Navigating business challenges can feel like steering through a storm—the journey is unpredictable and demands creativity, resilience, and strategic thinking. Common hurdles such as anticipating market demands, navigating tough economic conditions, and achieving financial stability are often shared experiences among founders. In fact, we were able to tap into 28 female entrepreneurs who’ve faced their share of obstacles head-on, ultimately turning those potential setbacks into stepping stones for success.
From modifying products to serve a larger audience to turning constraints into solutions and finding a niche, these insights provide invaluable real-world wisdom. As you learn from these women’s journeys, we hope you are inspired by their innovation, flexibility, and willingness to pivot—all of which ensured their businesses didn’t just recover but truly thrived in the midst of adversity.
Embrace “no” as a tool for strategic decision-making
Bosky Mukherjee, Founder of PMDojo, helping women and people from minority groups fast-track their careers in the tech industry.
“Balancing life as a bootstrapped founder and working mom brought me face to face with my biggest challenge: financial stability. Deciding how much of our revenue to reinvest in the business versus allocating to scholarships without tapping into my family’s savings was a constant struggle. The lesson was tough but clear: saying ‘no’ is sometimes necessary. Whether it’s rejecting clients who can’t pay or adjusting scholarship offerings, these decisions are crucial for sustainability. I shifted our approach by introducing a tiered pricing model and aligning scholarship allocations with our financial reality. This strategy ensured we could serve our clients effectively without compromising our business’s health. To fellow entrepreneurs: financial sustainability is paramount. Making hard choices is part of leadership. It’s not about being ungenerous but about ensuring your business’s longevity. Embrace ‘no’ as a tool for strategic decision-making and growth.”
Turn challenges into opportunities
Victoria Repa, Founder and CEO of BetterMe, a health and wellness platform providing a tailored holistic approach to well-being.
“For a business headquartered in Ukraine, the biggest challenge has been the Russian war in Ukraine. People have been experiencing this war differently, but 80% are under permanent stress. Because victory is a state of mind, we created a corporate wellness program that emphasized mental and physical health for our team and then adapted it to work for any company. This approach lets us turn war challenges into opportunities, resulting in revenue and team growth.”
Seek ways to enhance your offerings
Ronit Menashe, CEO and Co-Founder of WeNatal, the first prenatal supplement intentionally optimized for her and him.
“Approximately six months after our launch, we had the opportunity to work with an incredible advisor, Kathie Swift, a leading functional nutrition dietitian. She shared some groundbreaking research that was yet to be published. This put us in a challenging position. Our formula was already considered the most premium in the industry. So we had to decide whether to reformulate based on Kathie’s feedback. After careful consideration, we chose to take the path of innovation, constantly striving to make our products even better. This experience taught us the importance of remaining open to new information and constantly seeking ways to enhance our offerings. It reinforced our commitment to innovation and providing the best possible products to support our customers’ fertility journey.”
Don’t put all your eggs in one basket
Julie Zhu, Founder of Julie Zhu LLC, an award-winning marketing strategist who specializes in elevating brands’ visibility and impact.
“When I first started, I heavily relied on Facebook for one client. I soon realized the danger of depending on a single platform due to risks like account issues or algorithm changes. So I diversified into using multiple platforms and channels, customizing strategies to each client’s needs. Don’t put all your eggs in one basket; diversify and adapt based on data and feedback.”
Don’t be afraid to pivot to keep your prices competitive
Jessie Young, Founder of Halo, a global collective for e-commerce, mentoring, advisory, and events.
“Halo launched as an e-commerce website for halo headbands—made by women, for women, from sustainably sourced materials in developing countries. When pandemic border closures fundamentally stalled material imports, we moved to onsite production and a ‘Just In Time’ (JIT) supply chain. This strategy meant we moved materials right before they were needed, resulting in little or no inventory stockpiling and a truly agile DTC model. We augmented that vertical with a mentoring and advisory arm to create new lines of revenue to offset the incremental costs of a JIT supply chain and ensure we could keep competitive consumer-facing prices.”
Leverage the power of personal experiences
Rashmi Rao, Founder of HLWF ™ Alliance, a nonprofit community of women leaders, health heroes, and wellness wizards.
“Our key hurdle was fostering collaboration among professionals with varied backgrounds and views in a singular platform. Our aim was to preserve each expert’s unique contributions while bridging gaps for mutual understanding. Our strategy? Emphasizing personal lived experiences alongside professional expertise. This blend of personal narratives with professional knowledge not only enriched our collective problem-solving capabilities but also strengthened our foundation, ensuring our alliance recovered from initial challenges and thrived. We recommend this strategy to entrepreneurs facing similar challenges: leverage the power of personal experiences to foster a deeply connected and collaborative community.”
Invest in setting yourself up for success
Sarah Loughry, Founder and CEO of Em Dash Content Studio, a team of expert writers and strategists that help businesses establish themselves as thought leaders.
“During the downturn of the economy, we lost two large clients due to financial cuts. To that point, I’d only taken on a few larger accounts to help supplement the much smaller accounts we serviced. After panicking and having a wallowing fest, I decided to invest in a fractional CFO to evaluate our offerings and secure our position for the future. After three months of working with her, we saw a tremendous difference. The reality is that smaller businesses can’t always afford a fractional CFO. But you can invest in workshops, courses, or one-on-one consultations to make sure you’re set up for success from the beginning.”
Outsource tasks even if you enjoy them
Nicte Cuevas, Brand Strategist and Designer at Nicte Creative Design, connecting color, culture, empathy, and design into a purpose-driven brand strategy for visionary companies.
“A few years ago, I had been running my business like a bullet train because I was trying to make up for ‘lost time.’ After my son was born early and spent a long time in the NICU, we endured a lot of trauma. After he left the NICU, I had to figure out a way to keep my business afloat. In the last two years, I have been able to put the focus back on my business, but I felt I had to triple down to catch up. That false ideology burned me deeper into the ground than I cared to admit. Before planning a strategy, I took a profound reflection on stepping away from negative relationships and environments that didn’t inspire or challenge me to grow. Then, I had to come to terms with outsourcing tasks—even if it was something I enjoyed. I made a list of tasks I needed help with and calculated which would save me the most time and were most cost-efficient to outsource. This allowed me to focus on bigger-picture solutions and gave me some time to breathe and slow down.”
Embrace the changes you are met with
Muirgheal Montecalvo, Founder and CEO of TripFusion, a platform offering integrated booking solutions for the hospitality industry by simplifying operations for hotels.
“The biggest challenge our business faced was shifting from a B2C to a B2B model, which involved reorienting our entire team and operations to suit a new market. We emphasized clear communications for the reasons we were making the changes, trained the team on the B2B dynamics, and revamped our product development to meet business clients’ specific needs. We refined our customer support and marketing strategies to cater specifically to business clients. For entrepreneurs in a similar situation, embracing change, ensuring team alignment, and customizing your approach to meet the new market demands are crucial steps toward not just recovering but thriving in a new business model.”
Lean into your personal struggles to effectively support clients
KK Hart, CEO of Hart Marketing & Communications Inc, a multi-disciplinary business advisory and marketing company.
“As the face and name of my business, my health scare in February 2020 was a massive and potentially catastrophic challenge to overcome. I am known to be a health, fitness, and wellness business expert. Yet I was petrified of the unknown. I found that creating and implementing my own unique method of mind and body practices helped me to use the challenge as an excuse to optimize my health and wellness and level up my skill sets even further. The best part? I was able to return to work instantly post-surgery with a cancer-free diagnosis and one of the speediest recoveries my doctor had ever seen. This allowed me to lean into my clients’ struggles and needs with a stronger perspective of how they could grow and thrive despite the fear and hardship themselves.”
Modify your product to serve the needs of a larger audience
Claudia Richman, Co-Founder of Starling Training, offering cohort-based, virtual, synchronous training designed to sharpen the skills that build productive, supportive relationships.
“We started our business focusing on helping boutique software consulting firms develop skilled managers. Over the past year, the economy has been particularly tough on these companies. So we’ve modified our courses to help companies in other industries and created a version of the course to help managers thrive in M&A situations. Everyone needs great managers—no matter what industry or sector. Modifying our product to serve the needs of a larger audience helped us through this most recent tough time.”
Think outside the box
Dom Farnan, Founder of DotConnect, conscious connectors who work with intention to build outstanding teams and stellar corporate culture.
“Last year was the hardest year I’ve ever faced in business. We downsized our team tremendously. One thing that helped me navigate the turbulent times was to experiment. Thinking outside the box and not getting attached to the outcome can feel empowering in tough times. I also created space for myself as a leader to receive less input from outside voices so I could arrive at decisions that felt most aligned with my long-term vision and values. I learned more about myself last year than I did in the previous 20 years in business.”
Explore multiple sales avenues
Allison Ullo, Founder and CEO of Leaves of Leisure, a luxury tea brand with a focus on herbal and low-caffeine teas, created to bring peace and pleasure to ordinary days.
“One of the biggest challenges in starting out was relying solely on online sales when I had no budget for ads. It limited my reach and growth potential, and I found myself feeling frustrated and defeated. To overcome this, I diversified the sales channels by participating in in-person events like markets and trade shows. This not only expanded the customer base but also allowed me to establish personal connections and build brand loyalty. My recommendation to entrepreneurs facing similar challenges is to explore multiple sales avenues and engage directly with customers to understand their needs and preferences.”
Invest in hiring experts that can help you
Lauren Maffeo, Author of Designing Data Governance from the Ground Up, a 100-page, six-step guide to help leaders leverage data as a competitive asset.
“If writing a book is no easy task, promoting that book is even harder as a first-time author without an agent. It felt daunting to learn how much money and time I’d need to spend making sure that my book reaches the right audience. I helped solve this problem when I acknowledged that I couldn’t do all the PR on my own. I hired a publicist on retainer for three months. It was an investment in work that I could have done myself, but not if I wanted to avoid burnout. My publicist took a big load off my plate, which allowed me to focus on other work that I needed to do myself.”
Prioritize ruthlessly
Kelly Hubbell, Founder and CEO of Sage Haus, an online platform helping busy moms have it all without doing it all by outsourcing the mental load and reclaiming their time.
“In a world that feels saturated with content, the biggest challenge for me as an entrepreneur is consistently growing my audience and reach. The strategy to successfully achieve this is ruthlessly prioritizing. Time is our scarcest resource. In order to make the most of the time we are able to dedicate to growing our business, we must get comfortable with ruthlessly prioritizing. This looks like blocking out calendars for productive, focused time and applying boundaries to competing priorities.”
Be intentional about the community of support you build
Marianna Sachse, Founder and CEO of Jackalo, America’s first circular children’s clothing brand.
“One of the biggest challenges has been starting a business in isolation. At the time I started, I was living abroad, so I felt very disconnected from an entrepreneurial community. I dove deep into podcasts and books that led me to online communities and helped me establish a roadmap for building out an in-person community of support. I’d highly recommend other founders not go it alone. This doesn’t mean having a co-founder. It can just mean being very intentional about the community of support you build.”
Build a team around your company values
Brittany Woitas, Founder of Kōvly Studio, a brand and marketing agency for experience-driven brands.
“The one thing that I believe will make or break an entrepreneur is their people. Without question, the biggest challenge I’ve navigated as an entrepreneur is building a team and culture that supports our core values. It’s imperative that you get clear about what your company really stands for and build a team around that.”
Transform challenges into opportunities
Ariana Rodriguez, Founder of AR & Company (ARCO), a boutique consultancy specializing in operational excellence and strategic growth for small businesses and startups.
“The biggest challenge our business faced was navigating negative client feedback that led to a refund request, which was a situation that deeply impacted us given our commitment to excellence. In response, we undertook a comprehensive overhaul of our client engagement process, focusing on clear communication and setting realistic boundaries to manage expectations effectively. This strategic realignment not only fortified our service delivery but also empowered our team to provide exceptional experiences consistently. We recommend this approach to fellow entrepreneurs as a means to transform challenges into opportunities for growth and client satisfaction.”
Reevaluate your business model when necessary
Katherine Sprung, Founder of Squish Marshmallows, a small batch, handcrafted marshmallow and confections company in NYC.
“After making it through the height of the pandemic, our store’s lease was about to end. It was initially tough, but my decision to close the retail shop and change the model of the business could not have been better. Operating a retail and D2C e-commerce site carries a lot of overhead and miscellaneous stressors. Switching to a bespoke approach and fulfilling special, custom, corporate, and catering orders has really streamlined the process and increased margins. Sometimes reevaluating your model can change your business for the better!”
Plan your business 90 days in advance
Lauren Loreto, Founder and CEO of Brand Good Time, a marketing and web agency for growth-stage startups looking to increase their visibility.
“In November of 2023, our finance team let me know that if we didn’t get sales, and get them ASAP, we’d be looking to lay off an employee come January. I fought tooth and nail to create some contingency plans with sales and generate more cash injections. I succeeded but not without many sleepless nights. My advice to entrepreneurs in a similar situation of wondering if they’ll make the next payroll is this: always plan your business 90 days in advance. Create contingency plans for sales tactics if you’re not hitting goals and have extreme oversight on your financial projections.”
Create a recurring revenue pricing model
Meredith Noble, Co-Founder and CEO of Learn Grant Writing, helping those looking for a flexible career change become well-paid grant writers.
“I did everything to find customers for our original online grant course and make $7,000 at best each month. We turned our sinking ship around and got to $1 million in annual revenue in just two years by creating a recurring revenue pricing model. I always say, ‘Sell once,’ and don’t guess what your customers want or need. Instead, conduct robust customer journey mapping so your offered solution can perfectly address where your customers are at and where they want to go.”
Find a niche and be the best at it
Marnie Rabinovitch Consky, Founder and CEO of Thigh Society, the leading direct-to-consumer brand of size-inclusive long-leg undergarment solutions.
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“Thigh Society always faces the pressure for growth. Over the years, many so-called experts have tried to convince me that the next logical step was to expand our product offerings. I’ve decided to stay focused on becoming the world’s No. 1 brand of long leg underwear for women—a category we helped to create. We’ve just expanded to Australia, with more markets to come. We have continued to invest in research and development to offer best-in-class products. I’d recommend other entrepreneurs find a niche and be the best at it.”
Revamp your offering structure if needed
Emilie Mascarell, Founder and CEO of Emilie Consulting, a consulting agency specializing in fragrance and beauty product strategy and development.
“We took on too many small projects, leading to a roadblock without having the revenues to hire more resources to support the workload increase. To tackle this challenge, we revamped our offering structure and introduced an advisory program. This allows us to continue supporting startups with affordable pricing in a more sustainable way.”
Ensure people will pay for your product before building it
Ashley Chang, Co-Founder and CEO of Sundays, an executive assistant service for working parents.
“After 10 years as a product manager, my first instinct when starting a company was to build a product and get to product-market fit. We spent months building a product only to realize we had no distribution. When we pivoted, we decided to focus on building the business first. We learned the only way to know if something is valuable enough for people to pay for is if people will actually pay for it. Now, I look for at least 10 people who will pay for something before spending time building, and I plan to do that for any new product.”
Become proficient at budgeting
Anouck Gotlib, CEO of Belgian Boys, creating whole ingredient foods with a European twist so families can prepare less, smile more, and indulge better.
“One of our biggest challenges to date has been budgeting. The first year we really did a formal budget and baked too many risks into our expectations. Things didn’t come together the way we expected—life happens. It forced us to recalibrate. Re-planning our year and pulling back from investments was a huge challenge. We took away some priceless learnings from the experience and totally changed the way we look at budgeting, forecasting, and how we feel about risks and opportunities. Now we’re at the point that we are meeting or exceeding our forecast, which is a much more comfortable and exciting place to be!”
Prioritize self-care and delegate tasks
Stephanie Loewenstern, Founder of Bright Link Talent, a woman-owned recruiting firm that places top, diverse talent for high-growth startups and technology companies.
“One of the biggest challenges my business faced was balancing my personal and professional life, especially after encountering an unexpected, life-changing event that significantly impacted my business for several months. To navigate through this period and ensure not just recovery but growth, I actively sought out support networks and made the strategic decision to hire additional help. This approach allowed me to realign my focus, efficiently manage my responsibilities, and ultimately thrive in my business. I recommend entrepreneurs facing similar situations to prioritize self-care and delegate tasks, as it can profoundly influence both personal well-being and business success.”
Turn constraints into solutions
Kat Lourenco, Fractional COO and Coach at Kat Lourenco Co., working with a new generation of leaders to avoid overwhelm, overwork, and burnout.
“Every business, including mine, has constraints: time, money, and resources. Avoiding them is nearly impossible. Expecting them to be ‘overcome’ can be paralyzing. Instead, I try to think of constraints as my competitive advantage. They prevent me from doing many things, but they enable—even demand—that I do one thing incredibly well. Constraints don’t have to be a problem. In fact, they might be the solution you’re looking for.”
Communicate as if you’re already where you want to be
Allyn Rose Oertel, Founder and CEO of The Previvor Foundation, the first-of-its-kind, digital women’s health platform aimed at helping women navigate their breast health.
“Like most startups, we suffered from the ‘too small’ problem. When you’re an organization of one, two, or three, it’s hard to gain the attention of large donors or partners scared to hop on board an ‘unknown’ company. Changing the way I communicated about The Previvor—using words like ‘we’ even if it was just ‘little old me’—communicated that the organization was larger. It seems like a no-brainer, but so many startups and small businesses spend time apologizing for their size instead of communicating like they are already where they want to be. A little word change can help you fake it until you make it a reality.”
Dreamers & Doers is an award-winning community that amplifies extraordinary women leaders, investors, and entrepreneurs by raising their profile through PR, forging authentic connections, and curating trajectory-shifting resources. Learn more about Dreamers & Doers and get involved here.