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Today's track: Dermot (See Yourself In My Eyes) — Fred again..
I've been taking a lot of meetings lately. A lot.
And the people sitting across from me have been strange in the best way. Curious. Intelligent. They can feel the world changing. AI, rates, prices, all of it moving in a direction nobody can fully map yet. And it's got them looking at their own lives with fresh eyes.
Am I happy with the way I'm living?
Is my time going where I want it to go?
Am I being deliberate with it? Am I protecting it?
Because I think we all know this, even if we don't say it out loud. Running around with your hair on fire is not life. It's not living.
And this industry loves hair on fire. Everything is urgent. Every text needs an answer in four seconds. Every deal is a five-alarm emergency. And if you're not frazzled, somebody's going to assume you're not working.
I just don't have that in my life.
I have balance. I have time to be bored, which is underrated. Time to create. Time to work. Time to work out and focus on wellness. Time to reflect, and to call my friends and family and actually check in on them. Walks with the dogs. The hammock. Fires out back. I have time for all of it because I protect my time like it's money, and because I have great systems.
Who's been reaching out
Most of the people asking for these meetings have been in the game more than a decade. And it's not just realtors. Mortgage lenders. Insurance agents. Title attorneys. Investors. Wholesalers. Good people who've been grinding a long time.
They're tired. Inflation, rates, a slower market, the commission lawsuit fallout. It all piled up. And the line I keep hearing, almost word for word, is "I need to change something."
If that's you, you're not imagining it. Here's what the numbers say.
The National Association of Realtors, or NAR (the national trade group most agents belong to), had 1,438,569 members as of late June. At the 2022 peak it was close to 1.6 million. That's roughly 160,000 people gone in about four years.
NAR's 2026 Member Profile, their yearly survey of members, says the typical member now has 13 years of experience, up from 12 the year before. When the experience number keeps climbing while the headcount drops, it tells you who's staying. The veterans. And the veterans are exactly who's been sitting across from me saying they're worn out. They see what I’m doing, they see the value, and they want in on the time freedom.
That same survey says the typical agent closed nine transaction sides in 2025. (A "side" is representing either the buyer or the seller in a sale.) And they worked a median of 35 hours a week to do it.
Hold onto that nine. We'll come back to it.
"Rob, how do you do it all?"
That's the question I get in every single one of these meetings.
How do you read all those books every year? How do you write songs, and short stories, and a newsletter every morning? Where do the ideas come from? How are you still selling this much real estate?
Because I'm still a practicing agent. I'm still top 1% in sales, and the last time I looked up the stat, I qualified for top 1% in the country. Then there's Winner Realty, Property Partner Data Company, and OffMarket.deals on top of it.
Remember that nine? That's the typical agent's whole year. I close quite a bit more and it's not because I'm working more hours than everybody else.
So how?
Honest answer: I have a lot of time. It doesn't hurt that I'm single and it's just me and the dogs. That's all manageable.
But the real answer is people. Who, not how.
The people I work with are just incredible. And they're empowered. They don't need me hovering over them, and that's on purpose. David Padron and I actually bought the website What Not Who, for the AI world, a few years ago. Can't wait to write that book!
The people I work with are just incredible. And they're empowered. They don't need me hovering over them, and that's on purpose. David Padron and I actually bought the website What, not who. For the AI world a few years ago, can’t wait to write that book!
Practice like Cignetti
At Winner Realty, we run things a lot like Curt Cignetti runs Indiana football practice. Go look it up. It's wild.
Before Cignetti got to Bloomington, Indiana had the most all-time losses of any program in major college football. They went 3-9 the year before he showed up. My buddy Nick Peskoe stuck with them through it all.
Then it was 11-2 and a playoff spot in his first season. Then a perfect 16-0 in his second, capped with Indiana's first national championship ever, 27-21 over Miami on January 19, 2026. That's 27-2 in two years, at the school everybody used to laugh at.
And here's the part everybody wants to know. His practices are short.
Really short. Even his hardest sessions come in well under two hours. A full practice, stretching and walkthrough included, can run about 90 minutes. Nobody stands around. One drill ends and they're already jogging to the next one. He's said he's never used all 20 hours a week the NCAA (the governing body for college sports) allows. Never used all 25 fall camp practice days. His first spring at Indiana, he scheduled 13 of the 15 practices allowed and said he was fine with it.
And during practice, he watches from his own spot so he can see the whole field, and he lets his coordinators handle the detail work. That's Who Not How on a football field.
Less time on the field didn't make that team soft. It made them crisp. Fresh legs, healthy bodies, every minute counts.
That's what we're going for. You don't have to stress yourself out just to prove you're working. You don't have to be miserable because you think everybody else is miserable and that must be what hard work looks like. Organized, focused, done. Then go live your life.
It's why our agents get fresh residential and commercial leads in their inbox every morning at 6:30. Nobody at Winner Realty starts their day hunting.
Also, would love to give a shout out to Coach Will Stein at Kentucky. He is the Youthful Alliance version of Coach Cignetti.
Speaking of coaches and winning. If you're a college athlete, a pro, a musician, or anybody in the horse racing world who just came into real money, we built a whole corner of the Winner Realty site for you: Winner Sports & Entertainment. NIL (name, image and likeness) money is real now, and a first big check deserves a plan before it deserves a new truck.
Start with the college athlete guide to NIL money and real estate and Your First Big Check: a 90-day plan. There's a guide for horse racing professionals and a guide for musicians and touring artists too. And the free tools that go with it, no email wall: the NIL Money Planner, How Much House Can I Afford, the investment property analyzer, the DSCR loan calculator (DSCR stands for debt service coverage ratio, a rental loan that qualifies on the rent instead of your paycheck), the capital gains and 1031 exchange estimator, and the house hacking calculator. When you're ready, start a private plan and we'll keep it between us.
"You're the janitor of your business"
One of my smartest friends is the guy I lean on when I'm navigating something difficult, or when an exciting opportunity shows up and I want to make sure I'm doing things the right way. Prudently.
He built himself a Jarvis.
If you haven't seen the Iron Man movies, Jarvis is Tony Stark's AI (artificial intelligence) assistant. It's the voice in the suit that runs his house, knows everything about him, and answers anything he asks. The name stands for "Just A Rather Very Intelligent System." Fun fact: in the original comics, Jarvis wasn't a computer at all. He was Edwin Jarvis, the Avengers' human butler.
My friend made that real. He indexed his whole life into it. Every conversation, every document, everything. So it knows him, and he can consult it anytime he wants. He's very smart, the guy who built this. Friends like this are the kind of people I surround myself with, people who make me strain and aspire for more in life!
He's also super wealthy. Owns tons of units across all kinds of property classes. Great family. Great life. By any scoreboard, he's Winning and Winning Big!
So once it was done learning, he asked it: "After everything you've learned about me, give me some insights on my business."
And it said: "You're the janitor of your business."
Based on the questions he asks and the things he spends his days doing, he's working in the business, not on the business.
He laughed telling me. He said it made him feel bad. But it made him reflect. And now he's streamlining. He's selling the stuff that doesn't fit what he wants his life to look like and moving into things that are more manageable.
That "in it versus on it" idea comes from Michael Gerber's book The E-Myth, and it's been around since the '80s. The tools are new. The trap isn't.
The quiet wave: senior investors handing off the keys
He's not the only one. A lot of senior investors have been reaching out to me lately. They're getting older. Their kids don't really want to manage these properties. And they're tired too.
The question is always some version of: "What can I roll this into that's easier to manage now, and easier to hand off later in life?" Oil and gas. Industrial. Something with fewer toilets and fewer 2 a.m. phone calls.
You don't have to sell your rentals one at a time. Bundle a handful of houses together and they can sell as a package, a commercial deal, to one buyer at one closing. Hedge funds are buying again, and I'm working with one right now. If you need to unload anything under $85,000, email me the addresses and bed/bath counts. One closing instead of five, and a clean way to free up money for a 1031 into something you'd rather own.
It's not just Louisville. A big landlord survey out of the United Kingdom this month, from Property118, found that 72.8% of landlords age 65 to 74 expect to sell some or all of their portfolio in the next three years. Almost 6 in 10 of them said their own age, retirement or health is part of the reason. Different country, same conversation I'm having over coffee here.
This is where the 1031 exchange becomes your best friend. And its cousin, the reverse 1031. Also, those handy letters of intent, or LOIs (a short one-page offer that starts the conversation before anybody writes a full contract), that create incredible opportunities with tired landlords like these folks!
A 1031 exchange, explained like you're five
Section 1031 is a part of the federal tax code, the rules the IRS (Internal Revenue Service) runs on. Normally, when you sell an investment property for a profit, you pay capital gains tax, which is the tax on that profit, plus tax on the depreciation you wrote off over the years.
A 1031 exchange lets you skip paying that tax right now, as long as you roll the money into another investment property. You're not dodging the tax forever. You're deferring it, pushing it down the road.
The rules, in plain English:
Like-kind. It has to be real estate held for investment or business, traded for other real estate held for investment or business. And "like-kind" is broader than people think. A fourplex for a warehouse can work. Rentals for land can work. Your own home doesn't count.
A middleman holds the money. A Qualified Intermediary, or QI, is a neutral third party who holds your sale money so you never touch it. If that cash lands in your account, the exchange is blown.
45 days to pick. From the day you sell, you have 45 days to name, in writing, what you might buy.
180 days to close. You have to close on the new property within 180 days of selling the old one (or by your tax filing deadline, if that comes first).
The reverse 1031: buy first, sell second
The regular 1031 has a stressful part. You sell, the clock starts, and now you've got 45 days to find something good. In a tight market, that's how people overpay.
A reverse 1031 flips it. You buy the new property first, then sell the old one.
You can't own both at once inside the exchange, so a special company called an Exchange Accommodation Titleholder, or EAT, "parks" one of the properties by holding the title for a while. From the day it takes title, you have 45 days to name which property you're selling, and 180 days to finish the whole thing.
It costs more. The extra paperwork and parking fees often run $5,000 to $10,000 or more on top of a regular exchange, and you need the cash or financing to buy before you sell. But for a senior investor who's ready to move and doesn't want to get squeezed by a 45-day deadline, it can be the difference between a calm handoff and a panic buy.
Where the tired money is going
When people want something easier to hold and easier to hand down, here's where the conversation usually goes:
Triple net leases, or NNN. One tenant, think a pharmacy, an auto parts store, or a warehouse user, pays the rent plus the property taxes, insurance and maintenance. You mostly collect a check. Here's our triple net lease guide for 1031 buyers.
Delaware Statutory Trusts, or DSTs. You own a slice of a big, professionally managed property, like apartments, industrial or medical office. Fully passive, and they can take 1031 money. The trade-off is you give up control, and getting out early can be hard.
Industrial. Warehouses and flex space. Fewer tenants, fewer toilets, longer leases. Start with Louisville industrial and warehouse investment properties and Louisville's industrial corridors (I-65, the airport, Jeffersontown).
Oil and gas. Certain mineral and royalty interests can count as real estate for a 1031. This one is very case-by-case, so it's a conversation for your CPA (certified public accountant) and your QI before anything else. We wrote it up here: 1031 into oil and gas royalties and mineral rights.
And one more thing every senior investor should ask their CPA about. Under current law, when heirs inherit a property, they generally get what's called a "stepped-up basis." In plain English, the property's tax starting point resets to what it's worth when they inherit it, which can wipe out the gain you kept deferring. That's why you hear old-timers say "swap till you drop." Laws change, so get your own advice on that one.
I'm a realtor, not your CPA or attorney. But I've sat at a lot of these closing tables, and I know exactly who to bring in. If you're thinking about trading in some headaches, Louisville has the inventory to work with. The lists are in the PS.
Want to go deeper? We built a whole 1031 library on the Winner Realty site. Free, no email wall.
Learn it:
Cost segregation for commercial real estate, a way to speed up the depreciation on the building you trade into
Selling an inherited house in Kentucky, for the heirs on the other side of that stepped-up basis
Run your numbers:
1031 exchange deadline calculator. Put in your sale date and it gives you your 45-day and 180-day deadlines.
Capital gains and 1031 exchange estimator. See what you'd owe if you sold outright versus exchanged.
Get help: if the clock is already ticking, read up against a 1031 deadline in Kentucky? and see how our 1031 buyer's agents find replacement property fast. Or just text or email me.
The altar call
To be honest, I wasn't totally sure where I wanted this one to land when I sat down. But I think it's this.
Consider this an altar call. For realtors. Wholesalers. Investors. Insurance agents. Mortgage lenders. Title attorneys. Anybody in this business who's been running with their hair on fire so long they forgot what it feels like to be bored on a Tuesday afternoon.
If you just want a little bit of balance in your life, hit me up.
I want to get you your time back. I want to pour into you, give you great systems, and help you build something that runs without you sweeping the floors every night. Then I want you to go spread the good news that it can be done, and send the next tired person my way. I want everybody coming to me for this help.
Because I really do feel fulfilled serving this way. I love pouring into my agents. I love seeing them successful, giving them opportunities and leads, creating new things and telling them about it, and watching them get happy and excited about this business again.
And then there's the giving. Winner Realty gives 1% of its net profits to Hand in Hand Ministries. I've been on three build trips in person, and I've been a part of five builds total. Everybody here loves it. We love giving back. It just feels good, and it's baked into our DNA.
So here's how to take me up on it. If you're an agent, grab a time on my calendar. I love talking with agents. Everybody else, hit reply or text or email me and tell me the one thing that's eating your week. I read every one.
Free tools for Louisville buyers, sellers and investors, no sign-up and no email wall: the investment property analyzer, the BRRRR calculator, the Kentucky seller and buyer closing cost calculators, and a lot more on the tools page.
Know somebody who'd like this in their inbox every morning? Send them your personal link. One friend signs up and you get my daily Top Five. Three friends and you get Insider Access.
📊 Friday's poll: What's the scariest thing on your real estate plate right now? Here's what Louisville said, plus the first step and the right pro for each.
A property that won't sell, 44%. First step: figure out if it's price, condition or exposure. Right pro: an agent who can put it in front of more than the MLS (the Multiple Listing Service). That's what OffMarket.deals and its 70,000+ buyers are for.
A partner, co-owner or family mess, 22%. First step: get everybody's goals on paper before anyone talks price. Right pro: a real estate attorney, and sometimes a mediator.
Taxes or financing, 22%. First step: know your numbers. What you paid, what you owe, what you've depreciated. Right pro: a CPA who does real estate and a lender who does investor loans. If it's a sale with a big gain, scroll back up to the 1031 part.
Nothing, I'm fearless, 11%. Love that. Go write an offer.
Today's poll. Be honest. Next issue I'll share what Louisville said, plus the one system that gives back the most time for each answer.
Be honest: where does most of your week actually go?
🏆 Want this morning's Top Five? Every day I screen the whole Louisville MLS for the five best deals and the five most ripe for a lowball, with the number I'd offer. I can't blast other agents' listings to a list, but I can send them to you. Reply "FIVE."
With time to spare,
Rob Bergeron
Owner–Realtor at Award-Winning Winner Realty
Winner Realty: (502) 305-8915
Winner Realty | OffMarket.deals | Property Partner Data Company
Schedule time to discuss your goals, bottlenecks, or whatever's on your mind — book me here.
PS: The trade-in-your-headaches shopping list. Every one of these is clickable, so go be curious.
Industrial and flex buildings, the easy-to-manage 1031 trade. Fewer tenants, fewer toilets, longer leases. If you're thinking about a 1031 out of a pile of smaller rentals and into one easier building, start with these three:
72 industrial buildings for sale in Jefferson County on KCREA (the Kentucky Commercial Real Estate Alliance, our state's commercial listing exchange). On the search page, set Type to Sale, Use to Industrial, and Where to Jefferson.
Some buildings show up on more than one site. Find one you like and text or email me. I'll pull the numbers and tell you whether it works as a 1031 replacement.
43 commercial buildings with five or more units for sale in Jefferson County, from a $259,000 six-unit up to a 48-unit at $4 million. More doors under one roof, one management company, one set of books. That's the classic 1031 move: trade the scattered rentals for one building.
63 commercial properties where the seller has already cut the price, two units and up in Jefferson County, from a $35,000 duplex to a $1,075,000 fourplex. A few of them have come down six figures from where they started. A seller who's already blinked once reads your offer differently.
And if you're on the buying side: 65 houses with four or more bedrooms listed under $200,000 in Jefferson County, from $53,000 up to just under $200,000. More bedrooms at a lower price is where rental numbers tend to work, whether you hold it as a long-term rental or fix it and flip it. Find one you like and text or email me.
PSS: All currently available Winner Realty offerings, in one spot: all 16 active Winner Realty listings on the MLS, plus everything on OffMarket.deals.
PSSS: Got rentals under $85,000 you're tired of managing? I've got a hedge fund buying right now in high volume.
PSSSS: Newer agents, this one's for you. Next Up is my free monthly online session for agents in their first three years, any state, any brokerage. It's the first Friday of every month, 10:30 to 11:30 a.m. Eastern on Google Meet, and the next one is this Friday, November 6. One topic, taught plainly, no pitch. Text (502) 305-8915 or email [email protected] with your name, state and years licensed, and I'll send you the link. All the details are on the Next Up page.