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What Competing in an Ironman Taught Me About Entrepreneurship


It felt like a dozen hands were pulling me under the water and I couldn’t do a thing about it. A kick knocked my goggles off and I choked on a mouthful of icy water. I was less than 200 meters from the shore and I wanted to quit. This was the start of my Ironman race. And this is exactly what it feels like to start a company.

Between starting a real estate technology company, Hightower, and completing in an Ironman, I’ve had my fair share of feeling in over my head. However, each of these adventures has taught me how to overcome an overwhelming challenge. Here are four humble pieces of advice for all of you crazy enough to do the same.

Ignore Your Fears and Just Say Yes

Starting your own company and running an Ironman race are both intimidating situations, as the outcomes are completely unknown. Despite the fear of failure that constantly was top of mind, I had to ignore my fears and take the plunge; I had to say yes.

One Thursday afternoon, a co-worker dared me to do the Ironman race. Having run several marathons, I wasn't a stranger to this kind of endurance. Even so, I was scared and nervous. But I couldn’t resist a challenge. I pulled up the website and registered for the 2012 Coeur d’Alene Ironman to a flurry of high fives. After that, there was no turning back.

It was very much the same when starting Hightower. After months of thinking and planning, I realized that nothing was going to happen unless I took the leap. I told my business partner that I was leaving my job to start a technology company and, in an instant, the wheels were irreversibly in motion.

Get a Team Together and Make a Clear Plan

Only when I left the office that night did I realize the gravity of what I’d signed up for. I had the sinking feeling that I’d just made a huge mistake. I knew that if I didn’t make a plan and build a support system for myself, I didn’t have a shot.

When you’re starting a company, there are so many unknowns—that’s why it’s important to have a plan for the things you can actually control. When I started Hightower, I realized it would be difficult to do it alone, so I joined forces with two incredible co-founders.


To those just starting on the adventure, you must master the balancing act of a long-term vision with clear near-term plans. Make your vision clear by writing it down, and set measurable 90-day goals so there’s never a question about where you’re headed next. Make your team a part of the goal-setting and lean on them to share feedback where necessary.

Plan for Bad Days and Embrace the Uncertainty

Whether you are starting a business or training for an Ironman, bad days are a regular companion. To succeed, you don’t need to be superhuman, but you do have to be stubbornly persistent. Your will becomes your strongest muscle. Make yourself a promise that when the bad day comes, you will get some sleep and get back at it the next day.

Once I left my job and started Hightower, I quickly learned that there are a thousand decisions that an entrepreneur must make without ideal experience or context. Being decisive while outside of your comfort zone is what truly sets the successful apart.


Prepare for Delayed Gratification

When building a business, every entrepreneur has that metaphorical finish line in mind. There have been countless hours and nights where I put work ahead of enjoyment with the unwavering belief that it will make the difference in getting Hightower over that finish line. And it’s worth every painful minute.


Leading up to the Ironman, I had to opt for water instead of beer, and miss trips with friends in favor of six-hour-long training sessions. I fought a constant battle between my desires for today and my goals for tomorrow. To accomplish anything of significance requires real sacrifice, which can be a lonely at times. When delaying gratification is tough, remember that you’re working towards something much more meaningful.


As you jump into starting a new business, I hope these few pieces of advice will help you along the way. Surrounding yourself with a strong team, ignoring those initial fears, making a visible plan, taking bad days in stride, and being patient will help you cross the finish line and accomplish your goals.

This article originally appeared in FastCompany.

Leasing Management

Brandon Weber
Brandon is the CEO & Founder of Hightower. Prior to founding Hightower, Brandon was a First Vice President at CBRE. He began his career in software product development.

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