The Hardest Thing
Episode Archive
Episode Archive
6 episodes of The Hardest Thing since the first episode, which aired on June 29th, 2026.
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Episode 6: One Yes Away: Former Olympian Priscilla Loomis on Grit, Resilience, and Starting Over
July 24th, 2026 | 39 mins
Kris sits down with former Olympian and motivational speaker Priscilla Loomis during IDEA Week for a conversation about grit, resilience, and what it really takes to build something from scratch and why the Olympic mindset and the entrepreneurial mindset are more alike than you'd think.
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Episode 5: Rebecca Rogers: Millions of Followers. No Plan. No Regrets.
July 17th, 2026 | 49 mins 53 secs
Kris sits down with content creator and former teacher Rebecca Rogers during IDEA Week for a wide-ranging conversation about leaving the classroom with no plan, accidentally building a million-person following, using data to drive content strategy, and why she's never been afraid to be an open book, even when it's hard.
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Episode 4: Dabblers Die: How Nate Spangle Built a Media Empire in the Midwest
July 10th, 2026 | 32 mins
Kris sits down with Nate Spangle during IDEA Week to talk about building a modern media company in Indiana, the loneliness of entrepreneurship, staying relevant as a content creator, and why growing where you're planted beats chasing the coasts.
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Episode 3: From Pop-Up to Acquisition: Sarah Larson Levey on Building, Scaling, and Letting Go
June 30th, 2026 | 45 mins 59 secs
Y7 Studio founder Sarah Larson Levey shares the full arc of building a boutique fitness brand from a free Craigslist pop-up to 15 locations: including the COVID shutdown, a private equity deal, and what it felt like to eventually let the company go.
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Episode 2: Celebrate Authentically: The Loneliness and Wins of Building a Business
June 30th, 2026 | 32 mins 38 secs
Kris and guest Matt Metzger pour some champagne and dig into why entrepreneurs are so bad at celebrating their wins, plus the loneliness of building something, finding your people, and knowing where you fit.
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Episode 1: Acid in Your Stomach: What It Really Takes to Be an Entrepreneur
June 29th, 2026 | 23 mins 45 secs
Kris and surprise guest Mike Haarlander get candid about the real side of entrepreneurship: the stress, the ego, the pivots, and why your mindset matters more than your product.