Meet the New CEO of SUCCESS

Picture this: It’s 1989. You’ve just graduated college and are eager to take over the business world. Vying for a job in insurance, you want to look the part and those faded dress pants you’ve been wearing since high school aren’t making the cut. So you take a trip to the local Men’s Wearhouse, prepared to walk out with a new ensemble fit for a CEO.

Instead, you walk out with a business card and instructions from a young salesman named Glenn Sanford to head down to B. Dalton Bookseller and purchase Dress for Success by John T. Molloy—the book that popularized the idea of “power dressing.” You’re confused, until you read the book, after which you return to Men’s Wearhouse and let Glenn sell you a wardrobe of Molloy-approved suits, a blue blazer, and khaki slacks. But not ties or shoes. For that, Glenn walks you next door to Macy’s.

“(Management) got a bit annoyed because I’m not selling people in a normal way,” Sanford, now 54, recalls with a hint of a smile.

So not-normal was Sanford’s sales technique that he was ultimately fired from Men’s Wearhouse after a local politician requested to work with him instead of the assigned salesperson. Turned out management didn’t approve of letting ready-to-buy customers leave the building, even if they returned with deeper pockets. 

It wasn’t the only time he was fired. Working at a bowling alley at age 21, Sanford offered his bosses a detailed door-knocking business plan to increase league subscriptions. They fired Sanford but kept the business plan. He would be canned a couple more times before leaving the world of working-for-someone-else. 

“There’s only two people who really think about innovating: the CEO or the person who isn’t worried about getting fired,” says Sanford, the founder of eXp Realty, CEO of eXp World Holdings, chief strategy officer of Virbela, and now the CEO of SUCCESS Enterprises.

Sanford has spent the past 11 years growing eXp Realty, a cloud-based real estate brokerage firm, on a foundation of innovation, collaboration and agility. It’s this mindset that has seen the company through four consecutive years of 100 percent year-over-year growth. It now boasts more than 40,000 agents.

“Twelve years ago, I was looking to borrow some money from friends and family—we were basically upside down with the business—so we grew it from that point until now over a $4 billion market cap, which is pretty crazy,” he says. “It’s hard for me to wrap my head around sometimes, and yet we still feel like we’re just getting started.”

Ditto for SUCCESS Enterprises. SUCCESS magazine was founded back in 1897, and the website is hardly new. But with fresh ownership in place and massive plans for growth led by Sanford, it’s begun to feel like a 124-year-old startup.

***

If there is such a thing as an entrepreneurial gene, Sanford has it. Born in Peace River, Alberta to an entrepreneurial father, Sanford’s childhood résumé looks familiar. There were lemonade stands and paper routes. At 15, he made the local newspaper after creating accounting software for local businesses using a TRS-80 computer. His salary? Sodas and chips.

“My dad told me years ago that it’s riskier to take a job than it is to be an entrepreneur, which is sort of counterintuitive,” he says. “But a lot of people, when they take a job, that’s the most they’re going to make—they have an income ceiling.”

In college, he launched The Silver Platter Express, a fast-food delivery service. By the late ’90s, Sanford had built or worked for five technology companies, all relying on the power of the early internet. In a time when fewer than 45 percent of U.S. homes had a personal computer, Sanford was connecting with the world in a way that’s second-nature today.

“The ability to be collaborative with people that aren’t with you physically and still be able to learn new things, and try new things and build relationships, has been almost part of my DNA,” Sanford says.

Some of these ventures died out. Some simply lost his interest. He had some “normal” jobs too, but his entrepreneurial brain couldn’t be stifled. A couple of stints working as a stockbroker inspired him to share stock tips online, which grew into a gig running financial bulletins and chat rooms for AOL.  

Pivoting from the dot-com crash, Sanford began helping real estate agents with digital marketing needs. Fast-forward eight years and another three or four businesses, and eXp Realty, as it is today, was born out of yet another crisis. The housing market crash of 2008 forced Sanford to close three of his four real estate offices and downsize to a skeleton staff. What would have devastated most entrepreneurs, Sanford saw as a big opportunity. 

“There were always little things that I thought, If we ever did it again, we’d do it this way,“ he says. “So let’s take everything we’ve learned about this business, and let’s create a new model. It might not work, but if it does work, it has the potential of doing something really big.”

This model rejected the notion of brick-and-mortar offices, and shifted from to sharing much of the savings as additional revenue for the agents who helped the company scale and grow. And big it was; the model was popular, driving the business from 300 real estate agents to more than 16,000 between 2014 and 2018. They say the test of an entrepreneur is not the success of their ventures, but what’s learned from the failures and challenges of each. Sanford’s ability not only to pivot after crises, but to ultimately benefit and grow exponentially speaks volumes. 

***

“Life is short,” Sanford says with a shrug. He’s leaning against the kitchen sink of the outdoor casita (a small, permanent structure with a covered patio and restroom) he and his longtime partner, Debbie Biery, are renting while they look to purchase a winter lot of their own. We’re at the Motorcoach Country Club in Indio, California. Parked alongside the casita—essentially a covered patio with a guest bathroom—is their new 35-foot motorcoach. It’s smaller than their last one, a 43-foot Class A Winnebago, which they drove across 26 states in 10 months during 2015 and 2016—while Sanford scaled the virtual real estate brokerage. 

The decision to travel by RV came quickly. Sanford regularly flew to meet with the 1,000 eXp Realty agents across 31 states. In the previous year alone, he took more than 50 domestic flights. After their lease expired on a home overlooking Chuckanut Bay in Bellingham, Washington, Sanford suggested the motorcoach idea as a way to visit agents while traveling more comfortably. It landed, and the eXp eXpansion Tour was born (and documented on Facebook). 

“As long as it has a washer and dryer, I’m in,” Biery recalls saying as she laughs. 

In September 2015, belongings went into storage and the couple hit the road. They charted locations based on eXp Realty lunch-and-learn events, which Sanford hosted, and half-marathon locations. He would run six half-marathons in that year. 

Since then, it’s been hard to tie the couple down. Working from anywhere—not merely from home—is a core philosophy of eXp World Holdings.

“This whole concept is really just a natural progression in how society is developing over time, and you’re either trying to chase the past, trying to build the old model, or you’re trying to build the new model,” Sanford says. “I’d rather be focused on the latter, and focused on where things are going, and being part of that trend.” 

***

We haven’t left the casita but today it seems we’ve logged our 10,000 steps in Virbela, the 3D virtual office environment Sanford first started using in 2016. It was acquired by eXp World Holdings in 2018. Imagine the open world online game Second Life, except they’re paying you to be there.

We start in a daily huddle with the SUCCESS Enterprises team around an oval table. I recognize the avatars of the editorial and marketing staff. Working through a Trello board Sanford built based on the principles of SCRUM: The Art of Doing Twice the Work in Half the Time by Jeff Sutherland, the team gives individual updates on tasks in the “Doing” column. With the attention to detail of a project manager, he quickly works through the column, scheduling breakaway meetings if the task takes too long to work through in the huddle. 

“Let’s figure out how to get that done-done. Halfway done is as close to not done as it is to done,” Sanford responds to a payment setup issue. He’s friendly and soft-spoken, but he doesn’t waste time. The Canadian upbringing is unmistakable. 

We spend the rest of the day walking between various offices, chatting with people on the way to meetings and getting lost in the hallway of a newly added area. Sanford lives out a virtual version of a typical day in the office.

He is showing me how screen-sharing works in Virbela when an avatar labeled Ted walks in for a “got a second? It’s not work-related” conversation. This is what makes Virbela really work: outside of meetings, in the casual water cooler conversations and office pop-ins that otherwise couldn’t be recreated virtually.

“I think what is surprising to most people is how not alone they feel using this,” Sanford says. Most remote organizations have occasional video calls, and employees spend the rest of the day instant messaging but not speaking. “It’s definitely not as engaging,” Sanford tells me. 

On the other hand, Virbela does all it can to build camaraderie among teams. The “office” has a pirate ship and a soccer field. There are fireworks on Friday evenings, and the virtual Christmas party with dancing avatars was headlined by DJ Jazzy Jeff. But happy hour with a friend’s avatar isn’t quite the same. A quick virtual soccer game might garner a few laughs and boost morale, but no one gets an endorphin rush like they would from running on a real field.

Working through these kinds of things is in the problem-solving nature of a lifelong entrepreneur. It’s what drives Sanford, and he has a lot of ideas. 

“Whatever the new norm is, that used to be innovation five or 10 years ago,” he says. “We’ve got to figure out what that next thing is in innovation.” 

***

Sanford is wearing a typical work-from-home getup: gray long-sleeved athletic shirt with navy blue sweatpants and running shoes. He’s simultaneously laid-back yet deeply engaged with whatever task is at hand. Several times, he’s hovered over the unmute button during periods of silence, often choosing to be the last to weigh in. It’s a purposeful restraint that speaks to his goal of empowering everyone at the company.

“Organizations, the larger they get, the less agile they get because there’s all these controls that get put in place, and so nobody can innovate,” Sanford says. “My whole thing is ‘how can I help people be in their zone?’ ” 

This can partly explain his 96 percent approval rating from eXp employees on Glassdoor. Perhaps it’s the virtual setting, but they all seem to find him unfailingly approachable. He is a self-proclaimed geek with a bit of a professorial vibe; he’ll thoughtfully rub his chin with a slightly furrowed brow. You can almost see his mind working through problems—whether it’s how to foster real innovation or how to tackle revenue sharing for new international markets.

He likens entrepreneurship to chess, and it becomes hard not to imagine him playing out the next five years of the SUCCESS brand’s digital growth strategy on the ceiling, like in The Queen’s Gambit.

***

There are a lot of cliché questions that tend to be asked of successful people. These run the gamut of daily routines, habits, mantras, books on their bedside tables.

Armed with this information, we are meant to glean a recipe that everyone can follow. There’s a reason Steve Jobs’ single-style wardrobe is so often referenced in articles. It’s hard to wrap our minds around this abstract idea of rising above the status quo without also attaching to it some copy-and-paste methods for success.

I ask Sanford what he can’t leave the house without—a personal favorite. His response: pants. Each typical question is met with a typical person’s answer. He watches TV before bed. He checks email in the morning. He doesn’t eat breakfast. Sure, he likes to run because it helps him think and gets his blood pumping every day, but he doesn’t have a laundry list of cookie-cutter habits and mantras ready for an introductory profile piece—not even one for the magazine now under his leadership.

“I’ve never done any goal setting the way many people are told to do goals,” Sanford says. “But one of the things I discovered early on is that people don’t follow people that don’t have big visions. If you’re an entrepreneur and you’re truly not trying to change the world, work harder on your vision.”

Photos by Christopher Patey