Jeff Bezos

`2:39:41`

is to get to a billion dollars or more. Now the path to that usually does go through running established playbooks and then when it comes to software, the enterprise sales playbook is that playbook. If you're doing B2B software SaaS, you will try to find product market fit. And the second you have it, you will abandon your small and medium sized accounts to chase the big whales with a huge sales force and by then you're a thousand people and life sucks. — That said, I mean people are just curious about this. I've gotten a chance to get to know Jeff Bezos. He invested in Basecamp, not controlling? — He bought secondaries. So this was the funny thing is that when investing have these two dual meanings. Normally when people think about investing, they think you're putting in growth capital because you want the business to hire more people to do more R&Ds so they can grow bigger. Bezos didn't do that actually. He bought a ownership stake directly from Jason and I,

`2:40:44`

and 100% of the proceeds of that purchase went into my and Jason's bank account, personal bank account. Not a single cent went into the account of the company 'cause we didn't need the money to grow. What we needed or what we certainly enjoyed was to some extent maybe the vote of confidence, but more so the security of taking a little bit off the table is that we dare turn down the big bucks from venture capitals. It was essentially a vaccine against wanting to take a larger check from people who then wanted to take the company to something enormous that we didn't want to go with it. So Jeff gave Jason and I just enough money that we were comfortable turning all these people down in a way where if it had turned belly up like six months later, we wouldn't have been kicking ourselves and going, we had something here that was worth millions and now we have nothing and I have to worry about rent and groceries again. — It is a vote of confidence.

`2:41:45`

I wonder from, I'd love to hear Jeff's side of the story of like why, 'cause he doesn't need like the money. So it's really, I think it probably is just believing in people and wanting to have cool stuff be created in the world and make money off of it, but not like. — 100% the motivation for Jeff wasn't a return, because he actually has a team. He's private office that runs these investments who did the calculus on the investment pitch we gave him, which was so ridiculous that Jason and I were laughing our asses off when we were writing down our metrics. I was like, no one's gonna pay this. No one is gonna give us this multiple of this amount of revenue. And that's fine. I mean we took the call essentially out of kind of an awe that Jeff Bezos even wanted to look at us and like, do you know what? We don't want venture capital. We don't need other people's money, but like let's just give him a bullshit number that no sane person would actually say yes to. And then I mean, we can each go our own way.

`2:42:48`

And his investment team said like, "Jeff, no way. This makes no economic sense at all. They're asking for way too much money with way too little revenue." And Jeff just went like, "I don't care. I wanna invest in this guy." Because to him at the time it was chump change, right? Like Jason and I each got a few million dollars. I mean whatever the currency swing between the yen and the dollar that day probably moved 10 x that for his net worth than our investment did. Jeff seemed genuinely interested in being around interesting people, interesting companies, helping someone go to distance. And I actually look back on that relationship with some degree of regret, because I took that vote of confidence for granted in ways that I'm a little bit ashamed of over the years I've been more critical about some of the things that Amazon had done that I feel now is sort of justified. So that's just sort of part of that processing of it. But on the economic sense, he gave us that confidence.

`2:43:48`

He gave us the economic confidence, but then he also gave us the confidence of a CEO running perhaps at the time the most important internet business in the US. Showing up to our calls, which we would have with him like once a year and basically just going like, yeah, you guys are doing awesome stuff. You should just keep doing awesome stuff. I read your book, it's awesome. You launched this thing, it's awesome. You should just do more of that. I don't actually know how to run your business. You guys know it. — So the book goes out. I'm just so, from a fan perspective, I'm curious about how Jeff Bezos was able to see, 'cause to me, you and Jason, like especially humans in the space of tech. And the fact that Jeff was able to see that, right? How hard is it to see that? — He certainly saw it very early. And I think this is something that Jeff does better than almost anyone else. He spots that opportunity so far in advance of anyone else even opened their eyes to it, or certain he is willing to bet on it far early and far harder than anyone else is. And he's just right time and again. I mean, we were not the only investment that he made.