Connor Mitchell: I’ll put you where you can fail, but I won’t let you drown.

On this episode, Kevin chats with Connor Mitchell, Managing Director at Cascadia Capital, the #2 independent investment bank in the nation, about selling founder-led businesses in the human capital and professional services sector. Connor works with companies valued between $100MM and $350MM, with 65% of Cascadia's business coming from family and founder-led companies. The conversation unpacks why many founder-led businesses struggle to sell and the mindset shifts that accompany liquidity events, covering where the market is trading today, how buyers create value post-acquisition, and why selling is less about "can I sell" and more about whether the price justifies walking away. Connor explains the objective measures sellers should consider before going to market—like the mix of 1099 versus W2 employees, customer concentration, employee utilization rates, and percentage of business originated by the founder—along with what Quality of Earnings is and why it matters. They discuss the typical timeline from building a deck to closing, why a soft touch on sales beats blasting deal memos everywhere, and the importance of putting a plan in place if a sale is truly where you want to land.