My guest today is Joe Liemandt. Joe is the Principal at Alpha School and the founder of Triliogy Software and ESW Capital. He became the youngest member of the Forbes 400 in the 1990s before vanishing from public view for two decades—only to emerge with a $1 billion bet that he can make kids learn 10x faster using AI. Joe has built an AI tutoring system so effective that students at his Alpha School literally beg not to take summer breaks, achieving 2x learning outcomes in just 2 hours with standardized test results that compete with the best of them.

We dive deep into why this could be the most valuable product he's ever built, his contrarian thesis that traditional SaaS is facing AI-driven obsolescence, and how his experience buying 100+ software companies prepared him for this moonshot in a trillion-dollar market that hasn't innovated in 200 years. For investors, this is a masterclass in deploying patient capital to rebuild broken systems from first principles, with insights on everything from regulatory moats to the intersection of AI and human psychology.

As your excited skeptic, I push hard on the technology readiness, parental adoption hurdles, and whether this audacious vision can actually scale to a billion kids. Additionally, in a Colossus Profile released last week, our editor-in-chief Jeremy Stern reported, for the first time, Joe as the product guy behind Alpha School in a can’t miss piece of writing. And now please enjoy my conversation with Joe Liemandt.

Joe Liemandt’s Colossus Profile by Jeremy Stern.

For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠

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Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠).

Show Notes:

(00:00:00) Welcome to Invest Like the Best
(00:06:08) How Alpha School Is Revolutionizing Learning
(00:12:47) Personalized Tutoring with AI
(00:19:59) Measuring the Impossible: 2x Learning Outcomes
(00:25:39) All Educational Content Is Obsolete
(00:35:51) Motivating Students: The Key to Success
(00:42:06) Life Skills Workshops: Real-World Lessons
(00:47:47) The Key to Happiness: High Standards
(00:52:33) The Role of Guides and Coaches
(00:58:22) Feedback Loops and AI in Education
(01:04:20) The AI-Powered Classroom Experience
(01:18:06) From Self-Doubt to Limitless Learning
(01:28:20) Challenges in Public School Systems
(01:41:56) Gamified Learning and Technology
(01:49:46) From Trilogy to Trillion-Dollar Markets
(01:55:05) Why Software Companies Fail
(02:01:21) Trilogy University
(02:10:39) Lessons from Mentors
(02:17:25) Pushing Limits and Finding Passion
(02:27:12) Joe's Kindest Thing

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