Invest Like the Best

Key Takeaways

Personalized, mastery-based learning (driven by AI) can enable students to learn 10x faster, mastering material in just two hours a day and freeing up time for real-world skills, entrepreneurship, and personal interests
Motivation is essential: Kids must love school for it to be effective. The greatest motivator is giving students time back in their day, achieved by efficient mastery learning.
Time-based, lecture-driven models leave knowledge gaps: Most U.S. students plateau in middle school, as traditional education pushes content too fast, resulting in a fragile “swiss-cheese” learning foundation
AI’s transformational role: With generative AI, obsolete textbooks and one-size-fits-all instruction are replaced by continuous, adaptive, and personalized feedback, tailored to each learner’s interests and needs.
Feedback and growth mindset are superpowers: Receiving and seeking feedback in school builds resilience, accelerates learning, and prepares students to thrive beyond the classroom
High standards + high support = success and happiness: Kids grow most when challenged and held to ambitious goals with strong mentoring, even if the process is uncomfortable.
Gamification and engagement: Applying video game design and motivation mechanics to education can make learning irresistible, turning hard tasks into meaningful and fun challenges
No one-size-fits-all: Multiple school types, customized daily schedules, and teaching entrepreneurship, leadership, and teamwork ensure education aligns with each child’s unique strengths and ambitions.
“I think this is one of the coolest projects happening in America that people are just starting to learn about.” – Patrick O’Shaughnessy on Alpha School

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

Joe Liemandt - Building Alpha School, and The Future of Education - [Invest Like the Best, EP.439]

Podcast Notes Playlist: Business