The Ledger, every show

“They won't be poets, because AI will show people that that's all kind of a BS thing that we just did at a period of time, and, like, people actually don't like making art and poems if there is no monetary or fame attached to it.”

“Twenty million in revenue. We have 35 people working like this. We do, you know, eight or nine million in net income. And yet still we have no full-time employees. Like I'm not interested in hiring a single full-time employee.”

“I want to get Gummer to a place where the average person works like an hour a day. Maybe they make like 800 dollars an hour but they work like an hour a day. They're producing an hour, you know, 800 plus dollars of value. They're assisted with AI to write thei…”

“I would love to be able to buy a house in San Francisco, you know, for 200,000 dollars, and I think that's possible. But it's gonna take, you know, 10 plus percent interest rates.”

“Like I can make Gumroad every weekend, which means I can make a new company every weekend, and that company can probably raise money at a 10, fifteen million post money valuation.”

“Obviously Elon doesn't work at Tesla and SpaceX at all, and those companies are doing decently well, even though he's technically still the CEO of both of those companies, right?”

“100,000 software engineers can run the world. Like we don't need a million. We don't need ten million. And we'll, by the way, never get them anyway.”

“I totally think you could run like America with like, you know, like a few thousand people. With software again”

“Like in the instance that Elon didn't know how to code, Tesla would have died. You know, in the instance of Naval knowing, not knowing how to code, AngelList would have died.”

“Gumroad, it took me seven, eight, nine years to get to a place where Gumroad kind of is considered, like, you know, we're at ten million in revenue doubling every year, but that's because of a macroeconomic shift, namely COVID, that just happened out of the bl…”

“Frankly, if I could go back in time, I would have said no to them. I would have given that 400 K a hundred K to four different people, super angels or angels, or even split it further.”

“I think career investors are just not as valuable because frankly, like that sort of on the ground experience of building distribution, building a product, That stuff is just so difficult to read about. You just have to do it to really grok it.”

“Basically it's a GitHub repository that, you know, sort of is the source code for a website and a bunch of 10 99 contractors, freelancers work on it. And they do it just like they would work on an open source rails or something like that project where they're …”

“People can earn equity in the business as well. So they can choose to take their hourly rate and convert up to 80% of their cash into equity. And then that equity entitles them to dividends, cash flow in the business.”

“Like engineers are cheaper. They're easier to hire. Designers are cheaper, easier to hire. And that's all I need. I don't actually don't need anything else. Those are the two most valuable, you know, resources on the planet. And now they're, you know, they're …”

“Basically any job in which your output is digital you know, I see that, that, that will kind of be replaced with basically a computer predicting what that human would be outputting.”

“A startup like Gumroad or really an indie developer can now compete with YouTube on YouTube recommendations, which four years ago or even two years ago would not have been the case”

“People think all of these other jobs are getting automated away, but the number one job that's getting automated away is actually the software engineering job, right? Like why is software engineering such a valuable skill? It's because we've automated the crap…”

“We will, 100% basically be able to, you know, get rid of pain probably, you know, short circuit depression, like, all these sorts of things we will be able to do without needing to know exactly what, you know, we'll know the math, because you can look into thi…”

“Any privilege associated with anything else, height or body mass or, you know, fast switch muscle fibers basically is not going to matter a hundred years from now.”

“I could a hundred percent see that like 10 years from now, there's no way to make money in AI, right? Like basically nobody made any money on AI. All the returns basically just went to, you know, whoever like basically gets attention so that they can monetize …”

“If you look at startups and you say, okay, 99% of the public value is basically, or 90 plus percent is basically in four or five companies. Right? If you get rid of, like, Google, Amazon, Meta, like, we haven't done shit as an industry, right? In terms of actu…”

“And the truth is, if you can't write it, you don't actually understand it. So you can pretend that you get it. But the truth is if you read the Bitcoin white paper and you haven't actually implemented it, you don't actually understand it. You don't actually un…”

“Like, I can build Gumroad in a weekend and I can outship basically any, it doesn't matter how awesome your team is, if it doesn't have engineers on it, I will beat them. Right? I would just, I will win.”

“How many hours a week at Gummer do I work in front of a laptop? Zero, basically. I don't, like, I don't type. I generally just respond to messages on, on Slack and Notion, and this is what most CEOs do.”

“I can't think of a single example of someone who is non-technical, doesn't have any interest in knowing how to code, and has built a ten billion dollar company.”

“Most people with TS degrees don't know how to code, you know.”

“The goal is Gumroad, for example, we have zero full-time employees.”

“If you are on holiday and you're like, I love being on holiday. I'm sorry to say that, like, you know, doing a startup is probably not for you, right?”

“You need to be growing in the article, I say, 20% month over a month, but it can be 10%. It just needs to be sort of exponential or so. Or polynomial or whatever the correct math term is. And if you're doing that, you can stay on this path. If you're not doing…”

“Yeah, I think Reid's quote was accurate maybe 10 years ago when he probably said something like that, but the truth is the bar for where your product needs to be today is so much higher, and yes, you should be embarrassed because I think the best founders will…”

“We're never going to see hundreds of billions of dollars in rolling funds, in my opinion.”

“If you see a lot more interesting companies, you might actually see a depreciation or sort of a depression in the prices and vice versa.”

“VCS want their same rough allocation, and that roughly means that a founder's gonna get hit with the same dilution if they're raising a million bucks, or five million bucks, or thirty million bucks, frankly, right? Everyone wants their 10, 15, 20, 25%, dependi…”

“Frankly, the number one reason I pass is the founders. I just, I'm not impressed by the founders.”

“And that was when I learned, like, oh, like, growing 60, 80% a year, you know, series B is not, like, that was not good enough.”

“What is a billion dollar company? Right? Like, it means like the last share you sold for like, 11 dollars and you have like a hundred million of those shares out there... And you can like, maybe if you're lucky, get a loan on it or something. Right. But at the…”

“We updated the charter so that basically I could run a dividend at this sort of 60% annual net income rate without their permission.”

“Like I always thought it's weird. Like founders are like, oh, like raising money for VCs. Like I hate VCs. It's like, if you're raising money, like you should respect them. Like they're smart, you know, like if you don't like find better ones, like they're goo…”

“20, 23, we'll do 60% of our net income. So we'll do about eight or so million in net income, and then we'll dividend out about six or so million.”

“And the way we manage flexibility and freedom at all costs is I just say, hey, this is what I think we should get done this quarter. This is what I think feels reasonable to me. And then we kind of backfill, you know, people say, okay, I'm going to work on tha…”

“And what you get out of hourly, just like Uber, just like Airbnb, just like instances on AWS, you get efficiency. You get much better utilization of these assets.”

“All this AI stuff will, like, the whole designer-engineer split seems weird to me too, to be honest, because, like, the designer is really having to, like, write code now and then the engineer, like, it's, like, actually really, like, everyone is a designer.”

“They'll definitely be less, less builders. As a percent, it'll go up, right? Because you're going to see tons of people who don't identify as builders leaving the ecosystem. I consider these people like tourists basically who got in when it was like really sex…”

“Most builders are not risk seeking at all. Right? So when you look at founders, like the founder personality type, you have to overlay so many things that are like in the minority to get someone like a Patrick Collison or a Dylan field or a Mark Zuckerberg or …”

“I don't think it's as notable as people it's, I don't think it's a step function increase. For example, I think we've been basically seeing this gradual thing happening, which is we take work that is valuable, but wrote and automate it.”

“My guess is 1015 years from now, we'll start, you know, we'll, we'll be watching robots play soccer instead of humans”

“Certainly the number one, you know, thing you could do to kind of invest in and make money, frankly, is to invest in people who know how to code because those people are the most leveraged people”