“You couldn’t borrow money to purchase a stick of gum.”
That’s how Kyle Stephenson remembers the Great Recession. He launched KRS Holdings in April 2007. If you’re keeping score at home, that’s right before the worst financial crisis since the Great Depression.
“I thought the world was coming to an end,” he says. It was “a really dark time in my life.”
Most business owners don’t get their first major economic crisis quite so early. “You just got to grind,” Kyle says. “You got to focus. You got to know what your goal is.” All of it, he says, takes “a little bit of patience, because if not, we quit.”
“And sometimes we quit too soon,” he says. “The light is right on the other side.” That doesn’t mean stubbornness is always the answer. “Sometimes it’s not a good idea and you punt,” he says. “But sometimes you just got to be a little bit patient, know that you’re right, going in the right direction.”
Leaving Medical Device Sales for Real Estate
Kyle spent the first part of his career in what he calls “corporate America,” selling medical devices. While he enjoyed the work, especially “making a positive difference in people’s lives through different procedures,” real estate had a stronger pull.
“My real true love has always been real estate,” he says.
He started buying investment properties on his own in the early 1990s and eventually reached a point where he had to decide whether it would remain a side pursuit or become something bigger. With help from a life coach, he made the call. He’d retire from medical devices, he says, “not because I had a tremendous amount of dough, but because I wanted to follow my love.”
He brought one idea from healthcare with him. In medicine, he saw a “multidisciplinary approach,” specialists working together on patient care. He wanted the same at KRS: someone “really good at finance,” someone “really good at maintenance,” and a hub, “someone that could really explain all of the different things and keep everything together” as a single point of contact for clients.
What KRS Does
KRS has offices in Richmond, Charlottesville, Lynchburg, Harrisonburg, Arlington, Hampton, and Virginia Beach, plus operations in Elizabeth City and Raleigh, North Carolina. When Kyle joined Virginia CEOs in 2015, KRS reported about $2.3 million in annual revenue. It’s since grown into what he calls an eight-figure company.
Beyond property management, KRS also invests directly in real estate. Employees can buy in, Kyle says, and KRS sometimes buys property and lets other investors participate alongside it. He has one line he uses in every pitch: “I believe real estate allows the average American to become financially independent and wealthy if you buy it right. So that’s my pitch.”
Kyle knows property management may not sound exciting at first glance. “It may sound a little dry, but I swear it’s exciting,” he says. That’s because no two days are the same. “There’s no easy button.” Whether it’s collecting rent or handling “an unfortunate fire or a sewer backup,” he says, “you gotta be on it.”
Building Leaders
“My role keeps evolving,” Kyle says, but right now his focus is leadership. “How do I make more people accountable? How do I really develop that leadership team?”
Every Tuesday, from 1:30 to 2:30, his direct reports meet virtually. Each presents on their department, then talks through the problems they’re having with their own team. His goal is for them to coach one another, not simply report upward.They’ve run the meeting for a couple of years.
As the company has grown, the stakes have risen. “Now we’re starting to buy companies,” Kyle says, and KRS plans to bring in a leader from outside the business. For leaders who aren’t developing, he asks what the company is doing “to coach them up or escort them out of the firm.”
Values get the same scrutiny. Kyle’s example is integrity. If a valuable employee “did something fraudulently,” he says, “you got to let that person go, or your company falls apart.”
For the planning behind it, Kyle calls himself “a monster Verne fan,” referring to Verne Harnish and his Rockefeller Habits framework. He keeps a box of Harnish’s books in his office and had a stack of Scaling Up materials on his desk during the interview. Every year, he works through it to decide “what I’m trying to achieve as a CEO.” Virginia CEOs has brought Harnish in to speak two or three times, and Kyle caught one of those talks at the Jefferson.
The Accomplishment He’s Most Proud Of
“I am so blessed,” Kyle says. He does it, he says, because “I love it and I don’t really need to do it anymore.”
“I love the fact that we have been able to change a lot of our employees’ lives,” he says. Some have “prospered beyond their wildest dreams” and gone on to help others. “I will tell you that is ridiculously fulfilling.” KRS once took 40 or 50 employees and their families to the Hard Rock in Punta Cana, Dominican Republic, for a team-building trip.
The work itself matters to him too.
“We get to touch people’s housing,” he says. “If we can provide clean, safe, affordable housing, you’re really allowing other individuals that work their tails off to come home and enjoy their families in a wonderful environment.”
Football, Business, and Perspective
Kyle played football at the University of Pennsylvania. He coaches at Freeman High School, and his son plays at the University of Richmond.
The conversation keeps returning to adversity. Living with a hundred young men is all-consuming, he says: “You don’t get any time. You’re excited if you get a day off.”
In his playing days, adversity often meant a coaching change, a recruiter leaving for another school. “This guy had my back,” Kyle says, “and how do I develop these other relationships?” For him, football became a lesson in relationships and how to handle adversity.
That mindset carried him through COVID. “We got a pretty nasty virus that’s shutting things down. How do we pivot?” he recalls. In moments like that, he says, “you need to be a leader… because everybody’s looking to you.”
He passes the same message to the players, and leaders, he coaches: “It’s never as great as it feels. It’s never as bad as it feels,” he tells them. “We got to keep going. We may have to pivot.”
Why Kyle Values His Virginia CEOs Roundtable
Kyle joined Virginia CEOs in 2015. His Roundtable meets monthly with eight or nine peers.
“It’s about relationships for me,” he says. The group helps him understand and appreciate different personalities. “I’m a football coach, right?” he says. “I think sometimes I’m a little different, a little bit quirkier.” He values the connections he’s built with “people that I may not otherwise run into.”
Traditional networking isn’t really his thing. “I don’t necessarily go out and do as much networking,” he says. “I can’t even tell you about networking events because it’s not really what I do.”
The Roundtable is different. “I’m locked in. I love that roundtable. I like the rhythm, right? Same thing as football practice… I like the structure. It’s been incredible. Incredibly fulfilling.”
How Kyle Stays Sharp
Kyle starts with his Roundtable. Beyond that, he meets with a business coach twice a month, works out regularly, and coaches football. On days when he’s “in the zone,” he’s up at 5 and in the office by 6.
Each morning, he journals about what went well the day before and spends time reading, all before 7 a.m. His wife teases him about his reading list. “She says I only read self-help books,” he says. “It’s what I read.”
To stay organized, he keeps index cards listing what he needs to get done each week, and his assistant runs his calendar. “I know what I got in 20 minutes. I know what I have an hour from now,” he says. But none of it works without people who’ll tell him the truth. “Have people that have your back, have people that tell you the truth,” he says.
He has one of those truth tellers at KRS, a longtime employee who tells him exactly what she thinks. “She’s like, look, I think you’re absolutely crazy, or this is the worst idea,” he says. “And I have a tremendous amount of respect for her.”
It works, he says, because they’ve built that level of trust. It’s people knowing you well enough to say, “here you go again, man. You got to stop being a squirrel.”
Defining Success
Kyle likes money, and he’s upfront about it. “I like money. Don’t be confused,” he says. A P&L, he adds, is “my report card.”
His definition of success is simpler: “Doing what you want to do when you want to do it.” That includes working seven days a week, if that’s what he wants. “While I may work seven days a week, I want to work seven days a week,” he says. “It’s not that I have to work seven days a week.”
KRS is far larger than it was in 2007. The responsibilities are broader, and the leadership team is deeper. Yet when Kyle talks about what he’s proudest of, he keeps returning to employees, relationships, and the people who have been willing to tell him the truth along the way.
“I would do this for free,” he says. “I really would.”
The Virginia CEOs Stories series highlights the leaders behind Virginia’s most impactful businesses and organizations. Their industries may be different, but their stories often share the same themes: perseverance, growth, and the people who help make both possible.
Here We Grow.
Kyle Stephenson is the founder of KRS Holdings, a Virginia-based real estate investment and property management company. He launched the business in 2007 and has grown it into an eight-figure organization serving markets across Virginia and North Carolina.
KRS Holdings is a real estate investment and property management company that manages residential properties, invests in real estate, and creates investment opportunities for employees and investors.
After a successful career in medical device sales, Kyle Stephenson pursued his passion for real estate and founded KRS Holdings in 2007, just before the Great Recession.
Kyle joined Virginia CEOs in 2015 to build meaningful relationships with fellow business leaders, gain new perspectives, and participate in a trusted Roundtable environment.
Kyle defines success as having the freedom to do what you want to do when you want to do it, while creating opportunities that positively impact employees, investors, and communities.
