Riding shotgun with the Iron Cowboy: Wisconsin


PC: @jessakae
PC: @jessakae

The kind folks in Indiana were unable to take care of the laundry list of motor home issues during the short window of time that was available. That meant that we departed from our only potential saving grace with the motor home in the same state as when we arrived. I pulled another shift driving the big beast as we left Indiana and moved west towards Wisconsin. It was a little less nerve racking this time -a combination of becoming more familiar with the weight and balance of the machine, but also a renewed confidence that emerged as I thought back on my summer days as an illegal teenage truck driver.

I awoke with the family and the rest of the crew in the parking lot of the Prairie Athetic Club in Sun Prairie Wisconsin. We opened the door to the motor home and took the jarring 3 foot plunge down to the pavement  below – the mechanical stair case still refusing to leave the comfort of its retracted position.

There was a big commotion at the outdoor swim venue some 50 meters away. A bolt of panic shot through the eyes of wingmen Casey and Aaron.

“Daaaa! What time is it?!” Casey yelled. “Did we oversleep?!”

The two wingmen jumped into action, frantically running towards the crowd that lined the pool – terrified that they had potentially slept through their morning duties of transforming James into the Iron Cowboy.

When we reached the pool deck, the Iron Cowboy  was already in the water, but he met us all with smiles and a jovial demeanor – a stark contrast to my own face, still partially asleep. The wingmen had not failed, rather James had planned to surprise the crew by taking advantage of the extra hour by getting an early start on the swim.

Casey and Aaron expressed their relief the same way anybody would – they quickly changed into their Iron Cowboy speedos, climbed up onto the large overlooking deck, and began to dance provocatively to the beat of the blaring music. Onlookers, live news streams, and local athletes all watched as the two wingmen thrusted and gyrated on their makeshift stage – some 10 feet above the lane where James was swimming.  The finale was a pair of perfectly synchronized cannon balls, which made wakes that undulated through the neighboring lanes, and splashes that reached the far edges of the pool. I briefly posted a video of the ordeal, but soon thought better of it and quickly removed it from the World Wide Web. When Casey isn’t a wingman, he is a 1st grade teacher. The last thing I wanted was for him to suffer occupational repercussions if his impressive twerking abilities went viral.


As James gave himself a short break between laps, a local news agency took advantage of the pause and launched into a live interview. James looked up at the camera, doing his best to appear awake and speak loud enough for the microphone to pick up his voice.

WIsconsin swim



Near the end of the live conversation, the anchor simply asked “Why?” James looked back and responded with an explanation that highlighted childhood obesity and the threat it poses to the current generation. He paused briefly, then summed up his response with a matter-of-fact  declaration:

“We are doing this to promote childhood obesity.” He then turned around, and pushed off the wall continuing the 2.4 mile swim.

Everyone glanced around with bewildered eyes and furrowed brows.

“Uh…” Sunny interjected with a light hearted laugh.  “He means to raise awareness of childhood obesity. Not to promote it.”

The crew in Wisconsin was phenomenal. Every single moment of the day was intricately laid out in a neatly organized binder. There was a plan B, and C, and D, and on and on through the entire alphabet in the event that something went wrong.

Huge clouds rolled in and blanketed the sky as James met up with the local bike escort and prepared to depart.  By the time the group pulled out of T1, rain drops began to gently fall in a light drizzle that didn’t let up the entire bike course. A solid crew braved the rain and stuck with James over the 112 mile distance. As he entered T2, James dismounted his bike and calmly, yet urgently, said, “Turn on all the heaters in the Subaru. I need to warm up.”


The threat of hypothermia that had manifest itself in the oceans of Vermont, was back again. For a solid 30 minutes, James sat in the front seat of the car, eating his pre marathon meal as the heaters bathed his body in hot air, slowly raising his core temperature.

A large group waited to escort James out onto the Marathon course. Among the runners was  a local endurance athlete named Annie Weiss, who had made the trip up from Milwaukie for a chance to run with the Cowboy. Annie is an athlete who I have coached for a long time,  but I have never had the chance to meet her in person. She is, without a doubt, the most coachable individual I have ever worked with – putting in huge volume during the cold winter months of Wisconsin -most of it indoors. It was so great to finally meet her and talk about something other than training. She is in the process of transitioning from the roads to the ultra marathons of the trails. She has already had some great success, but her best days are still to come. Remember her name –she will be one of the greats.

James finally warmed up in the makeshift sauna, but he was pulled away in another direction before he could start the marathon. Financial and  logistical components, necessary to keep the Iron Cowboy team moving, required James to take a phone call and talk directly with a bank agent. The rain continued to dump outside and the huge crowd took shelter under trees, awnings, and tents, while James was transferred from one individual to another in the impossibly frustrating game of getting technical work done over a phone. It was mind numbing to see him struggle with such tedious – yet necessary – responsibilities, while in the midst of an undertaking of such epic proportions.  In my mind I imagined the conversation I would sarcastically have with James.

“Why did the Ironman take so long today James?” I would ask.

To which he would respond, “Oh that. Yeah,  I had to spend a half hour in a sauna during T2 to recover  from hypothermia, and then I was put on hold  by my bank and had to wait 45 minutes to receive  authorization to continue the race.”

“Typical.” I would respond with a nod, “Don’t you hate it when that happens?”

Wisconsin waiting

The soggy crowd applauded as James finally exited the motor home to begin the Marathon. The rain continued off and on as we made long loops on the bike path that surrounded Lake Monona. The body of water got its name from a Chippewa word meaning beautiful – “a fitting name”, I thought to myself as I ran along and admired the reflective sheen of the water, the flowered lily pads, and the thick trees that lined the shore. It wasn’t particularly grand, or breathtaking – there probably weren’t post cards boasting the scene, but as we skirted the meandering edge, mist rising up from the warm asphalt, the simple adjective used to describe the lake seemed to fit. “Beautiful” I said under my breath, nodding as I saw it for myself.


After one of the 6 mile loops, the Iron Cowboy and I dropped back behind the excited crowd, and for a couple of miles he was just James.  We chatted as we ran. He laughed and cried and cussed and vented about the struggles of the last several days. It’s still hard for him – there are sections throughout each day that seem absolutely overwhelming. His emotions are raw and come flooding to the surface with a single nudge. He is spent, but he continues to push through the struggle.  At the same time though, some of it has become almost comically easy for him. His body has adapted in ways that few people in all the world have ever experienced.  “Let’s just do a recovery Ironman today.” he jokes, any time the day seems to roll along without any major issues.

As we moved slowly and efficiently along a dark shaded area, he turned and told me about some of the ridiculous questions he has received over the last week, and how exhausting it is at times to stay diplomatic.  He laughed like a child as he recounted a conversation he had been a part of a few days before on the bike. An inquisitive cyclist had rolled up next to him and asked,

“So, uh…after you decided you were going to do the 50 Ironman distance triathlons in 50 days in 50 states, how did you decide which states to include in the 50?”

“Uh… … … what?!” James responded with a confused tone.

“How did you decide which 50 of the 50 states you would do?” the cyclist repeated.

“Um…I uh…I looked at a map and there were…50 of them?” James replied in disbelief, trying hard to soften the response.

“Why not do 5 more and knock off all of the Canadian provinces while you’re at it? the cyclist continued.

“Five provinces?” James asked.

“Yeah! Do 5 more and get all the Canadian provinces as well.”

“There aren’t just five provinces in Canada.” James responded matter-of-factly, losing his ability to humor the cyclist with each follow up comment.

“Yeah, I’m pretty sure there are.” The cyclist countered, clearly not knowing that James was actually born and raised in Cananda, where he had successfully graduated 3rd grade.

“No.” James simply responded while shaking head and pressing his lips together. “There are 10.” He continued, more to himself than anyone else. “10 Canadian provinces, and 3 Canadian territories.”

We joined back up with the group, James running a bit lighter now, as if the session to vent had lightened a bit of the load he was carrying as the Iron Cowboy.

A huge crowd had gathered for the 5k. James was met with loud applause as a spectator handed him a cheese cowboy hat, while Bucky – the official mascot from the University of Wisconsin, energized the receiving crowd.

CHeese hat

James put on the cheese hat and stood up on a small stage, flanked on one side by Bucky and on the other side by his trusty speed-clad wingmen.  He shared his message of making a change for the current generation, the audience hanging on every word as rain poured down and drenched the entire scene.


The speech concluded with wild applause and then just like that, the entire mass transferred out of the metal bleachers and began to move seamlessly as a single unit into the 5k run. Families ran together, encouraging their children – some just barely having learned to walk. When the 3.1 miles was complete, a solid group continued into the final 13 miles of the marathon – moving along  through the darkness like a band of urgent miners, bright beams bouncing along from our hand held  lights and head lamps.

Rain Boots

I stopped with one lap to go and wiped the grit from my body with a damp towel.  We loaded up the motor home and made preparations to leave. James would follow along in the van after the completion of the marathon. We were all tired and anxious to hit the road. There seemed to be a sense of urgency to get out of the rain, check Wisconsin off the list, and hope for a dry start in the next state. Casey and Aaron packed all of the essentials into their specific reserved locations, while Sunny got all of the kiddos tucked away and ready for the night. I sat down in the large driver seat and set the GPS for Waconia Minnesota. I settled in preparing for the next couple of hours, looked down the dark road, and turned the key.


I made sure everything was right and tried again.

Still nothing -the battery was dead.

“Well…” I thought. “We better add that to the list.”

Without a word Aaron and Casey arose from their seats. Just as they opened the door and jumped out into the rain, James and his escort were finishing the Marathon. A local runner from the group saw the problem and without even resting from the 26.2 miles, he sprinted towards his truck. Within a few minutes the motor home was roaring it’s sweet mechanical roar – Morse code beeping loudly in the back ground.

Although I have only been with the Iron Cowboy and his crew for a couple of weeks, this seems to be the theme of the entire journey.   (Overcoming challenges I mean, not deciphering messages in Morse code.) This feat would be impossible if it were not for the strength of Sunny and her amazing children, Aaron and Casey (the wingmen), the rest of the transient crew, and the incredible people in every state who don’t hesitate for a moment to do absolutely everything they can to help the Iron Cowboy on his quest. I have never witnessed a more collaborative, selfless effort by so many different people. That is a necessary component to accomplishing anything great. That same spirit of selfless collaboration is the key to affecting positive change in any societal structure – be it an interpersonal relationship, a family, a business or organization, or even an entire nation.

We as human beings, are social creatures. We are, by our very nature, designed to rely on one another. Have you ever wondered why it feels good to help another person? It is literally woven into our DNA. It is what we are designed at a genetic level to do.

Remember that the next time you need a hand. Don’t be afraid to reach out to those around you and petition their help as you strive to make improvements in your own life, and in the world around you.  Most importantly though, remember that the struggles of humanity are universal. There is not a single individual – young or old – who isn’t struggling in some capacity. Everyone of us has both the ability, and the responsibility to reach out and help. There is no limit to the good we can do if we forget our own self interests, and selflessly work in collaboration with those around us.

Look for opportunities to serve. We will find them on a daily basis. We don’t have to travel to the far corners of the globe to make a change.  We can simply start with the issues that lie directly in front of us and do whatever we – no matter how large or small.  We can smile. We can take time to listen.  We can lend a word of encouragement. We can decide in our relationships and in our families that we will make transformative choices that will lead to a better life.

We can even run 26.2 miles in the rain alongside a bearded Cowboy,  and then dash to the rescue of his cold and tired family with a big ol’ truck and a  worn out pair of jumper cables.

Simply do what you can do. If all of us do what we can, it will be enough.


9 thoughts on “Riding shotgun with the Iron Cowboy: Wisconsin”

  1. Love your posts almost as much as I love following the 50/50/50 epicness! It’s especially great your reminders to us that James is indeed human 🙂

  2. I have been following the Facebook posts and David Warden’s blog (his is like the left brain reporting and yours is like the right brain! Both equally as interesting in different ways) and now your entries. Your dialogue just keeps getting better each day. Really helps us to get insight on what this all means and validates why it is so addicting to follow and be part of!

  3. Hanging on every word! Thanking you for painting such a beautiful visual of the days they are experiencing. And for nailing it on the head about serving one another! Amen!

  4. It’s true that we can find opportunities to serve everyday. We just need to look around.

    This group continues to amaze me. Last night I ran 15 miles on a treadmill in hopes to be ready to run the marathon with James on Saturday. Mile 12 hit right along with all the pain from my hips down and I kept thinking “I don’t know how he’s doing this over and over. I’m dying with one run. But it also gave me the drive to push through the pain.

  5. I love reading your posts from state to state. I love reading about the good and the bad…..the strength this group has to keep moving every day and to still have smiles on their faces amazes me and makes me want to be a better person.

  6. I loved reading this! Cheering on one another makes us all feel the thrill accomplishment, and the desire to keep going. Your words about the day were inspiring. Thanks for taking the time to share your thoughts!

  7. Wow, what an adventure you’re on! Thanks for sharing it, and for reminding us to always do what we can.

  8. I ran into a gentleman from Madison as we waited in line together for our reg packets at this weekend’s Door County half iron in Egg Harbor, WI. He was wearing an Iron Cowboy t-shirt. I was jealous as mine hasn’t arrived, yet (understanding fully that t-shirt fulfillment is the LAST thing on everyone’s mind! ;). But, as your post suggests, this adventure is societal. Just having a brief conversation about the IC’s quest got both of us energized. Of course, my jealousy only grew when he described being able to ride and run with the Cowboy. Keep up the great work here and on the road. We’re all pulling for you, celebrating each day’s accomplishments.

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