
#21 - Boots on the Ground: How Early UBER Employee Nick Mathews Built Boston | The Early Podcast
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This week's guest: Nick Mathews, an early Marketing Manager and launcher of Uber in Boston.
What does it take to build a global giant, one city at a time? Nick was on the ground fighting taxi cartels, throwing ice cream stunts, and building Uber’s Boston launch playbook from scratch. In this episode, he shares raw stories about Uber’s early street fights, local marketing hustle, and what he learned starting his own company, MainVest.
✅ Inside this episode:
• Boots-on-the-ground tactics that built Uber city by city
• Early growth hacks: neon tank tops, ice cream trucks & local stunts
• Why Uber fought regulators — and won with community support
• The secret power of city teams, data, and local autonomy
• Lessons from MainVest: what happens when a startup fails
Subscribe for more conversations with early employees behind the world’s biggest startups.
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⏱️ Chapters
00:00 Intro
01:25 Growing up in Massachusetts & punk rock bands
04:30 Early lessons in hustle and marketing
07:45 Getting hired at Uber through friends at Facebook
10:00 Uber’s secret Boston launch & Halloween chaos
14:30 Boots on the ground: local marketing & community building
18:20 Fighting taxi cartels & local regulators
23:40 Uber Ice Cream & neon tank tops
28:10 Weekly staff calls & city team experiments
33:00 Culture lessons: local autonomy & data obsession
37:30 When Uber almost got shut down
40:00 Why Uber’s local teams worked
44:00 Founding MainVest & lessons from failure
50:00 How to handle setbacks & learning to detach identity
54:00 Nick’s biggest takeaways: everything is marketing, local always wins
57:30 What’s next for Nick
59:00 Closing thoughts & Mike Rowe’s TED talk
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🎙️ ABOUT THE SHOW:
The Early Podcast is where host Max Crowley, Uber’s #25 employee, sits down with the earliest builders behind today’s most iconic companies. No fluff, just the raw stories of what it’s like in the trenches when your startup could still fail tomorrow.
✅ Subscribe for more untold startup stories every week
✅ Like, comment & share if you know someone interested!
✅ Listen on Spotify, Apple, or anywhere you get your podcasts
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Let’s go. 💥
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