Big Sky Country: A Ride to Remember

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Big Sky Country: A Ride to Remember

I seem to say that every CEO Ride is memorable when done, and The CEO Ride Big Sky Country in September was no exception. This blog is delayed because as usual, I immediately jumped back into the day-to-day grind but managed to hold onto the jazz and perspective gained during this incredible week. Before everything’s too far in the rearview, I wanted to share my thoughts on a week that held a bit of everything. Here’s how it unfolded:


Each conference begins with an optional ride the day before official kickoff, as it’s where old friends renew acquaintances while greeting the new riders. On this particular day we were so focused on riding with each other that we didn’t even think about the forecasted 5 o’clock downpour of rain which sure enough, hit right on time. Turned out to be a preview to the coming week.

Once the whole group gathered and we’d caught up over great food and libations we looked at the weather and realized that rather than fit in our scheduled morning business session and get caught in more rain, we’d set off for Chico Hot Springs first thing. After getting a bit wet we checked into this hidden gem of a hotel you’d have to see to believe and immediately got down to business because after all, that’s the real reason we come together (OK, 50%). After a solid session we then retired to the Hot Springs that brought us there to relax and continue the conversation.

Red Lodge

The next morning’s forecast called for more flexibility where we decided to forego our traditional morning business session, leaving instead right away for the awesome town of Red Lodge. And we made it just in time too, before two days of rains came down with a vengeance. Since flexibility was the key of the week we elected to remain in Red Lodge and work on our businesses all day Wednesday, something we love equally as much as riding.

Where it rained on us, there was major snow in the elevations meaning the chances of our riding the legendary Beartooth Pass—the ride we’d all come to do—were slim. But the motorcycle gods rewarded our diligence of the day before and at 9:15, the Pass opened, allowing us to climb its 11,000 feet of amazing roadway and giving us a ride we’ll never forget.  


To say the anticipation and near miss was worth it would be an understatement. It was the true embodiment of the CEO Ride – working hard on our businesses balanced by pure, unadulterated riding that clears the mind and frees the soul.   

Our day-long ride then took us to Jackson Hole, Wyoming, through Yellowstone National Park where we were stopped by a bison herd blocking traffic. The immensity of those majestic animals and beauty of that place is mind blowing.

As we headed back to Bozeman and wrapped up the ride, one thing stuck out to me. No matter where we went, people wanted to know who we were and our story. We told them we were from Dublin, Toronto, Seattle, Boston, Denver, Connecticut, Montana and Florida.

The next question was always what brought us together, and how. The answer was always a simple one and the same – a shared passion for business and bikes.

Since lifting our kickstands on the first Inc. Ride seven years ago, that’s what the CEO Ride has always been about. Each time we gather, we not only get to experience a new, bucket-list ride, we get to gain new perspective on our businesses. For those who elect to come on subsequent rides (more often than not) that bond only deepens.

And that gets me excited about the future and more importantly, our 2020 rides, because though Big Sky Country was our best yet, The CEO Ride will only get better.

Interested in where we’re going? Stay tuned for the announcement soon, follow us on Facebook and LinkedIn or shoot me an email at and we can talk more about the CEO Ride experience.

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