Blindspotting

arms around the world

Sat, 27 Jun 2026 16:30:27 -0700

what's your personal guarantee worth?

Every summer when we were kids, our mother would ship me and my brother off to lake country in northwestern Ontario. We spent our time swimmin', boatin' and fishin' with our large collection of cousins and under the tutelage and safe hands of one of our three uncles. Much of what I learned about being a man and a good person I took from these formative summer trips.

My mother and aunt Dorothy grew up under the watchful eye and protection of my scrappy uncle Bob. He was one of those people who would-be aggressors just knew not to fuck with–someone who would lay his life down for someone he loved. "Hubby", as he was known by pretty much the entire community of Kenora, lived for his family and for time on his house boat. The complex web of channels, straits and islands that made up the Lake of the Woods was second nature to him.

On one of these occasions, we were several hours down the lake and I was getting a bit cagey in the tight quarters of his floating sanctuary. We came upon a derelict boat abandoned on the shore of an uninhabited island and I wanted to go see it.

Think about all the beautiful fortuitous things that've happened in your life and the ugly scary things that haven't. These are the countless events and nonevents that have given you the gift of being here now instead of not existing at all. Regardless of how resolved you are in your relationship with her, at the top of that list is your mother.

You would not be here to read this if it wasn't for your mother and countless other mothers, grandmothers, stepmothers and aunts. You also wouldn't be here without mine as I would not be here to write this.

My mother lived to see a great many things, including the birth of her great-granddaughter Josefina, but she did not live to see her 89th birthday. She passed this year on Good Friday and in many respects it was a very good Friday. She left this earth on her own terms, complete, fully resolved and with my brother and me at her side.

Many of the big things she did in life were entrepreneurial. Muggs, as her older sister and my aunt Dorothy called her, was the youngest of six in a large post-war family from Kenora, Ontario. Go West young woman! And West she went, in search of the grand adventure of life, finding meaningful employment and eventually life as a single mother to two young boys.

She kept the wolves from the door and managed to launch two hungry teenagers onto successful paths of adulthood by starting her own business in the middle of a brutal recession. I don't remember a single moment of financial scarcity. I'm not...Read More

scaling equity

Sun, 08 Feb 2026 10:15:16 -0800

I was born in Calgary and have lived my whole life here. I began my professional career in my twenties as an industrial designer after a short stint selling lemonade when I was seven. Alberta does not have the large industrial base that exists in the US or Eastern Canada, so throughout my five years of design school it was always abundantly clear that I was not likely to get a job at a manufacturing company. I was going to have to hardscrabble my way into my own consulting business.

Entrepreneurship was not an unnatural posture for me. Calgary and Alberta in general have a long and storied entrepreneurial history dating back to the pioneering spirits of the people who settled here (both indigenous and European) and the farmers, ranchers and the wildcatters who raised their families and fortunes here. I had already launched my first business manufacturing climbing mitts while I was still in engineerting school and managed to get into design school on the basis of that adventure. I was raised by a single mother who started and successfully ran her own business to raise my brother and me after a nasty divorce. She was born in a small town in Northwestern Ontarrio and was the the most entrepreneurial of her siblings, so going west to the most entrepreneurial of cities was a natural choice for her too.

Part way through design school I joined a new industrial design consulting business started by one of my professors and a fellow student. After a year that business imploded and I started getting calls from clients with unfinished projects. And just like that I was in business. What a stroke of luck! In the next few years before graduation and after, I made just about every mistake a young entrepreneur could make learning to run a business. But eventually my partners and I built one of the top firms in the province. I did not waste a rare and precious opportunity, even though I did not...Read More

trigger warning

Sun, 07 Dec 2025 18:17:42 -0800

If you’ve spent years leading complex systems and dynamic teams of high performers through moments of intense pressure and stress, you already know that strategy and intelligence aren’t the limiting factors: energy, timing and human factors are. Leadership ultimately lives in the collective nervous system, not the org chart; “triggering” events are where you either lose or gain perspective and engagement. The most effective leaders learn to metabolize stress rather than export it to their teams. Drawing on neuroscience, lived experience, and systems coaching, we offer a practical theory and a usable tool for anyone considering the shift from being the one with answers to being the one who stabilizes the field so better answers can emerge. Keep reading if you’re curious about becoming more effective as the head coach of your team and sense that leadership is less about control and more about emotional co-regulation in your relationships. This post is a special edition so it is a bit more epic than usual. Here are the two questions we are grappling wth in the post:

What does it mean to "get triggered"?

How do we make the best of a triggering event?

Game on!

•••

Near the end of my time in elementary school, I had a run-in with the school bully. Most Mondays, he would pick some hapless victim to beat up in front of the rest of the school on Friday afternoon. When I got tapped, I made it clear that I was not participating in this weekly ritual, but I showed up anyway to preserve my honour. I declared my refusal to fight, he punched me in the face twice and I walked away in apparent shame, unaware of the crucial life lesson I'd just learned...

•••

We have been here before. In 2007 the danger was moral hazard, which was the tendency for human experts to take risks they would not personally bear. Today the danger is amoral hazard, which is what happens when systems optimize without conscience, judgment, or any felt sense of consequence. Generative AI reflects us, while agentic AI acts without us. As we hand more decisions to machines that cannot care, cannot feel bad, and cannot calibrate intention the way humans do, we risk recreating the same misalignment that once crashed the global economy, only faster and at a larger scale. The promise of AI is real, but only if we remain the adults in the room, holding the values, making the judgments, and remembering that intelligence without empathy is not wisdom.

•••

I first encountered the concept of Michael Burry in a Vanity Fair article in the spring of 2010 called “Betting on the Blind Side.” The financial crisis was still crippling the economy and society at the time; I was deep into my first burnout as my adrenals crashed alongside the stability of the global financial system. Burry had been diagnosed with Asperger’s Syndrome (now known as Autism Spectrum Disorder or ASD), and he used that “gift” to pore over the fine print of thousands of mortgage documents in machine-like fashion, resulting in an investment thesis to short the U.S. subprime mortgage market....Read More

the age of extended mind

Sun, 05 Oct 2025 15:59:03 -0700

Prehistoric man wasn’t the fastest, biggest, strongest, or best-equipped animal in terms of claws and fangs, but we didn’t perish. We learned to use fire, wood, bone, and stone fragments, animal furs and skins, and other found materials to create objects of survival, which further evolved into objects of art and social communication. Homo sapiens are not the only creatures of nature to make and use tools, but we certainly are the only species that have made it into a superpower. Tools are extensions of our native power, and as we have learned to use the tools we invented, the tools themselves have helped us invent even more powerful tools to exert leverage on the wild world around us.

In their 1998 paper The Extended Mind, authors Andy Clark and David Chalmers argue that cognition doesn’t stop at the skull; it extends into the tools, environments, and relationships that actively participate in our thinking. Most of us don’t bother memorizing all the phone numbers of friends and associates. Children today have never had their hands on an actual paper map (much less a parchment one), and no one does long division by hand, or by abacus, or even on an HP-41CV (my calculator of choice in engineering school). These functions and many more now reside in silico on a permanent appendage called the smartphone. It was not that long ago when we all had rotary phones and hated “dialing” friends with zeros and nines in their phone numbers (the humor of that probably ends with baby boomers). At some point soon, we’ll have Neuralink-like implants in our brains, hooked up to the latest in generative AI. At some point it will be difficult to discern where the cybernetic boundary between...Read More

raising entrepreneurs

Wed, 17 Sep 2025 08:22:48 -0700

Raising entrepreneurial children isn’t about grooming them for business. It’s about modeling the realities of creating value in the world, giving them a front-row seat to both the stresses and the satisfactions, and then trusting them to step out on their own. Raising entrepreneurial staff is much the same. Young team members also need exposure to the ups and downs of building something, room to test their own independence, and leaders who trust them enough to grow beyond the “operating systems” they inherit. Whether at home or in business, the challenge is the same—creating the conditions where spirited young people can step away, discover themselves, and return as capable equals.

•••

While I was in design school, I also completed most of the courses that our business school was offering in its MBA on entrepreneurship. There was great synergy between what I was learning about design thinking and what I learned there about new venture development.

Dennis Rey taught one of the core courses on entrepreneurial theory. He had spent four years studying what differentiated the most successful entrepreneurs from the rest of the pack. His not-very-scholarly-sounding insight was that most successful entrepreneurs were "likable". This meant that people would go out of their ways to help them.

He also said was that if even one parent was an entrepreneur, it was very probable that a child would follow suit and become an entrepreneur. This was in the days before I had my own two children, but his idea stuck in my brain. Both of my children have started their own businesses and both of their parents are successful entrepreneurs. Am I surprised? Hardly.

One of the reasons I think this might be true, at least in my case, is that when my children were growing up, I...Read More

the notebook

Sun, 31 Aug 2025 12:16:11 -0700

My father and paternal grandmother died of Alzheimer's disease. My eldest Aunt on my mother's side left the earth in a highly demented state. All three were in their 90s when they passed. I have no other significant disease pathways on either side of my family history, but I do have a significant risk of losing my mind with my body otherwise intact. A genetic test confirmed that I carry the APOE 34 gene variant–the one that sentences me to an elevated risk of manifesting severe cognitive decline. This is not good news for someone who uses so much of his brain to earn a living.

•••

One of the first and most successful of the Nicholas Sparks novels to become a feature film is The Notebook. The story intertwines the journey of a young couple who meet and fall in love one summer following the war with that of two much older people in the present day living in an assisted care facility. The latter day gentleman spends the afternoons reading a story about the younger couple to a lady at the home for whom he clearly has great affection. She appears not to know the identity of the strange man who reads to her everyday. At the end of the movie (spoiler alert), we find out that she has severe Alzheimer's and that the story is their story. She wrote it down in a notebook before she slipped away. He would read it to her and she would come back to him, if only for minutes at a time. Such is the devotion of true love.

•••

This year has seen a frenzy of activity and conversation about Artificial Intelligence. Generative AI companies dominate the capital markets, several big firms have launched new version of their LLMs (large language models) and companies are scrambling to build and implement...Read More

dispatch from the other side

Wed, 29 Jan 2025 08:40:42 -0800

Avalanche! It's the one thing a backcountry skier never wants to hear his guide yell. Our group had just finished the long first run of the day–a sweeping meandering path intended to carefully sidestep key trigger points on the high alpine slope. We were at the bottom ready to head back up when Tania heard something from above. A small wind slab had kicked off from the summit ridge. It looked quite small from where we stood and was well left of where we had skied down. I assumed it was a small size two that would have a short run out. I couldn't have been more wrong. The next thing we saw was a massive wall of snow exploding into the sky as the avalanche jumped a ridge onto a path heading directly toward us. It was quickly gaining volume and speed. Our guide said it looked like a size four and we knew an avalanche that big would be large enough to run to the valley floor below us and decimate the forest on its way down.

He yelled for all of us to run to the forest about 20 metres away. It was the only option. We were tripping and falling in the waist deep snow, getting snagged in the snow alder below our feet. I kept looking up while I desperately thrashed my way through. The avalanche had jumped another ridge. It was getting bigger, moving faster and getting closer. I've always known that a day would come where the mystery of my death would be revealed. As a climber and skier with forty plus years in the mountains, I've had my share of near death experiences and close calls, but I'd never been certain of my impending demise until this moment. I thought I was done, that this was it: the end of the road. We all managed to make it into the trees and waited for a crushing final blow that never came.

For several months before the trip I had an ominous foreboding feeling that I was going to get buried under the massive weight of avalanche debris, that I was going to get an opportunity to face my...Read More

eyes wide open

Fri, 05 Jan 2024 18:11:06 -0800

If we don't hear the whispers, we get hit by the screams.

I felt the snow pack settle weirdly under my skis as I arced an otherwise very satisfying full compression turn through the soft powder. I exited the steep gulley and skied to the creek bed where the guide was waiting for me. Half expecting a compliment on the elegant turns I had just made, he only said, "I've got eyes on her"...

Little did I know that, just as I was finishing my own stellar run, my bride was fighting for her life. She had triggered a sizeable slab avalanche that had run to ground, taking her for a terrifying ride to the bottom of the gully. I turned to look back up the slope and all I could see was the bright red of the air bag she had deployed from her avi pack at some point in the run. I had no time to freak out. By the time I was aware of the event, I already knew she had survived. I had no idea how close she had come...

Good judgement comes from experience which is often the result of bad judgement.

I started wandering into avalanche terrain at 19 years old, in my first season of ice climbing. For the first few seasons, I put no thought whatsoever into the risks I was taking. I was climbing frozen waterfalls in gullies that had formed underneath massive snow slopes, blissfully unaware that they were dying to funnel their violent snow masses on top of me and my partners, and sweep us away.

With every season that I miraculously survived, the more horror stories I heard. Famous climbers were getting bombed to their deaths or triggering their own slides into oblivion. Amateurs and experts, dilettants and professionals: the mountain took them all. Read More