Transforming and Selling Businesses with Alexis Sikorsky

This week, Dan sits down with Alexis Sikorsky, founder of Knight Scale Partners, to unpack how to build, transform, and exit companies the smart way. Alexis shares the strategy behind "moving like a knight," a crisp 3–4 year planning window with one-month reaction time, the metrics he watches, and the story behind selling his banking software company, why he took 85% cash / 15% earn-out, and how the earn-out ended up paying more. If you want a practical playbook for scaling value without losing your mind (or your house during a crisis), this is it. Show Highlights: Why the knight? Strategy behind Knight Scale Partners—anticipate, "play with the whites," and win by moving differently. [00:03:02] The planning horizon that actually works: 3–4 years…with a one-month reaction time for pivots. [00:06:12] What to measure: start with TAM, then track LTV/CAC monthly—keep the dashboard simple. [00:11:05] Start with the founder's goal: the surprisingly universal number is $40M and why. [00:17:23] (derived from the transcript section referencing "40 million") 2008 hits: lost 75% of revenue in a day—and the seven-year grind back. [00:26:23] The deal that changed everything: 85% cash / 15% earn-out up front… [00:30:44] …and why the earn-out paid more than the cash. [00:31:10] What great PE actually brings: cost discipline and world-class sales; why "no sales team" is a PE dream. [00:32:02] Alexis' two superpowers: leadership and turning complexity into five actionable steps. [00:56:27] "Black Dragons" (a.k.a. Black Swans): build 9 months of war chest and design for agility. [00:49:56] What Alexis reads for complex thinking: The Three-Body Problem (and The Dark Forest). [00:56:49] Cashing Out: Alexis' simple method to go from ~$10M to $100M valuation; audiobook now available. [00:56:58] The Virtual C-Suite: fractional, high-caliber execs as an unfair advantage; early traction & LTV/CAC math. [01:07:03] For more updates and my weekly newsletter, hop over to https://betterquestions.co/ To learn more about Alexis Sikorsky, check out the websites below:  https://www.knightscalepartners.com/  https://www.linkedin.com/in/alexis-sikorsky-consulting/?originalSubdomain=uk