TheFirst Bet Ep 2 Shaun Gold

Hi everybody. Welcome to another edition of The First Bet, and I'm Martin G. Tobias, the managing partner of Insaisive Ventures. And every successful person gets interviewed about how they won. Very few people drag them back to before they knew it would work, when the information was thin, when the money was real, and when they pushed all their chips in anyway. And I've done this as CEO, as an investor. And a poker player a lot of times. And I have a really interesting guest today who I've been wanting to meet for a long time. We've interacted on Twitter. My guest today has 2 decades running, you know, highest-grossing nightclubs in Miami. He went there really young and took a chance on becoming a party promoter in Miami. Then he made a far riskier bet, in my opinion, which is walking away from that and trying to become a VC in a completely different industry. And that's what I want to talk about in an industry that where a lot VCs have a lot of Wall Street pedigree and partners that have run billions of dollars. He came in with a completely different background and tried to create a, a place, and we'll talk about his stuff in, in venture. He is also the creator of Venture Comedy, the GP of Improved Ventures, and a man who one time told Alex Trebek that winning is for losers. Alex Gold, welcome to The First Bet.

Well, it's Sean Gold, but thank you. What a risky bet.

Oh, Sean, sorry.

Hit me. Hit me.

My, my AI is all wrong.

Yeah.

So, you know, we talked a little bit in the intro. You know, making that bet when you were young to move to Miami and do things is, is interesting. But what I want to talk about is capital allocation. And it seems like you took your experience there. I want to go back to the time when you decided to pivot from being a promoter to a VC. And tell me how you thought about that moment and take us back there a little bit. What was going through your mind and how did you think that this would be a good pivot for you to make?

So, well, first, thanks for having me. I love the intro. Thank you. But yeah, I mean, listen, if there's one mental model that I have to keep coming back to, it's I don't really ask whether something is likely to work or fail. Okay. I ask whether the upside is dramatically larger than the downside. Okay. And if that's the case, I'm gonna go for it. I don't like to hem and haw. I just like, like to go in. The VC thing came out kind of inorganically. I mean, I couldn't spell VC, you know, it's like, wait, what VC? What's that mean? You know?

Yeah.

But it came out just because, I mean, I had, when I was doing the nightlife, so many clients across industries and, you know, I got suckered into working at the startups. I was not a startup guy. I was an entrepreneur. I liked marketing. I liked hustling. I liked doing my own thing, but I didn't know anything about, you know, any of this stuff, right? Like cap table. I thought that's something you buy at IKEA. It's a cap table, you know? So, you know, essentially I got suckered into working for a startup and then I got suckered into working for another one. And the next thing you know, I'm working for all these startups, right?

And what are you doing for them?

So at the time it was just kind of general connecting and marketing, which kind of grew into what I do. Still now for a lot of startups and venture capital firms, which is, you know, narrative structure, ghostwriting, connecting, all of that. So anything technical, I'm not the guy, but you know, anyone to say, hey, you should meet this person. Oh, how do you know this person? Oh, okay. Well, he was a client of mine. I met him on this yacht party I did, or I met him at this pool party I did, or this girl I knew introduced me. So I already had all these warm intros, right? And I was just never the person that's like, oh, you got to take care of me if something happens. It was just like, Here, you should meet this person. Have fun. I don't know what you're going to talk about. And as it came on, especially, you know, as we got into the pandemic and everything was on lockdown, I started networking a lot. I was on Lunch Club. I don't know if anybody remembers it. I love Lunch Club. It was hot for like a month during the lockdown.

Oh yeah. I remember Lunch Club. So tell me, what time was this again when you were making this decision? Is these 3 years when you worked without money trying to start a VC firm?

Yeah. So essentially I got out of the nightlife in late 2018. I was doing private events here and there. I was working with startups. People kept mentioning VC. A lot of people kept saying I should get into VC, especially people that work at VC. I said, well, you should hire me. Oh, I can't. Okay. But it sounds fun. And then during the pandemic, when everything kind of came to a halt, I mean, Lunch Club kept giving me venture capitalist introductions. So I kept talking to all of them and talking to them and learning. And then, you know, you start to realize at a point where it's like, Hey, if these people could do it, it can't be that hard. They got no social skills. They understand, you know, the numbers and all that stuff. It can't be that hard. I mean, I was a guy. I mean, I still can't do financial model. If you mentioned financial model, I'm going to say, well, how does she look? You know, really, what brand does she wear? What kind of financial model are we talking about? But yeah, I started, you know, just networking and doing it and started just really learning it. And there really isn't like a playbook. Sure, there are some books, but it was really kind of like a batch of different thought leadership from different funds, from different Silicon Valley gurus, from all this different stuff about different things. And I really went into it. And that's when I also started working with OpenVC. I started building out their content. So that was also a learning process because I went in there to like really, really, really delve into it. So I mean, when I talk about learning process, I wrote like a blog post on the history of venture capital. We're talking going all the way back to, you know, did Columbus do a startup pitch to the Queen? Did he have a TAM for the New World? All the way up until like Arthur Rock, this is the foundation of Fairchild Semiconductor, the launch of Sequoia, Kleiner Perkins, like everything. I want to know everything about it from every great investor, every great investment returns, every single, you know, there's no book for it. There really isn't like here, here's a book on venture capital and here's every single term you should know. Yeah. Right. But I thought it was interesting. And then I connected with someone that we just started talking for, you know, a long time. And she was starting out a fund with people that actually knew the numbers, right? Like the ex-Wall Street people that managed the billions of The ex-hedge fund people, you know, they say hedge fund. I thought they're talking about gardening. I said, what are you talking about hedge funds? I, I've got a backyard, you know, but like all that. Well, what I'm good at is again, kind of seeing things that aren't really there, seeing the opportunity, making fun of the opportunity and making, putting the fun in fun. Right. And yeah, it was literally like, you know, there's nothing there. And I think you have to have a measure of, I don't wanna say you have to be insane. I have to say that, and this goes for startups as well, that If the thought of something seems crazy to you, then you weren't crazy to begin with. So going back to the mental model of like, listen, is this going to have an upside that's dramatically larger than the downside? A lot of people, even if you have that, are gonna say, I need $100K upfront to even consider it. It's like, well, this ain't the game for you, right? You know, or, or I need, I need, I need all these benefits. I need everything. It's like, listen, I'm used to having nothing to work with. That was my life. It was nothing to work with. You were only as good as your last party, right? So that mentality went into this because it's the same thing. It's, you have to think long term. You have to be patient. You have to actually, you know, see things down the line, years down the line that you're probably not going to see. Um, and you have to stay sane. And a normal person is like, no, I want the money now. You know, it's always like the case where, you know, if someone came to you at OpenAI 10 years ago and said, you should really work for us. We're going to be changing the world and we're a nonprofit. Going to say no, but a year ago, or, oh wait, you got all these secondary deals and oh wait, how much are you paying? Oh, I love it. Get me in. I'm going to go there now. I could do it for you. Like, it's too late. It's the same thing that used to happen at the clubs where it's kind of like I would have Justin Bieber, right? Everybody want to come. But when it's the random Wednesday, when there's someone you never heard of and it's empty, you won't even pick up the call. And that's the same thing when it comes to startups. The same thing comes to venture. People only want to be on the bandwagon when it's hot. I've been a strong believer since the Series D Okay. Since the pre-IPO, I've been a fan.

Exactly.

Yeah. That's the first days.

That's funny. The way you underwrite something when it's later and there's a lot of information is very different than the way you underwrite something early. So you started working on content for some of these other VCs. And I do think that very few of them understand narrative. And so that's, that's a good thing, but tell me, take me back to when you decided to start your own fund and ask LPs to give you money or, or to put your own money into a fund where you thought you were good enough, where you had enough connections to actually be able to be good at picking, you know, startups? Because I think that's a different process than, you know, oh, I have some narrative skills. Like how, how did you decide to deploy your own capital and how did you convince LPs to give you capital when, when they are used to seeing people that Stanford GSB, Harvard, you know, ex-I-banker or some kind of shit like that. You have a good story, but it's a non-standard story that LPs might be used to. Yeah.

I mean, well, here's the fun thing about it for everyone that wants to work in venture, raise a fund or any, do anything requires money because I've done it all. Entertainment properties, startup, anything. It's a long slog and nothing matters until the wire hits the account. People are going to say they love you. They're in, it's going to be great. Can't wait to do it. Can't wait to join you for the journey. Every single cliché thing, nothing matters. And with the, with the fund that was improved, that was around 2022. When it became real, like, okay, I'm going to put my money into this to make sure we have everything. People think I'm starting a fund. Okay, well, you can't just start a fund. It's not like going to like— it's like incorporating an LLC. Okay? It's not just like you need an auditor. You need to have like everything in place. You need to have, you know, your back end, your front end. It's not like here's $500 and let's, you know, let's start investing on Monday. It's not. So requires a lot of upfront capital just to, just to put the logo out there. Right. And the problem is that a lot of venture is very fluid. Now at this time, this was the post-2021, the greatest thing ever. Let's put all the money in. Everything's going to be great. We're going to all be billionaires. And now we know years later that, wait, where'd the billions go? What happened? It was just here. You know, like we learned that. I think if I was going to coin it, it was a 2021 rise of the zombie fund, right? Everybody came out. Everybody started, everybody started making bets, but the returns have not been there. And our case with it, it was just, you know, our capital because yeah, we have all the LP contacts. We have people that love us. We have people that support us. They're just not a gangster enough to write a check. My, my, my saying is always this, is that everyone's a gangster until they got to wire the money. Okay. That's it. Yeah. That's it. You can have 100 emails. You can go to, I don't know, you go to Monaco with them. You can hang out with them. But nobody is real. It's all, hey, what's the number? I'm going to send you the money. And that's what—

so tell me, so tell me how big, how big was the first fund and how much was your and your friends' money versus other people that you had to convince of your, you know, strategy?

Yeah. So we didn't have any outside. It was all our own capital. All your own capital. Yeah. I don't want to give it. I mean, I don't want to give a number. Okay. It's because—

okay. Oh, that's fine. That's fine. But it was all our own capital.

It was our own capital. But we had— what I want to— what I want to make clear for everyone listening is that we had like close to like a dozen people that were in. Okay. That was a selling point where it's like they're in. We had someone that had their own fund that we're going to roll it into ours. It was going to be like a GP-LP structure. Got all the paperwork. Okay. Everything was in. And then one by one, they were not in. They were— they were in the inbox, but they were not in. So what happened is we then had to pivot. Okay. Because again, it's not like, oh, best case, you put our money in, let's close it. No, like we're very tenacious people. We know that it's a long-term bet. We're going to make something happen. We're going to make plays and we're going to do it with or without you. And I think that that's kind of a determination that, you know, it sounds pretty fun on Twitter, but when you're going through it, it doesn't sound so fun. It's not cool. And, you know, again, it's not like we don't have people that, you know, can deploy. I mean, we, we, we did some stuff with a client who's— I'm not going to say it, but well over a billion net worth. Okay. Billion net worth. Real deal. But just because they have the money doesn't mean they're willing to part with it. That's how they become a billionaire. They're, they're some of the worst people. Not say the worst, but they're some of the ones that hold on to the money because they're very like, they take a long time. They're very analytical. They're very like, they're, you're not the priority. And with that's the case, and that's just not the only one billionaire I've met with. I had, as when I was doing nightlife, one of the richest people on the planet was a client of mine. Same thing. So, you know, it's, it's very tough. So you have to be sure that if you want to do this, or anything that you want to raise capital for, you have to have the understanding that until you wake up and you have that notification that the money has been wired into your account, nothing is real. And it's up to you to make something real happen.

It's, it's true. I see, I see that all the time. I love it when I talk to a founder and he's like, oh yeah, we have a round and it's all committed. And he mentions like VCs and I call them and they go, no, I haven't actually committed to that round yet. Founders overpromise all the time. And I think that's one of the problems in the business overall. But let me, I just want to get a final point on when you were starting your funds, you ended up being you and your friends, but what were the things going through your mind at that time that was the anti-case or the negative case? You said that your, what got you to do it was that you thought that upside was asymmetric. And so that's why, yes. But, but tell me, steelman for me a little more. What were some of the negative things going through your mind? Were you worried about not being successful? Were you worried about losing your friend's money? What were some of the other things that, that made the case against it? I mean, you were start closing it in '22 and '23, which is right after this sort of bubble of, of, of '21. What were some of the other things going through your mind that were arguing against starting a fund at that time?

Okay. For me personally, for me personally, what had happened was after the pandemic, I came back to nightlife because there was a boom. Everybody was vaxxed.

Yeah, everybody wanted to go out.

Yeah. So there was— I mean, it was just, it was kind of like, what's the point of me? I'm throwing money away. So at the same time as you're doing this, because, you know, to me it's like, all right, you know, I'm back in nightlife. I got this. If I lose money, whatever, you know, at the same time, I literally the same like week that I have to put my money in, right. And to just to get this going. So I had to move. This is the highest, uh, they sold the apartment I was in for like 8 years. So I had to find a new place to live, which at the time in Miami was like the highest inflation. It was the post, the post-COVID, everybody's coming to Miami. Rents jump overnight from like $1,500, you know, for a 1/1 to $3,000, right? Like it was just horrible. Horrible. So I had to move, right? So that was on my mind and I had to, you know, and at the same time with nightlife, They made me, uh, they offered to give me a real job where it's like a Monday to Friday, 9 to 5, whatever, you know, with a salary and all that stuff. And I couldn't do anything else. It was like, you know, I couldn't do the lectures I do. I couldn't work with other clients, couldn't do anything unless it was after, you know, on the weekend, it just wasn't going to work. So I walked away from that, meaning I also, they wouldn't let me do the stuff what I was normally doing, which was being out on the weekend. No problem. So all of this, it was like a perfect storm, but at the same time, One, I'm a person of my word. If I say I'm going to do something, I'm doing it right. That kind of meant more to me than like anything else, right? Was like breaking my word. You know, that's number one. Two, again, it was very hard to see when you're in the middle of the storm, but I knew that this would be a gamble that would pay off. Not within the next week, the next month, probably not within the next year. This would be a gamble that would pay off and it would allow me to operate at a level that I've never been at before. Even though it was not a good time for the investment, I could have definitely used the money. I could have definitely, you know, have, have changed tactics. But I just— something inside that, that inner voice, the North Star, you know, just said, do it. So it wasn't easy. Trust me, it was the trepidation to go on your keyboard and do it, you know, the trepidation. But at the end of the day, it worked out. But at the same time, it just— you have to, you have to have that kind of mentality. And not everyone has that. And it's you know, you, you have to think in terms of, of years, if not decades.

So, so, so one of the things that I found talking to, to people about that is this, is that people who have the confidence to make a, a, a hard decision like that, you were giving up some guaranteed money for some non-guaranteed money because you thought there was asymmetric upside. But you've gotta somehow have a, some sometimes even irrational belief in your own self to, to make those kind of bets. Where do you think you got the belief in, in yourself? Was it, you know, from your parents, from a relative? Was it something, you know, the confidence that you got doing crazy things in, in the nightlife? Where do you think you got the confidence in yourself to be able to make a high-risk bet and to give up some, something that, that a lot of people would say is, you know, more secure?

I think it comes from just my vast amount of historical knowledge. And I always read, I'd read a lot of history, business history, military history, whatnot. And just the people that make history are the ones that rarely played it safe. You know, they just went after what they were going after. And one, I'm naturally stubborn. Two, I've always, I've had like a personal track record of things that I always went after. I have a pretty good win to lose ratio. Not saying I haven't lost, but I say the losses are less. And again, the nightlife, you know, I did crazy stuff in my life that was never done before, right? Like I used to at 17 fly to the Bahamas to throw parties. Okay. I used to fly over spring break. This is before cell phones at all. I don't know what I'm going into, right? I go into it and I just, you know, crazy bets and do it. Same thing with Miami. You know, I don't know anything about Miami. I moved down here, no contacts or anything. I said, this is what I have to do. I don't know how I'm going to do it. There's something called the what now. I'm going to coin this term. What now? You want to do something, so you do it, but then you're like, okay, great. What now? And the what now is the part that no one wants to brag about, talk about social media, or even live through, because that's when you have to actually do what you intend to do. You have to actually put into action the thoughts and build out the structure and all that. And it's not overnight. It takes a while. But that, again, with nightlife, it took me 2 years to really establish myself. Like, and that's 2 years of losing money, losing, having people make fun of me, girls laugh at me, all that stuff. But within that 2 years after that, I sacrificed those 2 years to get almost 2 decades of a rocket ship, right? So it's a small— when you look back at it, it's a small thing. So that's kind of also with me where it's like, yeah, you got to eat 12 to 24 months, winter, summer, winter, summer. So you got to look at it.

You can't look at it like, so you did that in the nightclub business and you had that maybe gave you some confidence to do it again. Going into venture. So what, for listeners here, you've mentioned a couple frameworks of how you make, you know, higher risk decisions. One is if the upside is, you know, much greater than, than the downside. Are there any other frameworks that you use? And I, I like your what now, what, what, what other useful things could listeners pick up from your experience about how to make these higher risk, uh, decisions?

So I think the thing that a lot of people discount is that they outsource their mind to social media and now to Claude and ChatGPT, but to the free plans, not anything special.

Yeah. Yeah.

So the best parts about you, the most unique parts about you that are going to establish your niche and your framework and what you do are not something that are outsourced. They come from within. You have to discover them. And a lot of people don't like to look within. They just want to copy what else someone is doing. I see it with a lot of founders. They copy the decks, they copy the playbook, they copy other companies. There's nothing that's original. That's a core competency that makes them stand out both from a personal standpoint and from a venture-backable standpoint. You know, so with me, I mean, if you want to think of like, you know, just another framework, you know, I, I don't want to say I have a career, but why not? Let's say I have a career. I never had a real job, but I guess I have a career. So I kind of bet that career and just Being unique, random, weird, unique. Okay. Like it doesn't fit any mold, right? It does not fit. You know, the whole point of me going to university and college was to throw parties. I didn't care about the major. My major was entrepreneurship, not because I had a, uh, I mean, I love entrepreneurship, don't get me wrong, but it was the easiest one they offered. It was the easiest business one I could get. There was, there was, that was it. It allowed me to be out at night and. Sleep till 1 and show up for an hour a day or 2 hours a day, right? So you want to just bet on yourself, but your personal core competencies. That's how the Venture Comedy thing came out, right? The, I'm going to combine venture capital with being funny. Let's see if it can work. And it has, right?

Absolutely.

Bet on yourself and what you personally have, because anyone that gives up their internal strength, their way of thinking, when they outsource it to a large language model, or they buy a course from an influencer, They try to mimic the Mark Zuckerbergs and Steve Jobs and everything. They are giving up the strategic advantage that is going to have them, you know, that's going to give them strength to keep going, to keep them keep going throughout, you know, whatever they decide to do in their career, whether it's a startup, whether it's working for a company, you're going to need the inner strength to do it and to accomplish something. So I think that's, that's, that's something. And I think that, you know, another angle is that, you know, and this applies to venture is that. Survivability is a very good core strength, is a competitive advantage. Okay? If you can survive longer than people with more talent and resources, then you will win. Okay? Yes, you have to be a mosquito. Nobody wants to be a mosquito. But have you ever tried to deal with a mosquito at night and the lights are off and you're trying to slap it and it's buzzing in your ear and you can't find it? Okay? You want to be that mosquito because a mosquito could take down a giant. If it's persistent enough and if it can survive long enough, you know, and variance works, right? You know, you learn as you, as you grow, you learn. I mean, there's always the, the, you know, there's a stupid cliché that's happening right now. And you see everyone listening probably sees it. It was like, AI is not going to take your job. Someone that knows how to use AI is going to take your job. No, the person that could operate in a world without AI and with AI is going to take all of your jobs. Because unlike when, oh, Claude's not going down, Claude's going down, the tokens, how am I going to make toast? They know what they're doing. Okay. They instantly can look up, go to look into a book or go use Google or think of something or recall some information that they have and they could do it themselves. Might take a little bit longer, but they don't have to prompt anything. They can prompt their own mind. Right. So I think that's something also, if you can have that, where you realize that AI is, you know, I say that AI is like having a hammer, you know, and it's good. You want to have a hammer, but don't let it convince you that just because you can pick up a hammer that now you can build an entire house in a weekend. You know, with no resources, because you can't, it's a tool. You still need to learn stuff.

I agree.

You still need to learn stuff with or without.

I, I, I, yeah, yeah. I, I, I agree. YC did this study and they went through and said, what are all the things that people come through YC? What is the number one criteria that determines success versus not success in YC? And they looked at everything. Did you go to Stanford? Did you go to Harvard? Where did you work? Blah, blah, blah. None of that shit mattered. What mattered was one thing. Did the founder quit? Did he, did he, what is he a, not a quitter? And the founders that were not quitters that, that stuck to it, that had their own opinion and that, that, that even if they pivoted, those were the ones that were successful. It was not correlated to any course that they took or anything like that. And it sounds like that has, you know, gotten, you know, been true in, in, in your life too. Even when you didn't know what you're doing, if you didn't quit and just kept swinging the bat, it, after enough time, it worked out.

It's true, but it just, it's after enough time. I mean, I equate it to be honest with you're escaping from prison. Okay. You're in the château d'If of your mind and you're Edmond Dantès. Okay. And you're going to have to chisel through the wall, get through the cell, go under the ground, chisel to the outer wall, make it to the roof, rappel down the roof, get to the ocean, get to the boat, like build the boat. Like that's what it is. It's not sexy. What's sexy is like, look, we're making money. Look, we're doing this. That's sexy. But to get to there, it's very, very difficult. Nobody wants to start at the bottom, especially now. Social media gives a lie that it's so easy. I mean, even with all the AI tools, I mean, it's kind of like OpenAI and Anthropic have tapped into the greatest resource on the planet, the weekend warrior. You can build a company over the weekend with our plans, pay $200 a month, and you get it. You're going to be an entrepreneur. You could 5-code your way to a million. You don't need any skills anymore. You just need to know how to prompt. You just need to have that. And you're good. And the reality is, no, you still need to have the ability to sell, to market, the taste, the judgment. I mean, there's so much here, but everyone's like believing that. And I feel like we have now, we're entering a period of, you know, technology and business where it's not even a graveyard of failed companies anymore. It's a necropolis. Okay. It's a city of the dead and it's just going to be more and more. So, you know, you have to be that founder or that individual. That has that ability to keep going no matter what, and you keep going and it's okay to pivot. You know, that the whole thing is it's just, it's fine to pivot. What's not fine is like, forget this, I'm going back to selling aluminum siding. You have to stick with what you're doing.

Yeah, I agree. I mean, I've been investing for a long time and it, you, you know, the barrier to build the software has gone down, but the, the, the distribution is still a problem and finding a problem that's worth solving is still a problem. I think it's the greatest time to be a startup founder, but it's also harder in ways that people aren't used to. If they think they can just write software, that doesn't solve the problem anymore. You gotta be much more attuned to the market and everybody can write the same software that you can now as, as fast as anybody can. So, so let me just summarize another thing that you talk a lot about. Online is mistakes that you see VCs and founders make. You just mentioned one that founders maybe think that it's easier to start a company than not. What are the primary founders or mistakes that you see or where people get off track as a founder or as a VC?

Well, is this a two-part podcast? Because there's so many, you know.

Well, maybe just give us like two or three of each one. Okay. Because we're getting close.

One, I mean, underestimating how difficult it's going to be, overestimating how easy raising outside capital is going to be. And just the general ecosystem, people don't— the navigating the ecosystem, right? You know, there's so much that goes into it. And I think when we talk about, you know, you just said trying to find a problem needs to be solving. Okay. First, let's solve your internal problem. One. Poverty. Let's make some money. Okay. Let's have a track record in doing what you do very well so that when you do start a company, you have the track record and the core competencies to deliver on that. Right. I don't know anything about biotech, so I'm not going to be in a biotech deck doing anything for a biotech company, even though I might have an idea for it. Just doesn't make sense. The raising capital. I mean, you know, everyone likes to talk about the wins. They go to Twitter, they see all the wins. They go to LinkedIn, they see all the wins, but those are the outliers. There are countless people that don't even get a response. You know, it's, it's something that it's nobody, it's not sexy to talk about. It's sexy to say I did 500 outreach and that's how I raised $5 million. Not I did 500 outreach and I haven't raised a single dollar. Right. People think that raising capital is like Shark Tank. I mean, I've worked with people that are Shark Tank alums. They've actually went on there and they won and they raised capital and they're on TV and it was great. It's not like that at all. Right. Even that Shark Tank episode, what you see for 7 minutes is usually the result of 3 hours that was cut down to, for TV. The fact that people think that there's this, how should I call it, the trust me, bro energy where it's like, this is going to be the next big thing. Trust me, bro. Why? Just trust me. Right. The fact that there's really an overreliance on AI to the point that Claude, make me a deck. All the decks look the same. They're not really putting any thought into the deck or into the storytelling or into what actually goes into a deck. And it's not like it's a cloistered, esoteric You know, buy my course for the deck. It's none of that. It's pretty much you just have to spend time researching what goes into a deck. We're not trying to trick you. You just have to find the time to do it and put the thought into it, you know, and people don't. People literally still to this day with all the free resources, with all the podcasts, with everything out there, they're still giving 30 to 40 slide decks for a pre-seed. Yeah. You know, I don't know like why they are. I don't, you know, investors want to see an opportunity and what I'm looking at makes me want to see an optometrist. Okay. Like it's a text. It looks like the Dead Sea Scrolls. Like, what is this? Yeah. You know, so it's, there's just a lot of, you know, ignorance that I think are, that is there in not only just the founder side, but also on the VC side as well. You know, VCs like to champion their one or two wins, right? If that were, it only works in venture capital. If I were to go to an operating room and I needed an operation and the doctor came out and said, I'm just going to be straight with you. 9 out of 10 of these fail, but don't worry if it does work out, you're, you're gonna live for, you're gonna live for 50 more years, but 9 out of 10 fail. Okay. I'll see you in the operating room. Right. You would run for the hills, but in venture capital, you have one win. Forget all the other ones, the one win, and that's it. You got your one win forever. And that's your expertise. That's it. You know, you got, you got that massive one swing that hit the grand slam and then everything else you don't even talk about. Excuse me. What about the 8 other portfolio companies? What? Never heard of them. Let's go back to talking about the Figma, the Facebook, the Uber. Yeah. You know? The, the OpenAI, the Anthropic, the SpaceX, you know, like they, they, oh, it's always that. So it's a very, it's very weird. Right. And it's also very like, it doesn't make sense. I wrote about this last week where, you know, if you don't understand venture capital, it's okay because the people working in venture capital probably don't understand it either. What do I mean by that? I mean that venture capital makes a big deal. A lot of early stage funds make a big deal of seeing something that's never been done before by someone that's never done it. New talent, new blood in a company that's going to change the industry and the world for generations to come. And when you first apply and you get a meeting, the first thing that venture capitalists will ask is, have you done this before? What? You just said you want something that's never been done before. It's never been done before. It says right here on the thesis, reach out if you're building something that's never been done before. It's like saying, okay, I'm working on teleportation. Have you, have you teleported something? No, I haven't. Okay. Well, come back when you have. Wait, what? You know? Yeah. Or it's, it's kind of like, you know, the track record. Right? Yes, you need to have a track record of doing it, but if you're doing something new and you're building something new, then it's kind of like, well, what have you done before similar to this? Nothing. You just, we just went over this. Right? So it's, it's a very like awkward and very weird. So I've, I've, I try to make sense of it through the comedy. I try to make sense of it so that people understand it. Um, cause I do think venture capital, a lot of them take themselves way too seriously. You know, it's like you're writing a check for a new invoicing tool. You're, you're not. Saving the whales. Let's relax. Okay. Let's, let's, let's calm down, Chad. Okay. It's, it's a new invoicing tool that integrates with your CRM. It's not the world-changing, you know, universe-shattering thing that it is. So there's a lot of—

there's, there's, there, there's very few of those. And the vast majority of venture capital does get deployed to solving just sort of pedestrian problems. I mean, there's very few unicorns for a reason. There are very few people like Elon Musk that can say we're going to fucking Mars and everybody's like, okay, so not everybody's like that. Well, I really appreciate your perspective and thanks for going deep on some of these hard decisions that you've made. Maybe you can tell, we'll put it in the show notes, but where can people find your commentary? And I do think that your combination of comedy and writing does a good job of helping founders and VCs understand this hard problem that they're both trying to work in.

Oh, that's a test as well, going into my fundraising deck. Don't worry, there will be no decks. It's okay. I appreciate it. So yeah, LinkedIn primarily and X. It depends how much you want to read. LinkedIn is more of long form. I like LinkedIn. I just, I like connecting with people who actually have a real profile picture and not lasers coming out of their eyes. It's a personal preference, just, but, but I'm also on X, so we'll put those down there. And we're launching a YouTube channel, hopefully at the end of the summer. If you love the content, you're going to love the videos. That's right. Venture comedy videos coming out. So I'm pretty excited about that. Bringing it to life. And yeah, feel free to reach out. But when I mean reaching out, I mean, do not send me a ChatGPT-generated slot message with my name spelled wrong with the The bracket's still in there along with your deck, business plan, marketing plan, and the partridge in a pear tree. Just say, hi, heard you on the podcast. It's funny. Cool. That's all you need to say. Okay. Don't Trojan horse me with it's funny. And you know what's also funny? B2B SaaS is still operating like it's 2016, which is why I'm working on this. No, that's not funny. That's a Trojan horse pitch. I don't want it.

Okay.

Thank you for having me.

All right.

Fun.

All right. Well, I look forward to yacking with you more on Twitter and everything else. And if I get down to Miami, maybe we can go, uh, have a taco or something. I love it down there.

Thank you for your time, sir. I'm always here. Thank you, sir. I appreciate having me.