CD Baby founder Derek Sivers made two appearances on Venture Voice in the early days of this podcast. In our first conversation, he described the process of growing the company into one of the largest sellers and distributors of independent music online, with $25 million in revenue and 50 employees at the time. This week we’re revisiting our second conversation, which happened three years later. What a difference three years makes.

In August 2008, Derek, who owned 100% of the equity, sold the company for $22 million. When we spoke in October of that year, Derek described what drove his decision to sell the company, how he sold it (including a Willy Wonka style plan that never came to fruition) and what he learned along the way. As you’ll hear, Derek wasn’t driven by the money. If anything, it was a deterrent to selling. So his lifestyle didn’t change when he sold CD Baby — and he made sure of that by putting all of the money into a charitable trust that will go toward music education when he dies. If you’ve ever felt disconnected from your own venture or wrestled with the idea of whether you should sell your “baby,” this episode offers some good insight and excellent advice.

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