Ann Kaplan: Lead, Follow Or Get Out Of The Way
Strength, independence and confidence are Ann Kaplan’s secrets for success.
To say someone is accomplished can sometimes be misleading, as it’s in the past tense, as if their journey is done. Dr. Ann Kaplan is an accomplishment — in progress.
Award-winning entrepreneur, CEO, academic, lecturer and motivational speaker, author, designer, television host and personality, and devoted wife and mother to eight kids, Ann Kaplan displays glamorous style and chic sophistication, while bursting with confidence and possibilities that took their root at a young age.
“In my early teens, I said to my mother I will never work by the hour,” says Kaplan, in a recent wide-ranging interview with Dolce. “Whatever I do, I needed to make widgets; I just didn’t know what the widget would be. I’ve always been a self-starter. I’m very confident and like my mind. I became independent at age 14, and my whole life has been a testament that I need to stand on my own two feet. Today, I embrace everybody and live a life of extraordinary happiness.”
Speaking with Kaplan leads one down a labyrinth of life adventures full of triumphs and tragedies, all of which have shaped and guided her, with success as its common denominator. Perhaps not what she envisioned as a child, but not that far off.
“I don’t think we can envision our lives, but I always knew I’d be successful and not dependent on anyone,” says Kaplan. “I always felt completely in control of my life, and I wasn’t going to be owned by anyone.”
With a PhD in business and an MBA in business and finance from the University of Toronto’s Rotman School of Management, today Kaplan is CEO and president of iFinance Canada Inc., the parent company of Medicard, Petcard, Dentalcard, iFinance Tech and iFinance Home Improvement — a North American consumer finance company that she took from start-up in 1996 to now being one of the largest consumer finance companies in Canada.
These successes have garnered her more than 40 business awards, including being named the Canadian Woman Entrepreneur of the Year twice, and being recognized as among Canada’s Top 100 Women in Business, as well as among Canada’s Top 100 Most Powerful Women. It’s especially gratifying while succeeding in the usually male-dominated world of high finance.
“I don’t think of myself as a woman in finance; I’m a person in finance,” says Kaplan. “I once walked into a boardroom filled with 14 men, and one of them took me aside to say, ‘I hope this isn’t too intimidating,’ to which I replied to him, ‘No, I’ll try not to be too intimidating.’”
The man’s comment is even more bizarre considering the incident didn’t happen in the 1960s, but about six years ago, showing the male-female gap in business still exists, and equality may be some time away.
“We’re likely still a long way away, but women have made great strides,” observes Kaplan from her front-row seat. “I have more than 100 employees, and I look at people equally, judging their skills and values. I would never hire someone just for a diversity or gender balance; I will hire the right person.”
Another of those strides is that the United States will soon have its first female vice-president with Kamala Harris, upon whom the world should look for the right reasons. “Just focus on her values and how well she’s done and how’s she going to lead, rather than the fact she’s a female. She’s the right person,” says Kaplan.
Kaplan’s many business successes have all been the product of a large brain and a passion and determination to do the required heavy lifting to ensure that success. “There is no such thing as luck. Luck is when opportunity meets preparedness,” she says, confidently. “I prepare myself for the opportunity, and you have to know how to recognize an opportunity and know how to take it.”
Even being one of those women who “have it all” as a mother, business leader and striking the right work-life balance, Kaplan still sees younger women struggling with questions about the balance, and it’s a message she delivers strongly as an in-demand motivational speaker on the lecture circuit.
“I’m Very Confident And Like My Mind. Today, I Embrace Everybody And Live A Life Of Extraordinary Happiness”
“After speaking, young people come up to me, questioning whether they can have both a life and a career, so some people do still think that way,” says Kaplan. “I tell them to be who you want to be and find the person to be with who encourages that; otherwise, walk out the door, because that person will not change.”
The fierce independence Kaplan possesses is another key part of her message to younger people, who she strongly feels should take greater personal responsibility and not unwittingly block their own way.
“I teach them how to be successful in spite of yourself and how to get out of your own way,” she says. “You cannot be defined by how you were brought up or what happened to you. You’ll be defined by what you do going forward. It’s us that can get in the way of ourselves. If you change your attitude, you can move forward. Respect your parents, but don’t be what your parents want you to be, because you’ll limit yourself. You can exceed that. There are no limitations to what you can achieve. I get a lot of nodding heads when I say that.”
It is a message Kaplan uses in one of her books, How to Be Successful in Spite of Yourself. It’s been said that everyone has a book in them. Kaplan has five — and counting: If You Don’t Laugh, You’ll Cry; Best Practices; The Internet (about marketing yourself online); and her significant Fashion Cares: 25 Year Retrospective Book demonstrate her varied and intense personal interests. One hundred per cent of the proceeds of Fashion Cares benefited the AIDS Committee of Toronto and the Elton John AIDS Foundation. “I really understand the struggles that exist today, and the HIV/AIDS fight is not over,” says Kaplan. “I’ve made a lot of friends in the fashion industry whom I cherish, and I’m very passionate about this cause.”
Kaplan’s latest offering is Eating With Purpose, due out in March 2021, which she describes as avant-garde cooking and incredible recipes. It is part of her passion that everything you eat should help your body, internally and externally. “I make my own sauces and pastes, and I demonstrate in this book how to do that. We should all be eating foods that are wholesome and right from scratch, and the book includes fun, funny and fashionable pictures, and every recipe has a bit of humour attached,” she says.
Humour is a baseline emotion for Kaplan. “I love intelligent humour, and I love great banter and wit, and I love to laugh,” says Kaplan. “Every day, I love to do things that make me laugh. The greatest dinner parties are not the food on the table, but the people at the table.”
Always co-hosting at that table is her beloved husband of 20 years Stephen Mulholland, one of Toronto’s top plastic surgeons. Their French château–styled home in Toronto’s exclusive Bridle Path area was featured when Kaplan starred on the hit TV show Real Housewives of Toronto in 2017, which is just another one of her many notable accomplishments.
Together, Stephen and Ann have eight children, two of whom are solely hers, another two are Stephen’s, two are theirs together and two they took custody of when her sister died. She suffered another loss earlier in the pandemic when another sister died, and there could be no funeral, which just added to the surreal nature of this most challenging time. “My heart has been so heavy, but I didn’t want grief to define me,” Kaplan recalls. “This year has been a year to be transparent and upfront with each other and to not spend a minute with people who are cruel, mean or hurtful, and I have no problem telling people like that in person. I am realizing this year how important every moment is, and every call and every conversation. I realize that much more now. I’m being the person I want my children to be.”
It’s not the only thing about 2020 that surprised her. “I was really surprised I like my husband,” she laughs. “I love him dearly, and we’ll be married forever, but I wondered how we’d do together staying home. I realized how much I enjoy him, and it’s been a revelation. I like him, and I enjoy him, and it’s been wonderful.”
It’s only part of the learnings that we can all experience from this time, especially younger people. “Stay strong and get creative by giving yourself an outlet using another part of your brain,” Kaplan advises. “There are creative people coming out right now who can do more. Just because you can dance, doesn’t mean you can’t sing.”
Ann Kaplan is an inspiring dynamo who takes a “lead, follow or get out of the way” approach to life, and even with everything she has accomplished, it is hard not to have the feeling she’s just getting started.