280: From Online Poker Affiliate to Referral Marketing Mogul: Ambassador’s Jeff Epstein Shares His Journey

280: From Online Poker Affiliate to Referral Marketing Mogul: Ambassador’s Jeff Epstein Shares His Journey

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

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627: How Lia Georgantis Built an Iconic Aussie Fashion Brand in Just 5 Years

627: How Lia Georgantis Built an Iconic Aussie Fashion Brand in Just 5 Years

Lia Georgantis took over a multi-brand fashion boutique with no business experience, lost most of her suppliers overnight, then rebuilt it into one of Australia’s most recognisable fashion brands by...

29 Jan 58min

626: (Solo) Work Life Balance Is an Illusion. Here’s What Works Instead

626: (Solo) Work Life Balance Is an Illusion. Here’s What Works Instead

Most founders won’t say this out loud… work-life balance doesn’t really exist. At least not in the early years. I didn’t want balance — I was obsessed. I worked until 5 a.m., skipped sleep, skipped ho...

27 Jan 10min

625: From $70M in Debt to $1B Amazon Deal in 45 Days | Jamie Siminoff

625: From $70M in Debt to $1B Amazon Deal in 45 Days | Jamie Siminoff

One billion dollars. That’s what today’s guest built — after being rejected on Shark Tank, nearly going bankrupt multiple times, and spending millions before making a single sale. In this video, Jam...

22 Jan 55min

624: (Solo) How to Create More Than You Consume (Without Burning Out)

624: (Solo) How to Create More Than You Consume (Without Burning Out)

Most founders drown in content — YouTube, TikTok, newsletters, podcasts — but they rarely create anything themselves. And here’s the problem: consumption doesn’t build businesses; creation does. In...

20 Jan 9min

623: $500K in Debt, 5 Maxed Credit Cards — How Jordan Harper Built an 8-Figure Brand in Year One

623: $500K in Debt, 5 Maxed Credit Cards — How Jordan Harper Built an 8-Figure Brand in Year One

Jordan Harper built an eight-figure skincare brand in its first year by maxing out five credit cards while already $500,000 in debt — and never raised a single dollar from investors. In this inter...

15 Jan 55min

622: (Solo) The Truth About Founder-Led Content in 2026

622: (Solo) The Truth About Founder-Led Content in 2026

Founder-led branding isn’t dead — but it is evolving fast. Showing your face and posting “day in the life” content is no longer enough to stand out. The bar has risen, audiences have matured, and what...

13 Jan 8min

621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

Nala was built by two founders with no fashion background who invested $200,000 before making a single sale and went on to sell over 400,000 pieces in just two years. In this interview, Chloe and ...

8 Jan 51min

620: (Solo) The Secret to Making Bold Business Moves With Confidence

620: (Solo) The Secret to Making Bold Business Moves With Confidence

One of the biggest challenges founders face — especially at the end of the year — is knowing what to do next and feeling confident that the move you're about to make is the right one. Certainty feels ...

6 Jan 11min

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