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.
