June 20, 2025

Adam Sher – Why Your Tax Accountant Is Killing Growth

In this week’s episode, host James Kennedy is joined by Adam Sher, a seasoned CFO who has worked with some of the most exciting growth-stage companies in the startup ecosystem. Adam shares what it’s like to parachute into high-growth environments as a fractional CFO, where finance meets chaos, and strategy meets reality. With a background that spans e-commerce, SaaS, and AI, Adam brings a refreshingly honest take on how CFOs can balance operational excellence with founder vision – especially when the numbers tell a different story. From managing investor expectations to rebuilding financial infrastructure after layoffs, Adam’s war stories offer valuable insights for CFOs, founders, and operators alike.
The Gross Profit Podcast
The Gross Profit Podcast
Adam Sher - Why Your Tax Accountant Is Killing Growth
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Show Notes

In this episode James Kennedy sits down with Adam Sher, founding partner at Prosperity Partners, to take a candid walk through the ups, downs, and hard-won lessons of entrepreneurship. From the rise and fall of a founder story that didn’t go as planned to building a successful small business investment firm from the ground up, Adam offers a rare look behind the curtain of what it really takes to build back better.

They discuss the easy-money “ZIRP era” and what’s changed now that capital is no longer cheap, the realities of navigating M&A in the current market, and the surprisingly powerful role that sales persistence (or what Adam calls “nagging sales”) plays in long-term success.

Stick around to the end to hear Adam’s take on startup incubators, spotting undervalued opportunities, and what founders often get wrong when preparing to exit.


About Adam Sher:
Adam Sher is a founding partner at Prosperity Partners, a firm focused on acquiring and operating enduring small businesses. With a background that spans private equity, entrepreneurship, and hands-on company building, Adam combines financial insight with real-world operational know-how. He’s passionate about giving great businesses a second chapter – particularly from founders ready to pass the torch.


What You’ll Learn:

  • From Failure to Foundation: How a founder story that didn’t work out became the launchpad for Prosperity Partners.
  • The Post-ZIRP Landscape: What’s changed now that money isn’t free – and how that impacts dealmaking.
  • The Power of Persistence: Why consistent outreach and follow-up still outperform silver bullets in sales.

Episode Highlights:

“It’s easy to be a founder when everything’s going up. The real work starts when things go sideways.”

“Nagging sales isn’t about being annoying – it’s about staying relevant until the timing’s right.”

“We’re not here to flip businesses. We’re here to steward them for the long haul.”


More About Adam’s Role:
At Prosperity Partners, Adam Sher leads a hands-on team focused on acquiring and growing small businesses with a long-term mindset. Drawing from his diverse background as a founder, operator, and investor, Adam brings both financial acumen and grounded experience to the table. He works closely with partners and operators to build lasting value – often in industries overlooked by traditional venture or private equity – turning quiet companies into remarkable legacies.

The Gross Profit Podcast

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