Challenges Faced by Women Entrepreneurs and Some of the Most Successful Women to Follow

Paula Fernandes and Marisa Sanfilippo, Contributing Writers

Women must contend with a wide range of challenges in business. Here are some of the challenges women encounter – and some of the larger-than-life female entrepreneurs who overcame them.

On paper, things have never looked better for female entrepreneurs. As of 2017, more than 11 million U.S. businesses were owned by women, employing nearly 9 million people and generating $1.7 trillion in sales, according to the National Association of Women Business Owners.  

But these numbers only tell part of the story. Women-owned businesses are still in the minority, and the hurdles faced by women who have embraced entrepreneurship are vast and often very different from those experienced by their male counterparts. To shed light on some of these disparities, Business News Daily asked female CEOs about the key challenges women entrepreneurs face and how to overcome them.  

7 challenges women entrepreneurs face and how to overcome them 

1. Defying social expectations

Most female business owners who have attended networking events can relate to this scenario: You walk into a crowded seminar and can count the number of women there on one hand. When women entrepreneurs talk business with primarily male executives, it can be unnerving.  

In this sort of situation, women may feel as though they need to adopt a stereotypically “male” attitude toward business: competitive, aggressive, and sometimes harsh. But successful female CEOs believe that remaining true to themselves and finding your own voice are the keys to rising above preconceived expectations. 

“Be yourself, and have confidence in who you are,” said Hilary Genga, founder, and CEO of Trunkettes. “You made it to where you are through hard work and perseverance, but most importantly, you’re there. Don’t conform yourself to a man’s idea of what a leader should look like.”  

2. Accessing funding

Not all startup founders look for investors to help get their businesses off the ground, but those who do know how difficult the pitching process can be. Raising capital is even more difficult for women-owned businesses. A 2014 Babson College report found that less than 3% of companies with venture capital funding had female CEOs.  

Bonnie Crater, president and CEO of Full Circle Insights, said venture capitalists tend to invest in startups run by people of their own “tribe.” For example, a Stanford-educated investor will want to back a Stanford alum’s business. This means that VC firms with female partners are more likely to invest in women-run startups. According to the Babson report, however, that accounts for only 6% of U.S. firms. Crater recommends that women looking for business investors should build confidence through a great team and business plan.  

Investors typically look for businesses that can grow their valuation to more than $1 billion, Crater said. “Think about how to do that. If you have experts on your founding team that can execute the business [operations] well, investors will have confidence in those people. [You also] need a good product-market fit.”  

Another way to overcome this issue is to get more female investors to support one another, said Felena Hanson, founder of the Hera Hub coworking space for female entrepreneurs. According to Hanson, groups like hers are “looking to not only inspire and encourage female investors but to grow and support other female entrepreneurs through both funding and strategic educational workshops.”  

Female entrepreneurs can raise the necessary capital for their business by learning to ask for exactly what they need, even if that means requesting more than what they want.    

“Women are more conservative and don’t overstate projections,” said Gloria Kolb, CEO, and co-founder of Elidah and a mentor in the University of Connecticut’s Technology Incubation Program. “When we pitch investors, we are often pitching realistic numbers. But men so often overstate and exaggerate that investors often discount the numbers off the bat.”  

Kolb said that investors, who are usually men, tend to assume that women entrepreneurs are operating just like men and inflating their numbers. Therefore, they will provide funding at lower levels than requested. Women need to understand this dynamic and approach their pitches accordingly. 

3. Struggling to be taken seriously 

At one time or another, most women CEOs find themselves in a male-dominated industry or workplace that does not want to acknowledge their leadership role. Alison Gutterman, CEO, and president of Jelmar, had this experience early in her career. 

“As a female entrepreneur in a male-dominated industry, earning respect has been a struggle,” she said. Because Jelmar is her family’s business, she faced presumptions that she was living off her father’s and grandfather’s reputations. 

“I was more than willing to put in the work to create my own reputation for being a hardworking, honorable businessperson in my own right,” Gutterman said. “To overcome this, I have had to learn to build my confidence and overcome my negative self-talk.”  

Those negative comments that have built up in your head are stopping you from reaching your full potential, said Gutterman. To combat them, she has joined a variety of women entrepreneur groups.  

“These groups have provided me mentors and peers to inspire me, hit me with reality checks on my capabilities and successes, and help me grow and learn from their outside perspectives and experiences,” she said.  

4. Owning your accomplishments 

The communal, consensus-building qualities encouraged in young girls can leave women unintentionally downplaying their own worth. Molly MacDonald, founder, and CEO of The Mobile Locker Co., a startup that provides personal storage for events, said she has always found it difficult to convey her own value as a leader.   

“When I talk about the company … I always find myself saying ‘we’ instead of ‘I,’” MacDonald said. “Using the first person to discuss successes feels to me as if I’m bragging, and I cannot shake the idea that if someone knows it’s just me in control, the value of what we do will go down. As I grow the business, I am making an effort to own what I’ve accomplished.” 

Similarly, Shilonda Downing, founder of Virtual Work Team, advises women to recognize the value of their creative ideas.  

“I’ve had to catch myself on occasion when I noticed that I’m giving away too much without a financial commitment from a potential client,” Downing said. “[I] recommend other women value their knowledge as well.”  

Sharon Rowlands, CEO of Web.com Group and ReachLocal, agreed that confidence is the key to success, even when you’re up against a boardroom full of men.  

“I had confidence in my abilities to run the business,” said Rowlands. “I just made sure that any initiative I was trying to move forward was backed up by a solid business case. I was never unprepared for the questions I knew would come.”  

5. Building a support network 

A robust support network is essential for entrepreneurial success, so it’s no surprise that 48% of female founders report that a lack of available advisors and mentors limits their professional growth, according to Inc.  

“With the majority of the high-level business world still being dominated by men, it can be hard to blaze your own path and facilitate the introductions and connections into some of the more elite business networks,” said Hanson. “As most of the business, today still rings true with the philosophy that ‘it’s not what you know; it’s who you know,’ this can be a huge factor in your ultimate success.”  

Finding the right support network isn’t always easy. Some good places to start are women-focused networking events – such as WIN Conference, eWomenNetwork, and Bizwomen events – as well as online forums and groups created specifically for women in business, like Ellevate Network. 

Once you find your network of supporters, don’t be afraid to ask for what you really need from them.  

“Ask often and … be clear about what you need,” said Addie Swartz, CEO of reacHIRE, which connects companies to women who are returning to work after a break or looking for new roles and advancement. “You never know who has the capacity to help. People are more likely to jump in if you are specific about what you need them to do. If you don’t ask, you won’t get.”   

6. Balancing business and family life 

Parent entrepreneurs have dual responsibilities to their businesses and to their families; finding ways to devote time to both is key to achieving that elusive work-life balance, said Genga. 

For Michelle Garrett of Garrett Public Relations, finding this balance meant leaving a corporate job and starting her own consulting business before her first child was born.  

“I knew that if I had continued working in the corporate world … I would have had to make a lot of choices I didn’t want to make,” said Garrett. “I do think the culture of work is shifting to allow women more flexibility, which is a good thing. But working for yourself will probably always allow more freedom than working for someone else.”   

7. Coping with fear of failure 

Failure is a very real possibility in any business venture, but Kristi Piehl, founder, and CEO of Media Minefield, advises women not to let their insecurities keep them from dreaming big. She encourages women to work through the moments of self-doubt that every business owner faces and not wait for perfection before starting their business or taking a big promotion. 

Failure should not be viewed as a negative or an excuse for relinquishing your goals, according to Swartz.  

“When you hear ‘no’ again and again when your plans don’t turn out, or if you make a costly decision … see that as a teaching moment,” she added.  

The road to success is paved with losses, mishaps, and mistakes, but it can still take you where you want to go as long as you don’t lose sight of your ultimate destination. 

“Stay the course,” Swartz said. “Take in all the feedback; filter out the noise and the naysayers; learn from your mistakes and try not to make them again. But whatever you do, do not give up.”  

5 of the most successful women entrepreneurs

Based on their accomplishments and net worth, the following ladies made our cut for some of the most successful women entrepreneurs to date. Love them or hate them, they sure made names for themselves in strong careers.   

1. Oprah 

No last name is needed for Oprah, known as “the first lady of talk shows.” As noted in her online biography, she was born on an isolated farm in Mississippi, where she entertained herself by playacting in front of farm animals. She came from a poor family and experienced sexual abuse at the age of 9, but she says she hit a turning point in her teenage years when her father saved her life.   

Oprah Winfrey’s first streak of success came when she won the titles of Miss Black Nashville and Miss Tennessee in her freshman year of college. After graduating, she moved into the TV industry and was soon getting better ratings than daytime talk show pioneer Phil Donahue. Today, Oprah is best known for hosting The Oprah Winfrey Show, being a billionaire philanthropist, and having her own TV network and magazine.   

2. Gisele Bundchen 

In her instant New York Times bestseller Lessons, Gisele Bundchen talked about her time growing up in Brazil with her sisters and how she was teased for being tall and skinny. Those features helped launch her modeling career, and since 2001, she has been one of the highest-paid models in the world.    

Aside from the well-known work she has done in the modeling industry, Bundchen is the founder of Sejaa Pure Skincare. The line includes a face cream, night cream and mud mask. She plays to her personal brand with an entrepreneurial mindset, earning a cut of sales from jelly sandals she designed and her own line of lingerie, according to StyleCaster.   

3. Sheryl Sandberg 

This American technology executive was born in Washington, D.C., but moved to North Miami Beach, Florida, with her family soon after. Her success came at a young age when she was part of the National Honor Society and graduated high school in the ninth position of her senior class with a 4.6 GPA. Her accomplishments in high school did not go unnoticed when she was admitted to Harvard University.   

Sandberg is best known for her work with Google and Facebook and for her New York Times bestseller, Lean In. After holding several prestigious positions with other companies, Sandberg served as Google’s vice president of global online sales and operations until she was recruited to be Facebook’s first COO.   

4. Lady Gaga  

Born by the name Stefani Joanne Angelina Germanotta, Lady Gaga first took the world by storm in 2008 with her pop hit “Just Dance.” But before she was Gaga, she was a girl in a Catholic school who had a love for music and wrote her first piano ballad when she was 13.  

In 2008, Gaga released her debut album, The Fame, and started making a name for herself. Lady Gaga never was just your average pop star – she goes all out in everything she does, from her risky outfits to her fun dance moves and jaw-dropping theatrical performances. 

Music was only the start for Gaga. Today her credits include a Golden Globe for acting in American Horror Story, an Oscar win for Best Original Song and a nomination for Best Actress in A Star Is Born, and a makeup line called Haus Labs that the internet is literally going “Gaga” over.  

5. J.K. Rowling 

From a struggling mom to one of the world’s biggest names, J.K. Rowling is a must-watch on our top women entrepreneurs list. She was born and raised in England but later moved to Portugal to teach. While on welfare and struggling to support her daughter after a divorce, she started writing the first Harry Potter book.   

Her first book sold for a whopping $4,000 and hit shelves in 1997, kicking off what would soon become a phenomenon. Rowling’s creative and intelligent writing had people everywhere with their faces stuck in her books. In one year alone, the billionaire made $54 million from Harry Potter sales across the world.