How Horse Racing Made me a Better Real Estate Investor

How Horse Racing Made me a Better Real Estate Investor

2 min read
Jimmy Moncrief Read More

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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!

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!