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

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Feb 27, 2026

JD Ross, serial entrepreneur who co-founded Opendoor and now leads AI-first WithCoverage. He talks about how AI is sparking a new invention era. Conversation covers modernizing insurance brokerage with AI and human teams, how AI reshapes software and engineering workflows, and why this moment is especially promising for new builders.

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ANECDOTE

Early Moving Company Turned Real Business

JD Ross bought a small college moving company and scaled it into a multimillion-dollar business that still operates today.
By graduation ~10% of the college had worked for him, giving him early deal flow and practical operational experience.

INSIGHT

Homes As Commodities Enables Digital Transactions

Opendoor treated most homes as commodities that can be valued sight unseen, enabling digital buy/sell experiences for the middle 80% of houses.
The approach focused on delivering superior service and operationalizing valuation to replace friction in traditional real estate transactions.

ADVICE

Replace Brokers With Platformized Risk Management

Replace brokers by offering a modern risk management team plus a digital platform and sell directly to customers with measurable savings.
WithCoverage automates servicing (certificates, claims, placements) and promises 10–30% savings to customers while capturing commission margin improvements.

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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 — 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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