OP #304: The Two Types of Winners

What a former world #3 taught me about leadership, growth, and why execution always beats flash.

Author

Darren Herman
July 29, 2025

I’ll admit it—this week didn’t follow my usual OP rhythm. Back-to-back final round interviews at a portfolio company, late nights prepping cases, and a sports event that ran hotter than expected (literally and figuratively). But if you’re going to break the routine, make it worth it. And this week delivered.

At the Silicon Alley Tennis Invitational, something happened that I’ve been thinking about ever since. It involved one of the best tennis players of the modern era, a few smart questions, and two quotes that stopped me mid-conversation to jot them down in my phone.

I unpack it all below.

But first, a few links to kick off OP #304:

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Darren

What a Former World #3 Reminded Me About Growth

We had a bit of a surprise this year at the Silicon Alley Tennis Invitational. After a full day of matches and too many electrolyte gummies, we introduced our guest of honor: Milos Raonic. For those outside the tennis world, Milos isn’t just a former Wimbledon finalist—he’s an eight-time ATP title holder, once ranked #3 in the world, and statistically one of the greatest servers in the modern era. He’s the kind of player who made opponents dread second sets.

Milos didn’t just show up to speak—he played with us. He rallied, volleyed, and brought a quiet intensity that reminded you instantly: this guy has shared courts with Federer, Djokovic, and Nadal—and held his own. After the matches wrapped, Cammy Keiler, a longtime member of the Silicon Alley Sports community, sat down with Milos for a fireside chat. She asked great questions. The audience followed up with better ones.

Two of Milos’s answers stuck with me long after the event ended.

“Extraordinary results come from doing the ordinary things exceptionally well.”
That’s not just a tennis insight. That’s a growth-stage mantra.
In portfolio companies, we love the shiny new playbooks—AI tools, GTM hacks, brand reinventions. But the truth is, compounding happens in the fundamentals: how you run pipeline meetings, how you onboard a new hire, how fast your team closes the loop with customers. The best operators aren’t magicians. They’re relentless in their discipline. They find leverage in the repetition. That’s where greatness hides—inside the blocking and tackling. It’s boring, until it’s not. When you are winning, it’s hard to be bored.

“There are two types of winners: those who like winning and those who hate losing.”
This one hit a little deeper.

I’ve worked with both. And you’ve seen them, too.

The ones who love winning are vision-builders. They’re future-focused. Think Brian Chesky at Airbnb, who turned a broken travel industry into a design-first experience platform. Or Whitney Wolfe Herd, who didn’t just start Bumble to win a dating app war—she built a movement around a safer, more empowering social dynamic. These leaders are magnetic. They rally teams around what could be. They attract talent, investors, and even skeptics, because you want to be part of their version of the future.

Then there are the ones who hate losing—the edge players. Think Travis Kalanick at Uber in the early days. Or Susan Wojcicki, quietly outmaneuvering every digital media competitor to make YouTube the platform of the decade. This archetype is relentless. Data-obsessed. Borderline paranoid. Their intolerance for failure creates a culture of sharp execution and high urgency. They outwork everyone not because they crave the trophy—but because they refuse to be second.

Both styles win. But they lead differently. And if you’re building a team or backing a founder, it’s worth asking: what’s driving them? Because the fuel that gets you from zero to one doesn’t always scale from ten to a hundred.

I left that night thinking: maybe the best leaders learn to use both muscles. They fall in love with winning—but they never get comfortable with losing. That’s the edge.

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

The Substack AI Report (On Substack)

Thank you again for subscribing to the OP. It’s been a hectic week but look forward to bringing you some great content next week as I get back into the swing of it all.

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