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.
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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.

26:01 Dec 19, 2025
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"
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