BOULDER COUNTY Stewart Ward PROOF
SLEDGEHAMMERS, STARTUPS & SILENT RETREATS:
PROOF
“IN THE HEART OF EVERY GREAT REALTOR® IS A SERVANT.” – STEWARTWARD
Think real estate is easy? Think again. Just ask Stewart Ward, Associate Broker at Compass, who’s built a thriving business through grit, global perspective, and growth. There are no shortcuts to success. With twelve years under his belt as a licensed real estate professional—and many more flipping homes on the side—Stewart proves that success rarely comes easily.
From Tokyo Tech to Turning Houses
Before he found his calling as an agent, Stewart’s path took him across the globe.
“I always wanted to see the world,” he comments. After getting an English teaching certificate in California, he worked at a school in Thailand before moving to Japan. “I knew I had to become fluent in Japanese to land my first real job there.” “I studied Japanese full time, taught English to pay the rent, studied software and after a few years landed a job in investment banking technology at UBS in Tokyo.” He cut his teeth in fintech before transferring to New York and working in Manhattan.
“It was super boring compared to Tokyo,” says Stewart with a chuckle. “I had a team whose job was to audit new software for the trading floor of UBS in New York.” He applied for a job at a Silicon Valley startup, moved home to Miami, and worked remotely.
“That’s when I started flipping houses on the side and getting into real estate,” he reflects. “I try to stay open to the opportunities around me.”
“Eventually I was having more fun and making more money flipping houses than I was in corporate,” Stewart explains. “I was fortunate to have a successful exit from software right when the 2008 financial crisis hit so I took time off, reassessed, and eventually made the leap into real estate investment full-time.” He didn’t start on the retail side of real estate until 2013, after years of hands-on experience as an investor.
That leap wasn’t just about making money—it was about meaning. A partnership with an interior designer friend turned into a series of successful renovation projects in Florida. Stewart managed the research, finances, and contractors, while his partner handled the design. “It felt more like fun than work,” he reflects. “At least at first—until I realized wielding a sledgehammer wasn’t my calling.”
A Winding Road Home
Born and raised in Miami, Stewart’s early years were shaped by boarding school in New England and an English degree from CU Boulder, where he says with a laugh, “I mostly majored in having fun.” But Boulder left its mark. After living abroad for years he returned to Boulder in 2013 to start fresh.
PROOF
Starting over wasn’t easy.
“I arrived in Boulder after 20 years away, not knowing a soul,” Stewart shares. “I underestimated how competitive the landscape was.” Fortunately, his perseverance paid off.
He got to work—literally knocking on doors. Fifty doors and one hundred contacts a week was the goal. He pushed through those tough early years with
determination and savings, building his business from the ground up. “By year five, I was doing ok but thinking about quitting,” he admits. “Then someone recommended Ninja Selling. That changed everything. It reoriented me.”
Now, Stewart runs a relationship-based business rooted in systems and intention. “I realized I could have the business I wanted if I implemented processes and followed my natural desire to do my best.”
More Than a Broker
Stewart is passionate about building community and delivering storied service. He’s part of several meaningful circles, including fellow fans of Phish, a co-working space full of amazing people, and a spiritual community that keeps him grounded. He meditates daily and takes part in a one-week silent retreat once a year. “It’s a great reset,” he says. “It gives me perspective and reminds me not to take life so seriously.” In today’s hustle and bustle, it’s paramount to take time to unplug and recharge.
Stewart views real estate as more than a profession— it’s a personal mirror. “The biggest challenges I face in this business are my own internal hang-ups— limiting beliefs, past failures, self-doubt. Real estate helps me face those and let them go.” Real estate has helped Stewart focus on the world around him and make a difference while at the same time improving his business a little every day.
This high performer also uses real estate as an avenue for giving back and helping people through stressful times. Stewart currently sits on the boards of Growing Gardens and Vinnyitsia Sister City Foundation and introduces people to causes he cares deeply about. “It’s a big part of what drives me.”
Life in Boulder
While Stewart’s roots are in Florida, Boulder is home. He shares his life with his partner Eva and their little dog, Roxy. Though he comes from a big, loud, Type A family—“You could probably hear us at the dinner table down the block,” he jokes—he values solitude and quiet time to recharge. “I’m an extroverted introvert.” It’s both worlds for him.
When he’s not hustling, Stewart is on the slopes. “I’m obsessed with skiing,” he says. “I’ve done it since I was a kid.” He’s also a fan of gravel biking and soaking in Colorado’s outdoorsy lifestyle.
What Experience Has Taught Him
What advice would Stewart give to an up-andcoming agent?
“Have systems drive your day. Systems answer the question “what’s the most important thing to do right now?” when you’re new and you might not have transactions to work on. You need systems for every part of your business, especially keeping in touch with people.”
And finally, the quote that guides him, “I strive to add value to people’s lives wherever I can.”
At the end of the day, Stewart doesn’t just see real estate as a career, he sees it as a way to serve others in his community and make a positive impact in their lives.
I REALIZED I COULD HAVE THE BUSINESS I WANTED IF I IMPLEMENTED PROCESSES AND FOLLOWED MY NATURAL DESIRE TO DO MY BEST.”