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Next Up Louisville: A Free Community for Newer Real Estate Agents in Kentucky and Indiana
October 14, 2026 at 4:00 AM
by Rob Bergeron
Close-up of student answering a test in a classroom environment.

Your first three years in real estate are the hardest ones. You're learning contracts, chasing your first few clients, and trying to figure out who to ask when something goes sideways. A lot of new agents do it alone. Most of the ones who quit did it alone.

So we started Next Up Louisville. It's a free community for agents in their first three years in Kentucky or Indiana. You don't have to be at Winner Realty to join. Bring your questions, your deals and your ambition.

What you get

A monthly mastermind. Once a month we get online for about 45 minutes. I lead it. We pick a real problem (a deal that's stuck, a listing appointment, how to price, how to find your first investor client) and work it out together. No slideshow, no pitch.

A seat at our monthly discussion night. Every month Winner Realty hosts The Fon-Does and Fon-Don'ts of Real Estate with Next Title and Kentucky Private Lending. It's a real conversation about real deals, and yes, there's fondue. Next Up members get a standing invite.

A referral network. Got a buyer moving to Lexington, a seller in Southern Indiana, or a commercial deal that's outside your lane? Pass it to someone in the group you trust, and get them passed back.

Leadership roles. The first 50 members are founding members, and they get the first shot at leading a mastermind topic, hosting a meetup, or running a piece of the group. If you want to be a leader in this business, this is a place to start practicing.

People who answer. I've been doing this 13 years. Ask me anything, and if I don't know, I'll find someone who does.

Help us take Louisville's pulse

Every month we ask agents, investors and homeowners five quick questions about where the market's headed, then share the results in The Morning Bergeron. Newer agents' answers count just as much as the veterans'. Take this month's Louisville Real Estate Pulse. It takes under a minute.

Who it's for

Licensed real estate agents in Kentucky or Indiana, in their first three years. Any brokerage. Part-time is fine. Still waiting on your license to post? Reach out anyway.

What it costs

Nothing. There's no fee, and you don't have to switch brokerages to join. If you ever want to talk about Winner Realty, I'm happy to. If you don't, you're still welcome.

How to join

Grab a quick time with me at robbergeron.youcanbook.me and put "Next Up" in the notes, or email Rob@thewinnerrealty.com with your name, your brokerage and when you got licensed. You'll get the next mastermind date and the next discussion night invite.

Why we're doing this

New agents are carrying a lot right now. Fewer closings make every deal heavier, and plenty of brokerages hand new agents a login and wish them luck. I'd rather the next wave of Louisville agents be good at this, because that's better for clients and better for every agent on the other side of the deal, including us.

— Rob Bergeron, Owner–Realtor, Winner Realty

Frequently asked questions

Do I have to be a Winner Realty agent to join Next Up Louisville?

No. Next Up Louisville is open to licensed agents at any brokerage in Kentucky or Indiana who are in their first three years.

Is it really free?

Yes. There's no fee and no obligation to switch brokerages.

How often does the group meet?

There's a monthly online mastermind and a monthly in-person discussion night. You'll get the dates when you join.

I've been licensed four years. Can I still come?

Reach out. The group is built for newer agents, but if you want to help lead or mentor, we'd love to have you.

What if I'm part-time?

Part-time agents are welcome. A lot of strong agents start that way.