EXITS

We sold our last company to Microsoft for $320 million. This time we said let's aim higher. Thirty-two billion higher, as it turned out.

We turned down $23 billion from Google. Then we accepted $32 billion. The $9 billion difference was basically a really expensive negotiation tactic.

We sold Alando to eBay for $43 million, 100 days after we launched it. One hundred days. That taught us everything about speed. If you can build and sell a company in 100 days, you can do anything.

I sold a company to Twitch in my twenties and thought I'd figured it out. Then I realized selling a company and knowing how to invest are completely different skills. Humility is expensive but worth it.

Flickr sold for $25 million to Yahoo. Slack sold for $27.7 billion to Salesforce. Same formula, better timing.

We sold a majority stake for $75 million. The newsletter cost us essentially nothing to start. That's the best ROI I'll ever see.

The best time to sell is when everyone wants to buy from you. That's a lesson most founders learn too late.

Selling a business you built is harder than building it. But knowing when to sell is the most important skill a founder can have.

The hardest decision in this business isn't when to invest. It's when to stop.

The most important lesson my father passed on is that the exit is as important as the entry. Knowing when to sell is at least half the skill.