Adonica Shaw, Founder & CEO, Wingwomen

10 Harsh Lessons I Learned While Building Wingwomen, a Women’s Health Startup

Adonica Shaw

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A few weeks back, I had the privilege of joining a podcast hosted by Startup Health, where I discussed my journey of establishing Wingwomen, a Femhealth startup dedicated to facilitating virtual and in-person access to Gynecology, Family Planning, and Doula Care. Following the podcast’s release, I received several inquiries about my experiences as a female founder and CEO, particularly as a person of color, and how my commitment to patient advocacy has shaped my approach to healthcare innovation.

*In the spirit of transparency, I write from a place of genuine affection. My journey has been marked by its fair share of missteps, and it is precisely these errors that allow me to offer these pieces of wisdom. It is not my intention to present myself as perfect, but rather, to openly share these reflections in the hope of sparing others from unnecessary hardships.

Innovation isn’t always enough. Be prepared to pivot.

When I introduced Wingwomen in 2021, the original vision aimed at creating a peer support platform for women navigating the complexities of reproductive health. While the concept garnered initial excitement, its monetization proved challenging, compounded by concerns about the potential dissemination of medical misinformation, hindering scalability. Over the course of several months, our brand underwent strategic pivots, incorporating elements such as health coaching and reproductive health literacy to better align with our target market. Despite the logical adjustments, achieving the company’s current status required yet another pivot. The journey was far from straightforward. Navigating the intricate process of finding the right market fit is a familiar struggle for entrepreneurs, but when a complete restart becomes necessary, the temptation to fold the venture is present. I’m grateful for staying the course, as it ultimately led us to a solution that caters to everyone while establishing a viable monetization pathway.

If you are a person of color, you may be redirected to funds and investors based purely on your ethnicity.

Race is undeniably a sensitive topic. And when you throw in millions of opinions, billions of dollars, and only so many handfuls of deals each quarter — feelings are bound to get hurt.

Despite my resilient nature, navigating through norms that felt uncomfortably discriminatory has become a part of my journey. While Wingwomen is designed to cater to everyone, it’s disheartening how frequently I find myself redirected to funds specifically for Black founders — even before presenting my pitch. Learning not to internalize this redirection has been essential, as it often feels like being pigeonholed before having the chance to discuss the merits of what we’re building. Understanding that this is not always a personal slight has been a necessary realization, yet it remains a harsh reality encountered people of color face while seeking funding.

Be self-allied. Anything less can impact the people you’re building for.

As a founder, I’ve received a lot of tempting offers. Yet, the harsh reality I’ve come to understand is that a founder’s identity isn’t shaped by the opportunities accepted, but by those consciously declined. Practicing self-allyship affords you the strength to uphold boundaries which are aligned with you and personal values. This form of self-allyship is especially important when navigating compromising situations.

One particular experience I’ll always remember, was when a personal mentor, a well-established IVF physician with substantial wealth, proposed investing $20,000 for a 20% stake in my company. For women and founders of color, the harsh reality is deals like these are disproportionately passed down to us because very few of us have the connections or the relationships to ascend in business otherwise.

Anyone who has raised investment understands the significance of selling 20% of a company, which is generally the amount sold in each funding round. Selling such a sizable equity would have hindered the business’s ability to secure further funding and scale.

As negotiations unfolded, a particularly predatory element emerged: a requirement for Wingwomen to offer a specific C-suite role in exchange for the investment. While investors commonly seek board seats, the notion of essentially selling an employment role raised eye brows and ethical concerns. Beyond the fact that company valuations are not strictly tied to a specific figure (e.g., 20k for 20%), the demand for a C-suite role was troubling. My family questioned why someone who had substantially more would try to essentially take 1/5 of my company, moreover, why would a mentor propose taking something they could build for themselves?

In women’s reproductive health, decisions extend beyond patient experiences. For some, its a matter of life and death. When I think about the Dobbs decision and how it impacted women and birthing families across the country, or when I consider the fact that black women are disproportionately impacted at 3 to 4 times the rate of their counterparts by policies that could be contributing to the maternal mortality crisis, I think about how many of them wouldn’t be facing these issues if the decision makers were more thoughtfully selected . Unfortunately, the trust was strained in the negotiation process, and I walked away from the deal. Accelerator programs taught me to find advisors I could trust, but no one prepared me to know when to walk away from them. So ladies, my advice is to be prepared to walk away in any negotiation.

For women and people of color in business, recognizing where to draw the line is important, as others may attempt to exploit your vulnerabilities.

Don’t pass out equity like Halloween candy.

As a new founder, well-intentioned individuals may propose partnerships in exchange for equity, but niceties don’t necessarily equate to expertise in the areas crucial for your venture. Failing to discern this beforehand could result in significant time and equity loss. Further, it could potentially jeopardize future deals due to unfavorable cap table optics for new investors. Prior to Wingwomen, I received advice suggesting that distributing equity is a straightforward method to kickstart a company. While there’s truth in this, the intricacies are more nuanced. Factors like vesting schedules and the expectation that some individuals retain equity throughout the company’s entire lifecycle add complexity.

Influence and power are two very different things.

In startups, power dynamics are different than traditional corporate structures. My background as a marketer in corporate environments provided little preparation for the stark realities of transitioning to the startup realm with Wingwomen. Here, people with money may have power, but influence often resides in the individuals delegated to communicate with the founders or the public, regardless of their appearance, age, background or pedigree. In start-ups influence often comes from the pack, so assuming you only need to play nice with certain individuals can be a misstep. Unlike other industries, where senior titles and accolades define leadership, startups defy such conventions. Traditional hierarchies are absent, and senior leaders blend within their teams, complicating the identification of decision-makers. Coming from a corporate mindset, I had a steep learning curve — navigating through everyone, and not just senior leadership. Securing a deal might not hinge on an individual with an office or title but could be someone three connections away from a college roommate, linked to a crucial investor. Reflecting on my experience, I would have approached early interactions with a softer touch, extending my time to all and not just a few.

Everyone isn’t building from lived experiences, and that has to be okay.

Within the competitive landscape of healthcare and healthtech, motivations for constructing a company or product are diverse. Some entrepreneurs embark on this journey due to their extensive careers in a specific field or addressing a particular issue, while others leverage unique advantages in the market. As a patient advocate with strong first-hand lived experiences, I encountered a profound learning curve. While personal experiences can indeed enhance the value of a business, it’s imperative to recognize that investment is not automatically granted solely based on having endured challenging circumstances.

The truth is, founders and funders alike ( irrespective of race, socioeconomic status or education) have grappled with various health challenges like miscarriage, cancer, uterine fibroids, preeclampsia, and infant loss, so individual pain alone cannot singularly contribute to the overall value proposition of your company. Throughout Wingwomen’s development, I often contemplated the motivations behind building ventures, even when devoid of firsthand experience. It was only after developing deeper connections with individuals and receiving constructive feedback ( Hello, Maura Rosenfeld) that I embraced the understanding that individuals may be in the healthcare space for distinct reasons — each path deserving respect.

It can be harder to build in healthtech or healthcare without a PhD or advanced Degree on your team.

In the initial year of Wingwomen, I undertook every task independently — from website development and crafting decks to formulating the early business plans. While my capabilities are noteworthy, many heartaches and misunderstandings could have been averted had I sought individuals with advanced degrees for my team earlier. Back then, I believed that having a compelling idea and putting oneself out there sufficed, and to some extent, it does. However, the reality, particularly in healthcare, dictates the necessity of qualified, credentialed, or licensed individuals to effectively establish a business. Whether navigating FDA regulations, fundraising, or securing patents, professional expertise becomes indispensable. This is not an arena where you can wing it, no pun intended. Delegating tasks to individuals with more professional acumen expedited the business’s development. For those lacking advanced degrees, I empathize with the challenge of approaching unfamiliar individuals for assistance. Yet, in the healthcare vertical, seeking help from professionals becomes an unavoidable reality.

Business is war, dress for battle.

If you know it’s going to be 10 below zero tomorrow, you’re probably going to prepare by pulling out a few coats, long underwear, scarves, hats, protectant for your skin, gloves etc. Similarly, launching a startup requires foresight — securing resources, cultivating support, and fostering relationships before entering the scene. Through my experience with Wingwomen, I realized that initiating a startup is akin to declaring war. The act itself broadcasts to the world your conviction that you are the best at what you do, where, and when you do it. Outside of selecting logos, and building a website, I would encourage more female founders to invest in books around strategy. Specifically, I like the “48 Laws of Power” and “The Art of War.”

“The Art of War” imparts valuable lessons on how strategy, timing, discipline, and resources influence outcomes in war. Notably, it underscores the role of deception in all conflicts. Despite the prevailing notion that female founders exist in a harmonious, non-competitive space, the reality is different. Each founder or team possesses unique advantages at different times. A savvy founder strategically utilizes the people and resources around them as formidable armor. This armor may manifest as a cohesive team, the ability to access exclusive resources, alma mater connections, real estate, technology, or financial backing. Recognizing the need for such armor positions a founder strategically for success, regardless of the challenges that may arise.

Some investors will invest in groups, unfortunately it means they inadvertently block some businesses and their pathway to scale.

The stark truth about investments lies in their finite nature. The fact is, they are limited to a select few individuals and companies. While the allocation of funds isn’t inherently malicious, when financial support goes to a direct or indirect competitor it can unintentionally eliminate your company from the competition. If a group of investors chooses to back a specific company or idea, it’s crucial to acknowledge it and move forward. If they perceived you as a competitor pre-deal, they likely did a thorough evaluation, and concluded that you weren’t their optimal investment choice. Persistently submitting decks won’t alter their perspective, and they won’t rescind investments from another company to choose yours. Investment results from myriad decisions involving numerous individuals and factors. The harsh reality necessitates pivoting and identifying your niche audience. An cool piece of advice I received emphasized that, as a founder, I’m not a politician. Simply put, my role isn’t to flip votes, but to recognize and engage my actual supporters. If you find yourself unintentionally excluded from a particular investment or group, try not to take it personally; there’s likely a group or investor out there that will embrace you and your idea effortlessly.

It costs money to raise money. Travel, food, accommodations are not usually covered by investors, so be prepared to pay your own way.

Have you ever encountered social media advice urging you to reject unpaid speaking opportunities and insist on payment from investors or other groups? As a woman of color I gave away a lot of my time, money and efforts into projects in the early part of my career that I eventually go to a place where I decided I would demand payment for everything. What I’ve learned as I’ve navigated this space is that opportunities flow through relationships. And demanding payment from someone who is a “friend, ally or partner” can burn bridges and strain relationships. While in theory, a significant financial investment for participation might warrant some compensation, you’ll likely have to cover your own expenses ( especially if you’ve been around for three years or less). Early on, I mistakenly assumed investors and advisors covered all travel expenses for pitches. This isn’t always true. If fundraising, be prepared to fund your travel. In hindsight, planning for travel expenses would have been wise. Supportive friends who can’t invest financially can contribute to a travel fund. Every little investment counts, especially when you find yourself on a flight, needing to pay eight dollars for in-flight Wi-Fi to fine-tune your pitch deck.

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Adonica Shaw

Adonica Shaw is the founder of Wingwomen, a doula and a midwife in residence.