Jeff Lawson’s Great Leap: Can the Twilio CEO Fix His Company and His Country at the Same Time?

One afternoon toward the end of September, Jeff Lawson’s household was turned upside down: Barack Obama was coming to visit.

At their glassy, modernist home high above San Francisco’s Dolores Park, Lawson and his wife Erica shuffled around the furniture to make room for the former president and their three dozen other guests. Venture capitalist Ron Conway and LinkedIn co-founder Reid Hoffman were billed as co-hosts for the evening fundraiser, which benefited the Democratic Grassroots Victory Fund. Tickets cost $250,000 a seat.

“There’s a large percentage of people who no longer believe in elections—whether that’s through the Big Lie or January 6 or gerrymandering,” Lawson told me a week after hosting Obama. “I think it’s really interesting that a lot of business leaders say, ‘I’m staying out of politics.’ Or, ‘I can operate my company with any [party] in charge.’ Well, I don’t think they really know what it’s like to try to run a successful business in a country that’s not a democracy.”