10 Years of How I Built This: A Decade of Innovation, Risk and Reinvention
How I Built This with Guy Raz
October 5, 2026
Stories about starting a business are almost always full of drama. They’re about ambition, loss, triumph, catastrophe, resilience.
Speakers Guy Raz, Jamie Siminoff, Sam Calagione, Paul Orfala, Katrina Lake, Jim Koch, Sal Khan, Justin Gold, Eileen Fisher, Gary Hirshberg, Mike Krieger, Kevin Systrom, Sara Blakely, Hamdi Ulukaya, Tom Rinks, Mike Cesario, John Mackey, Kathy Hughes, Mel Ziegler, Serena Dugan, Missy Park, Bobbi Brown, Jensen Huang, Toby Lütke, Drew Houston
TopicsBusiness
Guy Raz (0:00)
Our presenting sponsor today is Anthropic, the team behind Claude. Every founder on this show started with a hard question. Not the marketing plan, the 2 AM kind. Is this idea any good? Am I the one to build it? Should I quit my job? Anthropic got built the same way. A public benefit corporation founded on one hard question. How do we make sure AI goes well for people?
So, they asked over 100,000 people their hopes and their fears, and are publishing what they find, even the uncomfortable parts. Me?
I've got my own hard question about AI. Here it is. If everyone has access to something that can help them write the business plan, build the prototype, analyze the market, maybe even come up with the idea, what separates the people who actually build something from everyone else?
I don't have a clean answer yet, so I've been sitting with it, with Claude. There's hope in hard questions. Ask yours at claude.ai/h i b t.
We get support from US Bank. A question I love asking founders. What's the one decision you almost didn't make? The one that changed everything? Because it's never the obvious stuff. It's never I decided to start a company. It's the small, boring, Tuesday afternoon decision you barely remember making until you realize it's the reason everything after it either worked or didn't. Say you're 18 months in. Business is growing. You've got expenses coming from six directions, gas for the van, office supplies, your phone bill, team lunches that are actually client meetings. And you're putting it all on whatever card you grabbed in year one. You're not thinking about it. Why would you? You've got bigger problems. But here's the thing. Path A, you keep going like that. End of the year, you're sorting through statements, trying to figure out what went where. You've left hundreds, maybe thousands on the table and rewards you never earned. Money that could have gone back into the business. Path B, you pause and get the US Bank Triple Cash Rewards Visa Business Card. Now you're earning 3% cash back on gas and EV charging, office supply stores, cell phone service and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR in purchases and balance transfers for 12 months while you're scaling.
Same business, same expenses, two completely different outcomes based on one small decision.
Visit usbank.com/business to learn more. The creditor and issuer of this card is US. Bank National Association, pursuant to a license from Visa USA Inc. Some restrictions apply.
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When I pull up to a gas pump to fill my car, I'm not thinking about chemistry or engineering. I'm thinking about getting in, filling up, and getting on with my day.
It reminds me a little bit of the founders I talked to on this show, because the best ones obsess over things their customers will never see.
Tiny details, invisible improvements, relentless iteration, and not because anyone's watching, but because it makes the product better. That's what the mobile brand does. It engineers fuel the same way great founders engineer their products. Mobile Supreme Plus Premium Gas helps keep engines three times cleaner, which can mean better performance and improved gas mileage. It's for people who care about what's under the hood, even if they never see it. Three times cleaner compared to mobile regular gas in port fuel injected engines. Actual results may vary. Visit mobilefuels.com for details.
Jamie Siminoff (5:19)
There's so many things to worry about in business, including what you don't know. Fear drives me.
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