I backed a 25-year-old first-time founder who wanted to digitize music. This was 1988. I was excited by the prospect. I knew it was possible, but to most, the idea sounded insane. Peter Gotcher and Evan Brooke had started Digidesign, and I introduced them to Paul Lego, a top student from my HBS class. They built the company that would change music forever. ProTools (now Avid) would allow musicians to track and digitize music. We invested and Paul joined them. As chief operating officer, Paul made a starting salary of $60,000 but negotiated stock options for 8% of the company. Best decision he ever made. By 1993, Digidesign went public at a $100 million valuation. By 1994, Avid Technology acquired them for about $200 million. We made roughly 20x on that investment. Digidesign invented ProTools which is the software that became the standard for musicians everywhere. MC Hammer wrote "Hammer Time" on it. Cant touch this.(Tim Draper)