From Facebook Executive to 2000x Crypto Returns | Venture Capital Masterclass with Sam Lessin

What this episode is about

Sam Lessin shares insights from his journey as a former Facebook executive to achieving extraordinary returns in cryptocurrency investments. He emphasizes the importance of proactive thinking, public writing as a tool for clarity, and reflects on the profound influence of his father, who taught him valuable life lessons that shaped his career and perspective.

Key takeaways

• Arriving early isn't just prep—it's a power play; success thrives on preparation, not just luck.
• Even the fanciest firms are just winging it; confidence often masks the chaos behind the curtain.
• Can't write? Can't think! The pen is mightier in venture capital—clarity of thought means clarity of action.
• Lesson from dad: Hard work and genuine passion can outsmart credentials; character wins where pedigree stumbles.
• Ballroom dancing bred creative problem-solving; standing out often means waltzing to your own unique rhythm.

Who speaks in this episode?

• Ryan Hawk (Host) · 23 min speaking
• Sam Lessin (Guest) · 34 min speaking

What is discussed, and when

1. 0:00 – 5:00: Bain
2. 20:00 – 25:00: Facebook, General Magic
3. 25:00 – 30:00: Facebook, Drop.io, AWS
4. 30:00 – 35:00: Salana, Facebook, Ripple
5. 35:00 – 40:00: Bain
6. 40:00 – 45:00: Slow Ventures, Facebook
7. 45:00 – 50:00: Slow Ventures, Facebook

Notable quotes from "From Facebook Executive to 2000x Crypto Returns | Venture Capital Masterclass with Sam Lessin"

• That was the thing for me at Bane. You work with these big fancy companies and you're You guys have no idea what you're doing. And that's very freeing.

  about Bain · at 0:13

• Way through it a bunch. But eventually, things catch up with you. And by third grade, they're Sam, you're doing great except for one problem. You can't read. And so like I had to go into and it was pretty painful. Like I had to.

  about Secret Service Sam · at 17:48

• But I learned so much. I was there for the day they IPOed like General Magic, which I, which he IPOed, which is like and I it's basically the s the start of Android came from that and like so I was always he.

  about General Magic · at 22:18

• It was called Drop.io. IO. It was a file shank platform. and it was basically it was, if we're being honest, it was basically a Dropbox also ran.

  about Drop.io · at 25:41

• Learned, I think I can go in so many directions on this, but I think the upshot is it, I had a blast working at Facebook for him in that period. I had a blast building teams…

  about Facebook · at 28:19

• Yeah. Can you tell the Salana story? Was that like a 2,000% return or something insane like that? What happened?

  about Salana · at 32:26

• 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. I had been the first investor…

  about Ripple · at 33:28

• It's slow. What made you choose slow ventures? Well, I'll start with Bristol.

  about Slow Ventures · at 42:05

Who and what is mentioned in this episode?

People

• Secret Service Sam — Person · Main guest · 2 mentions
  Primary interview subject; discusses his upbringing, dyslexia, career path (Bain, startup, Facebook), and investing philosophy centered on joy, writing, and endurance.
• Carlos Alcaraz — Person · Referenced example · 2 mentions
  Used as a sports analogy to illustrate 'joy' and the compounding benefits of experience under pressure (e.g., coming back when down in a final).

Companies & orgs

• Slow Ventures — Company · Business focus · 5 mentions · first at 42:05
  The guest's current venture capital firm, emphasizing long-term investments and joy in the process.
• Facebook — Company · Business focus · 8 mentions · first at 23:20
  Discussed as a major platform where the guest worked and contributed to its growth.
• Salana — Company · Case study · 2 mentions · first at 32:26
  Highlighted as a highly successful investment, showcasing the guest's venture capital success.
• Bain — Company · Business focus · 2 mentions · first at 0:13
  Mentioned as the guest's previous employer, where he gained valuable experience before venturing into startups.
• Drop.io — Company · Business focus · 1 mention · first at 25:41
  The guest's first startup, discussed as an early venture in the tech industry.
• AWS — Company · Referenced expert · 1 mention · first at 26:05
  Mentioned in the context of early cloud computing and its impact on startups.
  Was it was like somewhat concurrent was what I would say. And for us, the big thing for me was I was really excited about AWS, right? And the idea that you could build…
• Ripple — Company · Case study · 1 mention · first at 33:31
  Mentioned as an early investment in the cryptocurrency space.
• General Magic — Company · Referenced expert · 1 mention · first at 22:22
  Referenced as an early tech company that the guest's father was involved with.

Full transcript with timestamps

0:00 He also literally would be at the office at his desk by 4:30 in the morning every day. And he always used to say, "It's easy to look smart if you have a several hour head start on everyone else.

0:09 Nobody knows what they're doing. We are all figuring it out as we go." That was the thing for me at Bane. You work with these big fancy companies and you're like, "You guys have no idea what you're doing." And that's very freeing. My only real advice is write publicly. 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 into me the thesis and time stamp it. If you can't write, you can't think. You know, my dad still remains like 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.

0:48 Sure. On this. So he became the youngest ever partner at Morgan Stanley. Y and he actually wrote in his book which is called Lessons Lessons. It's like uh um it's really just about life lessons that I think everybody would would would get value out of reading. All the money that's made from it is also donated to 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. Did can you tell me more about your dad and his uh I think different way to view the world and what you learned from him growing up?

1:25 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. Um but you know 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?

1:43 No. It's great. You should watch it. It's with this character named Chanty the gardener and or and the idea is that you know he just if you kind he's this incredible charact almost Forest Gump like character almost like the this was Forest Gump before Forest Gump just kind of living his life um and wandering into like the most interesting scenarios and situations. So, you know, my my dad bottom dancing and he you have to understand he's a brilliant guy. He was also somewhat of a character. Um was, you know, he went to Harvard uh undergrad, you know, he he kind of I think even that book says, you know, he you know, he didn't grow up wealthy. He wasn't poor, but didn't grow up, you know, particularly wealthy. You know, his joke was, which I think was basically true, he couldn't get dates.

2:22 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 was trying to earn money and he started using an early computer matching rides between Boston and New York for people who wanted to ride share. So he, you know, he was doing all sorts of crazy stuff as a kid, just kind of experimenting and learning and, you

3:06 know, 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?

3:15 I mean, it's really really hard, you know, to compress it down. But I, you know, you know what I'd say honestly is, you know, he was I think there were two things that come to mind. One is the guy worked unbelievably hard, right? you know, 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're the 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. Um and I think he did that um in a big way. So that that's one thing I just remember a lot of like joy and excitement about new ideas and information you know you know when I

4:06 when he was you know a banker you know he did he kind of invented this idea of transaction development this was like in the earliest days of private equity existing and you know he had a 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 you became you know, I think I think for a long time he was the, you know, the 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 find 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 the um largest angel investor on the east coast

4:50 for many years which was as he used to say kind of like being the smartest utilities executive which is it means nothing because the east coast is relevant but like he was the largest and like I just remembered 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 um work hard it's like this stuff isn't rocket science um but I just remember a lot of joy I think that's important.

5:13 There are tradeoffs 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 tradeoffs that it takes in order to do some We'll get to your story in a second, but to do some of the things you've done, it takes it. It's a sacrifice. How do you feel about that?

5:33 Well, you know, it's funny. It happened to, you know, really have it's 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 it, you know, 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 cuz he was, you know, and that's, you know, he has a very honest story about this stuff. So, I think there's no question there are tradeoffs um, you know, I think on these things.

5:56 Look, I think the the thing I would keep in mind is there are seasons for everything.

6:00 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 he has something about season. So, you know, my dad would say since you bring him up and we're talking about him like, you know, either be early or be late, don't be on time, right? And like, you know, he he would he, you know, he talk about how his thing was he, you know, he started his career super early. He started working at Morgan Stanley before he actually graduated from Harvard. He literally just like just showed up and started working. And 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 meant 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, you know, he um he he'd go over the

6:47 river bridge after rush hour, right? And I think there's another strategy which is enjoy your 20s 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 an entrepre as someone who invests in entrepreneur is 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 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 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 fully do it are really important factors to think about.

7:31 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 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? Let's talk about the person right now. What are you looking for in people to you're like, I'm pushing my chips behind them, right? I'm going to bet on them. What are some of the musthaves in those people?

7:59 You know, there's a there's a bunch of things. I think one is I actually 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? And so I say like I just you want to bet on people who are going to be joyful in what they're doing. And and again, this is why I'm so obsessed with it's not about great people, bad people.

8:39 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, right, about why this is something that they find joy in and they care about so much. I mean, you know, you step back in business and most of the time when people are pitching you companies, they're so [ __ ] 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?" Right? And if you can have that honest conversation, the person says, "No, no, no. You you don't understand. This is why this is joy for me. This is why it matters." I think these are really important things.

9:22 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. And I mean, have you ever heard the term like type two fun, right? You ever heard that term? 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 I don't know, 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 ultramarathon. And so I do think that people who have experience with type 2 fun, right, and can enjoy the pain, right? like suffer like they think that is a part of what the joy has

10:11 to be. Um 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. You know, they've all had moments of terrible feeling. Like there are moments like this is the worst, right? Like not no story, 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, right?

10:39 That was a really those people were joyful. The approach it was a fun thing. And I think that's honestly what I look for more and more. Not because like you know it's just nice and pleasant, but it is. But honestly because I think it correlates with success.

10:51 Yeah. 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 sport sporting event, writing a book or books, right? It's a lot of like qu I mean, literally right in the middle of this right now, it's 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 you got to keep after it. Do you have an example of a time when you're like, "Oh my god, the world's falling apart. This is terrible.

11:21 I'm terrible." And then you kind of came through it out the other side. 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.

11:48 And last year, for complicated reasons, I ended up with this like random goal, which was to run a sub3hour marathon, right? And you know this is not like 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? But I was like, you know, goals are important and like practice is important and practice in 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 ran I I ran a 259 like 38. I made it like 20 seconds. But like, you know, I was talking to someone recently. It's like the last six miles of that race was a deep conversation with God, right? Because you can stop at any moment. Like, and by the way, like training for this is like there's no stakes. No one's watching. No one cares.

12:38 Like, you're the only one that cares about this. But honestly, like finishing that and getting it done, even though it's very painful, right? And like, you know, 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, right? And like there are people who love flying airplanes, right?

13:04 Like I know people who have gotten super into it and this is an important part of their identity and like it's like they geek out about the planets. I don't love it. It's fine. Like I it's fine. But like I set the goal, you know? I actually find it like somewhat I would definitely have moments where I was like this is really scary. like as you do your like first solo in an airplane or like things like that and you're like this is like pretty terrifying honestly. Um but um you know on the other side of actually accomplishing the goal it becomes these like these practices you do which then you bring it into the rest of your life so that when [ __ ] hits the fan with partners with a deal with some stupid [ __ ] you're like I know these feelings right I know how to think about it and you know I can kind of move forward you know as opposed to fall apart

13:47 those lessons whether it's from sports or physically punishing yourself like trying to finish a marathon under three hours which is amazing are 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 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." Not 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.

14:34 Yeah. 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 I've seen. I think I think it's only practice to your point and like you know the nice part is you know if you look at like most professionals where like you know there was just a great my kids are really into Carlos Alcarez 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

15:08 and it's funny because one you see in Alcarez the first thing I was talking about which is joy like this guy loves I mean you can just see he is exuding joy and I think that is an important thing like he'll be successful as tennis because he freaking loves it. But 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 it compounds right cuz like when you're you know down two sets in a final and you're like I've been here like I can come back from this like that total that that that so much of these things are mental and so however you're figuring out to practice it right I think are important I mean for me it was you know I think running has been an important part even though I've never been that serious you even back to high school, the like purity of racing and pain and

15:56 running, I think, has actually been an 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 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. And it's not just like you embrace it and suffer through it, but it's like you actually kind of love it, right? I think is again these are all correlations and there are always exceptions but I kind of think it's important right

16:26 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 cuz I think you need to suffer right like you got to regularly suffer in doing that it's like I'm not hot like we're not complaining about air conditioning in the car that's a rule for me like I'm not listen to that we're not to my kids we're not complaining about air conditioning in the car. Like sometimes we need to

16:52 They're going to write a book about that someday and their dad who wouldn't let them turn the air conditioning on. But yeah,

16:56 I still turn it. I turn it on, but sometimes they get to the back as quick as they want. Right. My my point is though, like I think the voluntary hardship, the the the 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 kind of like the pra, as you said, the practice of regularly doing it. So then whatever the next hard thing is that I'm not planning for or I'm not I I don't know what it's going to be, I'm good. Like I'll get through this. I got this. I think that's really what it's all about.

17:25 Yeah. And I'll tell you funny. I'll tell you funny. You brought up my dad initially again who as a huge influence in my life and you again we can kind of go on along with that, but I'll give I'll tell you something really interesting about this which is when I I'm actually I'm very dyslexic. So and I I had a lot of hardships learning how to read when I was young. And so I basically, this didn't get discovered until late cuz 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." And and so like I had to go into like, you know, and it was pretty painful. Like I had to go some extra activities and like really like get way back. I had to go backward.

18:02 It didn't go back in grades, but it was it was a painful social experience. It 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, you know, and I do remember this when I was in college, third or fourth grade. He said, "I'm happy about this." And I said, I was like, "What are you talking about, dad?" You know, I was like a little kid. I was probably eight or nine. He's like, "Listen, Sam, it's like, you know, you've grown up in a privileged household. You've had every advantage. You're going to have a lot of advantages in life, and you're going to learn how to get through this, right?"

18:29 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. And I think you I think with 2020 hindsight it's tough. I don't think you want to like wish hardships on your children, but I do think when you see them, you know, as thinking 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.

18:53 How do you do that? I mean, you're a wealthy guy. How do you do that as a dad for your kids?

18:57 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. 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 dading sports, right? And you're like, and for a long time I was like, this is insane. Like, what is the kids soccer? Like, what are you doing? Right? Like, this is 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 and 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. If you

19:45 grow up with no hardships in a 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, you know, 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 like, you know, I think there is some mentality around that that I understand

20:20 there. Well, there's so much to learn from it because when you do have a a lot of privilege or somewhat of a 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. And so they volleyball is a big one in our family. Soccer, volleyball, you could win a set 25 to 23.

20:46 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 I think I, you know, I'm biased. I played all growing up and in college and after college. My family, my brother did. So we we're very biased towards that. You know, you could you could 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. And I I think that that's a really good one. Sam, I want to get to your story now. You mentioned you're dyslexic and yet you still get into Harvard. I I'd heard and and watched other podcasts that you actually worked really hard and got good grades.

21:27 You didn't like drop out and start a company. Like you wanted to graduate and get good grades and then get a boring job at at a place like Bane, 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 Bane.

21:42 Yeah. I mean like look, I think 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 he 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 and it was exciting. It was early internet.

22:05 Wait, he took you to meetings and stuff? Oh yeah. No, I and there's 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 of meetings. I had no business being in, but I learned so much. You know, I was there for the the day they IPOed like General Magic, which I, you know, which he IPOed, which is like and I it's basically the s the start of Android came from that and like so I was always he

22:30 Great. 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 I'm like 99% sure that was my dad. But the um but um yeah, so so I had all this exposure entrepreneur. I was very excited. I was, you know, I got, you know, had all these fun internships, but remember, I was a very dyslexic kid who worked his ass off, right, 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 gradu I did not slack off. I graduated five beta kappa, you know, at the top of my class. I didn't get a suma, I graduated magnet, but still, you know, it's like and the thing that became, I think, an interesting thing for my first job is I had these two poles. one is I did I wasn't close with him but I did know Mark undergrad right and very I was

23:18 very excited about the early days of Facebook I had actually worked closely with my dad I' been his lead I think one of his lead investors if not his lead in six degrees which was kind of the precursor in 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 baneing company but it was the gold check mark right like people wanted the Bane job no one wanted to go beond entrepreneur. People wanted a bane job.

23:43 And so I 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.

24:02 By gold star, you mean like someone telling you like you're smart on the back. You're good, Sam.

24:07 You You want other 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

24:20 you know it's a really hard balance. I know plenty of people who have no gold star instinct, right? They're just like, and some of them are wild, some of them are really successful, a lot of them aren't because they just do not care, right? 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 like this interesting like yin and yang balance I think you need, right? 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. 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 but

25:03 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.

25:09 So two years go by. I think I read or or heard on the dot. Two years go by and you decide it's time for me to start something.

25:18 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 Bane 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 um and then like quit on the dot with a friend from Bane and we started a company in Brooklyn. Right.

25:39 All right. What was that company? It was called Drop.io. IO. It was a file shank platform. Um, and it was basically it was, if we're being honest, it was basically a Dropbox also ran.

25:50 Was Dropbox out then? You know, it's like it was Box.net, Dropbox, and Drop.io were all founded relatively similarly timeline. I actually don't remember exactly, but it was it was like somewhat concurrent was what I would say. And for us, the big thing for me was I was really excited about AWS, right? And the idea that you could build businesses on top of the early AWS and it was it was kind of funny. This is 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, right? It was like a bunch. It was like the CTO of the MLB and like all these very fancy senior people and then me and like I because I like represent I was 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 it you talk about wandering through life into weird

26:38 rooms that was a funny one uh to be in. And then so how long until you mentioned Mark Mark Zuckerberg decided to sounds like Aqua hire you but what happened there in that story? Yeah. I mean, basically, there's always the there's always a bunch of things intersecting, but you know, Mark and I I've always thought the world of him, you know, we actually, 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, you know, I think it was in early 2010, you know, the the basic tone of it ended up being kind of coming to the conclusion that Facebook really mattered in the world, right? and what I was doing just didn't right it was like it was not a terrible business like we were growing we had customers it wasn't like a nothing but like it just it wasn't on a trajectory

27:29 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 newsfeed had become like the only thing that mattered in Facebook and Mark wanted to like reinvigorate other services and so you know at a certain point watching these things and knowing how much you know I do believe I believed in particular in the importance of digital identity and where that was going. It was kind of like one of those things like okay fine like this is clearly the right thing to do. You know 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.

28:04 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 leadership lessons you learned from working for Mark? I mean, Mark is an incredible guy, right? And I think I've learned, you know, I think I can go in so many directions on this, but I think the upshot is it, you know, 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. 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.

28:53 Like I think Mark actually loves what he's doing and I think he has a lot of fun with it. And I think just bringing that kind of competitive, 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, you know, authentic place to lead from. It's also just like look, I mean, 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.com crash and kind of the early internet things that it's like you just looked around the room you're like it's you know Mark is an incredible leader but like one of the most important things is just in the setup which he obviously put

29:38 together and leads like this is like an incredible team right and I think that that's something you just can't underount when you're working at that scale

29:45 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 Jacobe 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 in business too.

30:14 So how do you mix balance 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 having that chip let's say I'm going to prove you wrong I can do the thing that people don't think I can do

30:35 so for what I think like again as I said there's 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 and 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 how much you know the story and

31:00 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 is like I actually it's not clear to me that like 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 look across the universe and be like

31:29 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 can come up with reasons that his immediate enemy 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, right? And so I think for me it's like the long-term successes. 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. I face this personally. There's a lot of

32:12 things I've 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 salon. That feel nice, but like does that really matter? How do you think about that? Right.

32:26 Yeah. Can you tell the Salana story? Was that like a 2,000% return or something insane like that? What happened?

32:31 Yeah. I mean, we Yeah, we put in I put in about $400,000. We I actually looked this up at one point. I was the third person to send them a check. Um,

32:39 was this individually done or was this with No, through the fund. I would be insanely rich if it just

32:43 I was going to say nice if if so, but anyway, it's still done just fine. I wouldn't worry about it. But like yeah, I mean like that was a great example of like you know that that that was two, you know, $400,000. We exited to our LPS 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, right? But basically, we put it in call it on like a 20 post and like the thing's worth hundred billion dollars today in five years, right? Or whatever the number the timeline is. Pretty pretty wild. Here's the thing about that. One, you 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 like an ETH killer, right? Or something that's not ETH that's going to win. I've

33:28 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. 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 there you think about these narratives like I we hit this point. I was like there's going to be something that's 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 it saw wasn't the only one we did. We also did Algarand early and a few others a lot of which were successful but nothing like Salana.

34:01 So that I'm looking for that and then at the same time people and relationships matter

34:06 and the reason I ended up doing Salana right was actually because of Raj goal right 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. We was didn't work out but like I followed him through like three other startups he did all over the place and I was like 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. 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 a

34:48 little before they launched or right after even and they had launched the thing. They didn't know what it was for. before it was like all this and like they had gained a bunch of weight. They looked like [ __ ] 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.

35:09 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&A of keynotes or something, like what is what is the one thing like what is the one thing you learn from all of these brilliant people? What 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 said something similar to this now that you're more into the world beyond Bane and all your life. I just love to hear you kind of riff on that.

35:47 I mean, I couldn't agree more. That was the thing for me at Bane 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, but like I went and like optimized the Peanut Eminem line in Hacketstown, New Jersey, and you work with these big fancy companies, and you're like, you guys have no idea what you're doing, right? Like, and like that's very freeing cuz like once you realize no,

36:07 it's inspiring. It's very inspiring. Well, you can take it one of two ways. You take it very cynically. That's the wrong lesson to take. The other is be like, "Oh, wow. That means I can 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. Like the people who are the most successful people in the world, it's not like they just got lucky, right? 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. And like that's cool. That's being human, right? It is these but but there are a few key traits where like it's a tough thing to balance and I look I think this is the thing with with so I you know I'm like a professional seed investor right

36:50 like what I do is I I want to go and find things super early help people form the businesses be their first check 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 like there is random walk to it, right? 100%. You can't control everything. You shouldn't even try to. That can make you quite cynical, right? Cuz it's kind of like 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 100 points." You're like, "Yeah, like they

37:37 scored a goal that happened to be a 100 point goal." like they're not better. Like 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.

37:59 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 you you can't just like kind of follow the crowd or the other institutional investors. You're getting in before all of those guys get in. So like what is your normal day look like?

38:15 And 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 like it's a it's like an ego thing as much as anything else. I'm like, "Well, just go get the money from them. They'll pay more." And like I don't want to be like it's I think one of the most insulting things you can call someone is like a market participant. Yeah,

38:35 right. It's like incredibly insulting. I mean, like, what does that mean? It's like 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 like 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? 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 like it's I almost joke sometimes that I feel like a tenure professor of capitalism, right? Which is like I don't 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. And it's really fun. It's not there ups and downs to it.

39:22 Of course, there's challenges to it, but I think when you're like, what's my day? It's a I meet with some people, I read some stuff, I write some stuff, I come with an idea and explore how to do it or program it or design something. Like it's a very weird job that way.

39:38 Do you are you partially why you're shipping work online? I mean, I've read a ton of it. Really good writer. Not surprising given like 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?

40:02 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. Y

40:10 right. 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 and so because it's just too much volume like the internet's infinite people just y like so the question is like how do you create and I think I think the way you do that is 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 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.

40:43 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 or things I've done have gotten like kind of 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 where like having a slightly more specific profile in the venture capital community for what I do. It was like it like it's a better screen. 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. And it's a solvable problem to be clear, but 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

41:31 and, you know, make 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.

41:45 Well, I wonder too. I I like the ideas. 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, you hear about speed. 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? Well, I'll start with Bristol. 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 and not who you didn't. There's 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, right? It's like a different different evolution what they need. But like great screen, right? Um Slow Ventures. Look, there's

42:31 the there's a reason the name is stuck, which is it's funny, right? Like it's like like 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 that's good. If you think that's stupid or like don't get the joke, then 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, right? Which every once like 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.

43:02 You don't get it, right? 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 and it's like that's on purpose. 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, right? Like you could tell and and part of had one of your fellow employees, Jack Reigns, on the podcast.

43:37 Hilarious guy and right and Jack's I'm guessing you 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 this like LinkedIn trolling type post and all of that stuff had to be like a almost seems like a perfect match.

44:04 Yeah, there's a lot that's there. I mean I think also it's just look you know 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 right like it's not like 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 being on the inside of that, right? And like kind of being confident enough to like exude that, you know, and like kind of put that out into the world.

44:49 Well, also part of Slow Ventures is that you've written on your website that big things take time.

44:55 They do. And and and it shows like your I assume your willingness to be with you, right? To be with you. So can you talk more about that ethos of we understand we have this understanding that it's not going to happen tomorrow that this stuff takes time.

45:10 Yeah. Yeah. I mean, look, look, every once in a while, like once a decade, something just clicks, right? 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 was like, "Oh my god, this just works, right?" Like 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 like as an outsider like but look that was like a pretty pure win, right? Like from that perspective, you know, most things, you know, I was very involved in like the founding of Venmo, right? 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, you know, of Venmo now on a new app, right, which is like 16 iterations in the making, right? And like I'm excited about where

45:58 it is. We'll see how it goes. Like these, you know, these things you're back. This is why again like this the 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 that I actually 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. It's like you're not that good. The thing isn't that right, but you're just going to do more meetings and work harder than

46:47 everyone else. I respect it as like an athlete. I expect I respect it as like an athletic achievement, but I actually think it's a kind of shitty way to like grow businesses. Like 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 got to find the wind and you got to attack around a bunch but then once you find it the once you've experienced an actual tailwind pull from a market a thing that matters like things clicking you want to go right it's just like it it's going to take you have to be patient about finding that moment right and sometimes I think you know if anything that the thing you can take that that's the wrong lesson from a slow ventures or how long success takes is just the idea a 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 you're kind

47:37 of missing a bigger opportunity that's two doors over right like is almost the way I would look at it um

47:42 you you again brought up joy like joyy's on the mind 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.

48:02 So, 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 experiences throughout his life. He almost died when he was 39. He had terrible stroke. He had hotkins 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 re-evaluate life in a way that's just very hard to experience if you haven't had that. I I again, I haven't had that, thank God, but I believe it. It makes sense to me.

48:34 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. Um, you know, so I think that's probably part of it. Um, but it's also like look it's it's it's I don't I don't 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 I think that it's I think it's a really important thing to propel you. There's something I'm trying to remind myself of too cuz like you know like you go through cycles you're 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 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

49:20 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 but it's like I don't want to be around that man like I I sense like you'd be the dude you want to hang out with right you wanna like who's really smart but also is not going to take himself too seriously but will work hard but but then like what's the point dude like what's the point if we're not going to try to enjoy this thing you know what I mean

49:44 yeah I mean I do look I think it's an interesting because our like 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 right Um, but I I guess I I can't

50:02 The cynics don't change the world though. Like they don't make change happen, do they? I think it's the the the the believers of crazy ideas that are willing to go do it.

50:12 The problem with that, I agree with you, but there are I do worry especially in this moment that like people have almost embraced that mentality too much in certain places um to a fault, right? So like for instance like there's a whole generation from my perspective of like 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 they're just like and I kind of get it right because I think one of the things that again timing is everything I I think I don't know how old you are probably a little bit younger than me but maybe not too much like we were born at like the most unbelievable moment in history right? Where like I lived right before the internet and I kind of vaguely remember it, but like we were like the internet native generation, right? Like the world

51:05 a dialup. Yeah. The world completely changed as we were coming up and like we're maybe actually a little bit like honestly I'm like 5 years too young actually because to like have hit it perfectly, right? Like you know like Peter Teal is probably exactly the right age, right? like I'm like a little young like at but like I caught it and and like but the generational thing is real and I think you look at that you're like oh my god in our generation in our kind of professional careers in the space like literally everything changed in a profound way and if you're born younger you just missed it right 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 but like so it's it's a tough one because you want

51:52 to be an optimist you want to be in it but I do think in a lot of places there's like people try to manufacture that where it's not to it 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 like they do it in noncredible ways which I actually think is like a detriment to everyone right? Like it's, you know, it's like, you know, SpaceX is an unbelievable company, right? Um, but like we're not that close to going to Mars, right? And like he knows it and it's like it's a there's like a cynicism to like overusing optimism as your, you know, tool for excitement, if that makes sense.

52:39 I know. Yeah, I get what you're saying. I I think more broadly I I just want to be around a group of people that have belief, that have joy, that have confidence, that are not necess 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 in people around them that we're going to go and enjoy this thing and get after it, have fun, not take ourselves too seriously. I want to be surrounded by that. I got one more.

53:14 I think the cultural it's a cultural thing, too. I mean, I think the moment we're in right now, like there's, you know, there's so much anger and fear and it's just

53:22 some of it is justified, honestly, but like I think big picture, it's like the wrong vibe for great things.

53:29 Agree. Agree. Oh, yeah. 100%. One more. 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/career advice you'd give to them?

53:45 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 let's be like, I know it looks good on paper. Like, yeah, let's talk about it. But my only real advice is write publicly. And I just really believe in this as you it's 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 time stamp it. And like I just think like it's an incredibly important calling card, right? 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, right?

54:26 That's really important. And then I guess the third factor where 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. 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 a public space, standing behind them. You're going to be wrong all the time. It's okay, right? Like I think and 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,

55:01 until you've been like deeply flamed on the internet by everyone over something, like you're going to fear that, right? If you put stuff out there, eventually you're going to say something that people are going to lose their [ __ ] about, right? And like I think even that is another form of just experiencing that's important, right? Like I I got to get I got to get blown up by the whole internet hating me at least once a year. I think there's so many things I could talk about when it comes to writing, but one 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 and you understand it. Then you publish it and it works as a way to sometimes draw people towards you, push

55:43 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 right. I'd love for them to publish too, but write, like, 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 a main reason I sign up for books and like sell a deal to a publisher because now I'm on the hook, right? And now you got I'm like, wait, I thought I knew what I was talking about.

56:16 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. Sam, this is awesome, dude. I really appreciate your time together. Is there anywhere you you'd like to send people to learn more about you online?

56:27 I don't know. I'm like at le most places. My website's wlesson.com. I don't know. Find me, but only if you're like if you I don't know. Or don't.

56:38 This is great, dude. I would love to continue our dialogue as we both progress. Maybe round record a round 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.

56:48 All right. Super fun, Ryan. Nice speaking with you. Talk. Thanks, man.

Questions about this episode

Who speaks in "From Facebook Executive to 2000x Crypto Returns | Venture Capital Masterclass with Sam Lessin"?

Ryan Hawk (Host), Sam Lessin (Guest).

What is "From Facebook Executive to 2000x Crypto Returns | Venture Capital Masterclass with Sam Lessin" about?

Sam Lessin shares insights from his journey as a former Facebook executive to achieving extraordinary returns in cryptocurrency investments. He emphasizes the importance of proactive thinking, public writing as a tool for clarity, and reflects on the profound influence of his father, who taught him valuable life lessons that shaped his career and perspective.

What is mentioned in this Ryan Hawk episode?

10 people, works and ideas are mentioned, including Secret Service Sam, Slow Ventures, Facebook, Salana, Bain, Drop.io. Each one on this page links to its own page with every episode that mentions it.

How long is "From Facebook Executive to 2000x Crypto Returns | Venture Capital Masterclass with Sam Lessin"?

The episode runs 57 min; the transcript is about 12,980 words in 120 timestamped sections.

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