Prestigious Women Awards Honorees: Stephanie Toothaker

Stephanie is dedicated to innovation in development, procurement and strategy as Chairwoman of Toothaker.org. A Martindale Hubbell AV rated attorney and Super Lawyer, Stephanie is a Capitol Hill veteran, represents David Beckham’s InterMiami Soccer franchise, sits on the Bob Graham Center at University of Florida Board, and will be the first female Commodore of the Lauderdale Yacht Club.

Favorite quote: “Go on, underestimate me, that’ll be fun!” — Lisa Wlikinson

Fun fact: I have been a campaign strategist for presidential, gubernatorial, congressional and mayoral campaigns.

How do you unwind after a long day of work? Sneaking away for a phone-off pedicure is that heaven-on-Earth hour I try to fit in when I can. What I really look forward to at the end of a long week is time with my son Wyeth-Parker, whether in our Old Florida backyard along the Tarpon River, Lago Mar Sundays with my mom squad, or the occasional getaway to Ocean Reef.

What challenges have you faced in your career, and how did you overcome them? I have never taken the easy route in my career, because I want to make a real difference and change the world a little bit along the way. I came from a family of modest means and worked my way through university and law school. I fought hard after law school to carve out a niche for myself, becoming Senator Bob Graham’s first female special council on Capitol Hill. When I arrived for my first day on his presidential campaign there was a real-life “Legally Blonde” moment, but I worked harder than the boys and earned my stripes. Of course, law and lobbying can have glass ceilings for women – so I changed up my model, left the traditional law model, and opened my own boutique firm that represents billionaires and local innovators alike. I must say the biggest challenge I have faced is finding a professional/personal balance during Covid-19, and making sure time with my son does not get unfairly blended with my work as I shifted to a home office. I maintain bright lines between time on my computer and the important moments when I am fully focused on being a mom and it works for us both.

What has been the most monumental moment of your career thus far? Representing David Beckham and Jorge Mas and the InterMiami ownership group allowed me to quarterback a landmark economic, sporting, and cultural project and it was – and is – such an honor.

Based on the challenges the team faced in Miami, we literally had to bend it like Beckham with only 13 months to complete a project that would normally have a 3-4 year trajectory. Working with a visionary mayor, city commission, city manager and city attorney, we completed the P3 process, entitled the development, and built the 18,000-seat stadium in record time.

But while seeing InterMiami play professional soccer in Fort Lauderdale has been fantastic, it turns out the most important part of this project has been what we did not plan for. During Covid-19, the facility has become a food distribution site, the location of a field hospital to ensure our community had health care capacity for all who needed it, and is now becoming a regional vaccine center. It is humbling to be part of such an important project that has become so much more than it was before.

Who are your role models? My mother Nancy Gregoire, Adele Graham and Coco Chanel. They embody tireless perseverance, brilliant strategy, and effortless elegance.

What’s the best piece of advice you’ve ever gotten? Never, ever give up on anything in which you believe and don’t ever be intimidated or afraid to make a change.

What advice would you give a young woman at the start of her career? The best advice I can give is show up and not be intimidated by the status quo. Unlike when I first started out in law and politics, we live at a time when being a woman can be a clear benefit. Working together we can shatter glass ceilings, reach new heights of progress, and bring innovation to the fore that can change the way we live, work, and raise our children.

How does being a woman has impacted your career? Overall, being a woman has been a benefit to my career, but it’s all about shifting your perspective. Because of the challenges, I look at things in a more creative light, I always work harder – and I won’t take no for an answer!

When I left my previous traditional all male-managed law firm, I was warned about going it alone as a woman. Now that I took the leap, I wish I had done it years ago. As a woman and the principal of my firm, I am still very unique in my legal/political/lobbying professional space and it actually has increased my earning potential. How? We are finding our team’s niche positioning brings more cache, more notoriety, and frankly more revenue compared to a more traditional, male-driven organization.

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