A conversation with Will Fuentes, Maestro Group’s founder, on getting off life’s roller coaster—and getting on track for the financial future you want.
February 07, 2024
As a 17-year-old kid, working at a butcher shop in Springfield, Virginia, Will Fuentes recognized that he was outperforming his coworkers. He asked for another dollar an hour in wages and threatened to quit otherwise. The butcher was unmoved. Go ahead, he was told, this shop won’t close because you leave.
Fuentes regrouped and sought what he really wanted, which was to feel like part of the team. He soon found himself getting invitations to dinner and tickets to local games—the small but meaningful gestures of camaraderie he’d prematurely envied. He worked at the butcher shop for another five years, and periodically returned to help for another three years beyond that. “You need to figure out the employees that want to stay with you because they enjoy the work,” the butcher, now a friend, explained to him years later. “Then value them like you should.”
When Fuentes retells this story, he contrasts the person for whom another dollar an hour could have addressed a particular pain point (“Well, now I can pay my electric bill”) versus someone who, like him, was asking out of restlessness and looking for validation. If you fall into the latter category, there will always be another dollar, another ask. “Money isn’t going to appease you for too long a time if you’re unhappy where you work,” he reflects.
This wasn’t Fuentes’ singular, transformational experience. Nor was realizing that he wasn’t passionate about the drudgery of the day-to-day practice of law for a young associate—and getting a job at Best Buy instead (though that was where he met future start-up partner Michael Valade). Even a life-threatening car accident at age 28 that broke his back and hip, and left glass embedded in his scalp, was only part of his journey. He came out of the hospital with a resolution to embrace opportunities, but unsure what that looked like.
“I didn’t understand that just having the energy to accomplish something is not the same as having the stamina, determination, and consistency to do it,” he remembers. For some time, “my life continued to be a rollercoaster of ups and downs.”
If you draw a rollercoaster, what you get is a bell curve. As he puts it in our conversation, Fuentes has lived on both sides of the bell curve. He recognizes his advantages—intelligence, a capacity to do in three hours what might take someone else eight hours, an ability to dust himself off, and a family tradition of resilience. Yet he owns his many experiences with not just falling short, but failing big.
“Ability is just a leg up,” he says. “No matter how talented you are, you have to work hard and push yourself. Otherwise, you’ll get mediocre results. Maybe not relative to the world, but relative to yourself and your talent.”
“We’re figuring out how to help people communicate better,” Fuentes observes. He delights in watching a client’s team elevate their professionalism thanks to Maestro’s trainings. “They’re starting to use the three times, to follow up; they’re taking lots of notes; they’re asking bold and tough questions. They’re getting answers from people, which normally would have taken a month, in days or weeks.”
Fuentes compares improving the full range of one’s sales skills to the relative tedium of refining your left-hand basketball dribble, or your defensive stance, versus the crowd-pleasing satisfaction of perfecting your jump shot. The foundations are a foundation for a reason, and you have to be “strong in the boring.” (A phrase that might not catch on, admittedly, quite like “Go hard in the paint.”)
In advisory sessions, Fuentes speaks of reality as it is, versus how it has been or how it could be. Sometimes, he pushes back on plans by asking: “Sure, we can do that, but to what end? What’s the outcome that we can expect?” Founders often gravitate to decisions that favor optimism, even if 30 other circumstances must first fall into place for things to work out. Fuentes knows people are often driven by emotion, with a little bit of logic. He stays loyal to logic.
“If you couldn’t pay your electric bill because you have to continue to employ someone,” he says, playing out the brutal questions that can be part of his job, “would you still employ them?”
Earlier, Fuentes could imagine himself as the employee who asks for a raise because he’s worried about paying his electric bill. But he’s also watching out for the sales leader making difficult calls in order to keep the lights on at his business. He gets being a 20-something scrounging for change to cover the gas so he can go out with friends, and empathizes when that’s the only option. He’s also the father who challenges his son to not turn out to be that guy.
When I took the phone call that led to me joining Maestro Group, I was standing in the waiting room of an Intensive Care Unit. I mention that not to overshare, but to drive home that Fuentes’ mantra, “My mission in life is to change people’s financial futures by teaching them the things that I know how to do well,” came to my ears in a crisis moment.
When I ask Fuentes for an example of how people’s lives can be changed, his answer is rooted in a personal memory. His mother, recovering from severe illness, hospitalization, and time in a rehabilitation center, wanted to return to her house. But her bedroom was up an inaccessible flight of stairs. The only options were for her to relocate, uncomfortably, to the basement—or to get a mechanized chair lift.
Fuentes was able to reply to his father’s estimate of the lift’s cost by saying, “Call them. Tell them to do it tomorrow, rush job, so we can take her home. I got it.” When he contrasts being able to say this, versus the twenty-something version of himself who might have been helpless to do more, his body posture changes. He stands taller.
“I don’t want you to ever have to go through that,” he tells clients, “But I want you to be in a position where, if you have to go through that, it’s not even a question.” What empowers people is improving not only their own lives, but those around them. He reels off the wins reported by clients who were able to make dreams happen because of higher sales: a first house, paying their kids’ college tuition, a long-dreamed-of vacation to the Mediterranean.
Fuentes uses the phrase “big, hairy, audacious goal” twice before I’m confident that I’ve heard correctly. He’s describing his practical desire to retire by age 50 (though the exact definition of “retire” is subject to revision). Fuentes’ use of this memorably weird phrase, along with his belief that every sales team should share recommendations of newsletters, books, articles, and podcasts—what might be called, in another context, a “common read”—reinforces my appreciation that he is deeply engaged with words. Sales sometimes gets a bad rap for abusing language, but a great sales professional enjoys the art of conversation.
“I love the human element way more than the business element,” Fuentes says about his work. He delights in people’s stories of how they came to be who they are. I hear it in the way he slows down in coaching sessions to genuinely listen to those stories, which is remarkable for someone who, by all accounts, moves at a faster speed than the rest of us. When I ask him what time of day he finds most difficult, thinking he’ll mention a particularly early or late hour, he answers, “any time that I don’t have a task.” He’s a steadfast believer in time blocking.
Fuentes holds a law degree from George Washington University and a bachelor’s degree in international relations from Virginia Tech, and he is a graduate of Thomas Jefferson High for Science and Technology. I mention TJHSST because, as one of the country’s top public magnet schools, it tends to shape the people who go there. Being smart is just the starting place. You also need discipline (or, if not, raw survival instincts), and you’re usually open to ingesting massive amounts of caffeine. There’s a sense that anything is possible.
Back in his days after law school, while debating whether to move to California to act, Fuentes tried stand-up comedy. He approached the challenge in the manner of a TJHSST kid: by studying countless hours of comedy, identifying different rhythms, finding the one that best matched his own voice, then plugging in his own ideas. Success at a couple of open mics led to his first paying gig, “Not because I was funny, but because there is a science to joke telling.”
Yet when he worked to vary his set list of jokes for additional gigs, the performance got worse and worse, “to the point of almost zero laughs the last time I did it.” Fuentes was discovering a lesson that he brought to Maestro Group: when there’s a science to something, there’s probably an art to it as well. In forcing himself to systematically switch up his set’s voice, he’d drifted from any authentic connection to the material. The audience could tell, and so they stopped responding.
When Fuentes recounts his life, he talks as much about what didn’t work out as about what did. All the false starts. All the hard-won knowledge. In the multiverse, there’s a lot of different Wills. But in this universe, Will Fuentes ended up exactly where he was meant to be.
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