Jeff Epstein paid off his law school student loans in an unconventional way. When he and a couple of friends noticed the booming online poker sites in the mid 2000s, they created an affiliate company to refer traffic to them and get paid in return. The business did well enough that Epstein was able to sell his stake to his partners for a nice profit that helped him pay off his debt. Epstein ultimately decided not to pursue law, but his entrepreneurial experience stuck with him. In particular, he recognized the power of referrals to help businesses gain more customers. As a result, Epstein eventually founded Ambassador, a referral marketing software that enables brands to build and scale referral, affiliate, partner, and influencer programs. While the journey to growing Ambassador was far from a smooth ride, Epstein picked up many valuable lessons along the way that helped him grow as both a person and an entrepreneur. Eventually, Ambassador became successful enough that it was acquired by a large corporation. Check out this interview to learn more about Epstein’s journey and hear him open up about his biggest mistakes, regrets, and lessons learned. Key Takeaways How Epstein used his poker affiliate business to pay off law school debt What he learned about the power of referrals in the process Why Epstein regrets acquiring his first SEO company, and what ultimately led to its demise How this failure informed the idea for referral marketing software, Ambassador Why it took six months for Ambassador to get a repeat paying customer What it was like to run a “fat” startup How Ambassador’s acceptance into Techstars helped the company take off The growth of Ambassador and its stressful acquisition by West Corporation