“You can read a book about how to swim but you can’t learn until you jump in the water,” says Sean Dailey, who offers a wide range of realtor services for investment properties, commercial properties, and residential properties in Barrington and the greater Chicago area.

Dailey jumped into the real estate waters more than a decade ago, developing and subsequently selling a restaurant. Now he helps clients build real estate portfolios by advising them on purchasing multi-family housing.

Dailey bought his first investment property, a house in Northbrook, in the early 2010s, and went on to buy and sell a number of multi-unit buildings, most recently a 17-unit building on Chicago’s north side. He passes on the knowledge he’s gained over the years to help his investor clients get their feet wet.

“I found my niche, helping people that want to get started investing in mulit-family housing,” Dailey says. “I help people learn how to do exactly what I did.”

Dailey grew up in Chicago with a dad who was a marine and a mom who worked the night shift as a nurse in a Chicago hospital. Despite limited resources, both were entrepreneurs who built and operated, and eventually sold, a ski resort in Wisconsin. Daily learned early on the importance of working hard and caught the entrepreneurship bug.

“My parents taught me my blue collar work ethic and I always have to be working,” he says. “And I have an entrepreneurial spirit. I’m always looking to grow and real estate is the perfect scenario for me.”

After completing his undergraduate and graduate studies at Lake Forest College and Lewis University, respectively, Dailey spent some time as a union building engineer. The compensation was good, but he wanted to be in a position where he could blaze his own path to create wealth.

When his father passed away, Dailey felt the urgency to do what he could to take care of his mother. That’s when he took the leap to develop the restaurant. He hasn’t looked back.

“I got my real estate license and started to learn about commercial financing,” Dailey says. “I learned I had more financing options if I was purchasing buildings of five units or more.”

Dailey likes to say his approach is “cresidential,” a mix of residential transactions as an agent and commercial transaction as an investor. He identified a gap in the investor market, with most commercial brokers working almost exclusively with large corporations, leaving smaller investors with nowhere to turn.

“I can help people build a $9 million dollar portfolio or sell a $250,000 condo,” he says. “I’m the ‘cresidential’ guy; I pride myself on helping people in the middle and educating them.”

For potential investor clients, Dailey has built a system that starts with identifying a budget and then looking at potential properties and locations where investors might be comfortable owning.

“What’s the best deal? The answer is every deal is going to be different for each person,” says Dailey. “When I first started investing I wouldn’t have been comfortable owning a 20-unit building in Wisconsin.”

Dailey’s system leverages the unique advantages of multi-family housing investments, which include more leverage for financing, a much more stable market than single-family residential, and a steady stream of monthly income.

“If you want to invest three million dollars in the stock market, you need three million dollars. With multi-family housing investments, other people are paying that off for you,” Daily points out. “It’s based on income and expenses, and swings in the housing market have very little impact.”

While Dailey’s knowledge of the multi-family investment market is essential for his clients, an even bigger asset may just be the enthusiasm he brings with him to the office every day.

“Selling and buying luxury real estate and investing in multi-family homes, that’s what I’m good at doing,” he says. “That’s how my brain is programmed and I absolutely love it. I bring that passion for real estate to every client I work with.”

Sean Dailey can be reached at 773-954-0942, sean-dailey.com.