Advice For 20 Year Olds Who Want To Make It In Silicon Valley

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 7 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. He 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 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 $2 billion 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 cut a 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 going to be big.

Exactly. Here we are, one acqui-hire later. Exactly. He's got the huge company.

Exactly.

Uh, there was so many of those. So in our masterminds itself, I think, uh, Loom was in there. That's a billion-dollar company. And I remember kind of like trying to mentor Shahed and being like, bro, like, you know, don't worry, you'll figure it out. 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?

Like, I missed, I missed, I missed. It was called, uh, what was it called? OpenTest.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. 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 want to make it in Silicon Valley, you got to give Laser focus. So I, you know, my mistake in my 20s 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 now, 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, uh, so there, there was like 10 examples like that. Like, uh, I remember Alex McCall came over one day and he, we were catching up and then he went on to start Clearbit. I remember thinking this guy's fucking amazing. Um, I should invest in this Clearbit thing. And I like went over to his office and we like hung out. I was like, got to meet the guys. I was like, I love the 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. That's also like a, I don't know, I dunno if it's a billion, it's multi-hundred million dollar company.

Dude.

Um, and he told me at the end, he goes, oh, by the way, I'm buying up, uh, I was like, what else are you doing? Finally I started to ask smart questions. I was like, what else are you doing? He's like, oh, I bought up some Stripe shares. There's Stripe shares available for like $2 billion. 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 Stripe shares for $2 billion. Let me know if you want in. And I was like, $2 billion to me. I was like, well, that's like the most a startup is worth is like a billion is like 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 Stripe shares at $2 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 Stripe shares at $2 billion now, like, it's like, that's already like, like 100x, you know, from, from there. And that was proven, right? Forget that. Then there was all the services we were using, like Furkan, 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 PagerDuty and Elasticsearch and so, you know, like one after another, those were all huge winners that were pre-IPO. Um, so first was investing. The second was like project selection. So like you were 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 in Silicon Valley was to be like a product guy who was building, who had like cool product taste and was building like, um, 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 how I felt about it. Right. Then Sam's company sells for more than, more than my company sold for in the end.

He goes, uh, 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, 'Uh, that's a great analogy. That's a cool story. But like, uh, I don't know, man. I think the math kind of— I think it might achieve the desired outcome, which I'm trying to do here.' Which, uh, when I started, I was just trying to be financially independent by the age of 30. That was the only goal.

Um, and so, so like if I could go back and just whisper 3 things about like just strategy, just strategy, like forget life advice, just strategy advice, I would've said, um, 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. That would've been the first thing. The second is invest in all of the expenses on your P&L. So go find all the places you're spending money and go try to 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 want to do your own company beyond that, fantastic, that's great. You're going to build up skills and you got 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 just 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 a good opportunity, which by that time is pretty late. 'Cause what's the VC doing? They're looking at what companies are raising huge rounds, which means like 4 years ago those were great opportunities. 3 years ago those were great opportunities. And so I wish I had just kind of been more eyes wide open on like what projects are available to you and like the things that sound kind of nation funny. Those are actually better signals for you than the thing that the VC is saying is going to be huge or is already huge. Because it's often, um, you know, those companies to start are like, you're in a, you're in an absolute dogfight and it's just like one winner out of 100 is going to emerge versus other things where like you could basically take, um, no, no product risks, uh, no market risk. So I had a friend Vishal tell me this once. 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 fit risk. He goes, no, it's not. Like, what? And he goes, he was the one who convinced me to buy Bitcoin initially as well. He 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 2016, '15. Nobody was really saying that back then. So for the product market 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, 24/7 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 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 is like you don't have to take as much market risk. The thing you're doing now, Greg, is like way less 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 risk.

What happened to that pizza company?

Uh, I think they're still in engineering risk mode. They got like a big contract from Domino's, but then their CEO got was 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. Operational risk. It's just, are you gonna be, are you gonna be able or wanting to do it for a long time? Which is, yeah, which is like, you know, 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? You know, like, and you just kind of have to push forward and really just remember that, you know, just because some, you know, certain people on Twitter say a certain thing or Sequoia or Andreessen 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, yeah, exactly.