Location: Monterey, CA
Age: 54
Marital Status: Single
Education: Self-taught
Did she ever. Today, Cheryl is a wildly successful real estate entrepreneur with two businesses under her belt and two gorgeous daughters who work with her. A truly self-made woman and a true beauty, her passion is her latest project: Coaching other FOFs to navigate the dating scene.
How old were you when you started the real estate business?
33
From the time you were 19 till 33, what were you doing?
I got into real estate in 1981. I started to realize, ‘Wow there’s a whole other world out there.’ I always wanted to have financial independence, but wasn’t quite sure how to do that. Without a formal education I knew I had to get into some type of a business like sales. So I just jumped into the real estate industry and built my business from there.
Did you ever remarry?
No, I chose not to. I wanted to raise my kids on my own. I wanted to make the decisions for their lives and the path that we would go down. So I dated a lot, and that’s where this other business has really evolved.
Tell me about your new business.
I empower women to go out there, work a room, and become comfortable with being single. I had to empower myself throughout my life; raising my children, coming from nothing and building myself into a very successful woman. I’ve learned these skills through experience. Now I do private sessions with clients as well as speak to groups.
Is this business geared towards a specific age?
Yes, 40 and over. Our generation has become very educated; we fought to get here, to have our independence and to be equal with men in so many ways. But when it comes to dating, a lot of us are still “magically thinking” that a knight in shining armor is going to come to the door. We’re 50 years old, but we’re still thinking like 13-year-olds. All of us have said, ‘I only wish I knew then what I know now.’ But now we do know.
Tell me about your style.
Classic with an edge. I’m eclectic. I can be very, very sporty. I love to go hiking and get sweaty and dirty but then come home and put on the dressiest black-tie gown.
Whose clothes do you like?
Prada. Alberta Ferretti. But my favorite designer is Chanel.
Where do you like to shop?
Pacific Tweed. They have the best customer service and staff. And they listen to their consumers: ‘How are we doing? What do we need to buy?’ If you need something specific they’ll hunt it down for you. It’s very rare that you find a retailer like that.
Who influenced your style?
So many people. I have always sought out trainers, teachers and coaches. Fifteen years ago I hired a gal from Los Angeles to come and just rip my closet apart, redesign it and take me shopping in southern California. She helped me get to the next level.
What’s a great book you’ve read.
I liked Conversations With God—one, two and three—by Donald Walsch. I am a very spiritual person. I believe that there is a higher power and we’re here for a reason. There is nobody else responsible for our journey in our life but us. My mother used to always say, ‘you pull yourself up by your bootstraps and you get back on that horse.’ Conversations With God talks a lot about that.
Believe me, I’ve had my ass kicked more than I care to talk about. But by having your ass kicked and coming out on the other side, you grow and mature in all areas of your life.
What’s your secret favorite place in Monterey?
I love to hike in Big Sur. It’s beautiful—you see the ocean and on the other side you see the trees and the hills and watch the sunset. I hike there and then go back down the mountain to Nepenthes for Bloody Marys.
What inspires you?
The next thing. What else is there in life that I haven’t seen or touched yet? Where else can I go? What can I do? And this is what I try to teach women. We inspire ourselves. What is it that you want to do next?
Tell me your beauty routine.
I wash and moisturize every day with a line called Nutrimin. It’s a very effective, all-natural product. They have different lines depending on what it is you’re looking for: detox or anti-aging, etc. As we get older I think we need better products.
Do you have a signature perfume?
Narciso Rodriguez. People ask me, “What is that? It’s so fresh.”
Tell me your favorite restaurant in the area?
19 at Pebble Beach. The best of the best food. It overlooks the ocean—beautiful views. I’ll go in by myself and sit at the bar and have a glass of Rombauer. They have this incredible hard-boiled egg appetizer with rock salt and caviar. My mouth is watering just talking about it. I’ll have that and an arugula salad. I can’t describe how good it is.
What’s you’re secret favorite place.
Portofino is the most romantic, beautiful city. You can take a lovely little hike from one side of the island to another—I just love it.
What’s your biggest indulgence?
Oh my God, so many. A great place with a bunch of friends, way too much food and way too much wine.
What is the single most important thing you’ve learned in your career?
This too will pass. The tough times will pass and the great times will pass. Try to stay present in whatever is going on. Face it, whether it’s good or bad and then learn how to let go of things and move on. That’s something I have to work on everyday.