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

⸻

Let’s go. 💥

🎧 Listen to the full episode:

🔹 Spotify: https://earlypod.com/spotify

🔹 Apple Podcasts: https://earlypod.com/apple

🚀 New episodes drop every Tuesday. Let’s build this together.

👉 Like, subscribe, and drop a comment — I want to hear from you!!

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🚗 Inside the Rideshare Wars: The Untold Story of Lyft vs. Uber 🚗

What really happened when two of the scrappiest startups of our generation collided on the streets, fighting for drivers, riders, and the future of transportation?

In episode # 20!!! of The Early Podcast, we go INSIDE the Rideshare WARS with Nick Greenfield, Lyft’s #4 employee, and the first non-engineer at Zimride (Lyft’s original name) and one of the people who helped pivot it from long-haul carpooling to pink mustaches and everyday rides.

Nick shares:

✅ How they pivoted overnight from Zimride to Lyft when the long-distance carpool model failed

✅ The wild origin story of Lyft’s iconic pink mustache — and why it worked brilliantly until it didn’t

✅ Why Uber’s obsession with driver supply and liquidity crushed Lyft’s idealistic “friend with a car” approach

✅ The real back-channel tactics Uber used to poach Lyft drivers — from “Shave the Stache” ads to mass ride requests

✅ How Stripe Connect was literally built for Lyft to pay drivers — and the $500K overdraft mistake that almost blew it up

✅ The lessons Nick carried into his next ventures — including what makes or breaks two-sided marketplaces, when to pivot hard, and what supply retention really takes

Plus, you’ll get an unfiltered look at the early 2010s San Francisco tech scene:

🌉 $1,100 North Beach rent, Craigslist rideshare hacks, Cake Pop sorority promos at USC, and launch parties that turned into all-night “Balloon View” sessions tracking drivers in real time.

If you love raw startup stories, competitive battle tactics, and the real lessons behind companies that changed how we move — you’ll love this one.

🛫 KEY QUOTES:

“I knew the first 200 riders by name. That’s how scrappy we were.”

“Uber was ruthless — they didn’t just compete for riders, they competed for our drivers.”

“Supply is king in marketplaces. If you don’t own supply, you’re dead.”

“Zimride to Lyft to Lyft Line — pivots saved the company.”

🎧 CHAPTERS:

0:00 Intro — The Peace Offering: Uber + Lyft in the same room

5:30 Zimride’s early mission & the Stanford founder pipeline

10:00 Why the original long-haul rideshare failed in the US

15:00 Pivot to Lyft & the birth of the pink mustache

20:00 The brutal reality of acquiring drivers — and why Craigslist was gold

30:00 Uber’s competitive tactics: “Shave the Stache” & driver poaching

38:00 The inside scoop on Stripe Connect’s creation (and how it broke)

45:00 The real power of community in a marketplace

50:00 Nick’s biggest lessons for founders: pivots, supply, and learning when to stay or leave

⸻

🎙️ 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 who still debates Uber vs. Lyft

✅ Listen on Spotify, Apple, or anywhere you get your podcasts

⸻

Let’s go. 💥

🎧 Listen to the full episode:

🔹 Spotify: https://earlypod.com/spotify

🔹 Apple Podcasts: https://earlypod.com/apple

🚀 New episodes drop every Tuesday. Let’s build this together.

👉 Like, subscribe, and drop a comment — I want to hear from you!!

📩 Thoughts or guest ideas? Email me: max@earlypod.com

📱 Follow for daily updates:

• 🐦 X (Twitter): https://earlypod.com/x

• ✨ TikTok: https://www.earlypod/tt

• 📸 Instagram: https://www.earlypod/ig

• 💼 LinkedIn: https://www.earlypod/li

• 📩 Newsletter: https://earlypod.com/subscribe

Before Uber was a global juggernaut, it was local, it was gritty, and it was hard.

This week we interviewed Scott Gorlick, who joined Uber in 2012. He cold-emailed Travis to get the job, and helped launch Uber Atlanta from a coworking space—until they got kicked out. Then it got worse: a gun pulled in the office, driver onboarding from his apartment, and scaling so fast they accidentally became one of Apple’s biggest iPhone buyers.

This episode is a raw look at the dirty, unglamorous work that made Uber unstoppable.

We cover:

● Cold-emailing your way into Uber

● The madness of launching a new city from scratch

● Being robbed during driver onboarding (!?)

● Managing a city with zero legal clarity

● The insane iPhone logistics that fueled Uber’s growth

● What the “Pro Team” was and how it helped Uber scale smart

● Why talent density is everything—and why most companies never get it

This is what hypergrowth actually looks like.

Connect with Scott: https://x.com/sgorlick

🔔 Subscribe for more episodes with the early builders behind iconic startups.

📸 Follow us on TikTok, Instagram, and Twitter @earlypod

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🎧 Listen to the full episode:

🔹 Spotify: https://earlypod.com/spotify

🔹 Apple Podcasts: https://earlypod.com/apple

🚀 New episodes drop every Tuesday. Let’s build this together.

👉 Like, subscribe, and drop a comment — I want to hear from you!!

📩 Thoughts or guest ideas? Email me: max@earlypod.com

📱 Follow for daily updates:

• 🐦 X (Twitter): https://earlypod.com/x

• ✨ TikTok: https://www.earlypod/tt

• 📸 Instagram: https://www.earlypod/ig

• 💼 LinkedIn: https://www.earlypod/li

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Before the tens of billions raised, the almost $50B!! valuation... the Summer Camps... the flameout....& the Hulu doc… there was one scrappy floor in SoHo, New York — and Jesse Middleton was there at a desk. Now he tells all.

As a founding team member and co-creator of WeWork Labs, Jesse helped build WeWork from a Craigslist ad to a global phenomenon. In this episode, he breaks down how it all happened — and where it all went off the rails.

We cover:

● The real story of WeWork’s earliest days

● Why WeLive felt wrong from the start

● How Adam Neumann inspired obsession (and burnout)

● What Summer Camp was actually like

● How Jesse uses those lessons now as a venture capitalist

This is one of the most honest, in-the-room breakdowns of WeWork ever recorded.

🎧 Subscribe for new episodes every Tuesday: earlypod.com

📱 Follow us on IG/TikTok: @earlypod

📬 Get The Early Drop newsletter: https://earlypod.com/subscribe

#WeWork #Startups #EarlyPodcast #Visionaries #VentureCapital

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🎧 Listen to the full episode:

🔹 Spotify: https://earlypod.com/spotify

🔹 Apple Podcasts: https://earlypod.com/apple

🚀 New episodes drop every Tuesday. Let’s build this together.

👉 Like, subscribe, and drop a comment — I want to hear from you!!

📩 Thoughts or guest ideas? Email me: max@earlypod.com

📱 Follow for daily updates:

• 🐦 X (Twitter): https://earlypod.com/x

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• 📸 Instagram: https://www.earlypod/ig

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Marshall Osborne was a college kid from Indiana who landed in San Francisco with no job, no apartment, and no promise of a role—just hustle.

Within weeks, he talked his way into an internship at Uber, eventually dropping out of school and becoming the intern who took Beyoncé to Vegas and helped turn Uber into a cultural verb.

What followed was a GREAT early employee journey that will inspire everyone who hears it.

In this episode, Marshall breaks down how he:

● Saved a major deal by publicly correcting Amex’s president mid-meeting

● Turned Uber into a pop culture juggernaut through celebrities, sports, and brand deals

● Negotiated a secret Beyoncé concert for 4,500 Uber employees… paid in equity

● Helped launch Uber’s NFL partnership and Spotify integrations before “brand collabs” were a thing

● Learned to make impossible deals happen by understanding incentives, timing, and how to “know your enemy”

He worked alongside with Travis Kalanick and Emil Michael, helped define Uber’s early brand, and played a massive role in turning a ride-hailing app into a lifestyle.

Whether you’re a founder, a dealmaker, or just love behind-the-scenes startup chaos — this episode is a masterclass.

Connect with Marshall: https://www.linkedin.com/in/marshallosborne/

🔔 Subscribe for more episodes with the early builders behind iconic startups.

📸 Follow us on TikTok, Instagram, and Twitter @earlypod

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🎧 Listen to the full episode:

🔹 Spotify: https://earlypod.com/spotify

🔹 Apple Podcasts: https://earlypod.com/apple

🚀 New episodes drop every Tuesday. Let’s build this together.

👉 Like, subscribe, and drop a comment — I want to hear from you!!

📩 Thoughts or guest ideas? Email me: max@earlypod.com

📱 Follow for daily updates:

• 🐦 X (Twitter): https://earlypod.com/x

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Frederique helped build the tools that made Uber scale, before there were dashboards, systems, or even GPS driving directions in the app.

In this episode of The Early Podcast, Max sits down with Frederique Dame, an early product leader at Uber and now a General Partner at GV (Google Ventures). They dive deep into the early chaos, the culture that made Uber magic, and how Frederique architected the driver onboarding experience that powered the company’s global growth.

From building backend systems to managing all-hands-on-deck workations, Frederique shares what it really took to scale—and how great culture isn’t just built, it’s lived.

🎙 Topics include:

• Why Uber didn’t prioritize GPS early on
• How they built driver tools from scratch
• What it was like working with Travis Kalanick
• The work-hard-play-hard culture that defined Uber’s rise
• • How she brings that same energy to founders at GV

Connect with Frederique: https://www.linkedin.com/in/frederiquedame/

🔔 Subscribe for more episodes with the early builders behind iconic startups.

📸 Follow us on TikTok, Instagram, and Twitter @earlypod

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🎧 Listen to the full episode:

🔹 Spotify: https://earlypod.com/spotify

🔹 Apple Podcasts: https://earlypod.com/apple

🚀 New episodes drop every Tuesday. Let’s build this together.

👉 Like, subscribe, and drop a comment — I want to hear from you!!

📩 Thoughts or guest ideas? Email me: max@earlypod.com

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• 🐦 X (Twitter): https://earlypod.com/x

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What do you do when you're handed a $0 marketing budget… and you're launching a credit-card-based app in a country where only 2% of people have credit cards?

Oh — and no one trusts your company?

If you're Akshay BD, you figure it out.

Follow Akshay on X: https://x.com/akshaybd

This week, I’m joined by Akshay — one of Uber India’s earliest employees — who shares the chaos of launching Uber in a cash-based, low-tech, regulation-light market. A country that couldn’t be further from the original Uber model.

From handing out iPhones to suspicious drivers… to fending off police raids, political bans, and near deportations — this is a masterclass in scrappy execution under pressure.

We talk about recruiting the “unhireables,” building policy from scratch, and what it was really like working alongside Travis Kalanick during Uber’s most explosive years.

One of the funniest, sharpest, and most insightful convos we’ve had yet. Let’s go!!

🎯 Topics Covered:

00:00 – The wild way Uber hired in new cities

02:00 – Growing up in Bangalore, debating on Orkut

04:00 – Standup comedy to Uber India

08:30 – Launching Uber in a market with 2% credit cards

11:00 – Convincing drivers Uber wasn’t a scam

14:00 – Making $0 marketing feel like magic

19:00 – The 2014 assault incident and national crisis

24:00 – Becoming “interim head of public policy” overnight

28:00 – Travis gets detained at the airport before meeting India’s Prime Minister

33:00 – Teaching startup culture at scale

41:00 – Why Uber taught you to make lemonade out of thin air

44:00 – Post-Uber lessons, crypto, and what’s next

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🎧 Listen to the full episode:

🔹 Spotify: https://earlypod.com/spotify

🔹 Apple Podcasts: https://earlypod.com/apple

🚀 New episodes drop every Tuesday. Let’s build this together.

👉 Like, subscribe, and drop a comment — I want to hear from you!!

📩 Thoughts or guest ideas? Email me: max@earlypod.com

📱 Follow for daily updates:

• 🐦 X (Twitter): https://earlypod.com/x

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What would you do if someone offered you $1.8 million to sabotage Uber?

That’s exactly what happened to Eric Wimer, one of the early operators at Uber, who helped launch and scale the Philly and Vegas markets from scratch. In this episode of The Early Pod, Eric reveals the untold story of the bribe, the chaos of the early days, and the wild tactics Uber used to win — including creating a fake limo company to outsmart corrupt regulators.

This is one of the most entertaining behind-the-scenes startup stories you’ll hear — filled with lessons on grit, leadership, managing through uncertainty, and betting on yourself.

We cover:

• Why Philly’s taxi industry offered Eric $1.8M to take Uber down

• How Uber secretly launched a shell company to flood supply

• What it felt like operating in legal gray zones at age 23

• The power of Travis Kalanick’s leadership and internal culture

• How Eric turned around the Vegas market and brokered deals with top hotel groups

• His biggest management mistakes — and how he got better

• What he’s building now with Sway, a returns and delivery startup

• Why trusting your gut is one of the most underrated founder skills

If you love war stories from the frontlines of iconic startups — this one’s for you.

🎙 Hosted by Max Crowley, early Uber employee and founder of The Early Pod.

Timestamps:

00:00 – The $1.8M bribe offer

04:00 – Cold emailing Ryan Graves to land the Uber job

08:00 – Launching Uber Philly with zero cars

12:00 – Creating a fake limo company (Gaggen LLC)

16:00 – Outmaneuvering the Philadelphia Parking Authority

20:00 – Workation, Travis speeches, and the Uber culture

28:00 – Transitioning from IC to manager

34:00 – Fixing Vegas: From Uber Chopper to hotel deals

41:00 – Being true to your gut & reversing big life decisions

48:00 – Life coaching, inner work, and building Sway

52:00 – Advice for aspiring founders

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🎧 Listen to the full episode:

🔹 Spotify: https://earlypod.com/spotify

🔹 Apple Podcasts: https://earlypod.com/apple

🚀 New episodes drop every Tuesday. Let’s build this together.

👉 Like, subscribe, and drop a comment — I want to hear from you!!

📩 Thoughts or guest ideas? Email me: max@earlypod.com

📱 Follow for daily updates:

• 🐦 X (Twitter): https://earlypod.com/x

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