PLAY IN THE RIGHT SANDBOX: IPO Failure, Avoiding the Agency Trap & How to Build Assets Instead with Eric Berman
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Builders, this one goes deep. 🎧
In this episode, I sit down with Eric Berman - Founder/CEO of Speakeasy Mastermind- for a wide-ranging conversation about ownership, follow-through, community, and what it actually means to build success that lasts.
Eric has been building companies since the early days of the internet. He’s helped scale platforms, worked alongside names like Brian Tracy and Jack Canfield, lived through near-IPO highs and market-crash lows, and spent decades inside the agency world.
This conversation isn’t about hype. It’s about what you learn when you’ve been in the arena long enough to see the patterns.
We talk about the invisible cost of agency life, why most entrepreneurs underestimate follow-through, and how community becomes a strategic advantage, not a “nice to have”- as the game gets more complex.
In this episode, we explore:
00:00 – 13:00 | Becoming a Builder & The Crash
Eric’s early path into entrepreneurship, why building from nothing lit him up, and the reality of the "IPO that never happened"- being weeks away from a massive exit and watching it disappear.
13:00 – 24:20 | Resilience & The Pivot
How to navigate the aftermath of a market crash. We unpack resilience, identity, and why skills can’t be taken away, even when money can. Plus, how Eric pivoted to working with legends like Brian Tracy.
24:20 – 36:00 | “I Am Responsible”
The mindset that changed how Eric leads, navigates setbacks, and builds trust with clients and teams. Radical ownership as a leadership unlock.
36:00 – 48:00 | The Agency Trap
The realities of service businesses, capped upside, and the moment Eric realized he’d been climbing the “wrong ladder”. Why the agency model often traps founders in a cycle of revenue without asset value.
48:00 – 52:30 | Follow-Through as a Superpower
Why high follow-through is rarer than vision - and why it quietly separates builders who scale from those who stall.
52:30 – 59:30 | Asset Equity & Redefining Success
Why Eric is shifting from clients to partners, plus a candid look at fatherhood, presence, and how his definition of success has evolved.
59:30 – End | Speakeasy & The Power of Community
How Speakeasy Mastermind was born, why entrepreneurship is lonelier than we admit, and why in-person community matters more than ever in an AI world.
This episode is for Builders who:
• Are successful - but questioning the game they’re playing
• Feel the tension between growth and alignment
• Want leverage, ownership, and freedom- not just revenue
• Know community matters, but haven’t found the right room yet
This is a grounded, honest conversation between two operators who’ve seen enough cycles to know what actually matters.
🔗 Connect with Eric Berman:
https://www.linkedin.com/in/ericberman/, https://www.instagram.com/ericbberman
