Episode (200)
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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...
Advice Line with Jon Stein of Betterment
Feb 05, 2026Plus, Jon’s take on why now is a good time to start a business — in spite of market uncertainty. Today’s callers: Dan from Washington considers new offerings beyond his core loose leaf yerba mate p...
HOKA: Jean-Luc Diard and Nicolas Mermoud. The “Clown Shoe” That Became a $2B Bonanza
Feb 02, 2026In the late 2000s, two French mountain athletes set out to build a running shoe that captured the feeling of flying. Jean-Luc Diard and Nicolas “Nico” Mermoud had spent decades inside the innovation ...
Advice Line with Serial Entrepreneur Mark Cuban
Jan 29, 2026Plus, Mark on his most challenging venture yet: revolutionizing the prescription drug market in America. First we meet Lucy from Washington DC, considering an opportunity to bring her upside-down ...
Taylor Guitars: Kurt Listug and Bob Taylor. From $3,700 Shop to Global Icon
Jan 26, 2026A bright blue guitar covered in orange koi fish vanished from a museum display … and Swifties immediately knew what it meant. That distinctive guitar—the one Taylor Swift used to record Speak Now—had ...