What Investment Bankers Know About Buying Businesses That Regular Buyers Will Never Figure Out Exists with Kyle Brown
Buying Online Businesses PodcastShow Notes
Most people buying businesses are looking for the obvious. The obvious growth. The obvious profit. The obvious opportunity. That's exactly why they miss the best deals. Kyle Brown spent years in investment banking and private equity evaluating acquisitions before ever buying a business himself. And what he learned was simple: The businesses that look the safest aren't always the best investments. And the businesses that look broken aren't always broken. When Kyle came across an ecommerce business that was barely breaking even, most buyers would have walked away. Declining performance. Frustrated owners. Uncertain future. On paper, it looked risky. But Kyle wasn't looking at the same things everyone else was. In this episode, Jaryd sits down with Kyle to unpack how investment bankers evaluate opportunities, how private equity investors think about risk, and how to value a business when traditional formulas stop working. They discuss why so many buyers become obsessed with multiples, how distressed businesses can create outsized returns, and the operational changes that helped turn a struggling acquisition back into a profitable company. But perhaps the biggest lesson is this: Buying a business isn't about finding perfection. It's about seeing something everyone else has missed. Most buyers never learn how to do that. Kyle did. 🎧 Hit play to discover what investment bankers know about buying businesses that regular buyers will never figure out exists.
Episode Highlights 03:36 - How a Kid From an 800-Person Farming-Town High School Broke Into Investment Banking and Private Equity 07:03 - The $1M-$3M EBITDA Businesses His Family Office Targeted — And Why HVAC Became Their Favorite Acquisition Category 08:29 - The 25-Year-Old Who Took Over a Newly Acquired Ecommerce Business Just 30 Days After the Seller Walked Away 12:12 - How an 8-Year-Old Relationship Led to an Off-Market Acquisition Opportunity Nobody Else Saw 16:09 - The Break-Even Business Dilemma: How He Valued a 7-Figure Revenue Company When EBITDA Was Essentially Zero 20:14 - Why a Business That Once Generated $500K+ in Earnings Could Suddenly Be Worth Just 1x SDE 26:00 - The Turnaround Strategy: How Adding Customer Service, Sales Processes, and Accountability Took the Business Back to Profitability 30:14 - Why He Refuses to Build a Fund, Raise Millions, or Chase a Big Exit Despite Having the Background to Do It
Key Takeaways ➥ The best acquisition opportunities rarely look perfect. Kyle bought a business that was essentially breaking even because he focused on what it could become, not just what it looked like on closing day. ➥ Investment bankers don't just analyze numbers - they analyze risk. Revenue, profit, and multiples matter, but understanding why a business is struggling is often far more valuable than the financial statements themselves. ➥ A declining business gets discounted twice. First through lower earnings, and then through a lower valuation multiple. That's why turnarounds can create outsized returns for buyers who know how to fix the underlying problems. ➥ Relationships create opportunities that search never will. Kyle wasn't actively looking to buy a business when the deal appeared. An eight-year relationship and a consulting conversation led to an off-market acquisition most buyers would never have seen. ➥ You cannot improve a business you don't understand. Before hiring people or changing processes, Kyle answered customer calls himself, learned the products, and got into the weeds of the operation. The best operators understand the front lines before they build systems. ➥ Most struggling businesses don't need a miracle. They need execution. Answering the phone, following up with customers, building a sales process, improving accountability, and fixing neglected marketing channels can have a bigger impact than any growth hack. ➥ Buying a business can feel like buying yourself a job at first. The goal isn't to avoid work
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