This Week in Startups · Monday, June 29, 2026
Chamath Palihapitiya discussed his philosophy of applying a 'Tom Sawyer' approach to business, where a perceived chore or cost center is turned into an engaging community activity. He cited his podcasting ventures as an example, turning conversations into profitable content by inviting others to participate. Similarly, 'Learn with Me' leverages community to validate content and create a subscription service, while 'Drink with Me' aims to build relationships with winemakers and consumers.
“You took something that was a cost center. You then brought a community into it. So they act in two ways. They validated it. They make sure the information is correct, but you took something that's a $4 million, you know, money pit. And now you own this. You get to direct it.”
“And if you can take something you're doing anyway, and Tom Sawyer it, I did that with podcasting. I was going and having lunch with you and having a great conversation for two or three hours and it was like, hey, turn the cameras on. Why don't we share this with people?”
“And then all of a sudden, it was profitable. Oh my God, this opens up so many doors. And you get that correcting mechanism. You're bringing a bunch of folks.”