The Ledger, every show

“This idea of making a startup, a Silicon Valley-style startup, the concept has been engineered to benefit top-tier VCs.”

“A sign of, like, a non-serious business is when people in it say this is a relationship business. This is a sign of, like, it's immature, and it's not professionalized.”

“So I think over the next, like, five years, this, like, alleged entrenched data advantage of big companies will turn out to be, you know, a big nothing.”

“Because the average expected return for founders of making a startup is sharply negative.”

“I've never cared about discovery and about distribution. I think, like, the best stuff gets discovered automatically.”

“The incentives are when you're investing, especially if you're doing early stage investing, just like me, you're not looking for things that are likely to succeed, right? You're looking for things that have a plausible chance of succeeding, even if it's not a …”

“And for mm-hmm, since I think this is a multi-trillion dollar thing that's happening right now, I think mm-hmm needed to get pretty big, pretty quickly, raise external capital, and so it was a perfect thing to say, okay, yeah, embodying this in a spin-out star…”

“So never hire someone whose job you can do better than them. Only hire people, only surround yourself with people that are ridiculously better than you or that are superior to you in their job or other things as much as possible. Like always be the worst perso…”

“When you hear a pitch, you get excited about what you would do with this idea. And that's a really shitty way to make investments because you're not going to do anything with this idea. You got to try to figure out what they're going to do with this idea.”

“Integrating video into everything in this hybrid model is going to literally affect almost a hundred percent of all things in life. It's going to be a bigger transformation as the dot-com transformation was, except it's not going to take 10 years. It's going t…”

“Most boards' conversations are totally stateless, meaning that the board members walk in, and they don't remember anything that you talked about before, and you start over. And this is the most frustrating thing for entrepreneurs, because, of course, like, you…”

“So my guess is about 50% of what we use as consumers will become conversational, botified, and about 80% of what we do at work.”

“I think it's a major point of disruption. I think that the single biggest change is going to be for the past few decades almost all of our interactions with technology have been one person interacting with some system. So it's been like you using Microsoft Wor…”

“One of the many things that are wrong with startups is startups are all about shortcuts. All of the incentives are to take as many shortcuts as you can. The biggest shortcut that you can take is just hiring your friends”

“Like, it is your failure if you have not hired people that you think are better than you at their job.”

“There are no points for following instructions. There's only points for succeeding, for doing the right stuff”

“I just haven't had good success with like reviews that felt more useful than harmful.”

“And obviously, within a year, like, this isn't what video is going to be like. Obviously, It's going to be the next generation of like native to video companies that comes along and says, well, no, we're not trying to recreate the old reality. We're not trying…”

“Exceptional talent, like, Mozart-level brilliant, exceptional talent is very, very rare in the world, but it's evenly distributed, and, but opportunity isn't, and so it is bad for the world that so much of the opportunity for crazy, exceptionally talented, cre…”

“For the most part, a good idea one year is still a good idea, regardless of whether the market is up or down.”

“I think that my two year inadvertent vacation in venture capital, I think has probably made me a better CEO than any actual time operating a company.”

“Silicon Valley, the actual geographical Silicon Valley, and basically San Francisco, and, you know, the area between San Francisco and Stanford is, I think, less important than it's ever been for tech and for innovation.”

“Like it doesn't make sense to take brilliant product people and force them to become mediocre CEOs before they can actually make that product.”

“So the vision is, you know, in five years, we'll be in eight different cities. We're in three. Now we're opening up the fourth one next year. We'll be in eight cities, eight world cities, each one working on a number of very practical products that solve real …”

“When things are sharply going wrong, it's actually the part of the job that's, in many ways, the simplest, because you know what you have to do, and then you just do it. And you have like, you have one major objective. The objective is clear. And even if it's …”

“There's going to be a couple of hundred famous bots in the world, and everyone's going to know them, and everyone's going to be able to interact with them, and they're not going to be, it's not going to matter what directories are listed in. They're just going…”

“My entire long-term investment hypothesis is really straightforward. Like, I think the world has two possible futures. Like, there's two directions that the world can go in. The world can become more like Star Trek, or the world can become more like Mad Max. E…”

“I mean, for businesses, you pretty much, it all comes down to the same tool, which is money. So if you're not spending money on it, you're not serious about it.”

“So we spend money on recruiters and we specifically tell recruiters that we are paying you money to send us people that are outside of our comfort zones and outside of our networks, because we know plenty of, you know, middle-aged white dudes.”

“I don't think it was a very good VC.”

“Just because I believe something strongly doesn't actually make it any more or less likely to be accurate or true than if some random person in the street believed in it strongly.”

“When we went from being in person to doing all of these things, you know, we no longer do brainstorming in a big conference room with, you know, stick stickies, post-it notes, you know, now we do it all on Figma, and actually I started noticing, man, I'm just …”

“Like, real talent is exceedingly rare, you know, one in a million. But it is evenly distributed throughout the world.”

“You have to make sure you have the right people and you have to make sure there's enough money in the bank. Those are the three things you have to do. No one else is effectively going to do them. It's always those three things. Anything else you do is kind of …”

“And I think the kind of towards the end of my stay at Evernote, you know, I basically decided that I needed to replace myself once we gotten, you know, it's about 400 people that just felt like I just wasn't the problems that needed to be solved at a medium si…”

“The core job of a CEO is just to, like, you just have to repeat yourself over and over and over again. You just have to say the same thing for what feels like literally a thousand times, even though it's may only be a hundred times, but it's the constant over …”

“I'd kind of stopped sitting and I stopped doing email almost entirely. Like for the past few years of my life, like I had very, very slight contact with email”

“The stuff that we're working on, the stuff that I'm investing in or helping to build, it's all like the, these are bots that do specific functions that people pay for.”

“A really quick one is I don't work on airplanes. I made this arbitrary rule where I will not work on an airplane.”

“It started as a joke, just as a way to make our life on video a little bit less boring. So we just started goofing around with backgrounds and pictures and things you can do in Zoom, and pretty soon it became a product.”