Why I’m Joining Flybridge Capital Partners

Cherae Robinson
8 min readMay 23, 2022

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I’m excited to join Flybridge as the Head of Community, focused on helping early-stage founders get the support they need to be successful and creating spaces for ambitious entrepreneurs to connect, grow, and expand.

If you follow me, you know that for the past 10+ years I’ve been focusing on connecting Africa and the diaspora, largely through my startup Tastemakers Africa. Disrupting stereotypical narratives, opening up African cities as in-demand travel destinations, working with creatives and hospitality entrepreneurs, and building bridges between Black people all over the world has been the work I could’ve only dreamed of.

Robin and Veronica, early Tastemakers customers on an experience in Cape Town (2016)

I’ve been incredibly fortunate to be a part of a transformation in our cultural zeitgeist where we are now jamming to afrobeats on mainstream radio, booking flights to Ghana with the same zeal as a trip to Paris, and where conversations on diasporan connectivity are happening daily. There is still much more work to do in repairing fractures and creating true connectivity amongst afro-descendant peoples, but when I reflect on where things were when I first stepped foot in Sierra Leone in 2010 to where we are now, I can do nothing but celebrate.

Tastemakers Africa X AFROPUNK Paris (2018)

COVID-19 brought on a unique set of challenges to this work, leading to deep personal introspection and the difficult decision to shut down Tastemakers Africa. While we pivoted during the pandemic and launched The Thread — an incredible success long before people figured out the virtual gathering space — our revenue ground to a halt. That combined with the uncertainty around the return of international travel, and the mental health impact of growing a company for 6 years only for an external event to throw it all for a loop created a gulf that eventually was insurmountable.

Flybridge Enters The Chat

In the months following the Tastemakers Africa announcement, I spent a lot of time thinking about “what’s next” while mourning what was and the loss of what I envisioned would be my future. For anyone who’s started something they believed in, given it your all, and had to end it — you know the latter part can be even more excruciating than the former. One of the people I was in close contact with throughout this process was Jesse Middleton at Flybridge Capital Partners. Flybridge, a NY and Boston-based early-stage VC, was Tastemaker’s largest investor. Jesse was my partner and supporter through the highs of hosting Jack Dorsey in Ghana to the lows of “I don’t think I can figure this out anymore”. Over a few years, Jesse had gotten to know me well and sort of knew my founder “superpowers,” one of which was building community. Community is also the core investment thesis at Flybridge and it turns out that they were looking for someone, sort of like me, to help actualize what that meant for the firm and its ability to invest in and support incredibly ambitious founders.

Reflection and Revelation

When the Head of Community role at Flybridge was first introduced as an option, I had to consider what it would mean for my living my purpose, how I identify myself, and the work I’d been doing at Tastemakers which still feels very necessary and relevant. I also had to ask myself if the skills I’d developed as a founder speaking to a very specific community were translatable to the hundreds of founders working on diverse solutions in the Flybridge portfolio.

As I began to answer these questions (among others), I reflected deeply on my journey as a founder itself. Community really characterizes my journey and is a core value in how I live my life. Within my company, it was the pathway to the early community of curators and experience hosts at Tastemakers, and our first customers and early adopters who all felt a part of something greater by traveling with us. Community was our saving grace in the pandemic, rallying people all over the world through The Thread: Conversations Beyond The Return. On the heels of Ghana’s historic “Year of Return,” we wanted to create a place for the ongoing rebirth of a contemporary, dynamic pan-Africanism and wound up birthing a home for important conversations and a safe, connected, and often joyful space in a moment of global unrest. No one could travel, but we still found ways to gather, connect, and share ourselves in powerful ways.

Community is also how we wound up being a venture-backed company and scaling from a small, bootstrapped group travel company to a tech-enabled experiences marketplace reaching roughly $1M in annual revenue. Raising capital wasn’t easy for the first few years. We ran on fumes with support from Africa-based VC’s, Pipeline Angels, pitch competitions, and accelerators — piecing together a globally operating company without long-range sustainable capital. Precursor Ventures (and the GOAT, Charles Hudson) became the first VC to back us, followed by private investment from the former COO at Sundial Brands and a stint at Booking.com’s accelerator. Finally, we had the kind of dollars that allowed growth and development​​, our first hires, and the legs to really run. We 3x’ed our revenue, launched new cities, and built the first version of our platform within a year and then went on to get a commitment from Erik Blachford, the former CEO of Expedia and a board member at Zillow and Peloton. Soon after we closed our seed round with Flybridge becoming our largest investor.

Tastemakers rings in 2020 with travelers, curators, and traditional leaders of the Gaa tribe in Accra, Ghana

What we initially lacked in capital, we had in su​​pport and an ever expanding network. From early advisors like Jon Gosier, Bahiyah Robinson, and Brian Laung to our early angel investors like Chris Isaacs and Lorine Pendleton. Each person committed and vested in our mission, becoming a critical intersection in our future. Being backed by Precursor led me to meeting Hannah Donovan, now one of my closest friends and co-host on our podcast, “It Just Got Real”. It also led me to cheerleaders and champions like Denisha Kuhlor and Chase Ross who were critical emotional and strategic sup​​port during my 60+ meeting slog of raising a seed round. Even post-raise, I was connected to AllRaise, where a cohort of pre-series A female founders provided authentic opportunities to problem solve, vent, and talk about all of the hard shit of founding a company with a circle I could trust (Shoutout to Isa, Snigdha, Sarah, Tiffany, Dana, Sivana, and Agni). Even meeting Flybridge has its own “community” connection, Erik from Expedia had known Chip Hazard, my first intro to Flybridge, for 20+ years — I met Erik through a cold message on LinkedIn but that’s a story for another post.

With my fellow Precursor Ventures Founders Isa Watson (Squad) and Chris Echevarria (Blackstock & Weber)

Why This Matters

Why am I sharing this winding tale of how I got here? Because Community was integral to my success as a founder even if I didn’t go as far in the journey as I aspired. Becoming a venture-backed founder radically changed the way I did business and not just because we finally had the capital to build in the way I’d envisioned. It connected me to a network of people, tools, and insights that I did not have while bootstrapping. I remember thinking about what I could’ve and would’ve done differently in the early years of my startup had I gotten this support much earlier — especially as Black woman who had no network in tech and really didn’t know anyone who’d taken the journey I embarked on.

This realization — that what happens once you’re funded can be as critical to your success as the funding itself — was a big one. Closing the knowledge gap, making the connections, having resources to expand your ability to solve the inevitable problems that arise at the early stages of building a company all felt like challenges I was uniquely positioned to help founders overcome because they were pain points I had very recently experienced myself.

What if in this moment, while I was still very close to the experience of being a founder, I could take what I learned about the power of Community within my startup and in my entrepreneurial journey and create programs and initiatives that helped founders get connected, leapfrog the learnings, and build wildly successful companies because of it?

Taking a Leap

Joining Flybridge as the Head of Community is an exciting opportunity to use my skills as a community builder and storyteller to help a community I am also a part of. Powering dreams and supercharging entrepreneurs alongside of a team of investors who I have had the great privilege of working with as a founder and now colleague is a unique turn in my career. I’m entering this role with years of experience as an entrepreneur, tons of curiosity about the current crop of builders, and a passion for powering connectivity and ambition.

I’m thrilled at the chance to make Community more than a catch phrase in the venture community and see it flourish at Flybridge as a deeply rooted expression of our ethos and as something that leads to outsized success for the companies we invest in. It is not lost on me that being a Black woman in venture will also offer an expansion into who we see and who sees the firm as a place they can belong, that feels closely tied to my dream of optionality and access for all.

The belief that a Black community that is globally minded and connected to Africa in meaningful ways is our best bet for a transcendent future is and will always be core to my being and my theory for the type of change I’d like to see in this world.

While it’s currently not how I earn my schmonies and work full-time, I’m excited to also announce that I’m a newly appointed Board Member at Birthright Africa, am toying with some ideas in the Web3 space, writing a ton, and continue to explore ways to partner, create, and live in this purpose everyday. The legacy of Tastemakers Africa lives in me and will continue to live in the world. I’m incredibly grateful for every lesson, connection, and experience that was apart of that journey and looking forward to seeing how it continues to show up both in my new role and in ways far outside of me.

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