6 Women entrepreneurs on how they handled the worst day of their careers

From losing investors to natural disasters, this is how these women dealt with the worst and came out stronger on the other side.

6 Women entrepreneurs on how they handled the worst day of their careers
[Images: Maljuk/iStock ; qunamax/iStock ; alphabetMN/iStock]

Women entrepreneurs are master jugglers—weaving through the inevitable ebbs and flows that starting a new venture brings. And while many milestones require celebrations, others warrant pivots. The important part of being faced with difficult, complicated and high-stake situations is having the ability to face them, head on—and with strength and confidence. Here, six brave leaders reveal the tumultuous points of their companies and how they were able to handle them and move forward.


The day Hurricane Sandy hit

Six weeks after opening Hu Kitchen in mid-November 2012, cofounder Jessica Karp felt like her and her team were getting into a groove. But then, tragedy struck when Hurricane Sandy landed on the shores of New York City. They lost power—and didn’t know when it would return. Obviously, they couldn’t cook, and thus, serve food. And all of the goods in their fridge? They had to be thrown out. Karp says they anticipated tens of thousands of dollars in lost revenue while paying rent, thousands more in lost inventory—and perhaps, worst of all, a pause in their momentum attracting customers in the competitive NYC hospitality space.

Instead of staying home, moping and worrying, the senior team rallied and motivated their staff by coming up with a solution to help locals, as well as keep their company going. “We still opened for business—albeit in a significantly abridged version of our regular offering. We boiled water for coffee and tea, sold snacks that didn’t require refrigeration, and used a small black cash box in place of a proper register,” Karp explained. “I remember that day with laughter now. We actually ended up having so much fun helping the community when almost everything was closed.”

This lesson taught Karp the importance of buckling down when the going gets rough—because more often than not, it’s inevitable. When you can, find an alternative, and try to remain positive and focused. “As an entrepreneur, you will see a lot of bad luck and bad hands. This is a reality we have to accept and be prepared to handle. I often find that I have a great influence on the morale of the organization, and having a positive, proactive attitude that day was critical,” she continues. “Rallying and showing positive energy can make such a difference—especially in a really bad situation . . . These moments often strengthen teams and relationships if you can come out better and stronger on the other side.”

The day she didn’t know if she would be able to pay rent

Two years into developing her company, Unbound, Polly Rodriguez was still in the bootstrapping stages. Or in other words, no one was getting paid. To make ends meet and get her startup running, she worked two part-time jobs, was on Medicaid, and was living paycheck to paycheck. One morning, she woke up, and the gravity of her financial situation came into reality: she didn’t have enough money in her bank account to pay rent. “I don’t come from a particularly affluent background, so I didn’t want to burden my parents with my financial reality. I felt like such a failure. I left a successful and lucrative career as a management consultant only to end up completely broke and in debt,” she says.

So, as everyone has to do sometimes, she sat on her kitchen floor and cried it out. Though she was giving everything she had, but was coming up short—and the traditional ‘fake it until you make it’ mentality of entrepreneurship wasn’t working. In an effort to figure out her next move—and talk it out—she called her best friend and confessed her predicament. She thought it was time to shut her business down—but her pal stepped in, wrote her a rent check, and told her not to give up. A few months later, Unbound took off—and she raised her first round of venture capital.


For Rodriguez, this moment—and many others—was a testament to the value of a team. “Surround yourself with people who believe in you, because there will be so many times when you don’t believe in yourself. Most of us have never started a company before, and most of us don’t come from a background where our parents can bankroll us until we figure it out,” she continued. “Starting a business feels impossible every single day, so you have to build relationships with those in your life who genuinely believe you can do the impossible.”

The day two investors pulled out, last minute

Last September, Shannon McLay, the founder and CEO of The Financial Gym, was in the middle of raising another round of capital. At the time, it felt as if everything was running smoothly and on track—but then two of her current investors pulled out of their commitment, taking $1.5 million with them. McLay had just hired four new employees because she was convinced she’d have the funding to pay them, but now she wasn’t sure how she would fulfill the payroll. Even if McLay invested all of her personal assets into her company, she never wanted to put her team at financial risk. After all, the mission behind her company was to educate women on their own monetary futures—the idea she’d have to backtrack was counterintuitive to her values.

On the day she knew she might not make the dollars line up, she made the decision to load the company as much as she could personally. “I called my ex-husband—who is still a partial owner of the company—and asked how much he could lend the company. We decided to apply for a BlueVine line of credit to help us in the future, and we postponed paying bills in cash as long as we could and put others on our corporate credit cards,” she explained. She also transferred $10,000 from her savings and was approved for a $75,000 line of credit. Fast forward a month later—and they received $400,000 in new investor money.

For McLay, this test was one of many that have appeared on her entrepreneurial journey. No matter the cause of stress—human resources, investor, business-related or financial—the best thing you can do is find an answer and keep on keepin’ on. “It would be easy to give up, stay in bed, and cry—which I have wanted to do many times over the last three years—but when I push through the stressful times, I always find something amazing on the other side,” she continued. “I’ve gained a new battle wound that I can be proud of, learn from, take with me to the next challenge, or use to help another female entrepreneur through her stressful time.”

The day her lead angel backed out

You can pick whatever saying you wish to believe: “When it rains it pours,” or “Everything happens all at once or not at all.” They both apply to Nicole Centeno’s worst day in her career. It was year two of running her company, Splendid Spoon, when she was experimenting with white-labeling to expand into wholesale business. She had made a deal with a company in Philadelphia, but the timing wasn’t ideal, since perhaps, her staff wasn’t ready. The kitchen team felt overwhelmed by the order volume, and they were cooking and packing up until the very last minute. “I saw every batch through to packaging except for the last one: the beet soup. The package wasn’t packed properly, and it was a horrible, purple mess when it arrived in Philadelphia. I still wonder if things would have been different had we saved a broth or at least something less purple for last,” she shared.


As the leader of her company, she wanted to apologize in person, so she hopped on a train to promise a full replacement of the soup situation and offer a make-good on the price. Not only was she pregnant with her second child, but she was also in the middle of raising angel capital, making for a productive trip. Until of course, another nightmare boiled over: her lead angel pulled out. ” I remember thinking, I cannot keep doing this. Instead of continuing down that route, I bought a cup of tea, sat down, and focused on my breath—a form of mindful meditation. Grounding myself in the moment really stabilized me and helped me through the extreme emotions of that day,” she shared. It was on that train ride that she decided she would not be the manufacturer for Splendid Spoon. From that point onward, white-labeling was out of the equation, and she focused all of her efforts on finding the right co-manufacturing partners.

That ‘pause’? It’s her secret ingredient to success as an entrepreneur. “Those extreme emotions and unforeseen disasters are a guarantee in this line of work. If you can create a ritual that helps you focus on the present and feel grounded, you will be able to move out of panic and begin to identify possible solutions more quickly,” she shared.

The day she lost her lawsuit

Though founder and CEO of Farmgirl Flowers Christina Stembel says there have been plenty of bad days over the past eight years of running her company, a particularly terrible one happened in late 2018. Though they’ve had legal challenges come up in the past, they found themselves in a lawsuit that went through full arbitration. At first, she wasn’t overly worried about it because it seemed like a win for them: not only were they on the right side of the issue but they had a tremendous amount of evidence to support them. And her lawyer—who Stembel calls the ‘most conservative’ person she knows—was optimistic and thought they’d come out ahead.

But after the gut-wrenching trial, Stembel was sitting at a restaurant in Memphis, TN, with some strangers, prepping for a panel, when she gets a panicky text from her lawyer, urging her to call immediately. She ducked out and learned they had no only lost but lost in a major way. “I can still remember exactly how it felt: like someone had simultaneously punched me in the stomach, sucked all the air out of my lungs, and turned up the thermostat to an unbearable temperature. I was also stuck with a slight ringing in my ears that stayed with me for a full 24 hours after,” she shared.

Once the physical reaction of shock wore down, the reality of what it meant for her company settled in. They needed to pay a very large settlement when they were already a bootstrapped company selling perishable product and operating a manufacturing operation in an expensive city. But how she handled it wasn’t rocket science, according to Stembel who shares she really only had two options: keep going or quit. The path may be difficult, but it was obvious. “I faked it till I made it through dinner, had a cocktail or two to dull the pain, and then the second I got back to my hotel room, I bawled my eyes—and heart—out. To be clear, these weren’t tears of sadness but big fat tears of anger with a touch of indignation thrown in for good measure,” she shared.


But after a few days of pity, she got to work on two things: how she was going to work it out financially and what safeguards she could implement to minimize risk in the future. “I made spreadsheets and lists. Getting everything out of my head and onto paper helps me break it down into more manageable tasks, as well as makes me feel like everything’s going to be okay even if it doesn’t feel that way in the moment,” she shares.

It’s this tactic she recommends to other entrepreneurs, since she’s found mapping to be the healthiest and most effective strategy. “After I get every little thing out of my head, I then prioritize the list and get to work. I’m not typically a list maker in life, but I find it’s the only way I can calm the crazy in my head and start working through it. Otherwise, it just spins around in my head, and I can’t seem to get out of the emotional phase and into the get-back-up-and-work-it-out phase,” she explains.

The day her company—and her marriage—failed

By the age of 30, Sophia Amoruso had achieved some impressive accolades. She was named part of all of the lists—Forbes‘s 30 Under 30, Fortune‘s 40 Under 40, Inc.‘s 500 Fastest Growing Companies, and Vanity Fair‘s Best Dressed. Her company, Nasty Gal, was even valued at $350 million. But two years later, within three months, her business—and her marriage—fell apart. Though she knew her company was struggling, the divorce came as a complete shock. To make matters even hairier, the day Nasty Gal filed for bankruptcy was the day President Donald Trump was elected into office, and Amoruso was in Australia, promoting her second book. “I was at a networking brunch where I was set to speak in front of a thousand women,” she shared. “When the death knell of your company is the breaking headline and you’re literally under a spotlight . . . what do you do? I showed up.”

She covered everything—her rise, the books, her lessons—and even ended the speech, with tears running down her face, sharing, “Hey, it was my first business, and I think I got pretty far.”

And she did. She also went on to found her current company, Girlboss. She found all of these setbacks proved to be a gift rather than a burden. To build a better company, she became more strategic about who she surrounded herself with. “Building a team here at Girlboss is different than my last go-around at Nasty Gal . . . I can’t emphasize enough how important it is to be surrounded by smart people who are in it for the right reasons,” she says.