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Making capital allocation decisions in low information environments and with alot of uncertainty is hard. This show talks to people who do this every day and teases out how to be good at it.
Martin Tobias (00:01)
Hi everybody, ⁓ the welcome to another edition of The First Bet. And I'm Martin Tobias, the managing partner of Incisive 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 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 two decades running ⁓ you know, highest grossing nightclubs in Miami. ⁓ he went there really young and took a a 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 in an industry that where a lot of 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.
Shaun Gold (01:29)
Well, it's Sean Gold, but thank you. What a risky bet. Hit me. Hit me. No. Yeah.
Martin Tobias (01:32)
Sean, sorry.
My A my AI is all wrong. 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 and how did you think that this would be a good ⁓ pivot for you to make?
Shaun Gold (02:12)
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 the hem and haw. I just like like to go in. ⁓ the V C thing came out kind of inorganically. I mean, I couldn't spell V C.
You know, it's like, wait, what? VC what's that mean? You know? ⁓ but it came out just because I mean I had when I was doing the nightlife so many clients across industries. And la, you know, I got suckered into working at the startups. I was not a startup guy, I was an entrepreneur. I like marketing, I like hustling, like 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 ⁓
Martin Tobias (02:46)
Yeah.
Yeah.
Shaun Gold (03:11)
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 so ⁓ at the time it was just John and like kind of general connecting and marketing, ⁓ which kind of grew into what I do still now for a lot of startups and and venture capital firms, which is you know, narrative structure, ghostwriting, connecting, all of that. So anything tactical, I'm not the guy, but
Martin Tobias (03:21)
And and what are you doing for them?
Shaun Gold (03:41)
You know, anyone to say, Hey, you should meet this person. how do you know this person? okay, well, he was a client of mine, or 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, you gotta 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 gonna 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. ⁓ and I
Martin Tobias (04:14)
yeah, I remember lunch
club. So tell what time was this again when you were making this decision, is these three years when you worked without money trying to start a V C firm?
Shaun Gold (04:22)
Yeah, so essentially I got out of nightlife in late twenty eighteen. 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. 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.
Martin Tobias (04:39)
Yeah.
Shaun Gold (04:47)
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 mention financial model, I'm gonna say, well, how does she look? You know, really? What what brand does she wear? What kind of financial model are we talking about? ⁓ but yeah, I started, you know, just networking and and doing it and started just really learning it. And there really isn't like a playbook.
Martin Tobias (05:05)
Yeah. Yeah.
Shaun Gold (05:17)
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 groups, 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 ran 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.
So, you know, did Columbus do his startup pitch to the Queen? Did he have a TAM for the new world? All the way up until like Arthur Rock, this the foundation of Fairchild Semiconductor, ⁓ the launch of Sequoia, Kleiner Perkins, like everything. I wanna 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, 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 manage the billions of dollars, the ex-hedge fund people, you know. They say hedge fund. I thought they were talking about gardening. I What are you talking about? Hedge funds? I I don't got a backyard, you know, but like all that. But what I'm good at is again, kind of seeing things that aren't really there.
Martin Tobias (06:30)
Ha ha ha.
Shaun Gold (06:39)
Seeing the opportunity, making fun of the opportunity, and making putting the fun in fund, right? ⁓ and yeah, it was little like, you know, there's nothing there. And I think you have to have a measure of I don't want to 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 a hundred K up front to even consider it. It's like, well, this ain't 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 nightlife. 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, you're probably not gonna see. 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 open at OpenAI 10 years ago and said, You should really work for us, we're gonna be changing the world and we're a nonprofit, you're gonna say, No.
But a year ago, or wait, you got all these secondary deals. And wait, how much are you paying? And I love it. I get me in. I'm gonna go there now. I could do it for you. Like it's too late. It's the same thing that used to happen with the clubs where it's kind of like I would have adjusted Bieber, right? Everybody wanna come, but when it's the random Wednesday when there's someone you've 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 that comes to venture. People only want to be on the bandwagon when it's hot. I've been I've been a strong believer since the series D. Okay, since the pre-IPO, I've been a fan.
Martin Tobias (08:22)
Yeah.
Shaun Gold (08:26)
No, not since like the first the first days.
Martin Tobias (08:27)
Exactly. Yeah, that's
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 I do think that 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, 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
Shaun Gold (09:22)
So
Martin Tobias (09:24)
Stanford GSB, Harvard, you know, X 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 hearing.
Shaun Gold (09:35)
Yeah, I mean, well here's the fun thing about it for everyone that wants to work in venture, raise a fund or anything do anything that 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 gonna say they love you, they're in, it's gonna be great. Can't wait to do it, can't wait to join you for the journey. Every single cliche thing, nothing matters. And with the with the fund with improve, that was around
Martin Tobias (09:52)
Mm-hmm.
Shaun Gold (10:05)
2022, when it became real. Like, okay, I'm gonna put my money into this. I'm gonna make sure we have everything. Cause people think, I'm just gonna start 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 saying 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 bucks and let's, you know, let's start investing on Monday. It's not. So it requires a lot of upfront capital just to just to put the logo out there, right?
⁓ and the problem is that a lot venture is very fluid. Now at this time, this was the the post-2021, the greatest thing ever. Let's put all the money in. Everything's gonna be great. We're gonna all be billionaires. And now we know years later that, wait, where the billions go? What happened? It was just here. You know, like we we learned that I I think if I was going to coin it, it was ⁓ twenty twenty-one rise of the zombie fund, right? Everybody came out, everybody started, everybody started making bets, but the returns have not been there.
Martin Tobias (10:50)
Yeah.
Shaun Gold (11:05)
⁓ and our case with that 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 to enough to write a check. My my my saying is always this is that everyone's a gangster until they gotta wire the money. Okay. That's it. That's it. You can have a hundred 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 until hey, what's the number?
Martin Tobias (11:24)
Yeah, yeah.
Shaun Gold (11:34)
I'm gonna send you the money. And that's what you kinda learn. Yeah.
Martin Tobias (11:36)
So tell so tell me how big
how big was the first fund and how much was your and your friend's money versus other people that you had to convince of your ⁓ you know strategy?
Shaun Gold (11:46)
Yeah, so we we didn't have any outside. It was all our own capital. I don't I I yeah, I don't wanna give it I mean I don't wanna give a number, okay? It's cause it's just not yeah. But it was all our own capital. ⁓ it was our own capital just be but we had what I wanna what I wanna 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 phone that were gonna roll it into ours. It was gonna be like a GPLP structure.
Martin Tobias (11:50)
All your own capital.
Okay. that's fine. That's fine. So it's your own capital. All right.
Shaun Gold (12:15)
Got all the paperwork. Okay. Everything was in. And then one by one, they they were not in. They were they 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, ⁓ best case, we put our money and let's close it. No, like we're very tenacious people. We know that it's a long-term bet. We're gonna make something happen. We're gonna make plays and we're gonna 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 gonna 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 there's some of the the worst people that say the worst, but they're some of the ones that hold on to the money.
Martin Tobias (12:50)
Okay.
Sure.
Shaun Gold (13:10)
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 the case, and that's just not the only one billionaire I've met with. I've 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.
Нахін із Р, а не цаптик сантин ріл хапи.
Martin Tobias (13:43)
It's it's true. I I see I see that all the time. I I love it when I talk to a founder and he's like, yeah, we have a round and it's all committed. And he mentions like three 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 I think that's one of the the the problems in in the business overall. But let me I just wanna get a a final point on when you were starting your funds, you ended up being you and your 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 the upside was asymmetric. And so that's why yes, but but but tell me steel man for me a little more. What were some of the negative things going through your mind? Were you worried about ⁓ not being successful? You're worried about losing your friend's money, w what were some of the other
things that that made the case a against it. I mean, you were st closing it in twenty two and twenty three, which is right after this sort of bubble of of of twenty one. What were some of the other things going through your mind that were arguing against starting a fund at that time?
Shaun Gold (14:47)
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 and ready to rock. Yeah. So there was I mean, it was just it was kind of like I d what's the point of me? I'm throwing money away. So at the same time as we'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.
Martin Tobias (14:56)
Yeah, everybody wanted to go out.
Shaun Gold (15:16)
So ⁓ I had to move. This is the highest. ⁓ they sold the apartment I was in for like eight 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 jumped overnight from like fifteen hundred dollars, you know, for a warm one to three thousand. 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 ⁓ they offered to give me a real job where it's like a Monday to Friday, nine to five, 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, I couldn't do anything unless it was after, you know, on the weekend, it just wasn't gonna work. So I walked away from that, meaning I also they wouldn't let me do the stuff that I was normally doing, which is 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 gonna do something, I'm doing it, right? That kind of meant more to me than like anything else, right? It 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 would 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
Martin Tobias (17:01)
Yeah.
Shaun Gold (17:06)
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.
Martin Tobias (17:16)
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 di a a hard decision like that, you're giving up some guaranteed money for some non-guaranteed money because you thought there was asymmetric upside. But you 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?
Shaun Gold (18:09)
I think it comes from just my vast amount of historical knowledge and I always read I le 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 st I'm naturally stubborn, two I've always I've had like a personal track record of things that I always went after. I've pretty good win to lose ratio.
⁓ not saying I haven't losed, but I say the losses are less. and again that the nightlife, you know, gives I did crazy stuff in nightlife 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, take crazy bets and and do it. Same thing with Miami. I, you know, I don't know anything about Miami. I moved down here.
Martin Tobias (18:41)
Mm-hmm.
Uh-huh.
Shaun Gold (19:04)
No context or anything. I said, This is what I have to do. I don't know how I'm gonna do it. There's something called the what now. McCoinist 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 the thoughts and build out the structure and all that. And it's not overnight. It takes a while. ⁓
Martin Tobias (19:12)
What now?
Shaun Gold (19:31)
But that ⁓ again it with nightlife, it took me two years to really establish myself. Like and and that's two years of losing money, losing, ⁓ having people make fun of me, girls laugh at me, all that stuff. ⁓ but within that two years after that, I sacrificed those two years to get almost two decades of a rocket ship. Right. So it's a small and you look back at it, it's a small thing. So that's kinda also with me where it's like, yeah, you gotta eat twelve to twenty-four months. Winter summer, winter summer. It's how you gotta look at it. You can't look at it like
Martin Tobias (19:57)
Yeah. Right. So so
Shaun Gold (20:00)
Day by day, second by second.
Martin Tobias (20:00)
so so you you you did that in the nightclub business and and you had that maybe gave you some confidence to do it again going in ⁓ to 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 you useful things could listeners pick up from your ⁓ experience about how to make these ⁓ higher risk ⁓ decisions?
Shaun Gold (20:36)
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 plants. Not anything special to the free plants. ⁓ 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.
Martin Tobias (20:46)
Yeah, yeah.
Shaun Gold (21:03)
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 on just being unique, random, weird, odd. Okay. Like it doesn't fit any mold, right? It does not fit, you know, I the whole point of me going to university and college was to throw parties. I didn't care about the major. I my major was entrepreneurship. Not because I had a 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 that was it. It allowed me to
Martin Tobias (21:39)
Unique.
Sure. Right.
Okay.
Shaun Gold (22:02)
be out at night and sleep till one and show up for an hour a day or two hours a day. Right. ⁓ so you you wanna just bet on yourself, but your personal core competencies. That's how the venture comedy thing came out, right? The I'm gonna combine venture capital with being funny. Let's see if it can work. And it has, right? ⁓ so bet on yourself and what you personally have, because anyone that gives up their
Martin Tobias (22:22)
Absolutely.
Shaun Gold (22:29)
internal strength or way of thinking that they outsource it to a large language model or they buy a course from an influencer or 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 ⁓
Martin Tobias (22:56)
Okay.
Shaun Gold (22:58)
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 can 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 cliche that's happening right now.
Martin Tobias (23:42)
Yeah.
Shaun Gold (23:48)
You see, everyone listening probably sees it was like AI is not gonna take your job. Someone that knows how to use AI is gonna take your job. No, the person that can operate in a world without AI and with AI is gonna take all of your jobs. Because unlike when claud's not going down that the clause going down, the tokens, how am I gonna make toasts? 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 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 in a weekend. You know, with no resources. Because you can't. It's a tool. You still know how to learn stuff. And you still know how to learn stuff with or without.
Martin Tobias (24:37)
I I agree. 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, di 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 d would 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 e 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 i 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
a after enough time it worked out.
Shaun Gold (25:39)
It's true, but it just it's after enough time. I mean, I I equate it to be honest with you're escaping from prison. Okay, you're in the chateau d'if of your mind and you're Edmund Dante's, okay? And you're gonna have to chisel through the wall, get through the cell, go under the ground, chisel to the outer wall, make it to the roof, repel 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.
Martin Tobias (25:50)
Yeah.
Shaun Gold (26:07)
Look, we're doing this. That's sexy. But to get to there, it's very, very difficult. It's nobody wants to start at the bottom, especially now. Social media gives a lie, but it's so easy. I mean, even with all the AI tools, I mean, it's kind of like you know, 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 free with our plans, pay $200 a month, and you get it. You're gonna be an entrepreneur, you can find your co.
Five quote your way to a million, you don't need any skills anymore, you just knew how to prompt, you just need to have that, and you're good. And 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 gonna be more and more.
Martin Tobias (26:45)
Yeah.
Yeah.
Shaun Gold (27:01)
So, you know, but you you have to be that founder or that individual that has that ability to keep going no matter what, and you keep going with it and it's okay to pivot, you know, that the whole thing is it's just it's it's fine to pivot. What what's not fine is like, forget this, I'm going back to selling aluminum siding. You know, like it's you have to stick with what you're doing.
Martin Tobias (27:19)
Okay. Yeah.
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 is still a problem and finding a problem that's worth solving is still a 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 and founders ⁓ make. You just mentioned one that founders maybe think that it's easier to start a company than than not. What are the primary founders or mistakes that you
C see ⁓ or where people get off track as a founder or as a VC.
Shaun Gold (28:26)
Well is this is this a two-part podcast? Because there's so many, you know? ⁓ okay. Okay, one, I mean, on ⁓ underestimating how difficult it's going to be. Overestimating how easy raising outside capital is going to be. and and just the general ecosystem, ⁓ people don't the the navigating the ecosystem, right?
Martin Tobias (28:30)
Well, maybe just give us like two or three of each one 'cause we're getting close.
Shaun Gold (28:56)
You know, there there's so much that goes into it. And I I think when we talk about, you know, you just said trying to find a problem that 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. 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 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 that's I raised five million. 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's alums. They've actually gone 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 seven minutes, is usually the result of three hours that was cut down to for TV.
The fact that people think that there's this, how should I I call it the the trust me bro energy, where it's like, this is gonna be the next big thing, trust me, bro. Okay, why? Just trust me, right? ⁓ the fact that there's really an over reliance on AI to the point that Claude, make me a deck. So 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.
Martin Tobias (30:19)
Mm-hmm.
Shaun Gold (30:39)
You know, buy my course for the deck. It's none of that. It's pretty much 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. You know? ⁓
Martin Tobias (31:00)
Yeah.
Shaun Gold (31:01)
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 just that the tech, it looked, it looks like the Dead Sea Scrolls. Like, what is this? ⁓ you know, so it's there there's just a lot of, you know, ignorance that I think are that is there in not only just the the the founder side, but also on the VC side as well. You know, VCs like to champion their
Martin Tobias (31:10)
Yeah, yeah.
Shaun Gold (31:30)
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 operation and the doctor came out and said, I'm just gonna be straight with you. Nine out of ten of these fail. But don't worry, if it does work out, you're gonna live for you're gonna live for 50 more years. But nine out of ten 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
Martin Tobias (31:49)
Totally.
Shaun Gold (31:58)
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 eight other portfolio companies? What? Never heard of them. Let's go back to talking about the Figma, the Facebook, the Uber, you know, the the Open AI, the Anthropic, the SpaceX, you know, like they they all it's always that. So it's a very, it's very weird, right? And it's also very like it it doesn't make sense. I wrote about this last week where, you know, if 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 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.
You 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? ⁓ 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
Martin Tobias (33:06)
Yeah.
Shaun Gold (33:22)
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. ⁓ because 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 that it is.
so there so there's a lot of things.
Martin Tobias (33:50)
Yeah. I mean 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 p 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 of helping founders and and VCs understand this hard problem that they're both trying to work in. Where can people find you?
Shaun Gold (34:35)
that's a testamental
going 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 me. 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 chat GPT generated slot message with my name spelled wrong with the brackets still in there, along with your deck, business plan, marketing plan, and the partridge and a pear tree. Just say, hi, heard you on the podcast. It's funny, cool, it's all you need to say. Okay. And don't, and don't Trojan horse me with it's funny.
And you know what's also funny? B2B SaaS is still operating like it's twenty sixteen, which is why I'm working on this. No, that's not funny. That's a Trojan horse pitch. I don't want it. ⁓ but but but yeah, th thank you for having me. I had fun.
Martin Tobias (35:42)
Okay. All right.
All right. Well I look forward to yakking with you more on Twitter and and everything else. And if I get down to Miami, maybe we can go have a taco or something. I love it down there. Thank you for your time, Sean.
Shaun Gold (35:55)
⁓ yeah, for sure. I'm always
here. Thank you, sir. Appreciate having me.