From the Bottom of a Bottle 🍷 with Phil. Rare whiskey. Uber war stories. Immigrant hustle.

In this episode of The Early Podcast, I sit down with Phil Mikhaylov, early Uber operator and founder of Unicorn, the fastest-growing marketplace for rare spirits and wine.

We talk about growing up as a Soviet-era immigrant, grinding through Uber’s wild early days (from slogging Lyft drivers to launching Uber in India), and how a lifelong obsession with bottles, time, and craft turned into a $150M+ business.

This is a conversation about hustle, execution, ownership, and building something that lasts — one story at a time.

🎧 Birth-year bottles

🚗 Uber chaos

🦄 Building Unicorn, the biggest wine and spirits biz anywhere: https://www.unicornauctions.com/

🔥 Turning “no” into “YES”

#TheEarlyPodcast

#StartupStories

#FounderJourney

#Entrepreneurship

#EarlyStage

#EarlyPod

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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 raw stories from the trench years when your startup could still fail tomorrow.

✅ Subscribe for more untold startup stories every week

✅ Like, comment & share if you know someone who’d love this

✅ 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://earlypod.com/tt

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

• 💼 LinkedIn: https://earlypod.com/li

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

Episode 33! An interview with Bradley Tusk, the EARLY Uber political strategist and FIXER.

Bradley wanted to get into politics from a young age and eventually became Deputy Governor of Illinois at just 29. Travis called him when Uber was fighting for its life in city after city. Before Uber, Bradley ran major political campaigns across the country and advised Mayor Bloomberg. After helping Uber legalize ridesharing, he went on to work on fantasy sports and other heavily regulated industries.

In this episode, we get into how power actually works: the political incentives that drive every decision, why good people don’t run for office, the back-room battles behind keeping Uber alive, and why mobile voting could change everything. Bradley also breaks down VC delusion, autonomous vehicles, AI hype, and the future of American politics.

If you’re into startups, government, tech history, or the chaos behind the scenes… this one’s GREAT.

#BradleyTusk #Uber #UberStories #Startups #TechHistory #Politics #Regulation #TechPolicy #TechPodcast #FounderEnergy #TheEarlyPodcast #EarlyPod #MaxCrowley

--

🎙️ 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 raw stories from the trench years when your startup could still fail tomorrow.

✅ Subscribe for more untold startup stories every week

✅ Like, comment & share if you know someone who’d love this

✅ 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://earlypod.com/tt

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

• 💼 LinkedIn: https://earlypod.com/li

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

**👩‍💻 This episode is brought to you by CURA – Virtual Assistants trained for real estate. From inbox management to marketing and social media, or whatever daily tasks you need, CURA helps agents free up time and grow their business. Learn more at workwithcura.com 👩‍💻**

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What happens when two brokers decide to split everything 50/50 and go ALL IN together? Scott Hustis and Mark Jovanovic were among the early Compass brokers who helped shape the company from its scrappy Urban Compass days into one of the largest brokerages in the U.S.

In this episode, we cover:

✅ How Scott & Mark built a true 20-year partnership by sharing everything equally

✅ The grit of grinding through the 2008 financial crisis in New York real estate

✅ Why they made the leap to join Compass early, and what those chaotic first months looked like

✅ Behind the scenes of Compass’ disruption strategy, growth, and culture

✅ Lessons on partnership, risk-taking, and betting on yourself

If you’re interested in entrepreneurship, real estate, or what it really takes to build something new, this one’s for you.

📍 Hosted by Max Crowley, Uber’s 25th employee.

📌 Subscribe for more conversations with the early builders behind iconic companies.

#Uber #Startups #Tech #FounderEnergy #CareerAdvice #TheEarlyPodcast #EarlyPod #realestate #realtors #compassrealestate #brokers

--

🎙️ 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 raw stories from the trench years when your startup could still fail tomorrow.

✅ Subscribe for more untold startup stories every week

✅ Like, comment & share if you know someone who’d love this

✅ 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

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 turned every product into a search machine (and why that printed cash)

• Why downturns (dot-com bust, Great Recession) created Google and Uber

• The folklore behind Kevin@google.com and opening Google Chicago

• The IPO moment: from “J-O-B” to choosing meaningful work

• A surreal 9/11 story from inside Google’s business team in Manhattan

• Building 1871 and what it takes to ignite a city’s startup ecosystem

• Real talk on careers: relationships, respect, and timing over pedigree

If you love unfiltered origin stories, hard lessons, and the decisions that change a life — this one’s for you.

👉 If this hit, like, subscribe, and drop a comment with your favorite moment.

#Google #Startups #TechHistory #EarlyEmployees #ChicagoTech #CareerAdvice #1871 #TheEarlyPodcast #EarlyPod

—

🎙️ 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 raw stories from the trench years when your startup could still fail tomorrow.

✅ Subscribe for more untold startup stories every week

✅ Like, comment & share if you know someone who’d love this

✅ 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

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 into Uber

• The wild days of Uber New York, customer credits, and “Uber Chopper”

• Breaking into product management without a technical background

• What it takes to build a startup after Uber — and almost running out of payroll

• Why persistence beats pedigree, and why proximity matters

If you like stories about scrappy beginnings, growth, and reinvention — this one’s for you.

👉 Don’t forget to like, subscribe, and drop a comment if you enjoyed the episode.

#Uber #Startups #Tech #productmanagement #FounderEnergy #CareerAdvice #TheEarlyPodcast #EarlyPod

--

🎙️ 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 raw stories from the trench years when your startup could still fail tomorrow.

✅ Subscribe for more untold startup stories every week

✅ Like, comment & share if you know someone who’d love this

✅ 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

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 getting in, how his farm upbringing prepared him for startup chaos, and what it really takes to be the “Work Horse” in an early-stage company.

🔑 Topics Covered:

• From Kentucky farms to Uber’s frontlines

• The chaos and speed of launching Uber Taxi

• Allen’s advice: focus on the exit, not just the entry

• Why startups demand more than just ideas — they demand stamina

If you enjoyed this clip, check out the full conversation with Allen Penn on The Early Podcast.

#Uber #Startups #ChicagoTech #Taxi #FounderEnergy #CareerAdvice #TheEarlyPodcast #EarlyPod

--

🎙️ 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 raw stories from the trench years when your startup could still fail tomorrow.

✅ Subscribe for more untold startup stories every week

✅ Like, comment & share if you know someone who’d love this

✅ 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

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

-Breaking into Visa and learning finance from the ground up

-Joining Uber after its Series A and helping scale the company into a global powerhouse

This is the story of grit, timing, and turning setbacks into billion-dollar opportunities.

🎧 Listen to the full conversation with Jesse Lucas here and on more channels below.

If you enjoy this episode, make sure to like, subscribe, and share The Early Podcast for more stories from the builders behind iconic startups.

#Uber #startups #entrepreneurship #TheEarlyPodcast #earlypod

--

🎙️ 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!!

📩 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

🎯 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 whatever it took to keep the system running.

Alyssa also opens up about:

✅ Facing stage 4 cancer as a teenager and the resilience it built

✅ The grind of scaling UberX in Chicago — Google Sheets, late-night driver calls, and all

✅ Why “doing things that don’t scale” is the only way to find product-market fit

✅ Her journey from Uber operator to CEO of Fellow, a peer-to-peer support platform

Whether you’re an early employee, founder, or just love startup stories, this episode is packed with lessons on grit, resilience, and building something that matters.

🎧 Full episode here → Links below

📺 More clips + episodes → youtube.com/@UCzvF8vzXF4QaTkCWFRtV20g

#Uber #startups #entrepreneurship #TheEarlyPodcast #earlypod

--

🎙️ 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!!

📩 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

🎯 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

--The $1 billion year Uber spent competing in China

--How Travis Kalanick’s aggressive playbook scaled Uber globally

Perfect for a commute, workout, or quick travel break — the wildest stories from Sam’s time at Uber, packed into 25 minutes.

#Uber #Startups #MiniEpisode #TechStories #facebook

⸻

🎙️ 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!!

📩 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

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 startups in general.

We talk about:

🚗 The truth behind driver classification and outdated labor laws

🔥 What it was really like working with Travis

📜 How to be a legal enabler, not a blocker, in a startup

💼 Lessons from Uber, Yahoo, and now DoorDash

🧠 Why confidence, timing, and trust matter more than perfection

Abby shares unfiltered stories from the trenches—chicken in the dishwasher, dogs pooping in conference rooms, and why emotional trauma can bond a team.

Whether you’re a founder, operator, or lawyer thinking about going in-house, this one is packed with insight, laughter, and some hard-earned wisdom.

🎧 Subscribe for more interviews with early employees from iconic companies:

https://earlypod.com

#Uber #DoorDash #GigEconomy #Startups #EmploymentLaw #TheEarlyPodcast #earlypod

⸻

🎙️ 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!!

📩 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

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

🚀 The early days of Accenture and taking the company public

📉 Mistakes, sweaty-hand moments, and the leadership lessons that came from them

👥 Why “treat others how they want to be treated” is the key to managing people

🌍 Going global: offshoring, outsourcing, and building culture across borders

❤️ How she built a team that produced over 40 CHROs at major companies

This is a masterclass in building organizations and taking care of the people inside them.

👇 Watch the full episode and hit subscribe for more interviews with the builders behind the world’s most iconic companies.

#Accenture #HRLeadership #Startups #EarlyEmployees #WomenInBusiness #TheEarlyPodcast #EarlyPod

⸻

🎙️ 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!!

📩 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

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 Taylor Canfield.

We cover:

🚀 Why SailGP is F1 on water

🌎 How Ryan helped build a global race team

📊 30,000 data points per second per boat

🧠 Tactical mastery, physical endurance & wild stories from the water

💥 And yes — race day is still less intense than Travis Kalanick

Ryan and Taylor take us from rookie sailing lessons to racing at 60+ mph, with helicopters, AR graphics, and Olympic-level strategy — all while building a business around it.

Subscribe for more stories from the earliest builders behind iconic startups.

#startups #sailing #SailGP #Uber #sportsbusiness #earlyemployees #F1

⸻

00:00 From Uber to SailGP – Ryan’s Journey

01:12 Redefining Success After a Unicorn

02:31 First Sailing Lesson → Near Disaster

04:55 Obsession Turns Into Team Ownership

05:35 What Is SailGP? F1 on Water Explained

07:05 60 MPH Boats, Foils, and Flight

09:21 30,000 Data Points Per Second

11:14 Filming Races with Helicopters & AR

13:20 Turning the Team into a Real Business

14:11 Race Day vs. Travis Kalanick

15:40 Taylor Canfield’s Origin Story

18:45 World Championships & the America’s Cup Dream

22:00 Driving an F50 for the First Time

24:42 Race Day: Prep, Strategy & Execution

27:05 How the Races Actually Work

29:37 Wind, Intuition, and Real-Time Decisions

31:01 Safety Protocols & Crazy Stories

34:27 F1 Meets Ocean: Why This Sport Wins

36:00 Athleticism + Trigonometry at 60mph

⸻

🎙️ 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!!

📩 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

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 “Founder Radar”: a gut instinct for spotting generational talent before the spreadsheets, pitch decks, or models exist.

More to come with Shervin in the coming months. This is a PART 1!

We get into:

• 🚕 The full-circle story of his dad driving a cab and Shervin investing in Uber

• 🧭 How he learned to “detect the signal” and back founders at the idea stage

• ✈️ The story behind chasing Travis to Dublin to close the Uber deal

• 🌍 Building Uber’s global city launch playbook & regulatory war chest

•⚡ How he got Elon Musk and Travis in a Tesla at SXSW — and why it mattered

•🎓 Paying it forward: From founding companies to investing in the next generation

👉 Listen, subscribe, and share with anyone who loves raw stories from the people who really built iconic companies.

⸻

⏱️ Chapters

0:00 Intro — Founder Radar

2:10 Escaping Iran & the Cab Story

10:00 Starting WebOS, First Wins

18:00 Early-Stage VC vs Spreadsheet VC

28:00 Meeting Travis Kalanick

36:00 The Dublin Term Sheet

46:00 Tesla, Elon & Travis SXSW

56:00 Lessons in Gut Instinct Investing

⸻

🎙️ 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.

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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.

⸻

⏱️ 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

⸻

🎙️ 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!!

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

📱 Follow for daily updates:

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

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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

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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

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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

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

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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

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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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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

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