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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Today, Sammi is joined by Ariel Kaye, the founder of Parachute—the cult-favorite home essentials brand that helped define the direct-to-consumer movement. Ariel shares the real story behind Parachute’s early days: from bootstrapping her first launch to navigating funding rounds, managing growing pains, and expanding from digital to retail. She opens up about the emotional toll of solo entrepreneurship, the importance of mentorship, and how she kept her business grounded in customer experience—even during the chaos of COVID.
Plus, Ariel reveals how she thinks about growth today, the pressures of staying independent, and why having options—not obligations—is the real founder flex.
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Here’s what Sammi covers today with Ariel:
00:00 Ariel Kaye’s Social Currency
02:49 Early Customer Research and Product Iterations
07:53 Launch Mode: The First Products, First Wins
11:20 Fundraising Without Losing Focus
15:32 What Early Growth Looked Like
17:39 Why Parachute Went IRL With Brick-and-Mortar
21:44 COVID Curveballs
24:19 Building a Full Lifestyle Brand
27:35 Making Marketing Personal
31:32 How Ariel Earns Customer Trust
39:47 The Emotional Side of Building Solo
42:02 How to Show Social Currency Some Love
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