At 18 years old, freshly drafted, first-round money in his pocket, Dexter Fowler got a job at a golf course.
Not because he needed it. Not because the signing bonus ran out. He got it because he was in Casper, Wyoming — which is not Atlanta, which is not anywhere he'd ever been — and there was downtime, and he needed to fill it with something. So he showed up, cleaned clubs, drove carts around, talked to people. The guys at the course recognized him. They knew what he'd signed for — signing bonuses are public — and they'd ask him: why are you working here?
He didn't have a complicated answer. He was bored. He wanted to meet people. He wanted to learn the game his dad played. That was it.
But that simple answer is the entire episode. Because the guys who told him why are you working here — the ones who showed up on Saturday mornings with their bags and their business and their networks — became part of what Dexter Fowler has now. The relationships that put him in the room with Bill Foley. The relationships that put him in a Premier League ownership group. The relationships that gave him a mentor who called him and said Dex, you gotta get in on this before the deal was even public. That golf course in Casper, Wyoming, in the summers when all his friends were home from college and he was the only one on a different schedule — that's where part of it started.
The one idea this episode kept circling, even when it sounded like it was about something else: the people who end up in the right rooms didn't get there by networking. They got there by showing up to places they didn't have to be, as someone they didn't have to be, and doing that long enough for the right people to notice.
The 70% rule nobody talks about
Before we get to rooms and relationships, there's a foundation question, and Dexter answered it more directly than most guests do.
He saved 70% of every check. Not as a goal he was working toward. As a practice, from the beginning. The 30% that wasn't going into stocks and investments was the operating budget. Everything else was hands-off, deployed and growing while he was still playing.
This matters because it runs counter to what we usually talk about when we talk about athlete finances. The conversation defaults to: what did you buy first? What did you lose? What do you wish you'd done differently? Dexter had the Range Rover story — his dad told him to lease, he bought it in cash because he wanted it to be his, and two years later a new model came out and he understood what depreciating asset actually meant in his stomach rather than in theory. So yes, he had that version of the story.
But the Range Rover wasn't the story. The 70% was the story. He said it matter-of-factly, the way you say something that's just true: I saved 70% of what I make. No drama around it, no lecture about discipline. It was just what he did, modeled on watching his parents budget at the kitchen table in Alpharetta, watching them sit down and assign every dollar before it left the account.
I grew up in a similar house. My mom was a teacher too — first and second grade. My dad ran a business that the 2008 financial crisis hit hard, and I watched my parents navigate money carefully in ways that didn't look like scarcity but were, in fact, very intentional. I stayed at Nebraska an extra year partly because of that — I had a shot at the draft early, and my mom told me if I left school I had to finish, and I told her if I left I wasn't coming back, and she told me then I was staying. I stayed. By the next year I was projected second overall.
The point isn't the draft slot. The point is that the discipline to hold a line — this percentage is for living, the rest is not available to me right now — doesn't come from financial advisors. It comes from watching how your parents handled money before you had any of your own. Dexter watched budgeting happen in real time. He kept birthday checks for two years before anyone made him cash them. The instinct was already there when the first-round money arrived. You can't install that instinct in the locker room. You either brought it with you or you're building it from scratch, and building it from scratch is slower and more expensive.
What Bill Foley actually taught him
Here's the part that doesn't get told cleanly enough: Dexter didn't go find Bill Foley. Bill Foley was his neighbor. The realtor mentioned it almost as an afterthought — you know Bill Foley lives right there? Dexter didn't know who Bill Foley was.
What happened next is what the whole episode is really about. He saw Foley at the golf course. He introduced himself. He brought a gift over. Foley invited him to a hockey game. They had dinners. They built a friendship. Five years before I retired, Dexter said, Bill would tell me, "I got something for you when you're done." Five years. No agenda, no pitch, no transaction. Just someone who saw something in Dexter and kept a door open.
When retirement came, the door was still open. That's when the board work started. That's when Bournemouth happened. That's when the network that Foley had built over decades became something Dexter could access — not because he'd asked for it, but because he'd never asked for anything. I've never asked my network for anything. He said it like it was obvious, like the grammar of it was just correct. You build friendships first. Good people do good business together.
I want to sit with this for a second because I think it describes something true that is almost never said out loud. The version of networking that most people practice — the version that gets taught in business schools and sales training — is transactional from the start. You identify the person who has the thing you want. You find a way into the room. You make your ask. That works sometimes. But it doesn't produce what Dexter has with Foley, which is a mentor who proactively calls you and says you should get in on this at this amount, who has been watching your development for years, who trusts your judgment because he's observed you operating without an agenda long enough to know who you actually are.
PULL QUOTE: "I want a friendship first, and then we can... I believe good people do good business together." — Dexter Fowler
The golf course job in Casper and the neighbor in Nevada are the same story twenty years apart. Show up somewhere you don't have to be. Do it without an agenda. Stay long enough for people to see you clearly.
Other people's mistakes are free tuition
Dexter said something in the middle of the conversation that I keep coming back to. He was talking about how he learned to invest, how he avoided the moves that derail athletes, and he said: everybody else's problems are Cliff Notes to me.
He didn't mean it dismissively. He meant it as a genuine learning methodology. When he saw a player lose money in a bad deal — whether in the stock market, in a business that went wrong, in a trust that got broken — he asked why did that happen rather than that's a shame. He reverse-engineered the failure so he didn't have to replicate it. He watched his older teammates, studied what the guys who retired well had done differently, and built a mental model from observed outcomes rather than his own trial-and-error.
This is unusual. Most people want to learn from their own experience because their own experience feels real and other people's experience feels abstract. But other people's financial mistakes are not abstract — they have specific causes, specific decision points, specific moments where the path forked. If you're willing to do the work of understanding the why rather than just absorbing the headline, you can skip entire chapters of expensive learning.
He came into the majors with a foundation already set because he'd watched people operate before he had to operate himself. The 70% rule, the foundation in index funds and stocks before the venture stuff, the decision not to invest in a passion just because it was his passion — if it don't make dollars, it don't make sense — all of it was built on watching other people make the move wrong first.
The thing the cart tender became
Three things I took from this conversation that I think are worth writing down:
- Build the foundation before you build the portfolio. Dexter didn't start doing venture deals and soccer team investments while he was playing. He was saving 70%, putting it into stocks, building something boring and stable. The interesting stuff — the Premier League ownership, the SPAC boards, the management company, the RIA — came after the foundation existed. The sequence matters. You can't take intelligent risk on the frontier of your investing if you don't have a base that doesn't require those bets to work. Most young athletes skip the boring middle stage because it's not visible. Nobody posts their index fund allocation. But that boring middle stage is what funds the fun part, and it's what Dexter had when the opportunity came and he needed to write a check quickly enough that Bill Foley knew he was serious.
- Relationships compound, but only if you never cash them out. The people in your network who will actually move for you — who will call you with an opportunity before it's announced, who will vouch for you in a room you're not in — are the people who have never felt transactional in their relationship with you. The moment you treat the relationship as a vehicle for an ask, you convert it from a compounding asset into a one-time transaction. Dexter's phrase for this was simple: I've never asked my network for anything. The result is that his network has never stopped offering.
- The second job is the signal, not the income. The golf course job wasn't about money. It was about what kind of person Dexter Fowler was at 18, flush with a first-round signing bonus, in the middle of nowhere, deciding what to do with unstructured time. He got a job. That's the thing that explains the rest of the story. Not because working a cart job builds financial skills — it doesn't, really — but because the person who gets a job when they don't have to is the same person who shows up to a meeting that isn't required, who introduces himself to the neighbor he doesn't recognize, who stays at the table after most people have moved on. The signal was always there. The World Series ring and the Premier League stake are just later data points on the same curve.
There's a moment near the end of the conversation when Dexter talked about inclusion — about being the guy who went to sit with the kid eating alone at lunch, who got annoyed when teammates went to a country concert without asking if he wanted to come. You didn't ask. He said it simply, not as a complaint. As a principle.
That's the whole thing, really. You don't know who someone is until you ask. You don't know what they want, what they're building, what they'd be good at, whether they'd be worth knowing — until you treat them like they might be. Dexter's been doing that his whole life. The answer keeps surprising people.
It doesn't surprise me.