Roberta Weber

August 2025 Issue

by Lesley Kyle
Photography (top) by Lindsay Pettinicchi Photography, LLC

Roberta Weber knows how to get things done.

Born and raised in the Badger state, Roberta attended and graduated from the University of Wisconsin–Madison with a degree in speech and hearing pathology. She moved to Chicago where she raised a family and began her 40-year career in healthcare. She managed a radiology department and a large orthopedic office before becoming the Physician Administrator at Highland Park Hospital for just over 10 years. In this position, Roberta gained valuable experience in physician relations and quality, patient-focused services. Moreover, she built an enviable reputation and became well-known as a trusted, respected, and discreet physician liaison and advisor.

At the age of 59, Roberta found herself at a crossroads in life. The community hospital where she served as physician administrator was acquired by Northwestern Healthcare. Roberta knew job cuts were imminent, so she quickly accepted another job offer. The hospital’s physicians threw a lovely going away party for her. During the party, one of the attending physicians discreetly approached her about an exciting idea he had heard at a recent medical conference—concierge medicine. The doctor loved the idea but didn’t know how to implement it. He asked Roberta if she thought she could do it.

At the time, the medical profession had transitioned to a climate where doctors were forced to see more and more patients in less time. Many loved their patients but hated the business aspects of their professional practices, finding little time for neither their patients nor their own families. They were also frustrated by the restrictions imposed by insurance companies. Concierge medicine is a model where members pay a fee for greater physician access and enhanced services. Also known as boutique medicine, these practices enable physicians to spend more quality time with their patients.

Roberta thought it over and agreed to do her due diligence on the concept. She learned that only one company was assisting physicians in transitioning their traditional practices to the concierge model. While most of her friends were planning for retirement, she was seriously considering starting over with a new ground-floor business. And the concierge medicine research kept her intrigued and busy. “My kids were grown, I was newly divorced, and I had no social life, but I didn’t care,” said Roberta. As a consultant, her first client was the physician who had approached her at the party, and their partnership was wildly successful. Sensing a larger opportunity, Roberta thought to herself, “This is a business to be had!”

Establishing trust with the physicians she worked with was the key to her success. “These doctors, whether I agreed with them or not, knew I always heard them.” Her business, Specialdocs Consultants, grew exponentially as physicians from around the country sought Roberta’s expertise. Thirteen years later, she sold the company to a private equity group and retired.

But Roberta’s passion for adventure didn’t end there. She had always had a desire to obtain her pilot’s license. “Every time I’d get on an airplane,” said Roberta, “I’d look in the cockpit and think, ‘How cool is that?’” The morning after she sold Specialdocs Consultants, Roberta made a decision to pursue her pilot’s license. She found an instructor who was willing to take her on at 72 years old, and her next journey began. Roberta had already decided to let the dream go if she couldn’t pass the required and very difficult written test on the first try. But she passed it with flying colors, and after nearly another year of flight training, she passed her check ride as well.

“Pilot training is grueling and requires a tremendous amount of studying,” revealed Roberta. “Studying at 72 isn’t the same as studying in college. It takes longer to process information as we age.”

Her love for flying soared. At age 75, Roberta flew an L-39 fighter jet with an instructor. With a love of travel and the thrill of new adventures, she went skydiving at 78.

With that same verve for new and exciting, Roberta didn’t hesitate to move South and become a full-time Islander, preferring balmy ocean breezes to windy, wet Chicago winters. “I enjoy the mild change of seasons and happily no longer own any business attire,” she said. “I’m quite comfortable here in denim and flannel when the seasons permit.”

Through both her words and examples, Roberta is a champion who reminds women to chase their dreams at any age, at every age, in fact, don’t even care about age! “You have to keep your life interesting and remain relevant. You are always learning, you are never finished!”

So, what’s next for Roberta Weber?

“I’m game for pretty much anything.”

Up Close:

Fun Fact: Roberta is a gearhead who loves sports cars and has only driven manual transmissions.


Adventure: Safaris in Africa, zip-lining in Costa Rica, trekking in Rwanda to see silverback gorillas, and seeing giant tortoises and blue-footed boobies in the Galapagos Islands.

Family: Her children, grandchildren, great grandbabies, her partner, Michael and their sweet, 5-year-old Havanese dog, Henry. 


Motto: “You only go around once in life.
Go for it!”