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
