Live Like A Billionaire – Student to Teacher

Unexpected mid-week power day.
It’s hard to put a value on the ability to “drop everything”.

What does the title of this piece bring to mind?

  • Jet?
  • Multiple properties?
  • Luxury yacht charters?
  • Seven-figure burn rate?
  • Handing out favors to friends and strangers?
  • Being hailed and feted?

One of the best parts of my coaching journey was getting to know “the well adjusted rich.”

I’m going to spend a few Thursdays running through the lessons I learned from watching people who have a different set of limits.


The Best Teachers You Can Find

My journey started ten years before I got the job.

First, I was a student…

Meeting Joe Friel: Joe is the founder of triathlon coaching in the United States. I had the chance to spend a weekend with him in the Spring of 2000.

By the way, this is how you might get a mentor interested in you…

  • I went to him
  • I showed him how he’d helped me
  • I listened to his advice
  • I went away and did it

Something he said stuck with me, “I’d never met someone who understood my teaching as well as you.” I didn’t just study his philosophy, I tried to embody it.

Joe started me as a coach, helped me win races and wrote a book with me.

Great deal for both of us.

The strategy worked once, so I repeated…

John Hellemans, Scott Molina, Dave Scott, Mark Allen => I was able to learn from the best.

I shared what I learned, for free, widely.


Eventually, I was a teacher…

A decade later, I turn up in Oceanside, on a road bike, in March, and crush most everyone over 40 in a 70.3 race.

Two guys, I’d never heard of, reach out for a call and I accept. I didn’t know they were friends and checking me out, separately.

I get hired and have the chance to look under the hood of the well-adjusted rich.

Turns out my client was a successful finance-guy, who stayed in the game.

His life was, and remains, the best-case scenario of a life I decided not to lead.

Becoming world-class, publicly, creates unexpected opportunities.


Let’s call this Chapter One.

If you’ve been watching me on Twitter – you can see I’m following a similar playbook in 2022.

Not towards any specific goal => simply to connect, be engaged and create unexpected opportunities.

Mentors and Peers

How can I stack the deck in favor of being a good guy?

First, I try as much as possible to get positive influences to visit me.

Second, I’m willing to travel to hang out with people that are what I’d like to become. Back when I was an elite athlete, this drove my travel schedule. These days I travel less but it remains a big chunk of my year.

My family allocates 14 weeks per annum for my travel.

  • 4 weeks of that is my wife and me
  • 2 weeks is used for continuing education
  • 8 weeks is for my own uses – these days split between non-Boulder family visits and personal trips, mainly to ride.

My daughter joins me for two weeks of the above and we do another two weeks worth of in-state travel together.

Pulling it together, I have a job description that gives me 16 weeks per annum of variation from my normal routine.

Before my daughter was 2 years old, this allocation would roll between 30 and 40 weeks per annum. As I’ve simplified my life, and released my expectations for triathlon greatness, I feel more free with less travel.

In considering a trip, I ask myself three questions…

  1. Are the people that I will see infused with goodness?
  2. How do the people make me feel?
  3. If I turned out like these folks, would I be ok with it?

There are plenty of people, and companies, who pass the test. Make a note when you meet these people and keep them in your life. 

While its tempting to vacation in, say, Vegas, we are more likely to generate success by keeping the goodness in our lives. For the key relationships (bosses, mentors, clients, peers) visiting on their home ground will broaden your understanding, and keep you humble with your capacity to predict. The on-the-ground situation is nearly always different than I imagine.

The focus on “the good” is an ethical litmus test. I’ve caught myself valuing winning over kindness, an occupational hazard if you’ve spent time in a field (sport) that values relative performance. I’m also prone to errors of judgement due to wealth and beauty.

Choose Wisely.