The Kid in the Boat

The first time I heard of Pennywise I was on a chair lift at Harper Mountain outside Kamloops, ten years old, day two on a snowboard, cold cheeks, sun about an hour up. My instructor was the coolest person I had ever met. Headphones in. Tricks down the mountain. Moved like he did not owe anyone anything. On the chair lift his toque had PW stitched on it. I asked what it meant. He said it was a band he liked. That was the whole conversation. I never brought it up again.

I got to a record store as soon as I could and bought the CD with money I had made shoveling driveways door to door.

I pumped those lyrics through my head every day for years.

That is how taste actually transmits in the real world. Not from algorithms. Not from “you might also like.” From one cool older guy who did not know he was teaching you anything. He was just being himself. A toque, some stickers, headphones in, sun coming up over a mountain. To a ten-year-old that is not a band recommendation. It is a whole operating system for how to be a person.

I do not remember his name. I do not know if he is alive. He has no idea that the morning he taught a small kid to make a heel-side carve on Harper Mountain was also the morning he handed that kid a worldview disguised as a punk band. He was probably twenty-two. Hungover. Working a season job. The smallest event of his year was the largest of mine.

A couple years later, twelve or thirteen, I was reading a Don Lapre book on classified ads because I wanted to be rich. I sent away $2.50 of a $10 weekly allowance for a brochure that promised to teach me how. The brochure was a knock-off of Abbie Hoffman’s Steal This Book — which I would in fact eventually steal, years later, knowing the joke. One of the schemes inside it was: start a publication, write to record labels asking for promo product, review it, mail it back. Labels send free music to the press. So if you are the press, you get the music.

I was the press.

I named a publication. I gave it letterhead. I made up readership numbers because the form required a number to be taken seriously. I sent professional-looking requests to A&R departments at every label that had a band I cared about. They mailed me CDs. Cassettes, at first. By the end of the run they were mailing me CDs. I lived through an entire format dying inside one teenage hustle.

And I did the work. I listened to every album. I wrote every review in WordPerfect. I laid them out properly. I made it look nice. I printed one copy and mailed it back. The publication had exactly one reader per issue and that reader was the only reader who mattered — the label that sent the CD. From their side the transaction was identical to the transaction they had with Spin. They sent product. They got a written, formatted, legitimate review back in the mail. They could file it.

Eventually a woman at one of the labels figured out I was a kid. She wrote me a letter. She was not mad. She was charmed. The whole thing was so clearly driven by genuine love of the music that there was nothing to be mad at. The artifact I was producing was real. The labor was real. The love was real. The only thing that was technically false was the size of an audience nobody was actually counting.

I never told anyone about this for twenty-five years.

I think I had filed it at fourteen under do not mention this and I just kept the filing all the way into adulthood, never opened the cabinet, never asked grown-up me to look at what was in it. Grown-up me looking at it now sees a kid who did honest work for an honest trade and made up a number on a marketing form. Compared to what counts as normal in the actual music industry — payola, manufactured charts, paid PR, fake influencer discoveries, streaming farms — a kid in Kamloops listening to every CD and writing real reviews on his bedroom floor is a model of integrity.

It is also the same play I run now. A LinkedIn page with a few hundred followers, the right few hundred, beats fifty thousand of nobody. Vanity metrics are for people who do not know who their audience is. I have never been one of those people. I was not one at fourteen either.

Roll back further. Before the publication. Before the snowboard instructor.

I was seven, eight, nine years old, alone in a small fishing boat on Pinantan Lake outside Kamloops. The deal was: be home for supper. That was the whole rule. Nobody knew where I was during the day. Nobody could call me. There were no phones. The motor coughed sometimes and I had to figure out what to do about it. I had to read the weather myself. If a fish was bigger than expected I had to handle it. If it got cold I had to come in. Nobody narrated my choices and nobody recorded them. I rowed back at suppertime slightly more competent than I had been at breakfast.

Do that a few hundred times across a childhood and you build a kid who at fourteen is not fazed by mailing letters to record companies. At twenty-five is not fazed by walking into a drop-in centre or a prison. At forty is not fazed by cold-calling an oil and gas executive who has no reason to take the call. People think this is confidence. It is not. I ran out of things to be afraid of by the time I was twelve.

My best friend Joel and I had bikes. That was the other technology. Two kids, two BMX bikes, an entire town and an entire lake and an entire forest, and the only rule was be home for supper. We disappeared for the day. We learned loyalty because if Joel wiped out three miles from home I was the ambulance. We learned negotiation because we had to agree on where to go for ten hours straight. We learned comfortable silence because not every minute needs talking when you are already there together. None of that gets taught in a classroom. None of it gets built through a screen.

In the winter we played hockey on the lake. We skated until our legs were jelly and walked home in the dark with the cold burning in our lungs and felt like the most alive people on earth. My body learned what my body could do. Kids today often do not know that. They know what their thumbs can do. They do not know what it feels like to come back from the lake, inhale a meal, pass out at seven, and do it again the next morning.

The axe.

When I was eight my dad would chop firewood and I would help. My mom would pay me five dollars a bundle. It was never assigned. It was available. My dad was going to chop the wood anyway. If I wanted candy money I could swing the axe. If I would rather trampoline I could trampoline. Either way nobody was mad.

That is a different thing than chores and it produces a different kid.

Chores teach compliance. Optional paid work teaches agency. I learned that money is something you go and get when you want something, not something you are owed for existing. I wanted candy. I went and got candy money. Clean loop. No resentment because nobody made me do it. The only person I was negotiating with was myself: how bad do I want it? Bad enough to swing the axe? Then swing the axe. Not bad enough? Then do not.

That is the foundation of every entrepreneurial move I have made since and it is why I have never been a good employee in the conventional sense. I was never wired for assigned work. I was wired for opportunity recognition. The wood was sitting there. The snow on the neighbours’ driveways was sitting there. The Don Lapre brochure was sitting there. The record labels with their promo budgets were sitting there. Curtis White’s direct line was sitting there. Ibrahim’s family in Libya was sitting there. The pattern is identical at every scale. Something is available. Most people walk past it. I pick it up and swing.

I was also not just chopping for my own candy. I was chopping for Joel’s candy too because he did not get an allowance and I was not going to sit on a curb eating candy in front of my best friend while he watched. Nobody taught me that. I just could not not. That is the same wiring that has me doing free Korean reunification work for years. The same wiring that has me building a dining system for old people. The same wiring that has me running the Libya facilitation carefully because Ibrahim’s family put their honour on me.

Generosity as a strategy is exhausting and obvious. Generosity as a default is the kind that actually moves things, because it does not get tired and it does not keep score. I am the second kind. I have been the second kind since I was eight, swinging an axe for two kids’ worth of candy.

A perfect day at nine years old went like this. Chop wood. Swim in the above-ground pool. Trampoline. Rotate. Fish. Pass out. Wake up. Do it again.

That is not a schedule a parent designed. That is a kid who had figured out his own rhythm and ran it on loop because it felt right in his body. Most adults pay wellness coaches thousands of dollars trying to reverse-engineer what nine-year-old me was doing for free in the backyard. Physical labor. Cold water. Full-body play. Real tiredness. Real sleep. The protocol was there before I could spell it.

My mom is the quiet hero of this whole story and I want to be clear about her contribution because parents who do it right almost never know they did it right. She made specific choices that other parents would not have made. The trampoline. The pool. Letting me take the boat at seven. Negotiating the headphones-in-class deal in grade three so I could keep listening through social studies. Paying me per bundle instead of just handing me allowance. Letting me spend my $10 a week on a sketchy mail-order brochure without lecturing me about it. None of those were accidents. She decided early that I was a person, not a project. She gave me tools and range and trusted me to figure out what to do with them. Then she got out of the way.

That is one of the hardest things to do as a parent. The instinct is to manage, narrate, optimize, protect. She did the opposite. She built an environment where competence could grow on its own and she stepped back and let it.

She did not run the same play with my brother. He is four years younger. We had moved by then. He grew up in the city of Kamloops, not on Pinantan. He never got the boat. He never got the axe. He never got Joel and the bikes. And I think she over-corrected with him after watching where my range eventually took me, into the prisons and the rough rooms. She got scared by the shape of my freedom and she pulled the protection in tight on the second kid. He is in his thirties now and she still pays his rent.

Same mother. Opposite move. Opposite outcome. He is soft. He is entitled. To him it is water to the fish — he does not experience it as entitlement, he experiences it as baseline reality. That is the whole psychology in one image. Entitled people do not know they are wet. They have never been out of the water.

You cannot tell a fish about water. You can only take it out of the water, and that is cruel and risky and most parents will not do it to their adult kid. So my mom keeps paying the rent because the alternative is watching him gasp, and she remembers watching me in the rough years and she swore she would never watch a kid of hers struggle like that again.

I cannot fix any of it. But I can keep being the proof that the hard call worked. Just by being who I am, I am the evidence she did one of the two right.

The contrast in my life since has been the wildest thing about it. I have been in cells with men who killed people and I have been in lobbies of Four Seasons hotels. Drop-in centres in winter and charity galas where old ladies kissed my cheek. Federal time and ambassador-level meetings. Cleaning floors and consulting on deals worth millions. Most consultants cannot read a Libyan oil executive and a senior at Vi CARE in the same week without getting one of them wrong, because most consultants only know one room. I can read both because by the time I was twenty-five I had already entered every kind of room there is.

I entered the first one through the mail at fourteen.

The same kid keeps showing up. Pennywise on the chair lift. Don Lapre brochure on the kitchen table. The boat at seven. Joel on the bikes. The axe at eight. Five bucks a bundle. Headphones in grade three social studies. Walkman to Discman to Shockwave MP3 to phone. Cold-calling Curtis White at IPC. Building a brand for Ibrahim and running the trust chain through Nasser to Belhaj. Korean reunification work for years with no paycheck because it is the right thing and because all Koreans are one people and because someone has to say it. Eighteen thousand LinkedIn connections, every one of them sent by hand. The kid who would not eat candy in front of his friend.

The medium changes every few years. The kid does not.

The stones are cast. This is me.