#50: Serial bootstrapper sold two companies to eBay and won very big – Gregory Shepard

Gregory Shepard is a serial entrepreneur who has created and sold 12 companies, including marketing software and ad technology companies. In 2016, he sold two of his bootstrapped software companies, AffiliateTraction and AdAssured to eBay for an undisclosed "f*ck-ton of money," as he describes it. He is now an author, speaker, philanthropist, investor, and the creator of Startup Science and BOSS, an open-source business operating system to help more startups succeed. Gregory faced monumental challenges as a child growing up in poverty with a rare combination of autism, dyslexia, synesthesia, savant syndrome, and other neurodivergent conditions. He learned to develop himself and overcome big challenges, including creating, growing, and running many software companies over three decades.  In this interview, Greg shares his difficult personal challenges and his successful entrepreneurial journey as an experienced practical founder. He also shares several powerful insights and approaches for bootstrapped software founders that you won't hear from investors or the current startup education. Learn more at practicalfounders.com.