Windy City Times: Tell me a little about your background.

Jason Rosenberg: My mother was born and raised outside of Great Neck [ New York ] ; my father was raised in [ New York City ] . They moved to Chicago when I was little. My sister, Rebecca Rosenberg, is actually my Chicago-based partner; she has nothing to do with New York. Then, we have a partnership with a firm in Philadelphia and there's one in New Jersey.

WCT: So your business is in four different cities?

JASON ROSENBERG: Well, kinda. The base is in New York, and I have a partnership with a firm so we refer them leads. When they close, they give us a percentage. And it's all Internet-based, which is great.

WCT: And you spend your time here in Chicago?

JASON ROSENBERG: Most of my time, as of recently. I want to spend more time here. Now I'm hiring people over the phone. Being a virtual company, I can be in Seattle; my agents do the physical work ( showing the apartments and things like that ) ; here, my sister and I both show real estate.

I enjoy it here [ in Chicago ] ; it's easier. It's just a nicer city. I love the open water and beaches. Once you take the glamour out of New York—which lasts for two days—there's really nothing else. I love that city, but it's an unnatural place to live; people need some greenery.

WCT: Yet your business is based there...

JASON ROSENBERG: It was easier and, believe it or not, cheaper to open up there.

WCT: Gotcha. And how many people do you employ?

JASON ROSENBERG: They're commission-based agents. We have about 16. We just restructed everything, and we're hiring about one every other day now. Agents are easy to hire; there's no out-of-pocket money in the beginning.

I get about 1,000 leads a day, most from New York. I also own lots of Web sites—about 1,000 domain names. Agents are not working for a fancy name, but we give them leads. You can go shopping at Saks Fifth Avenue and walk out with nothing, or you can go to TJ Maxx and get a lot of stuff. We're not a full-service brokerage; in the end, it doesn't matter what name you're under [ for the most part ] .

WCT: So it sounds like your business is doing quite well in this economy.

JASON ROSENBERG: [ Knocks on table ] We have not hit a downturn, because of the Internet. The Internet keeps us going. So many other firms put money into promoting themselves. People don't care what I look like or how many houses I've sold—customers stick with us if we show them good service. It's like working with Starbucks. We're there to serve the people.

WCT: How did you come to be interested in real estate?

JASON ROSENBERG: Chaz [ Walters ] . I meet him when I was 20. We were really good friends. He's a great guy and an inspiration. I used to work at Hot Property [ Residential Brokerage ] , and he's an excellent agent. He continues to dominate the market.

I operate very differently. We don't quite get the high-end people, and that's OK. Even in New York, the average sale price is $800,000, which is equivalent to about $300,000 in Chicago—it's the lower-middle end of the price spectrum. [ Laughs ] I can't afford that right now, and if I never could I'm fine with that. But I'm having fun and I have nothing to prove to anyone.

WCT: What are the best and worst aspects of your job?

JASON ROSENBERG: [ Laughs ] Money—both of them. Sometimes it's rolling in and it goes right back out into Web sites. We need to keep up with the most high-tech things, especially since we're a virtual company. My sister and I used to be with another company, Prospect Equities, here; we were the top agents there. She's got the good rapport with the clients. She's gets the leads and handles clients.

Money's bad when it's not coming in; luckily, we are doing well. But we had bad times a few years ago. I'm pulling in quite a bit each month, but it's not 2006, when it would be $20,000 a month—so I've had to curtail my spending.

We've lasted in an industry that so many people have fallen out of—but maybe some of those people were not meant to be in it. It's a difficult industry. You have to be so aggressive, and be willing to take a lot of crap.

WCT: So would that be your advice to people thinking of entering the real-estate business?

JASON ROSENBERG: Yes. Be aggressive; follow-up is extremely important. Never be nasty or rude to your clients, even if you want to be.

The higher-end buyers are actually a bit nicer; they know how to treat people. I don't know why that is.

WCT: What do you do outside of work?

JASON ROSENBERG: I love to exercise; I work out every day for about two hours.

I've always been really insecure with my looks, and I've had some cosmetic surgery—liposuction [ and ] a nose job. I'm a nice person, but I keep thinking I'm not attractive. However, I have a lot of confidence when it comes to business—and you can type all this up. I don't think I'll ever be a completely secure person.

WCT: Is there anything you wanted to add?

JASON ROSENBERG: I did five cartwheels on the way in here—just kidding. Seriously, we have too many leads and not enough agents, so I'm actually interviewing someone today. [ Also, ] I'd like to expand my partnerships into other cities [ such as ] Toronto and Vancouver.

And I'd like to build my New York business to the point where I can sell it. If I won the lottery, I would not be one of those people who'd keep on working. I'd be content with working out and doing nothing [ else ] .

See www.jasonrosenbergsgroup.com .