Johann Kroll, Hershey Bears (AHL, 2010)
Happy Wednesday,
Johann Kroll played college hockey at Ohio State, spent four years bouncing around the AHL and ECHL as a pro, and while he was doing all that, quietly earned one of the most rigorous financial credentials you can get: the CFA. Today, he runs Hockey Wealth, a firm dedicated entirely to helping professional hockey players manage their money. He's seen every mistake there is to make, and he has a checklist to prevent them.
This week, Jake and I sat down with Johann to get into all of it.
Players always think their careers are going to last longer than they do. And then all of a sudden, that actually was their last year making NHL money.
How They Got Here
Growing up in Minnesota: Learned to skate almost before he could walk. Hockey was everything.
Ohio State: Played college hockey, studied finance, and started thinking about what came after the game.
Minor league career: Spent four years bouncing between the AHL and ECHL. While still playing, knocked out all three levels of the CFA exam.
The turning point: Mid-to-late 20s, wife tired of him getting beat up and losing teeth, NHL dream fading. Time to pivot.
2014: Founded Hockey Wealth, a firm built entirely around helping professional hockey players manage their money. Twelve years in, still the only thing they do.
The Big Idea: Simple Beats Sexy (And the Data Proves It)
By the way, this doesn’t just go for professional athletes.
Everyone wants the flashy investment: the restaurant, the crypto play, the individual stock they're convinced is the next Tesla. And every advisor worth trusting will tell them the same thing: the data says no.
Here's why, and Johann explained it better than I've heard it before:
Most people assume individual stocks perform like the broader market: some do well, some do poorly, roughly in a bell-shaped pattern. That's not how it works. Individual stock returns are heavily skewed. The vast majority of individual stocks massively underperform the market. A tiny handful do extraordinarily well. And it's nearly impossible to identify those winners ahead of time.
So when you pick five or six stocks, you're almost certainly picking from the losing pile, while a diversified ETF portfolio quietly captures all of it, including the rare winners.
The problem isn't that athletes don't understand this. It's that simple, and boring is genuinely hard to sell to someone wired to compete and win. As Johann put it, to reach the highest level of hockey, you've spent your entire life trying to be better than average. Accepting that average beats individual stock-picking is psychologically brutal. But it's true.
5 Tactical Takeaways
1. The financial checklist nobody told you about. Johann's actual checklist for hockey players includes things most advisors never bring up:
Cross-border tax expertise (7 NHL teams are in Canada, US players need to understand RCAs, Canadian retirement compensation arrangements)
Maxing the NHL's defined benefit pension plan
Filling the post-tax bucket in the NHL 401 (k), up to $47,500 per year, that can be converted directly to a Roth IRA
Backdoor Roth IRA contributions on top of that
A non-retirement brokerage account for everything else
Tax planning, estate planning, and insurance reviews every single year
2. The career ending you're not planning for. Players always think the good years have two or three more seasons left. They almost never do. A GM gets fired, ownership changes direction, one injury ends everything, and suddenly the plan of "I'll save big at the end" collapses. The trap is assuming you'll see it coming. You won't.
3. Your social currency maxes out way before your fiat currency catches up. This is the frame Jake and I landed on that I think explains everything. The moment you become a professional athlete (even in the minors), your social status rockets to its ceiling. Everyone back home treats you like you've made it. But your bank account hasn't caught up yet. And that gap (between what people assume you have and what you actually have) is where the spending starts that gets guys in trouble.
4. The simple investments are the hardest sell. A low-cost, globally diversified ETF portfolio will outperform the overwhelming majority of individual stock-pickers — including professional fund managers. The data is not close. But it's almost impossible to convince a competitive athlete that the boring answer is the right one. That's exactly why having someone in your corner who can make this case with evidence matters.
5. Hire slow, hire right. Johann's one piece of advice for any player starting out: spend real time vetting the people around you. Interview your advisor. Interview other firms. Interview your agent. The decisions you make about who's in your corner in year one compound for the rest of your life — for better or worse.
Why It Matters
What stuck with me most from this conversation is something I've been chewing on since we wrapped. Hockey is genuinely unique compared to the other major sports. In football and basketball, elite talent is identified early and paid right away.
In hockey, a guy can be grinding through juniors, college, the ECHL, and the AHL into his mid-20s, technically a professional athlete the entire time, but making almost nothing. The social status is maxed out, but the money isn't there yet.
So when the money finally comes, the gap between what the world assumes you're spending and what you should actually be spending is enormous. And there's no one in most locker rooms walking them through what Johann just walked us through.
📩 And don’t forget: Bottom of the Ninth is back this Friday with the top three stories in sports and business from the week.
See you then,
Tyler & Jake