When Jacobie Olin and his siblings were growing up, their chores often included stripping beds and taking out the trash at vacation rentals. They were early lessons in values like service, teamwork, and commitment, things that would eventually come full circle in their family’s business. No one knew that short-term rental investments could become such a passion for the Olin family.

After graduating from Middle Tennessee University with a bachelor’s degree in economics, Jacobie worked in the food and beverage industry for seven years as owner and manager of a honky-tonk-style bar in Nashville.

However, he increasingly became more interested in his father’s business focusing on short-term rental investments, C2G Advisors, after seeing the innovation and growth in the industry. With the encouragement of his wife, he decided to join the advisory group and earned his real estate broker’s license in 2018.

He liked how the industry had driven innovation in technology and had become an incubator for budding entrepreneurs.

“It’s a cool industry in the way that it has allowed homeowners to make some money to improve their lives, whether that’s putting children through university, paying their mortgage, or pursuing a passion,” Jacobie said, “and in the way that guests, particularly group travel guests, can find a lodging alternative that that’s better suited to them, instead of renting three, four, or five hotel rooms.”

His dad, Jim Olin, founded C2G Advisors in Nashville, Tennessee, in 2004 after working for prominent private and public vacation rental management companies such as Abbott Resorts, ResortQuest, and Sterling Resorts. Jim founded the company because he wanted a way to share his experience, wisdom, and insights on the industry with others. He built the company on decades of experience in vacation rentals and property management mergers and acquisitions (M&A).

The family-owned-and-operated advisory group specializes in M&A, hospitality and litigation consulting, general consulting, and real estate brokerage. Jim is CEO, his son, Jacobie, is the president, and his other son, David, does the company’s data analysis.

The road to vacation rentals

Jim got into the vacation rental industry in 1992 after serving as executive director at various chambers of commerce.

In his first position in the vacation rental industry, as CEO of Abbott Resorts, he was involved in every aspect of the operation, including sometimes mowing lawns and changing bedsheets.

He enjoyed the challenge of balancing owner and guest interests.

“It’s not an authoritarian type of business; it’s a business of psychology, negotiating, and finding a middle ground,” Jim said.

He also liked that property management was asset-light and had multiple revenue streams from guests and homeowners.

“This industry breeds innovation,” Jacobie said. “Every week we talk with a new entrepreneur that is working on exciting niches, whether that be owning/operating short-term rental homes, building technology that simplifies the complex process of hosting guests, creating safety programs to ensure safe and secure homes for the homeowners and guests alike, and much much more.”

Earned trust by living core values

Today, integrity is one of C2G’s core values, alongside faith, service, giving, passion, teamwork, innovation, and commitment.

About 75% of C2G’s business is property management company acquisitions. Since 2004, they have completed hundreds of mergers and acquisitions. These deals involve trust, integrity, and confidentiality and can sometimes take as long as two years. 

“In a business like ours, you have to have extreme confidentiality and integrity, or you’ll never work in it again,” Jim said. “You have to have values that show that. And our values are why we’ve been able to be so successful because somebody can call us up and say this is off the record, and we’ll never share it.”

Jim and Jacobie, who handle the M&A, typically search for companies with values that are similar to those of the buyer and also have to do extensive research on the regulatory landscape in the market their buyer is targeting.

Responsible renting advice for short-term rental investing

While most of their clients are buyers who want to acquire property management companies, they also advise clients on responsible hospitality practices such as safety and owner-guest contracts.

Between 2018 and 2021, Jim served as chair of the Board of Directors of Vacation Rental University, the industry’s first fully-integrated education and certification initiative. The education center in Destin, Florida, provides educational resources and programs to help operators professionalize and improve their business with a pricing plan that ranges from free classes to paid certifications.

Jim is also a passionate advocate for short-term rental safety measures. He earned a vacation rental safety certification from Breezeway and encouraged others to do the same.

“If you’re a vacation rental property management company and you’re not focused on safety, you’ll need to take that more seriously,” Jim said.

As safety and other standards and regulations become a bigger focus for both private companies and lawmakers, C2G brings it all back to their core values.“We are in the early innings of mainstream exposure to our industry, so it is more important than ever before to create responsible renting practices, in order to help facilitate collaborative communication with the local municipalities that is accretive to all parties. Focusing on professionalism and safety will help achieve the goal of building a sustainable industry,” he said. “Our job as professional managers is to float the boat higher.”

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