Rich Kleiman told me he walked into a dinner at Ben Horowitz's house — Steve Stoute had set it up, Kevin's first birthday in the Bay, a welcome-to-the-Valley moment — and didn't recognize half the room. Ron Conway was there. Neal Mohan. Bill Gurley. The who's who of Silicon Valley, all in one place because Kevin Durant was in one place, and Rich was the guy who came with Kevin.
So Rich did what Rich does. He started asking questions. Not networking questions — real ones. Conway started listing investments, seed rounds, Series A's, IPOs, and Rich stopped him. "Yo, I don't even know what a seed or a Series A is. Like, straight up, I just don't know."
Conway looked at him. Then he started explaining.
That's the episode. Not the $100 million deals. Not the lifetime Nike contract or the PSG investment or Boardroom or 35 Ventures. Those are outputs. The episode is about what made those outputs possible — and it's a thing almost nobody building around an athlete actually does.
The thing agents don't understand about their own job
Most agents are transactional by design. That's the model. Negotiate the contract, collect the commission, move to the next client. The whole structure — the incentives, the workflows, the way agencies are staffed — is built around deal volume. Rich understood this about himself before he understood much else: he didn't have agent instincts. He had manager instincts.
The difference is not a personality thing. It's a time horizon thing. An agent extracts maximum value from the current moment. A manager invests in the architecture that makes the next moment worth more than this one.
When Rich got to KD through Wale — and the timing mattered, everything in his story is about timing — he was being asked to be an agent but he brought a manager's frame. He watched Kevin show up miserable to a Sprint commercial, look like someone had asked him to do something pointless on his day off, and rather than saying well it's in the contract, Rich said: do you wanna do this?
Kevin said no.
Rich said: you don't have to.
That's a $0 decision that, compounded across a decade, is probably worth nine figures. Because the version of KD who never had to do the Sprint commercial is the version who had the energy and the buy-in to build something real — to be a genuine partner in 35 Ventures instead of a name on a letterhead. You cannot build an empire with someone who's grinding through obligations they resent. You can only build one with someone who's actually present.
Relationships are long or they're nothing
Rich didn't grow up knowing the right people. He grew up being the kind of person who knew everyone. There's a difference, and it matters. His version of currency as a kid in New York wasn't access — it was the ability to walk into a room and make something real happen without asking for anything.
He ran a bookie operation in college not because he needed the money but because the structure clicked. The idea of running this company, having a system in place, having a structure — something in him lit up. It wasn't the gambling. It was the running of it. That instinct — understanding what makes a small operation hold together — is the same one that built Boardroom. The category changed. The wiring didn't.
What I noticed in the conversation was how specifically Rich talks about non-transactional relationships. He doesn't mean "be nice." He means something precise: let me not ask this person for anything right now, because if the relationship is real, we're both going to ask each other for things eventually. The ask comes later. The connection comes first. Most people in this business try to collapse that sequence, and then they wonder why the relationship feels hollow the second the deal is done.
Jay Brown was that for me. I watched him work from the outside — introduced to Jay-Z early, sitting in the room at Roc Nation, and I kept noticing the guy in the corner making moves nobody was watching. Managing her. Managing him. Quietly. I started paying attention to how he moved before I ever really understood what he was building. That observation — that shadow study of someone operating at a level you want to reach — is its own education. Rich called them "watch mentors." People you study rather than people who hand you a playbook.
Jimmy Iovine was one of his. He never said Iovine sat him down and gave him the game. He said he watched how Iovine moved and made a mental note.
PULL QUOTE: "My mentors were people that I watched. I see how Jimmy Iovine moves. I get it. I'm gonna make a mental note of that." — Rich Kleiman
The stopgap is not a failure. It's information.
Rich hit a wall in the music business. He was in the room — A&R on J. Cole's first album, managing Solange, Meek Mill, Wale, in the studio with Jay — and somewhere in there stopped feeling like himself. The confidence he'd built from the street to the DJ booth to the label stalled. He couldn't name exactly why. He just knew he wasn't all the way present.
That experience is the reason he could eventually be completely himself with Kevin Durant. The two things are connected. You can't appreciate what it feels like to operate at full confidence until you've spent time operating at partial confidence and felt the drag of it.
He described the moment with KD as: I feel all the way myself. He wants me around him. And this is one of the best in the world. That convergence — the person who makes you most yourself also happens to be the best in the world at what he does — is the kind of alignment most people spend their whole career trying to find and never do.
I think about my own version of that. 2008, Nebraska, my dad's business getting hit by the financial crisis, my mom telling me to stay in school if I wasn't coming back to finish. At the time, staying felt like the conservative choice, the fearful choice even. It turned out to be the choice that gave me time to become the player who went second overall instead of late first. The stopgap had information I couldn't see from inside it. Rich's stopgap in the music business had the same thing — it was pointing him toward sports, toward Kevin, toward the work he was actually built to do.
The mistake isn't hitting a wall. The mistake is treating the wall like a conclusion instead of a redirect.
What "building an empire" actually means day-to-day
People hear Kevin Durant — Boardroom, 35 Ventures, PSG, Philadelphia Union, Gotham FC, lifetime Nike deal, venture fund, real estate, public equities — and they think about the portfolio. They don't think about what manages the portfolio.
Rich broke down 35 Ventures on the show and it's a family office in every meaningful sense: all of Kevin's investments, brand deals, on-court and off-court work, foundation, legacy planning — managed as a single integrated structure. The goal isn't maximum return on any single deal. The goal is architecture that runs well without Kevin having to touch it daily, so that on the days Kevin does engage, he's engaging because he wants to rather than because he has to.
That design distinction — I'm building this so it works whether you're paying attention or not — is what separates a real family office from a collection of deals. Most athlete business portfolios are the latter. They're accumulated opportunistically, each deal signed because it seemed good at the time, with no connective tissue. Rich's model is the opposite: every investment feeds the flywheel. PSG gives Boardroom cachet. Boardroom gives 35 Ventures brand surface. The foundation gives KD a community anchor. None of it is accidental.
The day-to-day is also less glamorous than people picture. Rich reads Kevin well enough to know when to push information and when to back off. Some weeks he's giving him the full run of show. Other weeks he's just calling to talk about basketball, or not calling at all because he can sense the space is needed. Once or twice a year, a formal state of the union. That rhythm — knowing when to show up and when to let things breathe — is relationship intelligence that you can't buy or hire.
What I'd actually take from this, building my own
Three things from this conversation that changed how I'm thinking about my own next chapter:
- The partner question comes before the structure question. Rich didn't find Kevin and then build 35 Ventures. He found Kevin — meaning the person he was completely himself around, the person whose standards forced him to raise his — and then built everything else on that foundation. I've been thinking about my own post-football work mostly in terms of categories: what industries, what deals, what asset classes. This conversation flipped it. The right question first is: who are the one or two people I can build with where the relationship itself makes both of us sharper? Everything else is downstream of that.
- Ask the dumb question. Especially in the rooms where it costs you something. When Ron Conway was sitting across from Rich listing deal structures, Rich didn't nod along. He stopped and said he didn't understand the terminology. In hindsight, he says he must have sounded like an idiot. What he actually did was the only thing that works with someone like Conway — he was completely real. I sat in cash from 2010 to 2012 because I refused to invest in things I didn't understand and didn't ask enough questions to get there. I've talked about the opportunity cost on that before. It was real. Rich's version of that lesson is better because he learned it going forward instead of looking back.
- The financial architecture is necessary but not sufficient. Rich said it plainly: Kevin retires financially straight. The family office structure works. The investments have gained value. The lifetime Nike deal doesn't expire. All of that is real and it matters and it took years to build. But it accounts for maybe 40 days of the year. The other 325 — what fills those? What makes a person who has competed at the highest level every day of their adult life feel like it was worth getting out of bed? That question doesn't have a financial answer. It has a purpose answer, and it's the one nobody builds the structure for. Rich doesn't know Kevin's answer yet. I don't fully know mine. But being honest about the question is the only way you eventually find it.
Rich ended the conversation with something I'm still thinking about. He said when athletes like me and Kevin retire, we go from being old to young. Old in football, young in real life. I'm 37 years old and I've been playing professional football since I was 22. Whatever comes next — I am, in every meaningful sense, just starting.
That's not a comfort. It's a responsibility.