Transforming and Selling Businesses with Alexis Sikorsky, Part 2

This week, Dan picks up with Alexis Sikorsky—entrepreneur, investor, and founder of Knight Scale Partners—for the tactical follow-through: what great private equity actually brings, how to replace yourself post-acquisition (“please chairman me”), why agility beats prediction in a world of Black Swans/“Black Dragons,” and how agencies can still win as AI re-sorts the field. If you’re navigating uncertainty, planning pivots, or gearing up for an exit, this continuation is packed with clear plays and hard-won context.

Show Highlights

• What great PE actually brings: cost discipline, better people, and world-class sales—why the dream target has a weak or no sales team. [00:00:49]
• “Please chairman me”—why Alexis replaced himself as CEO and why being chairman can be the best job in the world. [00:02:07]
• Exit math that stuns: sold remaining shares for an undisclosed nine figures; two years later buyers resold for +60%, ~16× cash multiple. [00:02:36] [00:03:03]
• Retired, then Oxford: why he went back to school, started advising (even pro bono), and turned mistakes into a playbook. [00:03:52]
• Two superpowers: leadership (not management) and turning complexity into five actionable steps. [00:06:44]
• Triple headwind case study: clients dying, business model dying, channel dying—plus “Google is in panic.” [00:11:06]
• Pivot playbook: keep your domain (e.g., real estate), expand geographies, diversify inbound (podcasts/LinkedIn), and add warm outbound. [00:13:28] [00:14:41]
• AI won’t erase agencies—it will empower fewer winners (think 6,000 → 600); VCs shifting to AI-enabled efficiency. [00:15:28]
• Black Swans (“Black Dragons”): don’t time them—build agility and expect a crisis about every decade; a leveraged-forex cautionary tale. [00:17:36] [00:18:38]
• War-chest rule: keep ~9 months of burn so shocks don’t kill you. [00:20:14]
• Sci-fi as systems training: Asimov and a love letter to The Three-Body Problem (especially the brutal Book 3). [00:21:58] [00:23:33]
• Cashing Out: a simple method to go from small to less small—and how to speak private equity. [00:24:54]
• Where to find him: Knight Scale Partners (with a K), LinkedIn, and Instagram—unique name makes him easy to find. [00:26:56]

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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