How to Know When to Get Out with Ryan O’Leary
- Kyle Winder
- Dec 22, 2025
- 2 min read
About This Episode
If you’re feeling a little queasy about the pace of change, you’re not alone. AI is accelerating competition in almost every market, and it’s making some business models feel irrelevant almost overnight.
In this episode of Built to Sell Radio, John Warrillow talks with Ryan O’Leary, who saw a similar wave coming in payments when Shopify started bundling merchant processing into its plans. O’Leary chose to sell before the shift crushed margins, structuring a deal that put most of his cash in hand up front.
In this episode, you discover how to:
Decide whether to raise capital, hire a CEO, roll equity, or sell
Spot the early signals that a platform is about to “bundle” you into irrelevance
Run a tight sale process with a short target list and still generate multiple LOIs fast
Negotiate for a deal structure that protects you, not just a higher multiple
Limit earnout risk by keeping the earnout short and the rules hard to game
Separate emotion from the numbers so you can negotiate clean
Keep your team aligned through the transition by sharing upside, including the earnout
About Our Guest
Ryan O'Leary
Ryan O’Leary is the founder of Sona, a payment processing platform built to simplify and modernize how businesses handle transactions.
As an entrepreneur with deep experience in fintech, Ryan built Sona to solve real operational pain points around payments, scalability, and reliability. His work focuses on creating infrastructure that helps businesses move money more efficiently while reducing complexity behind the scenes.
Definitions
Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.
Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.
Roll Over Investor: A rollover investor, in the context of selling a business, refers to an individual or entity that rolls some of their proceeds from the sale with the buyer. This strategy allows the seller to defer capital gains taxes and potentially leverage their expertise or resources in a new venture.
Re-Trading: This occurs when a buyer attempts to renegotiate the purchase price of a deal after initially agreeing to one. It is often seen unfavorably as it occurs after due diligence, seemingly exploiting newly discovered information.
TAM: “Total Addressable Market.” It’s a business term that represents the overall revenue opportunity available for a product or service in a specific market. To put it simply, TAM is the maximum amount of money a company could potentially make if they captured every single customer in a given market who might be interested in what they’re selling.
The Transfer of your Business may be the Biggest Financial Transaction of your Life.
At Flight Plan Strategies, we utilize ExitMap® to help Business Owners understand their current level of preparedness so that they can begin the succession planning process.
