I Asked a $450M VC Where to Invest in 2026
My First Million
Hubspot
4.7 • 2.9K Ratings
🗓️ 3 March 2026
⏱️ 59 minutes
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| 0:00.0 | I could only lose three million bucks. |
| 0:01.7 | I could gain 300 million bucks. |
| 0:03.8 | I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On a road, let's travel. Never look. All right. What's up, dude? Not much, man. Doing well. Dude, always good having you on. You are, as always, I give you this title, the most interesting man. In tech, you're a great investor. |
| 0:23.8 | You're a tech investor. |
| 0:24.8 | How about that? good having you on. You are, as always, I give you this title, the most interesting man in tech. You're a great investor. You're a tech investor. How big is the fund or how much total have you invested now at this point? About $450 million total. Okay, $450 million. So like, you know, I've learned a lot from poker, right? And in poker, you learn all these lessons that actually cross-apply totally outside the domain of poker. What would you say with the lessons from investing |
| 0:40.5 | that apply to life? I think, you know, one is just like, upside can be greater than downside. |
| 0:48.9 | Like, so if I invest in a company, let's say I put $3 million into a company, |
| 0:56.6 | there is a possibility of it being $300 million. But the downside is capped at $3 million. I could only lose $3 million. I could gain |
| 1:03.8 | $300 million. Yeah, because if you don't work in investing or anywhere where you have that |
| 1:08.8 | sort of asymmetric risk versus return, let's just say |
| 1:12.7 | you have an hourly wage job, right? Like, your mind gets trained into this linear. I put one in, |
| 1:17.6 | I get one out, right? Like, I can't put one in and get 50 hours of pay out of this next hour. |
| 1:23.4 | That doesn't really ever happen in a normal job. But if your job is investing, you're like, |
| 1:27.1 | of course, that happens all the time. I lose one times my money, but sometimes I gain 100 or 1,000 times my money back. And that kind of breaks the brain and you sort of like start to see, you know, other opportunities. Similarly, they have that, as they say, the asymmetry of risk return. All right, so that's one. There's something around just portfolio theory. like, you know, out of the 450 million you deploy, right? Like, what does, what does winning look like? You probably need to return some multiple of that 450 million. So what does winning look like for you? You put it in 450. What do you need to get out for this to be a success? A couple billion dollars. A couple billion dollars. Let's say two billion. Let's just use it. There's a rough back. Let's say it's 500 million to make a math easy. Right. So 500 million, |
| 2:04.3 | 4X, |
| 2:04.8 | it. There's a rough math. Let's say it's 500 billion to make a math easy. Right. So 500 million for exit, that would be great over some 10-year period. Yeah. Now, of that 2 billion, how many companies would you go into? And of those, like, how many companies would be responsible for returning all of that money? It's only going to be a few, right? Give me the |
| 2:17.7 | math there. Yeah. So almost all of the returns are going to come from like 10 companies |
| 2:24.3 | out of hundreds that we will have invested in. Correct. And so there's something like that in life too, |
| 2:31.3 | right? Whether it's like people you meet or dating or like there's some portfolio theory, some power law where the few will drive like all of the joy, the value, the relationships, the opportunities, whatever. And then you just do the rest because you need a portfolio in order to find the few that are like the big outliers. |
| 2:48.5 | It's true. And it's also, it's also in a related note, there's like, if you increase the surface area of companies you meet, |
| 2:56.7 | you have the better odds of finding that one, like where you really know it's going to work. |
| 3:02.1 | And so in life, I think increasing surface area is good, like saying yes to stuff. |
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