How hosting fuels an entrepreneurial drive

The sharing economy paves new ways to try new business ideas, says host Cynthia Rogan.

If there’s a common quality among Airbnb hosts, it’s an entrepreneurial drive. For Cynthia Rogan, short-term rental hosting not only pays the bills, but also paves a way to pursue new gigs and ideas.

Rogan, who has run her own Chicago brokerage firm since 2015, constantly explores new ways to take advantage of the sharing economy. Over the decades, the Pilsen resident has gone from concert producer for Prince and real estate broker to an Airbnb home and experience host, all while dabbling in new creative projects and helping young people in financial need.

The Chicago host juggles a lot of different projects, and she seems to prefer it that way. Rogan manages six listings from Pilsen to Wrigleyville, but her Airbnb enterprise hardly ends there. She plans to outfit her Pilsen location with audio equipment as she tests out her latest experiment, The Podcast Pad, and allows customers to book space for recording audio productions like podcasts.

“I have so many ideas coming in. And before the sharing economy, I didn’t have a way to apply them,” she said.

Rogan is one of 9.6 million self-employed in the U.S., according to 2016 data. The average number of self-employed is growing at a faster clip than of the overall workforce, to reach 10.3 million by 2026.

Her roots in real estate, particularly during the housing bubble, helped her understand opportunities in short-term renting as well as Chicago’s nuanced socio-economic problems. After moving to the city to work on Prince’s concerts as part of local production company Jam Productions, she entered real estate in the early 2000s. Her brokerage business, which involved mostly investment properties, was hit hard by the 2008 crash. She also witnessed how it hurt homeowners in low-income neighborhoods and worsened Chicago’s economic disparity.

“While the distress in my life happened during the market crash,” Rogan said, “that’s where their troubles started.”

Banks sent her to appraise foreclosed properties so they could offload troubled assets, and investors sent her to scoop up the undervalued homes. Critics contended at the time that many financiers who helped create the real estate crisis would profit from buying houses at a steep discount.

Investors would buy empty homes in Englewood during the downturn and turn them into rental properties. But when they failed to maintain the houses, the South Side neighborhood fell into disrepair. Her first-hand view of the housing crisis’ effects has motivated Rogan to reinvest part of her Airbnb income into scholarships, housing and job opportunities for college students in need of financial assistance through her Props For All Peeps community redevelopment initiative.

I have so many ideas coming in. And before the sharing economy, I didn’t have a way to apply them.

Cynthia Rogan

Rogan also reaches out to local businesses about hosting pop-up food and drink experiences at her Wrigleyville location before Cubs games. She sees it as an opportunity to provide fans with unique pre-game festivities while offering local restaurants and breweries access to prime real estate during peak demand.

“To put experience packages like that together is really fun for me,” Rogan said, because they tap into her passion for entertainment.

Rogan says her knowledge of the Chicago real estate market has been instrumental to her success as a host. But, like many other multiple-property hosts, she’s still working on better crunching the numbers and automating the guest management process.

“I’ve lived in Chicago long enough to know about frozen lockboxes,” Rogan said. But she continues to innovate, integrating more software tools and smart devices to make her Airbnb business more efficient.

Her motto is “stay local, shop local, stay-cation, make-cation.” Nonetheless, Rogan says Airbnb excites her because it allows her to meet people all over the world.