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.

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#WeWork #Startups #EarlyPodcast #Visionaries #VentureCapital

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

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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/

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

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

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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.

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🎧 Listen to the full episode:

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🔹 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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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:

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🚀 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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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:

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🚀 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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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

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🚀 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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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:

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

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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: max@earlypod.com

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