The Early Podcast

From dot-com chaos to Google’s rocket ship. Kevin Willer helped establish Google’s Midwest presence in Chicago when “search” wasn’t yet obvious and ad tech was still being pieced together. He scored Kevin@google.com, watched the 2004 IPO rewrite his life, sat with the team in NYC on 9/11, and later helped Chicago “plant a flag” with 1871, its startup hub.

In this episode, you’ll hear:

• How Google ...

Jeremy Lermitte’s story has it all: a Canadian farm kid who lost $25K trying to trade stocks, hustled his way into Uber New York as employee #4, and eventually became a product manager driving some of Uber’s biggest global features. He later co-founded Red Circle, a rapidly growing podcast advertising platform.

In this episode, we cover:

• How persistence (and a few lucky introductions) got him int...

Allen Penn grew up on a Kentucky horse farm, learning grit and hard work from a young age. He went from private equity to becoming one of Uber’s earliest operators, spearheading the launch of Uber Taxi in Chicago and helping shape the playbook that fueled Uber’s explosive growth, including across Asia.

In this Mini (Best Of) episode, Allen shares why every entrepreneur should think more about getting out than...

What do Olive Garden breadsticks, Napster, and Uber all have in common? 👉 Jesse Lucas.

In this Mini (Best Of) episode, Jesse shares his unlikely journey:

-Growing up working-class on Cape Cod

-Interning at Napster with Sean Fanning (and meeting Travis Kalanick years before Uber)

-Waiting tables at Olive Garden while his classmates worked at Goldman Sachs

-Breaki...

🎯 Mini (Best Of) Episode that's under 30 minutes. In time for summer travel... we're curating some of our most popular episodes, now condensed into a fast, no-filler cut.

What does it really take to build a startup from scratch? In this condensed “Best Of” episode, Alyssa Pollack shares raw stories from her early days at Uber — onboarding drivers one by one, running seven-day-a-week ops, and doing wha...

🎯 Mini (Best Of) Episode that's under 30 minutes. In time for summer travel... we're curating some of our most popular episodes, now condensed into a fast, no-filler cut.

Sam Gellman helped launch Uber in London, Amsterdam, Singapore, Shanghai, and Hong Kong.

In this Mini Episode, we cover:

--Why he turned down an interview to be Facebook’s first non-founder hire

What’s it like to be the first employment lawyer at one of the most legally complex startups in tech history?

In this episode, I sit down with Abby Horrigan, who joined Uber in its wild early days to navigate gig worker classification, mounting lawsuits, and a company moving faster than the law itself. She’s now Deputy General Counsel at DoorDash — so there’s no better expert on the legality behind the sharing economy and startu...

What does it take to scale one of the world’s largest professional services firms — and still lead with heart?

In this episode, we sit down with Jill Smart, former CHRO and one of the original leaders who helped transform Arthur Andersen into Accenture, now a 700,000+ employee global powerhouse.

We dive into:

✨ Growing up blue-collar — and building a work ethic that never left

What do you do after building one of the most iconic companies of our generation?

If you’re Ryan McKillen, one of Uber's EARLY employees, you buy the U.S. SailGP Team and dive headfirst into the high-tech, high-stakes world of professional sailboat racing.

In this episode of The Early Podcast, we go behind the scenes of US SailGP — the Formula 1 of the ocean — with Ryan and team driver Tayl...

In this episode of The Early Podcast, I sit down with legendary early-stage investor Shervin Pishevar — the man who bet on Uber in October 2011, when it had only 30 people, and helped launch it around the world.

From escaping Iran as a child to watching his Father struggle while driving cabs in DC — and then backing Travis Kalanick, Elon Musk, and more — Shervin shares how he developed what he calls his “Found...

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 starti...

🚗 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...

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...

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 — ...

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 wh...

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 onboa...

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 lau...

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 corru...

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 resilienc...