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

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Investing, Business, Technology

4.8 • 2.4K Ratings

🗓️ 26 August 2025

⏱️ 148 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- 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) The Alpha School Revolution (00:12:47) Personalized Learning with AI (00:35:51) Motivating Students: The Key to Success (00:42:06) Life Skills Workshops: Real-World Learning (00:44:48) Scaling Personalized Learning (00:47:47) High Standards and Student Motivation (00:52:33) The Role of Guides and Coaches (00:58:22) Feedback Loops and AI in Education (01:17:52) Filling Knowledge Gaps in Education (01:20:15) Changing Perceptions of Academic Ability (01:28:20) Challenges in Public School Systems (01:31:16) Entrepreneurship in Education (01:41:56) Gamified Learning and Technology (01:55:05) Efficiency Gains in Software Systems (01:59:48) Transition to a Private Life (02:01:21) Trilogy (02:10:39) Lessons from Mentors (02:17:25) Pushing Limits and Finding Passion (02:24:22) The Future of Education (02:27:12) The Kindest Thing

Transcript

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0:00.0	The best operators have a relentless focus on leverage, finding ways to multiply their impact
0:04.7	rather than just working harder. But here's what I see happening in finance teams everywhere,
0:09.0	brilliant people getting buried in expense management busy work. If you think about it,
0:12.8	you become a finance leader because you love strategic work, modeling scenarios, optimizing capital
0:17.2	allocation, finding the insights that actually move the business forward. But instead,
0:20.8	you're chasing receipts and categorizing transactions.
0:23.1	It's the opposite of leverage.
0:24.8	This is exactly why I'm so bullish on what the team at Ramp has built.
0:28.5	Kareem and Eric understood that every minute spent on manual expense management is a minute
0:32.4	stolen from high leverage work.
0:34.0	So they automated all of it.
0:35.6	Automatic categorization, receipt matching, spending controls that
0:38.6	actually work. I love the network effect that this creates. When finance teams at companies like Shopify
0:43.7	and Stripe automate the mundane stuff, they free up cycles to think bigger, to ask for your questions,
0:48.5	spot patterns others miss, and make the kind of strategic bets that separate great companies from good
0:53.0	ones. The math is simple. Get your time back, focus on what matters.
0:57.2	Check out ramp.com slash invest and see what happens when you eliminate the busy work.
1:01.9	In asset management, growth often depends on customization.
1:05.9	It's the nature of the beast in our industry, and I know having experienced the problem firsthand.
1:10.7	As an active manager,
1:11.6	it's a competitive differentiator to tailor products and services to clients' preferences, and we
1:16.4	want to say yes. When we say yes, it means delivering a tailored portfolio, a tailored report,
	...

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