8 Women Entrepreneurs Share How They Conquered Their Biggest Roadblocks

They’re successful now, but it hasn’t always looked so easy.

8 Women Entrepreneurs Share How They Conquered Their Biggest Roadblocks
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Whether it’s breaking the glass ceiling or battling stereotypes, no one’s denying women have come a long way. But we still have a long way to go.


From pitching to investors who are used to defining “entrepreneurs” as young, white, and male to tuning out the self-doubt that tears your confidence apart, below eight successful women entrepreneurs share how they take down the roadblocks in their way.


Cher Wang, co-founder and chairperson of HTC Corporation

“You have to keep moving–and you need to be ready and willing to change course in order to realize your vision.”

Wang says that, whatever happens, the one thing that never changes is her willingness to be on the edge and stay true to herself. “I prefer to inspire my people and, in turn, be inspired by them in order to create what I hope will be incredible outcomes that will change society for the better. That’s not just what HTC’s all about. It’s what I personally believe and what my team needs to believe as we continue to push.”


Alexandra Ostrow, founder of WhyWhisper


“I personally find self-doubt to be one of the greatest obstacles I’ve encountered, both as a woman and a business owner. Overcoming this is a daily exercise, and accomplished only through perseverance in the face of fear. When I first went out on my own, many people expressed concerns at the uncertainty that was likely to await me . . . there was no malintent, just a general, ‘Are you sure this is going to work?’ accompanied by worried discussions of finances, benefits, and business acumen. It was difficult to tune out the noise, but I wouldn’t be where I am today if I hadn’t learned to listen to myself in such circumstances. The way I see it, each of us has one life to live, and it’s up to me to make the most of mine.”


Jody Porowski, founder of Avelist

Porowski tells Fast Company that one of the biggest roadblocks she ever faced while leading Avelist was running out of funding. From early on, she was determined that running out of cash would not be the end of her company and when her worst fear became a reality, Porowski quickly turned to Plan B, or her “Avelist emergency fund”: selling her home with no regret.

“Based on my observation of other entrepreneurs and my own personal experience, I’ve found that success comes from a refusal to give up. Every entrepreneur faces roadblocks, but the ones who succeed are the ones who don’t give up at roadblock number 1 and who still refuse to give up at road block number 101. In particular there’s a specific kind of determination that I call ‘strategic determination’ which is exemplified by most of the entrepreneurs that I admire. They know that sometimes despite their best efforts they will fail, so they always have a backup plan. They’re flexible, adaptable, quick and strategic. If plan A doesn’t work, they’ve got plan B lined up, and then they have Plan C and Plan D.”


Meredith C. Fineman, founder of Finepoint


“What I will do in a down period, instead of worrying, is stop pushing. I think it’s better to be 100% into what you’re pitching, collaborating on, or working on, than trying to slog through and doing things as a result of worry or negativity. This is obviously easier said than done. However, for instance, if I’m going through a period of business development and it’s not sticking, I will switch focus to working on my writing or Finepoint’s materials or hires or output. If you’re operating out of fear, you’re usually knee-jerking.”


Melissa Jun Rowley, creator of docu-series Magic Makers

“The most important thing to remember is that most obstacles aren’t real. A lot of roadblocks in business and in life are simply delays or illusions we create in our minds because there’s a voice inside of us that feeds self-doubt and fear. I used to let that voice dictate how I pursued my goal–meaning I stalled half the time. I finally learned that the hurdle in front of me was me, and that the delay in progress was an opportunity to think and do things differently.”


Cindy Gallop, founder of Make Love Not Porn

“One of my favorite sayings is, ‘those people who say it can’t be done, should get out of the way of those people doing it.’ Show me and my co-founders Oonie Chase and Corey Innis an obstacle, and we will find a way over, under, through, or around it.”


Gallop says that the many obstacles that have stood to break down her company simply hasn’t because she believes so strongly in MLNP’s mission to change the way society views sex.

“Video streaming services won’t host us. We built our own video-streaming platform from scratch. Paypal won’t work with us. We researched the entire fintech landscape and found Dwolla. Mainstream credit-card processors won’t work with us, adult-industry payment processors charge extortionate rates that don’t support our revenue-sharing business model. We registered MLNP in Europe to work with a European payment partner and a bank who enable us to take credit cards. VCs won’t fund us. We spent two years pitching to find a seed angel investor.”


Cassandra Phillipps, founder of the international event FailCon

In the most frantic roadblocks, Phillipps says to take a step back, breathe, and reach out to your networks.

“I have found that just meeting someone for breakfast who is knowledgeable in the industry and open to brainstorm and listen to problems can be a life saver.”


When planning for a FailCon conference last summer, Phillipps was struggling to get the speakers she wanted and, for that reason, the event wasn’t selling as well as expected. Instead of letting herself get tense, as she is prone to do when things go wrong, Phillipps reached out to two advisors who had been with her since the company’s early days.

“We scheduled a few weekly coffee meetings to just go through lists of ideas, plan fall-back ideas, and marketing plans. It felt great to get fresh insight on the problems and to have something on the calendar to help structure the problem in a manageable way.”


Vivian Rosenthal, founder & CEO, Snaps

“You must trust and hone your intuition so that you are able to make any decision in nine seconds or less. I actually learned this through studying the teachings of Yogi Bhajan, who brought Kundalini Yoga to the West. After learning to work with my intuition and to trust it, I realized that most decisions can and should be made almost instantaneously . . . what is necessary is conviction and intuition to make smart decisions quickly. We make hundreds, if not thousands, of decisions a day, and we need to learn how to trust and use our intuition.”


About the author

Vivian Giang is a business writer of gender conversations, leadership, entrepreneurship, workplace psychology, and whatever else she finds interesting related to work and play. You can find her on Twitter at @vivian_giang.