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MTEC 2021 Keynote MTEC Entrepreneur Interview: Steve Winn

Steve Winn has impacted multifamily technology more than any other leader in over 22 years of service to the industry. Since the RealPage merger with RentRoll in 1998, RealPage has expanded into digitizing and automating every aspect of multifamily operations. Its organic growth has been outpaced only by its acquisitions of cutting-edge technology companies – buying capabilities when building them wouldn’t be fast enough.

Winn has held a consistent vision about entrepreneurship and technology adoption that culminated in the recent announcement that RealPage had been sold for $10.2 billion to private equity firm Thoma Bravo.

In an MTEC interview conducted by Joshua Tree Media’s Steve Lefkovits, Winn draws out some of the challenges of unicorn growth, and how he has led the company through multiple tech eras - from DOS to social media to AI chatbots.

Winn says that one key reason why much of his rich career has been so greatly involved with the apartment industry is because, “I like to associate myself with winners. Multifamily has been the best performing asset class in commercial real estate for a long time.”

He says it’s an industry about consumers, “and if there are companies out there that can perform better services at a lower cost,” they can take advantage of “the unlimited upside in this industry.”

RealPage itself has been greatly involved in mergers and acquisitions within the apartment industry. “We innovate, but we don’t hold the keys to innovation,” Winn says. “We let others demonstrate their success in having won in the marketplace. But they can’t always scale their businesses because they might not have enough sales people. But we do, so they come to us.”

Winn spoke of some of the most successful acquisitions from the dozens he’s been involved in.

“Leasing Desk grew by 50x after we bought it,” he says. “Clickpay is a highly successful payments processor for HOAs in New York City, giving us market share there. Modern Message brings catalytic change to the resident experience.”

More recently, RealPage is focusing on smart home technology. “The industry will have to move to this,” he says. “The cost to install smart home features has been cut in half lately, so this makes them affordable for retrofitting communities, too. We find that the IRRs on this are even better than renovating the kitchen.”

Winn was a hard worker and risk-taker early in his career. When asked what criteria he looked at before committing to a new product or service, he recounted a discussion he had with his wife before going forward with his personal financial investment in his dream.

“Are you prepared to have your standard of living significantly changed over this?” she asked. “Is it that good of an idea?”

“Yes,” he told her.

Winn says growing a successful company is not something a person should do on their own.

“I realized I couldn’t do it myself, so way back I reached out to private equity partners for funding,” he said, mentioning that those partners, although they have divested from ownership, still hold seats on his board of directors.

Winn advises others who are just starting out to not “give up” their companies fully to venture capital or private equity firms too soon.

“I see some company founders holding onto just 5 or 10 percent of their company when it’s sold,” he says. “Don’t dilute yourself or let you get talked into something by others.”

Ultimately, Winn says, company leaders need to do what’s in the best interest of their shareholders. “In regard to our sale to Thoma Bravo, who was I to get in the way of the shareholders’ interest?”


Looking ahead in the apartment technology space, Winn said, to be successful, young companies must identify a need and seek to fill it. “If you’re not doing that, and you’re not looking to offer a better way to do something, you’re not really an entrepreneur, right?”

Winn says automation and customer experience are part of the next frontier in apartment technology. But that they must be approached thoughtfully.

“You read about bots taking the jobs of 1,200 call center workers,” Winn says. “That worries me. But there will always be a place for human beings. Some call it artificial intelligence, but to me, it’s more like augmented intelligence. Have people and machines working together.”

With customer (resident) experience, he says, “We need to provide a hospitality level of service. That’s what the Millennial Generation is expecting. And they love a click-to-pay option. If I’m a developer, I’m looking for ways to earn revenue throughout the property. What areas are you not using in your communities?”

Chances are, Winn will soon have a solution for you.

Please click below for replay.




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