We’re going to switch up the format a little this week. No Deal Sheet, No Off the Court, no Drop. Just a conversation.

I teased this for the past few weeks, but here it is: a former top-100 tennis pro on what the sport actually pays, why equity was rarely discussed during his era, and why the athletes with the most to gain from thinking like owners aren't the superstars. Welcome back to The Closeout. Let's get into it.

I recently sat down with Jeff Salzenstein, a former ATP world No. 100. He hit that ranking at the age of 30, the oldest American man to crack the top 100 for the first time, after two injuries that should have ended his career. His path was one almost nobody takes: a Stanford economics degree, a college run that took him from No. 5 on his own team to No. 1, and a pro career he funded largely out of his own pocket. The week he broke the top 100, he won a Challenger title in León, Mexico, and cleared about $3,000 after expenses. Today, he’s a leadership speaker and performance coach in Denver.

Jeff sits on the exact fault line this newsletter covers. Building a personal brand in his era was an uphill battle. Today's players can turn a phone and a following into equity, ownership, and companies that outlast their careers. We talked about what changed, what it cost him to come up the way he did, and which current athletes he thinks are playing it right. 

The conversation below is lightly edited for length.

Q: You hit No. 100 at 30, the oldest American to do it for the first time, after two major injuries. What was the financial reality at that level?

A: The tennis world is one of, if not the most, competitive environments to make a living in. In another sport, a top-five college player gets drafted and catapulted straight into the starting lineup with a guaranteed contract. In tennis, you're starting at the lowest level, below the G-League, trying to prove yourself. I graduated from Stanford, shot up from 800 to 150 in the world, got a wild card into the US Open, and played Michael Chang at 23. Then I had two career-threatening injuries right as I was about to break into the top 100. Instead of being on the shelf for a year and coming back to a guaranteed $15 million contract like in other sports, I went broke. I had to pay my own bills with no income coming in. It's the worst business model in sports: only the top 1% are crushing it. I did it for the love of the game, not the money.

Q: In your era, when players made real money, where did it go? Was equity ever part of the conversation?

A: I'd put the players in four buckets. The elite legends: Agassi, Sampras, Federer, they were starting to build brands, but even Federer's brand-building really emerged late in his career. Below them, players making a good living but not famous, guys clearing $100-300K a year, were mostly putting it in the stock market. Then there was my group, scraping by, reinvesting everything back into myself, no leftover cash for stocks, let alone equity. And the fourth bucket was sleeping in cars, making nothing. Equity, building a business, being part of a brand, that just wasn't the conversation. Social media, NIL, private equity, all of this has changed the game completely from when I competed.

Q: Coco Gauff has equity in Naked Juice, a stake in Unrivaled, a company she owns outright. Is this a shift in how players think and operate or have the structures around athletes evolved?

A: It's pretty simple: the emergence of social media changed everything. We didn't have it. I had a racket deal and a clothing deal, most of my career I was just getting free Nike gear, not getting paid. One of the first athletes to really do the equity deal was Michael Jordan with Nike. Messi's doing the same thing. It's brilliant to tie it to your performance and results, and that wasn't the conversation when I played. Coco's team is learning from the Jordans and the Agassis who came before. And they're watching college athletes build brands on their own, all they need is a phone and a following, and the brands come to them, because that's where the eyeballs are. Look at Spencer Jones, who plays for the Denver Nuggets. He's documented his whole summer investing in companies, traveling to learn about entrepreneurship, at 24, 25 years old. That wasn't what we were doing.

Q: What do athletes still fundamentally not understand about their own leverage?

A: If you're not a Coco Gauff with a team around you, if you're flying blind and just randomly posting about what you ate for breakfast, you're missing it. People are watching everything. Every choice you make impacts the world's perception of you. A lot of athletes don't have that self-awareness yet. With AI and social media, people can sniff out a lack of authenticity quickly, you can fool them for a while, but eventually they figure out if you're not the real deal. The good thing about sports is you can't hide, your results speak for themselves on the court. But off the court, the younger athletes who get personal growth early and build an authentic, energetic brand, the opportunities come to them, business deals, equity deals, because they're aligned with someone doing the right thing. You can hide for a little while. You can't hide anymore.

Q: Is there anyone doing this particularly well right now who isn't getting mainstream coverage?

A: Spencer Jones is one of the first athletes I've really been paying attention to around this. You can tell he's being very thoughtful and forward-thinking, like, "I may get cut next week, so let me build now." You hear the tragic stories, NBA and NFL players worth a hundred million who are broke five years later. There were athletes doing what Spencer's doing back in my era too, we just didn't know about it, because it wasn't on LinkedIn or Instagram. Now he gets that exposure, and younger athletes see him doing it. Here's the interesting part: it can actually be better for those non-superstar athletes to spend more time on the business side than the elite guys at the top of the game, because they don't have the same infrastructure, money, and team around them. They have to make up for it and think about the future. The superstar can focus purely on their sport because they've got a team handling the brand. The guy who knows he's not going to be Michael Jordan? He's the one who needs to be leveraging this now.

Jeff played eleven years of professional tennis on tour, landed in the top-100 in the world, and is watching young up-and-coming athletes build brands and portfolios with tools at their disposal he never had. Coco Gauff’s equity stakes and meteoric potential at 22, Spencer Jones investing at 25, is all proof that the thing he had to learn the hard way after retiring at 33 is starting to get taught at 18.

That's the whole shift in one interview. Jeff put it plainly: "It's not about TV revenue as much anymore. It's about being on social media, the attention, the eyeballs." The smart ones are already treating that as an asset, not a distraction.

Thanks to Jeff for the time and the candor.

The full conversation is on YouTube, including Jeff’s take on today's agent landscape and what he'd do differently at 22. [Watch it here]

P.S. Jeff's got me thinking about this one. What athlete or artist do you think is leveraging their personal brand best? Hit reply, curious what you all think. See you Wednesday.