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Class Dismissed - Colossus

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Even after agreeing to break his silence after 25 years, Joe Liemandt is still reluctant to talk about himself. It’s hard to get him to relive Trilogy, the enterprise software company he founded in 1989, which by age 27 put him on the cover of Forbes, twice, as America’s youngest self-made centimillionaire. He isn’t keen to expound on SalesBuilder, Trilogy’s flagship expert system from the 1990s and the world’s first billion-dollar artificial intelligence product in all but name. Ditto ESW, the investment arm of Trilogy that’s acquired hundreds of software companies since 2000 and helped make him a decabillionaire, yet the mention of which makes the otherwise inexhaustible Liemandt, who always seems to be straining at some invisible leash, seem drowsy and bored. Nor is he interested in dwelling on his reputation as a tech pioneer in everything from expert systems to manufacturing configuration, college recruitment, corporate boot camps, “tech bro culture,” remote work, monitoring worke

Class Dismissed - Colossus Loading Search Podcasts Invest Like the Best Business Breakdowns Founder’s Field Guide Joys of Compounding Founders 50X Magazine Newsletter About Us Sponsors Subscribe Log in Copyright © 2026 Colossus. All rights reserved. Profile Class Dismissed As an elementary school principal, a feared software tycoon, a genial recluse, and a technology zealot determined to redefine childhood for mankind, Joe Liemandt is many things that shouldn’t go together—and a human Rorschach test for what we care about most By Jeremy Stern August 2025 Issue 04 PHOTOS BY DREW ANTH

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