Imagine stepping into one of the hottest companies on the planet, only to find it’s also one of the most chaotic. Scandals everywhere, money hemorrhaging, regulators breathing down your neck, and key people jumping ship. That’s exactly what happened when a new leader took the helm of a ride-sharing giant back in 2017. Yet, against all odds, he turned things around and built something unstoppable. How did he do it? It wasn’t luck—it came down to a handful of smart, gutsy decisions that any business leader can learn from.
The Leadership Decisions That Changed Everything
I’ve always been fascinated by turnaround stories. There’s something inspiring about watching someone walk into a mess and slowly, deliberately, make it work. In this case, the results speak for themselves: a company that went from near-collapse to clear market leader. Let’s break down the five pivotal moves that made the difference.
Taking the Risk No One Else Wanted
Most executives would run the other way from a job like this. The company was already a household name—people used it as a verb—but the headlines were brutal. Ongoing controversies, massive financial losses, and a revolving door of leadership. Leaving a secure, successful position elsewhere to jump into that fire? That takes serious courage.
But here’s what stood out to me: the new CEO didn’t see just the problems. He saw the potential. The way the platform was already woven into daily life, changing how millions moved around cities. He later shared that a piece of family advice sealed it for him—when a company that’s become part of everyday language asks you to lead it, you don’t say no.
In my view, this is where real leadership begins. Not avoiding risk, but embracing it when the upside is big enough. Too many leaders play it safe and miss the opportunities that come disguised as crises.
When a company that’s a verb asks you to run it, just say ‘yes.’
– The CEO reflecting on his decision
Fixing the Culture from the Inside Out
Once in the door, the first priority wasn’t flashy growth or new features. It was culture. The old environment had become toxic—aggressive, win-at-all-costs, and it showed in every relationship, from drivers to regulators.
Instead of issuing top-down mandates or hiring a PR firm to paper over the issues, the CEO did something simpler and far more effective: he listened. Really listened. He spent time hearing from drivers, from employees, from city officials. Then he set a new standard that sounded almost too basic: do the right thing, full stop.
Trust isn’t built with slogans. It’s built with consistent actions. Safety improvements, product changes that actually helped users and drivers, transparency where there had been none. Over time, those small, steady choices rebuilt credibility.
I’ve seen companies try quick fixes for culture problems and fail miserably. What works is exactly this—slowing down enough to understand the real issues, then leading with integrity. It’s harder, but it lasts.
Leadership is about the heart. It’s about showing someone that you can be greater than your own self.
– The CEO on rebuilding trust
- Gave drivers genuine input instead of treating them as disposable
- Introduced clear values centered on doing the right thing
- Backed words with tangible safety and product upgrades
- Focused on earning trust through behavior, not spin
Switching to Survival Mode When Crisis Hit
Then came 2020. Overnight, almost 85% of the core ride business disappeared. If nothing changed, the company was looking at billions in annual losses. Most leaders would panic. This one shifted into what he called “wartime mode.”
Hard decisions followed quickly. Cost cutting on a massive scale, including letting go of about a quarter of the workforce. No one enjoys that—least of all a CEO who never imagined he’d have to make calls like that. But it was necessary to keep the company alive.
At the same time, he leaned hard into the delivery side of the business. Demand there exploded as people stayed home, giving restaurants a lifeline and drivers an alternative way to earn. What started as a side offering grew until it rivaled the original ride-sharing revenue.
This pivot didn’t just help the company survive the pandemic. It positioned it for explosive growth once things reopened. Sometimes the toughest choices are the ones that set you up for the biggest wins later.
I never imagined I’d come here to do a layoff that big — it was really, really hard, but it was necessary for us to reset.
– The CEO on the pandemic response
In hindsight, that willingness to act decisively in crisis is what separated survival from collapse for many companies during those years.
Getting Behind the Wheel Himself
As the world started opening up again, a new challenge emerged: getting drivers back on the platform. Wait times grew, customer frustration rose, and everyone knew the driver experience needed serious improvement.
Lots of employees used the app as passengers. But almost no one inside the company truly understood what it felt like to be on the driver side. So the CEO did something unusual—he signed up, got in his car, and started giving rides himself.
What he found wasn’t surprising in theory but eye-opening in practice. The app flowed smoothly for riders, but it was clunky and frustrating for drivers. Little pain points everywhere that added up to big reasons people stayed away.
Experiencing it firsthand gave him credibility and urgency when pushing teams to fix those issues. Suddenly, improvements weren’t abstract—they were personal. Driver-focused updates rolled out faster and more effectively.
Honestly, I love this move. How many executives actually use their own product the way their most important users do? Not enough. It’s easy to make decisions from a boardroom; it’s harder—and far more valuable—to feel the friction yourself.
If you want to build a great product, you have to put yourself in your customer’s shoes.
– The CEO after driving for the platform
Choosing Long-Term Strength Over Short-Term Praise
Coming out of the pandemic, the company finally had a path to profitability. Wall Street was watching closely. The easy choice? Lock in those profits, keep investors happy, play it safe.
Instead, leadership decided to invest heavily—hundreds of millions—into incentives to bring drivers back quickly and in large numbers. Short-term earnings took a hit. Stock analysts grumbled. But the bet was on sustainable growth rather than fleeting gains.
That same mindset showed up in other big calls: walking away from markets they couldn’t dominate, focusing on organic expansion rather than splashy acquisitions, partnering on complex tech like autonomous vehicles instead of going it alone.
The result? A leaner, more focused company built to last. Sometimes real leadership means swimming upstream when everyone else is going with the flow.
Leadership isn’t going where the current takes you. Leadership sometimes is swimming against the current.
– The CEO on tough strategic choices
Looking back, these decisions feel obvious now. But in the moment, they were anything but. They required conviction, patience, and a clear vision of what the company could become.
What strikes me most about this story is how universal the lessons are. Whether you’re running a startup, a division, or just trying to lead a team through change, these principles apply.
- Don’t shy away from calculated risks when the potential is huge
- Fix culture through listening and consistent action, not quick fixes
- In crisis, make the hard calls fast but with humanity
- Understand your users deeply—live their experience when you can
- Prioritize long-term health over short-term applause
Few companies get a second act after near-disaster. This one did, because someone was willing to lead differently. And today, it’s stronger than ever—proof that the right moves at the right moments can redefine what’s possible.
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