The Early Podcast

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: [email protected]

📱 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

My most important guest on The Early Podcast: MY MOM :).

In honor of Mother's Day... and happy Mother's Day to all the moms out there!!

Meet Jay Crowley — she left home at 17, got spotted by CBS Records without a college degree, lost nearly everything on a Quiznos franchise, then reinvented herself in her 40s and built a thriving real estate business from scratch.

This episode is about resilience, reinvention, and refusing to quit—even when the odds are stacked against you.

We cover:

• What it was like growing up with an alcoholic & abusive father in the early Chicago suburbs

• Breaking into the music industry and winning sales rep of the year

• Betting the house (literally) on Quiznos — and losing

• Reinventing herself in real estate after getting fired from her first team

• The advice she gave me that helped me land my job at Uber

• And what she wants her legacy to be

It’s personal, emotional, and proof that failure isn’t fatal — and reinvention is ALWAYS possible.

If you’re into underdog stories, late-stage comebacks, or just want to hear where I got my drive and hustle... this one’s for you.

🔔 Subscribe for more real stories from early builders, unsung operators, and people who bet on themselves

🎧 Listen on Spotify, Apple, or YouTube

📸 Follow us on TikTok + IG → [@earlypod]

Follow Jay: https://www.instagram.com/jaycrowleysells/

#MothersDay #Podcast #RealEstate #StartupStories #Reinvention #WomenInSales #TheEarlyPodcast #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: [email protected]

📱 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

Early Pod's first non-Uber interview — and it’s a good one! Introducing TWITTER's 30th employee: Ryan Sarver.

Ryan joined Twitter as employee #30 and helped scale it from a chaotic startup to a global platform. He led the API and developer platform, lived through the explosive growth, and saw the company up close as it missed major moments like Instagram, DMs, and video.

We get into:

• What it was like working under Jack Dorsey and Ev Williams

• The real story behind losing Instagram to Zuck

• A voicemail from Steve Jobs that changed everything

• Twitter’s early culture, chaos, and the lessons Ryan took into VC

If you're into startup history, product strategy, or what really happens behind the scenes at iconic tech companies — this one's for you.

🔔 Subscribe for more deep dives with early builders

🎧 Listen wherever you get your podcasts

📸 Follow us on TikTok, Instagram → @earlypod

Follow Ryan: https://x.com/rsarver

#startups #twitter #techhistory #api #product #zuck #stevejobs #earlyemployees #theearlypodcast #x #earlypod #jackdorsey

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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: [email protected]

📱 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

Welcome to Episode 11! With this one… we’re diving into one of the most controversial features in Uber history: SURGE PRICING.

Meet Kevin Novak — a physicist turned data scientist who was asked to solve the impossible: how do you get enough drivers on the road… exactly when you need them?

After joining in 2011 as Uber employee # 21... and armed with no team and no time, Kevin built what became known as surge pricing — and then watched it nearly blow up the company on its very first night.

From there, he helped shape the role of data science at Uber and across the tech world. In this episode, we cover:

• How a nuclear physics grad student ended up in an Uber interview… in a wrinkled suit
• The wild origin story of surge pricing (and why it almost failed)
• What it was like working directly for Travis Kalanick in Uber’s early days
• Why data scientists have become essential at tech companies
• The interview tactics, team culture, and speed obsession that defined Uber 1.0
• Kevin’s transition from operator to VC — and what he looks for now at Rackhouse

This one’s about inventing under pressure, moving fast, and building something from nothing. If you’ve ever wondered how startup culture really gets built — this is a masterclass.

Episode 11 is live. Let’s go. 🚀

👇 Kevin on LinkedIn: https://www.linkedin.com/in/novakkm/

#EarlyPodcast #Uber #SurgePricing #StartupStories #DataScience #TravisKalanick #SiliconValley #ProductDriven #StartupGrit #TechFounders #Hypergrowth #PhysicsToTech #UberDataTeam #FoundersJourney #RackhouseVentures

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🎧 Listen to the full episode:

🔹 Spotify: https://open.spotify.com/show/13dcsmz27cQ4LZUHxJY1n4

🔹 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: [email protected]

📱 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

With this episode... we’re going deep into the trenches — a little dog pee, thousands of drivers protesting in Asia, and a $30-a-night Airbnb in Detroit… plus all the shenanigans that came with it.

Chan Park joined Uber in 2012 with a limited playbook for expansion and one goal: launch cities as FAST AS POSSIBLE. On day one, he was told, “Why aren’t you in Sacramento?”—and things only got wilder from there.

He launched Uber in Detroit from the sketchiest Airbnb on Eight Mile, then got sent across the world to open up Asia. From navigating protests in Jakarta to pitching Travis on a $1.5B car fleet in Singapore, Chan shares the insane scrappiness it took to help make Uber global.

In this episode, we cover:

• The details of being born in Korea and immigrating to the U.S. at a young age

• What it was like to launch Uber from a $30 Airbnb in Detroit

• Why 10,000 people protested Uber... when they had just 12 cars on the road

• The actual Uber interview process (“They asked what I do on weekends…”)

• Travis’s response to a billion-dollar car fleet idea

• What it takes to build global scale in the middle of chaos

This one’s packed with raw stories, working your ass off, and what it actually took to scale Uber worldwide. If you've ever wondered what extreme ownership really looks like — this is it.

Episode 10 is live. Let’s go. 🚀

👇 Connect with Chan

📱 Chan on LinkedIn: https://www.linkedin.com/in/chanwoongpark/

#EarlyPodcast #Uber #StartupStories #Founders #TechFounders #SiliconValley #ScaleUp #UberAsia #ProductDriven #FoundersJourney #Podcast #StartupGrit #hypergrowth #korea

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🎧 Listen to the full episode:

🔹 Spotify: https://open.spotify.com/show/13dcsmz27cQ4LZUHxJY1n4

🔹 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: [email protected]

📱 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

For this episode, we’re going EARLY EARLY… Uber employee #3!

Ryan McKillen helped build Uber from the ground up — literally. He walked in on day one to find a stack of pristine coding books… and one beat-up Spanish dictionary.

“Why?”

“All the code’s in Spanish. Welcome to Uber.”

Ryan went from CPA to self-taught engineer, joined Uber pre-hypergrowth, helped launch Paris in 5 weeks, and was there for the infamous cease & desist moment that put the company on the map. He shares what it was like building through chaos, working side-by-side with Travis, and how the early Uber culture shaped his career — and life.

In this episode, we cover:

• The very first days of Uber — and why all the code was in Spanish

• What Travis Kalanick did after the cease & desist

• How Ryan helped launch Uber Paris in 5 weeks

• What made early Uber’s engineering culture so special

• Ryan’s post-Uber chapter: sailing, startups, and owning the U.S. SailGP team

This one’s packed with real stories, startup grit, and some hilarious early tech chaos. If you’ve ever wondered what it’s really like to build from day one — listen up.

Episode 9 is live. Let’s go. 🚀

👇 Connect with Ryan

📱 Ryan on LinkedIn:  / ryan-mckillen  

🎧 Listen to the full episode here:

🔹 Spotify: https://shorturl.at/xyzRY

🔹 Apple Podcasts: https://shorturl.at/abc12

Don’t forget to like, comment, and subscribe — new episodes every Tuesday!

⸻

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

👉 Like, Subscribe, and Drop a Comment — I want to hear from you!

📩 Email me at [email protected] with your thoughts or guest recommendations.

📱 Follow along for daily updates on social media platforms.

🐦 Follow on X (Twitter): https://x.com/maxjcrowley

✨ Follow on TikTok:  / earlypod  

📸 Follow on Instagram:  / earlypod  

💼 Connect on LinkedIn:  / maxjc  

📩 Newsletter & More Content: https://www.earlyemployee.com/subscribe

#EarlyPodcast #Uber #StartupStories #Founders #TechFounders #SiliconValley #EngineeringLeadership #StartupCulture #ScaleUp #ProductDriven #FoundersJourney #Podcast

Uber Eats would NOT be the business it is today without Alyssa Pollack.

Diagnosed with stage 4 cancer as a teenager, Alyssa’s mom told her: “Today we cry. Tomorrow, we fight.” That mentality shaped everything — from surviving the unthinkable to scaling Uber's driver operations, helping launch Uber Eats, and now leading her own startup as CEO of Fellow.

In this episode, we dive into:

• Alyssa’s early days at Uber (yes, she was literally reprogramming driver phones in bars 🍻)

• The wild evolution from black cars to UberX to Uber Eats

• What made Uber’s culture so unique — and what companies get wrong about scaling

• The founding story behind Fello, her current company redefining peer support in healthcare

• What it's like being a founder and a mom of two — and how she makes it all work

This one is packed with real stories, hard-won insights, and startup wisdom from someone who’s truly been in the trenches.

Episode 8 is here. Let’s go. 🚀

Subscribe to catch new episodes every week — and please like, comment, and share if this one hits.

👇 Connect with Alyssa & Fello

🌐 https://www.myfello.app/

📱 Alyssa on LinkedIn: https://www.linkedin.com/in/alyssa-pollack/

🎧 Listen to the full episode here:

🔹 Spotify: https://shorturl.at/e6FUf

🔹 Apple Podcasts: https://shorturl.at/Crg2V

Don’t forget to like, comment, and subscribe—new episodes every Tuesday!

⸻

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

👉 Like, Subscribe, and Drop a Comment—I want to hear from you!

📩 Email me at [email protected] with your thoughts or guest recommendations.

📱 Follow along for daily updates on social media platforms.

🐦 Follow on X (Twitter): https://x.com/maxjcrowley

📸 Follow on Instagram: https://www.instagram.com/earlypod

💼 Connect on LinkedIn: https://www.linkedin.com/in/maxjc/

📩 Newsletter & More Content: https://www.earlyemployee.com/subscribe

#EarlyPodcast #Startups #Entrepreneurship #Uber #Founders #TechStartups #StartupStories #Podcast #EarlyPod

How Rachel Holt Helped Fight for Ridesharing in DC and beyond | Early Podcast Ep. 7

Recorded in person, in New York City!

In this episode of Early, Max Crowley sits down with Rachel Holt — one of the earliest and most impactful operators at Uber and one of the company's first General Managers. Rachel shares never-before-heard stories from the company’s early days, including regulatory showdowns in D.C., the launch playbook, hiring her first team, and what it was like working directly with Travis Kalanick during Uber’s most high-stakes moments.

👀 What you’ll hear:

• The viral tweet that triggered a taxi war in Washington D.C.

• The 83-year-old cab commissioner who ordered an Uber… and had it impounded on the spot

• Rachel’s journey from Stanford MBA to General Manager of the U.S. and Canada

• How Uber scaled with humans first—and product second

• Lessons from Travis and Dara on leadership, pressure, and building generational companies

• Why Rachel left Uber and co-founded Construct Capital to back the next wave of real-world tech founders

If you’ve ever wondered what it really looked like inside Uber during hyper-growth, this is the episode for you.

🎧 Listen to the full episode here:

🔹 Spotify: https://shorturl.at/e6FUf

🔹 Apple Podcasts: https://shorturl.at/Crg2V

Don’t forget to like, comment, and subscribe—new episodes every Tuesday!

⸻

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

👉 Like, Subscribe, and Drop a Comment—I want to hear from you!

📩 Email me at [email protected] with your thoughts or guest recommendations.

📱 Follow along for daily updates on social media platforms.

🐦 Follow on X (Twitter): https://x.com/maxjcrowley

📸 Follow on Instagram: https://www.instagram.com/earlypod

💼 Connect on LinkedIn: https://www.linkedin.com/in/maxjc/

📩 Newsletter & More Content: https://www.earlyemployee.com/subscribe

#EarlyPodcast #Startups #Entrepreneurship #Uber #Founders #TechStartups #StartupStories #Podcast #EarlyPod

💥 It doesn’t get grittier than Jesse Lucas. From hustling his way into Napster, waiting tables at Olive Garden to stay afloat, and nearly getting fired at Uber before he even had the job... he ultimately helped scale one of the most iconic startups ever. Jesse’s story is one of resilience, persistence, and sheer determination.

In this episode of The Early Podcast, Jesse sits down with Max Crowley to talk about:

🔥 The scrappy hustle that got him into Napster and later into Uber

🔥 Getting brutally rejected by Travis Kalanick—and how he earned his job back

🔥 The chaotic early days of Uber and how they built its financial foundation

🔥 Near misses, setbacks, and what kept him in the game

🔥 Hard lessons from hypergrowth startups and the long road to success

Jesse’s journey is a masterclass in perseverance. If you’re grinding through challenges, navigating career uncertainty, or trying to break into startups, this episode is for you.

🎧 Listen to the full episode here:

🔹 Spotify: https://shorturl.at/e6FUf

🔹 Apple Podcasts: https://shorturl.at/Crg2V

Don’t forget to like, comment, and subscribe—new episodes every Tuesday!

⸻

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

👉 Like, Subscribe, and Drop a Comment—I want to hear from you!

📩 Email me at [email protected] with your thoughts or guest recommendations.

📱 Follow along for daily updates on social media platforms.

🐦 Follow on X (Twitter): https://x.com/maxjcrowley

📸 Follow on Instagram: https://www.instagram.com/earlypod

💼 Connect on LinkedIn: https://www.linkedin.com/in/maxjc/

📩 Newsletter & More Content: https://www.earlyemployee.com/subscribe

#EarlyPodcast #Startups #Entrepreneurship #Uber #Founders #TechStartups #StartupStories #Podcast #EarlyPod

New York City is notoriously challenging for upstarts when battling with incumbents and even City Hall. It wasn't an easy journey, but in part thanks to Josh Mohrer, you can now use Uber throughout New York. As one of Uber's early employees, Josh transformed Uber from just 50 cars into a transportation giant, overcoming regulatory hurdles, intense media scrutiny, and political battles.

🚀 From Early Employee to Winning the New York Market

Josh shares:

🔹 How he went from selling funny shirts online to leading Uber NYC

🔹 The $1,000 bonus strategy that skyrocketed Uber’s growth

🔹 The truth about Uber’s battles with Mayor de Blasio and NYC regulators

🔹 Navigating intense media scrutiny—what really happened behind the headlines

🔹 How Travis Kalanick empowered his team and reshaped urban transportation

💡 Key Takeaways:

✅ Play by the rules—but outperform everyone else

✅ Turn criticism into fuel—media pressure can sharpen your focus

✅ Founder vision matters—how Travis’s relentless execution made Uber unstoppable

🎧 Listen to the full episode here:

🔹 Spotify: https://shorturl.at/e6FUf

🔹 Apple Podcasts: https://shorturl.at/Crg2V

Don’t forget to like, comment, and subscribe—new episodes every Tuesday!

⸻

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

👉 Like, Subscribe, and Drop a Comment—I want to hear from you!

📩 Email me at [email protected] with your thoughts or guest recommendations.

📱 Follow along for daily updates on social media platforms.

Let’s do this! 🚀

🐦 Follow on X (Twitter): https://x.com/maxjcrowley

📸 Follow on Instagram: https://www.instagram.com/earlypod

💼 Connect on LinkedIn: https://www.linkedin.com/in/maxjc/

📩 Newsletter & More Content: https://www.earlyemployee.com/subscribe

#EarlyPodcast #Startups #Entrepreneurship #Uber #Founders #TechStartups #StartupStories #Podcast #EarlyPod