River Guides

Many owners walk into a business transition focused only on the price. Our guest treats business transactions like a chess game that require thinking several moves ahead.

In the second episode of River Guides, Dewey Hammond, the investment banker behind Eagles to Fly explains why preparation should start early and why the first step is deciding what a successful transaction means well beyond the achieved valuation. He walks through the four stages of a sale, what drives valuation in the lower middle market, and when a full investment bank is worth the fee.

Drawing on about 50 deals from $1 million to $70 million and years of teaching finance at Sewanee and Covenant College, Dewey also shares how to stay resilient when a deal goes sideways, including the client whose largest customer paused orders mid-process and who came back a year later to sell for more.

Connect with Dewey on LinkedIn: https://www.linkedin.com/in/dewey-hammond

Most owners sell a business once. The person across the table has done it dozens of times. In the debut episode of River Guides, Roland Yang, Principal at Trilogy Search Partners opens the buyer's playbook: what a buyer seeks to understand before ever opening the financials, when founder dependence goes from normal to deal-breaking, why the hardest deals to close are often the ones where bad news arrived late, and what separates transitions that work from handoffs that fall apart.

Trilogy Search Partners has spent over a decade backing entrepreneurs who buy one business and run it themselves, serving as lead investor on more than 90 acquisitions. Roland sits on the boards of businesses that have just changed hands, often alongside the founders who sold them, giving him a rare view of what happens after the deal closes.