About 25 years ago, before Kate and I were even married, I was working for a company based in Miami Beach. I was young, ambitious, and had it all planned out. The goal was to ride the wave of this company going public. I had stock. I had options. I had confidence. We were planning to get married, start a life together, and everything was looking up.
Then, one day, I got the call.
The company was going under. I was told I could take 10 cents on the dollar for my contract, the stock was worthless, they were closing the doors—and if I could sell anything left in the office, I could keep what I made.
The end result? About 25 grand.
So what do two young, not-yet-married, wine-drinking dreamers with no jobs, no kids, and no clue what comes next do?
We spent it all.
On a Butterfield & Robinson biking trip through Burgundy and Bordeaux.
We figured if we were going to hit reset, we might as well do it riding through vineyards, drinking wine, eating cheese, and figuring it out together.
And I’ll tell you this: It was one of the best decisions we’ve ever made.
We were the youngest people on that trip by at least 20 years. But we were treated like royalty. Butterfield & Robinson took care of everything. The food, the routes, the bikes, the support, the culture, the service—it was the first time I truly understood what luxury meant. Not in a flashy way, but in a thoughtful, curated, soul-replenishing kind of way. That experience stuck with us.
Now, 25 years later, we’re coming up on our 25th wedding anniversary.
And as I started thinking about how to honor that, how to reflect back and also look forward, I kept coming back to that trip. To Butterfield & Robinson. To that feeling of connection, adventure, and presence. This time, the trip might look a little different—maybe just the two of us again. Maybe a couples’ trip where other midlife men do something special for their wives and join us. Maybe a family trip—we’ve got boys now, 18 and 22.
I even want to host an all-guys Midlife Male trip where we get back on the bike, out into the world, and experience something epic together.
So I reached out to Butterfield & Robinson to share that story and to talk about collaborating. To let them know how much that one trip meant—and how much the idea of that trip still resonates today. Fortunately, they were kind enough to connect me with their CEO, Mike Scarola.
And that brings us here.
Mike’s background is extraordinary. He competed in the 2004 Summer Games in Athens as a sprint canoeist for Canada. He’s traveled the world as an elite athlete, and now leads the world’s premier active luxury travel company. Today, he’s logging 3,000 kilometers a year on his bike and over 120,000 kilometers in the air. He’s gone from Olympic athlete to investment banker to CEO—and he’s still chasing excellence, just in a different arena.
In our conversation, Mike shares the discipline of elite sport, how travel can change your life, and how Butterfield & Robinson continues to redefine what active, luxury travel means—especially for men like us in midlife, who are looking to move, connect, and live fully.
Let’s get into it.
Focus on Meaningful Moments:
“Quality’s everything… How many memories stick? Just the impactful ones. Make time with family and friends count by being fully present.”
Invest in Experiences:
“Post-COVID, our travelers—most comfy financially—didn’t need another Porsche or boat. They craved family time, unforgettable trips. Spend on memories that outlast material possessions.”
Plan for Lasting Impact:
“Every minute, day, or trip has got to be meticulously planned and executed. Organize your time to create meaningful, high-quality experiences.”
Stay Hands-On in Your Work:
“I guide a trip yearly… hands in the sand, feet in the ocean—it’s essential. Stay engaged in the details of what you love, no matter your role.”
Find Joy in Serving Others:
“Build fulfillment by creating positive moments for those around you.”
Embrace Active Living:
“Guiding people through a new place on two wheels at their pace. Beats a bus or car. Incorporate physical activity into your routines for deeper engagement.”
Simplify to Reduce Stress:
“Guides are our superpower… They make it seamless. If a restaurant closes at the last minute, they pivot. Delegate logistics to focus on what truly matters.”
Pursue Work You Love:
“The key is being happy with what you do. It took me time to figure out. Seek a career that aligns with your passions for greater satisfaction.”
Balance Effort and Energy:
“Work less than banking’s 100-hour weeks. I’m an owner and I still grind, but I’ll never stop. Just shift energy. Work hard but redirect energy to what fulfills you.”
Build Strong Connections:
“Friendships spark fast… Two couples met, they hit it off, have done 12 trips together since and now co-own a French winery. Surround yourself with like-minded people to foster lasting bonds.”
Plan for the Future:
“Our travelers plan beyond the next trip, often three or five years out… They execute with a plan. Map out long-term goals to align your life with your priorities.”
Stay Open to New Paths:
“Be ready to seize unexpected opportunities in your career.”
Use Skills Across Fields:
“I took my corporate skills, organization and direction, and mixed it with their travel expertise. Apply your expertise to new ventures for success.”
Value Time Above All:
“For our travelers, time’s their most valuable resource—not money.
Prioritize how you spend your time to maximize life’s value.”
Be Present for Loved Ones:
“I’m way better at being present with the kids now… Running an experience-focused business hammers home how powerful quality time is. Show up fully for your family to create lasting memories.”
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To learn more about Mike’s company, Butterfield & Robinson, and their trips, visit https://www.butterfield.com/
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Greg Scheinman
Founder, Midlife Male
52. Husband. Father. Entrepreneur. Coach
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