Dear Jeff

You could blow up the extractive motive if you wanted to

I‘ve been thinking about your regret minimization framework for making decisions lately. I don’t recall whether I read about it in an interview, or if you shared it with Jason and me in person in those early days after your involvement in Basecamp. But regardless, I think you’re currently making bad decisions that you’re going to regret. Maybe even decisions that we as a whole society will come to regret.

It doesn’t have to be like this. You’re literally the richest man in the world. Markets have suspended disbelief for decades, and let you rule as you see fit. It’s well within your power and purvey to change course.

The HQ2 process has been demeaning if not outright cruel. At a time when politicians are viewed as more inept, more suspicious, and more corrupt than ever, you made city after city grovel in front of your selection committee. They debased themselves in a futile attempt to appeal to your grace and mercy, and you showed them little. The losers ended up worse than where they started, and even the winners may well too.

For what? Extracting a few more billions that Amazon does not need in subsidies? If you tilt your perspective a little, I think you’ll be able to catch the optics that the richest man in the world asking for tribute like this is an ugly one.

Amazon is Jeff Bezos. You can’t cover decisions behind committees or other shareholders. You hold the reins, you reap the lion’s share of the rewards, and thus you’re accountable for its actions.

As many great conquerors in history, I’d be surprised if you didn’t care about establishing a legacy. I mean, you clearly already have. But there’s still time to shape that legacy into something more than the man who killed retail, extracted the greatest loot from its HQ cities, and who expanded the most monopoly holdings the fastest.

Rather than keep asking what cities and countries can do for Amazon, maybe start asking what Amazon can do for them. Be magnanimous. Be responsible.

Not just because it’s the right thing to do, but because it’s the smart thing to do. The better business move. At some point people are going to have had enough, and when they figure out a way to channel that discontent into political action, they’re going to come looking for the heads of those that did them the most egregious wrongs.

I know it doesn’t look like that big of a risk right now. People still seem to trust Amazon more than most of the big tech companies, but that’s a lagging indicator. The clouds are gathering in the distance. It starts with a few pioneers calling for antitrust action, and then one day you wake up, and that’s what the whole world wants.

It’s hard to be proud of having you as a minority owner in Basecamp right now. Maybe there’s even a tinge of regret. I’d very much like to minimize that.


Jeff owns a minority, no-control stake in Basecamp (the company that Jason and I co-own). For the first few years after purchasing that, Jason and I would meet or talk to him about once a year. It’s probably been 7–8 years since we spoke with Jeff directly last. If we get another chance, this would be the most pressing topic.

The Bezos way: sleep, puttering, and three high-quality decisions a day

One of the most successful business people in the world…putters?

Jeff Bezos has always been one of those people whose ideas and thinking make a lot of sense to me. When he talks, I listen.

So when I recently came across a fantastic interview with Jeff Bezos, I jumped right in. The entire interview is great and I really think watching the whole thing is worth your time. But there was one section that really stuck out to me: his prioritization of sleep, calm, and quality.

https://www.youtube.com/watch?v=kfY3uRCvEMo

It’s 2 minutes and 29 seconds of your day well spent, but here’s the basic gist:

  1. 8 hours of sleep a night. He goes to bed early and wakes up early. He thinks better, has more energy, and his mood is better when he gets the right amount of sleep, all of which contribute to making him an effective decision maker. The opposite can hold true too — being tired or grouchy can lead to bad decisions.
  2. Puttering (yes, this is an official Bezos term). Bezos’ morning routine isn’t manic or hectic, it’s quite the opposite — he putters around, taking his time and slowly ramping up. This is his time to read the paper, have coffee, and eat breakfast with his kids. It’s really important to him that he have a slow, calm start to the day, which is also why he insists on no meetings before 10 a.m.
  3. High quality decision making. He likes to do his “high IQ” meetings before lunch because that’s when he’s sharpest, and he knows by 5pm he’ll be wiped. Anything that’s important that pushes late into the day gets rescheduled for 10 a.m. the next day. He recognizes that he “only” needs to make a few key decisions a day, not thousands of small ones. If he can make three high quality decisions a day, that’s plenty good.

This is astonishing and inspirational for all the right reasons. For all we hear about how awesome it is that people are constantly “hustling”, working 20 hour days, sending 50 emails from bed, and squeezing every minute of the day for max productivity, we have in front of us Jeff Bezos — one of the most successful business people in the world— puttering.

Sleep. Calm. Prioritizing. Quality over quantity. Recognizing limits. These are the kinds of principles that have made him a wild success in the long run. I think we’d all do well to mimic these practices.

Excuse me while I go putter around for a while. 🚶


We agree with Jeff’s ideas on sleep and calm — so much so that Jason and David wrote a book about it! Check out “It Doesn’t Have to Be Crazy at Work”.

Some advice from Jeff Bezos

A number of years ago, Jeff Bezos stopped by our office and spent about 90 minutes with us talking product strategy. Before he left, he spent about 45 minutes taking general Q&A from everyone at the office.

During one of his answers, he shared an enlightened observation about people who are “right a lot”.


He said people who were right a lot of the time were people who often changed their minds. He doesn’t think consistency of thought is a particularly positive trait. It’s perfectly healthy — encouraged, even — to have an idea tomorrow that contradicted your idea today.

He’s observed that the smartest people are constantly revising their understanding, reconsidering a problem they thought they’d already solved. They’re open to new points of view, new information, new ideas, contradictions, and challenges to their own way of thinking.

This doesn’t mean you shouldn’t have a well formed point of view, but it means you should consider your point of view as temporary.

What trait signified someone who was wrong a lot of the time? Someone obsessed with details that only support one point of view. If someone can’t climb out of the details, and see the bigger picture from multiple angles, they’re often wrong most of the time.

Great advice.

The deal Jeff Bezos got on Basecamp


In 2006, Jeff Bezos bought a minority, no-control stake of Basecamp from Jason and me. We didn’t need any money to run the company, as we’d been profitable from the get-go, so none of it went to fund “our incredible journey”. As the Valley players say, we took money off the table.

It was an unusual deal for a number of reasons. First, Basecamp remained an LLC, which it still is. Not a corporation. Bezos’ personal investment shop simply took the role of a member in the LLC. This means that even to this day our paperwork and administrative overhead is laughably simple (Basecamp has no CFO, not even a full-time accountant!).

Second, there was no exit lined up! Jeff did have a one-time provision to sell his stake back to us after, I believe, seven years, but we didn’t trigger it, so now we’re in this together with no end in sight.

What Jeff got was the same deal that Jason and I had: His share of the yearly profits. What a quaint concept! But also a profitable one. Over the more than a decade that Jeff has been onboard, we’ve paid him back his initial investment five times over through profit distributions! And he still owns the stake.

What Jason and I got from the deal was the total confidence to go the distance. In 2006, we’d only been running Basecamp for a few years. We’d been besieged by venture capitalists and acquisition sniffers. But Basecamp wasn’t actually making that much money yet. Profitable, yes, but modestly so.

It’s only human to be tempted in such a situation. Only a year earlier, Yahoo had bought Flickr for some twenty million dollars. Jason and I had both been through the dot-com bust of the early 2000s. Now all of the sudden money was flowing again. So your mind wanders.

But thankfully it didn’t wander all that far. We had a good thing going, and we had no interest in giving it up. But at the same time, it seemed prudent to hedge the bet at least somewhat. It was entirely possible that Basecamp could have petered out, and we’d been back to doing consulting with no residual to show for it. That wouldn’t exactly had been the end of the world, but surely it would have engendered some regret.

Speaking of which. When we first started talking to Jeff, he spoke of his regret-minimization framework. It applied very well here. If we sold part of the company to VCs or all of it to some big company, there was a very good chance we’d end up regretting it. We’d be working for someone else, be on their timeline. All the ills we’ve been talking about for a long time.

But selling a small, no-control stake to Jeff? If Basecamp was going to fail, clearly we wouldn’t regret that. And if Basecamp was going to succeed, we’d not regret it either, since Jeff’s involvement would only mean giving up a small slice of the upside, without any of the normal investment-induced drawbacks.

The hardest part was actually talking Jeff down on the size of the purchase. Originally he wanted a bigger slice, which would have meant more money for Jason and I, but it would also have meant giving up more of the company. We decided that all we needed were a few million each to protect the downside of a bust, so that’s what we sold him.

I think it’s a shame that arrangements like this aren’t more common. I think many companies would be better off if the founders got to hedge their bet just enough to dare go the distance without the anchor of traditional venture capital.

The big financial cliff for most entrepreneurs is the difference between no net worth and a few million. The difference between having a few million and a lot of millions is vanishingly small in comparison.

Well, I suppose that even a lot of millions is now a vanishingly small difference to Jeff. He just got crowned the richest man in the world. But you get the point 😂