Mark Notarainni has three kids who played college sports. One of them landed in the NIL era. Mark runs the Consumer Group at TurboTax. By any measure, his son had every possible advantage — a father who lives inside the tax system professionally, a house where this stuff got talked about at the dinner table, access to the right information before the money ever arrived.
His son was still surprised by the bill.
That's the thing I keep coming back to from this conversation. Not the product features, not the AI tools, not the credit score gamification — though all of that matters and we'll get to it. The thing I keep coming back to is that Mark's son, with a TurboTax executive for a father, still didn't quite see the 1099 bill coming. If that's what happens when you grow up with the information, imagine what happens when you don't.
The W-2 lie most people never question
There are two kinds of earners in this country, and the system is designed to make one of them invisible to themselves.
W-2 employees — people like Mark, like most of the people reading this — get taxed before they ever see the money. Two weeks, paycheck, taxes already gone. They file in April, most of them get a refund, and the whole machine feels like it's working in their favor. It is. The friction is built in. The money that belongs to the government never makes it to your account in the first place, so you can't spend it, can't confuse it for yours, can't show up in April owing a number you weren't expecting.
1099 earners — freelancers, self-employed people, and now every NIL athlete in the country — get the whole check. All of it. No withholding, no deduction, nothing pre-removed. The money lands, it looks like it's all yours, and the government's portion sits in your account for months looking indistinguishable from money you can actually spend.
Mark put it plainly: "As the revenue is coming in, they think it's all theirs."
That sentence is the episode. Not the tax code, not the filing mechanics, not which software you use. The psychological trap is that the money in your account after a 1099 payment is not fully your money, and nothing in the experience of receiving it tells you that. There's no deduction line. There's no withholding notice. There's just a number that goes up, and a bill that arrives months later after you've already spent the portion that belonged to someone else.
For an NIL athlete getting their first real paycheck at 18 or 19, this isn't a discipline problem. It's a system problem. The W-2 world has the discipline built in structurally. The 1099 world requires you to supply the discipline yourself, from scratch, with no institutional support, right at the moment when you're least equipped to do it.
The jock tax is the most complicated version of this problem
I've been paying taxes in multiple states my entire NFL career. Every game in a different city meant a different state tax obligation — you're taxed where you earn, not just where you live, and for an NFL player that means you're filing in potentially a dozen jurisdictions every year. We call it the jock tax. It's one of the more genuinely complex tax situations that exists for any individual earner in the country.
Now multiply that by the fact that games are increasingly happening overseas. When I was playing and we had a game in London, that wasn't just an NFL game — that was income earned in the United Kingdom, with its own tax framework, its own rules, its own filing requirements layered on top of everything else already in motion. Now there are games going to Australia, to Madrid. The international dimension of this is expanding every year, and almost none of the players stepping off that plane have thought through what it means for their returns.
I'm not saying this to be dramatic about how complicated my situation was. I'm saying it because the jock tax is really just the extreme version of the same problem every 1099 earner faces: income arrives from multiple sources, in multiple forms, subject to multiple rules, and the only person who has to integrate all of it is you. The W-2 employee doesn't have to think about this. The self-employed person does. The NIL athlete does. The NFL player doing endorsements on top of their contract does.
The complexity compounds. Most people don't have a system for complexity. Most people have a system for simplicity — they've built something that works when the income is one source, one type, one jurisdiction. The moment any of those variables multiplies, the system breaks.
Credit is the other side of the same coin
We spent part of the conversation on credit scores, which might sound like a detour from taxes, but I don't think it is. They're two faces of the same underlying thing: the financial system is already running, whether you're paying attention to it or not, and your relationship to it is being scored in real time.
My mother put me as an authorized user on her credit account when I was eight years old. I got to college — got to the pros, actually — and when they pulled my credit, the score was close to 800. I had no idea why. Mark laughed and explained it: there was an account in the system with my name on it going back to 1994. My mother had been building my profile for years before I even knew what a credit profile was.
That's not normal. Most people my age didn't have that. Most people show up to their first real financial moment — first apartment, first car loan, first business line of credit — with a thin file or no file at all, a score in the 500s or 600s, and no idea why it matters or how to fix it.
What I've come to understand is that the credit score is really a record of your consistency. It's the financial system's answer to the question: does this person do what they say they're going to do, repeatedly, over time? That's it. Every on-time payment is a data point in your favor. Every missed payment, every maxed card, every account sent to collections is a data point against you. The system is always watching. Most people just aren't watching back.
Mark's kids have Credit Karma on their phones and they compete with each other on their scores. That's actually the right instinct — making a game out of something that most people find either boring or terrifying. The score goes up, your phone tells you, it feels like a win. That feedback loop works. The problem is most people never start.
PULL QUOTE: "When you can demystify it — you are the cog in the wheel. Everyone is fearful that it's kind of done to them. That's actually not true. You're in control." — Mark Notarainni
What AI actually changes here — and what it doesn't
Mark is careful about this, which I appreciated. He doesn't sell AI as a magic solution. What he describes is more precise: AI makes personalized advice scalable for the first time.
The old version of financial guidance looked like this: you either had enough money to pay for a good accountant and a good advisor, or you didn't. If you did, you got a plan tailored to your situation. If you didn't, you got a generic TurboTax walkthrough and a refund you probably spent on the wrong things. The gap between those two experiences was enormous, and it tracked almost perfectly with who was already doing okay financially and who wasn't.
What AI changes is that the analysis that used to require a paid professional can now be done at scale. Credit Karma's debt agent — which Mark mentioned, pointing out that 57% of their customer base carries revolving debt — doesn't just tell you that you have debt. It looks at your specific debt, your specific cash flow, your specific credit profile, and builds a plan. Then it executes the plan. Not gives you a PDF to think about. Actually executes it.
That's real. That's a genuine change in who has access to the kind of financial thinking that used to require a retainer.
What AI doesn't change: you still have to be paying attention. The tool only works if you engage with it, trust it with your data, and then actually do what it tells you. The athletes who get surprised by their NIL tax bill in April — AI doesn't save them if they never opened the app. The discipline has to be there before the tool is useful. The tool amplifies existing intentionality; it doesn't create intentionality where there was none.
What I'd actually do, starting now
Three things — for the NIL athlete, the young player, the small business owner who just started and is figuring this out:
- Treat 30% of every 1099 check as already spent before it arrives. This isn't a suggestion, it's a floor. The self-employment tax rate alone, before you layer on state taxes, can eat 25-35% of your gross. The money goes into a separate account the day it arrives — not a savings account you're tempted to dip into, a designated tax account you treat as off-limits. This is the W-2 workaround: you manufacture the withholding yourself because the system won't do it for you. Mark's son at Boise State — who grew up with a TurboTax executive for a father — still got surprised. The only fix is making the discipline structural before the bill lands.
- Open Credit Karma today, not when you need it. Not when you're applying for a car loan, not when you're trying to qualify for a mortgage, not when the number is already low and you're panicked. Today. The credit score is a lagging indicator — it reflects decisions you made months or years ago, which means the only time to start building it is before you need it. My mother started building mine when I was eight. You probably can't go back and do that, but you can start now. The authorized user trick she used on me — getting added to a responsible parent's account, or a partner's, or a trusted friend's — is still the fastest legitimate way to get a thin file off the ground. After that, consistency does the work.
- Pick one financial tool and actually use it — not three tools you open twice. I went through years of sitting in cash because I didn't have a team I trusted yet to translate the options. I missed one of the biggest market rallies of my lifetime in 2010-2012 because I refused to put money into something I didn't understand. That opportunity cost was real. The lesson wasn't "trust blindly" — the lesson was "have a tool, have a system, and actually engage with it." Whether it's QuickBooks for your business, Credit Karma for your credit picture, or TurboTax to make sure your filing reflects your full situation — pick the one that matches your biggest gap and use it consistently. Consistency with one tool beats sporadic attention across five.
My dad used to tell me to set money aside before you think you need to. Put it somewhere it earns while you're not using it. He kept telling me that when I was still in the league. He kept telling me that even in the years when I was fighting retirement, the years when I didn't know yet that I was walking away because I needed to be close to him before he was gone.
I'm grateful I listened to him about money. I'm more grateful I listened to him about time.
The tax bill is the easy part. The system already exists to help you manage it. What it can't do is care on your behalf.
That part is still on you.