Tags: AI, Entrepreneurship
2025

fear of failure

There is plenty of justifiable criticism of Facebook’s most famous value — Move Fast and Break Things — because plenty of important things really have been broken, but it’s easy to forget how powerful a gravity well mistake avoidance is. High performance people hate failure and will do almost anything to avoid it. Senior managers doubly so.

There was a brief moment when it looked like eBay was going to buy Linden Lab. Philip and I had meetings with Meg and her tech consigliere Maynard. Unlike similar meetings with other leading tech companies, most of the time was both of them explaining to us repeatedly how amazing eBay’s release system of trains, seats, and how engineers who broke user-facing features “lost their bonuses.”

What the shit?

Philip and I were gobsmacked. We adored eBay — Pierre was one of our first investors — but it was clear the product had been stagnating. Now we knew why. Despite that, in the mid-oughts, eBay’s approach was viewed as the Right Way(tm) and plenty of other companies were copying it.

(Date-driven with proper incentives works spectacularly, as we proved during the mobile transition)

Mark understood this and did everything possible to make Facebook willing to take risks.

Something he said has stuck with me: “All organizations have strengths and weaknesses. If you are really lucky, you can choose them.”

Outcomes and values

The last decade has had a lot of failure and discovery — the personal version of strengths and weaknesses and trying to choose some of them. It’s also reminded me how easy it is to confuse effective tactics — getting a company to overcome fear of failure — with the broader questions of whether you support or oppose a particular company or leader.

Especially as AI enables more and more ways to move fast, to take risks, and to fail in spectacular ways, many of us will have to ponder these questions. On the one hand, the speed and amplification of AI will create greater, different, and novel risks from those we are used to considering. That’s real. But many employees and leaders will let those potential failures magnify in their imaginations, creating implicit and explicit barriers for their organizations.

For me, it’s about finding a path through this focused on outcomes that align with my values. Because safe but losing is not a viable strategy.