Andrew Penny

Market Strategy

Who Tells You You're Wrong?

Andrew Penny, October 20 2026

One of my early startup clients had good success selling software to boutique retailers in Eastern Canada. They had an excellent product and earned incredible customer loyalty. To expand, they planned to sell to a wider range of retailers, such as hardware stores, convenience stores and so on. The whole team was gearing up for the sales

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Leadership & Management

Crazy or Stupid

Andrew Penny, October 6 2026

Some days it seems we have an overabundance of stupid in the world. But we seldom ask whether we have enough crazy. During my expedition to Tuktoyaktuk, I received quite a bit of social commentary suggesting that what I was doing was stupid. You know: a 58-year-old British sports car. 15,000 km to the Arctic and back. What could possibly go...

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Leadership & Management

Tuk R Bust - 15,000 km in a 58-Year-Old British Sports Car

Andrew Penny, September 15 2026

I recently drove to Tuktoyaktuk and back. That’s about 15,000 km. In a 58-year-old British sports car. There was some crazy driving. Some “interesting” hotels, inns and B&Bs. Wonderful people. And scenery that was, quite simply, mind blowing. And Canada.

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Leadership & Management

Tuk R Bust - A Dispatch from the Arctic Ocean

Andrew Penny, September 1 2026

Two weeks ago, I mentioned that I was heading out on a little road trip. The destination is Tuktoyaktuk - “Tuk” - about 7,000 km from my home in Ottawa and, quite literally, the end of the road. It sits on the Arctic Ocean at the end of Canada’s northernmost public road. And just to make things interesting, I decided to drive there in my 1968

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Leadership & Management

Tuk Tea - The Benefits of Steeping

Andrew Penny, August 25 2026

As I mentioned last week , I’m currently on a slightly crazy expedition from Ottawa to Tuktoyaktuk. And I’m driving an antique MGB. What could possibly go wrong? Quite a lot, as it turns out.

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Leadership & Management

Tuk R Bust - Time to Start Driving

Andrew Penny, August 18 2026

By the time this is in your inbox, I’ll be on my way to Sault Ste. Marie - the first stop on our expedition to Tuktoyaktuk on the Arctic Ocean. It’s a 14,000-kilometre round trip in my 1968 MGB convertible. And what blows most people’s minds is that Edmonton is only ½ way. And somewhere along the way, the expedition became a bit of a convoy: me,...

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Market Strategy

Underwear, Buyer’s Remorse, and Keeping the Good Vibes Going

Andrew Penny, August 4 2026

Most of us wear underwear. We don’t think too much about it. Then, every once in a while, you decide to try something new. For several weeks, I had been seeing ads for Manmade underwear. Think of it as something like a bra for men—but, you know, ‘down there’.

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Leadership & Management

Tuk R Bust

Andrew Penny, July 21 2026

For me, Tuktoyaktuk  was one of those strange place names that sounds sort of familiar but I couldn’t place on a map. That changed recently. Let me back up a bit. Every year I try to do something that I really don’t know if I can do. One year I took singing lessons and performed in a recital (OK, it was me and three judgmental 10 year olds – but...

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Leadership & Management

Canada at 159

Andrew Penny, July 7 2026

Canada’s progress has been imperfect, uneven, and often slow — but slow steady progress compounded over 159 years becomes something wonderful. Canada’s quiet brilliance is not that it is perfect. It is that it has built a durable brand around trust, stability, resilience, humility, and usefulness. For a small country of just 41 million, and...

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Market Strategy

What sets Off Your 'Squirrel-Alarm'?

Andrew Penny, June 23 2026

I stopped into a local bagel shop recently for a coffee and breakfast bagel after my morning swim. I’d been there a few months earlier and hadn’t had a great experience, but I gave them the benefit of the doubt. Everyone has an off day. Surely they’d have sorted things out by

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