Ep 143: JD Ross on the New Invention Era & Building with AI in 2026

JD Ross is one of my favorite entrepreneurs. I hired him out of college at Addepar where he quickly became Head of Product. He went on to co-found Opendoor with Keith Rabois and is now building WithCoverage (withcoverage.com) — one of the fastest growing AI-first service companies. JD believes we're entering an "invention era" again. What are the new possibilities with AI? What does it mean for legacy software companies? And why is he especially excited for young talent entering the workforce today?We discuss all this and more, starting with JD's entrepreneurial journey, from founding a moving company in college (that still generates +$10M a year in sales!) to joining Addepar and later founding Opendoor. We discuss some of the breakthroughs and challenges at Opendoor, and why its meme stock moment is infusing new energy and ideas into the company. Next, we dive into WithCoverage and his mission to upend the insurance brokerage industry by combining new AI tools with human expertise — think Ramp for risk management. Initially backed by 8VC, WithCoverage already serves more than 700 enterprise customers and recently closed a $42 million round led by Sequoia and Khosla Ventures. Talented builders like JD are scaling and iterating on new products faster than anything we've seen before — learn what this means for the startup ecosystem, as well as existing SaaS companies looking over their shoulders. Finally, JD explains how AI is leveling the playing field and why he believes this is the best opportunity for new entrepreneurs in recent decades.
00:00 Episode intro
01:28 JD's entrepreneurial journey
05:18 Wins and challenges at Opendoor / meme stock moment
09:55 WithCoverage and upending insurance brokerage with AI
13:11 Mimetic frameworks for entrepreneurs
15:45 How AI is changing the way companies are built
20:21 The impact of AI on existing SaaS
26:50 How to stop AI spam and imposters
31:27 How should young people prepare for the AI era?
34:20 The new invention era / why AI levels the playing field

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