There were so many things that I did foolishly

during that time, and I'm not just talking about, like,

you know, oh, you know, I wasn't as good at this thing as I am now. It's like, no, like, there was so much opportunity right under my nose.

And I was blind to it. And, like, one of the biggest, like, scary things for me now is, like,

what are those things today?

That are right in front of me, that I'm too stupid to see just like I was too stupid to see it seven years ago when I was doing that other thing.

For example,

Greg, you were in our early mastermind groups,

and the founders of calm were there. And they were talking about how hard it was and how they're just, you know, it was just Alex. It was just kind of like Yeah. It's hard to raise money right now. I'm trying, and and we were just like, dude, it's a cool app, man. You should stick with it. He's like, yeah, I'm I'm gonna just keep going.

And, like, that's a two billion dollar plus company now. And we were helping him, like, dude, why didn't we cut the check? You were there too. I don't know. You didn't kinda check either. Did you? I remember at the time, like, if I'm being honest, like, I felt that

it was too niche. Like, I was like, We were, like, Sean, you and I were focusing on, like

We were doing big stuff. Stuff that was gonna be Yeah. Exactly.

Will hire later. And he's he's got the huge company. Exactly.

There was so many of those. So in our masterminds itself, I think, loom was in there. That's a billion dollar company. And I remember kinda like trying to mentorship and being like, bro, like, you know, that Don't worry. You'll figure it out. This maybe it's not this one, but, like, when you get to your real game, you're gonna be, like, good because of this experience. You were friends with him too. Like, did you invest in that? I I missed I missed I missed it. It was called,

what was it called? Opentest

dot co.

And that's what Loom was originally.

And it, you know,

it felt like,

you know, when you're doing your first startup and

it just feels so shaky because you're it's your first time doing all this stuff. Like, that's what

it felt like. It felt like. And so it was

you know, and then also the the narrative at the time was

don't invest in other people's startups. You got if you if you wanna make it in Silicon Valley, you gotta give

laser focus. So I, you know, my mistake

in my twenties was I came to San Francisco and

you know, I listened to all these VCs with all their narratives,

and I did it. And if I were to redo it, I would frankly just be doing what I know, which is just doing, like, what I'm doing now, which is, like, focused on communities, doing agency services,

you know, focusing on niches and and and web, you know, yeah, just build and experiment and not have the big biggest exits in the world.

I So there there was, like, ten ten examples like that. Like, I remember Alex McCall came over one day, and he we were catching up, and then he went on to start clear. And I remember thinking this guy's fucking amazing.

I should invest in this clear bit thing. And I, like, went over to his office and we, like, hung out. I was like, you have to meet the guys. I was like, I energy of this office, man, like, if I just couldn't do anything besides feel this office, I would be like, they're building a winner in here. And that's also like a, I don't know, it's a billions, multi hundred million dollar company.

He told me at the end, he goes, oh, by the way, I'm buying up,

I was like, what else are you doing? Finally, I started questions. I was like, what else are you doing? He's like, oh, I bought up some stripe shares. The stripe shares available for, like, two billion dollars. So I'm buying a bunch of stripe shares. I think it was him. Maybe it's Josh Buckley. He's one of them. And he's like, I'm buying up Stripechers for two billion. Let me know if you want in. And I was like, two billion. To me, I was like, well, that's like the amount most a startup is worth. It's like, a billion is the top of the mountain. So, like, to me, it was like, oh, there's no upside left. You know? I didn't, like, think from first principles about, like, everybody knew Stripe was fucking amazing. It was, like, the best startup in the whole, like, you know, in Silicon Valley.

And I had this opportunity to go buy Stripears at two billion. And I thought how late I was. And I was like, man, I wish I could have got in earlier. And now, like,

you know, the things I would give for Stripeciers at two billion now, like, it's like,

That's already like,

like a hundred x, you know, from from there. And that was proven. Right? Forget that. Then there was all the services we were using. Like, Fern who's my CTO, he would be like, oh, this is a cool cool product. Let's use this in our tech stack. If I had just invested in all the bills we were paying for, like, software we were using, like, pager duty and elastic search. And so, you know, like, one effort or another. Those were all huge winners that were pre IPO.

So First was investing. The second was, like, project selection. So, like, you're talking about Greg. I did the same thing. I was playing by the rules of, like, I was playing by other people's rules. Meaning, like, what was considered cool at Silicon Valley was to be like a product guy who was building who had a cool product taste and was building, like,

you know, like, new markets and, like, going for the the big billion dollar prizes.

And then I met Sam who was, like, I'm writing this newsletter.

It's free. I'm gonna have, like, newsletter ads in it. And I was like, yeah, but, like, are you gonna do a startup someday?

Like, that's all I felt about it. Right? It's Sam's company.

Sells for more than more than my coffee sold for in the end. He goes, he goes, look, you're good. But basically, like, you're showing up to a knife fight with a knife, and I wish you would show up with a magic wand that would just murder the competition. I'm like, sounded cool. Right? I was like, that's a great analogy. That's a cool story, but, like,

I don't know, man. I think,

the math kinda I think it might achieve the desired outcome, which I'm trying to do here, which,

when I started, I was just trying to be financially dependent by the age of thirty. That was the only goal.

And so so, like, if I could go back and just whisper three things about, like, just strat just strategy. Like, forget life advice, just strategy advice. I would have said,

invest in all the smart people you know. Like, it it'll it'll work out. And if you don't have the money, go convince somebody that you have a bunch of really smart friends that they should give you money to invest in that are in the first thing. The second is invest in all of the expenses on your P and L. So go find all the places you're spending money and go invest in all those companies. That will also do fantastically well. You'll make more on that than your own company. Okay. If you really wanna do your own company beyond that, fantastic. That's great. You're gonna build up skills and you gotta a lottery ticket there that might work. I would have just said, like,

don't try to be Mark Zuckerberg from the social network. Like, think about what like like, basically, there's open your eyes to the problems and the opportunities that exist today. And so, like, you know, whether it was, like, e commerce or Shopify apps or, like, These sounded small at the time, but they sounded small because that's where they were early.

And, like, at that time, I needed a VC to, like, stamp their approval that this was a good market or good opportunity, which by that time is pretty late because what's the VC doing? They're looking at what companies are raising huge rounds, which means, like, four years ago, those were great opportunities. Three years ago, those were great opportunities.

And so I wish I had just kinda been more eyes wide open on, like,

what projects are available to you. And, like, the things that sound kinda nation funny,

those are actually better signals for you than the thing that the VC is saying is be huge or is already huge because it's

often,

you know, those companies to starter, like, you're in a you're in an absolute dog fight and it's just, like, one winner out of a hundred is gonna emerge versus other things where, like, you could basically take,

no no product risks, no market risks. So I had a friend, Vishal, tell me this one. He goes, I invest in companies with no product market fit risk.

I had never heard somebody say that. It didn't even make sense to me. I go, what do you mean? Like,

every startup is product market theorist. He goes, no, it's not. Like, what? And he goes,

he was the one who convinced me to buy Bitcoin initially as well. Was like Bitcoin's gonna be the, you know, the biggest thing in the world. He's like, I just put up, basically, all the money I have into Bitcoin. I was like, what the fuck? This is like back in two thousand, I don't know, sixteen, fifteen. Nobody was really saying that back then. So for the product market fifth fit thing, he goes. He goes, for example, I just invested in a company that's making a robot that makes pizzas. And it makes pizza it makes a perfect pizza every time twenty four seven at a lower cost than a human being can do it. He goes,

I don't know if they can because there's a ton of engineering risk. Like, they may not be able to technically do it. But if they can do it, there's zero market risk. Every pizza shop will want this over paying an employee to make imperfect pizzas,

only in certain hours, call in sick, and blah blah blah, like it for a higher cost. And I was like, oh, shit. That's true. There are things that have zero market risk. And I was taking, like, maximum market risk before. So, like, that's the other strategy. It's like,

You don't have to take as much market risk. The thing you're doing now, Greg, is, like, way less mark market risk. The thing I'm doing with Milk Road had, like, zero market risk, basically.

And there's just a, like, there's a lot of money. There's life changing money that could be made and a lot of fun that could be had without taking on unnecessary work. What happened to that pizza company?

I think they're still in engineering risk mode. They got like a big contract from Domino's, but then their CEO got just in trouble for some things that they hired a new CEO, something something something,

you know, like, again, these are legit engineering risks. So I'm not, like, that doesn't mean they'll all work. But, like, what I'm doing with the newsletter is, like, neither technical risk nor market risk. Yeah. An operational risk. It's just are you gonna are you gonna be able or wanting to do it for a long time? Which is -- Yeah. Which is good. -- that's a pretty good thing to try to overcome.

Right. Yeah. It's really tough. You know, I remember coming to San Francisco and and hearing all these narratives and these VCs telling me this. And also entrepreneurs sort of repeating a lot of this stuff.

And I will say it.

It's tough to go against

what

these stamps of approvals

say to do. You know? Like, you have to tell yourself every day, like and I have to do that too. Like, when I started a services business, all my most of my Silicon Valley friends were, like, a services business. Like, an agency,

that's what you're gonna do. Have to, you know, like and you just kinda have to push forward and and really just

remember that,

you know, just because some, you know, certain people on Twitter say a certain thing or or or Koya or and Reese and say a certain thing doesn't mean,

you can't have a great like, I would say you can have a better lifestyle not being Mark Zuckerberg than being Mark Zuckerberg.

Yeah.

Exactly.