Practical Founders Podcast

#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, Gregory shares his difficult personal challenges and 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.

Best quote from Gregory:

“When I look at the data from the thousands of founders that I’ve seen that have made it or failed, one of the things that I tell founders is you have to start with the end in mind. Meaning if you’re going to sell your business, you have to know who’s going to buy it and plan for that exit. 

“I get into these arguments with investors. They say, ‘Oh, no. That’s later on you can’t do that.’ And I think that’s ridiculous. Because an acquirer is another business with a specific synergy. A synergy, which is the reason why an acquirer would buy you, is either to save or make money. 

If that’s the case, then your whole business is just a product to your acquirer. Not planning your acquirer when you build your business is like building a business without having a customer.

In this episode, Gregory explains:

  • How he faced serious challenges as a child and adult with autism, dyslexia, savant syndrome, and neuro-divergent disorders
  • His early startup adventures in the early days of the internet and websites 
  • How he helped create performance marketing technologies with referral tracking to help companies pay for just the traffic the brings verified sales
  • How he grow two companies and sold them to eBay, one with over 300 employees, and then spun them out a few years later
  • The thinking and approach he used to create and sell 12 technology companies
  • What he is working on now to help more startups succeed in the early stages



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Greg Head recorded this on episode on June 16, 2023 for the Practical Founders Podcast see all of the episodes.

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