting. I had actually brought him down to sit with the President about what a post-presidency life could look like. He had helped leaders think about that. I remember him saying, "Jared, I've always found repotting myself has been an incredibly valuable way to live my life." I potted myself in D.C., and we're repotting some things going on now. That will change too.

Jackson: (2:37:50) We didn't talk about it when we were speaking earlier. When did you first come across the idea of when to use your best stuff?

Jared: (2:38:00) I was fortunate to be introduced to a coach. I had never known much about the executive coaching world. Someone said Tiger Woods still has a coach and he's at the top of his game, so leaders should have coaches. I met someone, she gave me the exercise, and I've since sent it around a lot.

Jackson: (2:38:26) It's probably helpful in approaching the combination of self-knowledge and your happiness quotient.

Jared: (2:38:33) Absolutely.

Jackson: (2:38:35) Do you think about your life in acts? At the very least, you could retroactively look back and see some pretty clear chunks. I'm curious if that's still resonant. Do you feel like you're in a third one of those? Is it a pause, or is that not the right way to think about it?

Jared: (2:38:53) My experiences have been quite different from each other, which sets things up that way. I think about it because they were very different for me too: D.C. and Thrive, and now being a little more focused on things outside of work. I don't know that this act will be ten years, just like the previous two were. I don't know if it will have a story that the outside world finds as interesting. I'm sure someone is wondering what the next thing is after Thrive and the White House. That's a lot of external pressure to put on my story. I'm exploring and going after things that are interesting to me.

Jackson: (2:39:46) It doesn't seem like you got to the other two things deliberately.

Jared: (2:39:53) It wasn't for the purpose of the story. There's a lot of pressure to do that, but that's doing it for someone else.

Jackson: (2:40:07) We've talked about a handful of people and mentors who have been influential on you. Two we didn't speak about explicitly in the context of Thrive are John Winkelried and Nitin Nohria. I'm curious to the extent those guys were influential on you personally or on Thrive, and what you learned from them.

Jared: (2:40:28) I want to give them both appropriate time. John Winkelried is such a special person. He was special for Thrive in our early days when we tried to learn from others who had done things. John was there in the weeds with us, and he now leads TPG. He is such a motivating individual to be around. He was in the trenches of Goldman Sachs for his career and helped scale that organization. The fact that he was willing to sit with us when we were not a big, well-known firm was amazing. He's a great listener. He helped both the firm and Josh and me individually think about our own leadership styles. He could pick up the phone, call me, and say he was thinking about going to buy some dollar stores, and I'd be all in. John is really special. Everyone, whether at Goldman, Thrive, or TPG, has loved working with him. At that time in Thrive, I had lived in a very strong mentor environment in the White House. There were so many different individuals we've talked about who were a few years older, including the President. Then we got to Thrive and had to figure things out. Having John as a guide through all of that was really special. He never put his finger too strongly on what we were doing. He was more someone to talk to, listen to, and work through things with. Nitin came into Thrive because Josh and Nabil had known him when they were at Harvard Business School and stayed in touch with him. Nitin is a Yoda-like figure. There's just so much wisdom in him. He sees things very clearly and is a straight talker. He is very strategic and sees all the dimensions of organizations. Not only was he the dean of Harvard Business School, but he's been on the boards of massive companies, and leaders go to him. I had a few years with Nitin, and he's still around the organization today. Fortunately, he stayed in my life and has spent time with Birmingham entrepreneurs, which I'm so grateful for. His wisdom-to-words ratio is so high, and he's also a great human being.

Jackson: (2:43:30) It's telling that you guys found a way to have people like that around over the course of building the firm. This might be too personal, in which case it's fine, but what causes you to reach out to the president for advice?

Jared: (2:43:53) I remember when I was working for him, his friends or people who had left would call him, and he'd make time for them. But then they'd call a few weeks later, and he'd say, "I just talked to that person." So I try to be mindful of my time with him. I know he cares about me and has my best interest at heart. There have been times with big life decisions and work stuff where he was willing to listen and speak. He's an instinctual person. He would say, "This is what I think," and it was perfect advice. He called me earlier this year about my mom, and I didn't make it very long without getting a little sniffly. He wants the best for me, and that means a ton. The relationship has evolved from me working for him to being someone he cares about and is friendly with. I would do anything for him. Other than my parents and grandparents, no person has had a more positive impact on me.

Jackson: (2:45:12) Not to be compared, and not someone you know well to my knowledge, but what do you admire about Nick Saban?

Jared: (2:45:19) I'm really grateful that he brought us as many national championships as he did. I admire his commitment to excellence and to competing not with others, but with himself. He's motivated to just be better. Even when he was on top of his game, he wanted to be better. A number of years ago, I was sitting with Nithin at Thrive, and I said we should get a Saban case study. I called some people down in Birmingham, and he called the sports HBS case study person. We ended up putting this case study together that I went and saw delivered. The process orientation there is incredibly successful. It worked for him, and he refined it. Look at all the coaches who have gone on to do great things. He set an example. I'm sure it wasn't always an easy environment to work in. However, I imagine those coaches are incredibly grateful they got to see what excellence looks like, and they are clearly benefiting from that now.

Jackson: (2:46:31) The tree is bananas. What are you drawn to in sports broadly? Sports on one hand are totally trivial, and on the other hand, they are one of the more human things we have.

Jared: (2:46:51) I've thought about that. I wrote my college essay on the Alabama-Auburn game as a kid. It's amazing how much attention it takes up in the state, but it's an interesting way to bring the community together. For one, I enjoy it, and that's maybe enough. Historically, sports organizations haven't always been the best-run organizations relative to other industries in the economy. Now you're seeing a lot more investment with so many dollars involved. I'm curious in what ways excellent leadership and organization can impact sports organizations.

Jackson: (2:47:47) What do you most hope to be known for?

Jared: (2:47:51) I hope I'm known as a great friend and someone who brought out the best in other people. I want to be someone who encouraged people to bring out their best selves, and someone who was good energy to be around. Any other accolades separate from that just feel like details.

Jackson: (2:48:22) My last question: what have you learned from and what do you most admire in your mom?

Jared: (2:48:34) I've learned what unconditional love is. I've learned what it means to fully champion a person in the way she championed me. I've learned to dream big. I admire how much she loved me and my sister, and how she showed up to just want the best for us.

Jackson: (2:49:05) Those last two, I think, go together. Thank you, Jared. This was great.

Jared: (2:49:08) Thanks, Jackson. I appreciate it.

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