As part of my involvement in the Edmund Hillary Fellowship, I've been conducting office hours sessions with a handful of New Zealand-based entrepreneurs. These are typically 1-hour calls focused on a specific struggle they're having. Questions typically revolve around remote work, marketing, differentiation, hiring, messaging, product ...

Everything you've heard is fabricated, manipulated, or exaggerated. It probably didn't happen that way. The way things are, likely aren't. It wasn't because of this, it was because of that. The longer its been since it was said, the less likely it's still true. It didn't start there. The founding quote is misattributed. That's not why ...

A core tenet of how we work at Basecamp is that we make it up as we go, 6-weeks at a time. No big plans beyond that. We have some big picture directional ideas of where we may be headed — like a sailor on an exploratory expedition, aiming for a distant shore — but we're tacking with the prevailing winds, and our whims, until we eventua...

Sometimes I get asked a direct A vs. B sales question. Like... "Why should I buy HEY instead of Fastmail?" My honest answer: "I don't know. You should try both and see which one you like best. And once you've made your choice, I'd love to hear which one you picked and why." I'm not selling, I'm learning. I can surely point someone to m...

I've got two young kids. Because of the pandemic, a good portion of their outside experiences have been masked. I think this is ultimately to their advantage. Much of our emotions, reactions, and communications come from the bottom halves of our faces. Our noses, cheeks, and mouths express so much of what's on our mind. The shapes, con...

Traditional search engines like Google are pretty good at helping you find something specific. Like a research paper on a clinical trial, or a picture of Wrigley Field, or a product if you know the name. If you kinda know what you want, and you'll recognize it when you see it, there's a good chance that stodgy old search engine will he...

Spend enough time talking with entrepreneurs, product people, designers, and anyone charged with proving something, and you’ll bump into questions about validation. “How do you validate if it’s going to work?” “How do you know if people will buy it to not?” “How do you validate product market fit?” “How do you validate if a feature is ...

There's so much energy spent on trying to convince someone to do something, or buy something, or change their mind. It's all possible, but it's the hard road. Instead, I tend to try to get people to naturally nod their head in agreement. Whenever I write something with the intention to explain, sell, or promote, I'm aiming for head nod...

Businesses love to compete. To beat, to win, to go 1-0. We don't. I have no interest in competing with anyone. And we don't frame internal decisions in a competitive way. Business has never been about competition for me. Market watchers may think HEY competes with Gmail, but we don't think that way. Gmail has nearly 2 billion users. We...

Lately, I've been thinking about how new features are either launched as stem cells or full blown organs. I'm well aware this is an imperfect analogy, but I'm OK with that. It's close enough to make me think, which is all that matters in my book. A stem cell is essentially an undifferentiated cell that can change — or differentiate — i...

There’s no shortage of lore about the importance of the elevator pitch. There’s the 1850s version, in which inventor Elisha Otis’s dramatic demonstration of his innovation — a safety brake that keeps elevators from falling during a cable failure — set a new bar for colorful, efficient salesmanship. There’s the Hollywood version, in whi...

I'm often asked how I know when an idea might make a good product. First, I never know. It's always a guess, a bet. I'm just trying to do what I can to increase the odds, to beat the house. But more specifically, it's always a feeling. It's never a number. It's never a quantity of yesses. It's never about early feedback. It's never abo...

Back in the mid-90s, just as Netscape Navigator was giving us our first look at what the visual internet could be, web design came in two flavors. There was the ultra basic stuff. Text on a page, maybe a masthead graphic of some sort. Nothing sophisticated. It often looked like traditional letterhead, or a printed newsletter, but now o...

At Basecamp we don't manage our products with numbers. No goals, no KPIs, OKRs, or WHATEVERs. We do keep a close eye on performance and speed numbers as they relate to infrastructure, serving up pages, and rendering screens, but that's the extent of our number gazing. We aren't flying blind — there are reports available. If you want yo...

I'm having a new window system installed at my home office. And I'm finding it a wonderful microcosm of business — and life — itself. Here's what it looks like right now: Foam, tape, shims, and glue — they're holding the whole thing together. It's the guts, the organs, the cartilage, and the bones to keep things lined up, and upright. ...

I've never had a personal blog. It wasn't for lack of things to say, observations to share, or opinions to float. It was primarily because setting up a personal blog was just too much of a hassle. It felt formal, it required yet another tool, yet another place to write, yet another platform to pay for just one feature. I had to pick a ...

I can’t remember having a goal. An actual goal. There are things I’ve wanted to do, but if I didn’t do them I’d be fine with that too. There are targets that would have been nice to hit, but if I didn’t hit them I wouldn’t look back and say I missed them. I don’t aim for things that way. I do things, I try things, I build things, I wan...

Much of the tension in product development and interface design comes from trying to balance the obvious, the easy, and the possible. Figuring out which things go in which bucket is critical to fully understanding how to make something useful. Shouldn’t everything be obvious? Unless you’re making a product that just does one thing – li...

Years ago I used to be a hothead. Whenever anyone said anything, I’d think of a way to disagree. I’d push back hard if something didn’t fit my world-view. It’s like I had to be first with an opinion – as if being first meant something. But what it really meant was that I wasn’t thinking hard enough about the problem. The faster you rea...