649: Sam Lessin - Type 2 Fun, Voluntary Hardship, Joy as a Competitive Advantage, Long-Term Thinking, & Life Lessons From Dad (Lessin's Lessons)

17 Aug 2025 · 56 min

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In short

Podcast Summary: The Learning Leader Show with Ryan Hawk - Episode 649: Sam Lessin

Episode Overview Guest: Sam Lessin Role: Partner at Slow Ventures; former VP of Product Management at Facebook Key Themes: Type 2 Fun, Voluntary Hardship, Joy as a Competitive Advantage, Long-Term Thinking, Life Lessons from Dad

In this episode, Ryan Hawk interviews Sam Lessin, who shares invaluable insights on leadership, entrepreneurship, and the importance of joy in both personal and professional realms. Drawing from life lessons from his father and his extensive career in technology and venture capital, Lessin emphasizes the significance of hard work, resilience, and strategic thinking in achieving success.

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Key Takeaways

Life Lessons from Sam's Father

  • The 4:30 AM Advantage
  • Early work creates a compounding advantage. His father would start work by 4:30 AM, stating, "It's easy to look smart if you have a several-hour head start on everyone else."
  • Timing and Opportunity
  • "Either be early or be late, don't be on time." Assess the right moment to start a career or venture.
  • Joy as a Competitive Advantage
  • Long-term success comes from joy: "I just don't think that in the long run, angry people win."

Type Two Fun

  • Definition and Importance
  • Type 1 Fun: Activities that are enjoyable while engaging (e.g., rollercoasters).
  • Type 2 Fun: Activities that are difficult but rewarding in hindsight (e.g., climbing a mountain). Entrepreneurs need to embrace Type 2 Fun to build resilience.

Voluntary Hardship

  • Lessin practices voluntary hardship (e.g., running a sub-3-hour marathon, obtaining a pilot's license) to cultivate perseverance and prepare for business challenges.

Key Insights on Investing and Leadership

  • Right Person, Right Opportunity, Right Time
  • Success is not just about talent but the alignment of the right person with the right opportunity at the right moment.
  • The Importance of Public Writing
  • Writing publicly creates accountability and clarifies thoughts. "If you can't write the check, write me the thesis and timestamp it."
  • Embrace the Unknown
  • "Nobody knows what they're doing." Even prestigious companies often lack clear direction, which can be liberating.

Slow Ventures Philosophy

  • Patience and Long-Term Thinking
  • Most success comes from persistent efforts and the recognition that big things take time to develop.
  • Joyful Leadership
  • Lessin emphasizes the importance of hiring joyful individuals who exhibit passion for their work, as joy correlates with sustainable success.

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Useful Quotes

  • "It's easy to look smart if you have a several-hour head start on everyone else."
  • "I just don't think that in the long run, angry people win."
  • "Writing is thinking. If you can't write, you can't think."
  • "Big things take time."

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Personal Reflections

  • Lessin’s reflections on his father’s influence reveal a deep appreciation for hard work and the joy of the journey. The influence of near-death experiences on his father's outlook adds a compelling layer to the conversation about resilience and the value of living in the moment.
  • The conversation underscores that everyone is on a unique path where learning and growth come from both triumphs and failures. The themes of joy, perseverance, and the importance of timing resonate deeply with the experiences of those aspiring to lead and innovate.

Conclusion Sam Lessin's insights provide a refreshing perspective on leadership and success. His emphasis on joy, Type 2 Fun, and the importance of relationships in business serves as a powerful reminder that the journey of entrepreneurship is as significant as the outcomes. This episode is a must-listen for anyone looking to enhance their leadership skills and embrace the learning process.

For full show notes, visit [Learning Leader Show](https://www.LearningLeader.com).

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Transcript

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0:00This episode is brought to you by Insight Global. Insight Global is a staffing and professional services company that builds world-class technical teams for clients around the globe. If you need help with your applications, infrastructure, or data layer, Insight Global's team of technical experts can build custom or manage services to deliver the outcomes you desire. Getting the most out of your technology can be tough, but growing your business with the right technical solutions can be magic. Visit InsightGlobal.com slash Learning Leader. That's InsightGlobal.com slash Learning Leader. today to learn more.

0:46Welcome to the Learning Leader Show. I am your host, Ryan Hawk. Thank you so much for being here. Go to learningleader.com. For show notes of this and all podcasts, go to learningleader.com. Now on to tonight's featured leader. Sam Lesson is the co-founder and general partner at Slow Ventures. Prior to that, he was the founder and CEO of Drop.io, which was acquired by his college buddy, Mark Zuckerberg. Sam then worked for Mark as VP of Product Management at Facebook from 2010 to 2014. During our conversation, we discuss how learning to ballroom dance could help you land your dream job. Then the importance of joy and excitement for the highs and lows of your job and entrepreneurship if you're trying to start something new.

1:48And then type one fun versus type two fun and why we need to be able to have type two fun. And then Sam describes what it was like going to college with Mark Zuckerberg and eventually working with him in the early days of Facebook. So good. Ladies and gentlemen, please enjoy my conversation with Sam Lesson. You know, my dad still remains the primary influence of my life, and I know that your dad was that for you. I read this cool story about him, so maybe you can go deeper on this. So he became the youngest ever partner at Morgan Stanley. And he actually wrote in his book, which is called Lessons Lessons.

2:33It's really just about life lessons. I think everybody would get value out of reading. All the money that's made from it is also donated charity, which is really cool. But he wrote that he learned to ballroom dance when he was young. And that actually helped him earn the summer internship job at Morgan Stanley. Can you tell me more about your dad and his different way to view the world and what you learned from him growing up? Yeah, I mean, that's a broad question. The answer to my dad was, you know, as he said, a really important character in my life. You know, I think of him often. He died way too young at 56.

3:06But we spent a lot of great time together. And, you know, he had a wild career. He used to refer to himself. Have you ever seen a movie called Being There? No. It's great. You should watch it. It's with this character's named Chauncey the Gardener. And the idea is that, you know, he just, this was Forrest Gump before Forrest Gump, just kind of living his life and wandering into like the most interesting scenarios and situations. So, you know, my dad's doing ballroom dancing. And he has to understand he's a brilliant guy. He's also somewhat of a character. He went to Harvard undergrad. He kind of I think even that book says, you know, wasn't poor, but didn't grow up, you know, particularly wealthy.

3:40You know, his joke was, which I think is basically true, he couldn't get dates. And so he was looking for a way to kind of do something different to distinguish himself and ended up going and learning ballroom dance with a bunch of 70 year olds and got really excited about ballroom dance and did that. And, you know, then he went to interview for investment banking jobs. And, you know, he basically got rejected from all the investment banks, except for the most prestigious one, which was Morgan Stanley. And, you know, they liked they liked that he was a character that he had gone off and done this independent, you know, this was before, you know, kids were entrepreneurs, you know, he actually hilariously in college, believe it or not, did start he tried was trying to earn money.

4:16and he started using an early computer matching rides between Boston and New York for people who wanted to ride share. So he was doing all sorts of crazy stuff as a kid, just kind of experimenting and learning. And he found his way into Wall Street that way. Wow. What are one or two of your favorite learnings that you picked up, whether from reading his work or from him directly? I mean, it's really, really hard to compress it down. But you know what I'd say, honestly? I think there are two things that come to mind. One is the guy worked unbelievably hard. For all like the brilliance, and he was a brilliant man and a real innovator.

4:51And he came up with a lot of amazing stuff. And really, he was a pioneer on Wall Street in a lot of ways. He also literally would be at the office at his desk by like 4.30 in the morning every day. And he always used to say, it's like, it's easy to look smart if you have a several hour headstart on everyone else, right? And so I do think that like, you know, a lot of success does come down to just like being willing to do the work. And I think he did that. I just remember a lot of like joy and excitement about new ideas and information. When he was, you know, a banker, he kind of invented this idea of transaction development.

5:25This was like in the earliest days of private equity existing. And he was the youngest ever MD. And he was kind of like, you know, he was kind of doing his thing, but he had no book of business. And so he kind of started pitching these baby new firms like KKR ideas because he had to figure out how to drum up business for himself. and became the highest earning banker, whatever the numbers are, they're in the book. But the upshot is he literally just kind of finds his way because I think he actually truly loved the people and ideas. And I think that carried into his venture. He got really excited with the internet very early.

5:55And he used to joke that he was the largest angel investor on the East Coast for many years, which was, as he used to say, kind of like being the smartest utilities executive, which means nothing because the East Coast is relevant. But he was the largest. I just remember going to meetings with him and he would take me and like his joy and excitement at the journey. And I think, you know, just making sure you enjoy the journey, work hard. It's like the stuff is in rocket science, but I just remember a lot of joy. I think that's important. There are trade-offs to excellence. Being at the office at 430 means you're not home with your family having breakfast.

6:27What do you think about working extremely hard and the trade-offs that it takes in order to do some of the things you've done? It takes, It's a sacrifice. How do you feel about that? Well, I mean, it's funny you brought up his book. I've obviously read it a few times and kind of quote out of it. But his joke in the book is he did make it home for his kids and he worked, but he wasn't there for his marriage. And it led to his divorce. He has a very honest story about this stuff. So I think there's no question there are trade-offs on these things. The thing I would keep in mind is there are seasons for everything.

6:58You can't work a bajillion hours a week all the time for your whole life. You'll hate your life. and it's also just not possible. And I think there's something about season. So my dad would say, since you bring him up, and we're talking about him, either be early or be late, don't be on time, right? He started his career super early. He started working at Morgan Stanley before he actually graduated from Harvard. He literally just showed up and started working. And again, what he says in the book is that gave him a several month head start on all the other associates, which meant he knew the partners better, which means he just worked hard and showed up first and early every time, right?

7:34And that was a strategy. And then candidly, later in his life, he didn't go over the door to Ross New Bridge after rush hour. And I think there's another strategy, which is enjoy your 20s and then work really hard later. But I think it's not one of those things where it's so binary. I think there are seasons for it. And one thing I'll say as someone who invests in entrepreneurs, I think a lot about this, which is people talk about, is that a great person? And I actually don't think that's the right question. The right question is, is it the right person at the right moment? to be successful? Because no one is always there.

8:06People who get rich and lazy, or they have other things going on in their life, or there's all sorts of factors at play. And I think really the psychology of who makes a good founder and who can put in the work and who's ready to joyfully do it are really important factors to think about. Not to jump ahead too far, but you just mentioned it. So I'll go there and then we'll go back. You make strategic bets. That's part of your job. is another way of phrasing what you do, or at least one of the things you do. You got to bet on people. You got to bet on ideas or the combination of those things. What do you look for in a founder specifically?

8:40Let's talk about the person right now. What are you looking for in people? You're like, I'm pushing my chips behind them, right? I'm going to bet on them. What are some of the must-haves in those people? I'm going to use the word joy. I think you want joyful people, right? And people who are going to be joyful in what they're doing. And I just don't think that in the long run, angry people win. And I think that the reality is that there are exceptions to that. They're always, you know, one of the things you have to understand in venture capital, especially what I do, is I'm usually wrong. You're just looking for marginal pattern advantages, if that makes sense, right?

9:17And you want to bet on people who are going to be joyful in what they're doing. And again, this is why I'm so obsessed with it. It's not about great people, bad people. It's about right person, right opportunity at the right time. All those things aligning. And so for me, it's like, look, you know, when people come in and you can tell their genuine belief and excitement about what they're doing, when you ask them, why are you doing this? And they have a really compelling answer about why this is something that they find joy in and they care about so much. I mean, you step back in business and most of the time when people are pitching you companies, they're so fucking boring, right?

9:50Like you're like, this is sinful. You're may even be right. It's just boring. And then you say to yourself, your life is short. Is this really what you're spending your time on? And if you can have that honest conversation, the person says, no, no, no, you don't understand. This is why this is joy for me. This is why it matters. I think these are really important things. I mean, there are other things that come to play. Like entrepreneurs, chronically, I do this myself. You always think it's going to be easier than it is, right? It's really hard. And so you do need people who are going to persevere and find joy.

10:20And I mean, have you ever heard the term like type two fun? What is it? No. Type 1 fun is a thing that's like actually fun when you're doing it, right? Like, I don't know, like a roller coaster or whatever, skiing. Type 2 fun is something that like completely sucks while you're doing it, but there's joy on the other side, like climbing a mountain. Like no one likes climbing mountains. You like having climbed a mountain or like running an ultra marathon. And so I do think that people who have experience with type 2 fun, right, and can enjoy the pain, they think that is a part of what the joy has to be.

10:51But yeah, I think that's like kind of what I've been thinking a lot about recently. And, you know, I think about the things that I've been most excited about or been most proud of in my career. They've all had moments of terrible feeling like there are moments where this is the worst, almost no story in history has been a straight line success. There's always been moments of total disaster and fear and scared and all those bad feelings. But you look back on them and like, you're like, that was a joyful startup. Those people were joyful. The approach was a fun thing. And I think that's honestly what I look for more Not because it's just nice and pleasant, but it is.

11:23But honestly, because I think it correlates with success. Usually all of the greatest moments, when I look back at my life, were preceded by something really hard. Whether it's preparation, getting ready for a sporting event, writing a book or books. I mean, literally right in the middle of this right now, it's like a lot of questioning and hating yourself. I mean, this sucks so bad. And then you got to keep going, right? You got to make it better. You got to keep after. Do you have an example of a time when you're like, oh my God, the world's falling apart. This is terrible. I'm terrible. And then you kind of came through it out the other side.

11:57You know, it's interesting when you say that, here's the honest reaction I have, Ryan, which is, yeah, there's countless examples from business and life. But you know what? I think there's this thing about practicing these experiences that's really important. And I really believe that like sports are a really important part of this. So I'll give you an example. Like last year, you know, I've always been like a reasonably fast runner, but never a serious runner. And last year, for complicated reasons, I ended up with this like random goal, which was to run a sub three hour marathon. Right. And there's no point to this goal.

12:29Right. Like I'm now 42, then 41. Like I'm not the fastest guy in the world. I'm fit enough. Like there's no point. Right. But I was like, you know, goals are important. And like practice is important and practice in pain and perseverance. important. It was funny because I would say that the last few miles of that, I ended up doing it. I made a two 59, like 38. I made it by 20 seconds. It's like the last six miles of that race was a deep conversation with God, right? Cause you can stop at any moment. And by the way, training for this is like, there's no stakes. No one's watching. No one cares. Like you're the only one that cares about this.

13:06Right. But honestly, like finishing that and getting it done, even though it's very painful. And I did it, you know, without a lot of training in the whole nine yards. Those are the types of like practice moments where like this is a disaster. I am literally like falling apart. And then it's worth it for the payoff and for the practice. Two years ago, one of my challenges was to like get my pilot's license. There are people who love flying airplanes. I know people who have gotten super into it. And this is an important part of their identity. They geek out about the hunters. I don't love it. It's fine.

13:36But like I set the goal. I actually find it like somewhat, I definitely have moments where I was like, this is really scary. Like as person, you do your like first solo in an airplane or like things like that. And you're like, this is like pretty terrifying, honestly. You know, on the other side of actually accomplishing the goal, it becomes like these practices you do, which then you bring into the rest of your life so that when shit hits the fan with partners, with a deal, with some stupid shit, you're like, I know these feelings. I know how to think about it. and I can kind of move forward as opposed to fall apart.

14:06Those lessons, whether it's from sports or physically punishing yourself, like trying to finish a marathon under three hours, which is amazing. I think they're so portable. You're creating evidence for yourself that you can do something really hard. When like no one else, especially in a marathon, yeah, everyone's worried about themselves. They don't care about you. Like maybe a few people that love you, but other than that, that's it. So it's really all about you saying, proving to yourself and creating that evidence so that when you face the next hard thing, whether it's in business or in a relationship or all of the above, you have that evidence to point back to say, I've done this before.

14:40Not like this exact thing, but a version of this. I can do this. I think exceptional leaders, people who have sustained excellence over time, the 650 plus I've talked to over the past decade, Sam, are really good at this. They're really good at putting themselves in the pain cave and getting out regularly. and they intentionally do it. They manufacture hardship so that in the future, they're better prepared to handle the inevitable adversity that they're going to face. And this just seems to be a commonality I've seen. You know, my kids are really into Carlos Alcaraz, right? Versus Sinner, right?

15:14He's going to be the two best tennis players in the next decade, right? And it's really fun to watch them. And it's funny because one you see in Alcaraz, the first thing I was talking about, which is joy. You can just see he is exuding joy. And I think that is an important thing. Like he'll be successful in tennis because he freaking loves it. But then the other thing to your point is like, you know, that like part of the reason these guys, I believe are going to dominate tennis so much is like once you get in a position where you're getting experience winning, it compounds, right? Because like when you're, you know, down two sets in a final and you're like, I've been here, I can come back from this.

15:50So much of these things are mental. And so however you're figuring out to practice it, for me, it was, you know, I think running has been an important part, even though I've never been that serious, even back to high school, the like purity of racing and pain and running, I think has actually been an incredibly important set of lessons for me, right, that you kind of carry forward. And I will say like, it's not a deal breaker for me. But when you kind of are looking for leaders in companies, the evidence that they've gotten through that they enjoy the process that they can embrace the suck, so to speak.

16:23And it's not just like you embrace it and suffer through it, but it's like you actually kind of love it. Again, these are all correlations and they're always exceptions, but I kind of think it's important. There's little things like in the summer here in Ohio, where I live, it gets super hot and muggy. But when I go on my walks, I want to wear long sleeves, long pants, and a weighted vest. Because I think you need to suffer, right? You got to regularly suffer in doing that. It's like, I'm not hot to my kids. We're not complaining about air conditioning in the car. Sometimes we need to write a book about that someday.

16:55And their dad wouldn't let them turn the air conditioning on. I still turn it on. I turn it on, but sometimes get to the back as quick as they want. Right. My point is though, like, I think the voluntary hardship, it's not even that hard, dude, just to be a little bit hot when you put on a weighted vest and go out and walk, but it's just the practice of regularly doing it. So then whatever the next hard thing is that I'm not planning for, or I don't know what it's going to be. I'm good. I'll get through this. I got this. I think that's really what it's all about. Yeah, I'll tell you what's funny.

17:23You brought my dad initially, again, who has a huge influence in my life. And I'll tell you something really interesting about this. I'm actually, I'm very dyslexic. I had a lot of hardships learning how to read when I was young. So I basically, this didn't get discovered until late because I was reasonably charismatic and could kind of fake my way through it a bunch. But eventually, you know, things catch up with you. And by third grade, they're like, Sam, you're doing great except for one problem. You can't read. It was pretty painful. I had to go some extra activities and like really like it was a painful social experience.

17:50It was a painful in a lot of ways. And I remember at the time I was pretty upset about this. And my dad said to me then, I'm happy about this. I was like, what are you talking about, dad? You know, like a little kid, it's probably eight or nine. He's like, listen, Sam, it's like you've grown up in a privileged household. You've had every advantage. You're gonna have a lot of advantages in life. And you're gonna learn how to get through this, right? And I, you know, I think the worst case scenario is that you just don't have any hardships. and you're fine. And like, this will teach you a lot. It's tough.

18:19I don't think you want to like wish hardships on your children. But I do think when you see them, you know, as thinking of as opportunities for them to grow and learn, because that is kind of how you find great success. And I think really satisfaction, I think is really important. How do you do that? I mean, you're a wealthy guy. How do you do that as a dad for your kids? So my kids are very young, and I'm still figuring it out is the honest answer. And again, I don't wish hardships on them. I just when they come and they always will come, right? You want to kind of have the right attitude and help coach them on them.

18:48Look, here's what I will say. I'm sure you're a dad too. You know, there's this whole culture, especially I think in the upper middle class around tiger dadding sports. And for a long time, I was like, this is insane. Like, what is the kid's soccer? Like, what are you doing? This is ridiculous. I actually think I have more sympathy for it now than I did before, because I think it comes from whether it's misguided or not a similar mentality in place. Which is, you know, if you grow up with built in hardships, that's brutal, but you're going to learn lessons, right? And like, you're going to, it's going to make you strong.

19:21If you grow up with no hardships and wealthy suburb and a nice place and whatever, you don't have those things. I think maybe subconsciously a bunch of these dads are out there manufacturing hardship, manufacturing competition in kind of silly ways, but actually kind of understandable ways with that, like, maybe not even conscious goal in mind, right? Is almost the way I think about it. So, you know, look, our kids are very athletic. They love sports. I see opportunities to push them pretty hard in sports and running. And all these things, we do it and we do it with joy. And it isn't like a hardship.

19:52But, you know, I think there is a mentality around that that I understand. Well, there's so much to learn from it because when you do have a lot of privilege or somewhat of a setup to where you have kind of everything you could want and need, I want you to lose sometimes. And it's hard to manufacture that, but sports does it for you as a parent. volleyball is a big one in our family, soccer, volleyball, you could win a set 25 to 23. So that means you lost 23 times. You had to respond to adversity 23 times throughout the course very quickly. Boom. You just lost right back up, right back. Get up first, like get up.

20:32And you know, I'm biased. I played all growing up and in college and after college, my family, my brother did like, so we're very biased towards that. And you can learn that in other ways, but I do think that's a really good one, especially as a kid, because you don't have to be like super athletic to keep doing it. Maybe as you advance, you do. Sam, I want to get to your story now. You mentioned you're dyslexic and yet you still get into Harvard and I heard and watched other podcasts that you actually worked really hard and got good grades. You didn't like drop out and start a company. You wanted to graduate and get good grades and then get a boring job at a place like Bain, which is not, it's an amazing job, right?

21:07But that's what you did. Let's run through your history, starting at Harvard and then why you first decided to go to Bain. Yeah, I mean, like, look, think about it this way. I grew up with like two narratives going through my head, if you kind of want to psychoanalyze it. One narrative was I had a very entrepreneurial father who, I mean, I think there was a joke on Wall Street that they called him the unguided missile. Very successful, did amazing stuff, but just like all over the place, right? And really into entrepreneurship and things like that. And I was around entrepreneurs. It was exciting.

21:35It was really internet. Wait, he took you to meetings and stuff? Oh, yeah. Like I was in starting in high school. I was, he was taking me, especially in the early internet to this entire generation of meetings. I had no business being in, but I learned so much, you know, I was there for the day they IPO. It's like general magic, basically the start of Android came from that. And like, so I was always great documentary on that. Yeah. Yeah. Believe it or not. If you know that documentary, there's a scene in it where they talk about the banker who took his shirt off to win the deal. I'm like 99 % sure that was my dad.

22:06but um i had all this exposure on for i was very excited i was you know i had fun internships but remember i was very dyslexic kid who worked his ass off to like catch back up and like get good grades and get into harvard and was kind of told to like check the next box you know i graduate i did not slack off i graduated five beta kappa you know at the top of my class you know i didn't get a suma i graduated magnet but still the thing that became i think an interesting thing for my first job is I had these two polls. One is I wasn't close with him, but I didn't know Mark undergrad. Right. And I was very excited about the early days of Facebook.

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22:41I had actually worked closely with my dad and had been his lead, I think one of his lead investors, if not his lead in six degrees, which was kind of the precursor and social networking. I had a lot of thoughts and perspectives on the stuff. It was really exciting. And so I almost went and worked for Mark. The other job offer I had was the most boring job offer in the world, which was Bain & company, but it was the gold checkmark, right? Like people wanted the Bain job. No one wanted to go be an entrepreneur. People wanted the Bain job. And so it took me an extra few years of going getting gold stars.

23:08I still was on the I need gold stars. I need to prove that I can get gold stars thing, even though like I was very torn about it because in my heart of hearts, God, I love the innovation and the internet and what was going on. I think I understood a lot more and had a ton more exposure than most people at that point. By gold star, you mean like someone telling you like you're smart you're good sam yeah you want the adults to tell you you're good right because you don't you don't believe it yourself enough yet or you've worked too hard effectively and like been too trained on gold stars and it's it's one of those things where it's a really hard balance i know plenty of people who have no gold star instinct and some of them are wild some are really successful a lot of them aren't because they just do not care Then you have this other class of people who like really care about good grades, right?

23:54They really care about like traditional measures of success Candidly, like they just don't ever do anything interesting And so there's this interesting like yin and yang balance. I think you need and for me It took a few extra turns of like get the gold star do the thing you're supposed to do from the adult perspective You know the funny part is I think bane really broke me of that That was kind of the final straw and ever since then i've just been kind of doing wild things but you needed it though. You needed to get that out of your system. I needed to get out of my system. I needed one more turn of the crank of being told by adults I was good.

24:25So two years go by on the dot and you decide it's time for me to start something. Yeah, I mean, so reality is a little more complicated than that, but yes, the upshot is, while I almost quit three times during Bain and had really interesting job offers from all sorts of interesting stuff, including very early founders fund before when I was just getting started, et cetera, I did stick it out. and then like quit on the dot with a friend from Bain and we started a company in Brooklyn. All right, what was that company? It was called Drop.io. It was a file strength platform. And it was basically, if we're being honest, it was basically a Dropbox also ran.

25:01Was Dropbox out then? You know, Box.net, Dropbox and Drop.io were all founded relatively similar timeline. I actually don't remember exactly, but it was like somewhat concurrent, it was what I would say. and for us the big thing for me was i was really excited about aws and the idea that you could build businesses on top of the early aws it was kind of funny there's another place you end up in rooms where you had no business being is when they first formed the amazon web services customer advisory board i was on it it was like the cto of the mlb and like all these very fancy senior people and then me and like i would because i like represent i was actually we're spending a lot of money with them and like we were kind of kids in brooklyn with a startup which was a weird thing then.

25:44And so, you know, you talk about wandering through life into weird rooms. That was a funny one. And then so how long until you mentioned Mark, Mark Zuckerberg decided to, it sounds like Aqua hire you, but what happened there in that story? Yeah, I mean, basically, it's always a bunch of things intersecting. But you know, Mark and I, I've always thought the world of him. We knew each other, we weren't super close in college, we became closer over time, just socially, in a lot of ways, we always talked about the internet and what was going on and what was most important. And I think it was in early 2010, the basic tone of it ended up being kind of coming to the conclusion that Facebook really mattered in the world.

26:22And what I was doing just didn't, right? It was not a terrible business. We were growing, we had customers, it wasn't like a nothing. It wasn't on a trajectory to be like an important thing, right? And Mark was just like, just come run the profile team. I really want to like reinvest in profiles. What had happened is newsfeed had become like the only thing that mattered in Facebook. And Mark wanted to like reinvigorate other services. And so at a certain point, watching these things and knowing how much, you know, I do believe, I believe in particular in the importance of digital identity and where that was going, it was kind of like one of the things like, okay, fine.

26:54This is clearly the right thing to do. He acquired the company, I moved out, took over the profile team originally, ended up building the identity team and reporting to him and running a bunch of the product groups. So 2010 to 2014, it was a huge growth period for Facebook. Wild period. Wild period. You're right in the middle of it, making it happen. What are some like leadership lessons you learned from working for Mark? I mean, Mark is an incredible guy. I mean, I can go in so many directions on this, but I think the upshot is I had a blast working at Facebook for him in that period. I had a blast building teams and like I'm very proud of who we've recruited and a lot of the things we did.

27:30For Mark specifically, look I think there's a few things that come to mind one is I'll go back to joy the guy is joyful right and like people I think miss this about it it's like he loves what he's building he loves the game of it he loves the whole nine yards like it's not you know people are always like well Mark she's gonna retire me like I don't think so like I think Mark actually loves what he's doing and I think he has a lot of fun with it I think he's deeply competitive he's deeply joyful and like that is infectious. And that style of leadership, I think is amazing. And so I think that's like a really important, authentic place to lead from.

28:05I think that Facebook in that era was probably one of the greatest concentrations of talent in like the history of the world, right? I don't mean this myself, you know, I got to be along for the ride, but you just look at it, there's all these factors that came to play that had to do with the dot com crash and kind of the early internet and things like that. It's like, you just looked around the room, you're like, it's, Mark is an incredible leader, but one of the most important things is the setup, which he obviously put together and leads. This is an incredible team. I think that's something you just can't undercount when you're working at that scale.

28:38You mentioned the word joy a number of times. You, your dad, the people you like to hire. With that said, there are a lot of examples of people who have this healthy chip on their shoulder. maybe not healthy actually, but they have a chip on their shoulder and that propels them to win seven super bowls like Tom Brady or to Kobe or MJ getting cut in his hall of fame speech. He's just talking about all the slights and he's the greatest ever. I know I'm leaning on sports, but this happens in business too. So how do you mix this dichotomy on one side, this joyful person who does it out of love and care and joy, but maybe cause I sense Mark maybe has both, but, and maybe you do, I don't know others.

29:19I sense more joy out of you. What about like having that chip say, I'm going to prove you wrong. I can do the thing that people don't think I can do. Again, as I said, there are seasons for things. I think it's pretty hard to argue that Mark has to prove anything to anyone at this point. Right. Is what I would say. So I think, again, like, I think that's like the joy is the long-term one that keeps you in the game in a lot of ways. Like, look, I love a competitive chip. I think revenge companies can be great. But like, let's talk about like, I would argue that like Rippling is probably one of the world's great revenge companies.

29:48Right. Parker. Right. I don't know if you know the story. Oh, yeah. I know the story very well. Yeah, my wife actually works there. Got it. So, like, Parker's awesome. You know, Parker? Parker's a joyful guy, right? Like, and I actually think that's kind of one of the great tricks of a lot of these things. I actually, it's not clear to me that competitive spirit chip on your shoulder thing and joy can't go hand in hand, right? There might be places where, like, one dominates. And, like, there are companies that are, I think, you know, I'm not going to name names, but I think you can look across the universe and be like, that seems like kind of like a mean company, if that makes sense.

30:22Like that's a company that's run out of like anger and fear versus one that's run from like a place. It's like, you know, this is like Star Wars 101. It's like the light side and the dark side of the force. But there's some like deep truth to it, which is like the anger is very powerful in a moment. Michael Jordan can come up with reasons that his immediate enemy like in a game, like slighted him that are ridiculous to motivate him like with a little bit of extra pizzazz, fine. But I just don't think it's like sustaining. And so I think for me, it's like the long-term success is sure you can have chips and be competitive there's nothing wrong with wanting to win in fact i actually think you have to you have to come up with reasons why you want to win that are outsides or you just like life's too big and long like i face this personally like i like there's a body that's been successful in you know i'm proud of a lot of the work i've done but like it is a question of like what am i doing right now you know what i mean like i can try to find another solana that'd feel nice but like does that really matter like you know what i mean like what are you Like, how do you think about that?

31:16Right? Yeah. Can you tell the Solana story? It was like a 2 ,000 % return or something insane like that. What happened there? I put in about$400 ,000. I was the third person to send them a check. Was this individually done or was this with the fund? I would be insanely rich. I was going to say, nice if so. But anyway. It's still done just fine. I wouldn't worry about it. But yeah, I mean, that was a great example of$400 ,000. You know, we exited two RLPs who at some point you have to pay them back. about 2 ,000 times their money. If you held it, it'd be a lot more. But basically, we put it and call it on a 20 post that things worth$100 billion today in five years, or whatever the timeline is.

31:55It's pretty wild. Here's the thing about that. You've got to ask the question of, these things are all serendipitous in a lot of ways. The way I ended up doing that deal was the intersection of two very distinct things at the same time. One was just the idea of, I really believe there's room for an ETH killer, right or something that's not ETH that's going to win you know I've been around the crypto world since a relatively early period I was a personal seed investor in Ripple I had done Bitcoin very early personally you know I had been the first investor and really the only investor for quite some time in Venmo so I had some experience and like perspective on the payment space but then you know you think about these narratives we hit this point I was like there's gonna be something that takes some of the ideas of Ethereum and does it better and so we were looking for that right And I was looking for that.

32:40And Solana wasn't the only one we did. We also did Algorand early and a few others, a lot of which were successful, but nothing like Solana. And then at the same time, people and relationships matter. And the reason I ended up doing Solana was actually because of Raj Gokul. And Raj is someone, believe it or not, I had originally met because I was trying to recruit him to work at Facebook years and years earlier. I really liked him. It didn't work out, but I followed him through three other startups he did, right? All over the place. And I was like, you know, we never invested. I never invested in them.

33:10I wasn't quite there, but I really liked him. And then I would run into him at a crazy crypto meetup. And he's like, I have a new company. And it's the theme you love. And I've always liked Raj and believed in him. Right. And it kind of all came together in like a really serendipitous moment. And so you think that's kind of, you know, how that one played out. And like, it wasn't a straight line. I think this goes back to the whole like, be joyful, but it's always an ups and downs. Like I remember running into the founders, you know, a little before they launched or right after even. And they had launched the thing.

33:37They didn't know what it was for. It was like all this. And like they'd gained a bunch of weight. They look like shit. It was like clearly a very rough moment for them, but they're fundamentally joyful people doing a joyful thing and expressing ideas they're excited about. And you know, it's not the only factor, like there's a bunch of other stuff at play, but it matters. So I want to reference an interview you did. I don't remember how long ago it was with something that I've picked up after doing this podcast for 10 plus years. I'm asked frequently, maybe during Q and A's of keynotes or something like, what is the one thing you've learned from all of these brilliant people.

34:08What is it? And you know, it's, it, there isn't one thing. There's a million things, right? I've written multiple books about those things, but if you force me to say one of them, I'll say, you know what? And this isn't going to be as inspiring as you're hoping. Nobody knows what they're doing. We are all figuring it out as we go. And I know you've said something similar to this. Now that you're more into the world beyond Bain, I just love to hear you kind of riff on that. I mean, I couldn't agree more. That was the thing for me at Bain is I, you know, you go and I still had reverence for these big things.

34:36And like, you know, you worked to, you're not supposed to say the names, but like I went and like optimize the peanut M &M line in Hackettstown, New Jersey. And you work with these big fancy companies and you're like, you guys have no idea what you're doing. And like, that's very freeing. Cause like once you realize no one. It's inspiring. It's very inspiring. Well, you can take it one of two ways. You can take it very cynically. That's the wrong lesson to take. The other would be like, oh wow, that means I'm good. I can figure this stuff out. And the people who are really successful, you know, look, it's tough because you don't want to say it's all random.

35:04It's not right. Like it's not random. The people who are the most successful people in the world, it's not like they just got lucky. That's not the right way to think about it. But if you spend enough time in rooms with them for long enough, you realize they're wrong about all sorts of things. They've got all sorts of weaknesses themselves. That's cool. That's being human. But there are a few key traits where like it's a tough thing to balance. So, you know, I'm like a professional seed investor, right? Like what I do is I want to go and find things super early, help people form the businesses, be their first check.

35:34You're analyzing the people and the space and not much else. And you know what the thing is about seed investing? You're mostly wrong. You mostly lose money. It's the only type of finance in the world where you're usually losing money. It's a very interesting discipline as a result. And I think when you do that enough, what you start to realize is there is a random walk to it. 100%. You can't control everything. You shouldn't even try to. That can make you quite cynical. goal. It's almost like playing a sports game where like you score goals, but the number of points you score is almost random, right?

36:09Like, and so like, and someone's like, oh my God, that person has a hundred points. You're like, yeah, like they scored a goal that happened to be a hundred point goal. Like they're not better. So this is weird thing of like competing in something with so much randomness in it, if that makes sense. But if you can embrace that and embrace what it is, it's, it's great, you know, but it is a tough thing to kind of balance, right? To be like, I want to work hard. I care about it. It's not all random, but there's a lot of randomness to it. You want to be the first check. You want to be in super early.

36:39What does your day-to-day look like? Because you can't just follow the crowd or the other institutional investors. You're getting in before all of those guys get in. What does your normal day look like? And I'd say not only that, but I'm a real snob about it, Ryan. Which is like, if other people want to do deals, I don't want to do them. It's an ego thing as much as anything else. I'm like, well, just go get the money from them. They'll pay more. I think one of the most insulting things you can call someone is like a market participant. Yeah. Right. It's like incredibly insulting. But yeah, I mean, like, what does that mean?

37:10I spent a lot of time programming in the last month and I've been having a lot of fun doing it. I write a lot. I've come to the conclusion that one of the best ways to learn things is to post wrong things on the internet and let people correct you. Right. I think it's like this constant conversation and exploration trying to find interesting people and interesting ideas. And that's kind of how I look at it is I almost joke sometimes that I feel like a tenured professor of capitalism, right? Which is like, I'm responsible to make a lot of money over the long term by being very right every once in a while with permission to be wrong all the time.

37:46It's really fun. There are ups and downs to it, of course. There's challenges to it. But I think, you're like, what's my day? I meet with some people, read some stuff. I write some stuff. I come up with an idea and explore how to do it or program it or design something. It's a very weird job that way. Are you partially while you're shipping work online? I mean, I've read a ton of it. Really good writer. Not surprising given just the way that you've operated. Are you just trying to draw people to you? Is that part of it? Are you trying to create this magnetic effect for drawing the types of people that are down with your style of writing and ideas to come to you with ideas?

38:27Or how does it work? All of the above. I mean, I think one of the important things is like, it's not just about drawing people to you. In fact, I actually think it's just as important to push people away. Yep. I'm not trying to be like David Beckham. I don't want to be loved by everyone, right? Like, in fact, I'd really like to be not liked by the people that I don't want to work with because it's just too much volume. Like the internet's infinite. And I think the way you do that just by being really authentically yourself and like being unafraid. And then, you know, the beauty of the internet is it's so big, the right people find you and the right people engage you and you kind of go back and forth with them and that leads you to other interesting people and you just have to be like voracious and open.

39:04I'll be totally honest with you, Ryan, like one thing I've had a little bit of a struggle with, I think recently is in some ways, like because some of the stuff I've written over time or whatever has gone more viral, it's actually made my screening harder because all of a sudden there's a bunch of people who like want to chat who like maybe aren't perfect targets. We're like having a slightly more specific profile in the venture capital community. So I'm trying to figure out how like navigate that, right? Like all of a sudden, like my DMs are like destroyed in a way that they weren't destroyed two years ago.

39:37It's a solvable problem to be clear, but you're like, what are you writing? Why are you writing? It's like, there's a bunch of stuff I do explicitly and implicitly. And yes, I do want to attract the right people that get it and make sense for me. They're going to provide the type of engagement that's going to be professionally rewarding and personally rewarding. But yeah, man, it's also about explicitly pushing away the other stuff because otherwise, you can't find it. Well, I wonder too, I like to hear the stories behind the naming of things. And when you think about Silicon Valley or being out in San Francisco where you are thinking about speed, like let's go fast, move fast and break things.

40:14You worked at that company, right and yet the name of your company is the opposite of that right it's slow what made you choose slow ventures well i'll start with first of all the thing about like move fast and break things move fast and break things was an awesome marketing message because it definitely attracted who you wanted not who you didn't a lot of people who back then would be like i don't want to break things great you shouldn't work at facebook in that era right maybe maybe now maybe when it's build solid infrastructure i was like a different evolution what they need but like Like Slow Ventures, look, there's a reason the name is stock, which is it's funny, right?

40:47Like we have a growth fund that you can call slow growth. Like that's hilarious, right? And if like you think that's funny, then like that's good. If you think that's stupid or like don't get the joke, then like we don't want to talk to you, right? It's the same thing like if you've gone to our, I'm very proud of our website. Every once in a while, someone joins our team and they're like, we need to change the website. And I'm like, absolutely not. you don't get it, which is the website is like me and my two partners. And we're all in Texas. And it looks like a law firm website. That's on purpose.

41:20Like if you don't think that's funny, then like you're not who we want to invest in. And so I do think that those are like kind of the types of things you have to do. And that Slow Ventures as a name is just like, yeah, that's hilarious. Well, I like the idea of taking the work really seriously, but not yourself. And part of, you know, had one of your fellow employees, Jack Raines on the podcast. Hilarious guy. And right. And Jack's, I'm guessing you probably learned of him through Young Money, maybe reading some of his blog posts. And he's really, really funny. And it's hard to do that. And so I'm guessing your website, your ethos, the way that you guys are, you was attractive to him and vice versa with his LinkedIn trolling type posts and all of that stuff almost seems like a perfect match.

42:07Yeah, there's a lot that's there. I mean, I think also it's just in especially in venture capital, the amount of work you do has like nothing to do with how good you are and the outcomes. Right. And so like there are these people out there who like they emulate hustle porn culture or they're like, I'm a VC and I'm working so hard. And you're like, you're missing the point. That's not how this works. Right. And so again, it goes back to understanding how it does work and being on the inside of that and being confident enough to exude that and put that out into the world. Well, also part of Slow Ventures is you've written on your website that big things take time.

42:51They do. And it shows, I assume, your willingness to be with you, right? You talk more about that ethos of we have this understanding that it's not going to happen tomorrow that this stuff takes time. Yeah. I mean, look, every once in a while, once a decade, something just clicks and it actually does happen very quickly. Right. You know, I would argue like, you know, Facebook was my closest experience to that. Like we were just like, oh my God, this just works for a whole bunch of, even that was an incredible, you know, ride from the early days, having watched it, you know, from like a privileged seat.

43:24But look, that was like a pretty pure win from that perspective. You know, most things, you know, I was very involved in like the founding of Venmo. Venmo like was brutal and took so many turns of the crank right early. And there was, you know, you know, I'm actually working with one of the co-founders of Venmo now on a new app, right? Which is like 16 iterations in the making. And like, I'm excited about where it is. We'll see how it goes. This is why, again, the joy and enjoying the journey is so important because I think that is part of the whole ethos is very few things. You can't bank your life on like the quick win, right?

43:57you do kind of have to put it on like it's great people we're exploring a theme you know we're gonna figure it out and there's a difference between that and just straight grinding like one thing i see a lot online it's a subtle distinction but i think an important one is again there's this like we're gonna grind it out culture that i'm actually less down with if that makes sense it is possible to sometimes grind out success at great cost right if that makes sense you're not that good the thing isn't that right but you're just gonna do more meetings and work harder than everyone else i respect it as like an athletic achievement but i actually think it's a kind of shitty way to like grow businesses what i think is much more it's like almost like sailing if that makes sense which is like you get in your little boat and you gotta find the wind and you gotta tack around a bunch but then once you find it once you've experienced an actual tailwind pull from a market, a thing that matters, like things clicking, you have to be patient about finding that moment, right?

44:57And sometimes I think, you know, if anything, I think you can take that's the wrong lesson from a slow venture or how long success takes is just the idea that like, look, if you're doing the wrong thing or running the wrong experiment, just stop. Like, don't grind it out. Like, that's brutal. And like, you're kind of missing a bigger opportunity that's two doors over, right? Like, it's almost the way I would look at it. You again brought up joy, loving the process and this may be way wrong but how much of this focus on love and joy and embracing kind of like the day-to-day love of the process is the fact that your dad died way too young that's an interesting question here's what i basically say to that is one i would say that again you know i didn't experience this firsthand obviously but what he had actually several very close call death experiences throughout his life.

45:47He almost died when he was 39. He had a terrible stroke. He had Hodgkin's in his 20s. And one thing he would always say is that when you have kind of these near-death experiences, when you're supposed to die and you don't, it does make you reevaluate life in a way that's just very hard to experience if you haven't had that. Again, I haven't had that, thank God. But I believe it. It makes sense to me. And so I think he did kind of really embrace that, like, how do you think about enjoying the moment and the day and things like that? you know so i think that's probably part of it but it's also like look it's it's it's i don't know that that's like a complete answer is what i would say i don't like he wasn't like always a joyful person like no one is you know what i mean like he's a human like i think it's a really important thing to propel you this thing i'm trying to remind myself of too because like you know like you go through cycles like this this sucks or like this is like not you're like wait a minute life's great enjoy this you know like this is like and that is kind of it's not just because it's a better way to live, right?

46:43It's also just, I think, how people are more successful. Yeah. Yeah. Well, the optimists are the ones who change the world, right? Pessimists want to sound smart and sound right. And sometimes they are. I don't want to be around that, man. I sense you'd be the dude you want to hang out with. He's really smart, but also is not going to take himself too seriously, but will work hard. But then what's the point, dude? What's the point if we're not going to try to enjoy this thing? You know what I mean? I'm with you. it's funny if you did a poll around town i think i am considered in certain things like somewhat of a cynic on things and i do think your line is right people say this a lot which is like the cynics are right but the optimists have more fun that's totally true the cynics don't change the world though they don't make change happen do they i think it's the the believers of crazy ideas that are willing to go do it the problem with that i agree with you but i do worry especially in this moment that people have almost embraced that mentality too much in certain places to a fault for instance there's a whole generation from my perspective of people right now who are like see the future of everything in ai right and before that it was like the metaverse and before that it was like and i kind of get it because i think one of the things that again timing is everything we were born at like the most unbelievable moment in history i lived right before the internet and i kind of vaguely remember it but like we were like the internet native generation right like a oil dial-up yeah the world completely changed as we were coming up and like we're maybe actually a little bit like honestly i'm like five years too young actually to like have hit it perfectly peter teal is probably exactly the right age right like i'm like a little young, like, but the generational thing is real.

48:29I think you look at that, you're like, oh, my God, in our generation, in our kind of professional careers in this space, literally everything changed in a profound way. And if you're born younger, you just missed it to some degree. And so then you basically are looking for that thing all over again, like everyone wants every successive wave to like, everything changes, the deck is reshuffled. And you're like, if you're being disciplined about it, that's actually not what's going on. So it's a tough one because you want to be an optimist. You want to be in it. But I do think in a lot of places, people try to manufacture that where it's not to their detriment and to society's detriment.

49:02And then you have people like Elon who are so complicated, right? Because on one hand, they are the ultimate marketers of this mentality and vision. And there's power in it and value in it. On the other hand, they do it in non-credible ways, which I actually think is like a detriment to everyone. SpaceX is an unbelievable company, but we're not that close to going to Mars. He knows it. And there's a cynicism to overusing optimism as your tool for excitement, if that makes sense. Yeah, I get what you're saying. I think more broadly, I just want to be around a group of people that have belief, that have joy, that have confidence, that are just into the thing that they're doing and they can pour their whole heart and soul out into it.

49:49Not to like the fake it till you make it types, but the ones who have optimism just in themselves and then people around them that we're going to go and enjoy this thing and get after it, have fun, not take ourselves too seriously. That's really like, I want to be surrounded by that. Yeah, and it's a cultural thing too. I mean, I think the moment we're in right now, there's so much anger and fear and some of it's justified, honestly, but I think big picture, it's like the wrong vibe for great things. Agreed. Agree. Oh, yeah. 100%. One more before we run, man. Let's say you're meeting with somebody who was like you a while ago, recent college grad, they want to leave a positive dent in the world, but they're not really sure how yet.

50:28What are some general pieces of life slash career advice you'd give to them? So the only career advice I consistently, I get people all the time who are like, I want to be a venture capitalist. And first I'm like, maybe like, I know it looks good on paper. Like, yeah, let's talk about it. My only real advice is write publicly. I just really believe in this partially like you got to record the journey. It's partially you need the intellectual receipts, right? Like people like what's the resume and like someone's like I want to work at a venture fund. I'm like, cool, what have you written? If you can't write the check, write me the thesis and timestamp it, right?

51:01Like and like, I just think like it's an incredibly important calling card in terms of like, what do you believe and where do you stand and how do you think about the world? Like writing is thinking if you can't write, you can't think. So like, that's really important. And then I guess the third factor to the way I'm like, really, you should write things down is like people just lie to themselves constantly. It's not like malicious. You will forget or get it wrong. Like human memory is not actually designed for accuracy, right? It's designed for self-justification. And so I think there's like a real factor to being like writing things down, putting them in public space, standing behind them.

51:33You're going to be wrong all the time. It's okay. And like learning that muscle. I think, I think for what it's worth, it's also just like, we talked before about experiencing pain and training on pain and being okay with it. Look, until you've been like deeply flamed on the internet by everyone over something, you're going to fear that, right? Like if you put stuff out there, eventually you're going to say something that people are going to lose their shit about, right? And like, I think even that is another form of just experiencing that's important. I got to get blown up by like the whole internet hating me at least once a year.

52:04Well, I think there's so many things I could talk about when it comes to writing, but one, it makes you a clearer thinker. Putting yourself in the of being a teacher is how you learn. It's the greatest learning tool in the world is to teach. Writing is a great form of teaching. You don't know what you think until you get out of your head onto the page. They're fuzzy thoughts. Then you write it and you understand it. Then you publish it and it works as a way to sometimes draw people towards you, push other people away. There's a million good things that could happen from doing it. I push every leader I work with, the ones in groups, one-on-one, all of them.

52:34Write, write, write. I'd love for them to publish too, but write. Get it out there because you need to become a clearer thinker if you want to be an effective leader and people don't want to do it because it's really hard and it's worth it. If there's anything out there, man, it's so worth it to do it. That's the main reason I sign up for books and sell a deal to a publisher because now I'm on the hook. And now you got like, wait, I thought I knew what I was talking about. No, I don't. Now I got to try to write a whole book about that thing. Wow, this is worth it. What a tough project. So anyway, I could go on forever.

53:04Sam, this is awesome, dude. I really appreciate your time together. Is there anywhere you'd like to send people to learn more about you online i'm like at lesson most places my website is w lesson.com i don't know find me but only if you're like if you i don't know or don't this is great dude i would love to uh continue our dialogue as we both progress maybe record around two and a little bit we could even bring jack on that could be a fun thing to do at some point in the future. It'd be fun to do, man. Love it, man. Super fun, Ryan. Nice speaking with you. Thanks, man.

53:37It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, ryan at learningleader.com. Let me know what you learned from this great conversation with Sam Lesson. A few takeaways from my notes. The advice Sam gives to everyone. Write publicly. You don't know what you think until you get your thoughts out of your head onto the page. And if you publish them so that others can read, you have a record of the journey. Also, you might attract someone to work with. That is how Jack Raines, who was guest on episode number 539, a really good one, caught Sam's attention.

54:20And now they work together at Slow Ventures. And then I loved the through line of this whole conversation about his dad and working exceptionally hard and having joy and excitement for the journey. And maybe it was the near-death experiences that his dad had that led to this mindset. But regardless, it's something we can all learn from. We want to be around optimistic people who have joy and love for what they're doing. And if we want to be around those types, we need to be one of those, have joy and love. And then remember, one of the things that Sam said that we've both learned over the years, nobody knows what they're doing.

55:03We're all figuring it out as we go. You'll never learn unless you go out and actually do the thing. So figure it out as you go, but you got to get started and then iterate, learn, try again, fail, learn, and go again and again and again. It's the only way to get something done. Once again, I would say thank you so much for continuing to spread the message and telling a friend or two, hey, you should listen to this episode of the Learning Leader Show with Sam Lesson. I think he'll help you become a more effective leader because you continue to do that and you also go to Spotify and Apple Podcasts and you subscribe to the show, really important.

55:43And you're rated, hopefully, five stars. You tell all of your friends that by doing all of that, you are giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so, so much. Talk to you soon. Can't wait.

From the publisher

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

My guest: Sam Lessin is a Partner at Slow Ventures, with prior experience as Vice President of Product Management at Facebook and CEO of Drop.io. His career highlights include serving as a key executive at Facebook, leading product management efforts, and successfully co-founding Fin. His current role at Slow Ventures involves investing in innovative startups across various sectors, showcasing his expertise in entrepreneurship and venture capital.

Notes:

  • Key Learnings
    • The 4:30 AM Advantage – Sam's father would be at his desk by 4:30 AM every day, saying, "It's easy to look smart if you have a several-hour head start on everyone else." Early work creates compounding advantages over time.
    • Either Be Early or Be Late, Don't Be On Time – Father's wisdom about timing and seasons. Start your career super early to get ahead, or strategically wait and come in later. Timing matters more than perfect preparation.
    • Joy as the Ultimate Competitive Advantage – "I just don't think that in the long run, angry people win." Look for joyful people in hiring and partnerships because joy is sustainable while anger burns out.
    • Type Two Fun Builds Resilience – Type 1 fun is enjoyable while doing it (rollercoaster). Type 2 fun "completely sucks while you're doing it, but there's joy on the other side" (climbing mountains, marathons). Entrepreneurs need Type 2 fun experiences.
    • Practice Voluntary Hardship – Sam ran a sub-3-hour marathon and got a pilot's license not for love of activities, but for "practice moments" of perseverance. Creates evidence that you can handle business adversity.
    • Right Person, Right Opportunity, Right Time – Don't ask "is this a great person?" Ask, "Is it the right person at the right moment?" Success requires all three elements to align, not just talent.
    • Write Publicly for Intellectual Receipts – "If you can't write the check, write me the thesis and timestamp it." Writing creates accountability, proves thinking ability, and builds reputation over time.
    • Nobody Knows What They're Doing – Working at Bain taught Sam that even prestigious companies "have no idea what you're doing." This is liberating—you can figure it out too.
    • Big Things Take Time (Slow Ventures Philosophy) – Most success isn't quick wins. Venmo took "so many turns of the crank." Be patient finding the right wind, then sail fast when you catch it.
    • Embrace Being Wrong Most of the Time – Seed investing means "you're mostly wrong, you mostly lose money." Success comes from being very right occasionally, not being right consistently.
    • The Solana 2000x Return Story – Put in $400K, returned 2000x to LPs. Success came from the intersection of thesis (looking for "Ethereum killer") and relationships (following Raj Gokal through multiple startups).
    • Use Humor and Authenticity as Filters – Slow Ventures website looks like a law firm in tuxedos "on purpose." If you don't think it's funny, "you're not who we want to invest in."
    • Writing Pushes Away Wrong People – "I really like to be not liked by the people I don't want to work with." Authentic writing attracts the right people and repels the wrong ones.
    • Manufacturing Hardship for Privileged Kids – "Tiger Dad" sports culture might be a misguided attempt to create necessary adversity for wealthy children who lack natural hardships.
  • I loved the throughline of this whole conversation being about his dad, working exceptionally hard, and having joy and excitement for the journey. Maybe it was the near-death experiences that his dad had that led to that mindset. Regardless, it's something we can all learn from. We want to be around optimistic people who have joy and love for what they're doing…
  • Nobody knows what they're doing. We're all figuring it out as we go. You'll never learn unless you go out and do the thing. Figure it out as you go. Just get started. And iterate. Learn. Try again. And keep going.
  • Advice from Sam – Write publicly. You don't know what you think until you get your thoughts out of your head onto the page. And if you publish them, you have a record of the journey. Also, you might attract someone to work with. That is how Jack Raines (guest on episode #539) caught Sam's attention, and now they work together.
  • Useful Quotes:
    • "It's easy to look smart if you have a several-hour head start on everyone else."
    • "I just don't think that in the long run, angry people win."
    • "Either be early or be late, don't be on time."
    • "The right question is, is it the right person at the right moment?"
    • "Writing is thinking. If you can't write, you can't think."
    • "I feel like a tenured professor of capitalism—responsible to make a lot of money over the long term by being very right every once in a while with permission to be wrong all the time."
    • "One of the most insulting things you can call someone is a market participant."
    • "The beauty of the internet is so big. The right people find you."
    • "Big things take time."
    • "Life's short. Is this really what you're spending your time on?"
  • Apply to be part of my next Learning Leader Circle.
  • Time Stamps:

    00:11 Sam's Dad's Unique Career Path

    00:39 Life Lessons from My Dad

    04:35 The Trade-offs of Hard Work

    06:57 Betting on the Right People

    07:23 The Importance of Joy in Success

    10:39 Overcoming Hardships and Building Resilience

    20:40 My Journey: From Harvard to Bain

    26:06 Joining Facebook and Learning from Mark Zuckerberg

    29:36 Balancing Joy and Competitive Spirit

    30:15 The Story of Rippling and Parker

    31:48 The Solana Investment Journey

    34:33 The Importance of Writing and Public Thought

    41:07 The Philosophy Behind Slow Ventures

    52:54 Advice for Aspiring Venture Capitalists

    55:46 Future Plans

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