Principled Confrontation – Episode 7 with Rachel Holt
Big things start small. The Early Podcast. Stories and insights from early employees and innovators who’ve shaped the future.
Rachel Holt Doesn’t Mess Around
A conversation about growth, making it happen & going from zero to Uber.
When you think of Uber’s early days, you probably think of San Francisco, black cars, surge pricing, and Travis Kalanick. But one of the fiercest and most important battles Uber fought? It happened in Washington, D.C. and Rachel Holt was on the front lines.
In this week’s episode of Early, I sat down with Rachel—my first in-person guest, live from New York—to unpack her incredible journey: from Bain and Clorox to launching Uber D.C. with zero playbook and a box of iPhones.
We talk about the time an 83-year-old taxi commissioner requested an Uber just to have it impounded in front of the press. How Rachel had never hired a lawyer before—but figured it out. And how she scaled Uber’s U.S. and Canada business to nearly half the company’s global revenue.
🚫 No legal team.
📦 No launch playbook.
💪 Just grit, instincts, and a relentless drive to win.
Rachel worked side-by-side with Travis during Uber’s most intense regulatory fights, helped define the distributed GM model that so many startups now copy, and later ran Uber’s mobility business, including the Jump acquisition and micro-mobility push.
Today, she’s the co-founder and Managing Partner at Construct Capital, a venture fund managing hundreds of millions of dollars and backing the next wave of builders in mobility, supply chain, and real-world tech.
She’s the kind of operator who doesn’t wait for a playbook—she writes it.
Why you should listen:
What it was really like working with Travis Kalanick
How to lead when you’ve never done the job before
What Uber’s rise looked like from the inside
How Rachel reinvented herself after Uber and found purpose in venture
What great founders have in common—and how she backs them
Where to Listen:
🎧 Listen on Spotify
🍎 Listen on Apple Podcasts
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THIS was episode SEVEN! New episodes (at least) every Tuesday, and I’d love your feedback on who we should interview next. Email me: max@earlypod.com
Let’s go!!!!! 🚀
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