Insights, strategies, and stories for leaders ready to excel in every dimension of life.

You can’t work smarter until you do this…

After 30+ years and nine startups, I still get asked the same question: How do I work smarter? The truth most people don’t want to hear is—you can’t work smart until you’ve first do this.

The 1 Investment You CANNOT Afford Not To Make

Most of us aren’t really living in the present. We’re stuck replaying the past or racing ahead to the future — and missing the only moment we can actually live: right now. Here’s why that matters now more than ever.

Might Tariffs Be An Unexpected Gift For Your Business?

Tariffs, AI, and turbulence everywhere—business today feels like a perfect storm. But what if this isn’t the end of something… what if it’s the beginning of bold reinvention? In this newsletter, I unpack how past crises shaped my entrepreneurial journey, why adaptability is the new competitive edge, and how today’s disruptions might just be your greatest opportunity yet.

Winning the Wrong Way: The Most Expensive Kind of Success

You can win the game and still lose what matters most. I’ve lived through that tension—and it has forever changed how I define achievement and fulfillment.

The Lesson I Had to Learn the Hard Way (and Why You Don’t Have To)

Some lessons in life can only be learned the hard way. No matter how many warnings we receive, sometimes we simply have to live the experience ourselves to truly understand it. This is the story of one such lesson: a painful, humbling, and ultimately revealing experience on the potential perils of mixing business with friends and family.

The Product Recall That Could’ve Ruined Us—And Why It Didn’t

In 2011, a top-selling product from our toy company began failing in the market—creating safety concerns, reputational risk, and a make-or-break decision point. What followed became one of the most defining moments of my career: a reminder that values only matter if you’re willing to live by them when it’s costly.

The 4 traits of the best leader I have ever worked with.

I was privileged to work for a very intelligent, experienced and capable leader in my last corporate job, before moving on to my next career. Beyond his capability and smarts, he did these 4 things consistently. They not only made a huge difference to me at the time, they set a standard for the kind of leader I wanted to be.

Is Pleasure Distracting Us From Our Greater Purpose?

At this time of the year, I have been tuning into the NHL playoff’s expecting to watch some thrilling hockey games. But what caught my attention even more than the games is what is happening between the whistles: a series of ads that is revealing something deeper about our culture, our distractions, and what we’re really searching for.

Love Without Finish Lines: The Sacred (and terrifying) Dance of Vulnerability

The deepest desire in life isn’t to be admired—it’s to be understood. In this newsletter, I share what I’ve learned about cultivating Level 5 relationships—the kind rooted in vulnerability, trust, and the kind of love that doesn’t have a finish line, but keeps growing for a lifetime.

Don’t lie to yourself…it could happen to you

No one draws a line from where they are, to a ditch and says “that’s where I’m heading!” And yet, whenever we see someone who has blown up their business, their marriage or their reputation by one (or many) bad decisions, we may be tempted to tell ourselves the lie that it would never happen to us. Here’s a better truth to tell yourself.

More Than What You Do: Escaping the Identity Trap

I spent years trying to live into an identity—believing that doing hard things with excellence would finally prove I was enough. But it wasn’t until I paused to examine where my true purpose came from that I began to uncover a deeper, more lasting sense of fulfillment in my life.

The McLaren, the Merger, and the Myth of Arrival

What if the thing you thought would finally make you feel complete… didn’t? A fast car, a dream exit, a picture-perfect life—sometimes they reveal more than they resolve. In this week’s newsletter, I share the surprising truth a McLaren taught me about identity, arrival, and the story we tell ourselves about success.

Don’t Die At 25: Why Staying Hungry and Staying Foolish Is The Answer.

There’s something powerful about staying playful, curious, and open–even as we age and take on the weight of responsibility. In this week’s reflection, I share why I’ve come to see childlike wonder not as immaturity, but as a deep form of self discovery. And how staying “hungry and foolish” is a key ingredient to being fully alive.

The Best and Worst News: It’s Not About You

“Finding your purpose” is a worthy pursuit—but if it stays self-centered, it will eventually break you or burn you out. True purpose isn’t about personal fulfillment; it’s about love—living in a way that benefits others. When you shift from asking “What’s in it for me?” to “Who am I here to serve?”, everything changes.

The Mountain, the Obstacle, and the View Beyond

The Final Stage Most Achievers Never Reach (But Desperately Need To)

I grew up the shortest kid in a family of giants and while no one teased me, I carried it as a quiet chip on my shoulder. That drive to prove myself fueled my work ethic, achievements, and pursuit of success, but eventually I realized that doing and having weren’t enough. In this week’s newsletter, I share the four stages of personal growth and why the final stage is where fulfillment truly lives.

Unsettling Lessons From Paradise: Discovering The Truth About Human Nature And Why It’s Important For Our Future.

At first glance, Saint Lucia felt like paradise; vibrant, lush, and seemingly untouched by the heaviness of a broken world. But beneath the beauty, I uncovered a story that challenged my assumptions about history, human nature, and the responsibility we each carry.

The Single best investment I ever made (And It Wasn’t the Markets)

Early on I made a financial move that most advisors would call reckless; cashing in my only savings as a broke college student. The reason? Let’s just say it involved a girl and a giant plush reindeer; a decision that would forever change the course of my life.

The One Thing You’ll Hold Onto in the End: A Story About Enough

We’re all chasing something. Learn how a powerful moment with my family and an Indiana Jones movie made me ask: Am I chasing the right thing?

Oasis, Rain, and Redemption: The Most Powerful Words We Can Speak

Most of us know what it means to build something great. But what happens when what you’ve built breaks; and the deeper work is learning how to rebuild trust and reconcile relationships? This is a story about rain, Oasis and the power of reconciliation

The Two Lists that dominate our thoughts (and why we might be spending too much time on the wrong one)

What if the things we obsess over are distractions from the actions that could actually heal us? Read on for a surprising insight about worry, guilt, and the unconscious pattern that keeps us stuc

“​​I’ve Made Hundreds of Millions… But I Still Don’t Know What My Life Is For.”

A wildly successful CEO confessed the above to me and with his honesty it forced me to reflect on how success without purpose can leave even the highest achievers feeling lost.

The Most Dangerous Financial Addiction No One Talks About

Most people chase financial success believing it will bring freedom; but many find themselves feeling more trapped than ever. In this article, I unpack the hidden shift that turns money from a life-giving tool into something that is soul-draining; and how to take our power back.

The Superpower nobody wants, but everybody has (that works wonders when we use it)

North American culture celebrates strength, success, aptitude, control and capability. What's more, if we're honest, these are all things we gravitate to as individuals. But what if true power was embracing the opposite of these things? Read on to find out about something we don't instinctively want but all have and can use in our lives.

Why Time is Unforgiving: Lessons From Tetris Part 3

I've spent countless hours playing Tetris since it launched in 1989. Only now do I see what the game was trying to teach me all along; profound truths about life, timing, and the regrets we create when we get the order wrong. This week I will reveal the third and final lesson that Tetris can teach us about how to live a fulfilling life.

Why Many Opportunities Have An Expiration Date: Lessons From Tetris Part 2

I've spent countless hours playing Tetris since it launched in 1989. Only now do I see what the game was trying to teach me all along; profound truths about life, timing, and the regrets we create when we get the order wrong. This week I will reveal the second of 3 lessons that Tetris can teach us about how to live a fulfilling life.

The Trap Found In The Game That Successful People Play

A quiet conversation on a beach with a close friend led me to rethink something I’d believed for years about success and the people we surround ourselves with. This week's newsletter explores the subtle game many ambitious people are unconsciously playing, preventing them from living a truly wealthy life.

How You Can Be Rich But Not Wealthy, If You’re Missing This Currency

I recently read a quote from Warren Buffett that stopped me cold. It wasn’t about money or investing; it was about how we measure a life well-lived. It made me reflect on a few impromptu trips I’ve taken with my wife and kids and the reminder that some of the most important decisions we make aren’t about investing or work.

What a Quiet Morning in Bed Taught Me About the Wealth I Almost Missed

Why I Quit Social Media And How I Came Back Different

What happens when the platforms we use to connect start quietly disconnecting us? In 2018, I stepped away from social media to reset. This newsletter unpacks why I left, what I learned, what brought me back, and what is different about my return.

From Imposter To Inner Ally: How I Rebuilt My Confidence by Keeping One Simple Promise to Myself

Recently, my son wrote a piece that struck a deep chord with many in our community. The response was powerful, so I invited him to share again; this time, a more personal story about navigating self-doubt and rebuilding trust with yourself. I believe his reflections will resonate with anyone on the path from striving to truly thriving.

Why Setting And Achieving Goals Won't Make You Happy (Without These 3 Essential Ingredients)

Have you ever achieved something big, only to feel surprisingly empty afterward? In this week’s newsletter, I reflect on a powerful lesson sparked by an old journal, a set of long-forgotten goals, and a quiet realization about the real definition of an ideal life.

What If the Best Return Isn’t on Investment, But on Experience?

This week, my son shares a perspective shaped by a backcountry ski trip with founders and families in British Columbia. What began as an adventure turned into a reflection on how we measure success, challenging how we think about returns.

How Life After New Years Resolutions Often Feels Off (And What a Wobbly Stool Can Teach Us About Why)

We are taught to plan and track our health and our wealth with religious fervor, yet we rarely apply that same discipline to the one thing that gives those assets meaning. I have seen founders reach every milestone only to realize they were building on an unstable structure. Read on to discover the three pillars required for a life that is not just successful, but structurally sound.

Be a Loser in 2026 (trust me, everyone will thank you for it)

No one likely has a plan to lose in the year ahead, unless it’s weight. We all want to win, succeed, achieve or master. But there is something that if you planned to lose it, and succeeded, it would be a huge win for the people around you, and ultimately for you as well.

The One Asset You Can’t Recover (And the Jar We All Will Fill)

As the year begins to race toward the holidays, most of us speed up. I’ve learned to do the opposite. This week's newsletter is about reflection and slowing down long enough to make sure we’re filling our lives with what actually matters before the busyness of life crowds it out.

Why The Right Idea At The Wrong Time Is The Wrong Idea

Most founders talk about grit, hustle, and execution but few talk about timing. The truth is, even with the right team, strategy, and effort, if your idea arrives before the market is ready, it won’t matter. In this newsletter, I explore why success often hinges less on how hard you push and more on whether you’re positioned to catch the wave.

When Winners Should Quit (And Why That’s Not Failure)

We’re told winners never quit; but what if that’s the lie that’s holding us back? In this week’s newsletter, I share the story of how walking away from a sinking business might be the right call and while quitting might be the right thing to do.

The Day I Got Fired From My Company And Finding What I Was Missing

In 2017, I was fired from a company that I co-founded, and in that painful disruption, I received one of the greatest gifts of my life. This is a story about time, regret, redesign, and the sacred math that determines what will really matter in the end.

Are Goals Driving Growth Or Stealing Our Joy: Why Setting Goals Can Make Us Miserable

I’ve spent most of my life goal-setting, achieving, and immediately moving on to the next thing. But a moment in Nepal and a forgotten journal forced me to ask: What if all this striving is keeping me from the very joy I’m chasing?

The Final Lesson: What My Dying Father Taught Me About How To Live.

Three years ago, I sat in a hospital room reading aloud to my father as he lay in a coma.The book was Fathered by God by John Eldredge. We had been reading it together for weeks, sharing insights about the stages of a man's life. But now, as I read the final chapters to him, I knew these would be the last words we would share.As long as I can remember, my dad loved to read; I did not. At least not at first, as when I would sit down with a book, my scattered mind would wander. It was an acquired discipline, modelled by my father who would often say, "Readers are leaders.” My dad was my hero. The person I turned to when life got messy or business got complicated. He had this way of cutting through the noise with deep wisdom that brought clarity to the chaos. He was a guide who helped provide direction; as he was doing in the photo above with him and my son. Now, as his life was ending, I was learning one final lesson from him

Empowering others is a nice idea…until you actually have to do it.

Empowering leadership isn’t just about delegation—it’s about surrendering control, embracing uncertainty, and prioritizing others’ growth over your own comfort or image. True empowerment demands humility, patience, and the courage to let others decide—even when outcomes differ from your own instincts. Strong leaders build strength by letting go.

The True Cost of Capital: What I Learned After Saying Yes to Venture Funding

After decades of bootstrapping, I took venture capital for the first time, and everything changed. I learned that money doesn’t fix problems; it magnifies them. Fast growth looks exciting, but strong, disciplined growth endures. The real question: are you building something fat or something strong?

3 Lessons Tetris and Life Have in Common (And Why They Matter Now)

A timeless lesson from Tetris: life’s pieces don’t always fit the way we want. We can’t control what comes next, only how we respond. Every challenge, setback, or unexpected “block” is an opportunity to build with wisdom, resilience, and purpose, one move at a time.