Entrepreneurs at work

“and got the money he needed to start the company. And then fast forward to 2013, which the excerpt in the Wall Street Journal of your book tells the story of a birthday party for Elon Musk, replete with all kinds of costumes and strange things and fake battlements. But this is perhaps, apart from the founding, the most crucial moment in DeepMind's genesis as a company, right? Yeah, that's right. So, you know, by this point, Demis had raised three rounds of venture capital, including from Elon …”

“like be honest no and i think it being delivered from you who's actually done all of the things and built your way up and built real companies in lances again love social media no shade on these people but if you're a 27 year old life coach that went viral one day now as a platform i'm less inclined to take you seriously yeah and i think like it's it's you i think people are looking for real examples of people who've come up the hard way and have done the things i like i think in it what i …”

“because i know my personality i don't take breaks so i actually had a goal it's simple but i said i will do nothing for the next six months i'm going to challenge myself to do nothing for six months. Did you manage? I did it. I did it. I did read a lot. I exercised. I went on long walks. I did multiple meditation retreats But that was my challenge to myself to not work for six months So after six months of successfully doing nothing after setting yourself that goal what did you do to figure out …”

“emotion-based stuff of you've done a billion dollar exit, my friend. Most people have never done that. Walk me through that experience of what you wish you knew when you were building the org from the beginning versus what you were doing now like okay god this would have made this exit more achievable and faster if you had done these things for sure in kind of the the moment that we rang the new york stock exchange bell is just like a pinch me moment for anyone. I remember going to college and …”

“Mm-hmm. Yeah. Or wasn't it dye to match the band Perry's blonde? Oh, no. I can show you evidence. I good I believe you No I met Johnny in October of 2020 in Dallas because Irene and I were working on some music down there and I just immediately fell in love with him And I can tell you he was that blonde. Very platinum. But he used to, he was not wearing leather as much then. You were wearing Carhartt overalls without t-shirts. Where are you from? Grew up in Dallas, Texas. Yeah. But mostly like …”

“that. But when we sat down at the first meeting, the person we were sitting across was like, what are you going to do for the company? And I was like, oh, no, I'm pregnant. I'm just here to afford him. And she was like, oh, no, no, no, no, no, no. You're a part of this. And now I run the company and the scouts on permanent furlough. He's on permanent furlough. I admire the fact that you can work with your husband because like I sit next to my husband in our shared office. We don't work …”

“I guess we wanted people to never have to, like we wanted Granola to work everywhere. You shouldn't have to think about, oh, can I use Granola for this meeting or should I use Granola for this meeting? It should just work like wherever you're having a conversation. uh we're interested in like at the beginning actually we were really we thought notes is we're just going to get notes that's all and we toyed a lot with should we even show the transcript or should we should the transcript …”

“And that was a lot of fun. And Think Unlimited is one of the coolest companies I believe in home improvement. We have the most advanced AI. I partnered with a buddy of mine who actually sold his company to Empire. He used to have Galaxy. Well, no, that was his other home improvement. I can't remember the name of his company right now, but there was just an awesome opportunity to partner with someone that had built some technology for home services way back in the day. And so we built this …”

“And so NSF, it's taxpayer funding. So the government at least is not supposed to be funding businesses directly, although sometimes they do. But there was formal legal restrictions on funding things with commercial applications. And so what there was is there was something called the AUT, the Acceptable Use Policy. And the Acceptable Use Policy said that basically the internet, NSFnet turned internet was for academic and research use, and commercial activities were strictly prohibited, like …”

“I called Sam into the office and Steve, I'm like, no, Sam. He was there. Steve was at studio working there. And I said, hey, Sammy, come here. Want to see something cool? He's like, yeah, check this out. And I pulled up my computer screen. It was not many thousands in there. And we had, you know, a huge nut to cover. We're halfway through the month. And he just looks at me and I'm just like, oh, that's our bank account, huh? I'm like, yeah, pretty much all the money we have. I'll share. We had …”

“I can't A-B test my life and say, Chris, if you just want to focus on that one, who knows? There's too many variables. But what I do know is that I don't want to report to a board. I don't want a bunch of shareholders. I don't want to take a company public. I don't want to be in meetings all day or Zooms all day. I don't want to be away from my family. And to build a billion dollar business, I feel like I would need to do those things. And what's the biggest business you currently run and how …”

“So, like we discussed, I sold Reportive to LinkedIn, and at the start of Superhuman, I think somewhat irrationally, I wanted that baby back because, you know, to your point, Jason, it could have probably, maybe could have been a billion-dollar company. Who knows? It was, let's say this, it was certainly beloved. If you were in Silicon Valley at the time, you used that product. We, it turns out, had I known this, we would have sold for a lot more money. We basically had every single daily active …”

“I tweet about them. I get information back in the process. I see your work. I see your work. I see a bunch of folks and try and incorporate that back in the box. My job is to try and connect all these things together and make it useful. And you're the number one spokesperson, right? So you do have to be out there. Yeah, but I kind of would be doing it whether or not... It's like I don't really think of it as a job requirement as much as like I just like social media. You're so good at it. Yeah. …”

“Building this media company, so to speak, has been the hardest thing I've ever fucking done in my life. If you knew what you were going to have to go through day one when you started this to get to today, would you have done it? No. I would have stayed in corporate America, made 300 grand a year and just been completely happy taking vacations whenever I wanted to because we had money to do it and lived like a robot. I'm going to tell it to everybody right now listening. Yesterday was a very …”

“I want to have a little extra money. I want to blah, blah, blah. And that's all great shit. That's like your foundation. That's the shit you have to have. Okay, but that's not the win, bro, because now you have all this knowledge. Now you have all these skills and now you have these relationships. Now you know how to execute And if you stop now you going to feel like a failure your whole life regardless because you going to always ask yourself what could I have been had I actually committed So …”

“Right. You don't have to be on a rocket ship every time you start a business. That's not the point, at least not to me. Right. So you just have to think about what you want your company to be and what potential does it have. With TaskRabbit, I always saw a vision of the world where the future of work was changing. The gig economy at the time was nascent. It was not a thing. We really helped create the gig economy along with other companies. And so for me, it was like, this is a venture-backed …”

“The co-founder of HubSpot came on this podcast and he talked about in his first company, he was making everything up. And his second company, he said, oh, now I know how I'm going to do everything differently. And it totally failed. And he goes, just because I was ignorant doesn't mean I was wrong. And there something to that idea of like you can be both ignorant and correct I go so far as to say that ignorance is a benefit for a huge class of problems That you are cursed when you've been …”

“So wait, wait, 100% you're going to put in your own company? Not 100% because I think for the next venture, I will most likely raise money just because now this is kind of like my nest egg. I never need to worry about it. I'm definitely willing to like take risks. But how much? What percent? Like in your head, you're thinking, let's say hypothetically, you have $10 million. What percent do you want to put in your new company? Yeah, well, I mean, maybe this goes to the EV question a little bit, …”

“Just to underline that a bit, Anthropic says its run rate revenue has hit 14 billion dollars, growing over 10x annually in each of the past three years. And Claude Code's run rate revenue has grown to more than two and a half billion dollars. We are, folks, seeing revenue in some of these places. Go hockey stick. Here's another data point to that end. Also from CNBC, Cohere hit roughly 240 million dollars in annual recurring revenue last year, surpassing its 200 million dollar target, according …”

“market news here. So Polymarket, which is the leading prediction market platform, acquires Brahma if I saying that right B to scale blockchain trading infrastructure So we know these platforms are very disruptive And in fact you know the crypto industry is facing a lot of battles from incumbents You got the banks”