Crocker said it was Cafaro's affinity to know when someone is bluffing that helped her at the negotiating table. She also knows when to step back and when to push.
"She would go to creditors meetings, and if she didn't like what they were proposing, she would basically say, 'No, this is what we are prepared to do,'" Crocker said. If the other creditors didn't agree, "She would say, 'That's too bad, I guess we would see everybody in court.'"
Cafaro loved the challenge.
"I really am attracted to difficult and complicated situations, and some of the jobs that I've had had those characteristics — particularly the Ventas one, which was really, really difficult in the early days," Cafaro said.
The first years were crazy, Rosenberg observed.
"As I recall, (Cafaro) was always in motion — I don't know if she ever slept," Rosenberg wrote. "It was not uncommon to get an email from her showing it was sent at 3 a.m. (I) remember she was trying to give credibility to the company, which at that time was not known or respected."
In 2002, a year after Vencor emerged from bankruptcy protection as Kindred Healthcare, Cafaro focused on growing Ventas' portfolio and staff.
"That's one mandate Debby pushed through: Let's try to grow. Let's diversify who the different tenants would be to try to diversify away from Kindred," said Eric Gordon, then a manager of real estate investment at Ventas.
An all-in-one package
Ventas' first merger came in 2004, when the company acquired ElderTrust. By 2009, Ventas owned 505 properties — nearly doubling the amount of properties Cafaro had started with. The number of tenants grew from one to 22.
"Throughout my career I've tried to think about my decisions, about whether to do things or not to do things with this upside-downside analysis. If I don't succeed, what are the consequences of failure? But if the company succeeds, and does well, what is the upside? What comes from that?" Cafaro said.
Gordon, then in his early 20s, said that as he meets other chief executives, his admiration for Cafaro, whom he calls engaging and super smart, only grows.
"Executives are good at turning things around, managing or growing, and not often do you find all three qualities in a person," Gordon said. "(Cafaro) has the three abilities all wrapped in one package."
She also showed foresight before the downturn. In mid-2007, "while things still seemed quite fine," Cafaro said she took a hard look at the real estate market and saw troubles ahead. After the company completed its fourth acquisition, she told her team to slow and get defensive.
The company raised $1.1 billion of equity, sold assets, refinanced its debt and increased its lines of credit. As a result, Ventas pushed ahead through the recession as other REITs struggled.
In 2008, Cafaro moved the company's headquarters to Chicago. That allowed her to spend more time at home in Winnetka, though work often follows her there. When the weather is nice, she plugs back in from the back patio overlooking the pool and surrounded by trees.
As the company evolves, the challenges of leadership change too. She now must motivate a much larger staff and unite it in the cause of making Ventas successful, she said.
"That's a very different exercise from what I did at the beginning, which was more about a task and less about leading an organization," Cafaro said. "And so the challenges are different, and I think it is wise to realize that one can always fail and make mistakes, but that you have to stay really energized about moving forward and not let that hold you back."
email@example.com Twitter @writeralejandra
Music tastes: Country, hip-hop/soul, opera.
Current books: "Cutting for Stone" by Abraham Verghese and "The Greater Journey: Americans in Paris" by David McCullough.
Favorite phrase: Fortune favors the brave. "If it seems that the upside far outweighs the consequences of a potential failure — because everyone fails at one point — then it suggests that you should go on ahead and do the thing you are considering."
Where she'll visit when she gets time to travel: "Thailand/Cambodia, Africa, Barcelona, Spain, Greece, China … and so many more."
Favorite sports team: Pittsburgh Steelers.
Advice for young women: "Take intelligent risks with your career."
Does she worry that her children won't have the same drive she does?: "I think it's impossible for children who grow up under different circumstances to have that same kind of drive to do better. … I do everything I can to encourage our children to value work and value, really, making the commitment and making sure that they are putting out; that they really are trying."
Debra Cafaro, CEO of Ventas