A recent quote from Uber CEO Dara Khosrowshahi on Verge’s Decoder podcast struck me. Paraphrased:

If AI agents bring Uber new customers, Uber will work with them. If those agents take customers away from the Uber app, Uber will charge them heavily.

That one idea explains a lot about how Uber sees the future and why I think Uber’s biggest challenge isn’t competition, regulation, or even autonomous cars. It’s something deeper.

Syracuse saw more than two feet of snow fall in a single day, the most in decades. Local officials warned people to stay off the roads. Plows struggled to keep up. Visibility dropped. The city slowed to a crawl.

New Year’s Eve is one of those nights every rideshare driver circles on the calendar. Big crowds. Big emotions. Big money... at least in theory.

This year, I decided to go all in. I created a plan, cleared my schedule, and committed to seeing how far I could push myself. By the morning, I had earned $613, spent 18 hours out of the house, and driven 323 miles.

But the biggest lesson of the night wasn’t about surge pricing, bonuses, or tips. The most important thing came from a single ride that never even happened, reminding me what truly matters in this work.

ESPN analyst and former NFL player Ryan Clark recently shared a story. He’s tired of being “musically profiled” in Uber rides, drivers switch to rap without asking, assuming that’s his preference.

I’m an Uber driver. And I have thoughts.

I'm not here to defend or dismiss. Instead, I want to clarify what’s probably really happening inside the car: these moments are rarely about conscious profiling, but rather about drivers making quick, imperfect guesses to create a positive experience.

At 4:00 a.m., I turned on the Uber app and immediately got what looked like a unicorn. A 20-minute, 10-mile Uber Comfort ride to the airport, paying $28. If you annualize that rate, it works out to roughly $166,000 a year. But as soon as I accepted, regret set in.

esterday, I picked up a passenger at a hotel and took them to the airport to rent a car. The ride was a short 7-mile trip, and Uber said I’d earn $9.20. Nothing unusual there.

Then, a few minutes after I dropped them off, my phone buzzed: a $9.50 tip. More than the fare itself.

It caught me off guard. Like, why was it more than my earnings, and why was it such an odd number? On rare occasions, passengers are super generous and tip $20 or more. But this was a young guy on a business trip.

So I opened the trip receipt in the Uber app, and that’s when things got interesting. The passenger had been charged $47 for that short weekday ride, and it wasn’t even during a busy rush.

I love uber driving. I love the flexible hours, absence of a boss, and freedom to choose when and where I work.

But how profitable has it been after five years behind the wheel? I want to share an extensive breakdown of my earnings, expenses, and insights I’ve gained from more than 13,000 trips.