Lessons from DHH and Jason Fried


“There’s a better chance of winning the more bets you place (to some degree).”

“Remember to ship. It’s got to be made real.”

“The way to figure out if the idea is any good for the market is to make it and ship it, and then you’ll find out.”

“Way to stack the odds is just simply to build more. Creativity is a regenerative force. It’s like a muscle. The more you use it, the more you will get out of it. And I think that’s the misconception some people sit with, is that they kind of have to conserve this creative energy. Oh, I got to make sure that I have just the right idea at just the right time before I start building. Nonsense. Just start building. And you know what? Maybe this idea isn’t the right one, but in the process of building, your neurons will be firing at a greater frequency, and that will make it more likely that you will come up with that great idea.”

“You have a better chance at judging the idea if you make something, you’re going to use yourself. It’s quite a bit harder, I think, to build something on behalf of somebody else and know if it’s really any good. It might be good technically, in some ways, but if you don’t really have the problem and you can’t really feel around the problem, you’re sort of solving problems by proxy, and it just becomes harder. So I think you can stack the odds in your favor by making something that you need.”

“This is the luxury you get when you run a company well enough that it has spare capacity, that it has slack for you to chase adventures.”

Great business ideas do not make sense initially

“Very smart people can convince themselves that if they do a really rigorous analysis on some opportunity, they map out the total addressable market, and they do all their little positioning and they do all the rational things. They try to look at all the signals that they can quantify and they put them into their little model. […] You know what? If we put good stuff into the universe, it’s going to pan out. Do I know exactly how? No, I don’t.”

“This idea that everything has to be broken down by some sort of specific analysis because that kind of analysis feels very intellectual, it feels very rigorous, it feels very businessy, but it’s very narrow. It can only deal with the things we know, the things we can quantify. And so much of success in business relies on the opposite of that. Everything that can be quantified. How many users are going to buy the thing that they don’t even know exist? I don’t fucking know. No one knows. You have to put it into the market. You have to see how they react to it. And I think this is one of those lessons where you kind of have to let go, and that’s very difficult for, I think, smart, rigorous people sometimes.”

“Look at the history of business and go like, how did most things start? Did Phil Knight selling sneakers out of the back of his van have the vision, the roadmap, the plan already for this mega corporation? No, he didn’t. Did Jobs and Wozniak have it when they were putting together their little freaker sets? No. Or Airbnb. The pitch was what if you want someone to sleep on an inflatable mattress in your living room and a bunch of investors looked at that and said no, no, I don’t think anyone wants that yet. That’s what became this huge thing. Most good ideas that end up blowing up, they cannot actually be analyzed rationally upfront because if they could, someone already would have. You would have gotten the rational market hypothesis already working it’s way through the obviously good ideas.

“Take this leap of faith. We’re just gonna try things that feel right. You can also embrace that while still being like a hard nosed business person who wants the bottom line to exceed the top line. They’re tools, but you should have them and you should run a good business. And then you also have to find a way to bridge that paradox that most of the things that end up panning out and becoming huge they don’t comply to that, they don’t comply to that analysis. “

“We don’t try to reduce everything to a cost benefit analysis and that the overall picture has to be a healthy company that can meet its payroll and then some have plenty of slack.”


“Marry this sense of quality with a sense of urgency, with a sense of proportionality, and successful entrepreneurs are able to sort of straddle all of those three things at the same time.”

“Sometimes you just put too much weight on the wrong foot and they’re like, no, actually, if you stand a little different, you’ll have much more leverage and you’ll be able to do it much easier.”

“If there’s no uncertainty, there’s no adventure.”


  • https://37signals.com/podcast/a-matter-of-ambition-part-2/
  • https://37signals.com/podcast/a-matter-of-ambition/
Written on May 16, 2024

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