Katharine & Tiff’s Startup Journey

A white sign on a wooden window sill that says in black letters, “Turn ideas into reality.”
Photo by Mika Baumeister on Unsplash

ife is strange, and it takes examining your failures to appreciate how chaos, rejection, and redirection are the fertile foundations for becoming a successful individual. We don’t define success as possessing an excessive amount of financial wealth. Instead, success is the ability to look back onto a journey full of relationships, experiences, and changes. Success is surviving even when you wonder if it’s worth it.

There’ve been plenty of times Katharine and I wondered if any of what we were doing was worth it. Both suffering from autoimmune diseases and subsequent illnesses, we’ve had our fair share of moments where we just wanted to give up. But one thing we shared, which fuels our souls and the reason we keep pushing, is the love for community and the peace it brings.

We try anyway, knowing the odds. How would you put it, Katharine?

hat’s right; we keep going. I used to have this sentence tapped to my apartment door during conservatory, “Fail and fall fearlessly forward.” I can’t recall now if I made it up or heard it somewhere, but I knew I was in a unique moment when I could fail every day and still be safely in training, not in the “real world” yet with hard consequences of completely flopping.

So I looked at that sentence each morning as I left for class or rehearsal and tried to take that courage with me. More than a decade later, I still try to carry that sentiment into each new endeavor — through completely failing at multiple careers, folding a business, battling with the effects of a lifelong diagnosis, becoming a parent, you know…the human stuff.

And at the end of every day, or project, or opportunity, I get to reflect on those failures and notice that the joy or relief or win came when someone lifted me off the ground. I have often witnessed — and I look forward to a lifetime of this — that my community supports me along the next stages and helps me celebrate. Whether it’s my little family, or a whole company cheering along, it’s community that brings the sweetness to life and keeps me going.

agree, and our passion for building and leveraging communities is how we connected!

Katharine and I met at Flatiron School, formerly part of The We Company. I hadn’t a great start in joining as, at the time, I had been hospitalized and received changes to my diagnosis. I was torn between remaining silent about how I was struggling and speaking out in hopes someone would understand and that we’d be able to support each other in a world where medical accommodations just aren’t yet proactively a part of an employee’s experience.

I remember sitting at John F. Kennedy airport to board a flight to our company’s summer camp, and she coming to sit beside me. After introductions, Katharine briefly shared her concern about the cold temperatures in England where we were headed and that she was afraid of getting sick.

I had just been released from the hospital a few days prior. In pain and barely awake from my medication, Katharine startled me with her honesty. I began to share what I was going through. Soon after, we started sharing ways to improve the internal company culture by forming unofficial employee resource groups and creating spaces where our colleagues could be their authentic selves.

Having joined before me, Katharine and several others had already created spaces to foster conversations centered on diversity, inclusion, and belonging. To top it off, she was a real hustler at that company, collaborating with whomever she could to host a range of events where company partners and students would come together to build meaningful connections.

Katharine, do you remember that?

my goodness, of course, I do. I still remember how afraid we both looked and felt. We were heading off to a weekend-long event in another country and wary of support available to people of varying needs — and having no understanding of how we could seek out help when we needed it.

Our experience that long weekend propelled us into work that brought attention to the need for more inclusive practices at our company. The first step I took was to request leading a company lunch and learn session. I made sure to invite our company founder, CEO, and COO, and with a shaking voice, I got up and shared my story.

Writing that now it doesn’t seem like such a big deal, but at that time, there was not such a focus on inclusive work cultures as there is today. As a new employee of a young, high-growth organization, where mandatory company activities assumed all employees were healthy and without disability, it was a scary action to take.

I confessed that what my colleagues saw every day was not who I actually am. I showed images of what my intestines look like when I have a flare-up, what my hip now looks like after a full replacement, and initiated a conversation about ways we could be more inclusive, and how that could help us thrive. I was so lucky to have Tiffany’s support in creating that talk. Without her unwavering belief that I was taking the right action, I couldn’t have gotten the nerve to be so vulnerable in that setting.

It worked. I first started to hear from colleagues individually about struggles with their unique circumstances at work. Eventually, there was a company-wide ripple effect from teams documenting work — so that co-workers could pick up the slack when someone was ill — to the company providing more space and resources for events and panels that highlighted under-represented groups and beyond. We didn’t know where our convictions would lead, but we moved forward, hoping to help shape a more inclusive environment for our colleagues and ourselves.

m so glad you led that lunch and learn. It wasn’t until after that meeting that we all came together and started opening up and finding ways to support each other and receive support.

We both continued to find ways to build communities together internally and externally. However, during this time, I learned two things. First, high-growth startups were equally bad at centering diversity, equity, and inclusion efforts at their companies as their larger counterparts. Second, so much, that lack of centering went beyond leadership and gave me insight into how that disregard was perpetuated.

Companies that do not prioritize diversity, equity, and inclusion and fund emerging startups need to develop a sourcing strategy for funding diverse entrepreneurs. Yet, I was brought back to the issue of company employee resource groups still not getting the support they need for improving company culture. It isn’t their responsibility to build and nurture a company’s culture; it’s everyone's responsibility, especially leadership.

If the lack of support employee resource groups received remained an issue, how the hell could anything else be accomplished if we can’t support each other and appreciate and protect each others’ authentic selves?

I tried working through these problems and didn’t expect to pursue them as a business opportunity but merely as a proposal for whichever employer I had been working at the time.

Last year, between surgeries and treatments, along with an indescribable year, I took some time to think more about these problems. It seemed like now everyone cares about diversity, equity, and inclusion. But I wondered, how many of them were willing to put in the work and to listen?

While everyone scrambled to figure these things out, I decided to put something together and Google my nights away to find programs to help me. I eventually discovered Founder Institue and decided to apply. The incubator program’s equity pool and focus on building impact-driven companies caught my attention.

To be quite honest, after taking their quiz, I didn’t expect to get in. My desire to try anyway came from a need to find a way to scope and solve the problems I submitted. It was also due to my newfound interest in venture capitalism when conducting further research on the issues.

I still had what seemed like different ideas centered on one issue — diversifying and building equitable companies. The only other person I could think to reach out to for help was Katharine. Through her creativity, perspective, and experience, we began shaping the problems, and finally, through research and interviews, deciding on one we believed had a significant impact.

Katharine, who would’ve also thought that our experiences as unsuccessful entrepreneurs our first time around, and recent experiences, would lead us here?

can certainly say that when my sustainable yoga clothing company closed, I never thought I’d have the title “Founder” next to my name again. I had set out to empower people to feel good about their bodies and who their clothing purchases supported. By creating a brand produced and designed in NYC, I wanted a portion of those purchases to go to local nonprofits.

I had limited experience as a marketer at the time and no experience in developing and executing a scalable business strategy. I also couldn’t find a mentor I could go to for advice within that space.

What did come out of that three-year-long adventure was some more humility (which I am better for) and an incredible trust in the community cultivated along the way. From customers, designers, friends who lent their skills and resources, and other female founders, I knew that something bigger than all of us could emerge if we banded together. Hope and ambitious strides towards a more accepting space for anybody, with any body-type, to work towards their wellness goals.

eah, my first time around was focused on finding ways to bring tech engagements to underserved communities to give them the power to leverage the tools gained to solve problems within their community. However, I was just learning the importance of a network and didn’t know anything about creating a sustainable business and executing a business plan. Mostly, I thought I could just do it all myself. What an oddly selfish behavior to apply to community building, I now think to myself.

Combining our persistence, experience, and passions, we decided to do it again — together. Whatever successes or failures may come of it, I wouldn’t have wanted to share them with anyone else but Katharine.

Katharine, want to take it away on what we’re building?

es, please — with joy! Taking the lessons learned from our previous entrepreneurial pursuits, our belief in inclusive communities, and our convictions to support more underrepresented founders, we‘re building a social network marketplace for underrepresented and underserved early-stage entrepreneurs to make connections and gain the tools and feedback they need to grow.

According to a 2019 Morgan Stanley report, venture capitalists miss out on roughly $4 trillion in value by not investing in more diverse entrepreneurs. With America projected to be a minority-majority country by 2046, if we aren’t intentional about investing in underrepresented founders, the value of missed opportunities will increase.

However, gaining access and visibility remains a disparate and challenging experience for diverse founders. Aside from social media hopping and the noise that comes with it, most exclusive entrepreneur networks create entry barriers — be it an application process or expensive entrance fees.

The Cowrie mobile app is prioritizing access and support for underrepresented and underserved early-stage entrepreneurs. When more diverse founders have access to what they need to build and scale their businesses, it’s my purview that we will see a ripple effect throughout our economic landscape.

From representation across leadership to diversity in the employees they hire to inclusive practices and policies, we will have a workforce and workplaces that are truly reflective of the world we live in. Cowrie will help us get there.

t’s diversifying and building equitable companies about which we’re equally passionate. Though we realize, sometimes passion can be blinding, and that is why we’re seeking feedback and support.

Let’s be real. This new journey on which we’re embarking is exciting yet scary. To our current advisors who talk some sense into us, folks who’ve volunteered their support, and our #1 fans, we appreciate you. Thanks for reminding us why this is important and why we need to keep pushing.

Data-driven solution & information experience designer creating impactful, diverse, & inclusive digital experiences. Proud first-generation Caribbean-American.

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