Carson Poppenger, CEO of Squeeze: Doubling Sales for 5 Years after Flat Growth for 11 Years cover art

Carson Poppenger, CEO of Squeeze: Doubling Sales for 5 Years after Flat Growth for 11 Years

Carson Poppenger, CEO of Squeeze: Doubling Sales for 5 Years after Flat Growth for 11 Years

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How do you go from being "stuck" at $2M in revenue for years to crossing the $100M threshold?

In this episode of the Fearless Founders Club, we sit down with Carson Popinjay, CEO of Squeeze Media. Carson shares the raw, unfiltered journey of his 17-year entrepreneurial career—specifically the 11-year "grind" where growth remained flat, and the pivotal changes in 2019 that led to doubling the business year-over-year.

In this episode, we discuss:

  • The "Found Revenue" Strategy: How marketing automation and mining old data can create instant growth.

  • The Scaling Pivot: Why Carson moved from working in the business to working on the business.

  • The Capital Dilemma: When to take on a partner and why having enough funding is the fuel for product-market fit.

  • Leadership & Integrity: Managing over 6,000 employees without a single legal subpoena.

  • Direct Feedback: Why "niceness" can be a silent killer for small businesses and how to implement radical transparency.

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