How Steve Frey created the ‘Airbnb for Business’ and his plans to bring the offering directly to consumers

Steve Frey has had a ‘meh’ opinion of the corporate world from an early age. He watched his father, after many years with an employer, experience a layoff and it stuck with him. 

This inspired him to want to be an entrepreneur and not rely on corporate America to take care of him and his family. After “failing” in the corporate world, he became an entrepreneur. 

He launched Oasis Corporate Housing during the financial collapse of 2008. But he wasn’t worried. “You can’t go backward from zero,” says Steve Frey. 

He and his business went forward, indeed. By 2018, the company had $62 million in revenue and, by 2022, the company had $120 million in revenue. He is projecting to grow to $145 million, in 2023. 

How did his company see such growth? Here’s a hint, the buzzword of the year. Automation. We’ll get to that. But first, it’s important to look back on his family’s story of immigrating to the United States, where his great-grandfather started a bread company, in New Jersey.

THE ENTREPRENEURIAL GENE

Frey’s great-grandparents immigrated from, what today is Ukraine and Poland, in the early 1900s, ending up in New Jersey. Frey says the only thing his great-grandfather knew how to do when he got to America was bake bread, so he started a small company and would sell loaves of bread, in New Jersey. This small business ended up being the Frey Bread Co., which grew in popularity partly due to Albert Einstein becoming a loyal customer of its rye bread, Frey says.  

“My grandfather grew up working there so, when he got older, he opened bakeries in Pennsylvania and New Jersey,” Frey says. “My grandmother is the only one that’s still living and remembers all the stories from back then. Growing up in the Great Depression, they had to be entrepreneurial.” 

Frey recalls, at that time, families wanted their kids to grow up and have a “safe” job. Education was the key to getting there. To get that corporate job and have job security. 

“That’s how my dad was raised,” he adds. “It’s interesting, you see the generation before you and it kind of molds what kind of path you may go down.” His parents wanted him to have a safe, corporate job so he wouldn’t have to struggle as an entrepreneur as they had. 

Frey was born in Freehold, New Jersey. Fun fact, he is from the same general area as Jon Bon Jovi and Bruce Springsteen. 

His family moved around a lot, while he was growing up. 

“Part of my personality is that I can get along with anyone pretty quickly and part of that is because I was forced to move a lot,” Frey says. “Every time you move, you have to meet new friends. What other choice do you have?” 

At the age of 12, his family moved to Tampa. Not long after, he watched his father get laid off and it left a significant impression on Frey. 

“I remember the day when he sat us down, at the kitchen table, and said, ‘This is what’s going on.’ I could see the stress and, maybe even, the fear,” Frey recalls. “I remember thinking, when you work for a big company, you’re actually not necessarily any safer, but when you work for yourself, you’re the last person that gets fired.” 

Frey says his father worked hard to elevate in the corporate structure with a goal to provide his family a “good, middle-class life.” 

“My grandparents worked their butts off to be able to afford to send him to college, so he could get a good corporate job, and then my mom and dad worked their butts off to be able to give me the opportunity to say, ‘Do whatever you want.’ “

In Tampa, Frey attended Chamberlain High School where he played baseball, made good friends, some that he still maintains, and he planted roots in the Tampa community. Unknowingly, at the time, he was setting up his future to have his company grow up in Florida as well. 

GOOD TO GREAT

Frey attended Florida State University, where he studied accounting. He intended to continue playing baseball, but his self-awareness kicked in. 

“I wasn’t good enough to play professional baseball so, at some point, you have to move on with your life,” Frey says laughing. “It was a good time to do that and just become a fan of the game.” 

Like many leaders of organizations have said before, playing sports taught Frey a lot that he carries with him in his current role as chief executive officer of Oasis Corporate Housing. 

“Part of it is in terms of how you treat people on your team and part of it is how to motivate yourself,” Frey says. “It may be universal but, for me, I also always wanted the approval of my father.” 

With baseball, he was good, but, Frey says, he wanted to be great at something. 

“To me, business was the last thing I had,” he says. “When you start a business, you start at zero and you think, ‘Yes, this can work, but how can I make it great?’” 

Some of the lessons began while he played team sports, but they weren’t fully realized until he got older. 

“Nothing happens on your own,” he says. “You do something that you feel like you accomplished some level of success, but you realize it’s really a result of a collective effort of a lot of people.” 

Easier said than done, at times. “Everyone is the star of their own movie,” Frey says. 

Frey attended graduate school and honed in on a business tract, moving along the status quo of moving into a corporate world with a ladder to climb. 

“I read a lot of books on good leaders and common characteristics of good leaders and, I realized, later, there is no one way to be, it’s just your way. You have to be authentic to yourself,” Frey says. 

After finishing his graduate studies, he returned to Tampa and interned at PricewaterhouseCoopers. He attended the University of South Florida to get his certified public accounting license. 

After about three years, he realized it was not what he wanted to do long-term. 

“I’m a very sociable person. In accounting, you’re behind a computer and I wanted to be in front of people,” Frey says. 

He spent some time as a consultant but with little world experience, he felt unfulfilled. 

“I’m supposed to go in and tell these people who have had successful companies for decades, but a few stumbles, ‘Oh, you should do this and this,’” Frey says. “I’m like, I have no right to advise these people. And I’ve done nothing myself. That’s when I got in my head. I wanted to see if I could put my money where my mouth was.” 

THE LAST PAYCHECK

Frey still has the last paycheck he received before jumping out to generate his own. He never cashed it. 

He vowed he would never rely on another person for his income, ever again. That is when Oasis began to take shape. 

He remembers talking with a friend that ran the temporary housing placements at MacDill Air Force Base. 

“She ran the housing department at MacDill and she was telling me about how companies would rent an apartment for a year, furnish it, provide housekeeping, cable and internet, and make it ‘turn-key’, then rent it back to the military on a nightly basis,” Frey says. 

He thought it was a cool idea he could build a business on, so he rented five apartments. For the first two years of his housing business, he paid himself $30,000 a year. 

As the company grew, he slowly added employees and units to manage and rent out. Frey knew Oasis would need to diversify to grow. The key to that was corporate housing. 

Potential clients were telling Frey that they wanted to work with a company that could handle all their needs, not just in the Tampa Bay region, so the next step was going national and, later, going global. To do that he partnered with similar companies which led to the ability to do his business anywhere in the world. 

There were some growing pains. 

“All of my clients wanted something different and there was no way to keep all of this information straight,” Frey says. For the next phase of growth, Frey’s business would need software that wasn’t built yet. 

He hired some developers in Ukraine to help with this and still works with them to this day. 

We’ve been building software for years now. It’s something we’re going to always build to get better for our customers, be more efficient and drive cost savings,” Frey says. 

These days, Frey describes his company as the Airbnb for businesses. 

“The biggest difference is when you book on Airbnb, you work directly with a renter being connected to a host, so Airbnb holds very little responsibility over your experience there,” Frey says. 

Meanwhile, Oasis offers a direct approach to preparing and working with their clients through their stays. They feel, and are, responsible for the client’s happiness. 

The next step for Oasis is moving into the business-to-consumer space. 

“We’re a [business-to-business] company but that doesn’t mean that we can’t offer a similar solution to a [business-to-consumer],” Frey says. With remote work and the arrival of the concept of “workcations,” many will be interested in relocating to a particular destination that won’t be conducive to hotel living or the constraints of Airbnb.  

“We’ve been building a lot of our tech around automation process flow to be able to cut down on the human labor cost per booking,” Frey says. “We wouldn’t downsize due to this [technology] but it will allow us to grow without adding more staff.” 

When asked about the incredible growth in his company over the course a few of years, keeping in mind his company had 100% growth from 2021 to 2022, he speaks of his team and his view of leadership. 

“Whenever I interview for higher level positions, I always ask the question, ‘Do you hate losing more than you enjoy winning?’” he says. “Me, I hate losing.” ♦ 

MARTINIS FOR MOFFITT

Frey and a group of friends (the Bay Area Advisors) established Martinis for Moffitt in 2006. 

“We were getting together, maybe once a month, trying to exchange business leads and we eventually got to a point where everyone owned their own businesses,” Frey says. 

In addition to growing their own businesses, they, collectively, decided to start giving back to the community. 

With the thought that almost everyone, at some point, has been affected by cancer, they decided to fundraise for Moffitt Cancer Center. 

“We were like, what can we do? And we looked around and realized we were good at throwing a fun time for people,” he says with a laugh. 

The first year the Bay Area Advisors held Martinis for Moffitt at The Tampa Club, which donated 10% of the bar tab to the cancer center. When H. Lee Moffitt happened to be there that night, and saw the sign promoting the event, he said, “Martinis for me?” Frey estimates that first year the group donated $2,000. 

“We didn’t know where it was going to go, but we’ve now donated about $2.5 million dollars and have definitely outgrown the Tampa Club space,” Frey says. 

LIKE FINE WINE

One of Frey’s favorite places to visit, in the world, is Montalcino, Italy. He has a great appreciation for wine, so it makes sense.

“What I like about wine is the nuance,” Frey says. “I think that I try to approach life like that, whether it’s personal or professional, finding appreciation in the details of it.”

When thinking of this type of nuance, Frey draws inspiration from brands such as the Buddha-Bar Hotel, in Prague, with no expense spared in bringing the smallest detail to patrons’ experience (starting with a “welcome drink” as soon as you walk in the hotel). Frey’s respect for the attention to detail in wine draws an affinity for his favorite wines from the Montalcino area such as Podere Forte’s Petrucci or Uccelliera’s Brunello. 

Injecting that same type of attention to detail at Oasis is a large part of the success that has been created, Frey says. 

Photo by Pamella Winslow

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