Top M&A Entrepreneurs

This conversation explores the remarkable journey of Mark Leonard and his creation, Constellation Software, which has grown from a modest $25 million investment in 1995 to a $92 billion empire through a unique acquisition strategy focused on vertical market software companies. Leonard's approach emphasizes patience, discipline, and a decentralized management structure that empowers individual...

I wanted to know more about QSBS…  So I found someone who used it —not just read the IRS page. Kevin McGee is an attorney who bought a craft brewing company. He used QSBS to eliminate capital gains tax on the exit. We sat down and talked about: How QSBS works (and what most buyers get wrong) New rule changes in 2025 that make it even more powerful The legal landmines that can kill your QSBS eligib...

What do crawfish, Walmart, and 7-Eleven have in common? Neal Cobb. He started as a chiropractor. Then built a delivery startup that scaled to 35 states, raised $20M, and was acquired by 7-Eleven. In this episode, Neal shares how he turned down $10M, powered through COVID, and now buys legacy businesses with big EBITDA and long-term upside. Chapters: 00:00 From Chiropractor to Startup Founder 05:38...

👉 How Ready Are YOU to Buy a Business?  Take the free 5-minute quiz: https://www.dealflowsystem.net/bbr-score  🎯 Get your score. Spot your blind spots. Fix them before they kill your deal. Jackie Hirsch has sold over 400 businesses since 1998. In this episode, she breaks down the most common mistakes first-time buyers make—and what separates the ones who close from the ones who never will. We ta...

  Take the Business Buyer Readiness Assessment →     Summary  This guy’s bought SIX companies in just THREE years. And he’s not flipping them. He’s holding for 50 YEARS. In this episode, I sit down with Ryan Sullivan from North Park Group—and if you’re in the M&A game (or want to be), you need to hear this. Ryan’s not chasing shiny objects. He’s quietly building a portfolio of small, family-ru...

  Take the Business Buyer Readiness Assessment →   What Happens When a Guy with Grit Takes on M&A Without a Giant PE Firm Behind Him? In this episode, Casey Minshew lays it out—no fluff. He walks us through his real-world journey as an independent sponsor—finding deals, funding them, and figuring it out as he goes. No Wall Street suits. Just persistence, smart due diligence, and a crew he trus...

  Take the Business Buyer Readiness Assessment →   What We Talked About: I sat down with Sean Smith from SMB Investor Network and we broke down exactly how first-time buyers can actually raise equity to buy a small business — without the usual myths, BS, or dead-end advice. We covered: What investors really want to see before they write a check Why having your own skin in the game still matters (s...

  Take the Business Buyer Readiness Assessment →   Summary In this conversation, Jon Stoddard and Stephen Speer discuss the current state of the e-commerce sector amidst rising tariffs on Chinese imports. They explore the implications of these tariffs on pricing, supply chains, and acquisition strategies for e-commerce businesses. Stephen shares insights on how to navigate these challenges, emphas...

  Take the Business Buyer Readiness Assessment →   Summary If you’re buying your first business — you need to hear this. No, you don’t need to become a business broker. But you’d be crazy not to learn from one. Because 90% of first-time business sales go through a broker... So if you want to win the game , you better understand how the game is played. In this episode, Jeffrey Jump (former Navy, no...

  Take the Business Buyer Readiness Assessment →   Lindsay Gremmer didn’t just buy a company—she engineered an ATM. Starting with a finance degree and zero illusions about how tough business can be, she acquired Vail Financial Services, an accounting firm with solid bones but untapped potential. What happened next? She scaled it like a pro.  She optimized operations, built rock-solid client relati...

  Take the Business Buyer Readiness Assessment →   Alright, here’s the deal—Rob Lombardi went from military life to crushing it in business. But it wasn’t all smooth sailing. He took some hits, learned some hard lessons, and figured out what actually works: adding value, knowing when to exit, and making smart moves instead of just chasing money. His secret weapon? Consulting for equity. Instead of...

  Take the Business Buyer Readiness Assessment →   Summary Jon Stoddard sits down with Jed Morris—a veteran who swapped the military for business ownership. He thought buying a business would be his golden ticket. Instead? A crash course in what not to do. Jed dives into his journey through ETA (Entrepreneurship Through Acquisition), finding and acquiring a landscaping business, and the hard truth...

  Take the Business Buyer Readiness Assessment →   Summary In this eye-opening interview, Jon Stoddard talks with Patrick Lange, a top-tier business broker who has mastered the art of selling HVAC companies. Patrick shares his journey from owning an HVAC business to becoming the industry’s go-to expert for buying and selling HVAC companies. This conversation dives deep into: The critical importanc...

  Take the Business Buyer Readiness Assessment →   Summary In this conversation, Jon Stoddard interviews Scott Wiebel from Sierra Pacific Partners, delving into the intricacies of investment banking and the business selling process. They discuss the importance of building relationships for deal flow, the motivations behind selling a business, the due diligence process, and the emotional aspects of...

  Take the Business Buyer Readiness Assessment →   Summary In this conversation, Jon Stoddard interviews Jules Brenner from Metal Solutions Holdings, discussing the company's journey in acquiring multiple welding and metal manufacturing businesses. They explore the importance of partnerships, the challenges of refining a buy box, the self-funding approach, and the unique landscape of Californ...

  Take the Business Buyer Readiness Assessment →   Summary Can Self-Funded Searchers REALLY Raise MILLIONS of CAPITAL to Buy a Business?  Sean Smith of Search Fund Ventures explains how its done.  Takeaways •  Search Fund Ventures focuses on self-funded searchers and independent sponsors. •  They target essential products and services for investment. •  Investment involves filling equity gaps for...

  Take the Business Buyer Readiness Assessment →   Summary In this conversation, Jon Stoddard interviews John Panaccione, an Army veteran and entrepreneur who co-founded LogicBay and later launched Folla Capital. They discuss the intricacies of participating preferred equity, the challenges of raising capital for small to medium-sized business acquisitions, and the evolving landscape of SBA loans....

  Take the Business Buyer Readiness Assessment →   Summary In this conversation, Daniel Gertrudes shares his journey from a corporate background to becoming an entrepreneur in the accounting industry. He discusses the challenges and insights gained from acquiring accounting firms, transforming operations to the cloud, and the evolution of financial services. The conversation also delves into marke...

  Take the Business Buyer Readiness Assessment →   Summary Nathan Lenahan didn’t just “fall” into success—he fought for it. In this gripping conversation, he reveals the raw, unfiltered truth about the challenges he faced in his early business acquisitions and how a single strategic pivot to HVAC transformed everything. You’ll hear how Nathan overcame growth roadblocks, built a powerhouse team, an...

  Take the Business Buyer Readiness Assessment →   Summary Michael Ly reveals how he built Reconciled from the ground up and then acquired 3 more accounting firms. Discover his secrets to scaling with outsourced accounting, cold email outreach, and using tech to streamline the workload. He uncovers the biggest challenges in the accounting industry today—AI, fewer grads, and more. Michael shares in...

  Take the Business Buyer Readiness Assessment →   Summary Adam Coffey discusses the re-release of his book, Private Equity Playbook, and the importance of understanding private equity for entrepreneurs. He explains how private equity works, including the process of raising funds, buying and growing companies, and generating returns. Coffey emphasizes the potential for entrepreneurs to use private...

  Take the Business Buyer Readiness Assessment →   Summary Patrick O'Connell, a quality of earnings specialist, discusses the importance of analyzing the true earnings potential of a business before buying or selling. He highlights five red flags to watch out for in a potential deal: pending lawsuits, high employee turnover, inconsistent financials, declining market share, and key dependence...

  Take the Business Buyer Readiness Assessment →   Summary Sam Rosati co-founder of Premier Solutions Group, discusses his experience in acquiring and growing fence companies in the sunbelt region. He highlights the importance of focusing on commercial fencing, which offers larger projects and a competitive advantage. Sam also emphasizes the significance of building a strong team and delegating ta...

  Take the Business Buyer Readiness Assessment →   Summary Meet Robert Kirila and Mark Whaling, the duo behind Black Powder Partners—a game-changing venture that's turning the dream of entrepreneurship into a reality for special forces veterans. Born out of their passion for aiding these heroes as they transition to civilian life, their journey began with Your Grateful Nation, a nonprofit ded...

  Take the Business Buyer Readiness Assessment →   Summary Curious how a veteran chiropractor turned a mid-market acquisition into a $10M net worth?  Henry Silvestriz did just that. Partnering with his corporate-savvy father, they formed Vinci Holdings LLC, spent 21 grueling months in search and due diligence, and finally secured a top-tier medical company. Now at the helm, Henry shares insider se...