How 5 Femalepreneurs Defied Failure to Start Their Hustle
October is a month dedicated to female empowerment across several fronts. It’s Breast Cancer Awareness Month, Emotional Wellness Month, and National Women’s Small Business Month. While Emotional Wellness Month conforms regardless of the gender people associate themselves with, research shows that women are most at risk for emotional burnout at both regular workplaces and in entrepreneurship. So in a particular way, the trio of causes is intimately interconnected: when we heed women’s health, emotional wellbeing, and professional success, we raise women who’re up for anything.
This National Women’s Small Business Month, we talked to the femalepreneurs who learned how to effectively combine these three staples of wellbeing and build them into a balanced personal life. Their lessons didn’t come easy, either in life or business — either because of an initial failure or because they had to push through a wall of challenge. Yet in complete defiance, these women took their métier from scratch to thriving while fighting more than one battle. Fighting and winning.
Here’s how all of us, regardless of gender and entrepreneurial experience can celebrate the courage of women entrepreneurs and get inspired by their leap of faith.
Renee Powers: When one door closes, another opens
When we imagine our life going a certain way and think we’ve got all the details filled in — never relax. Quite unapologetically, that may be exactly the moment when the Universe gives us a kick you-know-where, and in a totally different direction than we sought. How it does this is usually brutal: snapping a door shut right in front of our face. For Renee Powers, founder of Feminist Book Club, the “aha” moment coincided precisely with a snapped door — and a window that opened into another reality.
“I didn’t start off as an entrepreneur. I was planning on finishing my Ph.D. and pursuing a career as a professor and researcher,” Powers says. “But after 8 years in grad school, I failed my dissertation proposal three times. I finally dropped out of my Ph.D. program and funnelled everything I had learned into a successful business.”
Currently, Powers runs the Feminist Book Club, one of the most popular book subscription boxes recognized by Oprah Daily, Marie Claire, the Tory Burch Foundation, and Readers Digest, among others. The club has just announced its exclusive collaboration with actress Gabrielle Union.
“I definitely think I failed up, not down”, Powers laughs. But at the heart of that statement is what she earnestly credits as rudimentary to entrepreneurial success: the patience to see through closed doors.
“I truly think that success as an entrepreneur, especially in the digital age, requires a great idea, a deep understanding of your niche, integrity, consistency, and time. There are very few overnight successes. Sometimes patience is the most necessary skill.”
“Dr. Brene Brown is my role model for countless reasons. Like my own background, her career began in academia and everything she does is rooted in her rigorous research. But what I admire most is her humility and generosity of spirit as she continues to build upon her success.”
Nicole Johnson: There’s no such thing as one-size-fits-all
Business is one of the greatest grounds for metamorphosis, transformation — secondary, perhaps, only to fairy tales. We know how awesome products are born out of an untapped market need and an ability to fill in that need. But sometimes, to close a market gap, you don’t need breakthrough ideas. Like Nicole, you may just have to zoom in on a problem, and the humble pumpkin will transform into a magic carriage.
Nicole Johnson was a sleep-deprived first-time mama when her business, The Baby Sleep Site sprang out of a personal quest for motherhood peace. From researching sleep methods and baby developmental needs to scheduling routines, Nicole went to extreme lengths to figure things out — just for herself. What she didn’t realize is that this would be just the “pep talk” before helping thousands of women.
“What I didn’t like about all the books out there is that they contradicted one another and didn’t fit my parenting style,” Nicole says. “So, I overcame my son’s sleeping issues in a way that matched my own parenting style, and knew it was my mission to help other tired parents ‘find their child’s sleep’”.
“I started to help other parents on a message board over 12 years ago and after enough people told me that I should write my own book, I started thinking maybe they were right. I started a blog and using my technical background as a computer programmer, a Sleep Helpdesk where I help fix other parents’ sleep problems faster than I could fix my own. I started the website in 2008 two months after the birth of my second son and it grew faster than I imagined. Now, The Baby Sleep Site gets over 500,000–1 million visitors to the website each month.”
Managing a bustling business comes with its own challenges — and in order to not be (ironically) sleep-deprived the second time around, Nicole had to learn again. This time, not just technology to delegate work effectively between her team, but psychological balance to scale back in order to go forward.
“One of my main business challenges has been not trying to help everyone I can. With so many website visitors, you want to help everyone who is having problems but that leads to long hours and burnout. I love to help families personally but also need to watch my own work/life balance. Hiring an assistant and other sleep consultants has been the best decision I’ve made. Not only can I comfortably take a vacation once or twice a year knowing the business will function well in my absence but I’ve also given other moms the ability to work from home (even before it was considered more normal) while also raising their own families. This has been one of the most rewarding things I’ve ever done in my life: helping parents with their problems while also providing employment for other moms.”
“My main motto is that there is no one-size-fits-all approach that works for every baby and we need a unique approach for each unique baby. Their age, temperament, and personality will all come into play. You can use this same motto for [business and] many things in life as well. What’s right for you might not be right for me and vice versa. And, that’s OK! There’s no right or wrong, only what’s right for each individual.”
Donna Ralston: Do good to as many people as you can
When Donna Ralston opened up non-profit organization South Metro Medical Equipment Loan Closet, she dreamt of more than launching a business. She was fulfilling a personal mission to meet the needs of the most vulnerable part of her community — people in need of medical rehabilitation equipment who couldn’t afford the expenses.
However, at one point her own business needed help. In business since 2016, the Denver-based NPO faced troubling times in spring 2020 when COVID-19 forced it to close its doors for several months. Far from breaking its spirit, however, the pandemic eventually brought several adjustments to the organization’s operations.
“I was an executive director for several non-profit organizations for over 20 years and used the skills I had to establish and operate this organization,” Donna says. “So I was able to organize the activity, the paperwork, the insurance, the legal stuff, and coordinate the training of volunteers so everyone has a good idea of what they’re supposed to do.”
NPOs function differently from regular businesses since people power is literally their fuel. It was this “togetherness” and groundedness in her own faith and values that kept Donna going throughout the pandemic.
“[When running an NPO] you have to recognize volunteers for their effort, their skills, and the time and effort they put into assisting the organization. Our volunteers are very faithful and dedicated, and they really like doing the jobs they’ve chosen to do.”
Donna reminds women who aspire to open up nonprofits that business skills and innovative technologies (like the business phone system used by this NPO) run hand in hand with deep personal values. The way you make an NPO work is by “using the skills of your people and building on them” while using the networking opportunities, especially word of mouth, within your community to grow.
“Being a Christian, I really believe you should do good for as many people as you can, in as many ways as you can, as often as you can, for as long as you can. That’s been my motto. I’ve had a lot of mission trips overseas and mission projects locally. South Metro Medical Loan Closet evolved out of my passion and the mission to help people.”
Eden Cheng: You are who you surround yourself with
When we start a business, it’s easy to get caught up in the anticipation and enthusiasm. A first-timer entrepreneur’s vision feels unbounded and we entrust it to others hoping that everyone has our best interests at heart — often enough, without taking account of the people and circumstances. But just like hearts, business plans can get cracked with the wrong people.
Eden Cheng, co-founder of software company PeopleFinderFree, is one entrepreneur who’s learned to be selective through the tough lessons of initial failure.
“When I launched my first software company a few years ago, I just wanted to get the business up and running and I made bad decisions about who I recruited,” she says. “At the time I was so filled with over-eagerness and excitement that I wasn’t always careful to have the right people around me.
As a result, Eden faced a problem that leads to the crash of many startups: her team wasn’t a team of visionaries but just people who’ve “come along for the ride”. “It was inevitable that we suffered extended project delays, which ended up costing me a significant amount of money in the process, and ultimately, stalled the project so much that we had to shut things down permanently,” she says.
Now well into her second and successful startup, Eden holds the lessons from that initial failure as “hard but valuable”.
“Now, I make sure to take my time to hire people that are genuinely interested in my success and understand what we do here,” she says. “They have to be highly skilled at their given specialties and be able to pull their own weight, while I focus on handling on my own. Anything less than that is not acceptable. And as harsh as that may sound, I have learned to be okay with that because I can attest to the fact that the quality of your team really can make or break you.”
As a female founder who has experienced most of the struggles of femalepreneurship, Eden says she’s often battled the urge to call it quits. What helped he through was a strong support network of family, friends, partners, and coworkers in line with her company vision.
“A founder’s strength doesn’t start in the workplace, it starts at home, with your personal life. And, on the professional side of things, this also involves making sure that you always hire the right people for your business, not just based on skills and qualifications, but on personality and character, as well.”
“Jessica Alba is more well-known for her work in film [but] over the past few years she has transformed herself from being a Hollywood starlet … to becoming the co-founder of a billion-dollar company, whose mission of selling chemical-free diapers, wipes, cleaning products, and more placed her in business magazines and lifted her into the world of successful startups. What impresses me the most is the fact that she built a purpose-driven business that does well to deliver the eco-friendly products that their customers needed all under one roof by staying true to environmentally sound practices.”
Christina Kaye: Rule out insecurity and fear
We live in a culture that is entrepreneurship-hungry. Among the younger generation, 63% plan to start a business at some point in their lives, 99% of all businesses are SMBs, and digital businesses take as little as a few hundred dollars to launch. All this makes aspiring business owners pretty confident — until their first brush with reality.
Christina Kaye is a former trial and litigation paralegal who made a pure “leap of faith” with her digital coaching business, Write Your Best Book. In 2019, challenges kept on piling as Christina’s law firm — and with it, her steady 22-year law career — found itself on the verge of shutdown, her difficult marriage ended, and she found herself on the brink of unemployment with two teenage daughters. She was certain that her plan would find support.
“I decided to at least try to turn my 10-year side hustle as an author coach, book editor, and writing instructor into a full-on business,” Christina says. “[But] when I shared this decision with my circle of friends and family, the reaction I received in response was NOT what I had hoped for. Most stood strangely quiet and never offered much of a convincing “go get ‘em,” but more than one person made their opinions known, loud and clear.”
Instead of a warm word of encouragement she hoped for, Christina met with a wall of skepticism. “[I was told things like], “No one who ever starts a business is successful the first time around’, ‘What are you going to do when it fails and you can’t support yourself, let alone the girls?’, “You’ve never run a business before. How can you possibly expect that to work?’ And my all-time favorite, ‘Why don’t you find a nice, steady job at the grocery store?’”
Add to that a global pandemic launching almost in line with her new business, and the circumstances would’ve been enough for most people to give up, but not Christina.
“Despite the not-so-favorable circumstances under which I started what I call my ‘Act Two,’ and in direct defiance of those who couldn’t be bothered to even feign support, I had earned my first 6-figures before the end of Y1Q3! Now, year two (my second 6-figure plus revenue year) is closing soon, and to date, I’ve helped over 300 authors successfully write and launch their books, I’ve gone “viral” on Tik Tok, I’ve gathered over 100,000 followers and subscribers, and I’ve been featured almost monthly on every website for authors, as well as other media outlets, blogs, and podcasts.”
What Christina credits her uphill business success with is the strength to face, accept, and love herself. “Dig deep and find that part of you, no matter how deeply buried, that knows your worth and knows exactly what you are capable of, push past the insecurity and fear, and put yourself out there for the world to see, warts and all. […] The first time I recorded a live event and somehow stumbled into the topic of my recent divorce and subsequent trauma, the replay and repost of that video not only received hundreds of thousands of views and likes … I went “viral,” something that would never have happened to the insecure, unconfident woman I once was.”
“Had the two of us ever met, we’d have had hardly a thing in common. Yet I have always cited Ruth Bader Ginsburg as my role model for one simple reason. [She] is one of the most famous women in history who achieved the highest level of success possible in her chosen career path by being steadfast in her personal opinions and speaking out against opinions she firmly disagreed with. [I admire how] she voiced her opinions and her dissent quietly but powerfully and with class.”
One of Christina Kaye’s favorite quotes is by Ruth Bader Ginsburg, “Fight for the things you care about but do it in a way that will lead others to join you.” That’s exactly what these femalepreneurs did to succeed. No matter the view people had of them, personal insecurities, lack of funding, or the circumstances life threw their way, they held their flag high. They won and they keep winning because, in business, fighting and winning is a daily endeavor.
What all of us, regardless of gender, can do to empower more women in business is to provide a safe space around their physical, mental, and professional wellbeing that we celebrate this month. Thank you to everyone who helps bring this reality closer, and to all femalepreneurs out there — Happy National Women’s Entrepreneurship Month!
P.S. If you’re not one of us yet, what’s stopping you? Here’s your go-to 8-Step Guide to Entrepreneurship