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Stop Ripping Out Your Legacy Code with Alan Williamson, CTO

August 24, 2026 · 43 min

Show notes

Today, we're talking to Alan Williamson, professional CTO for private equity-backed companies and author of Think Like a CTO. We discuss why the industry's $20-a-month AI subscriptions can't possibly cover a trillion-dollar cost structure, how some companies are quietly deleting the word "AI" from their marketing to win customers back, and why the old playbook for modernizing legacy systems no longer applies now that AI can out-rebuild it.

All of this right here, right now, on the Modern CTO Podcast!

To learn more about Alan Williamson, check out his website here https://thinklikeacto.com/


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