Everything is Going to be Hard - Episode 2 with Allen Penn

Big things start small. The Early Podcast. Stories and insights from early employees and innovators who’ve shaped the future.

In this episode, I sit down with Allen Penn, one of Uber’s very first hires. We launched Uber Chicago together in 2011—but that was just the beginning. Allen went on to spearhead Uber’s explosive growth across Asia, including China, India, Japan, and Southeast Asia, leading teams through some of the most intense battles in tech history.

What We Talk About:

• Growing up on a tobacco farm in Kentucky and how that shaped his work ethic

• Joining Uber when there were only a handful of employees—and zero playbook

• Launching Chicago, figuring out supply and demand with nothing but a spreadsheet

• Why “15 out of 15 cars on the road” was still considered a failure

• The global expansion: launching Asia, surviving China, and trying not to go to jail in Korea

• The real story behind Uber’s billion-dollar battles with Didi and Grab

• Lessons on leadership, risk, reinvention—and why he’s now running a sauna & cold plunge business in Nashville

🔥 Allen’s Best Quotes:

💡 “If you want to work on interesting stuff, you have to make it happen.”

💡 “Everything is either hard right now, or it’s about to be hard.”

💡 “You need to get lucky, but luck favors the ones who execute consistently.”

Whether you’re a founder, operator, or just love a good behind-the-scenes story, this one is packed with laughs, war stories, and hard-earned wisdom from one of the sharpest operators in the game.

Where to Listen:
🎧 Listen on Spotify
🍎 Listen on Apple Podcasts
📩 Newsletter & More Content
🐦 Follow on X (Twitter)
📸 Follow on Instagram
💼 Connect on LinkedIn

Thanks for listening! We’re launching new episodes (at least) every Tuesday, and I’d love your feedback on who we should interview next. Email me: max@earlypod.com

Let’s go!!!!! 🚀

#EarlyPodcast #Startups #Entrepreneurship #PodcastLaunch #FounderStories #EarlyPod