Your career has a clock. Your money doesn't have to.

Whether it's NIL money (that stands for Name, Image and Likeness, the money college athletes earn from their own name and brand), a revenue-share check from your school, a rookie contract, a tour, a big purse at the track, or a brand deal, the money usually shows up fast and doesn't last forever. Winner Sports & Entertainment is the part of Winner Realty that helps athletes, musicians, horse racing pros and creators turn that money into property that keeps paying them long after the paycheck stops.

We're not here to sell you the biggest house on the block. We're here to make sure you still own something when the cheering stops.

Start your private plan or text Rob at (502) 305-8915.

Who we work with

We like working with people who are just getting their first real money and want to be smart with it. You don't need to be famous. You need to be serious about not blowing it.

• College athletes earning NIL and revenue-share money, and their parents. Read our college athlete guide to NIL money and real estate.
• Pro athletes who play here, grew up here, or come home in the off-season.
• Jockeys, trainers, exercise riders and owners in the horse racing world. Read our guide for horse racing professionals.
• Musicians, touring artists and festival talent. Read our guide for musicians and touring artists.
• Creators, streamers and coaches with big but uneven income.

Why this matters

Big money does not protect people from going broke. A study by the National Bureau of Economic Research looked at NFL players and found that about 1 in 6 filed for bankruptcy within 12 years of retiring. Players with longer, better-paid careers were not any safer. The problem usually isn't how much they made. It's that the money came in a short burst and nothing was set up to keep producing income after it stopped.

That's exactly what real estate is good at. A paid-off rental, a duplex you live in while the other side pays your mortgage, a small commercial building with long-term tenants. These keep paying you whether you're playing, touring, injured or retired.

And the money is real now. Schools can pay athletes directly, with a revenue-share cap of more than $21 million per school this season, and outside NIL deals come on top of that. More young people than ever are getting a big check before they've ever bought a house. We want to be the people they call first.

What we actually do

1. Build your plan first

Before you buy anything, we map out what you earn, what you need to set aside for taxes, and how much can actually go to work in real estate. You'll meet with a CPA (certified public accountant) from our network who works with real estate investors. Use the NIL Money Planner below to get a rough starting number.

2. Find the right property

Your first home, a duplex you live in while renting the other side (people call that "house hacking"), a rental for your family to live in, or commercial property for long-term income. Any property with two or more units counts as commercial, and our Winner Commercial team handles it.

3. Plug you into the team

Lender, CPA, attorney, insurance agent, title company, inspector, contractors and property management. These are the same people we use on our own deals, not names out of a phone book.

4. Run it while you play

You're on the road, in camp, at the track or on tour. We handle showings by video, inspections, contractors and closings, and we keep you updated by text and email. You sign electronically or with a mobile notary.

5. Keep it private

We can buy through your LLC (limited liability company), keep your name out of our marketing, and sign an NDA (non-disclosure agreement) on day one.

NIL Money Planner

[[WR-NIL-PLANNER]]

Why people trust Winner Realty with their money

Rob Bergeron has been in real estate for 13 years and has been part of more than 2,000 residential and commercial transactions since 2013. Other licensed agents hire him for their own deals, which is why people call him "the realtor's realtor." He served three elected terms on the board of Louisville's local real estate investors association.

We already do this every day for investors who live in California, Texas and overseas and buy here without ever visiting. We handle the time zones, the wire transfers, the LLCs, the banks and the contractors. We've walked investors through BRRRR deals (buy, rehab, rent, refinance, repeat) and helped them grow from one rental to many. An athlete on the road or a musician on tour needs the exact same setup.

Winner Realty is licensed in Kentucky and Indiana. Kentucky's state income tax dropped to a flat 3.5% on January 1, 2026, and lawmakers are working to keep lowering it, which makes this a good place to put down roots and own property.

We also give 1% of our net profits to Hand in Hand Ministries, which builds homes for families who need them. If you want your money to do some good too, ask us about joining a build. You can read more on our Hand in Hand page.

What we won't do

• We don't negotiate your NIL deals. That's your registered agent's or attorney's job.
• We don't give tax, legal or investment advice. Our CPA and your own advisors do that. We help you plan the real estate side and bring everyone to the same table.
• We don't give athletes special deals or pay for shout-outs under the table. Everyone gets the same Winner terms. Anything promotional is a written agreement that you report the way your school requires.
• We don't pool your money with other people's money. You own your property directly, in your name or your own LLC.
• We don't use team names or logos to sell you anything.

Where to start

• Your First Big Check: a 90-day plan
• NIL money and real estate for college athletes
• Real estate for horse racing professionals
• Real estate for musicians and touring artists
• House hacking in Louisville
• How to get pre-approved for a mortgage in Kentucky
• Investment property analyzer

Frequently asked questions

Can a college athlete buy a house with NIL money?

Yes, if you're 18 or older. Lenders look at how steady your income is, so NIL and revenue-share money usually needs some track record or a bigger down payment. We'll connect you with a lender who has done it before.

Will buying property affect my eligibility?

Buying a home with your own money doesn't. What matters is where the money came from and whether anyone gave you something in exchange for your name. We keep everything on standard terms, and you should check with your school's compliance office before signing any promotional deal.

How much of my money should go to taxes?

It depends, which is why you'll talk to a CPA first. NIL and brand money is usually self-employment income, so federal income tax, self-employment tax and Kentucky's 3.5% can add up fast. Set money aside before you spend any of it. The planner on this page gives you a rough idea.

Can I buy a house for my parents?

Yes. You can buy it in your name or your LLC's name, co-own it, or help with a down payment. Each way has different tax and loan rules, so we map it out with you and the CPA first.

I'm on the road most of the year. Can I still invest?

That's who we built this for. We handle showings by video, inspections, contractors and closing paperwork, and you sign electronically or with a mobile notary.

Do you only work in Louisville?

We cover Louisville, Lexington, the rest of Kentucky and Southern Indiana. If you're buying somewhere else, we can refer you to a trusted agent there.

Start privately

Tell us a little about where you are. Nothing is shared, and we'll reach out by text or email unless you ask us to call. Start your private plan, text (502) 305-8915, or email rob@thewinnerrealty.com.

Winner Realty provides real estate services only. Nothing on this page is tax, legal or investment advice. Talk to your CPA, attorney and financial advisor before making decisions. Equal Housing Opportunity.