Ep.9 From Insurance to Investing: Ricky Bouchard on Lower Middle Market Discipline
In this episode of The SMB Investor Podcast, Sean Smith talks with Ricky Bouchard — a former insurance professional turned disciplined SMB investor. Ricky walks through his transition from backing friends to building a strategic investment approach grounded in familiar industries, strong operator communication, and resilient capital structures.He also exposes hidden risks in insurance coverage, shares real-life diligence lessons, and explains how to recognize deals where he can truly add value as an investor.A candid and tactical conversation filled with insights for operators, LPs, and anyone navigating the world of small business acquisitions.
--------
35:05
Ep. 8 More Than Capital: Jeff Driskel’s Playbook for Operator-Led Acquisitions
In this episode of The SMB Investor Podcast, Sean Smith sits down with Jeff Driskel — NFL quarterback and founder of The Four Pillars Group — to discuss his transition from professional sports to private equity, and his innovative, operator-led approach to acquisitions.Jeff explains how Four Pillars focuses on finding exceptional leaders first and shaping investment theses around them. Together, they explore what makes a great operator, why traditional search fund models aren't for everyone, and how to build companies that endure beyond the transaction.A must-listen for athletes, investors, and aspiring operators looking to master leadership, focus, and long-term value creation in SMB investing.
--------
18:10
Ep. 7 How to Finance SMB Acquisitions: SBA, SBIC & Debt Strategies | Zach Pavlosky & Sean Smith
In this episode, Sean Smith interviews Zach Pavlovsky from Cerebro Capital, who has led over $850M in debt financing for lower middle market acquisitions. They discuss the landscape of SBA, bank, and SBIC financing, and what searchers and sponsors need to consider when negotiating loan terms.A must-listen for anyone navigating SMB acquisitions and looking to understand how lenders assess deals and structure capital.
--------
24:49
Ep. 6 Investing in Hidden Gems: How to Evaluate Trade Businesses
What makes blue-collar businesses some of the most valuable and overlooked opportunities for private investors?In this episode, John Bartlett (Founder of Brentwood Growth) joins Sean Smith to share over three decades of experience in trade services M&A. From roofing and janitorial to fencing and pool service, John breaks down why these sectors are gaining institutional attention—and how operators and investors can unlock their full potential.He also introduces his “Seven Levels of Growth” framework and offers practical guidance for scaling, timing inorganic growth, and evaluating deals beyond the numbers.If you're an investor, entrepreneur, or search fund operator looking to grow in the service trades, this episode is full of actionable insights.
--------
30:26
5. Scaling Through Strategic Acquisitions | Bob Wang & Sean Smith
How can entrepreneurs use acquisitions to unlock growth and scale more effectively?In this episode, Bob Wang (Founder of T-Up Advisors) joins Sean Smith to explore how small business owners can leverage inorganic growth to overcome operational challenges, reduce customer concentration, and boost enterprise value ahead of a successful exit to private equity.From common pitfalls like overleveraging and "deal fever" to frameworks for building a scalable platform, Bob shares real-world strategies for making M&A work in the SMB space.If you're a search fund operator, investor, or entrepreneur looking to grow smarter and avoid costly mistakes, this episode is packed with insights you won’t want to miss.
Forget startups. Forget climbing the corporate ladder.
The real path to wealth? Owning profitable small businesses.
Hosted by Sean Smith and Nick Bryant, The SMB Investor dives into how investors, operators, and dealmakers are building wealth through small business acquisitions, syndicates, and holding companies.
We talk to the pros—fund managers, investors, searchers, and service providers—who are making SMB investing the next big asset class.
Whether you want to invest, operate, or build your own holding company, this podcast is your playbook.
Ireland