Swimming Across Doubt

Another Founders Lesson…

Some of the most meaningful lessons come from real moments, ones that test your nerves, stretch your limits, and remind you what matters most.

This story is about one of those moments. A family swim, some nerves, and a reminder that action creates momentum.

⏳ Estimated Read Time: 6 minutes

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FOUNDER EDUCATION - Swimming Across the Lake

Every summer in Kelowna, hundreds of people take on the open-water swim across Okanagan Lake. The Across the Lake Swim has been going since 1949. It started as a rite of passage for local swim clubs and was part of the Kelowna Regatta.

Over time, it’s stayed competitive for many but it’s also turned into something families and friends do together.

We took on the 1.5 kilometer swim across Okanagan Lake. Paddlers line the route, and the whole thing has this mix of nerves, energy, and community.

Three years ago, I watched Ria do it. She swam with a few girlfriends who had done it before, and I remember being struck, by her accomplishment and the whole scene.

There were young families whose kids were doing it, too. That image stayed with me, we’ll get back to that.

The day before (even the morning of) we were on the fence of even doing it.

Ria and I both had moments of doubt. For her, it started with second-guessing.

Candidly the kids didn’t train much at all. Were we just teaching them about end goals, or did we want to teach them about preparation?

Ria told herself it was intuition, but talking to friends who’d done it, she realized it was a protective instinct dressed up as logic.

That distinction stuck with me. Fear disguises itself as intuition all the time.

But the truth is, most growth comes when you learn to tell the difference between the two. In this case, it meant getting in the water and going for it, even if the mind was trying to hold you back.

Regardless of all the mental battles, we finally jumped in the water. We swam it as a family. The kids are only 9 and 11, and they absolutely crushed it, even Ria’s mom killed it.

Meanwhile me at 45 was really quite nervous for myself. I had as much fear as they did. I was proud of myself for doing it, but I was more impressed by them.

The whole thing was meaningful. Even the little stuff like riding over in the bus at sunrise, Paisley and Ria singing to calm their nerves, the energy of community.

Then during the swim, realizing we were close to shore, laughing and kicking and knowing we were going to make it.

Those are the moments that last. But they wouldn’t have happened if we didn’t choose to face our nervousness head on.

What made it even more powerful was doing it side-by-side. That’s been a theme for us, whether it’s parenting, entrepreneurship, or pushing our limits. This wasn’t just a physical challenge. It was a shared moment. A memory. A marker.

It also created a ripple. Ria’s swim three years ago inspired her mom the year after. Then re-inspired Ria to train at it once again, which then inspired the kids and me.

And this year, our friends who cheered from the finish line said they’re doing it next year with their own kids. That ripple is true in a lot of things in life.

Doing is infectious: it effects your team, your network, and everyone around you.

It’s easy to relate this to entrepreneurship. You do the spreadsheets. You ask your mentors.

You analyze the upside and downside. But no one can make the decision for you. No one has your intuition, bravery, or gut.

That’s on you. You won’t always be right, and there won’t always be clarity. But courage counts.

Sometimes you do the math and still say no, only to watch someone else step in and build something incredible. Sometimes you push forward even when things don’t look perfect on paper, because it feels right. That’s the dance, between fear, data, intuition, and belief.

There’s a saying Ria reminded me of:

That’s how I felt about the swim. That’s how I’ve felt about a lot of things we’ve built over the years.

One bold act creates momentum. Whether it’s starting a business, jumping off a cliff, or swimming across a lake with your family. It doesn’t have to be big to matter. It just has to be yours.

Excavator slip and slides?

Old train car renovation into a luxury hotel?

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QUESTION AND ANSWER - From Gather ‘Round

Question: Is MBA school worth it?

Answer: Times have changed, but for me, MBA school was incredibly valuable. Not so much for the academics, even though I became a better managerial accountant and learned a lot about entrepreneurial finance. The real value came from the intangibles. It was the incubator effect for SAXX, the alumni network, the public speaking experience, and the relationship to China that I developed.

Looking back, it was more about learning how to think than what to think. The case method gave me a mental framework I still use today. So yes, MBA school is worth it, but only if you take full advantage of everything around it.

To this day, some of my best friends are from my MBA class. We take an annual trip together. I've invested in their companies, and they’ve invested in mine. If you’re smart enough, go to Ivey.

You also need a clear goal going in. If it’s advancing career quicker, if it’s incubating a business, if it’s shifting career goals, understand that beforehand.

And if you know what you want, look up the bios of the professors. Every school has its stars. Find the ones you want to learn from and make them part of your journey.