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The Wealthy Stealthy Teenager

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Kenny was a high school friend of mine.

He was a mysterious Irish-Canadian kid who seemed to live completely independent of his parents. I never saw his mother or father and he never mentioned them – it was like he was just renting out their basement.

In appearance he was a Van Morrison/Bono cross with misleading sad eyes, of which you rarely saw due to his messy brown bangs.

To the untrained glance of a brutish knuckle-dragger, he could be mistaken as just plain weird, but in defence of the ignorant unwashed he did have some strange traits for a sixteen year old.

He was more of a listener than a talker – he rarely judged others with a disparaging assumption, and you could tell he always thought about his words before he spoke.

It was clear that he couldn’t be trusted.

Most everyone in our humble hood mistook him as arrogant and aloof, but we (our small gang of sociodroogs) loved taking in his dry sense of humour – it was like sipping on a cold Bob Newhart with no vermouth.

He would stay silent for long periods of time, seemingly bored with everything and everyone in his universe.

But he wasn’t.

The Clash

Kenny was the first kid in our neighbourhood to own a car. A 1955 red and rusty Chevy Bel Air with torn leather bench seats front and back.

When he first got the car I assumed it was nothing more than a source of power for his true source of pride – a state of the art stereo system.

His system had the most wattage I had ever seen, yet strangely he never cranked up the volume, and his taste in music was almost overly eclectic.

He would play the latest Elvis Costello offerings, follow that with Hank Sr.’s “Cold Cold Heart”, then Beethoven, Etta James, Tom Waits, and Curtis Mayfield (never in that order).

But I thought his favourite by far was The Clash.

It was Kenny who first introduced me to the four horsemen of punk rock, and after that I began procuring everything they ever recorded.

We loved listening to their early recordings, like Career Opportunities;

“Career opportunities the ones that never knock – Every job they offer is to keep you off the docks – Career opportunities the ones that never knoooooock!”

When playing the song Somebody Got Murdered, Kenny would always turn up the volume for the last part of the second verse;

“I’ve been very tempted to grab it from the till – I’ve been very hungry but not enough to kill”

I shared Strummer’s and Jones’ disdain for bitching layabouts and the “old and cunning” generation whose main intent it was to entrap the young into a life of drudgery and submission.

We were driving down Yates Street the first time I heard Strummer whisper;

“The voices in your head are calling – stop wasting all your time, there’s nothing coming – only a fool would think someone could save you – the men at the factory are old and cunning – you don’t owe nothing, so boy get runnin’ – it’s the best years of your life they want to steal”

Words that stole the hearts of millions – millions of kids like me. Their angst filled lyrics echoed my underlying beliefs, and I thought Kenny felt the same way too.

But he didn’t.

Painting by Michael Kozlov

Cruising With Kenny

Whenever you spent an evening driving around with Kenny it was memorable but patchy.

You had a fond memory of your time, but the details were foggy because he provided all his passengers with sticky fresh pot (elsewhere known as B.C. Bud).

And If you didn’t take a puff off his kindly offered joint you were getting high whether you liked it or not – he was a firm believer in keeping his windows up to ensure a superior sonic experience.

One summer night we were slowly meandering (best way to describe his driving) through “The Uplands“, which is an upper-class neighbourhood in Victoria – upscale enough to have fancy underground wired street lamps with circular opaque lenses.

One of our “alcohol only” friends in the back seat was experiencing a powerful contact high and suddenly burst out, “Hey….let’s throw bottles at the street lights!”

It was a common occurrence in The Uplands. Every so often some joy riders from “the other side of town” would get a thrill out of smashing a street lamp or two on a drive-by.

He continued, “Hey man, slow down up here…I got a dead soldier ready!” (empty bottle to throw)

“Nah,” Kenny replied, while passing a joint and adjusting an EQ knob on his stereo.

“C’mon man…these rich fucking bastards deserve it!”, our young vandal persisted.

“Hmm,” Kenny said under his breath, barely loud enough for me to hear in the front seat, and inaudible to our greening drunkard in the back, “I guess we all deserve something.”

We never stopped.




One night while walking back from a party we failed to crash, I asked my best friend Mark, “You ever notice how Kenny always turns up that one part in the song Somebody Got Murdered?” (I’ve been very tempted to grab it from the till – I’ve been very hungry but not enough to kill).

“Yeah,” Mark replied, “he can relate.”

“In what way?”, I questioned him further.

Mark paused for a few steps and answered, “Being hungry.”

He went on to tell me about the first twelve years of Kenny’s childhood (Mark was dating Kenny’s sister Angie so he knew more about Kenny than any of us).

They were poor, and his father was often unemployed due to his out of control alcoholism.

Angie said she remembered being scared and hungry a lot of the time, and she had vivid memories of her and Kenny collecting bottles to go buy hotdogs from the corner store.

One spring day when Kenny was nine or ten years old, his mother was at work, and he came home from school to find his father hanging by the neck in the shower.

He tried in vain to pull his father down but ultimately gave up and ran to the neighbors for help.

He watched as the police arrived and then the ambulance. When his deceased father was stretchered out of their single wide trailer he sat in the gravel driveway weeping, stone-faced and silent.

A few years later their mother remarried and moved to Victoria with her three kids in tow.

“See ya later man,” Mark said as he skipped over the curb down his parent’s driveway, “don’t tell anyone that stuff about Kenny, he would be pissed if we spread that around.”

It was two in the morning as I walked alone to my parent’s house.

I quietly eased open the door to the unfinished basement and climbed into my bed.

Mark’s words and Kenny’s story were still going through my head as I drifted off to sleep.

Stealthy Gains

By the beginning of our last year in high school I was beginning to get a handle on my enigmatic friend.

I had been all wrong about Kenny.

He was no rebel. He didn’t believe our generation was left behind in the rubble of western civilization, and he didn’t believe all the lyrics of our punk rock heroes – he just liked the new sound.

He wasn’t interested in tearing down the walls of conformity, and he was no anarchist. He was something far more dangerous.

He was an optimist.

He somehow had a paper route before he was old enough to get one, spent many of his weekend days cutting grass for neighbours, and collecting bottles for cash returns. He was the first kid in our neighbourhood who had a job delivering pizza, and he was the last kid to pump quarters into the arcade video machines.

I’m sure passersby just thought he was an enterprising kid, but it was more than that.

Every month after he bought his old car it had another improvement. Gray primer would suddenly appear on one of the once rusty quarter panels, and then one of the seats would be magically reupholstered.

Once when he picked us all up for another Friday-night-hotbox-on-wheels-tour, all the chrome on his dashboard was gleaming much more than before, and the pranged up rear bumper was perfect and shining – just like it did coming off the assembly line in ’55.

Not only was he breaking all the unwritten rules of teenage apathy and cynicism, he was accumulating wealth and belongings.

What a disappointment.

But we gave him a pass and we gave him respect. What else can you give a friend who provides you with comfortable transportation, free marijuana, and great music.

Born Black-Eyed

Our graduation was everything it should have been for our class of 1981 – it was pathetic and nauseating in equal doses.

Me, Mark, Kenny, and three other baked-and-battered boys rented a limousine like some such horrid and vomitus cliché.

We got the limo driver high and he started telling us about his glory days as a defensemen for the Boston Bruins.

I didn’t care if he was for real or not because it was entertaining to hear the old guy momentarily happy in his brag.

But one of the guys couldn’t let it go and blurted out, “Yeah right Bobby (Orr) – how are your knees?!”

We all laughed except for Kenny who leaned his head back and nodded, saying, “I swear you guys were born black-eyed.”

He never elaborated, and we never asked him to. We knew we weren’t likely to get a straight answer out of him anyway.

That was the last time I saw Kenny.

The Landlord

About a year later Mark was delivering pizza to a small duplex out in Esquimalt, and to Mark’s surprise Kenny’s older brother Adam came to the door.

After the business of pizza for cash was concluded, Mark asked Adam how Kenny was doing.

Adam said Kenny owned the duplex. He lived on one side, and rented out the other to Adam and his girlfriend.

Even more surprised now by this revelation, Mark jokingly asked if Kenny had won the lottery.

Adam told Mark something we already knew – that his secretive little brother started doing auto body work “under the table” before he even had a drivers license, and had been squirreling away money since his early teens.

But Adam went on to reveal something we didn’t know.

Kenny finally finished the restoration of his ’55 Bel Air and sold it to a wealthy car collector in Kelowna. The money he got from the sale, combined with all his other savings, gave him enough for a down payment on the small duplex.

Whether he had a co-signer or not I’ll never know, but judging by the house he grew up in I doubt it.

Ten years later at a high school reunion Mark learned that Kenny had his own auto body shop.

And 38 years later, as your humble narrator lays in a Saskatoon backyard, in a bathrobe, watching the third season of Rockford Files on a “device”, I can report to you that Kenny now owns a chain of seven auto body shops and three restaurants in Western Canada.

Not long ago I managed to track down his email address. I sent him these links, and two words.

“Feelin’ Alive.”


Brent Truitt is a full time Internet marketer and part time blogger who lives in Saskatoon, Canada and Southern California. You can connect with him on Twitter @IAmBrentTruitt    



  1. This reminds me a lot of the Millionaire Next Door in that it is typically the person society would least expect to be wealthy who is secretly working hard and piling away money (vs. spending on outward symbols of wealth). This story, however, goes one step deeper with the motivations of a kid who grew up in an “out of control” household who wanted to gain control and be able to navigate life without the financial woes of his parents. Amazing. Thank you for sharing!

    • Thanks Mrs. AR. – very kind words and glad you enjoyed Kenny’s story. It is amazing how some people who grow up with less end up thriving due to their fear of being broke.

  2. Peter Peter

    Man, you are an awesome writer. I like to dig personal finance blogs, but your posts are so different, more like I read a chapter from a fuckin’ good book. Maybe I just can relate to the punkish ambient, but I like it very much. Thank you for sharing.

    • Hi Peter. Thanks for coming by and leaving a comment on Kenny’s story (and the compliment – it feels good to hear that).

  3. Great story that captures the process of thoughtful planning, hard work staying focused and sharing the ride. A car restoration hiding in plain sight, very cool.
    People really don’t recognize the process of saving and accumulating wealth, only the result. The restoration of a car is a great example, in this case the Bel Air. Only afterwards, they read or hear about a success story and wish they were as “lucky”. Most cases, luck is disguised as hard work, focus and having a plan and sticking to it.

    • Thanks for swinging by and leaving a comment Franklin. ‘Only afterwards, they read or hear about a success story and wish they were as “lucky”’ – ain’t that the truth. Unless one inherits their wealth they either won the Powerball or they worked their tail off early on.

  4. Steve Steve


    Great story. I have read some others like this and I wish i was more like Kenny was with his money when I was growing up.

    On a side note.

    Brent, you hit on 3 of my favorite things. Hockey, The Rockford Files and The Clash. I was fortunate enough to see The Clash two times growing up in Minnesota and saw Joe Strummer when I was living in Southern California right before he passed away. “The only band that matters”.

    Looking forward to reading more posts from you.


    • Wow back Steve. You saw The Clash twice AND Strummer! I am JBR (jealous behind reason). Thanks for the kinds words and hope to see you back here another time.

  5. Stephen Alvaro Stephen Alvaro

    LOVE, LOVE, LOVE this story. You combined personal finance and The Clash! I have been drawn to those Clash lyrics you mentioned as well. I am looking forward to reading the rest of your site.

  6. aperture aperture

    Brent, I really enjoyed this brilliant story. Thanks, I look forward to reading more.

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