Personal Development

How Horse Racing Made me a Better Real Estate Investor

27 Articles Written
Better Real Estate investor

Although I live in beautiful Chattanooga, TN I visit Kentucky and go to the horse races every chance I get.  I have been going to the Kentucky Derby for the last five years and encourage everyone to go.  If you want to meet me and get a free mint Julip – keep reading!

Want more articles like this?

Create an account today to get BiggerPocket's best blog articles delivered to your inbox

Sign up for free

The Kentucky Derby is a special event.  What other sporting event can you see homeless people walk alongside billionaires in the infield?

If you are wondering how homeless people get in, people like me buy them tickets 🙂

So how has horse racing made me a better real estate investor?

Don’t be a Fair Weather Real Estate Investor

Horse Racing isn’t a fair weather sport.  FACT: No Kentucky Derby has ever been delayed or canceled due to bad weather.  By way of reminder, the Kentucky Derby has been going on since 1875.  Be honest with yourself, how many times have you put off work because it was rainy or nasty weather outside?

You Have to Play to Win

Notice very carefully what I said.  I didn’t say you can’t bet a horse “to show” – which is where you make money if your horse comes in first, second or third.

What I want you to takeaway is if you want to sit on the sidelines and complain about not being able to get a loan, or lack of inventory, or too many competitors then go ahead. But I'm actually going to be in the game. Getting financing no matter what the financing environment. I'm going to be buying or building multifamiliy properties in my defined area, because thats what I do.

Related: How To Beat The Competition and Get Better Deals

I’ve never met anyone successful that just sits around and complains.  This leads me to my next point:

Follow Your Plan, Not Someone Else’s

There was one Kentucky Derby where I made a fair amount of money.  I got really excited and for the next year bought this guy’s tip-sheet.  He had all of these sophisticated betting strategies.  I didn’t understand what I was doing,

BUT this guy had an amazing track-record.  To be honest, I had trouble communicating at the betting counter exactly what type of bet I was putting on.  I lost more money that Kentucky Derby than I care to admit.

In hindsight of-course it was stupid.  Now, I have a plan, and I work my plan, exactly like my real estate investing.

Planning Is Critical

Trainer’s jobs are to put the horse in the right race against the right competition and have a plan for two or three more races depending on how the next race unfolds.  You should have a plan for your real estate investing that is adaptable to changing conditions, results and competition.  You should also be willing to make those changes quickly.

Location is Everything

At the Kentucky Derby there are two types of spectators: those in the infield and everyone else.  I love the infield.  You have everyone from retired people to partying college kids. Importantly, most people don’t go because they are scared of the chaos that usually ensues in the infield.  There are about 80,000 people in the infield and… let’s just say it’s an “interesting crowd.”

Why am I bringing this up?  Because most people don’t go because they are too proud to be in the infield, or too intimidated.  Like real estate, you need to come see it for yourself.

Related: Long Term Real Estate Investing is like Pitching: Timing and Location Quality Rule


This year I’m going to be at the Kentucky Oaks on Friday and the Kentucky Derby on Saturday.  If you would like to meet up with me and my best friend hit me up in the comments.  You might even get a complimentary mint julip!

    Replied over 6 years ago
    Jimmy Thank you for the article. To be fair I looked it up because of the horse racing reference. I cannot recall my first time on a horse, the earliest horse injury I can recall was around age 4. I jockeyed horses when I was young and a few times myself, my dad and my brother all rode in the same race. My father jockeyed and trained from before I was born and is still training to this day and he is dam close to 80. Horses keep him broke but happy. Real estate is important because doing some of that is what enabled my father to keep doing race horses. It is normally a rich man’s sport as you cannot count on making a living by having winning horses. The relationship between horses and real estate investing have similarities except you rarely lose if you work hard at real estate investing. It can happen, but the odds are very much in your favor. You need knowledge, but that is very much available. It helps though if you love what you are doing. Then making money is a bonus. In the back of my mind has been an idea to do something nice for my dad and it dawned on me that maybe taking him in person to see the Kentucky Derby may be it. Every year I have been around him during The Derby he goes to a TV and we watch it, if there is a telecast parimutual betting he bets on it. It is a tradition. Thanks for the Idea.
    Replied over 6 years ago
    Great story Jerry! Thanks for sharing.
    Michael Siekerka
    Replied over 6 years ago
    Great post Jimmy! Looking forward to meeting you this time around and hope you guys enjoy the stay! -Michael
    Replied over 6 years ago
    Replied over 6 years ago
    Interesting analogies. Not a big horse racing fan but these are great points and easy to understand even for the causal fan.
    Replied over 6 years ago
    Love the analogy! If I was in Kentucky, I’d definitely have to join you! And Jerry, I enjoyed your story as well. I’ve been involved with horses most of my life and my current riding horse is an ex-racehorse. Reply Report comment
    Replied over 6 years ago
    Love the analogy! If I was in Kentucky, I’d definitely have to join you! And Jerry, I enjoyed your story as well. I’ve been involved with horses most of my life and my current riding horse is an ex-racehorse.
    Jacob Gish from Chattanooga, Tennessee
    Replied over 5 years ago
    Great article!! I live in Chattanooga myself and my grandparents still live in Lousiville. Your description of the crowd was tactful and accurate.