OP #328: The PayPal Mafia, But In Sports

Happy Tuesday OP Community-

I underestimated how crazy the weekends would become between graduations, graduation parties, end of the school year festivities, recitals, etc. I have no idea where time went but it’s certainly not on my side. In just 3 weeks, I’ll have moved my son into his dorm to start his summer program which kicks off his college career. With that said, I plan to treasure all of these events as they only happen a handful of times at best. With that said, I’ve had limited time for the OP… But here we are.

We are now 50% sold out for the Silicon Alley Sports Tennis Invitational on July 28. If any of you are tennis players and want to play with a great group of Silicon Alley folks, you can learn more and sign-up here. All monies left over from participating in our Silicon Alley Sports events go to our 2026 Impact Partner, Sandy Hook Promise. If you are looking for a vibe check from a similar event, check out our video and pics from our flagship event from mid-May.

Some fun links to get us started:

Notable NYers in the Latest Nike x Knicks Campaign (AMNY)
Knicks Partner Chased the Long Game and It’s Paying Off (Sportico)
The Watch Industry Has a Problem (Revolution Watch) → YT Video
LLM API Cost Comparison 2026 (Zen van Riel)
Making Meetings Suck Less (Rishad Tobaccowala)

Thanks for subscribing to and reading the Operating Partner!

Be well, do good.
Darren

The Band Gets Back Together

There's a story unfolding at Madison Square Garden that nobody in the business press seems to be paying attention to… but then again, most may not be from New York and may have totally missed the pre-season story-line.

Jalen Brunson, Josh Hart, and Mikal Bridges are leading the New York Knicks to their first NBA Finals in 27 years. They're doing it with all the hallmarks you'd expect: Brunson's late-clock brilliance, Hart's relentless hustle, Bridges' two-way versatility. But the analysts keep talking about matchups and metrics and minutes. They're missing the actual story.

These three men have been winning together since 2016. They shared a locker room at Villanova, won a national championship as freshmen and sophomores, and scattered into the NBA draft. Leon Rose didn't just build a roster. He reassembled a trust network. Hart arrived first, then Brunson signed, then Rose gave up five first-round picks to get Bridges back in the fold. Every move was deliberate. The talent was the table stakes but the pre-earned trust was the real acquisition.

If they win this thing, they'll become the first trio in basketball history to win both an NCAA and NBA championship together. That's remarkable. But the business lesson is older than basketball.

We see this pattern everywhere in high-performance organizations. The PayPal Mafia didn't just produce successful companies because those were talented people. It produced successful companies because those people already knew how to work together, how to argue, how to trust each other's instincts under pressure. Same story with the wave of operators who left one firm, dispersed for a decade, and then found each other again at the next platform. The reunion wasn't nostalgia. It was efficiency. You skip years of calibration. You already know who panics, who steadies, who you can hand the ball to with two minutes left.

In private equity, we see this when a strong management team follows a CEO from one portfolio company to the next. Boards sometimes view it with skepticism. I've learned to view it as a signal. If the people who did the hard work with someone in a previous chapter are willing to do it again, that's the most honest reference check in the business. Personally, I’ve seen it firsthand and the acceleration opportunity of a team who has worked together is tremendous.

Brunson talked about it after the conference finals: "We already share a bond and a brotherhood for life." He wasn't being sentimental but rather describing a structural advantage.

The Knicks haven't won yet. But they're playing with a currency most teams can't manufacture: trust that was earned somewhere else, a long time ago, under real pressure. Rose recognized it and built around it. That's the part worth watching, regardless of how the Finals end.