Lessons on Challenge from 10 Female Entrepreneurs

Last Update: March 8, 2022

As a demographic, women bore the brunt of the COVID-19 pandemic’s effects on employment. According to an analysis of labor statistics by the National Women’s Law Center, women lost over 5 million jobs since the pandemic began, 1 million more jobs than men lost. Around 2.5 million women have left the workforce since February 2020, as reported by the Bureau of Labor Statistics (compared to 1.8 million men), in many cases because they were forced to make the difficult choice between family and career when schools and childcare facilities closed. A confluence of factors that existed long before COVID-19 hit—lack of investment in childcare resources, society’s failure to value labor traditionally done by women, insufficient workplace policies to accommodate true work-life balance—left women in a vulnerable position that the pandemic exacerbated.

While the last year was a profoundly difficult one, what tests us also has the power to shape us, and we spoke to a remarkable group of female entrepreneurs who are proof. In keeping with the theme of this year’s International Women’s Day, Choose to Challenge, we talked to founders and CEOs of a few woman-owned brands featured at Thrive Market about the challenges they’ve overcome, the strength they’ve forged through struggle, and the ways they’re pushing boundaries in their industries.

What was one of the biggest challenges you’ve faced in your journey as an entrepreneur, and how did you overcome it?

“As a BIPOC woman I felt it was challenging for me to get people to take me seriously. I had co-packers quote me ridiculous pricing and unreasonable terms. It took me a while to get big distributors to notice me; most of my peers who looked different were able to get the attention a lot sooner. I was always expected to prove myself a lot more than some of my peers because I didn’t fall in the usual natural food supplier demographics. Also, as an immigrant, I had no connections in the country or the industry that I could have used to my advantage. The only way to overcome it was to show them the results.” —Richa Gupta, Good Food For Good

“Finding co-founders who have the same uncompromising values and commitment to building a truly purpose-driven brand—and never sacrificing sustainability, quality, efficacy and transparency. I’ve realized that the most important quality to have as an entrepreneur is resilience, so I’ve overcome this challenge by maintaining a strong shield of resilience through many years of ideation, tests, fumbles and pivots.” —Jessica Assaf, Prima

Overcoming imposter syndrome! As a founder, you have to be optimistic, positive, and future-thinking, even when you’re clouded by doubt. That, and asking for help. It’s something I’m continuously rewarded for doing, so I’m getting better about that one.” —Kaitlin Mogentale, Pulp Pantry

“I hustled so hard to get traction at the start. Once I was able to get products into customers’ hands, everything started working. Our customers quickly saw that our products worked for them, and we gained a really engaged consumer base. The biggest challenge from there was having to turn away customers and purchase orders because we didn’t have the supply chain to fulfill them. I really had to figure out how to scale the business and get the right quantity of product to market. I didn’t have the money to front a product run with the manufacturer, so I had to get really scrappy and find a manufacturer that would work with me on a payment plan. Ultimately I was able to make it happen, but it wasn’t easy.” —Carly Stein, Beekeeper’s Naturals

“I have always had a pretty intense fear of public speaking going back as far as grade school. We launched Winged in March of 2019 at [natural products show] Expo West. I was asked to speak on a marketing panel in front of about 1,100 people. This was without a doubt my biggest fear coming to fruition. I had no choice but to accept, as it was incredible exposure for our new brand. The result was retail placement at some of the top retailers in the country. The big takeaway for me was that when something scares you, that is your sign to run towards it. Every time you face a fear head on, you level up in a fundamental way.—Jessica Mulligan, Winged

“Last year was probably the most challenging year in my career due to the pandemic and all the uncertainty it caused. It was one thing to have to get used to running a startup company remotely, but the biggest challenge came from managing our supply chain to meet fluctuating demands for our feminine care products. Prior to March 2020, we were running our own warehouse, fulfilling all the orders ourselves. Due to the stockpiling of feminine care products back in March last year, there was a huge amount of pressure on our warehouse team to process all the orders in an extremely short period of time while making sure we were taking precautions for Covid-19. It was a constant struggle to balance managing my team’s health and safety and ensuring the best customer service when people really needed it.” —Yanghee Paik, Rael

“Manufacturing has been an ongoing challenge. It’s traditionally been a male-centric world with an old school mentality, which presents a barrier when you’re a female-founded startup. We’ve been told ‘no’ more times that I care to remember. Navigating this world has forced us to be creative about our solutions and to communicate in a clear, firm way in order to get the results we want.” —Breezy Griffith, Skinny Dipped

“Finding that first contract manufacturer was a huge hurdle. I felt a lot of skepticism and condescension. To packers, I was just a lady with some hard-to-make Indian sauces; it looked like a long-shot project to them.” Maya Kaimal

“I came from a nursing background [with] no experience in a business or corporate setting. Deciding to start a company selling laundry detergent was like a toddler taking those first shaky steps. As time went on, I continued to reach out to local entrepreneur services and mentors, other small business owners willing to share notes, and my very wise and supportive husband. There have been so many obstacles but I rarely take no for an answer and love the challenges. Ask for help! Most people want to share what they’ve learned along the way.” —Monica Leonard, Molly’s Suds

“Our biggest challenge has been staying true to our values when it’s much easier and quicker to compromise. Challenging the norms of what’s typically put into packaged food hasn’t been the easiest journey. We overcome these challenges with patience, hard work, and reminding ourselves of our commitment to a real food movement.” —Rita Childers, Core + Rind

This past year challenged us all in many ways. What’s a lesson you took from 2020, whether about business, personal well-being, or both?

“2020 has shown me what matters most to me at the most basic level. Even though business growth was challenging. I personally felt it was a great year for us as a family. We learned to be happy with each other, to find joy in our home in activities we did together vs. always looking for joy outside. I really hope I continue to nurture the joy in being with my close family.” —Richa Gupta, Good Food For Good

“Our business has been growing at an unprecedented rate, which pushed me to really reach out to other founders to learn how they’re navigating COVID. This has created more connection with people who were struggling with similar challenges to myself, which offered me a sense of community even though the world was shutting down. It also highlighted how valuable learning from other people’s experience can be. The big takeaway is: Everyone is going through their own challenges, regardless of the stage of their business or career, and there are always ways you can support them. Even if they’re farther along with their journey. Even with people who are doing something very different from you.” —Carly Stein, Beekeeper’s Naturals

“It taught me to simplify my life and be grateful for the things that I have taken for granted for a long time. Seeing how the pandemic is impacting our lives and mental health, I decided to focus on the two most important things in my life: my health and family. I’ve had the tendency of prioritizing work over my well-being throughout my career, but since last year, I decided to better take care of my physical and mental well-being, starting from the food I eat, exercise I do, and activities I do to release my stress. I also started thinking a lot about my aging parents, who I will not be able to see forever, so I visited my family in Korea at the end of last year, which helped me greatly to regain my motivation and energy while doing the same for my parents. Now when we go back to normal (hopefully soon!), I am ready to cherish every single moment and opportunity to be happy and would like to make a lot of great memories with my parents by traveling together.” —Yanghee Paik, Rael

“Business: just because you have an anti-stress product does not mean that building a business isn’t stressful (especially during a global pandemic!). Personal well-being: Community is immunity. Give the love you want to receive. —Jessica Assaf, Prima

“The lesson I took from 2020 was surrender. 2020 was the one year anniversary of Winged as well as the birth of my first baby, my son, Wolfie. I was seven months pregnant when COVID hit. The one thing they tell a woman during pregnancy is to stay calm and the baby can feel your stress. Navigating the pure terror of COVID, especially when it was so new and we knew so little, while being so close to my due date was truly an exercise in extreme letting go of control. I would pray and repeat the word surrender as a mantra to myself throughout that time and it truly helped me get through it.—Jessica Mulligan, Winged

“This past year has forced me to let go of the constant need to be doing something and has taught me that quiet moments can be fulfilling. They force me to live in the moment and enjoy the little things along the way. Things were so busy last year and the lines between work and home blurred so much that we all had to work together to ensure those quiet moments. We harnessed a high degree of flexibility, support, and empathy for each other. The distance that [the pandemic] put between all of us actually served to make us work more effectively and strengthened our sense of camaraderie; we were always a strong team but are even more so after last year.” —Breezy Griffith, Skinny Dipped

Hold your people close. Now more than ever, it’s so important to invest in the relationships that mean the most to you—and to take stock of all that you’re grateful for. This year, I’ve learned how to lean into my community, how to be perceptive about needs, how to give and show support, as well as how to ask for help, and receive help, too.—Kaitlin Mogentale, Pulp Pantry

Life is full of the unexpected. You cannot plan for it. You cannot prepare mentally for it. So you have to keep healthy mentally, financially, and relationally so that when something happens (because it will) you are in the best scenario possible. Personally, I took the time [during the pandemic] to really get my fitness in check. I made a decision to do something for an hour every day and to wake up before 6 am to get a head start on the day and make time for coffee with my favorite human, my husband. It is a CONSTANT work in progress, but having the opportunity during the lockdown for setting new habits was a huge help!” —Monica Leonard, Molly’s Suds

“Trust our instincts and stay grounded in our values and goals. Last year made the entrepreneurship journey even more of a roller coaster than it already was. We ran into many obstacles, like ingredients and jar shortages, shipping delays, launch delays, having to pay for some of these things much further in advance while at the same time some retailers paying much later thus creating new cash crunches, etc. In retrospect, 2020 made us better businesswomen and created a lot of gratitude for us as well.” —Rita Childers (shown with co-founder Candi Haas), Core + Rind

We’ve noticed that female entrepreneurs often get treated differently than their male counterparts in the press. (For instance, male entrepreneurs aren’t typically asked about how they handle work/life balance or their self-care rituals.) In the spirit of challenging stereotypes, what’s a topic you wish you got asked about more often?

“In my experience, there is more pressure on female entrepreneurs to share different aspects of their lives to create an example of a ‘woman who can do it all.’ This is tough, because ‘doing it all’ can be very subjective depending on who you’re talking to. My partner has been an entrepreneur for ten years, and he has never been asked about his wardrobe. He’s never expected to take selfies and share intimate aspects of his life. On the flip side, there can be a lot of beauty that comes from sharing who you are with your customer. I have a ton of admiration for my female counterparts who feel very comfortable putting themselves out there, but taking on all of the pressure and stress of running a business with additional expectations (social media and otherwise) definitely creates a system that holds female entrepreneurs to a different standard. Some days, I’m exhausted from being on conference calls for 12 hours, and I’m expected to top that off with a very bubbly live Instagram interview. Good or bad, it does feel to me like a gender-specific difference that we should have an ongoing conversation about.” —Carly Stein, Beekeeper’s Naturals

“I wish we were asked how our female intuition gives us a competitive advantage in business. I wish we were celebrated for our feminine-leading qualities and strengths, supporting the idea that you don’t have to be “masculine” to be taken seriously in business. As a female entrepreneur with a Harvard MBA, I wish I was asked about my educational pedigree and why I chose to get my MBA. And I wish we were asked how male business executives and investors can create a more equitable environment for emerging and established female entrepreneurs. Rather than focusing on our beauty and self-care routines, I also wish women were asked about their personal productivity and biohacking tips.” —Jessica Assaf, Prima

“I really wish female entrepreneurs got asked about what inspires them and what their vision of the world is. I truly believe that’s an area where a female point of view would really add value in a patriarchal economy. Women tend to see the world differently; their approach to solve problems is very different from men’s. I think if we could bring those ideas together we can really bring change to many issues we face today.” —Richa Gupta, Good Food For Good

“Instead of the hurdles we faced as female entrepreneurs, I wish there were more questions about our ambition and vision for the future. In many cases, female entrepreneurs do not think much about our gender when we are creating something awesome and running our own business. In fact, we are equally full of motivation and ambition to make a meaningful impact on the world for both men and women. So, I hope we’re treated the same way as our male peers, who often get asked about their next move, vision, and the greater impact they’re envisioning to make as a leader.—Yanghee Paik, Rael

“I think there is not enough information about fundraising from female founders. Every time I am asked to speak or write to a group of entrepreneurs I try to be as open and transparent about what I learned in the process so hopefully it can help another woman who is building her business.” —Jessica Mulligan, Winged

“Drive and ambition, without the negative framing those things unfortunately often carry with them. Society celebrates ambitious men, but when women are ambitious it’s often framed as aggression or rudeness. I’d love to see the female ambition approached from the same place of curiosity and celebration that is afforded to men.” —Breezy Griffith, Skinny Dipped

“I wish female entrepreneurs were asked more about how they reach the top echelon of performance. Whether it’s through morning rituals, coaching, meditation, mentors, or hobbies that fuel their drive, all of us have ways of cultivating the entrepreneurial mindset that’s necessary to achieve almost impossible odds. I would love to share more of this wisdom amongst the founder community. For me, there’s a spiritual side to learning and reflecting on my journey building this business, which sounds woo-woo but has been very effective and comforting for me along this winding path. The more we can share our tools, the more that we all can thrive and cultivate a healthier ecosystem for entrepreneurs.—Kaitlin Mogentale, Pulp Pantry

“Women are often viewed as mothers and wives and not business owners who, like men, are partners and parents. It’s like it is a weakness, as a female, to raise a family, be a supportive mate, and run a company. F*** that. We all need supportive significant others and sometimes domestic help to get it all done. Our children are better for it to see hard-working parents. We just need to ensure that relationships stay the priority and I think we all need to work on this when we are busy all the time. So maybe ask me how my husband supports me or how WE keep schedules straight or the house clean.—Monica Leonard, Molly’s Suds

“I think asking women entrepreneurs about their work-life balance is EXACTLY the right question. It shines a light on the fact that working for yourself is a professional path that allows us to strike a better balance. I hope the 9-to-5 world evolves to be flexible to the realities women face in their lives, whether it’s caring for loved ones or returning to work after time off to be a mother.” —Maya Kaimal

I would love for women leaders to be asked: Why did you start your business and what inspires you (your “why”)? With men in the lead in most industries, there’s a major bias in our systems and structures. From what we’ve seen, most women who start their own businesses have an extraordinary “why” that goes beyond any monetary goals. It’s usually a “why” that’s challenging societal norms, stirring things up and putting something really beautiful into the world. Women’s stories matter deeply in the journey to smashing stereotypes.” —Rita Childers, Core + Rind

These responses have been edited and condensed for clarity.

This article is related to:

Female Empowerment, Food Industry

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Kirby Stirland

Kirby Stirland is a writer, editor, and New York transplant living in Los Angeles.

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