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The personality layer

The Omega Speedmaster X-33 is on my left wrist. Titanium case, ana-digital display, 52 grams on a leather strap worn thin at the edges. The client across the table has a Rolex Submariner, which tells me something. The CFO next to her has an Apple Watch, which tells me something else. Nobody talks about any of this; you don’t have to. Objects say things without needing permission.

I have been a strategist, a speaker, and a consultant long enough to know what clients actually buy: the judgment behind the slide deck. And judgment comes from somewhere. Mine comes, in part, from the things I keep, the things I drive, the books stacked on my desk, and the photographs I take in the early morning on a Congress Avenue sidewalk in Austin. This page exists because a strategist without a personality layer is just a methodology with shoes.

Why a strategist needs a personality layer

There is a version of the professional speaker who presents himself as distilled expertise: pure signal, no noise. Clean LinkedIn, press photos in a blazer, keynote titles that end in the word “transformation.” I understand the instinct.

It also feels like a brand that arrived from a template generator.

The consultants I have trusted most in my life carried their full selves into the room. One of them drove a 1973 Triumph Bonneville to client meetings and kept dog-eared copies of Frank Herbert’s Dune in his bag. That combination told you something real: this person reads long, builds to last, and has a relationship with friction. You could trust his risk assessment.

Pattern recognition is the core skill of strategy. You walk into a boardroom and read signals fast: the body language, the org chart on the whiteboard, the questions that don’t get asked. That skill doesn’t run only from 9 to 6. It lives or dies based on how much you practice it everywhere else.

Full stop. The objects you keep, the machines you drive, the books you absorb; all of that is pattern recognition training, running continuously in the background.

What you optimize for in your private life is what you actually optimize for. Everything else is stated preference. If I claim to care about craft but own nothing handmade, you should be skeptical. The Speedmaster X-33 on my wrist, the Porsche 911 SC in the garage, the battered paperback of Range on the nightstand: these are data. They say I value things built to outlast the moment of purchase.

This connects directly to the work I do with teams on AI as a strategic force and to the leadership frameworks I bring into boardrooms on leadership, communication, and organizational change. The humans who make better strategic calls are, almost always, the ones who keep making and breaking and paying attention to things that age well.

Watches: time, craft, and the long now

I never became an astronaut. At sixteen, an ophthalmologist and a stack of Ishihara plates grounded me: colorblind, mild but persistent, enough to close the door on pilot training and every NASA application I never sent. So I did the next logical thing and decided I would at least wear the instruments. The Omega Speedmaster X-33 on my wrist is the titanium, ana-digital mission computer that actual Artemis astronauts wear, not the polished Moonwatch that gets photographed in magazine spreads. Mine runs four time zones simultaneously and tracks elapsed time with a bezel that requires a fingernail and actual attention to operate.

The watch collection grew sideways over two decades: a Breitling Navitimer that requires circular slide rule math to use correctly; a U-BOAT dive watch that weighs approximately as much as a small anchor; a Seiko SKX007 that has been in the sea more times than I can count; chronographs, field watches, one gloriously impractical piece with a tachymeter I have never needed.

The common thread: mechanical movement or analog display. Objects that do their work through physics rather than software.

There is a reason I wear mechanical watches in strategy sessions and not a smartwatch, and it has nothing to do with status signaling. The reason is about pace. A mechanical watch is a commitment to a certain relationship with time: the time it takes to make something, the time it takes to learn how to use it, the maintenance interval, the repair cost when something breaks. An object that requires a 24-month waiting list and a watchmaker’s loupe to service makes you think differently about timescales.

And thinking about the long timescale is exactly what most boardrooms need more of.

In the X-33 post I wrote about Artemis II and the strange comfort of knowing that the same reference is strapped to every crew wrist on the way to the Moon. That piece surprised me with how much it said about ambition, about redirected longing, about the human habit of finding a proxy for the thing you wanted and couldn’t have. A CEO read it and hired me the following week for a keynote on long-range thinking. I do not think that was a coincidence.

Cars: physics, joy, and the analog argument

The petrolhead thing goes back to childhood. I was seven years old the first time I sat in something with a real engine, and I understood immediately that the relationship between input and output was direct, physical, and honest in a way that almost nothing else was. You pushed the pedal and the car went faster. You turned the wheel and felt the tires. There was no mediation. I have been chasing that feeling ever since, through a lot of cars and a few decades.

The fleet I ran during the exhibition chapter, documented on the exhibition cars page, included a Porsche 911 SC, a Lotus 7, a Land Rover Defender Lightweight, and a Toyota Land Cruiser. Less a collection than an argument in vehicles: different machines make different demands, and meeting those demands teaches you something. The 911 SC is from 1982 and has air-cooled rear traction and no electronic safety net; the Lotus 7 has a sub-500kg kerb weight and puts the driver roughly six inches from the road surface at speed.

Both reward attention and punish laziness.

I spent a year with a Polestar 2, which was a deliberate experiment in letting go of the combustion instinct. The car is excellent; the engineering is genuinely impressive; I gave it a fair verdict. What the Polestar taught me was that I could be rational about performance specifications and still feel the loss of something the numbers don’t capture. I wrote that piece in 2020, before I wrote Chronicle of a Death Foretold: This Petrolhead, which is about the same grief written more honestly. Rational and emotional sit in layers, not in opposition.

The MINI JCW post came out of the 100,000 Miles project: MINI Belgium dropped a Clubman John Cooper Works into the mix for a leg of the journey, and I wrote about the physics of a small, angry car on Belgian highway at 4 a.m. It bites. That is the right quality for a car. How long will cars still be cars? asked the question that was already obvious in 2019; the answer involves software, regulation, and the slow disappearance of the kind of driving that made me fall in love with cars in the first place.

The strategy-and-Lego connection I made in Strategy is like off-roading. And Lego. is the compact version: the pattern recognition you need in a strategic crisis is the same thing you practice when threading a narrow road in a light car with no traction control and a lot of opinions. You read the surface. You commit or you don’t.

Books: the operating system

I read the way some people drink coffee: compulsively, in variety, with strong opinions about quality, and genuinely difficult to be around when the supply runs low. The books I carry into boardrooms, or reference in presentations, or mention in client calls are the ones that rewired something.

Mustafa Suleyman’s The Coming Wave landed in 2024 and I have quoted it in more strategy sessions than any other book in the past two years. The argument is unsentimental: AI and synthetic biology are coming, the containment window is closing, and the people who tell you otherwise are selling something.

Frederic Laloux’s Reinventing Organisations is the book that most directly feeds the leadership and change work; it maps the evolution from hierarchical orange to purpose-driven teal with enough case material to make skeptical CFOs uncomfortable in useful ways. Priya Parker’s The Art of Gathering sounds like it’s about parties but is actually about the design of attention; every facilitator and every speaker should read it. Brian Solis’s Mindshift made me furious, which is Brian’s reliable mode of operation, and I wrote as much in the review.

Douglas Adams’s The Hitchhiker’s Guide to the Galaxy is the only book on this list I have read at least eight times. It survives re-reading because it is, underneath the comedy, a book about coping with systems too large and too absurd to understand. That is also a description of most organizations I consult for. David Epstein’s Range is the book I hand to any executive who tells me they need to specialize more aggressively; Epstein’s data on generalist advantage in complex systems is the best argument I know for the kind of cross-domain attention that the 100,000 Miles project is built on. Brian Solis’s Lifescale rounds out the shelf, asking you to be a creator rather than a consumer, which is the thing I keep returning to when I work with teams on what SXSW actually teaches.

What I read becomes the lens for what I see. That is the only way I know to explain why I picked up a signal at SXSW 2025 that three of my strategy clients had missed, even though all of us were sitting in the same conference rooms. Different lens. Different resolution.

Photography: the discipline of attention

I started shooting seriously at SXSW, because Austin is the best street-photography classroom I have found. The light on Sixth Street at 7 a.m., before the sessions start, before the crowd arrives; the faces of people who are about to hear something that will either confirm or destroy their current worldview. You have about a quarter-second to decide whether to raise the camera. You either see the shot or you don’t.

The Google Pixel is my field camera. A camera you have with you makes images that a camera in a bag does not. The Stargate session, the Pressure Cooker crowd, the street portraits in Charmageddon, the light in Dear Tara 9, the portrait work in Amy: these photographs are part of the reporting, not decoration on it. They are how I trained myself to see the room.

Photography taught me the thing that is hardest to teach in strategy work: attention before action. Most consultants arrive in a room and immediately start generating outputs. The photographer’s instinct is to slow down, to read the light, to wait. That pause is where most of the useful information lives.

The thread back to the work

Clients occasionally ask, with polite confusion, what watches have to do with AI strategy. The direct line: a person who pays attention to the engineering inside a 1962 Speedmaster movement, who notices the finishing on the mainspring, who cares whether the case back is correctly closed; that person brings a different quality of attention to the architecture review of an agentic AI system. The attention is the skill. The object just trained it.

The less direct answer is that people hire speakers and advisors partly for what they say and partly for who they are. When I stand in front of a board and talk about AI as a strategic force, they are reading me the same way I read watch choices in that first boardroom scene. They want to know if this person has skin in the game, a relationship with risk, an understanding of what it means to commit to something for the long term. The car history, the watch collection, the book habit, the photography practice: all of that is the answer to questions they are asking without asking them.

If you want to talk about any of this, the about page has the direct route, and the keynote speaker page covers what a working engagement looks like. The four other pillars on this site form the frame: AI and strategy, leadership and change, 100,000 Miles, and SXSW Chronicles. This one is the texture underneath all of them.

Further reading

Watches

Cars

Books

Photography

Frequently asked

Why does a strategy consultant collect mechanical watches?

The same quality that makes a watch worth keeping for fifty years is the same quality that makes an insight worth acting on: honest construction and the willingness to do the difficult thing properly rather than the convenient thing quickly. I wear every watch I own, and I expect each one to work.

What’s in your watch box right now?

The Omega Speedmaster X-33, worn daily; a Breitling Navitimer with a working circular slide rule dial; a U-BOAT Classico 46mm from a Geneva shop on an unreasonably good day; a Seiko SKX007 that has survived more water than I should admit. And one or two pieces bought for reasons I haven’t fully explained to myself.

What is your favorite car you’ve ever owned?

Honest answer: the Porsche 911 SC, 1982, air-cooled, rear-engine, no traction control, and absolutely no forgiveness for laziness. Also true: the Lotus 7, which is less a car than a rolling argument that everything unnecessary should be removed, and you should be fine with that.

Can clients book Heliade for events involving the exhibition cars?

The fleet on the exhibition cars page was assembled for a specific commercial chapter. If you’re curious about how those vehicles fit into event programming or brand experiences, the contact page is the right place to start. The cars are real, they work, and they have stories.

What books would you give a new VP of strategy?

Range by David Epstein first. Then The Coming Wave by Mustafa Suleyman, because anyone thinking about strategy without understanding what is about to arrive in the next three to five years is thinking about the wrong decade. Then Reinventing Organisations by Frederic Laloux, because most of what strategy fails to account for is the organization it has to move through.

Do you sell prints of your photography?

Currently, no. The photographs on this site are field documentation. Several have appeared in editorial contexts and in session-coverage pieces from SXSW. If you’re interested in a specific image, reach out via the contact page.

Do hobbies belong on a professional thought-leadership site?

This question contains a flawed premise. These practices produce the judgment that makes the work worth buying. A strategist who reads nothing, drives nothing interesting, and pays attention to no physical objects is a strategist running on recycled abstractions. I have met many of those. They are hard to distinguish from a well-configured chatbot.

What does the car and watch obsession have to do with AI strategy?

The capacity to read complex multi-component systems and their trade-offs is the same skill, applied to a mechanical movement or an AI architecture diagram. The petrolhead instinct toward analog physics, toward things that break in diagnosable ways, produces a useful skepticism about digital systems that claim to have no friction.

What is the 100,000 Miles project and how does it connect here?

100,000 Miles is a rolling book project: a year of deliberate travel to meet people, gather signals, and write. The cars that made sections of that journey possible are documented in those posts. The books I read on the road feed directly into the strategy and leadership work. Everything on this site connects to everything else, which is the point.

Is the SXSW photography professional quality or phone shots?

Mostly phone shots, specifically the Google Pixel. I have trained myself to see before I shoot, which is a different skill from being a professional photographer, and in some ways a more useful one.

You use the word “personality layer” in the page title. What does that mean exactly?

The human texture underneath the professional identity. Strategy without personality is a commodity. Personality without strategy is a blog. The combination is what makes someone worth hiring to stand in front of a board and say something true about where an organization is, where it’s going, and what it should stop pretending.

How do I engage you as a speaker or advisor?

The keynote speaker page has the current format options and engagement types. The about page covers the biography. For direct conversation, the contact form is the fastest path.

The watch is still ticking. The car is in the garage. The books are not going anywhere. Neither am I.