Episode (200)
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Advice Line with Hernan Lopez of Wondery
Mar 12, 2026Today’s callers: Heather from Ontario talks through a DTC strategy for her retail pain relief tape and patches. Then Nawal in Michigan considers a rebrand for her uniforms designed for Muslim students...
Bobo’s: Beryl Stafford. A Single Mom Turns a Baking Project into a $100M Business
Mar 09, 2026Bobo’s: Beryl Stafford. A Single Mom Turns a Baking Project into a $100M Business At 40, Beryl Stafford’s life cracked open. Her marriage ended, she hadn’t worked in years, and she had two daughters ...
Advice Line with Miguel McKelvey of WeWork
Mar 05, 2026Today’s callers: Jane in Minnesota wants to scale her artful pants brand while staying true to her locally-made mission. Then Melissa in New Mexico wonders how to respond to diminishing returns on dig...
Kettle Chips: Cameron Healy. The Wild Bet That Made a Brand
Mar 02, 2026Kettle Chips: Cameron Healy. The Wild Bet That Made a Brand Most founders expand the “right” way: local → regional → national → international. Cameron Healy totally skipped the “national” part. When ...
Advice Line with Alexa Hirschfeld of Paperless Post
Feb 26, 2026Today’s callers: Jess from Washington seeks counsel on structuring a collaboration between her sympathy cards company and a pet products brand. Then, Caroline from Colorado wonders if she should build...
Square: Jim McKelvey. He Lost a $2,000 Sale, Then Built a $10 Billion Company
Feb 23, 2026Most entrepreneurs think the hardest part of building a company is the product. For Jim McKelvey — co-founder of Square — the hardest part was the system around the product. Because Square wasn’t just...
Advice Line with Pete Maldonado and Rashid Ali of Chomps
Feb 19, 2026Today’s callers: Yadi from New York thinks through an expansion strategy for her college campus-based empanada business. Then, Zachary from New York looks for ways to break into big retailers with his...
Spinbrush: John Osher. The Electric Toothbrush That Sold for $475M
Feb 16, 2026Before Spinbrush became the top selling toothbrush in the U.S—and before Procter & Gamble paid $475M for it—John Osher was a teenager selling earrings for $4.99. In this episode, John walks through t...
Advice Line with Julia Hartz of Eventbrite
Feb 12, 2026Today’s callers: Mia from Germany wants to know how to balance her pottery business between an online shop and a YouTube channel. Then, Jen from Connecticut is looking for ways to reach more families ...
Netflix: Reed Hastings. “We’re Not a Family.” The Provocative Idea That Helped Build a Streaming Giant
Feb 09, 2026Netflix shouldn’t have survived. In 1997, Blockbuster owned home entertainment—9,000 stores, a business fueled by late fees, and a brand that felt untouchable. Netflix was a scrappy DVD-by-mail experi...