3 Business Lessons We Learned From this Olympian Equestrian


Happy Monday, partner. This is The Oxer by Pegasus. The newsletter that takes you out of your tack room and into the global equestrian industry.

In today’s edition, we’re writing about the most important takeaways we learned talking to Jill Henneberg on the The Pegasus Podcast.

Jill is the youngest athlete to ever represent U.S. Eventing in Olympic history.

She did this as a 21-year-old in the 1996 Atlanta Games.

After that, she still garnered two decades of experience as a highly sought-after trainer and is now having a successful career as a real estate agent in Ocala, Florida—home of the World Equestrian Center.

Jill has a pulse of what’s going on in our industry and of what it takes to, well, literally be an Olympic equestrian athlete.

The Oxer by Pegasus is supposed to be a place where you learn each time you read it, henceforth we have this edition.

Keep reading to learn something new, and if you want to listen to the whole podcast episode, you can do so on Spotify, Apple, or wherever you listen to your podcasts.

You Have to Really Want Something in Life in Order to Achieve It

While this might sound like cliche advice, it’s really not.

Jill mentioned on the show that she had a student who appeared as if she wanted to level up her riding skills.

Jill, being an extremely experienced rider, felt after all that they had been through that this person did not want it as bad as they said.

Because if they wanted to level up so badly, wouldn’t have they worked harder to get better?

She also mentioned that hard work beats talent, every time.

But what needs to be understood is that hard work doesn’t come out of nowhere; it usually comes from a place of extreme yearning for something that you want.

Do you really want to be a better rider?

Do you really want to be in the next Olympics?

Figure that out before getting to the grindstone, because when you’re there, you have a long way to go.

Why Does Nike Not Have an Equestrian Line?

It’s quite a peculiar question if you think of it.

Not because it’s a stupid question, but because it even is a question.

If you’ve ever gone to a Nike Store or a Dick’s Sporting Goods, you’ll see apparel for pretty much every sport that’s popular in America except for horse sports. You still have to go to tack stores or to equestrian-specific brands to get apparel.


Walk into any major city in or out of America, and you’ll see many wearing a Yankees hat, a Lionel Messi jersey, or a Golden State Warriors shirt—much of the time sported by those who aren’t even fans of the sport.

That’s the point that we’ve discussed with Jill: equestrian can reach the masses if it was adopted by a mass market sports apparel brand.

But the problem is that the majority of equestrian athletes who are growing their presence online aren’t making deals with these brands.

We don’t have info on whether or not they’re reaching out to major brands like Nike or Under Armour, but the fact that we don’t have anything for such an old group of sports might suggest a lack of effort.

Additionally, Jill touched on the fact that many athletes say they get sponsored, yet in reality only get ten percent off of a saddle for shouting out the company on Instagram.

This isn’t to discount those who do get big sponsorship deals as much as it is to point out that exchanging an Instagram post for tack at a lower cost isn’t a sponsorship in reality.

Jill says that we should think and go bigger in order to grow bigger as an industry.

Knock on the doors of Nike in Beaverton, Oregon and get paid instead of getting discounts on tack. The folks at Nike probably won’t ignore you if you bring your mare with you.

The Ocala Equestrian Boom Isn’t Ending Anytime Soon

Despite being a native of New Jersey, Jill has been coming down to Ocala to ride just about every winter. She is no stranger to the area.

On the podcast, she told us that the Ocala she knew twenty years ago compared to what’s there today is a completely different planet.

It was unique to hear her perspective as she is someone who’s seen Ocala for many years—as a rider—before coming down full-time as a real estate agent.

And as a real estate agent, she meets people coming to the area all the time and learns about their purpose for contemplating buying property in the area.

According to her, not everyone is coming to Ocala for equestrian. As equestrian is the reason why it’s developing, there’s more that’s coming to Ocala such as concerts and a much upgraded downtown.


Simultaneously, the surrounding area of Ocala comprises both natural reserve and farmland preservation area, keeping the vibe pure and untouched.

Ocala is showing the world that you can have your cake and eat it, too: be environmentally friendly while being a boomtown for sports and culture.

The coolest part is that it’s us equestrians who are teaching that lesson, as Ocala’s growth is thanks to it being one of the horse hubs of the world.

All the more reason to invest in tenfolding the fandom of horse sports.

We had fun talking to Jill and reflecting on these lessons, so thanks for sparking the inspiration to pass on to others.

If you want to listen to the full episode, find it on Apple, Spotify, or wherever you listen to your podcast.

Go for gold,

The Oxer by Pegasus

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