DEBRA CAFARO: I actually was planning to be a corporate securities lawyer, and after a judicial clerkship in 1983, I decided to move to Chicago. I still had a view that New York was the place to practice securities and corporate law. So when I came to Chicago, I wanted to find something where the legal market was the peak of the market in terms of expertise and deals of sophistication.

So I ended up going to a premier mid-sized firm that did a lot of real estate. There was a group of real estate lawyers who took a great interest in me, and I really enjoyed working with them, and they were the best at what they did nationally. That's how I became a real estate lawyer.

ROSENBERG: While we're talking parallels, I suspect my answer and Deb's answer for people of my generation and her generation would be very similar. Namely that by the time that Deb was thinking career, it was much more focused, and the opportunities seemed much more available than to people of my generation. You need only to look to Sandra Day O'Connor, and by no means do I equate myself with her. But look at her. She couldn't get a legal job when she finished law school.

CAFARO: I always advise the young professionals in any career that the most important thing is to be with people who are great at what they do and whom you respect and who will invest in you. That, to me, was always very motivating.

ROSENBERG: Deb makes a very important point. If you work with people who know their business and who are doing the top work in that area, the likelihood of being captivated by the best deals and having the most sophistication seems like a natural consequence.

AYGOREN: Did either of you encounter any difficulties in your career that you'd attribute to your gender?

ROSENBERG: Of course. I was asked a lot to serve the coffee, and the typical comment in return is that at my hourly rate, I'd be glad to. It's going to cost you $270 a cup. But in fairness to the world at that time, women weren't around. I could go weeks without dealing with another woman.

CAFARO: It would be disingenuous to say that I have not faced barriers or restrictions in my 30-plus year career that are gender-based. Everybody has advantages and disadvantages, but you take the world as it comes and you try to make the best of the package of skills and personality traits.

ROSENBERG: In the 1970s, it was very appropriate for law firms to appear very active and progressive in gender diversity, and I had a number of opportunities because I was one of the few women around. So to suggest that it is one-sided, in my case anyway, would be very inappropriate.

AYGOREN: Do you think women bring something more, or different, to a business than men?

CAFARO: I need to say three things, if I may. One is that it's certainly true that Ventas has delivered 32% compound annual return for 13 years. So we certainly represent an outperformance with a woman as the CEO, and that's very important.

Secondly, you can't generalize. It can be very destructive to assume that women managers are a certain way and men managers are a different way. Everybody brings their own life experiences, their own strengths and weaknesses to the job.

Third, I tend to be more willing than some others to protect the downside, and to ask the question: what if we're wrong, what's plan A, plan B, plan C? Many people do that, but that's one thing that some have observed: more openness to knowing we're not always right.

AYGOREN: What are the biggest differences in the industry from when you started compared to today? Obviously REITs have been completely out-performing and getting more investor attention and healthcare's getting bigger.

ROSENBERG: REITS didn't exist. When you talk about what real estate is like today versus what it was like even in the '80s, let alone the '90s, which is when a number of REITs became public, the world is totally different.

CAFARO: In general it's more global, liquid, slightly more disciplined. The REITS in particular have really changed the game and have led the way in terms of performance, liquidity, transparency, governance, etc., within real estate.

ROSENBERG: And it's permitted a whole group of potential investors to have an interest in real estate where before, it was primarily owned by investors having a significant amount of capital. By making them public companies, it gives the little guy the opportunity to play in this sector, where before that didn't exist.

AYGOREN: So Sheli, Sam Zell followed your career for over a decade before handpicking you to be his personal lawyer for his entire empire. Deb, you took over “mission impossible,” essentially.

CAFARO: It wasn't “mission impossible.” It was “mission wonderful.” I got to sit at a table where some of the biggest, if not the biggest, real estate and property deals were being done for 25 years. One doesn't have too many of those opportunities.

AYGOREN: To what do you attribute your success? What do you see as the biggest contributor?

ROSENBERG: My response would be a willingness to work hard, a willingness to control one's ego to the point of permitting others to participate totally and openly, and an opportunity to enjoy deals.

CAFARO: I would add, for Sheli, intelligence, dry sense of humor, judgment and a great way with people.

ROSENBERG: But those skills are fairly universal to people who are relatively successful. It's fair to say the most intelligent person is not necessarily the most successful, so you need a number of these skills.

AYGOREN: So how important is mentorship in this business?

ROSENBERG: Mentorship is important in life. We all have mentors along the way.

AYGOREN: And this is a question I hate to ask in this day and age, but how did you manage the whole work-life balance? What was the key for you?

CAFARO: I don't see it as work-life balance. I have an incredibly full life. I've got a husband, children, friends, work, exercise, reading, and it's a full life. You just have to make choices and decisions about what you really want, and have the supportive family, which is very important, and go for it.

ROSENBERG: By definition, I don't believe there is a balance. I'm able to look back at my career over time and know that I've achieved a work life balance but cannot say the same if I look at one day or even one week in my life. There's a situational assessment each time I spend more time at work than home and vice versa. Awareness is the key to a fulfilled life. Certainly, there are more resources available and with that are more options in striving to achieve this harmony.

AYGOREN: Where do you see your future? Be it with your companies or with the industry in general.

ROSENBERG: It's going to get bigger.

FAST FACTS

Favorite movie?
ROSENBERG: Blazing Saddles

Favorite Book?
CAFARO: Pride and Prejudice or Anna Karenina.
ROSENBERG: Anything that's a distraction.

Favorite vacation spot?
CAFARO: Capri.
ROSENBERG: Caneel Bay on St. John's Island.

What's one thing about you that people would be surprised to learn?
CAFARO: I was at the Immaculate Reception. I'm a massive Steelers fan. Black and gold all the way.
ROSENBERG: I'm a big sports fan as well. I love basketball particularly, but I also enjoy football.