Why Uber’s #25 Employee Is Starting From Scratch Again

In Season 4, Episode 2 of Turning Pro, Ben Sharf sits down with Max Crowley - former Chief of Staff at GoPuff, founder of Bandit (acquired), and one of Uber’s first 25 employees. Today, Max is turning the mic on, launching The Early Podcast to spotlight the overlooked builders who help scale companies from the inside out.

Max breaks down how Uber went from SMS-based car hailing to global dominance, why working at the right startup can be more valuable than starting one, and how to use transitions—between jobs, ideas, and identities—as a launchpad. Whether you’re figuring out your next thing or doubling down on the one you’re in, Max brings hard-won lessons on momentum, structure, team-building, and staying humble even when the stakes are massive.

Listen to Season 4, Episode 2 on Apple, Spotify, or YouTube.

10 Takeaways from Max Crowley’s Episode

1.  Startups Are Made in the Messy Middle: Uber didn’t begin with an app. It started with a text message and a promise. The lesson? Nail the simplest version of your idea before overbuilding.
   

2. Reinvention Is a Skill: After scaling Uber and GoPuff, Max intentionally slowed down to reset. Taking space between jobs can be powerful - if you fill it with structure, learning, and micro-experiments.
   

3. Hand-to-Hand Combat Still Works: Max grew his podcast one subscriber at a time - literally walking up to people and asking them to pull out Spotify. Scrappy never goes out of style.
   

4. Optimize for Impact, Not Ego: Whether it's advising founders or recording episodes, Max chases projects where his effort leads to tangible outcomes. That's how he knows he's on the right path.
   

5. Don’t Quit When It’s Not Viral: Podcasting (and most creative work) is a long game. Max’s focus? Not going viral, just staying consistent. That’s the real unlock for growth.
   

6. Hustle Like It’s 2011: To get into Uber, Max got turned down multiple times. His mom told him to turn the screws. He sent a more aggressive email and got hired. Persistence > polish.
   

7. Hire for Grit, Not Resumes: At GoPuff, Max preferred hiring "adult interns" - scrappy people in their late 20s and 30s who were willing to prove themselves with action, not credentials.
   

8. There’s No Training Manual for Startups: Early employees are thrown into the deep end. The ones who thrive don’t wait for permission - they solve real problems and learn by doing.
   

9. Being an Employee Can Be Elite: You don’t have to be a founder to win big. Max’s podcast spotlights early employees who build generational wealth and meaningful impact without being the face of the company.
   

10. Relationships Compound: Years after leaving Uber, Max found himself back in the seat at GoPuff with many of the same people. His advice? Curate your network. These are the people you'll build with again.

Max’s episode is a reminder that success doesn’t always come from being in charge. Sometimes it comes from showing up early, doing the hard stuff, and trusting that your path will make sense in hindsight.

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