Search
Leave a Message
Thank you for your message. We will be in touch with you shortly.
Explore Our Properties

What Tony Hawk Taught Me About Being a Real Estate Agent

Tyler Henson  |  October 6, 2026

Tony Hawk speaking at the real estate conference

I just got back from a real estate conference with Ryan Serhant. One of the speakers was Tony Hawk, and what struck me most was the way he talked about attempts that didn’t work.

He seemed to accept them as part of learning a trick. You try it, see what happens, make an adjustment and try again. That’s how you figure it out. An unsuccessful attempt didn’t seem to shake him the way it might shake someone who expected to get it right.

When he described finally landing the 900 at the 1999 X Games, he’d been trying to get that trick right for about ten years. That night, he had consistent speed and spin, but he kept falling forward.

He shifted more weight toward his back foot while he was in the air. This time he fell backward, and that was the moment he knew he could do it. He understood the adjustment he needed. On the next attempt, he landed it.

I kept thinking about how differently you approach the next attempt when you expect that learning will take a few that don’t work.

The no that stayed with me

Being a real estate agent involves more rejection and unsuccessful attempts than most people probably see. You put yourself out there, and plenty of times the answer is no. You have to keep doing the work long enough to get the yes.

One of those no’s hit me especially hard when we were growing our business, before the post-COVID housing frenzy. We reached out to a seller whose home had come off the market without selling, even in a strong market. It was over $1 million.

He asked me, “Why would I hire you if you’ve never sold in this price point?”

I knew I had the ability. I just hadn’t had the opportunity.

It felt like I’d failed before I could even try. I needed someone to give me a chance to do the work, and that conversation wasn’t going to be it.

A relationship became the opportunity

Our first listing over $1 million eventually came from clients we’d helped purchase a river house. We’d built a relationship with them, and when it was time to sell their home in Brentwood, they didn’t want to trust anyone else with it.

They gave us that opportunity. When we sold the home, it was the first sale over $1 million in their neighborhood.

I think about that when I remember the earlier rejection. The relationship we’d built became the chance to prove what I knew we could do. I had to keep going to get there.

What that means when we sell a home

That same willingness to keep going matters once we have a listing.

We may hear countless no’s before we find the right buyer. I keep paying attention to the response, making adjustments where they’re needed and working toward the person who sees that home as the right fit.

Some feedback helps us understand what needs to change. Sometimes a buyer simply wants something different. We have to use our judgment, stay engaged and keep working through it.

Ryan talked about being willing to work through failure until you succeed. Tony’s story helped me think about what that means in practice. If unsuccessful attempts are part of how you learn, you can approach the next one with something useful from the last.

That’s the thought I brought home. It applies to building a business or learning a new skill just as much as it does to real estate. You have to be willing to try before you know how it’s going to turn out.

Follow Us On Instagram