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11 women executives on the greatest risk they ever took

From moving across the country to risking millions, and having the guts to say “yes” before they were ready, let these risk takers inspire you.

11 women executives on the greatest risk they ever took
[Photo: Rawpixel]

The idioms and mantras all sing the same tune: Taking a risk is often the turning point that leads to success. Whether your decision to quit a steady job for a new industry leads to a face-plant or to a few more zeros on your paycheck, the lessons you log along the way often end up being the most important outcome.

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For these successful executives, the question wasn’t whether or not to jump in—it was about how high they were willing to leap and how low they were willing to fall. From leading global rebrands and walking away from promising contracts to moving across the country in pursuit of opportunity, let these stories inspire you to, well, go for it already.

She expanded a brand globally

Though The One Group and STK already had a strong home base on both coasts—from Los Angeles to New York—cofounder Celeste Fierro wanted a bigger footprint. This meant taking the risk of expanding her restaurants to Europe and other parts of the world, even if she couldn’t be there to micromanage every move. Not only was this a financially risky move, but it included navigating cultural and language barriers, as her brand grew into London, and eventually to Dubai. “You never know if it will work out, and you truly have to engrain yourself in the respective city’s culture and food scene somehow. They key rule is it’s not just about your business—it’s about your business in context of their world. You have to get to know the city and the people and their values,” she explains.

To be successful, she had to understand it takes patience to build a name everywhere: “You have to level set your notoriety no matter how popular you are in a particular city. Sometimes people do know the name, but if they associate you with somewhere like New York, it can actually have a negative effect. That’s why is vital to keep the authenticity of the new city and balance it with your brand ethos,” she says.

She partnered with her daughter

Going into business with your best friend, your partner, or your family is tricky. Is it worth the personal and professional risk? According to  Val Griffith, cofounder and creative director of snack company Skinny Dipped, partnering with her 26-year-old daughter Breezy was anxiety inducing yet reaped rewards. “I was still paying her cell phone bill, but had to decide if I could trust her at the helm and keep the ship afloat, which she has done with a facility, aptitude, and grace that takes my breath away,” she says.

She decided to follow her gut and see what her daughter was truly capable of executing. She’s glad she did, since four years later, this dynamic duo continues to grow the company into a thriving business.

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Related: 12 women executives on how they keep their cool in high stress


She pivoted her strategy to save millions

In June 2016, Charlie Javice, the founder and CEO of college financial aid assistance company Frank, found herself faced with bad news: She needed to register her company as a credit reporting agency in all 50 states—a requirement that would cost her tens of millions of dollars. Faced with this tall order, she decided to pivot the mission completely by moving away from serving banking clients and instead serving students. This switch not only meant changing the trajectory of her business and going back to square one—but also letting go of 11 employees that she valued, including her cofounder. Javice’s company was in the red for many months, while she tried to convince her investors to adopt the new direction. It was worth it, though: After much hard work, Frank raised $10 million in a new round of funding (on top of their previous earning of $5.5 million)—and they’ve helped 300,000 students access $7 billion in financial aid in less than a year. “I learned that when you do right by people and you are passionate about your mission, even when you fail, people stick with you and believe in you,” she says.

She backed out of a discriminatory contract

Several years ago, Jordan Salcito, the founder of Drink RAMONA Inc., and Bellus Wines and the director of wine special projects for Momofuku, was dead set on opening a new restaurant. Months before their grand reveal, she realized her business partners—who happened to be male—presented a contract that was highly discriminatory against women who might start a family one day. She had a choice—to stay or to go. Though difficult to let go of eight years of work that primed her for the partnership and moving on from the restaurant industry she loved, she decided to sever ties.

Two weeks later, fate stepped in to reward her while she was working a wine event with restaurateur David Chang and two guest chefs. “Dave mentioned he was looking for someone to elevate his wine programs. After a few conversations, I realized this was the dream opportunity I never before would have given myself permission to imagine,” she says. “The beverage director position gave me creative control of multiple beverage programs as well as an opportunity to grow and manage a team, all the while learning from one of the smartest and most forward-thinking companies.”

Not only did her career excel, but she learned the valuable lesson of listening to her intuition—and to always stand for what she believes.

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She said “yes” to a job she wasn’t qualified for

Long before social media was a pioneering industry, Dani Dudeck was given the opportunity to lead public relations for MySpace—at the age of 25. At the time, she felt highly unqualified and ill-prepared for the job, but was inspired that the company’s CEO was willing to take a risk on her, propelling her to give herself the same benefit of doubt.


Related: 8 Women Executives Share The Book That Changed Their Lives


“I turned down the negative soundtrack in my head and focused on what I did know and what unique things I brought to the table. I didn’t do everything right and it wasn’t easy, but the risk paid off. I got a front-row seat to the one of the biggest internet stories around and traveled the globe,” she says. “Taking a job before you think you can handle it might mean a steeper learning curve, but the risk pays off in what you get to see and do.” She’s definitely seen and done and achieved a lot: These days, she’s the chief communications officer for Zynga.

Sally Grimes [Photo: courtesy of Tyson Food Group]

She completely switched industries

As the daughter of immigrants, Sally Grimes’s parents stressed stability and opportunity—two values that contributed to a successful career in finance. But for Grimes, the path wasn’t the right one: She craved the ability to expand her creativity and pursue a different perspective on leadership. This moved her to switch industries—a decision that to her parents was a lot like moving to Hollywood to become an actress. Even so, she decided to go for it: “I loved the idea of creating something, and then making it better. “Whether it was transforming Sharpie from a permanent marker to a cult-obsessed tool of creative expression, or Jimmy Dean from a sausage to a modern breakfast brand, I’ve had the kinds of challenges that brought together both the art and science of business,” she explains. Thanks to her bravado, she gets to do just that, now as the president of prepared foods for Tyson Food Group, where she led the charge to move antibiotics away from their poultry, among other feats.

She quit her lucrative job to start her own business

For many entrepreneurs, there is a make-it-or-break-it moment: Will they go for it, or will they decide to stay in the sidelines? It was in 1992 during a weak economy that Karen Finerman decided to leave her safe Wall Street gig to create a hedge fund with a partner. This meant trading a decent salary and job security for no income and no guarantees. To her delight, it worked out far better than she imagined: “We made way more money than I ever could have possibly made at my safe job. They say chance favors those who are prepared, but timing—and luck—go a really long way toward success,” she says. “If you can position yourself to be in the right place at the right time and are hungry and work hard, opportunities present themselves.” Today, she’s the CEO of Metropolitan Capital Advisors and a panelist on CNBC Fast Money.

Karen Raskopf [Photo: courtesy of Dunkin’ Donuts]

She took a job hundreds of miles away from her family

After spending her entire career in Dallas, Karen Raskopf relocated to Boston to take her current role as chief communications and sustainability officer for Dunkin’ Donuts. This kind of risk is common when you’re young and unattached, but Raskopf  was in her early 50s at the time with one daughter starting her senior year in high school and another one entering a prestigious arts magnet high school, both in Texas. The position was just too good not to take, though. “For the next several years, I commuted between the two cities every other weekend. I did not know if my family would be able to make it without me. I didn’t know if I would be able to make it without them—but I am so glad I took the chance,” she says. “I learned what a great family I have. I learned I could build a new network of friends and professional contacts in a new city, and I learned that being outside my comfort zone was great for my personal and professional development.”

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She pushed back a product launch for months, losing thousands

To coordinate with the launch of her product with Whole Foods and their first location in Brooklyn in 2013, Jody Levy, cofounder of  the beverage company WTRMLN WTR, says she kept her brand-new water formula off the shelves for months. This meant burning cash and missing the scorching-hot days of summer where hydration is top of mind. As luck would have it, the day the store finally opened to the public, Beyonce released “Drunk in Love” with the lyrics, “I’ve been drinking watermelon.” Coincidence, maybe—but a great one, even if she ended up waiting to release for six very long months. Today, the company continues to grow in sales, thanks to smart business practices and marketing strategy, and okay, maybe some help from Bey, too.

She joined the FBI

Today, Emily Waldorf is the senior vice president of corporate strategy for Campbell’s, but many years ago, she worked for the FBI. She calls this career decision her greatest risk since it was a long stretch from working in the private sector in telecom. At the time, she was newly married but along with her spouse, decided to make the move to Washington, D.C., to immerse herself in the unknown world of government. “It ended up being one of the best learning experiences I have ever had. I learned a lot during the process, including new skills, processes, and industries—but also importantly what I liked and didn’t like about different jobs, cultures, sectors, and work environments. Though I ultimately didn’t stay long with the FBI, it was one of my most memorable experiences, and one of the key decisions that has put me on my current path,” she explains.

Abbie Byrom [Photo: courtesy of Samsung]

She left NYC for love

After 10 years of focusing on nothing but work, goals, and professional development, Abbie Byrom, the director of global partner marketing for Samsung SmartThings, made the bittersweet choice to pack her bags and move from the dynamic streets of New York to “middle-of-nowhere” Texas to build a life with her significant other. This 2,000-mile move meant leaving everything—and everyone—in her network behind to rebuild her name, brand, and community. To say it was terrifying was an understatement.

“I was convinced that committing to moving forward personally would mean taking a step back in my career, and that I would have to sacrifice the high-paced professional trajectory I’d worked so hard to build,” she says.

But she learned what Byrom said many women come to realize: You don’t have to lose what you’ve built or sacrifice a career to invest in love and your partner. “My leap of faith ultimately led me to a dream job in a new industry with global responsibilities like I’ve always wanted, and even grow my career and skills in ways I didn’t expect with the opening of our restaurant Truth BBQ,” she shares. “My gamble on risk afforded me the chance to build a life that has balance and room for all of my aspirations, and I can now embrace change as opportunity.”

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