#21 - Boots on the Ground: How Early UBER Employee Nick Mathews Built Boston | The Early Podcast

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

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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.

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