The Evolution of Entrepreneurship: Ryan Deiss on Growing and Scaling Businesses Part 1

19 Nov 2025 · 33 min
Episode

19 Nov 2025 · 33 min

0:00

Ryan Deiss built his first business as a college side-hustler in 1999, earning $150k+ a year by graduation. He talks about near-bankruptcy, the personal toll of growth, and why founders fail at scaling: they hire too fast, push harder instead of changing systems, and expect one person to fix everything.

Questions this episode answers

July 1, 2024

1999 (high-speed internet newly installed in his dorm)

Around $150,000 per year (he said 'well in excess of $100,000... around $150,000 a year')

About $200 million in revenue collectively

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