How One Serial Entrepreneur Found His Perfect Fit with Office Evolution

When Cliff Osbon hit pause on his television one Sunday morning, he had no idea that a CBS Sunday Morning segment would change the trajectory of his entrepreneurial career. Today, he and his wife Angela are the proud co-owners of Office Evolution of Flowood, located in the Jackson, Mississippi suburbs—and they couldn’t be happier with their decision.

“I said, why would people not want to have fractional ownership of office space the same way we have fractional ownership of a car when we Uber, the same way we have fractional ownership of a condo when we Airbnb,” Cliff recalls. “So this seems like a brilliant idea.”

That brilliant idea led Cliff and Angela to explore the flex office industry, eventually bringing them to Office Evolution. Their journey offers valuable insights for anyone considering a franchise opportunity in the thriving flexible workspace sector.

Why Office Evolution? The Strategic Advantages of a Suburban Flex Office Franchise

As a serial entrepreneur with experience across multiple industries, Cliff approached his franchise search with a discerning eye. He and Angela evaluated three different companies before making their decision. What set Office Evolution apart?

Designed for Secondary and Tertiary Markets

“We liked the Office Evolution model because it was designed for secondary and tertiary markets,” Cliff explains. “Rather than focusing on the Londons and New Yorks of the world, these were going to be more focused on the Denvers, the Atlantas of the world—secondary markets—or tertiary markets like Boise or Raleigh or Jackson, Mississippi.”

This strategic focus on suburban and smaller metropolitan areas gives Office Evolution franchisees a distinct competitive advantage. While major coworking brands compete for expensive downtown real estate in major cities, Office Evolution franchise owners serve the growing demand for professional workspace solutions in communities where people actually live and work.

Suburban Locations: Meeting Members Where They Are

“We also liked that many of the Office Evolution locations were suburban rather than in the downtown locations,” Cliff notes. “And that worked for us where we live.”

This suburban positioning proved especially valuable when Cliff and Angela opened their doors in May 2020—right in the middle of a global pandemic. Their location, strategically positioned close to suburban neighborhoods, became a haven for professionals who had been displaced from centralized downtown offices and were looking for a smaller, more convenient workspace closer to home.

The Franchise Advantage: Why Support Matters

One of the biggest decisions any entrepreneur faces when entering the flex office industry is whether to go it alone or join a franchise system. For Cliff and Angela, the choice was clear.

“I felt like franchising was a better way for us to go because we were going to get some support and guidance,” Cliff says. “We were going to get marketing on a national scale, and we felt like the cost for that—that you pay as a franchisee—would be worthwhile.”

The franchise investment in an Office Evolution location comes with comprehensive support that independent operators simply don’t have access to—from national marketing resources to proven operational systems.

Comprehensive Training for Owners and Staff

The franchisee support system at Office Evolution proved invaluable, even during challenging circumstances. Opening during the pandemic meant most of their training had to be conducted virtually rather than on-site, but Cliff found the experience still delivered everything they needed.

“We still had the same training modules. We still had the same exposure to the same software packages,” Cliff recalls. “And so I don’t think we really sacrificed anything by that virtual training. Certainly, we would not have had familiarity with the business management software or the CRM that was available had we not had that training.”

This training extended to both Cliff and Angela as co-owners and their initial Business Center Manager—the person who runs the day-to-day operations of the location. This comprehensive approach ensures that everyone involved in the business has the knowledge and tools they need to succeed.

Expert Guidance in Site Selection

Finding the right location is critical to any coworking business’s success. Cliff credits the combined expertise of a local real estate broker and Office Evolution’s corporate team for helping them identify the perfect spot.

“It was far enough away from downtown and close enough to the suburban neighborhoods that people who had been displaced from maybe centralized offices were looking to find a smaller office closer to home,” Cliff explains. “And so the pandemic was actually a little bit helpful for us in our launch.”

Office Evolution also provides franchisees with a heat map tool, developed in partnership with United Franchise Group, that helps identify the most promising areas within a metropolitan region. This data-driven approach takes much of the guesswork out of site selection.

The Rewards of Running a Flex Office Franchise

For Cliff, the most satisfying aspect of owning an Office Evolution franchise goes beyond the business metrics. It’s about community and connection.

“I think it’s just being around other entrepreneurs. I find that very engaging,” Cliff shares. “We get to help support other businesses as they grow. We have a lot of solopreneurs—people that are in business by themselves, for themselves and their customers—and we get to help them.”

“They have a space—we can give them a very professional place to work and meet their clients and their prospects,” Cliff continues. “We participate in several business leads and development groups, and one thing we do is help our members find those same type groups so they can get more leads and grow faster and more successfully.”

Looking Ahead: Growth Opportunities in Flex Office Franchising

With their Flowood location thriving, Cliff and Angela are now exploring ways to expand their business. Rather than opening a second location, they’re focusing on maximizing the potential of their current space.

“We are looking at the opportunity to expand our current location and try and acquire a little more space in the building we’re located in,” Cliff says, “and try and maximize the efficiency and return on investment where we are.”

This approach reflects one of the lessons Cliff would share with prospective franchisees: the importance of securing adequate space from the start. “I would encourage people to take a good, long, hard look at how much space you need to optimize your return on investment.”

Advice for Prospective Office Evolution Franchisees

For entrepreneurs considering an Office Evolution franchise, Cliff offers practical guidance based on his own experience:

Connect with Existing Franchisees

“I would encourage people to do what we did,” Cliff advises. “If you are in a particular market, try and look at other markets where Office Evolution is located and talk to the franchisees, the owners in those markets. A similarly sized city to yours, similar demographics to yours, similar income to yours. I think those are really helpful things.”

Leverage Data-Driven Site Selection

“I also think in making the decision of where to locate, the heat map that Office Evolution and United Franchise Group have made available is really helpful,” Cliff notes, “because you can identify parts of a metropolitan area that you’re likely to be more successful in than others.”

Would They Do It Again?

When asked if they would make the same decision today, Cliff doesn’t hesitate: “When we’re asked if we would do this again, I think we would.”

He acknowledges there are things they might do differently—like holding out for more space—but the fundamentals of their decision remain sound. “We love our location, we love the suburb that we’re in outside of Central Jackson.”

For Cliff and Angela Osbon, what started as an intriguing idea glimpsed on a Sunday morning television program has become a thriving business that allows them to support their community while building wealth for their family. That’s the power of the Office Evolution franchise opportunity.

Ready to Start Your Own Office Evolution Journey?

If Cliff and Angela’s story resonates with you, now is the time to explore what an Office Evolution franchise could mean for your future. With flexible workspace demand continuing to grow—especially in suburban markets—the opportunity has never been stronger. Learn more about the franchise opportunity and take the first step toward owning your own flex office business today.