The Ledger, every show

“I think playing entrepreneur is like spinning up businesses all the time, making all sorts of stuff, and giving it a name, and giving it a logo, and trying to raise money, and coming up with valuations, and talking about all this stuff, and there's like nothin…”

“You gotta get off the ground, and you gotta break free of gravity, but then there's a point where you actually just want to sit in orbit and sort of maintain. You want to be within a certain range and fluctuate a little bit up, a little bit down, but be in thi…”

“No options, no RSUs, no stock, no, like, any of that BS. I find almost all that to be pretty much BS, unless you're like a really well-established public company.”

“The moment they go raise money, they've cut off almost every option. They think they've expanded their experience and their opportunities, but they've cut off almost every possible off-ramp outcome because now they have to be in big business or they fail. That…”

“What's interesting is that Silicon Valley has found a way to make the most profitable style of business the least profitable. Like, software has, there's like, No physical costs. It should, the margin should be close to 80 or 90%, and it turns out that they're…”

“We don't have financial goals. We don't have OKRs or KPIs. I don't have revenue targets. I don't have growth targets in terms of the number of customers we need to pick up this year versus last year. I don't look at any of those things.”

“Promises are the downfall of every business. Like every time we've made a promise to get something out in a certain period of time, like, and we kind of inevitably seem to miss, miss it.”

“I don't like to look back on, on things. I'm not much of a fan of looking back on failures and trying to figure out what went wrong so we don't do it again, because I don't think we know what went wrong.”

“The moment you go out and take money, or have these big obligations, you end up working for someone else, and I don't really understand, I do understand why some companies do it, but I don't understand why a lot of people do it who probably shouldn't do it.”

“Ultimately about a third of the company quit in a matter of is it a week or two.”

“If I had to make it again today, I would make the same decision.”

“I can tell you the company's in a significantly better place.”

“This is the thing I think that's so important, and this is why, like, when we build products, we don't beta test them, really, and we, sometimes we get a few people in, but we're not, like, asking people what they think.”

“I have a hard time though sometimes with tech businesses that are quote successful or held up as successful examples of businesses that are actually fundamentally terrible businesses. I think like things like companies like Uber is an example.”

“Keep your costs low, keep your company as small as you possibly can and make great stuff. And then you don't have to find as many people just like you, but the ones you find really love what you do. And that's like, that's enough.”

“Well, like, a business is very simple. You gotta make more than you spend. That's a business, basically. Like, I mean, you can keep borrowing money, and then you can, you know, borrow more than you spend, and eventually you got to make more than you spend. So …”

“In software, you don't get that. Software can be anything. It's infinitely malleable. And what ends up happening is because there's nothing pushing back, it just expands forever and gets worse. Software slides downhill. It gets better for a while than slides d…”

“We're definitely leaving money on the table. I'm sure of it. Like, we don't optimize our pricing. I'm not testing pricing, not constantly. We're not A-B testing constantly. I'm certain there's some formula that we're not following that could lead to more growt…”

“We just recently left the cloud, left AWS, and we're running our own stuff now in data centers.”

“David wrote this great article about like getting off the cloud. It's going to save us something like ten million bucks and whatever it is.”

“The reason I don't like the postmortems in business, and I know a lot of businesses do this, they do, they launch something, they spend all this time and energy looking back on it, trying to figure out why it did what it did, and my general sense is you'll hav…”

“My job as a founder, what I've realized is, is it's to inject risk into the business. Most people, everyone pretty much at your company's job is to manage risk to some degree, to keep their job, to not push too hard or too far.”

“The chat itself isn't better or worse. Chat is chat essentially. Onboarding and bots were the thing. And we didn't have them and they crushed us.”

“Last year, we're like, we're gonna spend five million bucks for the first time ever on like ads. We started getting into it in a few months. So we spent a bunch of money and we're like, this is just, it just, It's vanity money because like this isn't doing any…”

“Never dismiss a good idea because of poor execution. And five people could have gotten it wrong in a row. It doesn't mean it's bad. They just may have gotten it wrong.”

“One of the ways to wreck new product development is to get too many opinions too early. Everyone's got an opinion, and especially when something's new, they're gonna tell you what they think, and then you end up having to sort of field and explain your reasons…”

“We don't offer equity to employees.”

“The ambition typically, or ambition is typically a word used to talk about, like, amassing, and collecting, and growing. You know, it can also mean, in my opinion, like, it should mean existing, sustaining. I'm ambitious at that level, but I don't need to go d…”

“There really is only kind of one outcome for venture backed companies, which is go huge. And if you think about all of the space between Kind of a small business and a massive, huge unicorn business. There's so much room there that you could normally find your…”

“We don't have any salespeople. You know, we don't have 15 different versions of Basecamp. You know, we're not after enterprise.”

“We build products with two people at a time. So every feature we work on in Basecamp or Hay or whatever we're building is two people, one programmer, one designer, and they have a maximum of six weeks to deliver the feature that they're working on. Most of the…”

“Airbnb is a physical product. Uber is a physical product. Basecamp, Monday, Asana, they're available everywhere instantly anyway. I don't know what you need the money for other than marketing.”

“We almost never, sometimes we look at numbers to sort of Be an input, but it's never like, prove that. I'll never say like, justify that. That's just not terminology or lingo that we ever bring up.”

“The idea behind once is David and I kind of feel like, we're probably a bit early here, but we feel like there's going to be a bit of a turn back towards the way things were. Pendulums always swing.”

“I don't want to be bigger and have much lower margins. I don't want to be bigger and lose money per customer. I don't want to be bigger and have to take a bunch of money to support that growth.”

“We don't have financial targets. We don't have financial goals besides being profitable. I'm not aiming for a certain percentage of growth on a given year.”

“One of the things we do is the first year is kind of a real big, I would say, I mean, people are hired, but it's kind of a test. The main question we ask at the end of the first year is would I hire this person again?”

“Frankly, like, most of my money is sitting in cash”

“I am exceptionally bullish on Clubhouse, more so than I've been about any company I've seen in a long time”

“I think six weeks at a time. I think six weeks ahead of time, And that's it. We're pointed in a direction, but it's six weeks at a time. That's the only thing I think about. It's the only thing I plan.”

“What I don't like about long-term planning is you kind of stop thinking. It's like you thought something and now you live it out.”

“We don't have, for example, we don't have shared calendars at base camp, so I can't see anyone else's schedule and they can't see mine. So I can't take their time and they can't take mine. If they want some of mine or I want some of theirs, we have to ask each…”

“So we don't have a roadmap. So we don't have a, I don't know what we're going to do. Actually, I have no idea what we're going to do eight weeks from now. I just don't know.”

“Every single one of them die. Often they kill themselves though. They don't change. They don't do something right. They don't pay attention to customers. They get cocky. They get greedy, whatever it might be. It's usually those things. It's not that's a compet…”

“And so like at our company, at Basecamp, we try to think, you know, the expectation is of eventual response, not of immediate response. And if someone doesn't get back to you quickly, it's because they're working. They're doing something more important than wh…”

“Make stuff for yourself. There's probably other people out there like you who want what you want, and make it available to sell. So you are the customer, you are the audience, it's you, and then there'll be other people just like you. We're not all that unique…”

“The more massive an object, the more energy it takes to change its direction, right? This is just like, this is getting back to basic physics. A thick, when I think of this stuff, and sometimes these metaphors don't perfectly line up, but in my head, I think o…”

“Our customers are small business owners, and I just, I don't care about enterprise customers. I don't want them. I like small, medium-sized businesses. They're more like me.”