Many Illinois REALTORS® focus their real estate businesses on helping consumers buy and sell homes.

But some add side businesses which allow them to get paid to do something they love or accomplish a business goal they’ve always had.

Illinois REALTOR® talked to four REALTORS® about their successes with side gigs and what others need to know to get started.

Vacation rental

Judy Gibbons, a broker with Jameson Sotheby’s International Realty in ChicagoJudy Gibbons, a broker with Jameson Sotheby’s International Realty in Chicago, had a long-time goal of someday buying an investment property.

She was thinking of a three-unit building or another type of rental investment in the city, but after a colleague bought a cottage in Michigan, she changed her mind. She started thinking instead about buying a vacation property that she could rent out on Airbnb while also using it herself.

In 2016, she and her husband bought a two-bedroom, two-bathroom cottage in Lakeside, Mich. Located in the touristy Harbor Country and within walking distance to Lake Michigan, their Dunedin Cottage quickly booked up the first summer and continues to be popular year-round.

“It’s been such a source of pride,” Gibbons said.

For a REALTOR®, vacation rentals make sense, she said. They know houses, they have staging tools and the extra source of cash flow is a plus, she said.

“It’s a great opportunity for people in real estate to expand their business and have fun,” Gibbons said.

Her advice to others getting started in rentals? Do your research and talk to a lawyer about what you need to do to set up a rental property. Look for properties near amenities that people would want on vacation and once you find it, make it feel like home.

“You’re painting a picture the same as you would if you were listing a house,” she said.

Gibbons found she can use the vacation rental to build existing business relationships by offering it as a perk during the off season to valued clients. She has also donated cottage stays for non-profit fundraising events.

“To me, it’s such a win-win. Personally there is joy to use it, professionally I can use it to make my clients happy and then financially it’s a nice business,” she said.

Quick Tip: When decorating a vacation rental, think about furnishings that will appeal to a wide audience, are sturdy enough to withstand multiple guests and are things you are OK with getting broken if something happens. Solicit reviews of your property and get professional photos taken to make your vacation rental look its best.

House flipping

Nate Shields, a broker with eXp Realty, in the Sycamore-St. Charles areaFor Nate Shields, a broker with eXp Realty, buying properties, rehabbing them and then flipping them to sell was a natural progression.

After three years of selling real estate in the Sycamore-St. Charles area, Shields and a friend decided to move into investment rental properties, buying several single-family homes, a duplex and eventually a 20-unit apartment building.

Shields decided the next thing he wanted to tackle was rehabbing homes for resale. His company, Invermore Enterprises, has flipped six homes so far, averaging one or two projects a year. Shields, who has extensive experience in real estate, has relocated to Wisconsin, but maintains his Illinois license to focus on his home-flipping business.

“It’s been interesting and you just learn so many different aspects of real estate,” he said.

You also learn what not to do, Shields says. His first flip was an extensive rehab project from nearly top to bottom and it was not without problems. Shields had to replace the contractor, but the experience left him more confident about getting what he wanted going forward.

“The scariest part for me and for a lot of people is when you are doing a big rehab, especially if you are not in the trades and don’t know much about construction, is finding the contractor, making sure that you’re not getting ripped off, making sure that it’s quality work and it’s done on your timeline and on your budget,” he said. “It’s a big thing to take on and I think that’s why a lot of people don’t get started.”

Transforming an outdated  home is rewarding, but rehabbing is ultimately a money-making venture so Shields is always aware of the bottom line.

“You have to think about who the end buyer is very carefully, so you know what to put money into,” he said. “Where a lot of flippers make mistakes is they put in the features they want to see and usually that’s going to be higher end. People are going to love it, but it’s not going to give you a good return on your money.”

Quick Tip: Determine your short- and long-term goals and work backwards from there. Find good contractors to work with if you aren’t doing the rehab work yourself, educate yourself on the investment market and if you don’t have a real estate investor networking group in your area, think about creating one.

A bar graph showing Secondary business specialties of REALTORS®

Instructor, trainer

Sandra Workman, a broker with Keller Williams Preferred Realty in BourbonnaisSandra Workman, a broker with Keller Williams Preferred Realty in Bourbonnais, is a self-professed education junkie.

Workman, ABR, BPOR, CNE, CNHS, CRS, e-PRO, GREEN, GRI, RCC, SFR, says she loves to learn all she can about the real estate industry and wants to share that knowledge with others to help enhance industry professionalism.

“If you don’t educate yourself in this business, this business will leave you behind,” she says.

A REALTOR® for 15 years, Workman got her license to teach continuing education courses in 2016 after seeing a need in her area. Agents were having to travel closer to Chicago for classes or offices had to bring someone in to teach.

“We needed someone here to teach agents about core competencies and keep everyone current on changes in the industry,” she said.

She’s also become an MLS trainer for Midwest Real Estate Data LLC (MRED) and teaches agents as far away as Champaign, Bloomington and Clinton all while juggling the day-to-day demands of being a full-time REALTOR®.

“It’s all in prioritizing, it’s in time-blocking,” said Workman, who is also a productivity coach for Keller Williams and does real estate photography in her spare time.

Family time gets blocked off first, then her real estate clients and then her classes. The teaching demands ebb and flow. Demand for her CE courses ramp up before license or Code of Ethics renewals. When CE slows down, she fills up her calendar with MRED trainings.

Workman loves doing her part to improve the industry and the extra revenue she is bringing in from teaching is being set aside to help her realize her next goal: buying some investment properties.

Quick Tip: Teaching isn’t right for everyone. You have to have the right type of personality and mindset to do it because it can take up so much of your time. Try to learn something new every day.

Property management

Joe Castillo took over his parent’s real estate business, RE/MAX Mi Casa in ChicagoIn 2008, when Joe Castillo took over his parent’s real estate business, RE/MAX Mi Casa in Chicago, the Illinois housing market was in a downturn so he established a niche as an REO broker selling foreclosed properties.

It was in that process of getting homes ready to sell that Castillo built contacts with different contractors, handymen, landscapers, plumbers and other tradesmen. As the market improved and the REO business slowed, Castillo looked for other ways he and his company could leverage the knowledge and contacts they had accumulated.

“We had a knowledge base and a network in place of tradesmen,” he said. “We learned how to manage other people’s properties and so there was a lot of skill sets that transfer from REO management to property management.”

He looked around his south side neighborhood and saw that there wasn’t anyone really doing third-party property management. Most property managers were just working with rentals that they owned. Few were doing property management for someone else.

So two years ago, Castillo and Oscar Campos, a broker in the office, added a property management division within his office to create systems to manage the rental properties owned by his company. Last year, after he felt like he had the proper software, employees and processes in place, he expanded and started adding third-party clients.

Castillo looks at the property management side of his business as a good buffer to the ups and downs of the housing market.

“If the market slows and things change, I think the property management side of things will probably grow,” he said. “It’s a cash flow positive business, so a downturn in value doesn’t necessarily affect these properties or investors that much.”

Long-term, Castillo sees another benefit to the property management side of his business. As he works with tenants, he builds relationships with renters who may someday become buyers and will hopefully come to him when they are ready to buy a home. 

Quick Tip: Do your homework and don’t expect it to be easy. Castillo encourages people to start by having their own investment properties and managing those first to get a better understanding of the business. Then determine how much staff you need and build relationships with tradespeople who will prioritize your properties when the pipes freeze or some other problem needs to be fixed.