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Index/Startups & Founders/Up Arrow Podcast
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The Underwear Expert: 25 Years of DTC Lessons Most Founders Learn Too Late

Up Arrow Podcast · 2026-06-23 · 1h 12m

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Episode notes

Michael Kleinmann is the Founder and CEO of Michael Kleinmann Consulting, a bespoke consultancy helping DTC e-commerce and subscription brands grow. He is also the Founder and CEO of Underwear Expert, a men's underwear platform that evolved from a digital media brand into a leading curated subscription service. As a seasoned e-commerce entrepreneur, Michael spent a decade as the President of Freshpair, where he helped build one of the largest online retailers in the underwear category. With over two decades of experience scaling e-commerce and subscription brands, he focuses on brand building, subscriptions, operations, marketing, technology, and customer experience. In this episode… When growth stalls, most brands immediately reach for a new agency, a better campaign, or a larger ad budget. Before pouring more money into an acquisition, leaders have to ask themselves, is the business actually built to scale? The answer is to diagnose the foundation before trying to scale what sits on top of it.

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