📝 All Articles

The Obvious Prediction Is Often Wildly Wrong

March 4, 2026

“Travel agencies are dead” — everyone, 2004. They set an all-time revenue record. In 2024. “AI will replace...

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Tiny

January 14, 2026

Andrew Wilkinson and I built Tiny together. There’s a lot online about the company, but I wanted to...

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Distinguished Entrepreneur of the Year Award

July 2, 2025

Last month, Andrew Wilkinson and I were honored by the Gustavson School of Business at the University of...

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The Problem with Perfect Advice: Why Stories Beat Suggestions

June 18, 2025

Some of my worst decisions in life and business came after asking smart, well-meaning mentors for advice. They...

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HoldCo Builders Podcast: Capital, Deals, and Lessons Learned

May 30, 2025

I recently had the pleasure of joining the HoldCo Builders podcast for a conversation. We covered a lot...

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Building Tiny: Our Journey to DEYA Recognition

February 4, 2025

I was recently honored alongside Andrew Wilkinson as Distinguished Entrepreneurs of the Year by UVic’s Gustavson School of...

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Why Businesses Get Messy Over Time

November 1, 2024

I look at my neighbor’s abandoned garden and it hits me – this is exactly what happens to...

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Peter Cundill’s Tips for a Good Life

June 28, 2024

I recently came across Peter Cundill’s advice for living a good life, and I had to share it....

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My Talk at VALUExBRK 2024 with Guy Spier

May 24, 2024

I was invited by Guy Spier to speak at VALUExBRK 2024, an annual gathering of value investors held...

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The Power of Being Seen

November 10, 2023

I found myself at a bar during what had to be their busiest night ever. Through the chaos...

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My Feature on the My First Million Podcast

March 2, 2023

I was mentioned on the popular My First Million podcast, hosted by Shaan Puri and Sam Parr. While...

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