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

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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

**👩‍💻 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

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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://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

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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://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

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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://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

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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://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

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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!!

📩 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

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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!!

📩 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