My Epic Failure

It was Dec 26th, 2010.

I walked up to my parents’ home in the suburbs of Edmonton, Canada.

Snow crunched under my shoes. My breath created a puff of fog that danced in the air with every exhale.

This was the home I’d grown up in.

So many sweet memories of playing street hockey out front, playing drums in the basement, and playing catch with my Dad.

This was the site of countless Sunday Night Suppers. So much love and warmth in this home.

I was there, on Dec 26, 2010, to be a good son.

In Canada, Boxing Day shopping is a big deal, like Black Friday or Cyber Monday in the U.S.

In Edmonton, the mecca of Boxing Day shopping was West Edmonton Mall, the biggest indoor Mall in North America (yes, bigger than the Mall of America).

As fierce as the competition was inside the mall for great deals, it was just as competitive outside to find parking spots.

So I was going to pick up my family, drop them off at the Mall’s entrance, then spend 45 mins circling for a parking spot.

As I walked up the front steps of my parents’ house that day, little did I know my world was about to totally collapse.

The previous 18 months had been the hardest of my life.

The housing crash wiped me out. Lost $100Ks, mostly investor money.

My band broke up mere minutes before going on stage at the Western Canadian Music Awards. 6 years, 150 shows, 3 sponsors, airplay on 8 stations.

All gone.

I also found out my mentor was actually the lead promoter of an illegal investing scheme. This scheme later turned into a $12M Ponzi scheme.

The owner was convicted in court and left the country. Families lost their whole life savings. I was stunned.

Little did I know things were just getting started.

The colossal stress of all of this, combined with the exhaustion of working 80-100 hours/week, all came to a head.

As I stepped into my childhood home that morning of Dec 26, 2010, my Mom’s warm welcome was quickly replaced by concern.

“Honey, are you okay? You look like you have a small limp.”

I took off my winter mitts and big, puffy jacket.

I untied my shoes and we rolled up the cuffs up my jeans to inspect more closely.

“Oh wow,” she gasped.

I looked more closely too. In the handful of minutes it took me to drive over, my feet had swollen significantly. My feet were huge. It looked like I’d rolled both my ankles playing basketball.

“You should stay home. You can’t be walking around a mall for 8 hours on feet like that.”

Over the next 7 days, my feet puffed up, ever bigger and bigger.

The swelling also started moving up into my shins and hips too.

It became too painful to walk.

Then too painful to even stand.

I found an office chair and started pulling myself around my parents’ house to get around.

Simply getting a glass of water became a 15-minute odyssey. The pain was so bad, I could only move a few feet in the rolling chair before I’d have to pause and let the pain cool off before I moved a few more feet.

Mom and I saw three different doctors, all independent of each other.

All three gasped when they saw my condition. All said something like, “Wow. This is an ultra-rare illness known as Erythema Nodosum. I’ve only seen this twice in my 30-year career.”

There was no medication for me to take.

There was no PT for me to complete.

Cruelest of all? There was no timeline.

“Doc, will this take days, weeks, months?” I asked.

“It will take as long as it takes,” they replied.

Dang.

I moved back in with my parents for full-time care.

I couldn’t shower normally, so I had to pick between sitting on a plastic stool in the shower or getting a sponge bath in bed from my Mom.

After the first few days of struggling in my new reality, the big questions started to come.

Would I ever walk again?

Would I ever kick a ball with a future son?

Would I ever walk a future daughter down the aisle?

These questions were actually a luxury compared to the bigger issues screaming in my face.

How am I going to pay for my mortgage next week?!

All day, every day, I lay in bed, staring at the ceiling, trying to understand how I’d ended up here.

Every day was an emotional rollercoaster.

I felt deeply humiliated for failing so publicly. All my friends, fellow Entrepreneurs, mentors, all knew I’d totally failed.

I felt so resentful of so many people - my mentor, the market, even my bandmates. Everything I’d worked for for the last 5 years was totally vaporized.

I also felt so helpless and hopeless.

I had no way to work and make money.

I was over $325K in debt (in today’s dollars) with no way to pay any of it back.

Had my Mom not paid my mortgage for me for three months, I would have gone double-bankrupt.

I had some of the darkest thoughts of my life.

Sometime in Feb 2011, the second month of my illness, I had a moment that would change my life forever.

I woke up in the same bed I’d woken up in for weeks on end.

As my eyes focused on the ceiling, suddenly I felt a flood of warmth wash through my body and a tingling ripple through me.

I heard a voice I’d never heard before: “Is this what you want?”

I knew what the voice meant: do I really want this path of Entrepreneurship, with all of the highs, lows, winning, losing, risk and reward?

Time stood still. I have no idea if a second, minute, or hour had passed.

Then I heard a second voice. This one was weak, small, buried in the deepest corner of my heart.

But it was also crystal clear:

“Yes.”

Suddenly a flood of realizations hit me. I’d been chasing fame and fortune, when what I needed to be chasing was TRUTH and MASTERY.

Meeting God that day was, no doubt, the moment my body started to heal.

As my body started to heal, I stumbled across this quote:

Many years earlier, I felt inspired by a quote from a famous author that said, “Live for 5 years like few are willing to, so you can live a life few ever will.”

He was implying you should sacrifice everything - health, friends, family, body, vacations, etc - for 5 years to set yourself up financially for the rest of your life.

I bought that, hook, line, and sinker.

The problem now was that I was six years into my journey and I was $300K+ worse off than when I started my journey.

Oh, and I couldn’t walk.

So to read the ancient wisdom of the Bahagavad-Gītā, describing that I wasn’t owed any kind of result, had the thud of truth. I didn’t like it, but I also couldn’t deny it.

So I started asking questions like:

I realized my entire illness had been one of the greatest gifts of my life. I’d been in the wrong businesses, for the wrong reasons, with misaligned people.

I’d just been too damned stubborn to see it. IT took God’s hand to reach down, pull me up by the scruff of my neck, and park my behind in “time out” until I could get my head straight again.

After 3 months of illness, I started to walk again.

I had no more room or financial runway to try and hit home runs in real estate.

I had to cobble together a bunch of singles. Bunt if I had to.

I’d painted houses back when I was 19. It’s all I knew would make me money quickly. So I started offering to paint houses again.

My Mom, a teacher, helped promote my painting services to other teachers she knew.

I started doing estimates. I’d tell the teachers:

They were excited to sign up. Before I’d agree to the job, I’d share one last detail:

“There’s one catch: I need permission to paint anytime, day or night. Do we have a deal?”

They all said yes.

They probably thought I was going to paint from 5pm - 10pm.

No.

I wanted to paint from 10pm to 5am, right through the middle of the night.

I wanted to learn marketing. All the best webinars, from all the best U.S. teachers, were in the afternoon.

I also wanted to network locally to find clients for my new marketing business. All the networking happened at either lunch or dinner time.

So I needed to stay available from noon until 9pm to build my new business.

That meant I could paint from around 10pm until 5am, then sleep for a few hours, then get up to go to the next networking event.

Night-in and night-out, I’d show up at a teacher’s house, and paint through the night. I’d have headphones in and I’d listen to webinars, podcasts, and audiobooks, all about marketing and sales.

More than once, as the sun was rising, I’d be wrapping up my job site and I’d say hello to the homeowner on my way out the door.

As bizarre as this working arrangement was, it worked.

It took 6 months of learning and networking before I had enough clients to replace my painting income.

Every week was a struggle as I teetered financially. The #1 metric I pursued wasn’t revenue or profit or even money in the bank. I just wanted to get a high score on the number of consecutive days I could go without asking Mom for more money. That was it.

In all, it took me 7 years and two different businesses, but I paid all of the debt off. I didn’t think I’d ever make it, but I did.

To this day, I’m still learning lessons from that 2011 episode.

For example, the financial terror I felt in 2011 forced me to learn how to navigate high-stress, financially delicate scenarios.

When the 2020 pandemic hit, and everyone was losing their minds, I felt surprisingly calm. "I’ve been here before,” kept turning in my mind, over and over.

I spoke dozens of times, often at no-charge, on a variety of podcasts and webinars, teaching Entrepreneurs how they navigate their deep fears. My story of resilience and comeback from 2011 offered comfort and clarity to many. I received dozens of thank you emails, some tearful, sharing the relief of having a clear path amidst the chaos.

I’ll continue to share these kinds of lessons through this newsletter.

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Onwards and Upwards,

P.S. I also produce lessons on YouTube; consider checking it out here.