Caleb Fenner
From Competitive Swimming to Real Estate Success

Caleb’s path to becoming one of Mountain View’s top real estate agents wasn’t a straight line — it was built on years of discipline, determination, and an unwavering work ethic honed through his early career as a competitive swimmer and elite coach.
Growing up in Oregon, Caleb was surrounded by the real estate industry from a young age. His grandfather and father were among the largest residential developers in southern Oregon, and his family ran a successful real estate and property management company. While in high school, he co-founded a property management company with his aunt, which has since become the most successful in the state. However, Caleb was intent on carving his own path in life.
Rather than staying in the family business, he pursued his passion for swimming, earning a college scholarship and going on to become the captain of his university’s team. Elite swim coaching soon followed, taking him from Oregon State to Huntington Beach, where he apprenticed under an Olympic swim coach, and then to the University of Arizona, where he worked with some of the world’s best athletes. His expertise led him to coach at country clubs, which transitioned into country club management, and eventually, managing subdivisions and neighborhoods in Palo Alto.
As he transitioned into property management, the leap to real estate sales felt natural. He began part-time, balancing his growing real estate career with coaching and club management. But it wasn’t long before he saw the potential and decided to fully commit to the industry. Now at Compass, he has quickly climbed the ranks, becoming the #2 agent in both volume and transactions in Mountain View last year — all without a team behind him.
“I had a lot of connections through swimming. Being an athlete and coach also teaches you the discipline that’s needed to be successful in real estate, so that was really helpful when I switched to real estate full-time.”
The secret to his success is his relentless work ethic. Caleb wakes up at 3 a.m. daily, does a two-hour workout, and is in the office by 5:30 or 6 a.m. His competitive swimming background instilled in him the discipline required to excel, from grueling 5 a.m. practices to maintaining peak performance under pressure. That same mindset now drives his approach to real estate. In the early days, he threw himself into every possible avenue to grow his business — knocking on 1,000 doors a week, hosting multiple open houses, and absorbing as much knowledge as he could from top agents.
“A lot of my coaching was teaching self-discipline. In high-level swimming you have 12-13 practices a week, with 4 of those starting at 5 am. So I’m very dedicated. I think my motivation, determination, and discipline got me where I am now.”
“A lot of my coaching was teaching self-discipline. In high-level swimming you have 12-13 practices a week, with 4 of those starting at 5 am. So I’m very dedicated. I think my motivation, determination, and discipline got me where I am now.”
One of his biggest strengths is his ability to understand people, a skill refined over years of coaching. Just as every athlete has different needs, so does every client. Whether they require guidance every step of the way or prefer a more hands-off approach, he adapts his strategy to fit their personality and goals.
Now, with a strong foundation in place, he’s focused on the next phase of growth. He recalls one elite swim coach who believed that sharing knowledge elevates the whole sport. “I take that approach in the industry, talking to as many high-producing agents that I can,” he says. His goal is to continue scaling his business, possibly by building a team and setting new benchmarks in Bay Area real estate.
Beyond real estate, Caleb starts each day at the gym before heading to the office. He’s also passionate about travel, typically taking his family to Mexico in the winter and Asia in the summer. Yet even in his downtime, he’s focused on improvement, whether through real estate education, coaching programs, or networking with top producers.
“I spend a lot of time diving into real estate education, coaching, meeting with top producers… just trying to absorb everything I can to get to that next level.”`
“I spend a lot of time diving into real estate education, coaching, meeting with top producers… just trying to absorb everything I can to get to that next level.”`
In an industry where many hesitate to go the extra mile, Caleb’s tireless dedication sets him apart. He believes that success isn’t about luck — it’s about showing up every day, pushing forward even when things don’t go as planned, and constantly striving to be better.
“Even if you’re falling, fall forward and keep moving.”
With his unique blend of athletic discipline, strategic thinking, and an unshakable drive, Caleb isn’t just selling homes — he’s redefining what it means to be a top-performing agent in the Bay Area.