The Exchanges

Q Favourite blog or newsletter? We said about, kind of, Fred and Brad there. Who are your must-reads?

A My must-reads every day are, you know, a few. So, Abnormal Returns, I read just for, he says, Great Link Festo and what's happening on the financial web. For Pulse of the Markets, obviously, I live on stock twits. But my favourite I think blogs that, like, I go back to because he summarizes it the way I think is Josh Brown, who is a reform broker, who is funny and just mean, but does it in a funny way, and, you know, has this, uh, weird look on the financial world. And elsewhere, I still read Fred's blog. It doesn't always have what he's doing, but you can get tapped into the zen of angel and media investing. And I like tech memes still as a daily habit, and I've been using Nuzzle.

AI assessment note: “My must-reads every day are, you know, a few.”

Q Love nozzle. Absolutely. Yeah. And then we had Jonathan Abrahams on the show. Uh, you met, you mentioned obviously again, Fred and Brad there, when you started the journey, you said on twist, you didn't know anyone at all really. And you were starting out as an unknown. How did you network your way into the, into the height of VC?

A I think you'd say, yeah, I, I, it was 2005. I searched term sheet. It's Tom, my partner and I, uh, had found this golf deal. In Phoenix called golf now.com. Uh, it was at the time it was six Oh two golf. We didn't know how to do a term sheet. I searched term sheet in Google. Uh, I think it was Brad's series on term sheets. I copy pasted it. I was like, what? They're not charging for this. And I started leaving thank yous on their blogs. And I was joking with them how stupid they were for giving this stuff away for free. And they were like, well, that's what we do. And then, you know, we just give it away. It's karma. And I started my own blog from that started writing. They started linking, uh, So there was no, like, hey, I'm looking for anything. I was just, like, unbelievably grateful that I had found these two knuckleheads and their, and their blog rolls, and I couldn't believe, it's kind of one of those things, like the club. If the club wants me in it, that club can't be a good club, but, you know, back in those days, Fred and Brad were blogging and giving it away, and all you had to do was be polite and socially normal, and, like, understand the, the behavior of Of, of being nice. And through that, I got a meeting with Fred, uh, to pitch my, my idea wall strip, and Fred and Brad, Mark Pincus, as I said, invested, and the rest is history. So it was more like, you know, stu…

AI assessment note: “I started leaving thank yous on their blogs... started writing. They started linking”

Q Love nozzle. Absolutely. Yeah. And then we had Jonathan Abrahams on the show. Uh, you met, you mentioned obviously again, Fred and Brad there, when you started the journey, you said on twist, you didn't know anyone at all really. And you were starting out as an unknown. How did you network your way into the, into the height of VC?

A I think you'd say, yeah, I, I, it was 2005. I searched term sheet. It's Tom, my partner and I, uh, had found this golf deal. In Phoenix called golf now.com. Uh, it was at the time it was six Oh two golf. We didn't know how to do a term sheet. I searched term sheet in Google. Uh, I think it was Brad's series on term sheets. I copy pasted it. I was like, what? They're not charging for this. And I started leaving thank yous on their blogs. And I was joking with them how stupid they were for giving this stuff away for free. And they were like, well, that's what we do. And then, you know, we just give it away. It's karma. And I started my own blog from that started writing. They started linking, uh, So there was no, like, hey, I'm looking for anything. I was just, like, unbelievably grateful that I had found these two knuckleheads and their, and their blog rolls, and I couldn't believe, it's kind of one of those things, like the club. If the club wants me in it, that club can't be a good club, but, you know, back in those days, Fred and Brad were blogging and giving it away, and all you had to do was be polite and socially normal, and, like, understand the, the behavior of Of, of being nice. And through that, I got a meeting with Fred, uh, to pitch my, my idea wall strip, and Fred and Brad, Mark Pincus, as I said, invested, and the rest is history. So it was more like, you know, stu…

AI assessment note: “through that, I got a meeting with Fred, uh, to pitch my, my idea”

Q money to work there, and in the early days of your angel investments and putting that money to work, Navar Ravikam once told me that Uh, your first 30 angel investments will go to zero. Do you agree with this kind of short-fire thesis? Uh, and how did it play out for you in terms of your kind of investment decision-making and pattern recognition as you developed as an angel?

A Well, I mean, I know Naval well. We were actually, Tom and I, my partner, were one of the first checks into AngelList in 2010. And so, what attracted us to Naval, for example, is, and the product was, He was going to, uh, in our opinion, vanguardize, and Naval back this up. You know, we believed he was going to create an asset class around early stage investing and eventually do what, uh, S&P and Vanguard is doing to hedge funds to this whole industry. Everybody should have access. So Naval's, you know, talking his own book when he says you're going to lose on your first 30 investments. Luckily for me, I probably lost on my first four back in 99 when everybody lost money in the bubble. But when I really started investing after I sold Wallstrip, Uh, I caught a great crop of entrepreneurs in 2006, 2007, 2008, and I would say 50% of the companies worked out fantastically. So, uh, it's not because I'm smart, or it's not because of any one particular thing. I caught a great time, uh, at the era that Twitter and Facebook were taking off, and really put a lot of money to work, and it worked out fantastically. What Naval's doing with AngelList is saying, listen, this is hard. You have to catch Multiple crops or seasons or flavors of the market as technology changes so rapidly. So the best thing to do is invest in 80 to a hundred startups. Where startups versus the stock market differ i…

AI assessment note: “Naval's, you know, talking his own book when he says you're going to lose”

Q Do you think the knowledge of the public markets is sufficient enough in this ecosystem? In the startup ecosystem, there seems to be a complete lack of public market awareness. Do you think that's a fair enough assumption, and do you think it's a necessary knowledge to have?

A I think it's an edge. Is it necessary? I mean, uh, in 99, 2000, I'm sure Fred Wilson and Brad Feld and a lot of the VCs wish they understood the stock markets because they would have sold, because they could have sold. Instead, they wrote everything to zero in 2001. They educated themselves the hard way with real dollars. So for, for people to get into this business and have never lost money in the stock market, bring them on. I say, I want everybody to To not have experience in the stock market, because that gives me an edge at social leverage, right? Like, people need to lose money to really understand how the markets work, and you can lose that money in a private deal or in the public markets, but until you're cut and bleed and see how co-investors behave with you and how the entrepreneur feels, I don't think you have any understanding of what can go wrong in a down cycle. So, I think the stock market is the easiest way. The, the media would make you think it's taboo in the hardest way, but oh my god, the stock market is Basically free with an app like Robin Hood and using StockTwits, which we created. You can learn the language in six months to a year. You can put money to work, zero commission, and whether it's one share or a hundred shares, learn how you behave when you make or lose money, yet everybody's piling into vanilla S&P funds because that's what the media is sayi…

AI assessment note: “I think it's an edge. Is it necessary? I mean, uh, in 99”

Q Can I ask a potentially conflicting question here to you, and it's, is it possible to be a trend follower and to be, uh, conviction driven?

A Yeah, of course. Like, so trend following to me just means you see certain patterns, and you know historically from seeing patterns hundreds and hundreds of times with the Curve looks on growth, et cetera, et cetera, and you go, wait a minute, this is a pattern that's repeating. I'm in. The easiest way to do this in the stock market, because there's thousands of stocks, uh, human behavior all plays out the same way. There's obviously earnings and growth matter, but on top of earnings and growth are people's behavior, which is, they behave the same way, greed and fear. So, uh, trend phone is just a simple way to ride along greed and fear, uh, with some rules on top. In the private market, where you can't change your mind the next day and sell something, trend following is much different. It's definitely a riskier strategy than in the stock market, and so in the private markets, you know, I like to follow smart people, but I also like to have conviction about what I know and have my, you know, place in the world. I don't want to just, if everybody's doing a chat app, I don't want to trend follow and just do a chat app, whereas in the stock market, if chat ads are going up, If there's eight stalks of chat apps going up, I may be able to ride that trend knowing that I can change my mind the next day. But in private markets, you can't do that. That's, again, that connection to priva…

AI assessment note: “Yeah, of course. Like, so trend following to me just means you see certain patterns”

Q Favourite blog or newsletter? We said about, kind of, Fred and Brad there. Who are your must-reads?

A My must-reads every day are, you know, a few. So, Abnormal Returns, I read just for, he says, Great Link Festo and what's happening on the financial web. For Pulse of the Markets, obviously, I live on stock twits. But my favourite I think blogs that, like, I go back to because he summarizes it the way I think is Josh Brown, who is a reform broker, who is funny and just mean, but does it in a funny way, and, you know, has this, uh, weird look on the financial world. And elsewhere, I still read Fred's blog. It doesn't always have what he's doing, but you can get tapped into the zen of angel and media investing. And I like tech memes still as a daily habit, and I've been using Nuzzle.

AI assessment note: “My must-reads every day are, you know, a few. So, Abnormal Returns”

Q Do you think the knowledge of the public markets is sufficient enough in this ecosystem? In the startup ecosystem, there seems to be a complete lack of public market awareness. Do you think that's a fair enough assumption, and do you think it's a necessary knowledge to have?

A I think it's an edge. Is it necessary? I mean, uh, in 99, 2000, I'm sure Fred Wilson and Brad Feld and a lot of the VCs wish they understood the stock markets because they would have sold, because they could have sold. Instead, they wrote everything to zero in 2001. They educated themselves the hard way with real dollars. So for, for people to get into this business and have never lost money in the stock market, bring them on. I say, I want everybody to To not have experience in the stock market, because that gives me an edge at social leverage, right? Like, people need to lose money to really understand how the markets work, and you can lose that money in a private deal or in the public markets, but until you're cut and bleed and see how co-investors behave with you and how the entrepreneur feels, I don't think you have any understanding of what can go wrong in a down cycle. So, I think the stock market is the easiest way. The, the media would make you think it's taboo in the hardest way, but oh my god, the stock market is Basically free with an app like Robin Hood and using StockTwits, which we created. You can learn the language in six months to a year. You can put money to work, zero commission, and whether it's one share or a hundred shares, learn how you behave when you make or lose money, yet everybody's piling into vanilla S&P funds because that's what the media is sayi…

AI assessment note: “I think it's an edge. Is it necessary?”

Q Fantastic. And what a story. Uh, you've also said before, if fundraising is a skill. So if fundraising is a skill, what's core to this?

A Well, there's two ways to fundraise. There's to lie, come with a blank white paper and say, We're going to fill this paper in. That seems to work sometimes. The more domain experience you have and the better story you can weave and the better your network, the higher likely you are to, I guess, get an investment. The harder way is to actually know what you want to do because as soon as you know what you want to do, it's easy to rip it apart. So the skill comes in knowing how to pitch to the investors that you're in front of and, you know, having the right pitch at the right time matters because I would say 80% of companies, if they're not pivoting, they're completely Changing their business model, or their focus, or new products come out of the failed products that happen. So, it's hard for me to look entrepreneurs straight in the eye and take everything they say with a grain of salt. The good ones know they're going to be bobbing and weaving, and you know, you're trying to find entrepreneurs that aren't going to quit. So, the skill of myself knowing all that, going out to raise money, is you're trying to exude confidence. Like, you know, you've got to let them know that first, you're not going to steal the money. Second, you know what you're doing. Third, you have this big vision. Fourth, This vision, uh, has a lot of different varialities to it or variables to it that we'd be…

AI assessment note: “the skill of myself knowing all that, going out to raise money, is you're trying to exude confidence.”

Q In terms of kind of getting that edge and being that great investor, um, both Mark Andreessen and Satya Patel at Homebrew said before that having strong opinions loosely held is a characteristic of great Uh, great investors. Is that something you agree with, uh, particularly coming from, drawing from your experience as a hedge fund manager? Is that a, is that a characteristic of a great investor for you?

A Um, it's not so much a characteristic. It's just the truth. You know, I think you can, there's many different ways to make money. I think if you want to do this for decades, which is what I've been doing and what I plan to do, and hopefully my kids get the same excitement and my partner's kids and their cousins, whatever, whoever wants to do this, you really have to live And believe in this, uh, cycle. I got lucky because with the stock market, it really taught you those things. You know, I grew up trading in an Arab Jim Cramer. He changes mine every five minutes. You couldn't keep track of it. The point was that's really what matters. You know, you have to have conviction, but at the same time, you sometimes have to just, whoa, you can't drive everything off a cliff. So at the same time, you have to be willing to understand that things change, the playing field changes, uh, things happen to CEOs, uh, family issues, uh, Different kinds of things happen, and you have to have strong opinions to get that first check in, and to help those entrepreneurs, but then at the same time, you can't continue to fund bad ideas, so, or things that aren't getting traction, or entrepreneurs that just don't have it. So you get these signals, and you can go from strong opinion, but I think sometimes you just have to have loosely held, and that, that plays out in, do not average into your losers. I…

AI assessment note: “It's not so much a characteristic. It's just the truth.”

Q In terms of kind of getting that edge and being that great investor, um, both Mark Andreessen and Satya Patel at Homebrew said before that having strong opinions loosely held is a characteristic of great Uh, great investors. Is that something you agree with, uh, particularly coming from, drawing from your experience as a hedge fund manager? Is that a, is that a characteristic of a great investor for you?

A Um, it's not so much a characteristic. It's just the truth. You know, I think you can, there's many different ways to make money. I think if you want to do this for decades, which is what I've been doing and what I plan to do, and hopefully my kids get the same excitement and my partner's kids and their cousins, whatever, whoever wants to do this, you really have to live And believe in this, uh, cycle. I got lucky because with the stock market, it really taught you those things. You know, I grew up trading in an Arab Jim Cramer. He changes mine every five minutes. You couldn't keep track of it. The point was that's really what matters. You know, you have to have conviction, but at the same time, you sometimes have to just, whoa, you can't drive everything off a cliff. So at the same time, you have to be willing to understand that things change, the playing field changes, uh, things happen to CEOs, uh, family issues, uh, Different kinds of things happen, and you have to have strong opinions to get that first check in, and to help those entrepreneurs, but then at the same time, you can't continue to fund bad ideas, so, or things that aren't getting traction, or entrepreneurs that just don't have it. So you get these signals, and you can go from strong opinion, but I think sometimes you just have to have loosely held, and that, that plays out in, do not average into your losers. I…

AI assessment note: “it's not so much a characteristic. It's just the truth.”

Q Can I ask a potentially conflicting question here to you, and it's, is it possible to be a trend follower and to be, uh, conviction driven?

A Yeah, of course. Like, so trend following to me just means you see certain patterns, and you know historically from seeing patterns hundreds and hundreds of times with the Curve looks on growth, et cetera, et cetera, and you go, wait a minute, this is a pattern that's repeating. I'm in. The easiest way to do this in the stock market, because there's thousands of stocks, uh, human behavior all plays out the same way. There's obviously earnings and growth matter, but on top of earnings and growth are people's behavior, which is, they behave the same way, greed and fear. So, uh, trend phone is just a simple way to ride along greed and fear, uh, with some rules on top. In the private market, where you can't change your mind the next day and sell something, trend following is much different. It's definitely a riskier strategy than in the stock market, and so in the private markets, you know, I like to follow smart people, but I also like to have conviction about what I know and have my, you know, place in the world. I don't want to just, if everybody's doing a chat app, I don't want to trend follow and just do a chat app, whereas in the stock market, if chat ads are going up, If there's eight stalks of chat apps going up, I may be able to ride that trend knowing that I can change my mind the next day. But in private markets, you can't do that. That's, again, that connection to priva…

AI assessment note: “Yeah, of course. Like, so trend following to me just means”

Q Do you apply that learning in terms of valuation, in terms of being on a rocket ship? It doesn't matter what price you get in. Do you apply that to your thought process today, or does valuation still play a pretty pivotal role in your investment decision making?

A Culturally, I'm conservative. I'm Canadian. The way I think about Money is pyramiding, so, you know, you have to have money to make money, so I'm much more conservative than a typical VC, and so the lesson from Fred there was, hey, if you like the CEO, and you like the opportunity, and you like the market, and every single thing about this says yes, and the only reason you say no in a private, this is private stuff, not public check, and the only reason you say no is the price, well, you should probably hold your nose and write the check. And so, you know, that's what makes Fred, Fred, or is that they're able, you know, to pass on that wisdom. And we, we laugh about it. We've talked about it. I've interviewed Fred and I've asked for, you know, what he would have done. And he would have done the same thing as me as a 25 K to a hundred K angel investor. You know, the difference between, between paying two pre and 20 pre can be massive, especially if you're not going to have the capital to follow on. I passed for the right reasons, but I shouldn't have passed.

AI assessment note: “I passed for the right reasons, but I shouldn't have passed.”

Q Do you apply that learning in terms of valuation, in terms of being on a rocket ship? It doesn't matter what price you get in. Do you apply that to your thought process today, or does valuation still play a pretty pivotal role in your investment decision making?

A Culturally, I'm conservative. I'm Canadian. The way I think about Money is pyramiding, so, you know, you have to have money to make money, so I'm much more conservative than a typical VC, and so the lesson from Fred there was, hey, if you like the CEO, and you like the opportunity, and you like the market, and every single thing about this says yes, and the only reason you say no in a private, this is private stuff, not public check, and the only reason you say no is the price, well, you should probably hold your nose and write the check. And so, you know, that's what makes Fred, Fred, or is that they're able, you know, to pass on that wisdom. And we, we laugh about it. We've talked about it. I've interviewed Fred and I've asked for, you know, what he would have done. And he would have done the same thing as me as a 25 K to a hundred K angel investor. You know, the difference between, between paying two pre and 20 pre can be massive, especially if you're not going to have the capital to follow on. I passed for the right reasons, but I shouldn't have passed.

AI assessment note: “I'm much more conservative than a typical VC, and so the lesson from Fred”

Q money to work there, and in the early days of your angel investments and putting that money to work, Navar Ravikam once told me that Uh, your first 30 angel investments will go to zero. Do you agree with this kind of short-fire thesis? Uh, and how did it play out for you in terms of your kind of investment decision-making and pattern recognition as you developed as an angel?

A Well, I mean, I know Naval well. We were actually, Tom and I, my partner, were one of the first checks into AngelList in 2010. And so, what attracted us to Naval, for example, is, and the product was, He was going to, uh, in our opinion, vanguardize, and Naval back this up. You know, we believed he was going to create an asset class around early stage investing and eventually do what, uh, S&P and Vanguard is doing to hedge funds to this whole industry. Everybody should have access. So Naval's, you know, talking his own book when he says you're going to lose on your first 30 investments. Luckily for me, I probably lost on my first four back in 99 when everybody lost money in the bubble. But when I really started investing after I sold Wallstrip, Uh, I caught a great crop of entrepreneurs in 2006, 2007, 2008, and I would say 50% of the companies worked out fantastically. So, uh, it's not because I'm smart, or it's not because of any one particular thing. I caught a great time, uh, at the era that Twitter and Facebook were taking off, and really put a lot of money to work, and it worked out fantastically. What Naval's doing with AngelList is saying, listen, this is hard. You have to catch Multiple crops or seasons or flavors of the market as technology changes so rapidly. So the best thing to do is invest in 80 to a hundred startups. Where startups versus the stock market differ i…

AI assessment note: “Luckily for me, I probably lost on my first four back in 99”

Q to your long-term, 20, thirty-year thinking with regards to raising institutional money. What do you make of the plethora of seed funds that we've seen from, from, let's say, very young and very inexperienced first-time fund managers? How do you think about that, and how do you relate to that when people say that is the sign of a funding bubble and too much liquidity and capital in the market?

A Well, I have this saying where the markets are rigged. If you go into your business knowing that everybody's out to get you, like if you would just assume everybody's out to get you, waking up every day is a lot easier. But if you wake up every day looking to just fight the system and be mad that somebody raised this fund, and somebody raised that fund, and the Fed this, and Wells Fargo's stealing from us, I mean, it's fun. I joke about it all day, but I don't, it's serenity now stuff. I get it off my chest, and I move on with an optimistic deal of life. You can't worry about what everybody else is doing. This goes back to that strong convictions loosely held. You have to believe you're going to be doing this, and you have to constantly be selling, to constantly be networking, you have to constantly, you know, be on the ground doing your thing, and including that is writing checks, you know, it's good and bad cycles. So, consistency matters. To be consistent, you got to hop out of bed every day, and you can't be worrying about what other people are doing. You have to have that conviction, and this is what, this is what the world's going to look like in 30 years, and you know, if I continue to do this thing every day, It doesn't really matter what's happening. Is it a bubble today or a bubble tomorrow? I mean, if you invest for a ten-year fund, high likelihood you're going to ha…

AI assessment note: “You can't worry about what everybody else is doing. This goes back to”

Q kind of going to zero or going, going sky high where, you know, with the fund returner. In terms of those fund returners, you obviously need to get the trends right. So, I'm intrigued to learn how you approach the trend following process, what you specifically look for in those trends. Is it co-investors? Is it Specific market dynamics, and how you then apply the capital from those trend followings?

A Well, I mean, my job is to read all day. I obviously have a passion around finance, so I feel I have some domain experience. You know, when I was a kid, we played the game Risk, and in the game Risk, very simple, flat board game, but the idea was to take over the world. And if you took over the world, the easiest place to do that was from a corner of the world like Chile or Brazil or Western Australia. And that's the way, uh, angel investing works too. You're not going to start out in Europe with a thousand borders and take over the world. In the angel investing world, I like to keep it simple. First rule of thumb, follow smart people, right? Because, uh, just like in sports, in the Tour de France, if you can keep up with the smart people, then you can just draft behind them. So when I discovered Brad's blog, Brad Feld, Fred Wilson, when I discovered their blog rules back in Fast follow some of the smartest people sharing in real time or on their blogs what kind of stuff interested them. It didn't get too, I try not to complicate it after that, and so I followed along on the trends that those guys were doing. I merced myself in the ecosystem. I started finding great entrepreneurs. The rest is kind of history, and I don't think, listen, you have to put your own money to work. You have to take incredible risk. You sometimes get a whole batch just left Investing in wine, sometimes…

AI assessment note: “First rule of thumb, follow smart people... Fast follow some of the smartest people”

Q Fantastic. And what a story. Uh, you've also said before, if fundraising is a skill. So if fundraising is a skill, what's core to this?

A Well, there's two ways to fundraise. There's to lie, come with a blank white paper and say, We're going to fill this paper in. That seems to work sometimes. The more domain experience you have and the better story you can weave and the better your network, the higher likely you are to, I guess, get an investment. The harder way is to actually know what you want to do because as soon as you know what you want to do, it's easy to rip it apart. So the skill comes in knowing how to pitch to the investors that you're in front of and, you know, having the right pitch at the right time matters because I would say 80% of companies, if they're not pivoting, they're completely Changing their business model, or their focus, or new products come out of the failed products that happen. So, it's hard for me to look entrepreneurs straight in the eye and take everything they say with a grain of salt. The good ones know they're going to be bobbing and weaving, and you know, you're trying to find entrepreneurs that aren't going to quit. So, the skill of myself knowing all that, going out to raise money, is you're trying to exude confidence. Like, you know, you've got to let them know that first, you're not going to steal the money. Second, you know what you're doing. Third, you have this big vision. Fourth, This vision, uh, has a lot of different varialities to it or variables to it that we'd be…

AI assessment note: “So the skill comes in knowing how to pitch to the investors that you're in front of”

Q kind of going to zero or going, going sky high where, you know, with the fund returner. In terms of those fund returners, you obviously need to get the trends right. So, I'm intrigued to learn how you approach the trend following process, what you specifically look for in those trends. Is it co-investors? Is it Specific market dynamics, and how you then apply the capital from those trend followings?

A Well, I mean, my job is to read all day. I obviously have a passion around finance, so I feel I have some domain experience. You know, when I was a kid, we played the game Risk, and in the game Risk, very simple, flat board game, but the idea was to take over the world. And if you took over the world, the easiest place to do that was from a corner of the world like Chile or Brazil or Western Australia. And that's the way, uh, angel investing works too. You're not going to start out in Europe with a thousand borders and take over the world. In the angel investing world, I like to keep it simple. First rule of thumb, follow smart people, right? Because, uh, just like in sports, in the Tour de France, if you can keep up with the smart people, then you can just draft behind them. So when I discovered Brad's blog, Brad Feld, Fred Wilson, when I discovered their blog rules back in Fast follow some of the smartest people sharing in real time or on their blogs what kind of stuff interested them. It didn't get too, I try not to complicate it after that, and so I followed along on the trends that those guys were doing. I merced myself in the ecosystem. I started finding great entrepreneurs. The rest is kind of history, and I don't think, listen, you have to put your own money to work. You have to take incredible risk. You sometimes get a whole batch just left Investing in wine, sometimes…

AI assessment note: “First rule of thumb, follow smart people, right?”

Q in an interview three years ago with Jason Calacanis, and you said that hedge funds and mutual funds were breaking because it's become about simply gathering mass assets. I'd love to hear with your interest in angel investing in startups whether you think this Can be attributed to VC today with, with the mammoth funds of the likes of Andreessen and General Catalyst and Kleiner. Do you think that's possible?

A Yeah, I mean, the incentive became, you can see it happening in hedge funds, uh, 20 years ago when I started my hedge fund, it really was like, oh my god, if I'm starting a hedge fund, that must be the top. But I, I'm a trend follower, so I always felt like I'm not the last guy in the pool. I'm definitely not the first guy ever to jump in a trend, but I'm not the last person to jump in a pool. So I had 17 great years doing it i think four or five years ago when i started writing about how you know money is just being i would call it vanillized vanguard s&p makes sense the system's working money's flowing in to these vanguard simple mechanical fortune 500 s&p 500 etfs and so it's destroying creativity and it's also you're going to start to see some massive fallout i can't predict when but you're starting to see cracks companies misbehaving again because you know it's okay for wells Wells Fargo as part of the S&P 500 to misbehave because they wake up the next day and money flows into Vanguard and money flows into Wells Fargo. That's what happens when you have this trend away from choice to, oh my God, I just don't want to pay fees and I just don't even want to understand what to do with my money. The switch to angel for me kind of happened around the same time where I got bored with the idea that trying to beat the market. There was so much alpha to be had by combing the streets …

AI assessment note: “The switch to angel for me kind of happened around the same time where I”

Q in an interview three years ago with Jason Calacanis, and you said that hedge funds and mutual funds were breaking because it's become about simply gathering mass assets. I'd love to hear with your interest in angel investing in startups whether you think this Can be attributed to VC today with, with the mammoth funds of the likes of Andreessen and General Catalyst and Kleiner. Do you think that's possible?

A Yeah, I mean, the incentive became, you can see it happening in hedge funds, uh, 20 years ago when I started my hedge fund, it really was like, oh my god, if I'm starting a hedge fund, that must be the top. But I, I'm a trend follower, so I always felt like I'm not the last guy in the pool. I'm definitely not the first guy ever to jump in a trend, but I'm not the last person to jump in a pool. So I had 17 great years doing it i think four or five years ago when i started writing about how you know money is just being i would call it vanillized vanguard s&p makes sense the system's working money's flowing in to these vanguard simple mechanical fortune 500 s&p 500 etfs and so it's destroying creativity and it's also you're going to start to see some massive fallout i can't predict when but you're starting to see cracks companies misbehaving again because you know it's okay for wells Wells Fargo as part of the S&P 500 to misbehave because they wake up the next day and money flows into Vanguard and money flows into Wells Fargo. That's what happens when you have this trend away from choice to, oh my God, I just don't want to pay fees and I just don't even want to understand what to do with my money. The switch to angel for me kind of happened around the same time where I got bored with the idea that trying to beat the market. There was so much alpha to be had by combing the streets …

AI assessment note: “The switch to angel for me kind of happened around the same time”

Q to your long-term, 20, thirty-year thinking with regards to raising institutional money. What do you make of the plethora of seed funds that we've seen from, from, let's say, very young and very inexperienced first-time fund managers? How do you think about that, and how do you relate to that when people say that is the sign of a funding bubble and too much liquidity and capital in the market?

A Well, I have this saying where the markets are rigged. If you go into your business knowing that everybody's out to get you, like if you would just assume everybody's out to get you, waking up every day is a lot easier. But if you wake up every day looking to just fight the system and be mad that somebody raised this fund, and somebody raised that fund, and the Fed this, and Wells Fargo's stealing from us, I mean, it's fun. I joke about it all day, but I don't, it's serenity now stuff. I get it off my chest, and I move on with an optimistic deal of life. You can't worry about what everybody else is doing. This goes back to that strong convictions loosely held. You have to believe you're going to be doing this, and you have to constantly be selling, to constantly be networking, you have to constantly, you know, be on the ground doing your thing, and including that is writing checks, you know, it's good and bad cycles. So, consistency matters. To be consistent, you got to hop out of bed every day, and you can't be worrying about what other people are doing. You have to have that conviction, and this is what, this is what the world's going to look like in 30 years, and you know, if I continue to do this thing every day, It doesn't really matter what's happening. Is it a bubble today or a bubble tomorrow? I mean, if you invest for a ten-year fund, high likelihood you're going to ha…

AI assessment note: “You can't worry about what everybody else is doing.”