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Edtech Insiders

Why Personalized Education Hasn’t Happened and How Outschool Aims to Fix It with Amir Nathoo & Justin Dent

11 Aug 2025

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Send us a textAmir Nathoo is CEO of Outschool, a marketplace for live online classes for K-12 learners, and an advocate for expanding education access.  Previously, he led product development at Square and co-founded Trigger.io, a platform for creating native mobile apps. Amir holds an MEng in Electrical and Information Sciences from The University of Cambridge and lives in San Francisco with his wife and two children.Justin Dent is the founding Executive Director of Outschool.org. Justin was previously the Founder and Executive Director of Ethos, a nonprofit that provided career education to 18,000 low-income, first generation, or minority students annually. An active voice in the dialogue around education equity, Justin's writing has been featured in the Wall Street Journal and he's appeared on Fox Business, CNBC and Cheddar.💡 5 Things You’ll Learn in This Episode:Why personalized learning remains elusive in traditional education systemsThe overlooked frictions families face when given more choiceHow Outschool uses a marketplace model to serve diverse learner needsThe role of community and trust in enabling educational autonomyHow AI and tech can simplify decision-making for families✨ Episode Highlights:[00:03:00] Amir explains how traditional education systems block personalization[00:06:00] Justin breaks down the real friction points for low-income families[00:11:00] How Outschool’s variety increases motivation and access[00:16:00] Why free resources don’t always lead to usage[00:23:00] Community-driven guidance as a key to family engagement[00:28:00] Outschool’s approach to neurodivergent learners[00:34:00] Systemic flaws in standardization and learning lanes[00:41:00] ESAs and why trusting families is essential[00:45:00] Preventing marketing dollars from skewing family choices[00:49:00] How AI can help families navigate education options😎 Stay updated with Edtech Insiders! Follow our Podcast on:This season of Edtech Insiders is brought to you by Cooley LLP. Cooley is the go-to law firm for education and edtech innovators, offering industry-informed counsel across the 'pre-K to gray' spectrum. With a multidisciplinary approach and a powerful edtech ecosystem, Cooley helps shape the future of education. Innovation in preK to gray learning is powered by exceptional people. For over 15 years, EdTech companies of all sizes and stages have trusted HireEducation to find the talent that drives impact. When specific skills and experiences are mission-critical, HireEducation is a partner that delivers. Offering permanent, fractional, and executive recruitment, HireEducation knows the go-to-market talent you need. Learn more at HireEdu.com. As a tech-first company, Tuck Advisors has developed a suite of proprietary tools to serve its clients better. Tuck was the first firm in the world to launch a custom GPT around M&A. If you haven’t already, try our proprietary M&A Analyzer, which assesses fit between your company and a specific buyer. To explore this free tool and the rest of our technology, visit tuckadvisors.com.

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