Val Ackerman played basketball at Virginia on a scholarship that was split in half. She got tuition and fees. Her teammate got room and board. One could go to class. The other could eat. That was 1977, and that was the deal, because there was only one scholarship to split.
She told me that on this week's show, almost as a throwaway line — this is just how it was — and then kept moving. But I stayed there for a second. Because the woman who went on to become the first president of the WNBA, who helped launch the 1992 Dream Team in Barcelona, who has run the Big East for twelve years — she started with half a scholarship. And between that half-scholarship and the WNBA, there were seven years. Law school. A Wall Street firm. Staff attorney at the NBA. Seven years of invisible work before she was in the room where anything got decided.
That's the episode. Not the WNBA history, not the CBA breakdown, not the Big East tournament at Madison Square Garden — though we got to all of that. The episode is about what it actually costs to cross over from athlete to executive. What the path looks like from the inside. And why the version most athletes imagine — walk in the door, be recognized, rise — is almost never how it goes.
The seven-year problem nobody talks about
Here's what Val said when I pushed her on the transition from player to executive: "You sort of have to go back down and say, 'Okay, I can't just walk in and be a CFO based on an NFL career.'"
That sentence is uncomfortable to sit with if you're me. I've had Warren Buffett say publicly that he thinks I should be on more boards. I've had internships — Elliott Hill at Nike in 2012, time with Stephen Ross. I have an engineering degree I put up there almost with my Super Bowl ring. And I still sit across the table from people who look at my resume and say do you have the experience? — and what they mean is the title. The CFO. The COO. The body of work that has a corporate name attached to it instead of a team name.
Val's answer wasn't you're wrong to want it. Her answer was: the path is real, but it has a shape, and the shape is longer than you think. She spent seven years building the credentials before she got the NBA job that eventually led to the WNBA. She wanted to go in-house at a sports league directly out of law school. She couldn't. She went to a Wall Street firm first, got her legal footing, buffed up the credentials she didn't have yet, and then made the move. "Seven years had passed. So I want to touch on that." That's what she said when I brought it up. Not seven weeks. Seven years.
Most athletes I know — myself included — are not psychologically prepared for that number. We're used to a different timeline. You put in the reps, you get the result. You train harder than everyone, you earn the spot. The feedback loops in sports are tight and visible. Corporate isn't that. Corporate is diffuse. You can work hard for three years and not be able to point to anything that looks like progress from the outside.
The humbling is the point, not the obstacle
What Val said next is the part I'm still thinking about: "Some athletes do it really well, and they're ready for that. And some athletes, I've seen some struggle — 'cause that's a hard transition."
She wasn't being dismissive. She was being precise. The transition is hard for a specific reason — the skills that got you to the top of your sport are real and transferable, but they transfer into different positions than you think. They open doors. They don't fill rooms.
The door opens because you've done something most people in that building can't do. They respect you for it. They're curious about you. That part is true, and I've lived it. But then you're inside, and the work is writing, and communicating, and navigating institutional politics, and building coalitions, and all of it is slower and less legible than anything you've ever done on a field. The persistence you learned in sports is useful here — but the persistence has to be applied differently. Toward different skills. Toward actually becoming the thing, not just arriving near it.
Val's analogy was clean: you can't be a lawyer without going to law school. You can learn some things on the job. But some things require the credential, and more importantly, they require the training underneath the credential. She wished she'd gotten her MBA when UCLA offered a combined JD/MBA in four years. She chose to get out in three. "I miss the full effect of some of the training." She said that plainly, without self-pity. It was just true.
I think about my own version of that. I left the field with a full engineering degree and an appetite for real estate development. I've been on job sites. I've talked to contractors and plumbers and electricians. I learned about cross-laminated timber not from a classroom but from a project. That field experience is real. But I'm also clear that there are rooms I haven't been in yet, and getting into them isn't just about the willingness — it's about the credential stack, built the right way, in the right order, over time that has to be earned and not rushed.
The two things Val actually said about NIL — and what she left unsaid
The conversation shifted to NIL toward the end, and Val made a point that I want to be precise about, because it's easy to hear it as praise and miss the edge in it.
She said financial literacy education is a requirement for schools now. Schools are supposed to be helping athletes navigate this space — advisors, guidance, the basics of what a 1099 means, what non-cash income means, why the free pizza from a brand deal is taxable. That infrastructure exists, or is supposed to exist. That's the floor.
But the ceiling — the part where an athlete actually capitalizes on NIL instead of just surviving it — that's something different. "The athletes at the end of the day really have to sort of step up on their own, and they've gotta be a little bit self-sufficient here."
What she means is this: the school can tell you to file a return. The school cannot make you curious. The school can put an advisor in front of you. The school cannot make you want to understand what the advisor is saying. I've seen this in the NFL — second, third, fourth-year players who've had the resources in front of them for years and still don't know what's in their own accounts, not because the information wasn't available but because they never felt urgency around learning it while the money kept coming in.
NIL is the same dynamic, just at 19 instead of 22. The kid getting $300,000 in a deal sophomore year — if nobody helps him understand what he's looking at, what the tax treatment is, what he's agreeing to in the contract he signed — the money doesn't build anything. It just passes through.
PULL QUOTE: "They've gotta be a little bit self-sufficient here in trying to figure out, if I'm gonna get into this world, I'm gonna have to surround myself with people who are gonna help me maximize, optimize the potential here, and also make sure that I don't fall into the traps." — Val Ackerman
The thing David Stern got right, and why it took thirty years to prove
Val gave David Stern all the credit for the WNBA. She was careful about it, the way people are careful when they're being precise rather than modest. She said he looked at what was happening in women's college basketball — the UConn-Tennessee rivalry, the Women's Final Four becoming a real event — and he said: women are going to be very important to the future of the game of basketball.
That was 1995. The 1996 Atlanta Olympics became the launchpad — USA women's team won gold, Lisa Leslie and Sheryl Swoopes and Rebecca Lobo gave the league its player pillars — and the WNBA launched the summer after. Stern had the clout with owners to get it moving. He told them it might not make money right away. He told them to play the long game.
What strikes me about that is that it took thirty years for the bet to look obviously right. Thirty years. There were teams that folded. Teams that relocated. Owners who gave franchises back because the money wasn't there. Val described the early pitch as selling the cause more than the sport — sometimes more the women thing than the sport thing — because the near-term profit case wasn't there yet. Now it is. Franchise valuations are moving. TV money is moving. The Portland Fire exists again in a city where I watched the first version disappear when I was a kid, sitting in the high seats because my mom worked at the Moda Center and she'd wave me down when the seats cleared out.
The lesson isn't patience as an abstract virtue. The lesson is that buy the long game and stay alive long enough to collect on it is different from be patient. David Stern stayed. The NBA kept investing when the returns weren't there. That's not patience — that's conviction backed by capital, sustained over decades. Most investors don't have that combination. Most of the ones who do become the ones the rest of us study later and call obvious.
What to actually do with this, if you're trying to make the transition
Three things, in the order they have to happen:
- Accept the timeline honestly, and then build backward from it. If Val's path took seven years from Virginia to her first NBA job, and she was already a lawyer, already deeply connected in basketball, already someone David Stern had his eye on — your path probably has a real number attached to it too. Not the aspiration number. The actual number, given where you are and what you still need to build. I've started doing this myself: not when do I want to be on boards but what does the person on boards actually have that I don't yet, and what's the shortest honest path to having it? The honest version of that question is harder to sit with. It's also the only version that leads somewhere.
- Go get the credential you're missing, even if it feels like going backward. Val said she wished she'd gotten the MBA. Not because she couldn't do her job without it — she clearly could — but because the training underneath the credential fills gaps you don't know you have until you're in the room where they matter. I'm seriously considering going back for a graduate degree in something that forces me to build the part of the skillset that field experience alone hasn't given me. The athlete instinct is to treat this as a step down. It isn't. It's the seven years, done intentionally instead of accidentally.
- Surround yourself with the people before you need them, not after. Val talked about the mentors who opened doors for her — men, at the NBA, when there were no women ahead of her to mentor her. She was deliberate about who she learned from. And now she's deliberate about being that person for the women coming after her. The lesson going both directions: you cannot wait until you need the network to build it. The advisor, the lawyer, the person who's been in the room you're trying to get into — those relationships have to be built before the moment of need. After the moment of need, they're not relationships. They're transactions.
Val left the WNBA because she was missing too many small moments with her daughters — I didn't miss many big things. I missed a lot of little things. She came back to the Big East twelve years later when her younger daughter went to college and the bandwidth opened up. She said the years in between made her a better leader than she could have been if she'd stayed.
I've been missing soccer practice on Wednesdays three weeks running. Val would understand that. She'd also tell me the Wednesdays are where it adds up.
The path is real. It just takes the time it takes.