20VC: What are the World's Tech Leaders Running From? Fear? Insecurity? Poverty? What Drives the Best with Orlando Bravo, Bill Ackman, Dara Khosrowshahi, Parker Conrad, Tobi Luttke, Brian Armstrong and more..

0:00You are listening to 20VC with me Harry Stebbings. Now one of the favorite questions that people love in our shows is if we're all a function of our past, what are you running from? This is the single most popular question that we ask in the shows. And today I wanted to bring together the thoughts of some of the biggest and best names that we've had on the show from Orlando Bravo to Bill Ackman to Brian at Coinbase and many more. So today you're going to hear from them on what they're running from and you'll see some incredible commonalities. This was such a special show to do. Let me know what you think.

0:33You can let me know on Twitter at Harry's Debnings. And likewise, I would love to see you on YouTube. You can find us by searching for 20BC. But before we dive into the show's day, you've heard me talk about how Coda is the doc that brings it all together and how it can help your team run smoother and be more efficient. I know this because Coda helps me. We have many researchers in the team who bring all the content together for the show and they need a single place to work, collaborate and collect notes, data and information in any format. This is the efficiency revolution and it is time to join in.

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3:29Now we're going to kick off the show's day with Orlando Bravo co -founder at Toma Bravo on what is he running from. Moby's on the go. I never like to stay in the same place for a tourno. Sometimes my family looks at that and says, what is he can't stay still? And I really think I'm running from the fear of being trapped, the fear of being isolated. I think about that, and part of it is I grew up in an island, I grew up in Puerto Rico, relatively small island, and to pursue things and to get better opportunities, you always have to leave. Not necessarily for everyone, but that was for me. And maybe that's why also private equity, which is a deal business, Where you go from one deal to another, from one country to another, from one state to another, maybe that's why it fits me really well.

4:14But I have this fear of stagnating and feeling trapped and isolated. Can I ask you, just feeling stagnating, isolated? Was there ever a time when you felt like your crew was plateauing? Was there ever a thing that you did to get out of that? I think often, especially state, people feel like, am I actually going anywhere? Am I going where I want to go? Have you ever felt like it was maybe plateauing? And what did you do to get out of that plateau? I felt that my career was a failure in 1999. I had come out of Stanford Business School in law school with what I thought was this like blue chip pristine Education and resume and I had very high expectations of myself and a timeline for which I needed to Quote on code succeed none of that worked.

5:00I was really close in 99 to being fired as I said before. So it wasn't plateaued. It was like, I'm going to have to start over. And I'm a big tennis fan and I used to play tennis. Maybe it helped me fight to stay in the game. Just stay in that match. Maybe take your time in the changeover. Maybe take your time hitting your second serve. And in that process also see if there's enough opportunity to change the game. And then I think it happened and I got lucky now since then I have not felt a plateau on my career because Here's the thing my job has changed enough over the years and the industry that we target has changed enough as well So if I was doing the same deal that I worked on in the year 2000 I probably would be pretty bored feel isolated and plateaued but things have changed enough We're now going to move to Brian co -founder and CEO coinbase We're all a function of our histories and a product of our histories.

5:56What are you running from and what are you running towards, Brian, if we really just start at the deep end? I'm glad you're starting off right with the therapy session here. There is a lot of psychology and therapy involved in starting a company, so it's a really good question. I think a lot of people start off in their career running from something and I'll tell you what it was in my case. I was always a shy and introverted kid. I felt like I have such good ideas, but I'm not confident, I'm not articulate, and I couldn't get people to hear my ideas. and that I think I had this deep fear about never doing something important in my life.

6:25And I don't even know exactly where that came from, but I was like, I'm gonna fucking go do something great here or die trying. I had this real desire to... Maybe it was like a status thing or an impulsence of importance. I didn't feel important or worthwhile, like on my own, which is like a deep psychological thing. As people oftentimes in an entrepreneur's life, you grow, you see a little bit of success, and then what happens is the thing that was motivating you, which was probably like fear or anger or shame. Initially, it starts to go away a little bit. Maybe it's not 100%. And so you start to lose your motivation.

6:57And I've seen a lot of entrepreneurs go through this existential moment of crisis after they start to lose the initial thing that was driving them, like fear or anger. And then they have to move towards something that brings them actual joy or love or just that they're actually passionate about. I had my own moment of that somewhere along the last 10 years where I started to think, all right, what do I actually like doing? Now that Coinbase has been billion dollar evaluation or whatever goal I had in my mind. And I was like, okay, I love building things with technology. That's probably my favorite thing to do.

7:22And then the other thing I love doing is learning new things. I'm always like, curious, I'm trying to absorb new knowledge. Being a company CEO is always pushing you outside your comfort zone into new areas. It makes me feel good to try to do things at scale that have an impact on the big meta problems of the world. If I see, oh, we went from a million people using this to 10 million or something, it just gives me a high. I don't know why. It gets me excited about, oh my gosh, like we can have even more impact. Some people they don't have that. They're very content having an impact with a classroom of 30 kids or maybe just helping one person that they're mentoring or whatever And they find that incredibly fulfilling for me I don't get the same feeling unless I'm trying to do something at scale that has like a major impact on the world So that's a little bit about my journey.

8:00The trouble is you never get off the treadmill Yeah, I mean, that is you get to 10 million users I don't know you but then I said I know you Brian. I'm probably the same What about next quarter and you never actually sit with the happiness do you ever get off the treadmill and you worry about that? I have definitely thought about that because I'm not somebody who's really good at celebrating. Usually by the time I accomplish some goal that I've set, maybe I've worked on it for years, by the time you're at like 60%, 70%, you're like, oh my gosh, I can see where this is going. It's gonna get there in the next six months or a year, just if even if I did nothing, but a lot of the hard work is up front.

8:34It's not like I have some moment of, oh my gosh, it feels so good and I hit the goal. Like honestly, I don't really feel that, but I do feel like a deep sense of fulfillment, I would say, just about if I look at where I was 10 years ago, or where I'm now or a year ago and I was like, okay, I feel like I'm making progress. I'm doing something good in the world. Obviously, I take time to do other things in life besides work. But I think if I wasn't working on something hard and really difficult, I wouldn't feel as fulfilled. I've tried going on vacation. After two or three or four days, I'm just like, I need to go read something, I need to learn something, I need to build something.

9:03It's almost like an addiction. I've had this thought before. I have no evidence to back this up, but people have all kinds of addictions. I happen to be addicted to building things and scaling them. and sometimes I'll overdo it and I'm like, oh my god, I haven't taken a day off and however long or whatever, I'm almost overdoing it. Then the other part of me is, whatever, never stop. If I find it fulfilling, I'd rather just keep building things and do that for the next 50 years or more. Hopefully, if we get longevity stuff working, if you can make your career fun, you'll never work a day in your life.

9:33Oftentimes when it does work, it's getting to a place where I'm traveling to something ostensibly for work, but I'm having fun at the same time. I'm meeting with friends, people I haven't seen in a long time. I'll go on a hike, I'll go to dinner with interesting people Jeff Bezos had this term one time where he talked about it's not work -life balance It's work -life harmony and I personally feel that if I go somewhere for a week with nothing to do but sit on the beach I find it to be like not that fun. I mean main brine have that one in common I'm not such a beach man But I do want to dive into our episode now and answer the question with Parker Conrad at Ripling.

10:04What are you running from? There was definitely a moment after I was forced out as benefits when we're a whole bunch of reasons like legally and different restrictions I was under that's prevented me from really talking about what happened and the proverbial sort of like my side of the story. And there was this period of about six to nine months when there was just this overwhelming institutional apparatus that was like a raid against me and sort of writing this narrative about what had happened. And I sort of watched that unfold from like the basement of my house with this sort of growing horror.

10:40You know, at a certain point, I kind of decided that the only way I was going to be able to talk about what was happening Tell my side of the story because you know, I wasn't in addition to just the restrictions I was under it's not my sort of forte doing that media PR jousting and I started to say the only way I was going to be able to communicate about this to people in the tech community to the world more broadly than that was to build this specific company, try and make it into like a really big, you know, $100 billion outcome. I don't know if that's something I'm running away from or running toward, but it was really sort of deeply motivating for me about just this period of time when just kind of like putting one foot in front of the other and getting out of bed in the morning was was a struggle.

11:25But for a long time, you know, that was sort of what was getting me going in the morning. Parker, I love a quote from Joshua Wolf at Luxe. He says, chips on shoulders put chips in pockets. It totally agree that you need that fuel. I remember I once lost a load of weight because a girl dumped me and I thought I'm gonna prove you wrong and it turns out she just disliked my personality, not my weight. Um, uh, uh, Percy, I will not ask any just kind of speaking of that. I did speak to Gary Towne before the show and he mentioned that tough time and my question to you was just like in that moment, what do you tell yourself?

11:55What's your mind speak? It was hard. I think that as a founder it is really hard to watch someone else making decisions about your company. It was sort of, I got to this point where I convinced that David was not really interested in making Xenifit successful. Almost every decision he made at the company was wrong. The decisions he made from a product perspective, from a strategy perspective, the people he fired, the people he promoted, almost all of it was just completely wrong. And I sort of felt like, well, I think there's a huge market here at a huge opportunity that's now I'm gonna go unfilled.

12:30Unless, you know, I was talking with Persona, I said, unless you and I kind of jump in and do this, this is never gonna happen. And there's like $100 billion like sitting on the floor over there and nobody can see it except for us. And we just have to figure out a way to sort of walk over there and like and pick it up. And like we know that if we sort of do these things, it's gonna work. And so whether it was like delusional or sort of extreme confidence in what we were doing, That was through what kept me going. Now it's time for Toby to Shopify on what he is running from. Bottom is something I like to avoid, ignorance.

13:05It's more magnetic for me. Honestly, there's more magnetism in the direction of them going, when there's reverse polarity, if you can place them coming from. I just have a strong sense that the goal in life is try to become the best version of yourself. It sounds like super fortune cookie, but as if at the end of life you meet the person you could have become, the work of life is really try to minimize the diff, between that person and the one that actually showed up. Not understanding a thing feels almost amoral to me. We've got these incredible brains. These brains run a model of platter, which we then constantly interrogate.

13:39I want that model to be right. Therefore, every single thing, every single time I get to dig into something, into learning something, I can update this model. And the nice thing is, for sure, that's super fun. Second, that model is the one I work around with. I go into every one of my meetings with, I go into every counter, every situation, I hold up to every problem that I need to solve. Advocating of all decisions is simply how correct, how close to the truth is that model of a world that I've been developing. And I want to be able to reason about the new strings that exist in the world. I need to not treat transformer models as a black box.

14:14Like I need to understand those, because I cannot show up to a meeting with my teams and have a good chance of reasoning with them about not just what is sort of the colonial next task, but what's the very best thing we could be doing? What is the new thing about all of this unlocks? And that's been driving me every step of a way. I'm loving comparing and contrasting the different answers here. Now we're going to be joined by Ariel Cohen, co -founder and CEO, Navan, formerly trip actions. You said to me, school and university, you don't really go to that many lectures or lessons. I've just intrigued like, why?

14:46The type of person that I am, I can learn stuff by myself, but I can only learn stuff that really interests me. The reality is that I think that most of the things that you learn at school and universities are just not interesting. There are things that, for example, some case studies that you're gonna go through and I could be so much fascinated by that. But then I go all in. For me, the way that I can learn, it's only if it interests me. If it's not I cannot really study it and that was my school life. I was actually an extremely average student. If I could either have like really really really good straight A, but on the really good side of it, or I would totally fail and it's really based on the way that kind of maybe my brain walks.

15:30If it gets my interest, I would geek out and learn everything about it. If it doesn't, you cannot get me even starting to get interested in this. Because does that impact how you advise your children when it comes to how they pick up and learn new things. One hundred percent. So I have three kids. Two of them, they are twins. They're boy and a girl. They are 15. So they are starting to think what would they do next and so on. One of the things that they've told them, hey, do whatever you want to. But my advice to you, don't even at age 18, have this pressure to go to college. Because I don't think that what you really want to do with your life at age 18, and I know that a lot of people are doing this keep here.

16:05And I like traveling. A lot of my conclusions are happening while I'm traveling. So my advice to them what you're gonna do with your life and school and all of these things It will get figured out but first take the time to really learn to really understand what to and I think that in any case We are in such a Interesting time in our lives with the development and I know that we're gonna talk about it But with the developments of a machine learning and AI So I'm not even sure that the things that we are learning to not absolute my advice to them don't take this too seriously So I think secretly I've always wanted to be a psychologist, but we mentioned children there and psychologists always give everything to your childhood and how it impacted you.

16:45I do think everyone is a function of their histories. What do you think you're running from Ariel? If you take a step back, I think the one that comes in mind always for me is Salesforce and SAP which are not innovating. I think the last time that SAP innovated something was in the 90s and the last time that that Salesforce innovated was in the beginning of 2000 and I'm looking at this and besides the fact that I think it's embarrassing that companies that are located in the middle of Silicon Valley have not been innovating for years. It's also what I'm running from. The one thing that scares me is that one day, Navan will be that kind of a company that they'll only weigh that you innovate through M &A and through using your own market dynamics and your power in the market to basically sell.

17:28And this really scares me. Now the final founder segment we're going to dive into his with Dar Cause Rasha, he CEOed Uba. I do think that the events of Iran and our family losing everything, and we had a huge family, big family business, etc. I don't know if it's something that we're running from, but I think the whole family, to some extent, is running to rebuild essentially what we lost in Iran. You've got an ex -generation that is incredibly passionate and ambitious if you look at my cousins and Haudi, etc. It's just an example, which is I think we just have this immigrant ship on our shoulder.

18:04They already much look up to our parents who built this incredible business in Iran. We all want to do our parts to rebuild again. And I think that's definitely shaped the ambition that my family has. I will tell you that while we lost all of our money in the business, so to speak, the thing that we never lost was family. And so for me personally, having the family around us, having that sense of love and belonging and protection is something that I treasure. Building that collective and having that shared success, for example, in business, for me is something that really draws me. Celebrating your success as an individual is not nearly as fun as celebrating as a family or a team.

18:46So for me, I think family shaped how I look at success and for me success is joint success, it's shared success. My family is lost everything too when I was young. For me, when I lost everything, I equated rebuilding with worthiness. When I rebuilt it back, I would be worthy again. The trouble is dark. I've kind of rebuilt a little bit of it back now. And I don't really feel that worthiness. How do you think about worthiness and that rebuilding and whether that's part of it? I think for us, there's always been this sense of pursuit of excellence. So I don't think with my family, it's about rebuilding a worthiness or money one way or the other.

19:23But it's about pursuit of profession. My dad told me, Hey, you can be two things. You can either be a doctor or an engineer, pick one. So there's always this drive that my parents instilled in us. But for us, being worthy is not about an end state. It's about going all in, putting in the effort, being diligent, working hard. And that's what drives me. If I feel like I put in the hard work, sometimes it's gonna work out sometimes it doesn't. But if I put in the work, then I'm worthy that day, and then the next day I gotta come back. Yeah, I know. I said it was the last one from founders, but I just found a couple more really great ones.

19:56So now we're gonna move to Taric at Kalashie on what he's running from. That's a great question actually. Never been asked that on a podcast. Personally, I think it just like tends to be very related to parents. My dad was really absent, and I think there was this kind of constant need of like, where is he and what's going on and why is he not there? And then to my mom and I actually did a lot of things to her. She was a great parent, But she was very strict when it came to excellence. It was truly one of those things where like, you come back and you're excited about having achieved 98%, she is just focused on the 2%.

20:25She was like, where is that 2 %? I think she just like would push us to be at 120 % of the way every single day. Like the 120 % was very consistent. Everything we did. I think that drive and that sort of need for 120 % that doesn't lead. We're gonna keep going with this. Fuck it. Jamie Simmon or for Ring. What are you running from and how does that impact you? I'm probably running from as a kid. I was not the coolest person in school. I had definitely my share of incidents where looking back I would have liked to bend the cooler person, but I think the inventor in me I just see problems everywhere and I want to solve them The hardest thing I had to learn was you can't solve every problem for everyone because then you do nothing like how to focus that energy was what took me a while to learn and took me till I got older to harness You mentioned not being necessarily cool as a kid.

21:13I wasn't either and I'm a people pleaser as a result. I desperately seek other people's approval and always try and please other people. Are you a people pleaser as a result? And I guess what advice would you have for me? Always looking for people's affirmation. I always say I don't have an ego but I certainly like people seeing me successful. Looking back, it's not terrible that people had to send me emails saying, wow, I can't believe where you've gotten to. Again, it's not only that's the reason you should do it but it doesn't hurt. A lot of entrepreneurship is like reality distortion. You have to believe in something that's much bigger and crazier than what can actually be accomplished.

21:47When you're a kid and you're in that position, like one thing I learned, I moved schools because I was like literally ostracized from my high school. My parents were very nice because they were middle class and I went to the private school. They paid for me to go. It was a little bit of a hardship. When I got there, I was just like, I'm gonna be the cool kid now. And I just made up this life because by the way, screw it, why not? I think that's part of entrepreneurship is you just you got to make it up because when you're in your garage building a doorbell If you really told people what you really felt and where you're at you probably would never make it and so you have to say Yeah, I'm gonna build the biggest security company ever in the history of the world You're gonna be a little crazy.

22:19So maybe that's what taught me that now for the final two We're gonna switch to the investor side of the table and we're gonna join the legendary Bill Ackman for the next segment on what he is running from I don't know that I'm running from anything. I think I'm running toward things greater happiness Self -actualization, great relationships, friendships, and one of my running work away from maybe death, disease, what do I want to minimize the risk of something bad happening? One of my want to maximize happiness and where does it come from fulfillment, relationships, self -actualization, achievements, things like this.

22:50Can I be blunt? Do you appreciate that happiness when you have it? Of course, and I'm by the way, I've been consistently happy pretty much since birth. I've had volatility in my career. I've had volatility in my marriage. I'm now married again. I've gone through challenging times I've experienced sadness and loss and all those things, but I think the undergirding Support here is happiness. I'm an optimist and I'm a happy guy now the final one Martin Eskibari a general Atlantic again on what he is running from Bolivia is a place of limited possibility because of his history because of its poverty because of his lack of infrastructure and A stereotype dreaming boy is claustrophobic in our world limited opportunities and gets a little crack in the door in our world of limitless Opportunities in the US at Harvard and as I've seen my life Transformed by the opportunities provided by the universe in the US and elsewhere I want to help other entrepreneurs and other people globally tap into that little door into a world of limitless Possibent so that's my journey When your parents saw you, the scale would go to Harvard, they must have been immensely proud.

24:00They don't know what Harvard is. They had never been to the United States. I didn't know what Harvard was. I actually wanted to go to Yale. It was ranked number one in some ranking I had seen. I was like, I can't tell Apple's from Orange. I need to go. Harvard was number two. Yale was number one. I got into Yale. I got into Harvard. And then a very famous guy from Bolivia, the governor La Paz called and said, you aren't going to Harvard, right? And I said, sir, I'm sorry, It's number two and one number one and he convinced me. I had no idea. I landed there. I was like, okay, fine Whatever. So yes, now they understand and they're very proud at the time.