Ep 525 How to Know When to Get Out: What to do when Shopify threatens, Selling vs. hiring a CEO. A controlled process instead of massive auction and getting your cash up front.

Ep 525 How to Know When to Get Out: What to do when Shopify threatens, Selling vs. hiring a CEO. A controlled process instead of massive auction and getting your cash up front.

Author: John Warrillow December 19, 2025 Duration: 26:01

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 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 


For any entrepreneur, the idea of selling the company they've built is both a daunting prospect and a potential pinnacle of success. Built to Sell Radio, hosted by John Warrillow, steps into that complex space with a clear, practical focus. This isn't about abstract theory; it's a weekly conversation grounded in real experience. Every episode features a different founder who has recently navigated the sale of their business. The discussion goes straight to the heart of the matter: understanding the personal and strategic reasons behind the decision to sell. Listeners get an honest breakdown of what worked, from preparation and valuation to negotiation, and perhaps more importantly, the unforeseen pitfalls and mistakes made along the way. It’s that candid post-mortem, the lessons learned in the trenches of a transaction, that provides unparalleled value. By compiling these firsthand accounts, the podcast builds a comprehensive library of exit strategies and cautionary tales. Tuning in feels like gaining access to a private mastermind, where seasoned entrepreneurs share the unvarnished truth about cashing in their life's work. If you're contemplating your own eventual exit, this series offers the nuanced, peer-to-peer insights you need to think like a buyer, protect your interests, and ultimately, build a business that is truly desirable. Built to Sell Radio serves as an essential guide, transforming the opaque process of selling a business into a clearer, more manageable journey.
Author: Language: English Episodes: 100

Built to Sell Radio
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