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 business units while maintaining rigorous financial standards. The discussion highlights the importance of long-term thinking, frugality, and the cultivation of a strong company culture that values autonomy and stewardship over short-term gains.

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 powerfulThe legal landmines that can kill your QSBS eligibilityHow to set up a C-Corp to acquire a business and still qualify Why compliance isn’t optional—it’s everythingThis might be the most overlooked tax strategy in SMB acquisitions right now.

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 Founder05:38 Scaling with Walmart11:26 Raising Capital & COVID Pivot17:06 Acquired by 7-Eleven22:41 EquityX: Buying Legacy Businesses

👉 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 talk due diligence, adbacks, cultural fit, SBA financing, and why most buyers blow it before they even submit an LOI.Chapters00:00 Introduction to Business Brokerage and Jackie Hirsch03:01 Jackie's Journey into Business Brokerage05:58 The Importance of Using a Business Broker09:00 Common Mistakes of First-Time Business Buyers11:58 Understanding Financials and Due Diligence15:01 Navigating Seller Motivations and Cultural Fit18:07 The Role of Adbacks in Business Valuation21:10 Quality of Earnings and Its Importance23:53 Market Trends and Buyer-Seller Dynamics32:06 Navigating the Current Market Landscape35:07 The Importance of Buyer Preparedness39:14 Understanding Business Ownership Dynamics40:51 Challenges in Long-Term Deals46:04 Investor Expectations and SBA Regulations49:08 The Shift Towards Online Businesses56:13 Reflections on a Long Career in Business

 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-run manufacturing businesses—with one goal: long-term, boring, predictable cash flow.We’re talkin’:How to build real trust with sellers (not just “run the numbers” and throw out LOIs)Why SBA loans are a powerful tool if you know how to use themThe surprising red flags he watches for in deals (like customer concentration and operational chaos)Why they only target businesses with 30+ employees (and you probably should too)The emotional side of buying businesses—and how to handle it when stuff hits the fanYou’ll also hear why patience beats pressure, how to manage investors the smart way, and why some owners just want a better life… not a better EBITDA.If you want to buy a business—and actually sleep at night after you do—this conversation is for you.Chapters00:00 Introduction to North Park Group01:33 The Formation of North Park Group04:10 Philosophy of Long-Term Ownership08:50 Funding and Investor Relations12:09 The Unique Partnership Model15:59 Acquisition Strategy and Deal Sourcing19:02 Evaluating Potential Acquisitions24:34 Challenges in Small Business Acquisitions33:13 Navigating Business Acquisitions34:51 Understanding Valuation and Offers37:27 The Importance of Patience in Acquisitions40:33 Identifying Consistency in Business43:39 The Lifestyle of Business Owners46:31 Financing and Managing Investors48:25 De-risking Acquisitions54:14 Top Rules for Debt Management58:00 The Emotional Side of Acquisitions

 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 trusts.We talk lessons learned (some the hard way), how to avoid rookie mistakes, and why your network can make or break your next deal.You’ll also hear how Casey’s using tech to gain an edge—and what legacy businesses are hiding in plain sight for anyone paying attention.If you're thinking about buying a business—or want to raise capital without writing a massive check—don’t miss this one.Plus, we dive into what’s happening at the M&A Launchpad Conference and how it’s shaping the future of small business ownership.Chapters00:00 Introduction to Casey Minchew and Equity Launchpad01:41 Understanding Independent Sponsorship04:46 Lessons from the First Acquisition09:56 Navigating Challenges in Business14:35 The Importance of Team and Transparency19:34 Transitioning to Independent Sponsorship24:36 Capital Structure and Deal Sourcing29:57 Building a Business with Integrity35:22 The Journey of Networking and M&A36:16 Navigating Business Acquisitions38:53 The Importance of Networking Capital40:54 Learning from Past Mistakes44:04 Understanding Different Business Models49:18 Compressing Time in Deal-Making51:15 Exploring New Business Opportunities54:15 The Role of Seller Financing55:54 Building Relationships in Business01:02:26 Creating a Community through M&A Launchpad01:04:43 The Future of M&A and Market Trends

 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 checkWhy having your own skin in the game still matters (sorry, no magic button)How to spot businesses that actually attract investors — and which ones scare them offThe biggest red flags investors look for (and how to avoid them)Why SMB investing is exploding right now — and how you can ride the waveHow to get your deal in front of the right investors (instead of getting ghosted)How to position yourself so investors want to work with youIf you’re serious about raising money to buy a business — and you’re tired of bad advice — you’ll want to hear this.Chapters00:00 Introduction to SMB Investor Network02:53 The Need for Equity Injection in SMB Acquisitions06:05 Understanding Investor Preferences and Deal Dynamics09:12 Evaluating Different Business Models for Investment12:00 Challenges in Funding Professional Services Firms15:03 Navigating Personal Capital Requirements for Buyers18:08 Investor Expectations and Myths in SMB Acquisitions24:31 Understanding Financial Discrepancies in Business Valuation26:11 The Importance of Quality of Earnings Reports27:38 Structuring Attractive Terms for Equity Raises30:10 Identifying Red Flags in Investment Deals34:28 The Growing Interest in SMB Investments36:49 The Process of Submitting Deals to SMB Investor Network39:01 Strategies for Generating Interest in Investment Deals41:46 Understanding the Investment Structure and Rights45:17 The Value Proposition for Passive Investors

 Take the Business Buyer Readiness Assessment →  SummaryIn 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, emphasizing the importance of due diligence and strategic planning for potential buyers. The discussion also touches on the resilience of the American market and the potential for future growth despite short-term hurdles.TakeawaysTariffs on Chinese imports are significantly impacting e-commerce.Margins for e-commerce businesses are likely to be squeezed.Prices across platforms like Amazon are expected to rise.Fear mongering about price increases is prevalent but may be exaggerated.Short-term issues may arise, but the market is resilient.Building significant working capital into deals is crucial.Due diligence is more important than ever in acquisitions.Diversifying supply chains can mitigate risks associated with tariffs.Seller notes may increase as a response to tariff impacts.M&A activity remains vibrant despite current challenges.

 Take the Business Buyer Readiness Assessment →  SummaryIf 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, now a business broker who’s seen it all) breaks down:Why most buyers waste everyone's time (and how to not be one of them)What brokers look for in a qualified buyer (hint: it’s not just cash)How valuations really work (and why tax returns matter more than fancy spreadsheets)Why franchises are a different beast (and how to play by those rules)The real reason deals fall apart — and how to avoid itHe even gets into the weeds on:Seller financing (structured right, it’s a cheat code)Cash deals (why they move lightning fast)What markets are 🔥 right now (HVAC, med spas, and more)And here’s the kicker: You’ll hear how he lost every deal during COVID, rebuilt, and what he wishes buyers understood before stepping into a deal.If you’re serious about buying a business,this is a behind-the-scenes look at what brokers know but buyers don’t.And it could save you months of headaches and tens of thousands of dollars.Listen to it. Study it. Use it.

 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 relationships, and turned the business into a profit machine—hitting a ridiculous 73% net margin. No fluff, no corporate nonsense—just smart strategy, efficiency, and knowing exactly how to extract maximum value.Then, when the time was right, she flipped it to private equity.In this interview, Lindsay pulls back the curtain on the whole playbook—how she structured the deal, the mindset shifts that made the biggest difference, and the real emotional rollercoaster of selling a business you built from the ground up. Plus, what she’s doing next now that she’s cashed out.If you want to know how real entrepreneurs buy, scale, and sell businesses for life-changing money—this is the interview you can’t afford to miss.Chapters00:00 Lindsay's Journey to Entrepreneurship02:53 Navigating the Purchase of an Accounting Firm06:01 Overcoming Initial Challenges09:01 Building Efficiency and Client Relationships12:03 The Importance of Valuation in Business15:00 Transforming the Business Model18:01 Maintaining High Profit Margins20:55 The Human Element in Business Success31:21 Balancing Leadership and Friendship32:49 Cultivating Loyalty Through Positive Culture34:29 The Importance of Human Connection in Business36:40 Navigating Burnout and Business Ownership39:44 The Risks of Sole Ownership41:41 The Decision to Sell: Weighing Options43:19 Valuation Challenges in the Accounting Industry46:25 Private Equity and Its Impact on Valuation51:13 Exploring Growth Opportunities vs. Selling53:38 Transitioning Ownership: Lessons Learned