Joe Liemandt  - Building Alpha School, and The Future of Education artwork

Joe Liemandt  - Building Alpha School, and The Future of Education

Invest Like the Best with Patrick O'Shaughnessy

August 26, 2025

My guest today is Joe Liemandt. Joe is the Principal at Alpha School and the founder of Triliogy Software and ESW Capital.
Speakers: Patrick O'Shaughnessy, Joe Liemandt
**Patrick O'Shaughnessy** (0:00)
The best operators have a relentless focus on leverage, finding ways to multiply their impact rather than just working harder. But here's what I see happening in finance teams everywhere. Brilliant people getting buried in expense management busywork. If you think about it, you become a finance leader because you love strategic work, modeling scenarios, optimizing capital allocation, finding the insights that actually move the business forward. But instead, you're chasing receipts and categorizing transactions. It's the opposite of leverage. This is exactly why I'm so bullish on what the team at Ramp has built. Kareem and Eric understood that every minute spent on manual expense management is a minute stolen from high-leverage work, so they automated all of it. Automatic categorization, receipt matching, spending controls that actually work. I love the network effect that this creates. When finance teams at companies like Shopify and Stripe automate the mundane stuff, they free up cycles to think bigger, to ask bigger questions, spot patterns others miss, and make the kind of strategic bets that separate great companies from good ones. The math is simple. Get your time back, focus on what matters. Check out ramp.com/invest and see what happens when you eliminate the busy work. In asset management, growth often depends on customization. It's the nature of the beast in our industry, and I know having experienced the problem firsthand. As an active manager, it's a competitive differentiator to tailor products and services to clients' preferences, and we want to say yes. When we say yes, it means delivering a tailored portfolio, a tailored report, or a tailored expectation for service. Saying yes leads to growth, and it also creates customization and a trade-off. The more you grow, the more complexity you absorb. The more you say yes, the harder it is to scale efficiently and consistently. That's where Ridgeline comes in. Ridgeline automates customization. It gives asset managers the ability to deliver personalized experiences at scale without adding headcount, manual work, or operational risk. Having been an early design partner myself, I saw firsthand the power of taking an entirely clean sheet of paper to building the system we've all been waiting for. It's how leading firms stop choosing between growth and efficiency and start saying yes to both. I believe the best firms will be built on Ridgeline as their operating system. I also believe they will be a leading case study in the combined power of systems of record and AI. If you haven't spent time with them yet, I urge you to see what Ridgeline might unlock for your business. As an investor, gaining an edge means having the right tools, and one platform leading the way is AlphaSense. Trusted by 75% of the world's top hedge funds, AlphaSense is the market intelligence platform that gives institutional investors access to over 500 million premium sources, from company filings and broker research to news, trade journals and more. And with its recent acquisition of Tegus, it also includes the world's largest library of expert interview transcripts, over 200,000 calls covering more than 24,000 public and private companies. All in one platform so investment teams can move faster, go deeper and make high conviction decisions with confidence. Now AlphaSense is transforming the research process with the launch of its deep research tool. Part of the next generation of its AI-powered platform. Unlike other deep research tools, AlphaSense's version is purpose-built for investment research. It runs multi-step iterative analysis using AlphaSense's proprietary content, including those 200,000 expert transcripts, and in minutes surfaces insights that would take multiple interviews and days of digging to uncover. It's like adding 10 analysts to your team, helping you accelerate analysis, deepen understanding and make sharper decisions. See it in action at alphasense.com/invest.
Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus Review along with all of our podcasts at joincolossus.com.

**SPEAKER_2** (3:50)
Patrick OShaughnessy is the CEO of PositiveSum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of PositiveSum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of PositiveSum may maintain positions in the securities discussed in this podcast. To learn more, visit PSUMVC.

**Patrick O'Shaughnessy** (4:19)
My guest today is Joe Lamont. Joe is the principal at Alpha School and the founder of Trilogy 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 10 times 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 two times learning outcomes in just two hours with standardized test results that compete with the very best schools in the world. 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 plus software companies prepared him for this moonshot in a trillion dollar market that hasn't been innovated on 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 modes to intersection of AI and human psychology. I try to be the excited skeptic here. I push hard on the technology readiness, parental adoption hurdles, and whether this audacious vision can actually scale to a billion kids. 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 and a can't-miss piece of writing. It's one of my favorite things that I've read in a very long time, and you can find a link to it in the show notes. I'll leave you with one of my favorite ideas of Joe. He's convinced that across major disciplines, a new instrument often unlocks tremendous progress, whether that be the microscope, the telescope, or the analytical balance. He's convinced that generative AI is that instrument for learning science, and that as a result, we will be able to deploy this incredible knowledge to make our kids and ourselves learn faster and better than ever before. Please enjoy this great conversation with Joe Liemandt.

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