Rafe Furst: Poker, entrepreneurship, venture capital, and overcoming personal crisis

And we're live for round two with Rafe Furst was on my podcast a couple of weeks ago for round one. We sort of scratched the surface in the the 30 minutes we were together and I thought Rafe was so interesting that I had to have him on on a round two and discuss more specifically his poker career and uh what happened at one of his poker company which I used back then Full Tilt as a poker player and Rafe's been through so much he's done so much

in his life that yeah I think one hour issue edition today should do us justice. So Rafe, another quick introduction about yourself and what you've been up to as of late. Yeah, thanks for having me on again Charles. It was it was fun last time and I agree we just scratched the surface. I hope we're going to get into some of those provocative questions.

Um those are some really good questions that that you set up before this call. But I'm happy of course to talk about you know, Full Tilt and anything else you want to talk about in the poker world. Um Yeah, so um you know, five time serial founder starting in the mid-90s web 1.0 days in Silicon Valley and um in you know, fintech and gaming tech and and and instructional media.

I also played on the professional poker circuit in the 2000s for about a decade going to the World Series of Poker ended up winning one of the World Series Poker events in 2006 Pot Limit Hold'em. Um I also done a ton of angel investing and even have pioneered a few new venture venture funds. Um and and investment models. And you know, these days so one of the things I did in the last year is I synthesized all that all that experience and and and hard-earned knowledge and wisdom from uh 30 years in in the trenches as a as a founder as a as an investor as a poker player into a book on the future of venture capital even though it's on the future of venture

capital, there's a lot in there for entrepreneurs and there's a lot in there for uh poker players or aspiring poker players because I use not not just the analogy of poker but the the the strategic thinking that comes from poker, I use that all the time in my investing and my um you know at my leadership and you know in uh as a founder as well strategic thinking.

Um so that's one aspect of what I'm up to these days. The other is that I um I coach uh and I um and I help founders uh with their capital raises in some instances. I love that. Let's start with poker itself. Are there very are are there um mindsets and the frameworks that we can apply to the business world? And if we can answer that question after but start with what does it take to be a poker champion?

What first brought you to it and are there any lessons that we can bring from the table to uh the business world? Hm. So so first talk about that what does it take to become a poker champion? Um okay. Uh it takes um a lot of uh a lot of time on the tables playing um and studying uh and by studying there's lots of ways that you can study these days that I didn't have available when I um was up and coming but you know first and foremost go on to AI and ask it to teach you how to play championship poker.

Most of the world's knowledge about that is actually in the AIs right now. And so then it's a matter of and you know, you can go online and you can get instructional videos and books and there are coaching coaching collectives for poker. Pretty much you name it. There are simulators and lots of tech that that are helpful. But the main thing is to be learning by actually playing.

Thousands and thousands and tens of thousands of and hundreds of thousands of hands and millions of hands ultimately. And you need luck. To to you know, to win as well. So in in poker what we say is over the long run your skill edge will lead to lead to riches. Or if you don't have a skill edge, if you're a losing player, it will lead to ruin. But the long run is a lot longer than you might think.

It's measured in in years, not in days or weeks. So a lot of players get frustrated by having you know, a losing week, a losing month, a losing six months. If you don't have the the bankroll or the stomach to withstand you know, a good 12 months or so a variance you're going to have a hard time making it in the long run as a professional. And to get started, is it just a love for money for the game?

Don't you need to have a little bit of an addictive personality? And then once you hit high stakes, is it about focus and maintaining your calm and still do the right calculations uh in unforeseen circumstances? Yeah, good questions. Um So, the first question, the uh the the nature or role of of addiction. Yeah, it is an addictive activity. It's fundamentally addictive.

Uh we know this. Um variable reinforcement. Um you know, it's because there's a lot of short-term luck or variance that it's addictive, but it's also it wouldn't be a fun game worth playing if the the most skilled players win every time. Right? Uh so, um it's just part of the nature of the game that it's going to cater to that uh addictive part of our our neuro psychology.

And I think the most successful players um they they find a way to temper their addictive tendencies and and not let that uh affect their decision-making. So, the goal in poker is to be making good strategic decisions under conditions of uncertainty and risk and addiction and emotions and high stakes, you name it, over and over and over and over again, knowing that you might just have like a 55% chance, 55% edge on any given hand that you're in, but in the long run that adds up.

In the short run, you know, approximately half the time you're going to lose. So, uh just being able to to manage that. Um and then I forget, what was the second part of the question? Yeah, um focus, concentration, maintaining your cool what when the stakes are very high. Which think it's so important? Yeah. So, uh uh the other aspect of it is is poker is is a developmental game in the sense of you first have to learn the basics.

Like, what are the rules of the game? And what hands beat what other hands? So, um it doesn't matter whether you're calm, cool, and collected if you're actually not playing by the rules or you don't know when you have a better hand than your opponent or not. So, it starts at the basics. And then from there, um once you're playing proper poker by the rules, the question becomes well, given that I I can't see my opponent's cards and I can't see what cards are coming, do I have a sense as to A, what am I what do I hold?

On average, is that going to be better than average? Is it worth playing? That's the first decision you make when you're dealt cards. Am I going to play this? Right? And if so, how am I going to play it? Um then there's another level, which is, okay, I have to then become have a theory. If I know where I stand I and just in general, on average, with a hand like king 10 suited.

I'm just going to make an example. Right? Some people might you know, think that's a a good hand um on average, and some people might think it's a bad hand on average. You have to have a lot of experience to know um which of those two things is true. However, once I have a sense of whether I have a a good hand in isolation, now I have to start making a mental model of each of my opponents and what they are likely to hold.

And I have to do a deductive process or inductive process that's similar to what artificial intelligence is doing where um based on more and more evidence throughout the course of play of a hand or the course of play of an evening, um I can narrow down a range of possible hands my opponent might have. Um and it goes on and on. Then then we're talking about learning things like um what are the pot odds?

What are the odds that uh well, the odds with more cards to come that uh a hand that's not a winning hand currently will become a winning hand. I might have a draw, four cards to a flush, and I need to make um you know, I need to uh hit uh another card in that suit in order to have a flush and have a winning hand. We do something called pot odds calculations.

Um and so that's a matter of how much is in the pot relative to how much I'm risking in order to to go for that. On top of that, it's you know, it maybe a psychological game. What be you know, uh you know, what do I think my opponent has, but more importantly or just as importantly, what does my opponent think I have? And what does my opponent think that I have or what do I think my opponent thinks that I have?

And so on. It just goes on and on. There's really you know, a a lot of different levels. Um but the key point about saying it's a developmental game is that you can't learn everything all at once. You have to go through the stages of novice to beginner to you know, advanced beginner to intermediate to advanced to expert to you know, virtuoso um etc.

So, um that was a long-winded answer, but um I I hope that you and others can maybe see the parallels between let's say entrepreneurship or investing and and poker, which are both very developmental as well. Yes, before we get to that, uh is there an AI that can beat pretty much all poker players right now. Yeah, I think I think it's safe to say that AI is it's kind of like in chess we've crossed that threshold.

Yeah, was it easier than chess and then go to create that AI? No, chess was solved in I think 1999. And then poker it took another let's say 10 years. Interesting and was it projecting an image and seeing the face of poker players to spot some possible bluffs or was it purely online where you couldn't see the player just the cards? Yeah, no it's just purely online where you where the human factor was taken out.

So what you're hinting at is that there's actually um there's actually two styles of of poker. One of which is called game theory optimal which doesn't require that you know anything about your opponents. uh you you just have um it's it's really it's purely a symbolic kind of mathematical computation. A game theory optimal computation of what the right move on average is and uh humans can't do game theory optimal.

um it requires a lot of a lot of calculation and number crunching. um but computers can and the key with game theory optimal is it's not going to necessarily be the best in all situations against humans. But it can't be exploited. Right? If I'm playing game theory optimal or if I'm a computer playing game theory optimal, I can't be beaten. It will be a zero-sum game in the end.

Or the person or the the computer playing game theory optimal will win because their opponent who's playing sub optimal will make game theoretic mistakes you know and and and lose the other style of play is what's called exploitative. So if if people have tendencies and they do and they have biases and they do and they're not playing perfect optimal poker then they are exploitable.

Okay, so I might pick up a tell I might you know see you blinking and think maybe you're not so certain of the strength of your hand you're a little nervous and so that's going to bias my mental model of your holdings and that might give me just enough edge to make a a decision that's that's goes different than game theory optimal. But I know it's enough that that that I will I will likely make a winning decision if I go with that exploitative strategy.

Now the problem is with exploitative strategy if I'm biasing towards you now I have a bias that you can exploit so you can be exploitative. So the top professionals these days they learn as much as they can as close as they can approximate to game theory optimal and they learn the human side of the equation getting tells and and whatnot picking up patterns that are very human patterns and they combine and they blend those two strategies based on the situation.

Makes sense? Yes and is it feasible career choice to become a poker player or is there is there just too much competition and the market isn't that interesting anymore? It's you know it's it's it's a twofold answer what's happened is the online game for obvious reasons has been taken over by a game theory optimal like, you know, AIs. It's hard to beat an AI or a human who's, you know, running a solver in the background.

They be they effectively become a So, the online game he really has been a, you know, a very declining market for the professional levels. You know, if there's no money at stake, the free the free games um you know, those are those are fine. Um but in the in in live poker, tournament poker has never been bigger. And and that's because by and large um like I said, humans can't play perfect and there's enough people who enjoy the game that there's still a potential edge for for top pros.

Interesting. I I would then to think that it's way more competitive and you need to invest a lot of time playing. You need to move yourself to big tournaments, sit at tables for hours. Isn't that like quite stressful / diminishing return career choice vs. being an entrepreneur or are both quite similar? So, it it's it's always been the case that poker is a hard way to make an easy living.

I didn't make that up, but it's it's perfectly true today as it was, you know, 40 years ago when I heard it first. Um and so it's gotten it's gotten you know, harder like the bar for a, you know, elite poker playing has absolutely risen. However the pool of people who are playing has also expanded. So, you have a, you know, a a bigger pool of of folks who are are still learning.

Yeah, noobs. And so um you know I don't think it's like it's not the it's not the right career choice for everybody. It's not the right career choice for most people. It wasn't even the right career choice for me. I I wasn't a full-time poker playing professional only. To me it becomes um it diminishes my quality of life if it's the only thing I'm doing.

So, I was always doing uh startups and and and investing and other activities um uh and work uh alongside of following the professional tour when I did. That said, I I I couldn't compete um in today's environment um because the bar has gotten so high. Yeah, it's like a hobby I would guess but you got quite good at it cuz you won a bracelet I believe um I think you need to pick your niche, right?

It's like Molly's game sort of and if you check Dan Bilzerian, I think I don't think he was super good at poker but I think he played against uh noob noobs and uh for very high stakes, right? It's like billionaires trying to play for a weekend. It's just like pocket money and betting a million here and Bilzerian is just better, right? I think that could be uh one niche.

Another insight here is that he has taken that career and has monetized on it. Uh went from this to influencer then to businessman. I'm not sure how he's doing uh business-wise but certainly very successful as a an influencer and maybe take some skills, right? I think it was uh Annie Duke's that uh you quoted at some point to me like uh her book which is uh is quite good.

It's about um betting and taking these skills and transferring them to business. Um I'm curious, is that how you see the world in in business? It's like, oh, I'm dealt this hand right now. These are my probabilities. Game theory, he might be bluffing. Is that how you you view the world and and business nowadays? So, I I used to view the world um primarily through that lens.

Um and I think that it's a very limited um and and and ultimately problematic world view, you know, we are right? Yeah, it's it's it's it's a very um it's strategic, but it doesn't bring in the whole of human experience and it and and it doesn't really honor the relationships. And it doesn't um foster cooperation and collaboration, which are essential.

I mean, that's one of the I mean, the fundamental the the fundamental difference in the game of business and the game of is that poker is a zero-sum game and business and life entrepreneurship is not. We are meant to collaborate and cooperate and that's how we win. We win more when we're when we're winning together. Um and so um another way of saying is it's a team game.

Um and you have to have skills that are entirely separate from the strategic mindset. Um uh and you have to have empathy and you have to cultivate your relationship skills and your leadership skills and um and so uh and you have to care. You have to care about the people that you're working with. You have to care about the people who you're making products and services for.

You have to care about your investors. You have to care about uh you know, the entire ecosystem, all the stakeholders um that might be impacted whether you know it or not. Um so, it's I think it's fundamentally important. So, to answer your question um in in you know as I've matured and and grown up and and seen how destructive it can be to to be uh simply strategic and and and cut off from uh human relationships and and my own humanity that uh I now take a a relationship first and a human first perspective.

However, it's great to have those strategic skills because it's um it's not either or, it's both and. In 2012, you were dealt the shittiest of hands, right? I think the SEC went after uh Full Tilt Poker and you were transparent enough to uh write a medium story that I read about that and that's uh that's pretty rare in the business world. Uh but it that must have been pretty stressful uh to to not say the least, right?

So, walk us through that experience. What happened there, and yeah, how did you deal with that psychologically? Do you feel that today you're stronger or you left some fetters behind with this experience? Yeah. Um well, the answer is both. I'm stronger and you know and I left some fetters behind. But I I um I'm very grateful uh at the end of the day.

I mean, I wouldn't you wouldn't go back and change it because it's it's made me a better person and and uh for sure. So, yeah, what happened was um we uh we actually it was the Department of Justice who uh who suit sued the company and then um it added on additional charges to its board of directors which included myself and the CEO and um a couple of others and and they charged that we were doing illegal gambling and fraud um and on the surface of it those charges actually we believe that those were false charges.

They just didn't like the fact that we were um, you know, playing online poker. We were serving online poker in the US and we had lots of legal opinions that said um, that what we were doing was legal. And so we were prepared to fight you know, that. Um, but what got uncovered uh, you know, in during the course of of that process is in fact there there was fraud unbeknownst to um, the the the non-executive board members myself included that um, a couple of the officers including the CEO were committing.

And um, and at that point I had already vouched for and I was pot committed to um, defending the the actions of the company. And that's when I got slapped personally with the uh, the lawsuit. Um, you know, what I I absolutely made so many mistakes leading up to that that I would um, do over again. Um, but by that time the die was cast and I was involved in a very very high stakes legal battle with the Department of Justice.

Um, and so they were suing me for more money than I had. They were uh, I had millions of we had millions of class action like class action lawsuits uh, against us. Uh, there were talks of criminal charges and uh, and the pressure was mounting. I was in-fighting with other friends who were co-founders. Um, my life was a mess. I was fighting with my wife.

My mental health was deteriorating. Um, and uh, after about eight months of that pressure cooker, I I snapped. I broke. I had a a psychotic episode. Which um Like uh it was a big reset. So, uh luckily I you know, I had the the love of a family and and and lots of friends. Um and I I recovered from that acute episode. But that was actually the beginning in 2012 of a journey of self-discovery, healing, um self-improvement, um all all areas that I never I never really was motivated to or thought I I needed to attend to.

Um because uh I had run good as they they say in poker. I'd hit a lot of green lights in life. Um on the surface of it everything was fine. I didn't realize underneath I wasn't um uh I wasn't really in touch with my humanity. I wasn't in touch with my emotions. I wasn't in touch with my how I was treating people or looking at people um as strategic pieces on a you know, in a poker game or a chessboard.

And that was having a a cumulative effect. And so, that's really the cause I would say of how I got to the crisis. But then it took you know, it's it's taken I'm I'm a work in progress like we all are. But it's you know, taken better part of 15 years or you know, uh to um to to be here where I am. That's uh sort of getting back on track or may not be even the the right word.

I did the 100K race I think uh like 8 months ago. Uh and right after that race I got like quite sick. And as a result I had to take uh syrups and so forth. And that brought panic attacks in the middle of the night, you know, and I was uh yeah, just like you uh Mr. Rational and all of that. Only recently have I understood that emotions are the basic OS of humans, even if you're like really rational, really strategic.

And I would never have expected to have like these things happen to me, just wake up in the middle of the night and think the world is ending, think everyone's going to die, you know? It's like, what the [ __ ] is my mind playing on me here? And just waiting 5 to 10 minutes and being my normal self again. So, that it can happen, um, to anyone. And yeah, it's it's it's the repression of that, right?

Like me trying to analyze that my 100K race, I had to take care of like two uh, individuals that were on the brink of death in the middle of the jungle, middle of nowhere. And I was like, what the [ __ ] Yeah, is this Are we going to make it? And And then I was sick. I was stuck on planes for like two weeks after that. I hate planes and sort of a bit claustrophobic.

So, my body just rebelled and be like, yeah, here you go. Panic attack one, panic attack two. Wow. And yeah, that's uh, I never expected that, right? But, uh, So, what did you I mean, can I ask? Um, so, what then How did you address what you were discovering and, you know, your your Sounds like you had some also some PTSD. Yes. Uh, some some part of it.

I I think, um, cuz yeah, we weren't stuck for basically 10 km without water, without any signs of civilization. What guy was having a heart attack or something. And then my uh, running partner, he he's literally been uh, running on uh, uh, calf muscle injury for like 80 km. So, yeah, it was pretty desperate, right? And that's why I do these things. It's that it brings you really to the bottom of the barrel.

And I I've been to the bottom of the of the barrel various times in my life. I actually enjoy bouncing back and and for example beginning of this year financially was not my best and in the last couple of weeks I've done really good for myself. So it's like oh good job. Why you went through that? But yeah, I think it's there's two ways that the brain um takes traumatic events.

If if you don't cross a threshold, it's just going to adapt and you're going to grow out of it, right? It's like no pain, no gain mentality. But if you cross a threshold, it becomes traumatic. It becomes like you're this monkey in the middle of the Savannah that's running for its life and that's like oh, the brain is is like never do that again. Uh because he thinks he he thought you would almost die, right?

So I didn't really have a process through it. I mean I'm a biohacker. I I do like all these um these cold plunges, saunas, these breathwork, Wim Hof breathwork. I walk every morning with my five dogs and wifey and have a good life here in Oaxaca. It's pretty nice. I go out and motocross almost every day. I run a lot and so forth, but I think that stack took me through it, but literally I had be very not very sick, but sick annoyingly sick for like a month or two after that.

I was cold every day. I when I would go run, I would cough, you know, which is like oh, I just lost my superpower, which is my human cardio. So part of my identity. And I think I also like um got a bit frustrated with that, right? Uh but I think I can leverage anger and get back on track. Did you also do that after that happened to you? Did Did you leverage that to to actually get back on track?

Um no. I I I not not for me. I mean I everybody's process is different. Um you You for me the thing that really was the the most helpful and transformative over time was to be in uh a pure pure community where we talk as um honestly and and we work through that emotional operating system that you talked about and we learned about you know, the the construction of the of the psyche of the ego um all of our defense mechanisms, core

wounds so um you know, from a you know, not only a like a neuro-logical but a psychological and the social rewards uh systems that are around us and um and and also the spiritual dimensions. Um and so for me, I quite like I I needed that um complete 360° container to help um you know, to help heal and and elevate to maybe another level of wisdom and stability and and and maturity.

Um Right, because you gave pretty much all that your ego wanted with all these years, right? You were very wealthy, very successful, very quick, right? Mhm. And that all broke from one day to the next. Also, you had your reputation, right? Because even though it wasn't uh valid, right? What happened to you that people will still jump on you, right? That we've seen lately with 11 acts.

I'm not sure if you heard about that one. Uh A16Z company uh sort of they were the CEO was a bit inventing claims. That's what the press claims, right? Yeah, I'm not too sure about it, but they had a shitstorm press and I'm pretty sure the company is not going to get back on track. And there's a deal that you may have heard of. This one's a bit silly.

It's on the corporate spying side of things like Rippling. They had Yeah, they had basically a spy in Rippling at as a company and now the deal CEO has escaped in Dubai. And yeah, his his reputation is completely destroyed. Deal is a multi-billion dollar company by the way. It's It's a very big company. Um so I think people you know, one day they might be your users.

But and your supporters, but the next as soon as the press turns against you, I think humans are quite quick to to turn against you just because we're social creatures. We're opportunists opportunistic creatures, right? So I must have sucked a lot to have like some of your customers support what was not even true, right? Yeah, for sure. Yeah, I wasn't aware of those instances you mentioned, but but yeah, I mean it's it's a a similar similar pattern, right?

As you as you you said. Yeah, and and it it it sucked. It sucked What what sucked more than anything for me is actually the loss of some very close friends. Very close friendships. And so, you know they very close if they left you in a moment of vulnerability? Well, I mean some some of those friends I got you know, we we've we've repaired and and got back together and and and a couple we didn't.

And you know, um nothing I can do about it. It always takes two to tango. Um you know, I'm I'm not I'm not beating myself up over it anymore. I've I've made my peace and I've I've done my best to apologize and make amends, but um you know, uh it's not you know, at some point you just have to let go and uh there's not not not no interest in reciprocation.

That's okay. But it But it sucks. It hurts. And don't you feel it's a normal cycle of like fast success sort of fast fall? Just that some CEOs and founders just manage it better PR-wise, right? Like that's all the why there's all these fancy PR firms. Don't you feel because yeah, me my my thinking behind that is just that most people that we see on on front of Forbes, for example, like very quick success, to me it's a curse, you know?

They're going to get hit. They're They're like the tallest blade grass in society will want to cut them. Don't you feel it's that way? I think there's some truth to that. Um you know, there is a dynamic um there and it's an age-old story of hubris and Icarus and flying too too close to the sun. Um I mean, I think what's coming up when when when you're talking um is uh it's really like at a fundamental at a fundamental level, like there are those of us who who take who who who strive to take radical responsibility for all the results in our in our in our environment and our life even if we don't see a direct causal connection.

Um and then there are those of us who um you know, to varying degrees uh look outside of themselves. And you know, I was certainly was in that latter camp. Um and over, you know, the past decade or so, I've I've come to appreciate more and more the stance that I, you know, each of us is responsible for everything that is happening um in our world and our environment.

So, when the [ __ ] is hitting the fan, if you take that stance, then it's like the first question becomes not woe is me or like who who can I blame or you know, whose fault is it, but like, oh, what did what did I what have I what am I doing what have I done, what you know, in the past, um how am I holding the situation or framing the situation in my mind, um that is actually causing or perpetuating the situation that I don't like.

Yeah, I like that. Um I'm pretty sure I'm going to get this shitstorm of bad press one day because I have big ambitions, right? Like as a founder, I know that I can carry a lot on my back. I can take a lot of weight, but I also need mechanisms to deal with that shitstorm, right? Whether it's a psychotherapist, uh psychotherapy GPT, uh whether it's a all the mechanisms that I named today, let's say that yeah, I hit that shitstorm uh soonish, in the next 5 to 10 years, what would uh what would the recommendations be?

Should I really uh disconnect work and personal to make sure that I recover from all that shitstorm that I'm eating on a daily basis? Uh what would be advised to to face such a a PR backlash? Well, I'm going to I'm going to answer it in a like a slightly different framing. And and like kind of two parts of it. One is I I what I what I would say is the best preparation is um is really just what is it that like if if I'm always acting in integrity with who I say I am to myself and others, what my values are, um if if I'm always uh attempting to see myself clearly and and act in integrity, even if it's hard, all right?

Or especially when it's hard. Um and I'm asking for feedback by people that I love and trust and who love and trust me because we can't see this stuff ourselves. That's the nature of the ego, the personality, and our psychology is that we we can't see our blind spots. So we need you know, we need community. We need people that we trust to really help us stay the path of who we who we seek to be.

Um and so what I would say is um that's how I would live my life. Um but it's also the best preparation because if I have nothing you know, that I am regretful or remorseful of um you know, I I can I can do what I can um and then stuff happens. Um uh then I feel like I have no I've no I've no there's no PR, there's no there's no need for spinning anything, there's no need for doing anything different um other than perhaps look, you know, you you've gotten a blow and you know, fortify yourself, right?

So yeah, definitely um when you get when you when you get the uh the feedback from the universe that hey, you know, you've been been hit by something, it's absolutely I think a great time to pause and slow down and reflect and ask questions of yourself, ask questions of of your loved ones. Hey, you know, am am I not seeing something? Why did this blindside me?

Right? Right. Yeah, it's a good angle. Um sometimes yet I also ponder about my ICP a lot like people that I serve right cuz the poker community like we discussed at the start a bunch of them are just uh quick distractible addicts and a lot of them and they they can turn easily on you, right? Uh you serve, I don't know, porn users or uh crypto audience, for example.

I think uh it's ICP can turn on you quickly. Nowadays, I tend to work with only CEOs, with founders, right? With people that are like me, that I want to Yeah, I don't know what's an ICP. Uh ideal customer persona. Okay. So, yeah, uh the the question is if uh and you seem to have pivoted to uh work with family offices and to with CEOs that you coach, with founders.

Um is that also good advice? Like choose what industry you work in and who you're targeting so that uh not only these people yeah, are are like you, they also pay you, obviously pay pay you well, but it's it's people that inspired you to be better. Um so that the PR backlash doesn't happen. For example, my clients, right? They're they're just like me.

They're they're friends, most of them and they would never talk [ __ ] against me. Uh we're we're intimate. Uh we're we're friends, right? So, is that also a a good lessons here to avoid the the [ __ ] show? 100%. I think you you said you know, another side of the same coin, which is and I'll and I'll play it back to you what I heard, which is um you want to be in business with, you want to be working with whether they're your your customers or you know, uh partners or affiliates or anybody you want to be doing business with you want to be doing business with people who are who share your same values.

They may not be identical to you, they might not be doing the same things and have all the same likes and dislikes, but the in terms of the core values and what you value like I think that's a a phenomenal filter or a phenomenal way to to define your niche is I want to be working with people who share my same values. Um and I think it's hard to go wrong.

Like it's a really that's a really excellent way of um of proceeding, I think. Right. And nowadays I do GTM for founders and sometimes I get quite frustrated that a lot of them are not understanding the the value of this, right? And it's like, "Oh, why do I need to chase them to convince them that they need GTM to fuel a business then they need to stop referring on referrals, for example." And some days not a lot of days cuz I like what I do in the end, but I'm like "Maybe I'd just be better investing in stuff and not talking to much humans and just making quietly

money on on my end and just sitting back and and relaxing and watching my investment grow." Which is a part of what you're doing, right? So, is is that a mindset or a conversation with yourself that you had before as an investor? It's just like you're you're just tired of uh serving this this market and you'd be better just investing, watching the money come in, and just living your life.

Um so here's how I would would would answer that, which is um it there's I I think one of the times that you know, the ways that we get tripped up, I know it's certainly true for me and and from what you said it sounds like it might be for for you too and I think it's very common, is when we feel like we we have to do certain things or we have to be working in a certain area or we have to be working with certain people or going after certain customers um in order to make a living, in order to make ends meet, in order to feel fulfilled financially uh or safe financially um that's uh a recipe for compromising on those ideals and those values that when we are um spending time

and and we are coming from our ideal self and we're working with others who share our values, we actually naturally become joyful and it doesn't feel like work or frustrating. It feels like just cultivating um those, you know, personal relationships and it's joyous and fun uh it doesn't feel like work or hard work. Um um and so for me, it's been a journey to actually walk the walk as, you know, as close to 100% of the time as I can.

I'm imperfect in that way, but that's my that's what I strive to do. Um and um what I what I know from, you know, uh watching other people, uh he who either do that or don't do that, and what I know from my own personal experience of doing that or not doing that or doing it less or more, is that the financial or or objective results that I'm seeking best follow when I'm in alignment with who I want to be

and I'm I'm following the guidance not of my head, but of my heart and my gut. Right, because, yeah, sometimes sometimes it's just like they don't understand I'm doing them a huge service now, but they don't listen, right? I guess it's also product market fit problem and and they need to adapt to the market and also becoming a pure investor, I think I just lose my humanity, right?

And just stand back behind a computer, which I can do, by the way, I'm very I'm introverted, very nerdy, can just like stand behind a computer and do do trades and code and not talk to anyone for days, but I think that uh sort of uh break something into me and uh forcing myself to grow is is also a a good challenge here. So, nowadays you're working with um family offices, you're you're a coach also.

Like, is is that fully uh fulfilling for you? And and what's your favorite part in there? Is the Is it talking about investments? Is it seeing your investments grow? Or is it uh coaching a founder that's struggling with one problem? Yeah. For me, uh what what feels best is is is helping other people um in areas where I have something to offer that, you know, it is is unique and that they they feel like they've gotten um a lot of value out of out of my work with them um and that I get paid commensurately to that.

Like, I'm not I'm not I'm not motivated anymore by hitting home runs or having um you know, putting a little bit of a value in and getting you know, a lot of value back. I I want the the equation the value equation to be really balanced. um and um and I really take the approach of like, is this somebody that I that I that I like and that I would want to have a beer with, right?

I want them in my personal life if I meet somebody new. Um and if if that's the case, then they're potential, you know, client or or or partner. Um I I think that's one of the mistakes that I you know, made consistently early on in you know, and even late into um you know, my former version of my career, which is I wasn't I wasn't very discerning um about who I would play with or do business with.

And that had a lot of problems, you know, not least of which was um you know, it didn't feed my soul. It was a drain. And then of course then you have all the all the other practical problems like, you know, you're not working with people who are in integrity. Uh, you know, they might uh, they might do a rug pull. They you know, they might uh, um, make life hard and frustrating um, you know, for for you.

So, I think for for many for many reasons um, I just like to come back to the simplest like, hey, do I like this person on a personal level? Um, do I think I can add value to you know, what they're doing that they can't you know, get elsewhere um, or they don't want to get elsewhere. They want to get it from me. And if so, then you know, are we a match for one another?

And great. Um, I'd love to explore that. And which founders do you get deep on emotional levels first before you can change rational business stuff? You know, so I I I like to work with um, people wherever they're at. You know, sometimes um, the the the biggest help that somebody needs is um, advice on on structuring structuring a deal. Um, sometimes it's interpersonal uh, challenges with a co-founder or you know, with their with significant other.

Um, sometimes it's um, you know, it goes down to uh, hidden you know, uh, unexpressed emotions in the emotional operating system. Um, and and sometimes it's just is like I don't know where it comes from, but it's like an intuitive hit, you know, that I get and I'm like, you know what? Here's something coming up. You know, I don't know if this is helpful, but I I think I I should share this with you for And so, I I like to work holistically and I don't I don't like to necessarily work out of a particular methodology.

I have a collection of tools that I've gathered over the many years of experience and then also, you know, being a a mentee or a coachee of um of of wise people. And so, uh I just show up um and I I attempt to be as present as possible and as responsive as possible to what what a client um is needing. I consider myself as an addict, a controlled one that discovered meditation and the the right path in life.

Uh do you think most of the best founders are addicts? Mhm. Well, I mean, I think that there's definitely a a correlation uh between like the like the risk-seeking uh the risk tolerance uh gene, if you want to call it. It's probably not as simple as a gene, but that personality type or that um yeah, the addiction uh complex. Um it's a psychological complex.

So, uh I think call it a disease. Yeah, I mean, you can call it what you want. Um I I think it's it's one of the ways that humans cope against stress. And some people are predisposed to addiction, some people are predisposed to um uh you know, ADHD, some people are predisposed to uh you know, autistic spectrum. It's uh some people are predisposed to certain personality disorders.

Um you know, um some people are predisposed to uh bipolar. Um it's it goes on and on, right? And so, it's just part of the human condition. And the question is I I think your question is like, okay, is there I mean, you asked if all founders are addicts. I'd say no. Um The best The best ones. The best ones? I would say definitely not. I would say the ones that uh tend to make a big splash, but, um, you know, uh, they're they're kind of like they're they're like they're like hot rising stars, but then they can be a like a hot flaming, you know, a crash as well.

Um, yeah, I mean, I think that that's I mean, part of part of the reason that their native intuitive, um, skills that would otherwise have them be, you know, a fantastic world-class CEO, um, uh, gets side, you know, it gets side-swiped by whether it's their addiction or, you know, their, uh, what do you call it, predisposition to uh, other, you know, mental health challenges.

Uh, it's a very pressure-filled environment. And so, uh, it definitely stretches you, kind of the same way that 100-mile races stretch you. Um, and so, you're going to you're going to be you brought to your breaking point. Um, and I think that I guess for me, the way I look at it is you can either attribute it as, uh, a spiritual journey and and take that stress and the lessons that you learn from it to grow, or you can deny that there's something in it for for you to learn and take on board and make changes and got to keep reality at bay, and

then you'll find out what happens when you, uh, keep the reality distortion field on for too long. Um, Yeah, that that Elon, um, reality field of distortion, and Elon's a total addict, by the way. It's like, uh, video games or tweets or Yeah. And some Bankman-Fried's, uh, but certainly that. So, it's fast rising, fast falling. Still like puzzled as for why Elon could keep that stress level for for that long.

He doesn't seem to have any mechanism, right? Maybe the sadistic nature like sort of completely erases his blind zones, but it also seems that had an effect on him, right? If you've seen as of late, you see his uh his brain is not firing on all cylinders. The rational side of things seems to not making a lot of sense in a lot of his uh incoherent tweets.

So, yeah, it's certainly interesting. Um I think um I think that's worth just double clicking on that because you're right. I mean, you're you're you're hitting on the pattern that that can happen with people. I think the the the the the other factor is um having having that that village or that community of care around you that you that you respect and listen to.

And what happens I think sometimes with certain the people you know, get to positions of power um and wealth um is they kind of reach escape velocity. They're no longer listening to those um caring sane voices around them telling them, "You know what? You You went too far." And they start to believe their own stuff and they become surrounded by and I can say this from personal experience.

You can become surrounded by people who are sycophantic. They're not in it because they care about you. They're not going to tell you the hard truths. They're going to be in it just to kind of sit at the altar of the king and you know, get the goodies. Um and so, that's a very dangerous place to be in because you can go from a place where you are in a healthy spot very you know, pretty quickly without realizing it to a place where it's it's just you and your reality distortion field in a feedback loop by itself.

Um and then people around you who are reinforcing that reality distortion field and it's I it's all too common. You see it everywhere. Very deep and I would invite people last but not least to just read stories on your website. Lost Boys Return is quite great and you wrote another one about what happened uh uh with the uh Justice Department there. It's so good.

It's it's well written. It's fully transparent. Other than that, Raif, where can people find out more about you? Yeah, I mean the best place is my website. It's just my name uh r a f e f u r s t raifirst.com and on there also um you know, I I have my my book, my first book. I'm pretty proud of it. It's called The Future of Venture Capital. Um how to win the the VC game and make positive impact.

Um um and uh it was uh and so I put a lot of the stories in there. But you know, the most raw stuff that authentic stuff that we're talking about uh I reserve for the website um and the book is but the book has a lot of poker stuff in it and it has some good stories and lessons learned for entrepreneurs, for investors um and whatnot. So uh yeah, go to my website and it's all it's all there from there.

This is Raif First and Charles Mizrahi.