Buying and Selling Series: The Operator-to-Owner Path with Stephanie Quay
Most conversations about business acquisition focus on preparing an owner to sell. This episode flips that lens. Brian sits down with Stephanie Quay, founder of Five Experts, whose work centers on preparing a buyer to buy, and unpacks what it actually takes to move through the five phases of acquisition: aspiration, search, deal financing, ownership and value creation, and eventual exit or succession.
Stephanie breaks down why proprietary search tends to outperform brokered deals for many searchers, how to build (and constantly adjust) a buy box without losing focus, and the discipline required to avoid falling in love with a deal before the numbers earn it.
She and Brian also dig into a newer model Five Experts has been piloting: matching searchers directly with founders who are one to three years out from exit, letting an operator step in early, reduce founder dependency, and build value before a sale is ever finalized.
The conversation closes on a simple but often overlooked point: a value creation plan isn't really about the exit. It's about staying exit-ready, whether that means a sale, an ESOP, or just knowing exactly how much more valuable the business has become five years in.
In this episode:
- Why proprietary search creates less competition than brokered deals, and what it takes to source that way
- Building a buy box, and why searchers need to keep adjusting it based on market signals
- The danger of falling for a deal before the diligence is done
- Five Experts' operator-to-owner model: bringing a searcher in years before an exit is signed
- What value creation actually means in practice, beyond growing revenue
- Why passion for the industry may matter more than prior industry expertise
Connect with Stephanie Quay:
- Five Experts: fivexperts.com
- Email: team@fiveexperts.com
- LinkedIn: https://www.linkedin.com/in/stephaniepalmer2/