What I Wish Someone Had Told Me When I Was Starting Out

By Matt Coy, VP of Experiences — CUENTO Marketing

I had great mentors. People who taught me how to shoot, how to direct, how to run a crew, how to lead a production. I was lucky in ways I didn't fully appreciate until much later in my career.

But even with great mentors, there were things nobody told me early on, things that had nothing to do with cameras, rundowns, or show calling, and everything to do with building a sustainable life in an industry that doesn't look like most others

This is for anyone starting out in sports production and game presentation. Not the craft, there’s plenty of advice out there about that, and most of it you'll learn on the job. This is about the things that don't feel urgent at twenty-two, but that quietly shape what your life looks like at fifty.

This Business Doesn't Run on a Calendar

Games happen on weekends, holidays, birthdays, anniversaries and eventually, for some of us, on the day of a wedding or a funeral we wish we could attend but can't because the schedule was set a year ago and doesn't move. Most people figure that part out quickly.

What takes longer to figure out is what that schedule does to everything in life that runs on its own calendar, taxes, retirement contributions, insurance enrollment windows, financial planning. None of that pauses because you're on the road for three weeks or working seven days straight during the playoffs. And if you're freelance or working as an independent contractor, which most of us are for at least part of our careers, there's no HR department quietly handling any of it in the background.

Early on, I didn't think about any of this. I was too busy being thrilled that I got to do this for a living. That's exactly the problem, the things that feel least consequential when you're young and busy are often the things that matter most thirty years later.

Get a Good CPA Now, Before You Think You Need One

If you do freelance or independent contractor work in this industry and at some point, most of us do, a good CPA is not optional. It's one of the most important professional relationships you'll have, and most people in this business don't get one until after they've already made costly mistakes.

A generic accountant, or tax software, often isn't enough, because our income doesn't look like a normal job's on paper. You might work for a dozen different teams, leagues, and production companies in a single year, each handling tax forms and withholding differently, or not withholding at all. You might work internationally, which adds a layer of complexity most accountants never encounter. And you have real business expenses, travel, gear, home office space, union dues, professional development, that someone unfamiliar with gig and event-based work may not know how to handle correctly, either leaving money on the table or creating problems down the road.

Find a CPA the way you find almost everything good in this industry,  through a referral from someone already doing this work. Someone who freelances or has freelanced internationally and has already solved this problem will point you toward someone who understands gig income, gig deductions, and the lumpy, irregular way this money actually arrives. And try to find someone who isn't close to retirement. You want this relationship to grow with you for years, not have to start over and re-explain your whole history to someone new in five years.

I was lucky. Early in my career, a friend already established in this business introduced me to a CPA who deeply understood freelance work, gig income, and eventually international production. The time, money, and stress that relationship has saved me over the decades is genuinely incalculable. I think often about how different things might look if I'd spent my twenties and thirties figuring out U.S. and international tax obligations through trial and error, the way far too many people in this business still do.

Find a Financial Advisor, A Human One

This is the other relationship worth building early, for a reason specific to this industry: we don't have the traditional safety nets that other careers have.

Pensions are largely gone across most industries and were never common in ours to begin with. A 401(k) is valuable, but if you're moving between employers or freelancing for stretches of your career, those contributions can end up fragmented and modest by the time you actually need them. For a lot of people in this business, a Roth IRA and other long-term retirement vehicles aren't a nice-to-have, they truly are essential. And the earlier you start, the more time compounding has to work in your favor. The S&P 500 has averaged roughly 10 percent annually over the long run, not a guarantee for any given year, but a useful illustration of why starting at twenty-five instead of forty-five changes everything about the outcome.

I know there's a growing chorus telling people they can just manage all of this themselves with an app or with AI. And to be fair, some people in this business do actively manage their own investments and do it well. But think honestly about the life we lead. If you're on the road, on a headset, in a production meeting, or working a six-day homestand, when exactly are you watching the market? A sound human advisor isn't competing with your ability to do this yourself, they’re accounting for the reality that you are busy doing the job that pays for all of it, and you need someone paying attention when you can't.

Look for a fee-only or fee-based advisor, someone who isn't earning a commission by steering you toward specific products, and who is acting as a fiduciary on your behalf. There are good firms built for exactly this kind of relationship: ones that will work with you when you're starting out and can only invest a little, and will grow with you as your income grows and your situation gets more complex. That long-term relationship is the point. You're not looking for someone to make you rich overnight. You're looking for someone who will still be in your corner in twenty years.

Real Estate: A Strategy Worth Considering Early

Here's something I've seen work well for a number of people in this business, and something I'd encourage anyone starting out to at least explore: if your career has you living in different cities for stretches of time,  which it might, especially early on, consider buying property in those cities instead of renting, when it makes sense financially.

When you move on to the next opportunity, that property doesn't have to be sold. It can become a rental. Over a career that takes you through several cities, that can add up to several properties generating passive income,  income that keeps coming in regardless of whether you're working that week, that month, or that year. For an industry where income can be unpredictable, having a layer of passive income underneath it is enormously valuable.

This isn't for everyone, and it isn't without its own work, managing tenants, upkeep, and the logistics of owning property in a city you no longer live in are real considerations, and most people who go this route eventually use a property management company to handle the day-to-day. But as a long-term strategy for someone whose career naturally moves them around, it's one of the more powerful tools available, and it's worth understanding early rather than realizing in your forties that you sold a property in a city that has since tripled in value.

Why This Matters More in Our Business, Not Less

When you're starting out in this industry, the pay can be modest. Entry-level event and production crew work often pays in the range of a few hundred dollars a day, and it isn't always steady, there are weeks with multiple gigs and weeks with none. When you're in that phase, retirement accounts and real estate investment can feel like problems for some future version of yourself who has more time and more money.

But that's exactly why the relationships matter more here, not less. A traditional nine-to-five employee has a system around them, even an imperfect one, automatic payroll deductions, an HR department that reminds them about open enrollment, a company-sponsored retirement plan with a default contribution already set up. We don't have any of that by default. Every piece of it has to be something we build for ourselves, on top of a schedule that doesn't leave much room for sitting down and figuring it out.

That's the entire argument for getting good people in your corner early, not because you have a lot to manage yet, but because you will, and the systems are far easier to build when the stakes are small than to retrofit later when they're not.

The Advice I'd Give My Younger Self

Learn the craft. Find mentors. Say yes to opportunities, even the ones that don't pay much, especially early on. All of that advice is good and you'll hear plenty of it.

But also: find a CPA who understands gig work and international productions, and do it sooner rather than later. Find a financial advisor who will talk you through decisions, not just execute trades, and who will work with you whether you're investing a little or a lot. Think about real estate if your career moves you around. None of this is exciting. None of it will make you better at your job tomorrow.

But thirty years from now, it may be the difference between looking back on a great career and looking back on a great career that also gave you a great life.

Matt Coy is VP of Experiences at CUENTO Marketing. He consults with sports teams, leagues, federations, and major events on fan experience strategy, assessment, and implementation. He also serves as a fractional VP of Game Presentation for select clients.