Cherae Robinson #WCW: You have to grow in order for your business to grow
Welcome to the All Raise Woman Crush Weekly (#WCW) series, where we highlight genius women who are funding or founding tech companies. Please come back to the All Raise blog weekly to find a new profile of an awe-inspiring female VC or founder.
In honor of Black History Month, the All Raise February #WCWs will celebrate black excellence in entrepreneurship. Our first female founder superstar is Cherae Robinson, the founder of Tastemakers Africa, a peer-to-peer marketplace connecting travelers to unique cultural experiences within Africa and beyond.
Robinson tells us about how she went from working at World Bank to hosting more than 500 travelers across 6 countries with Tastemakers, forming partnerships with Uber, Radisson Blu, and South African Airways along the way.
Q: Tell us about your journey to entrepreneurship, what brought you here?
A: I was working my “dream job,” as Head of Strategic Partnerships for CIMMYT, a World Bank agricultural research organization. For as long as I could remember I wanted to live abroad, travel the world, speak another language, and work in a prestigious, mission-driven organization — I was doing all of it by age 26. I enjoyed what I did, but didn’t necessarily feel that I could bring my “whole self” to work so to speak. I had always had a passion and interest in Africa, that’s what led me to my job in the first place, and fortunately, my work paved the way for me to spend a lot of time on the continent.
I built an incredible network and began to have some of the best moments of my life, but it wasn’t easy, I would spend hours researching, sending emails and Whatsapp messages to friends, all to discover what to do in Johannesburg or Lagos or Nairobi because, at the time, the info just wasn’t readily available or what I was looking for wasn’t marketed for “tourists.’’
I realized that this was an opportunity to really do something that had the kind of impact I was looking for. I first became a “cheerleader,” sharing my escapades on Facebook and becoming the de facto Africa travel expert as the budding Black Travel Movement grew. Soon I decided to take it further, launching Tastemakers Africa as a group travel platform that used microcontent on Instagram to build a community and a following. It quickly became more than a group — it tapped into a movement that struck on the chord of cultural identity and shifting tides among our community.
Q: How did you initially build a team and recruit your first employees?
A: This is actively happening — our team is super small at the moment. Our CTO came through a referral from a contractor who herself was a colleague. Many of our applicants in building this next phase have been customers themselves which is truly exciting. We’re currently hiring employee numbers 4, 5 and 6 and the top candidates have been people who have been following us for years.
Q: How did you get investors on board?
A: Getting investors has been interesting.
I didn’t come into entrepreneurship with any pre-existing connections to capital. I barely knew any entrepreneurs so the entire system was completely new to me. What I did know was that hard work, persistence, and hustle could create possibilities even when things seem out of reach.
One of my investors was someone I wrote down as my “dream investor” on my first pitch deck. I didn’t know how to connect to him but I was able to find him on LinkedIn. I paid for LinkedIn Premium just so I could send him a message. For nearly four years I sent him messages, an update here and there, a hello. I think at one point he shared his email so I was reaching out there as well — no response until one day he did. After the first conversation, he became one of my largest investors sight unseen and has been a huge signaling factor to other investors that have since come along — exactly how I imagined it all those years before.
Q: What is your big vision for Tastemakers?
A: Tastemakers will become the “meeting place” for people of the African diaspora to connect through travel and shared experiences offline and on. I see us creating a truly community-powered environment that is the center point of a movement towards a global black identity.
The evidence of this is already showing. Just this past December we had nearly 1,000 customers from our community in Accra, Ghana for “The Year of Return,” a commemoration of 400 years since the first documented ship carrying enslaved Africans arrived in America, Jamestown, Virginia to be exact. As we began to think about what we should do as a company for New Year’s Eve, a night which was already loaded with celebrity parties and concerts across the city, we pulled back to think through what our customers really need and who we wanted to be for them as a brand and as a company.
For most of our customers, coming to Ghana, especially in 2019, was a lifelong dream fulfilled with spiritual resonance. We decided to invest in that and gathered our curators and friends in the Accra community to make a memorable, spiritual “Renewal” happen on the shores of the Atlantic ocean. Chef Binta, our most popular curator, did a Fulani-style feast of epic proportions, Nii Marma, the curator for our Jamestown experiences, gathered Ga priests and priestesses to lead the group in traditional spiritual rituals and prayers at the stroke of midnight, the leader of our drumming and dance experiences led lessons on the beach after fireworks went off at midnight and Nanan, the owner of Bliss Yoga, a popular studio in Accra, led movement meditation and affirmations to kick the night off. Nearly 200 people joined us on the beach in an experience that tapped into the needs of our community to create connections and value with one another. It was by far one of the greatest experiences we’ve done and I’m looking forward, as we launch new cities and grow in the next 12 months, to tapping into our unique understanding of the needs and desires of our community to share the stories and experiences that only we can.
Q: Why do you think it’s the right place and the right time to invest in emerging markets?
A: I think online platforms and the creative economy are providing a signal of the future in emerging markets that’s never happened before.
The sharing economy combined with the democracy of visual storytelling (made possible with apps like Instagram) is allowing young people especially to “own” the narrative of their own lives and therefore their cities and countries right with them.
It’s hard to think that Africa is a “backward” market when people like Trevor Stuurman are using Instagram to share Vogue magazine-level scenes of Johannesburg to nearly half a million followers daily. Being able to use Uber to get around or Tastemakers Africa to book a tour enables conversations and shared experiences that provide deeper interactions in markets where previously the larger media narrative and business assessments said: “Be afraid.” These two drivers are ahead of traditional business sectors — for those that lean into these signals, there is an opportunity to invest in emerging markets because the human capacity is at an all-time high, there is a readiness and trend in leapfrogging and innovation, and the traditional places for investment are showing instability that is in opposition to growth.
Q: What’s been one milestone you’ve hit where you were sure you were onto something big?
A: In January 2019, right after we’d fully pivoted from being essentially a tour company with a lot of online swag to a full-on technology platform bringing the sharing economy to African creatives and freelance tour guides, we saw nearly $100K in revenue in a 30-day period. From that point on we never had one week without a booking.
Q: What are some of the biggest challenges you’ve faced while building the company?
A: Marketplaces are always a chicken and egg game which makes them incredibly hard businesses to build but also incredibly big if you get them right. For us, this was magnified by a few things. We had a big lag from the time we actually onboarded our initial supply and the time we actually had a product we could market to customers, so we ran the risk of losing out on that supply and the work and investment in bringing it onboard. We went after non-traditional suppliers and relied largely on informal networks to do so. This was great for really being able to differentiate our offering and truly build a community that was on-brand, but it also meant that standards of what a “Tastemakers Experience” would have to be translated again and again to each individual experience provider.
Finally, the initial fear many investors had around the market being big enough or the African market, in general, meant that instead of having a solid amount of runway to build and experiment with, we were always building to “tranche” so to speak. Despite these challenges, we use all of this as a learning and testing ground and did a lot with a little along the way. We’re in a much better position post-raise and with investors like Erik Blachford who ran Expedia for decades, Charles Hudson at Precursor Ventures who’s seen literally hundreds of marketplaces, and Jesse Middleton at Flybridge who came from WeWork and gets how the community can be a competitive advantage. Each of these investors brings much more to the table than cash itself and are partners into leaning into the things we got right while providing insights and access to the things and people we need as we grow to this next stage.
Q: Why do you think the timing is right for Tastemakers?
A: Tastemakers is the intersection of a few interconnected movements:
Black Identity in the face of our current political climate is becoming something people are not only more confident in but seeing as a badge of pride and honor.
Naturally, that means the exploration of what that means from a heritage perspective is becoming a core part of that, whether it’s taking DNA tests like African Ancestry, traveling to Africa, or celebrating more direct family lineages.
The Africa narrative is turning the corner on a seismic perspective shift.
Its economies are being counted as some of the fastest-growing in the world, its music is taking over the airwaves of the biggest cities in the world, and its entrepreneurs are using mobile phones and the unique challenges presented by their environments to create leapfrog moments and innovation.
Just this past November, Tastemakers hosted Jack Dorsey in Ghana for a day. He and most of Twitter’s leadership did as many experiences as we could pack into what was a short trip from going to the slave castles in Cape Coast to a chef-led dinner to partying the night away at a private members club. Five years ago no big tech CEO was doing this. Jack went on to meet more than 150 entrepreneurs across four countries on the continent and is even moving there for a stint this May. Tastemakers has been a part of this shift at the ground level and has built the brand reputation, infrastructure, and product to really “own” the space not only for the American consumer with Africa on the brain but also for the African consumer who is looking to tap into an aspirational view of the continent that used to be reserved for Europe or Dubai.
The sharing economy has been mainstreamed and we’re in a second phase of that which goes beyond the transaction.
Tastemakers is well-positioned to go from “sharing” as a business arrangement in the absence of meaningful connections to being a third space that layers a dynamic community on top of the value of the buyer-seller peer exchange. This is where things get interesting — a feedback loop of user-generated content, community-organized meetups, and other signals that make people feel more like “members” than “users” is where the magic is. You may tip your Uber, or rate your AirBnB host, but you’re likely adding your Tastemakers curator to your WhatsApp group — or even getting the numbers of the other people who did the experience with you. Our community is built on shared aspirations, values, and beliefs no matter which side of the marketplace you sit on. These dual feedback loops are our engine for growth.
Q: What other startups led by black founders are you a fan of (that we should look out for)?
A:
The Folklore (fashion startup disrupting supply chain to bring African designers to the world.
Wiggle Room (last-minute childcare from your trusted community)
Hurston House (like The Wing but for black women)
Mercaris (Agricultural Commodity Trading Platform)
The Difference (AI Powered Therapy)
Q: What is your best advice for other founders trying to navigate the roller coaster of startups?
A: Accept that it’s a roller coaster and buckle up. Lean into the ride and most importantly recognize that you’re going to have to grow in order for your business to flourish.
The best thing I’ve done is really think about how to be a better learner. In the early days, it’s all about your “idea” but once you’ve gotten to a space where you’re seeing some revenue and making decisions on the future, you’ve really got to be able to constantly chart the next steps with more than a feeling.
I’m launching a podcast with another founder, Hannah Donovan of Trash, and on the last episode we recorded, we were talking about how purpose and focus can ground you on this ride. It’s the moment when you know what you’re building, why you’re building it, and who you’re building it for that centers you and braces you for anything that comes your way. The sooner you arrive at that clarity the better.
