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It was 5:15 AM on an August Sunday morning in Louisville, KY, the day and location of my Ironman race – a 2.4 mile swim, 112 mile bike, and 26.2 mile run. After arranging my gear, giving everything a once-over, and having my arms and legs marked with my race number, I stepped in line in what was already a half mile long line of racers looking to get a close spot to the starting line when the gun went off. Though I didn’t realize it at the moment, so much of what I’d learned in this journey, and the race itself, carried specific applications to being successful in the business world.

After taking a seat in the grass, a man dressed in a black version of the same 1-piece swim-suit I had (mine was blue) stood next to me. I saw on his ankle he had the “M-Dot” tattoo, a symbol of having completed an Ironman, inked on his ankle. Interested in each other’s background, we engaged in conversation.

“Ever done an Ironman before?” he asked.

“Nope,” I replied.

“Great! A newbie… you’ll be just fine. What’s the last half you did?”

I assumed that half meant a ‘half-ironman’ and replied “Never done one of those either.” He looked confused.

“So you’re going straight from the Olympic distance (which is about 1/5 of the total distance)? That’s pretty risky.”

“Actually, I’ve never done any triathlon. This is my first. Any last minute advice?”

He smirked, was not sure what to say, and finally said “Well… Best of luck.”


That was the end of that conversation. At least I learned something, unfortunately a bit late. Apparently it isn’t a good idea to have an Ironman be your first triathlon. Nonetheless, looking back at that conversation, I am glad my friend didn’t probe further. It wasn’t the only unconventional route I took in this endeavor. My route was a compilation of concepts I hold to be true in all aspects of life.

So what was it that, if that man next to me in line had known, would have perhaps led him to not have been so quick to judge my lack of ability? Here are five take-aways I took from the event and direct applications to my entrepreneurial philosophies:

1. Have unrelenting confidence in yourself. Always tell yourself “Yes I can.” If someone tells you otherwise, ignore it. I am sure people told me along the way this was a bad idea… I don’t recall specifically though- that talk always goes in and out of my ears. This DOES NOT mean you can do everything in life at will. It does mean when you have a vision you believe in and you have a nervous excitement toward the concept of pursuing it, your instincts are not lying to you. So much of this hit home with starting my first company.



2. Don’t follow conventional wisdom. Conventional plans and roadmaps were made by someone else and for someone else – not for you. Further, you can’t accomplish more than someone else by following the same plan someone else did. Read others’ plans, learn, and find out who wrote it and who it was intended for. Find holes in the plan. Find ways to improve it. Look inside at who you are. Then, come up with something original – maybe it will fail, but that’s ok.

3. Have an EXACT vision of what you want to do on the day you want to do it. I want to swim, bike, run this distance, in this time, on this date. The more precise, the better as you know what to expect. Think about this in business terms, and things get a little more clear.



4. Learn to Sleep Faster. Sleep 6 hours, not 8. If you have to sleep 8, learn to sleep faster. There aren’t enough hours in the day for all the things we want to do. However, by using time efficiently we can all move forward with things we want to accomplish. Every practice session I held for this event began before 5 AM or after 8 PM. The more I had to do, the faster I slept.

5. Pretend it’s easy. This is an important trait many overlook. I never liked and always tried to avoid talking about how much work I may be putting in to pursuing a goal. I find it never enhances social interactions and never promotes a humble spirit. Thus, I keep it to myself unless asked – and I believe this is a key in having a humble spirit. Be cool on the outside and have a fire on the inside.

Are there more than 5 traits? Yea, there always are. Everyone has come up with certain rules. However, these are five I truly believe in and concepts that directly carried over across different areas of my life – whether joining a new organization, venturing into entrepreneurship, or completing a race.


Written by Jeff Reekers, director of marketing at Datahug, a relationship sales SaaS platform based out of Dublin, Ireland.

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