Best of Bootstrapping: Building a Portfolio of Bootstrapped Businesses

Ryan Millman, CEO of Undigital, has built a portfolio of bootstrapped businesses over the last 25 years that adds up to over $50M in revenue. He discusses the strategies and nuances, pivots and positioning, and more. Sramana Mitra: All right, Ryan. Let’s start at the very beginning of your story. Where are you from? Where

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Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 3)

Sramana Mitra: How did you build that relationship? That is a journey story that would be interesting.

Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 2)

Sramana Mitra: Was there a business model? Were you monetizing? Ryan Millman: Yes. Initially, the business model was based on ad revenue – everything in 1999 was ad revenue-based. I figured out how to tie in with some APIs to one of the first digital photograph manufacturers. People could then order the photographs they were

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Building a Portfolio of Bootstrapped Businesses: Ryan Millman, CEO of Undigital (Part 1)

Ryan has built a portfolio of bootstrapped businesses over the last 25 years that adds up to over $50M in revenue. He discusses the strategies and nuances, pivots and positioning, and more.