November 19, 2019 15 min read

Entrepreneur is celebrating Women’s Entrepreneurship Day by examining some of the notable women entrepreneurs it profiled this year. As the saying goes, experience is the best teacher. Whether it’s coping with divorce, depression or death, these amazing women have valuable lessons to share.

Find your passion

Baking is in Laurie Gray’s blood. As a child, Gray was right at her mother’s side as she baked cookies, brownies and pies from scratch. In Gray’s make-believe kitchen, she would make her own creations in her Little Chef toy oven.

In 2003, Gray left a career in banking and began baking and selling pies. She learned firsthand how difficult it was to run a business.  After two years, the single mother of two kids with no health insurance or retirement savings sold her stake in the business and returned to the corporate world.

More than a decade later, Gray lost her job and was forced to rethink her future. One day, Gray’s mother found her daughter’s toy oven in the attic. The discovery inspired Gray to become a business owner again. In June 2016, she opened The Pie Bar, a pie shop in Long Beach, Calif. On display in the front of the store: the Little Chef toy oven Gray had as a child. 

“When kids come in with their parents, I get to share my story about playing with it and how it created a passion that led to owning my pie shop,” she said. “It reminds me of how far I’ve come. If you quit, and that’s it, then you’ll never know what you can accomplish.”

Read more about Laurie Gray: How a Childhood Toy Inspired This Entrepreneur to Launch Her Business

Persistence is the key to getting results

As a black woman, Melissa Butler couldn’t find a lipstick that complimented her skin tone. She also questioned why most cosmetics were made with unnecessary chemicals. That’s when she decided to create The Lip Bar: her own line of vegan, cruelty-free lipsticks. 

Butler was as bold as her purple and green lip colors. During the day, she worked her Wall Street job, and at night, she experimented with lipstick formulas in her kitchen. She stalked cosmetic chemists on LinkedIn and asked them specific questions. When Butler couldn’t afford the $1,500 fee to attend trade shows, she would get the vendor list and call them one by one. Through detective work using LinkedIn and Google, Butler eventually found Target’s buyer and signed a deal to sell her products at the retailer.

“I always tell people I’m not passionate about makeup,” she said, according to The Lip Bar’s website. “I’m a minimalist girl who believes a pop of color on the lips will give you enough confidence to take on the day and kick its ass! However, I am passionate about creating an inclusive narrative on what beauty is and reminding women that we don’t have to settle for anything.”

Read more about Melissa Butler: She Was Rejected On Shark Tank. Then She Used That To Her Advantage

Tap into your area of expertise

In 2009, music producer Kelly Bayett was at a crossroads. She was the mother of two kids, in the midst of a divorce and overdue for a raise at her job. When Bayett asked her employer for a bump in salary, she was told no, citing the recession. That prompted Bayett to leave her job and start the music and sound company, Barking Owl.

Bayett operated the business out of her house. She didn’t have a reel to show prospective clients and had to hustle to get work. Bayett’s varied industry experience ranging from voice-over acting to scoring feature films served her well. About a year in, Barking Owl scored a huge win and did the sound design for a Coca-Cola Super Bowl spot. Then followed big clients like Microsoft, Adidas, Nike and Toyota.

“If you try to compete by not being authentic to yourself, then I feel like success is fleeting,” said Bayett. “You always have to be true to yourself. You have to keep your side of the street clean always. I just do everything straightforward and with my full heart. I will say that that approach has brought forth the greatest clients and talents and people.”

Read more about Kelly Bayett: At the Height of the Recession, This Entrepreneur Struck Out on Her Own. 10 Years Later? She’s Still Going Strong, With Clients Like Google and Coca-Cola

The importance of work/life balance

In the spring of 2009, Jung Lee was working on one of the biggest productions of her career. The founder of the events production and design company Fête was in charge of a bar mitzvah for a prominent family in New York. From building temporary housing to making sure all of the meals were kosher, she took charge of every decision.

At the same time, her sister-in-law was fighting cancer and becoming increasingly ill. Lee wanted to see her but felt compelled to stay on the job site. When the event was over, Lee rushed to the hospital. Days later, her sister-in-law passed away.

Lee said she regrets not spending more time with her sister-in-law before she died. She was guilty of putting 100 percent into her clients and managing everything herself. Lee realized she needed to build a strong team so it would be possible for her to step away.

”If I’m working too much, I try to sit back,” she said. “I’ve learned that taking the time to develop talent will always serve a business. It’s putting money in the bank for the future and giving you space to focus on what really matters.”

Read more about Jung Lee: After A Family Tragedy, I Finally Learned How To Balance My Work Life

Identify a business need

Shamanth Pereira didn’t feel confident about her body after giving birth to her first son. She was so focused on taking care of him that she didn’t look after herself. When pregnant with her second child, she vowed to recover more quickly. Pereira then realized that most of the mothers she knew struggled with the same problem. 

Pereira’s solution was Invisibelly, a line of high-waisted compression leggings with built-in shapewear. Invisibelly merges the Asian tradition of belly wrapping (which Pereria learned from her mother) with the compression technology in athletic wear.

For Pereria, it’s not just about utility. It’s also about sustainability. All of the materials, technologies and methods used in Invisibelly’s manufacturing process aim to reduce any impact on the environment.

“What began as a ritual handed down by generations to heal the body postpartum soon evolved into a lifestyle brand to help women feel more confident [and] fall in love with their bodies while doing good for the environment,” said Pereira, according to Invisibelly’s website.

Read more about Shamanth Pereira: This Founder Ditched Investment Banking to Help New Moms — and All Women — Feel Confident

Think outside the box

Alexandra Waldman kept wondering: Since a majority of American women are a size 14 or larger, why are there so few apparel options? Waldman answered her own question in 2015 when she founded the clothing company Universal Standard with Polina Veksler. The company began by offering sizes 10 to 28 and has since expanded its range to sizes from 00 to 40.

Waldman said her biggest challenge will be to convince the industry and the consumer that this is how fashion should be. She said her ultimate goal is to make apparel that is accessible to everyone.

“I firmly believe that we don’t need to have another ‘plus-size’ brand,” said Waldman. “What we need is for brands to make all sizes. And it’s not just about size; it’s about style and variety. I think that larger women have simply not been allowed to look as wonderful as smaller women, and then they were judged for it. It’s time to change all that.”

Read more about Alexandra Waldman: How to Not Let ‘the Practical’ Drown out Your Dream

Know when to ask for help

When Kachan Singh opened Crumbs & Whiskers in Washington, D.C., she wasn’t prepared for the growth rate of her cat cafe. Singh’s ambition took over and within two years, she opened a second location in Los Angeles.

The more the businesses succeeded, the more Singh grew depressed. She felt worthless. Her employees were also unhappy. One fateful week, all of the company’s management quit, as well as many employees. Not only had Singh grown her company too fast, but she also didn’t take care of herself or her staff.

Singh admitted that she needed help and turned to her mentor. 

“As my coach, she was a lifesaver once more: She helped me turn my business around, develop my leadership skills and change my beliefs about what success means,” she said. “At our cafe, a fluorescent sign flickers on one of the walls: a four-letter word, with two letters on top and two on the bottom. The top row says “me” and the bottom row says “ow” — standing in, of course, for “meow”  — but the combination sometimes reminds me not of the sounds our adorable felines make but of the pain I went through on my journey of entrepreneurship and healing.”

Read more about Kachan Singh: From ‘Ow’ to ‘Meow’: A Young Catpreneur Discovers Her Own Meaning of Success

Don’t be afraid of failure

Lauren Cascio’s husband physically abused her for three of their four years of marriage. When the abuse spilled over to her children, she decided that enough was enough. The date was April 29, 2014: her birthday.

After divorcing her husband, Cascio felt reborn. Knowing when to quit or change directions is a practice she feels that she’s also applied to her company, Abartys Health. The health insurance technology company offers a system that allows for seamless data flow and communication between insurers doctors and patients.

“I had to quickly recognize that some processes were not working, and I needed to step back and make an unbiased decision based on the wellness of the company — whether it was a bad client, an employee who I was attached to or a vendor,” said Cascio. “I essentially became married to my investors, employees, clients and so on.”

Read more about Lauren Cascio: How the Rock Bottom of My Abusive Marriage Became the Foundation of My Booming Startup

Be creative

When Jen Hansard’s husband was laid off in 2011, her family was without health insurance. She began experimenting with green smoothies as a way to boost her children’s immune systems and avoid trips to the doctor. That’s how Simple Green Smoothies was born.

With very few resources, Hansard had to get creative. She became a walking billboard for her green smoothie and carried it around at all times. To gain a following, Hansard gave out recipes and tips to anyone who would read or listen.

“While being scrappy may seem exhausting and overwhelming, trust me: The payoff for your hard work will make the challenging path you’ve chosen worth it,” she said.

Read more about Jen Hansard: From Unemployment to CEO: 4 Things This Mom Did to Turn Her Passion Into a Thriving Business

Build a strong team and culture

The public relations firm Tribe Builder Media boasts an over-97-percent success rate in getting clients featured in top-tier publications. Founder and CEO Danielle Sabrina credits a strong team and culture for her company’s success.

Sabrina knows that working 9-to-5 isn’t the only way to make a living. She lets her team tell her what times work for them to start and end their day. Sabrina then figures out how to integrate their schedules into the company. She says the traditional 9-to-5 workday is a breeding ground for complacency and offers little incentive for people to go above and beyond.

“I promote, perhaps even demand, a culture of positive and uplifting energy, because we never know what other people are going through,” she said. “So kindness first, always. I’m also big on efficiency. We’re always looking for ways to work smarter so we can truly put our focus into the creative side of things while at the same time allowing us to manage our lives better.”

Read more about Danielle Sabrina: The Secrets to Building a Strong Culture That Catapults You to Success

Take chances

When Bobbi Brown first began making lipsticks, someone told her that the world didn’t need another cosmetics company. Brown ignored the advice. The rest, as they say, is history.

From its beginnings in 1991, Bobbi Brown Cosmetics has grown into a billion-dollar makeup company selling everything from foundation to face cream. It’s now under the helm of Estée Lauder. After 25 years with Bobbi Brown Cosmetics, the makeup-artist-turned-entrepreneur left the company in 2016 with no plans on what to do next.

Three years later, Brown has expanded into areas you might not imagine. She has a supplement line with Walmart, an editorial website, a film and photo studio, a boutique hotel and a new podcast. Through it all, Brown remains fearless.

“Honestly, after all these years, people want to know from me: How do you become confident?” she said. “The only thing confidence is: being comfortable in your skin … I’m comfortable to make mistakes. I’m comfortable to admit what I don’t know. I just think it’s interesting not knowing things, so long as you’re not afraid to ask questions and say, ‘Wait; what do you mean?'” 

Read more about Bobbi Brown: Bobbi Brown’s Guide to Success: Go To Fewer Meetings and Take More Action

Prepare to fight for funding

Melissa Hanna had a hard time raising funding for her startup, Mahmee. Not only is she a woman of color in her twenties, but the predominately white, male venture capitalists often didn’t understand the vision or value of the company she co-founded with her mother Linda.

Mahmee is a maternal healthcare startup that connects mothers and babies to the prenatal and postpartum care they need. Investors saw a charity project. Hanna saw a multibillion-dollar market.

Her perseverance paid off. In July, Mahmee received a $3 million investment from a group including Mark Cuban and Serena Williams.

“I know that fundraising for any startup is an arduous process and can be a really lonely experience for the founders sharing their vision and finding the right investors along the way,” said Hanna. “There was something special about how difficult it was to raise money for Mahmee, that happened at the intersection of our diverse founding team, our billion-dollar vision [and] our mission to have a social impact in a space where, for the longest time, people [didn’t] even know there was an actual crisis happening.”

Read more about Melissa Hanna: This Female Founder Fought to Stay in the Game And She Just Raised $3 Million in Funding from Serena Williams, Mark Cuban and Arlan Hamilton

Trust your gut

It took a recipe of passion and persistence for Sarah Jones to make Miss Jones Baking Co. a reality.

When Jones came up for the idea for an organic baking line, she knew it would reach an untapped market: people who are busy but love to bake and want healthy food. 

But her road to entrepreneurship wasn’t easy. She began working on the idea for Miss Jones Baking Co. in 2011 but didn’t leave her job to pursue it full-time until 2016. Jones spent four years trying to convince a manufacturer to help her produce frosting with natural and organic ingredient standards.

Fast-forward to 2019, and her products are now sold at Amazon, plus nationwide retailers such as Target, Whole Foods and Fairway.

“Once you get through something hard, you realize you can get through something hard again,” she said. “The repetition and the practice of overcoming failure and overcoming challenges build up your persistence and your resilience and allow you to keep going forward.”

Read more about Sarah Jones: The ‘Millennial Betty Crocker’ Founder of a Baking Empire Shares Her Recipe for Staying Resilient