Why This CEO Refuses to Retire: Simon Haighton-Williams on Risk, Honesty, and Building a Business You Never Want to Leave
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Why This CEO Refuses to Retire: Simon Haighton-Williams on Risk, Honesty, and Building a Business You Never Want to Leave
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James sits down with Simon Hayton-Williams, CEO of Adaptivist, to unpack 15 years of high-speed company building. Simon shares how a free tool built by one obsessive developer became a $100M ARR business, why brutal honesty with clients (even when it costs you the deal) builds lasting trust, and the exact headcount thresholds (100, 400, 1,000+ people) where everything breaks and has to be rebuilt.
They dig into:
Why Adaptivist's growth came from "earning the right" to plan for the future by first putting out fires
The emotional reality of acquisitions - and why founders often leave within two years
Simon's philosophy on delegation vs. co-creation, and why he refuses to hire "yes people"
Why he believes "all org charts are interim" and how his "greenhouse" model incubates new teams
Balancing 30+ years in software with scuba diving, sports cars, and single parenthood
Find Simon here: https://www.linkedin.com/in/simonwilliams/
Find Adaptavist here: https://www.adaptavist.com/
Find ScriptRunner here: https://www.scriptrunnerhq.com/
Find James here: https://bloomcoach.uk/