9 Female Entrepreneurs on the Biggest Obstacle They Faced

by Meredith Wood 

For many women who start their own business, their venture is everything—according to SCORE, 62% of female entrepreneurs say their business is their primary income. This isn’t a hobby and it’s crucial that they succeed.

From navigating the nature of meetings to the struggle to be taken seriously, female entrepreneurs face obstacles that are sometimes beyond the typical roadblocks to success for business owners.

A major part of overcoming obstacles is knowing what to expect. Here are stories from nine women on the biggest obstacle they faced when starting out.

Note: These responses have been edited for length and clarity.


A lack of network within the entrepreneurial community

“When I got the idea for the business in 2016, I had established a fantastic network as a personal assistant as well as in advertising, but I needed mentorship and support in how to grow a tech and service startup.”
—Valerie Donohue, founder of ChatterBoss


Setting boundaries for professional meetings

“I view every meeting I have as professional but I have experienced the opposite when interacting with male clients, investors, or potential partners… I learned how important it is to set boundaries. After a while, people will learn what they are and only come with serious offers.”
—Ladan Davia, founder and CEO of Beeya


The opinions of friends and family

“Society tells everyone they have to go to school, get a 9-5, work until retirement age, then collect Social Security. If you try to break the mold, people will tell you it is dangerous, risky, not possible, or something that should not even be tried.”
—Stacy Caprio, an online marketer, designer and growth expert


Being taken seriously

“I live in a conservative area, and I often felt that other business leaders (typically men) thought it was ‘cute’ that a woman was ‘playing at business.’ I’m stubborn and don’t accept discrimination, for myself or for my employees, so I managed these experiences by excluding them from my business practices and hustling every day to show that I was a serious businesswoman. Several years later, when I hired my female developer as I scaled and received comments from male clients regarding her good looks, I immediately fired them. I am protective of my own boundaries, but am even more so for the employees I spend time and money to train and who trust me to support their careers.”
—Veronica Kirin, author, speaker, and coach to LGBTQ entrepreneurs


My confidence

“I was so sure I had something great, but the way I talked about it delegitimized my business. I made it sound like this little side project instead of this thing that I work on day and night and have grown out of nothing. Women are taught to couch their successes and to not act confident. And even though in my head I knew what I had was great, I had the hardest time talking about it and really selling it. I had to change my language, and as soon as I did that everything changed.”
—Julia Nusbaum, creator and curator of HerStry


A lack of funding opportunities

“98% of funding goes to male founders, yet incubators and angels continue to court women with the promise of investment but who have a statistically zero chance of getting it. And we play along because we don’t know… Because no one pays attention to the fact that even female founder funds give women-owned companies proportionally less money.”
—Paula Muto, CEO and founder of UBERDOC


Not knowing when to take the leap

“My co-founder and I were self funding the beginning of the company and we always struggled with the ‘dance’ between when you need to quit your full time job in ordering to allocate the right amount of time to help your business succeed, while also balancing the fact that we both needed an income to order to live. Because of this struggle, we never fully made the job into quitting our full time jobs and I were speculate that played a part in our lack of success.”
—Hannah Stoppelmann, co-founder of Suit and Sweet.


Juggling children and entrepreneurship

“I think a huge obstacle (and blessing) for me was learning how to juggle having one child, and then two, while still getting everything done. Waking up earlier and nap times were my times to hustle. I think time management is huge. I learned that most of my work I get done after I drop them off at school in the mornings. That first hour or two is golden.”
—Karina Michel, owner and producer, Tallulah Films


Defining my ideal client

“When I began coaching, I took anyone who would pay me because I felt desperate for the business. But I quickly realized that some clients energize me more than others. I made a decision after the first year to be more selective in choosing who to work with. I now turn down business because I know I am not a good fit… My business doubled once I got clear exactly who I was marketing my services to.”
—Claire Pearson, life coach


Some obstacles are external, some are internal; some are specific to women in business. If you’ve faced anything like the problems above, know that you’re not alone. Overcoming barriers is part of the entrepreneurial journey, especially for women.



Meredith Wood is the Editor-in-Chief at Fundera, an online marketplace for small business financial solutions. Specializing in financial advice for small business owners, Meredith is a current and past contributor to Yahoo!, Amex OPEN Forum, Fox Business, SCORE, AllBusiness and more.

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2 Replies to “9 Female Entrepreneurs on the Biggest Obstacle They Faced”

  1. Dragan

    Great and inspiring women! It must be hard juggling kids, the house, the expectations. Seeing women in business doing such an amazing job really brings a smile to my face.

  2. Michael LaRocca

    Mom quit her job in the early 1980s to found her own business, and I still apply what I learned from her in my own business every day.

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