Shopify: Tobias Lütke. How a snowboarder built a $150 billion business (2019)

Loren Castle started baking cookies after surviving cancer in her early twenties. Five years later, Sweet Loren’s refrigerated cookie dough was generating just $350,000 a year. But instead of giving up, she listened to customers, and reinvented the dough without gluten, dairy, eggs or nuts. That transformation turned a small regional business into a national brand sold in more than 30,000 stores. WHAT YOU'LL LEARN

Today’s callers: Lindzi from Chicago wants to expand her gourmet marshmallow brand into retail without cannibalizing her high-margin DTC sales. Then, Vivi from Hawaii considers how to best tell her sustainable swimwear brand’s story to a digital audience. And Aly from Los Angeles wonders whether a subscription model is best for her whimsical curated experiences.

In the early 1990’s, Tim League spent $50,000 in savings to lease an abandoned movie theater on the wrong side of the tracks—a shaky experiment that eventually grew into a thriving national chain. As Tim and his wife Karrie built theaters in Austin and beyond, they made a name for themselves by offering dinner with the movie, creative pairings (like sake with Godzilla), and roadshows where movie-goers could watch Deliverance in canoes, or Rocky on the famous steps in Philly. Alamo Drafthouse Cinema now has dozens of locations across the country, but there have been plenty of bruises along the way: a failed first theater, a fractious lawsuit with business partners, and a swan dive into the red during the pandemic. This episode was produced by Carla Esteves, with music by Ramtin Arablouei. Edited by Neva Grant, with research help from Carla Esteves.

Today’s callers: Mercedes in Utah tries to find harmony between quality and speed as she scales her concert attire brand for musicians. Then Danny in Colorado grapples with the tradeoffs of growing his sustainable and functional coffee brand. And Riya in Illinois wonders how to build awareness for her app that aids people affected by speech loss. Plus, Nick’s insights on how AI is changing the way we fill our grocery carts — and how grocers respond to food and nutrition trends.

Stories about starting a business are almost always full of drama. They’re about ambition, loss, triumph, catastrophe, resilience. And they’re also full of life lessons – which is why Guy Raz launched How I Built This 10 years ago: He wanted to host a free master class in entrepreneurship, one conversation at a time. Ten years on, he’s conducted over 600 interviews with some of the world’s most successful founders, and on today’s show, he replays some of the most memorable moments and lessons. Joining him is Jamie Siminoff, the founder of RING and a former guest on the show. Why Jamie? He’s a friend, a fan, and – as you may remember from his first interview - he doesn’t hide his emotions.