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

Go to www. LearningLeader.com https://www. LearningLeader.com for full show notes This is brought to you by Insight Global http://www.insightglobal.com/learningleader. 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 https://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 https://learningleader.com/leadership-circles/. 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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Hawk?

  This 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/learningleader.

• 0:37Ryan Hawk?

  That's insightglobal.com/learningleader today to learn more. Welcome to the Learning Leader Show. I am your host, Ryan Hawke. 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 Lessin 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.

• 1:20Ryan Hawk?

  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, and then type 1 fun versus type 2 fun, and why we need to be able to have type 2 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.

• 2:05Ryan Hawk?

  So good. Ladies and gentlemen, please enjoy my conversation with Sam Lessin.

• 2:14Ryan Hawk?

  You know, my dad is 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 could go deeper on this. So he became the youngest ever partner at Morgan Stanley.

• 2:29Speaker 01

  Yep.

• 2:29Ryan Hawk?

  And he actually wrote in his book, which is called Lessons Lessons. It's really just about life lessons that 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?

• 2:57Speaker 01

  Yeah, I mean, that's a broad question. The answer is 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, but we spent a lot of great time together. And, you know, he had a, he had a wild career. He used to refer to himself, have you ever seen a movie called Being There?

• 3:13Ryan Hawk?

  No.

• 3:14Speaker 01

  It's great. You should watch it. It's with this character 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 did a ballroom dancing and he, you have to understand he's a brilliant guy. He was 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. You 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.

• 3:58Speaker 01

  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. And he started using an early computer, matching rides between Boston and New York for people who wanted a rideshare. So he, you know, he was doing all sorts of crazy stuff as a kid, just kind of experimenting and learning. And, you know, he found his way into Wall Street that way.

• 4:30Ryan Hawk?

  Wow. What are one or two of the, your favorite learnings that you picked up, whether from reading his work or from him directly?

• 4:38Speaker 01

  I mean, it's really, really hard to compress it down, but I, you know, 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, and 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 head start 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. The thing is, I just remember a lot of like joy and excitement about new ideas and information.

• 5:20Speaker 01

  When he was, you know, a banker, he kind of invented this idea of transaction development. This 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. He became the highest-earning banker on, whatever the numbers are, they're in the book. But the upshot is, is like, you know, he literally was just like, kind of finds his way. Because I think he actually truly loved the people and ideas. And I think that carried into his venture. You know, he got really excited with the internet very early. And 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,

• 6:04Speaker 01

  which is, it means nothing because the East Coast is relevant, but like, 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, this stuff is in rocket science, but I just remember a lot of joy. And I think that's important.

• 6:20Ryan Hawk?

  There are trade-offs to excellence. Being at the office at 4:30 means you're not home with your family having breakfast. What 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?

• 6:38Speaker 01

  Well, I mean, it's funny, you brought up his book. You know, I've obviously read it a few times and you kind of quote out of it. But, you know, 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 like, 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. You 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 it's something about seasons. So my dad would say, since you bring him up and we're talking about him, like 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 again.

• 7:23Speaker 01

  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 like worked hard and showed up first and early every time. Right. And like, that was a strategy. And then candidly later in his life, he didn't go over the Dura Washington Bridge after rush hour. Right. And I think there's another strategy, which is enjoy your twenties and then work really hard later. But I think it's like, it's not one of those things where like, it's so binary. I think there's 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? Right. 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?

• 8:05Speaker 01

  Because no one is always there, you know, people who get rich and lazy, or they have other things going on in their life. Or like, 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.

• 8:22Ryan Hawk?

  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. There's another way of phrasing what you do, or at least one of the things you do. You gotta bet on people, you gotta bet on ideas or the combination of those things. What do you look for in a founder specifically? Let'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 gonna bet on them. What are some of the must haves in those people?

• 8:50Speaker 01

  I'm gonna use the word joy. I think you want joyful people, right? And people who are gonna 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. There 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? And 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.

• 9:35Speaker 01

  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? Like you're like, this is sinful. You might 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 with the person, then 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 into 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 in.

• 10:20Speaker 01

  I mean, have you ever heard the term like type two fun?

• 10:22Ryan Hawk?

  What is it? No.

• 10:23Speaker 01

  Type one 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 two 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 two fun, right? And can enjoy the pain, they think that is a part of what the joy has to be. But 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 you're like, this is the worst. Almost no story in history has been a straight line success.

• 11:06Speaker 01

  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, like it was a fun thing. And I think that's honestly what I look for more and more, not because it's just nice and pleasant, but it is. But honestly, because I think it correlates with success.

• 11:25Ryan Hawk?

  Usually all of the greatest moments. When I look back at my life, we're preceded by something really hard. Whether it's preparation, getting ready for a sporting event, writing a book or books. I mean, I'm 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 gotta keep going, right? You gotta make it better. You gotta 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.

• 11:57Speaker 01

  You 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, right? 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?

• 12:37Speaker 01

  But I was like, you know, goals are important and like practice is important and practice and pain and perseverance is important. It was funny because I would say that the last few miles of that, I ended up doing it. I made a 259, like 38. I made it like 20 seconds. 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, like 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, right? But honestly, like finishing that and getting it done, even though it was 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.

• 13:20Speaker 01

  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 like this is an important part of their identity. They geek out about the planes. I don't love it. It's fine, but like I set the goal. I actually find it like somewhat, I would definitely have moments where I was like, this is really scary. Like especially when 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 these 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.

• 14:06Ryan Hawk?

  Those lessons, whether it's from sports or physically punching 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. So I've done this before, not like this exact thing, but a version of this, I can do this.

• 14:45Ryan Hawk?

  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.

• 14:53Speaker 01

  Yeah.

• 14:54Ryan Hawk?

  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.

• 15:10Speaker 01

  Yeah, my kids are really into Carlos Alcaraz, right? Versus Sinner, right? One and two, he'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 at 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? Cause 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. So 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

• 15:55Speaker 01

  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 incredibly important set of lessons for me, right? That you kind of carry forward. And I, I will say like, it's not a deal breaker for me, but when you're kind of 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. And 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 there are always exceptions, but I kind of think it's important.

• 16:32Ryan Hawk?

  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. Cause I think you need to suffer, right? Like you gotta 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 suffer.

• 16:54Speaker 01

  They're gonna write a book about that someday. Their dad, it wouldn't let them turn the air conditioning on, but yeah.

• 16:58Ryan Hawk?

  I still turn it on. I turn it on, but sometimes it gets 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.

• 17:22Speaker 01

  Yeah. And I'll tell you a funny, I'll tell you a funny, you 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. Like I had to go some extra activities and like, really like, it was a painful social experience. It was 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 that? You know, I was like a little kid. I was probably eight or nine. He's like, listen, Sam, it's like,

• 18:03Speaker 01

  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'll teach you a lot. It's tough. I don't think you wanna 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.

• 18:33Ryan Hawk?

  How do you do that? I mean, you're a wealthy guy. How do you do that as a dad for your kids?

• 18:37Speaker 01

  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 wanna kind of have the right attitude and help coach them on them. I look, 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, why is the kids 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 gonna learn lessons, right? And like, you're gonna, it's gonna make

• 19:20Speaker 01

  you strong. If you grow up with no hardships in a wealthy suburb in 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. But, you know, I think there is some mentality around that that I understand.

• 19:55Ryan Hawk?

  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. And 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 could learn that in

• 20:39Ryan Hawk?

  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? But, but that's what you did. Let's run through your history, starting at Harvard, and then why you first decided to go to Bain.

• 21:14Speaker 01

  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 psychoanalyze it. One narrative was I had a very entrepreneurial father who, I mean, I think there was a joke on Wall Street that was, 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. It was early internet.

• 21:35Ryan Hawk?

  Wait, he took you to meetings and stuff?

• 21:37Speaker 01

  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, the day they IPOs, and like General Magic, basically the start of Android came from that. And like, so I was always,

• 21:55Ryan Hawk?

  Great documentary on that, yeah.

• 21:56Speaker 01

  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.

• 22:06Speaker 01

  But I had all this exposure on, I was very excited. I was, you know, I had all these fun internships. But remember, I was a 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 graduated, 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 summa, I graduated magna, but still. The thing that became, I think, an interesting thing for my first job is I had these two poles. One is, I wasn't close with him, but I did know Mark undergrad, right? And I was very, I was very excited about the early days of Facebook. I had actually worked closely with my dad and had been, I think, one of his lead investors, if not his lead in six degrees,

• 22:47Speaker 01

  which was kind of the precursor in social networking. I had a lot of thoughts and perspectives on this 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 and Company. But it was the gold check mark, 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. I 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.

• 23:22Ryan Hawk?

  By gold star, you mean like someone telling you like, you're smart, Sam. You're good, Sam.

• 23:26Speaker 01

  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 of them 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? They 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.

• 24:09Speaker 01

  You know, the funny part is I think Bain 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.

• 24:19Ryan Hawk?

  You needed it, though. You needed to get that out of your system.

• 24:21Speaker 01

  I needed to get it out of my system. I needed one more turn of the crank of being told by adults I was good.

• 24:25Ryan Hawk?

  So two years go by on the dot and you decide it's time for me to start something.

• 24:31Speaker 01

  Yeah, I mean, so reality is a little more complicated than that. But yes, the upshot is, 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 it was just getting started, etc., I did stick it out. And then like quit on the dot with a friend from Bain and we started a company in Brooklyn.

• 24:52Ryan Hawk?

  All right. What was that company?

• 24:53Speaker 01

  It was called drop.io. It was a file sharing platform and it was basically, if we're being honest, it was basically a Dropbox also ran.

• 25:01Ryan Hawk?

  Was Dropbox out then?

• 25:03Speaker 01

  You know, box.net, Dropbox and drop.io were all founded relatively similar timeline. I actually don't remember exactly, but it was, 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. And it was, it was kind of funny. There's another place where 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 would like represent, I was like, we were 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. And, and so, you know, you talk about wandering through life into weird rooms. That was a funny one.

• 25:49Ryan Hawk?

  And then, so how long until you mentioned Mark, Mark Zuckerberg decided to, it sounds like Aqua hire you, but what, what happened there in that story?

• 25:57Speaker 01

  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. Again, 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 and 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 a trajectory to be like an important thing, right? And Mark was just like, just come run the profile team. I really wanted to like reinvest in profiles. What had happened is News Feed had become like the only thing that mattered in Facebook and Mark wanted to like

• 26:42Speaker 01

  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 those like, okay, fine. This 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.

• 27:04Ryan Hawk?

  So 2010 to 2014 was a huge growth period for Facebook.

• 27:08Speaker 01

  Wild period.

• 27:09Ryan Hawk?

  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?

• 27:16Speaker 01

  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 recruited and a lot of the things we did. For 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 going to retire me. 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. And I think he's deeply competitive. He's deeply joyful and like that is infectious and that style of leadership I think is amazing.

• 28:01Speaker 01

  And so I think that's like a really important, authentic place to lead from. I 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 so that's like, you just looked around the room and you're like, it's, yeah, Mark is an incredible leader, but like one of the most important things is the setup, which he obviously put together and leads, like this is like an incredible team, right? And I think that that's something you just can't under account when you're working at that scale.

• 28:38Ryan Hawk?

  You 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, 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 Dukobi 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.

• 29:07Speaker 01

  It does.

• 29:07Ryan Hawk?

  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, because I sense Mark maybe has both, but, and maybe you do, I don't know, others, I sense more joy out of you. What about like having that chip? Let's say, I'm gonna prove you wrong. I can do the thing that people don't think I can do.

• 29:28Speaker 01

  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.

• 29:33Ryan Hawk?

  Right.

• 29:33Speaker 01

  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. Right? Parker, right? I don't know if you know much, you know the story?

• 29:51Ryan Hawk?

  Oh, yeah. I know the story very well. Yeah. My wife actually works there.

• 29:55Speaker 01

  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 gonna 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. Like, that's a company that's run out of like anger and fear versus one that's run from like a, it's like the, 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

• 30:39Speaker 01

  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 the reasons why you Want to win that are outsized or you just like life's too big and long like I face this personally like I like There's a body has 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 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 right?

• 31:17Ryan Hawk?

  Yeah, can you tell the Solana story was that like a 2000% return or something insane like that? What what happened there?

• 31:23Speaker 01

  I put in about $400,000. I was the third person to send them a check.

• 31:28Ryan Hawk?

  Was this individually done or was this with a fund?

• 31:31Speaker 01

  Fund I would be insanely rich if it was just.

• 31:32Ryan Hawk?

  I was gonna say nice if so, but anyway.

• 31:35Speaker 01

  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 to our LPs who at some point you have to pay them back. You know, about 2000 times their money. If you held it, it'd be a lot more, right? But basically, we put in call it on like a 20 post. The thing's worth $100 billion today in like five years, right? Or whatever the timeline is. It's pretty wild. Here's the thing about that. You got to ask the question of like, 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. You know, one was just the idea of I really believe there's room for like an ETH killer, right? Or something that's not ETH that's gonna win. You know, I've been around the crypto world since a relatively early period. I was a personal seed investor in Ripple.

• 32:21Speaker 01

  I had done Bitcoin very early personally. You know, I'd 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. And 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 like I followed him through like three other startups he did, right?

• 33:06Speaker 01

  All over the place. And I was like, you know, we never invested. I never invested in them. I 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 their thing. They didn't know what it was for. It was like all this and like they had gained a bunch of weight. They looked 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.

• 33:51Speaker 01

  Like there's a bunch of other stuff at play, but it matters.

• 33:54Ryan Hawk?

  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 As of Keynotes or something like, what is the one thing you've learned from all of these brilliant people? What is it? And you know, it's, 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'd just love to hear you kind of riff on that.

• 34:31Speaker 01

  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. And like, you know, you worked at, you're not supposed to say the names. Like I went and like optimized the peanut M and 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 knows.

• 34:50Ryan Hawk?

  Inspiring. It's very inspiring.

• 34:51Speaker 01

  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. It'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 I, 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.

• 35:35Speaker 01

  You'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 like, you're usually losing money, right? Because, and like, it's a very interesting discipline as a result. And I think, you know, when you do that enough, what you start to realize is there is random walk to it. A hundred percent. You can't control everything. You shouldn't even try to. That can make you quite cynical. It's almost like playing a sports game where like, you score goals, but the number of points you score is almost random. Right? Like, 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.

• 36:18Speaker 01

  So this 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.

• 36:35Ryan Hawk?

  You want to be the first check. You want to be in super early. Like, what 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?

• 36:50Speaker 01

  And I'd say not only that, but I'm like a real snob about it, Ryan, right? Like, which is like, if other people want to do deals, like, I don't want to do them. Like, 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.

• 37:06Ryan Hawk?

  Yeah.

• 37:06Speaker 01

  Right? It's like incredibly insulting. But yeah, I mean, like, what does that mean? I 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 the wrong things on the internet and let people correct you, right? Like, I just, 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. It's really fun. There are ups and downs to it, of course. There's challenges to it.

• 37:51Speaker 01

  But I think, really, like, what's my day? It's, I meet with some people, read some stuff, I write some stuff, I come up with an idea and like, explore how to do it or program it or design something. Like, it's a very weird job that way.

• 38:05Ryan Hawk?

  Are you partially why 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? Or how does it work?

• 38:28Speaker 01

  All of the about, 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.

• 38:36Ryan Hawk?

  Yep.

• 38:36Speaker 01

  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 is by being really authentically yourself and like being unafraid. And then, you know, the beauty of the internet is so big, the right people find you and they, 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. I'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, my screening harder because all of a sudden there's a bunch of people who like want to chat,

• 39:21Speaker 01

  who like maybe aren't perfect targets, where 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. It's a solvable problem, to be clear, but you're like, what are you writing and why are you writing? It's like, there's a bunch of stuff I do explicitly and implicitly. And, and yes, I do want to attract the right people that get it. And, you know, makes sense for me to like, 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 like explicitly pushing away the other stuff because otherwise you can't find it.

• 40:02Ryan Hawk?

  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, do you think about speed? Like, let's go fast, move fast and break things. You 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?

• 40:23Speaker 01

  Well, I'll start with first of all, you think 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. There's a lot of people who back then would be like, oh, 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 would think a different evolution where they need. But like Slow Ventures, look, there's a reason the name is stuck, which is it's funny, right? Like, like we have a growth Fund that you can call slow growth like that's hilarious, right? And it's 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 like, if you've gone to our, I'm very proud of our website. Every once in a while, someone joins our team.

• 41:08Speaker 01

  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 tuxes and it looks like a law firm website. That's on purpose. Like, 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.

• 41:32Ryan Hawk?

  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 Rains, on the podcast.

• 41:43Speaker 01

  Hilarious guy.

• 41:44Ryan Hawk?

  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.

• 42:07Speaker 01

  Yeah, there's a lot that's there. I mean, I think also it's just, and 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 like, understanding like, you know, how it does work and like, kind of being on the inside of that and like, kind of being confident enough to like, Exude that, you know, and like, kind of put that out into the world.

• 42:45Ryan Hawk?

  Well, also part of slow ventures is you've written on your website that big things take time.

• 42:52Speaker 01

  They do.

• 42:52Ryan Hawk?

  And it shows like your, 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.

• 43:03Speaker 01

  Yeah. I mean, like, 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 of 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. But 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, the whole, 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.

• 43:46Speaker 01

  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? You do kind of have to put it on like, it's great people. We're exploring a theme, you know, we're going to figure it out. And there, 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 is this like, we're going to 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 going to do more meetings and work harder than everyone else.

• 44:30Speaker 01

  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 is like, almost like sailing, if that makes sense, which is like, you get in your little boat. And you've got to find the wind and you've got to 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? And sometimes I think, you know, if anything, that I think you can take that's the wrong lesson from a slow ventures 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

• 45:13Speaker 01

  a bigger opportunity that's two doors over, right? Like, is almost the way I would look at it.

• 45:17Ryan Hawk?

  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?

• 45:35Speaker 01

  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. He almost died when he was 39. He had a terrible stroke. He had Hodgins in his twenties. 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. I, again, I haven't had that, thank God, but I believe it. It makes sense to me. And so I think there is, 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

• 46:19Speaker 01

  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, I think it's a really important thing to propel you. It's something I'm trying to remind myself of, too, because like, you know, like, you go through cycles, like, fuck, this sucks. Or like, this is like, not, you're like, wait a minute. Life scrape. 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? It's also just, I think, how people are more successful.

• 46:46Ryan Hawk?

  Yep. 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?

• 47:08Speaker 01

  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.

• 47:21Ryan Hawk?

  The cynics don't change the world, though. They don't make change happen, do they? I think it's the believers of crazy ideas that are willing to go do it.

• 47:30Speaker 01

  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, I was like, the metaverse. And before that, I 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?

• 48:11Ryan Hawk?

  AOL dial-up.

• 48:13Speaker 01

  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 Thiel is probably exactly the right age, right? Like, I'm like, a little young, like, but the generational thing is real. I 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

• 48:55Speaker 01

  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. And 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 like, we're not that close to going to Mars. He knows it. And there's like a cynicism to like, overusing optimism as your tool for excitement, if that makes sense.

• 49:32Ryan Hawk?

  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, not 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 gonna 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.

• 50:02Speaker 01

  Yeah, it's a cultural thing too. I mean, I think the moment we're in right now, they're like, you know, there's so much anger and fear and some of it's justified, honestly, but like, I think big picture, it's like the wrong vibe for great things.

• 50:16Ryan Hawk?

  Agree. Oh, yeah. Hundred percent. 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. What are some general pieces of life slash career advice you'd give to them?

• 50:32Speaker 01

  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 are 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? Like, and like, I just think like, it's an incredibly important calling card in terms of like, what do you believe in? 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 where I'm like, really, you should write things down is like, people just lie to themselves constantly. It's

• 51:17Speaker 01

  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 these down, putting them in a public space, standing behind them, you're gonna 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 gonna fear that, right? Like, if you put stuff out there, eventually you're gonna say something that people are gonna lose their shit about, right? And like, I think even that is another form of just experiencing that's important. I gotta get blown up by like, the whole internet hating

• 52:02Speaker 01

  me at least once a year.

• 52:04Ryan Hawk?

  Well, 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 position 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, 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, write, write, write. I 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

• 52:46Ryan Hawk?

  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, right? And now you got like, wait, I thought I knew what I was talking about. No, I don't. Now I gotta 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. Sam, 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?

• 53:10Speaker 01

  I'm like at lesson, most places. My website is wlesson.com. I don't know, find me, but only if you're like, if you, I don't know, or don't.

• 53:21Ryan Hawk?

  This is great, dude. I would love to continue our dialogue as we both progress, maybe record around two in 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.

• 53:31Speaker 01

  Super fun, Ryan. Nice speaking with you.

• 53:32Ryan Hawk?

  Thanks, man.

• 53:37Ryan Hawk?

  It 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, [email protected]. Let me know what you learned from this great conversation with Sam Lessin. 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 Rains, who was guest on episode number 539, a really good one, caught Sam's attention and now they work together

• 54:22Ryan Hawk?

  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. We're all figuring

• 55:04Ryan Hawk?

  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 gotta 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 Lessin. 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, and you're rated hopefully five stars. You tell all of your friends that by doing all

• 55:46Ryan Hawk?

  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 of the team. Can't wait.