Twins Matthew and Michael Vega-Sanz dropped out of Babson College in 2018 to build a car-sharing app—then Covid-19 totaled it. “We had negative $2,800 in the bank and a dead startup. We felt like absolute failures,” says Matthew, the startup’s CEO. But the setback was just a detour to a bigger business. Their new startup, Lula, helps almost 5,000 logistics and car rental companies build flexible insurance packages to reduce premiums, such as offering pay-per-day insurance for trucking fleets, car sharing and daily rentals. Coming soon: AI to sell the insurance. They count Flexport, the unicorn shipping company, among their customers and have $45 million in funding from folks like Founders Fund and Khosla Ventures. The first generation Americans see it as their duty to take big risks. “Founders, especially here in the United States, have the privilege to be crazy,” Matthew says. “I think about our family in Cuba, where being crazy gets you locked up as a political prisoner.”