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What's Your Deal? | Business Buying, Business Acquisitions, Investing & Exit Strategies

What's Your Deal? | Business Buying, Business Acquisitions, Investing & Exit Strategies

Failure Is an Option: Lessons from 6 Venture-Funded CEO Roles - Mike Grossman

Oct 21, 2026 · 46m

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On this episode

About this episode

Matt Uhler sits down with Mike Grossman, author of Failure Is an Option and a veteran CEO of six venture-funded companies. Mike explains how two failed attempts to take a company public led to an acquisition worth meaningfully more than the IPO. He covers why you should focus on inputs instead of outcomes and the danger of chasing adjacent opportunities. He also explains when it's worth defying your board, why spending discipline matters, and how a fully remote team of 300+ changed his view on recruiting. Connect with Mike Grossman: Book: Failure Is an Option, available on Amazon, Barnes & Noble. Website: failureisanoption.com https://www.instagram.com/failureisanoptionbook Connect with…