About this episode

Kyle Brown shares insights from his investment banking experience on evaluating business acquisitions and recognizing overlooked opportunities.

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…

More episodes of Buying Online Businesses Podcast

• The Financing Trap That Kills Online Business Deals Before They Even Close with Ami Kassar · July 15, 2026 · 37 min
• $600K Ecom Deal Acquisition + Why Most Buyers Can't Get a SBA Loan to Buy An Online Business with Jared Johnson · July 8, 2026 · 38 min
• Flippa's New CEO: Why AI Is Actually the BEST Reason to Buy an Online Business Right Now with Tony Xu · July 1, 2026 · 42 min
• Why Most SEO Agencies Are Lying to You About AI and What to Do Before It's Too Late with Steve Wiideman · June 24, 2026 · 41 min

Explore listener stats, chart rankings, contacts and more on the Buying Online Businesses Podcast podcast page.