Mind Your Money: This CEO Wants To Use Real Estate To Build Generational Wealth

She built her business ground up, self-financing it.

Name: Brianna Regine

Occupation: owner of Brianna Regine Visionary Consulting, a strategic communications, and marketing agency

Age: 27

Location: Connecticut

Income: Business generates six figures

Goal: Get into the Airbnb arbitrage business

Brianna Regine is “your person.” If you need public relations, strategic communications, or digital marketing help with your personal brand or business, the chief executive officer of Brianna Regine Visionary Consulting is the one you hit up to get the job done.

Since she was a child, she has dreamed of working in the entertainment industry. After trying her hand at dancing and other creative mediums, she decided to major in communications in college. She focused less on performance and more on pulling the strings behind the scenes to make brands ”pop!”  

“I wanted to help folks who would be viewed as the underdog or are super creative but not sure how to strategically bring their ideas to life,” Brianna, 27, of Connecticut, said.

Her clients include the Connecticut Office of the Arts, investment and trading company Cheat Code, Cheryl Grace, CEO & Founder of Powerful Penny, and Independent Trust, a non-profit and professional network supporting alumni of color from independent schools.

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“I touch every sort of work type,” Brianna said. “The commonality is supporting people, finding  solutions, and not taking a “no” for an answer.”

Since opening her firm five years ago, Brianna shaved her workday from 15 hours per day to 12 hours. She is projected to double her six figures worth of business sales this year and hopes to quadruple the income in the foreseeable future. She wants to add a formal apprenticeship program to her firm.

“The CEO title is hitting home with me,” she said. “The main thing is giving opportunities to others and providing opportunities to others.”

With her agency thriving, the millennial says it’s time to focus on her finances. 

In her heart, Brianna would like to purchase a multifamily property and rent it out with tenants. Brianna’s parents invest in real estate income property, and she sees it as a lucrative way to build generational wealth.

However, it’s harder to get a loan as a self-employed person. Proving your cash flow as a business owner, freelancer, gig worker, or contractor can require more paperwork than W-2 employees.

Brianna doesn’t have the capital needed to purchase a property. She has $39,000 worth of student loan debt. According to Zillow, Connecticut’s average home price is $340,415. She built her business ground up, self-financing it.

In the interim, one solution that she is exploring is getting into the Airbnb rental arbitrage business. Airbnb rental arbitrage is renting a property and then subletting it for profit on the Airbnb or other short-term rental platforms. It’s often used for vacation rentals. Brianna learned about it from listening to a personal finance podcast, which she does in her leisure.

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“The Airbnb option has a lower entry point. The investment is not as much. The turnaround for potential profit comes quicker to build the capital to get me that multifamily home or duplex,” said Brianna. She lives at home to manage expenses.


“Airbnb rental arbitrage is a very attractive business model,” says Fred Bassili, marketing manager at Hostfully, an end-to-end property management software. “The beauty with arbitrage is that there is very little overhead in theory.”

According to Hostfully, the vacation-rental industry has grown over the last decade and is now a $115-billion industry. Platforms such as Airbnb,, and VRBO have made it easier for the little guy to enter the market.

"Before getting into Airbnb rental arbitrage, it's essential to check your state, county, and municipality laws to see if vacation rentals are allowed and under what conditions," says Bacilli. "In this stage of due diligence, the entrepreneur will get a better understanding of taxation and reporting requirements," he says.

"The last thing you want is to sign a lease with no chance of renting out the property," Bassili said.

Don't just go by what appears to be a "good deal" with finding a property to lease, he says.

Websites such as AIRDNA and Keydata offer statistics on the vacation-rental industry. On those sites, you can see the average-nightly rates for the area you want to use for your business, how often the properties are occupied and what the seasonality is like, he said. Bassili recommends investing in the paid data on the sites.

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"You can forecast what your property will generate by using more than gut instinct," says Bassil. "Zillow is good for discovering average rent in the area you want to lease," he says. 

While Airbnb rental arbitrage has a lower overhead and entry point, as with any business, there will be start-up costs while getting established.

Bassili recommends having enough savings to cover the first three months of expenses on the property. 

When approaching landlords about properties to lease, Bassili said that people must disclose to the landlords that they plan to run an Airbnb arbitrage business from the property. "Pitch it to the landlord as a great deal that will guarantee stable income, he says. Make sure to let the landlord think it's a great business idea for them," says Bassili.

In addition, be prepared to invest in furniture and other marketing. It's not unheard of for the rental arbitrage hosts to spend $15,000 to $20,000 on furniture to give the property "click appeal." 

In addition, higher quality furniture lasts longer. "If you don't want to invest in higher quality furniture, be prepared to purchase furnishings more often because the wear-and-tear on vacation properties is higher than with a family home," he says. 

Budget for regional expenses, also, he said. For instance, budget for air conditioning if you purchase in Miami, heating expenses if your business is in Upstate New York. 

"Successful people in the Airbnb rental arbitrage industry are comfortable dealing with people, excellent at sales, and meticulous about how their properties are presented online," he says.

Also, people considering getting into Airbnb rental arbitrage must be excellent at research. There is no "property manager" degree in college, Bassili said. 

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