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Milwaukee's Daily Magazine for Wednesday, Sept. 3, 2014

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In Movies & TV

Cassandra McShepard lists her current jobs as jazz vocalist, writer, motivation speaker, fashion designer, TV personality and personal trainer.

In Movies & TV

For the last 14 years of her life, she was the personal designer of jazz vocalist Phyllis Hyman.

In Movies & TV

"My statement is that I will work for joy and for love, but not for money," says McShepard. "I will cash a check."

In Movies & TV

On her positivity and future plans: "I'm still living. I'm not done yet. I've got stuff to say."

Milwaukee Talks: "Real Milwaukee" co-host Cassandra McShepard


If you're planning on interviewing Cassandra McShepard, one of the hosts of FOX-6's successful morning talk show, "Real Milwaukee," make sure you have plenty of time. When the former radio show host says, "I'm not finished talking yet," she's not kidding. McShepard has a lot to say.

McShepard is a little hard to define. She lists her current jobs as jazz vocalist, writer, motivational speaker, fashion designer, TV personality and personal trainer, among other things.

And it's true. She does all of these things with a zen attitude that comes across more in person that what you see on TV. Which is why this Milwaukee Talks goes a little deeper than most: McShepard has a vision and won't stop until it's fully realized.

We caught up McShepard recently and just let the tape roll and roll. Listen to her long enough and you'll realize that what she shares in her video blog, "This Is What I Know So Far," isn't hyperbole, it's the real deal. Enjoy this latest Milwaukee Talks.

OnMilwaukee.com: Cassandra, I think you are the definition of a Renaissance woman. Is there anything you don't do?

Cassandra McShepard: I'm a hustler. I just believe that if it comes into my mind, it's mine to do. That's how I was raised.

OMC: How have you managed to do all these jobs in just over 50 years?

CM: I was born and raised here. I had a dream of being a clothing designer for the stars, and I'd never really seen a star on the streets of Milwaukee, back in the late '60s and early '70s. After a quick marriage, at the age of 23, I left and went to the San Francisco Bay area.

OMC: Did you know anyone there?

CM: I had a sister there, and I planned to land squarely on her sofa. My mother said I shouldn't be too proud to get a job at McDonald's if I needed to. But I said, "Excuse me, I'm going to be a fashion designer." So I got there and partied for a few months, because I was newly single. Then, I literally made up my mind that I needed to find clients. I met a hot guy who became my first client, and he introduced me to a woman who had a hair salon. She featured me in a hair/fashion show. A month later, I was introduced to the late jazz singer Phyllis Hyman. As far as the fashion part of my life, the rest is history.

OMC: Did designing clothes for Phyllis Hyman have anything to do with your own jazz singing?

CM: Not really, but for the last 14 years of her life, I was her personal designer. It gave me two movie credits, numerous music videos and album covers. I traveled to New York and London. Soledad O'Brien was a client of mine; she lived in Oakland. I did an Oscar dress for her.

I was dressing these fabulous artists on stage. Watching them was magic. They could really sing, and I didn't know if I could. I could do shower and car concerts, but after my brother died the year I turned 40, I thought, "To hell with it. I need to sing." So I asked a friend if I could sing at her wedding. About a year after that, she called me and booked a gig for me on Brady Street. I don't do the club thing, but I work with a band. It's so out of body. I've put together a jazz cabaret, which is like a one-woman show. I'm doing a piece for Alzheimer's on Dec. 3 about my journey.

OMC: Tell me more about this journey. You were a California designer to the stars, but then you moved back home to Milwaukee?

CM: I had begun to experience a bit of a burnout. I was in my middle 30s, and I had gotten what I wanted.

OMC: I have to imagine this was a pretty lucrative business.

CM: Yes! The money has never been as good as that ... as of yet. I'm still breathing. But one of the things I realized as I was sitting around my house thinking about all the stuff I had to have, that these were the ties that bond. I realized that I could walk out of this house and be free. And I didn't have half the things that the people I worked with did, and they weren't happy.

What makes (me) happy? My statement is that I will work for joy and for love, but not for money. I will cash a check, but I would not work a job that I hated for money. So I came back home and walked into a kidney cancer diagnosis from my brother, who subsequently died, and an Alzheimer's diagnosis, simultaneously, from my mother. That brought all of that life to a halt. This was in 1998. I thought I'd go through my mid-life crisis early, so I'd still be cute on the back end. I never expected to stay here.

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