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.

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.