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A Peek Inside Her Agenda: Cherae Robinson

Founder & CEO, Tastemakers Africa

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Sep. 16 2019, Published 3:00 a.m. ET

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A Peek Inside Her Agenda: Cherae Robinson
“I’m my only gatekeeper.”Quotation marks
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From struggling with paying her rent to becoming one of the few Black women entrepreneurs that have raised over $1 million in venture funding, Cherae Robinson is proof that with hard work, persistence, and a product that consumers love, dreams can come true.

Cherae Robinson is the founder and CEO of Tastemakers Africa, a peer-to-peer tour and activities marketplace committed to changing how the world assigns value to people, places, and experiences. Prior to launching her company, Cheraé bridged the gap between science and people within large international organizations like CIMMYT, CARE, World Bank, and the US Centers for Disease Control and Prevention.

Despite what social media depicts, the entrepreneur life isn’t as glamorous as it seems.

Often times, to be a successful entrepreneur, you have to make uncomfortable sacrifices, and be willing to keep pushing forward even when funds are low and days are dreadfully long.

In a recent chat, Cherae shares how she launched her company with a single Facebook post and no website, the sacrifices she made after pursuing her startup full-time, and the biggest lesson she learned about pitching to investors.

Her Agenda: What was your inspiration behind Tastemakers Africa?

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Cherae Robinson: While I was at the World Bank, I was spending a lot of time in Africa, specifically in Nigeria, and in Kenya. I started feeling like my co-workers were doing these sorts of obvious things through TripAdvisor experiences, but they were largely older white men. Me, as a young, Black woman, I felt like I couldn’t find experiences that resonated with me and who I was. 

As I later started to discover these types of experiences, my friends back at home were like, ‘what Africa is that?.’ That was constantly the question because friends would see me meeting fashion designers and filmmakers, partying, and going to nice restaurants. Everything I was sharing on Facebook, or Instagram began to show the other side of Africa that in 2011 and 2012, people hadn’t seen and people weren’t talking about – especially in the U.S. From there, I started to think that maybe there was an opportunity to build something that made it easy for people to connect to a more modern and authentic view of traveling to Africa. 

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Shortly after in 2014, I decided to take a group of my friends to Ghana, and they loved it. We created a hashtag, and people started reposting the photos we were posting. It became an interesting moment where I realized that people did indeed want to see more of this continent, but didn’t have an opportunity or an access point. Also, people were now paying me money for these opportunities.

"I started to think that maybe there was an opportunity to build something that made it easy for people to connect to a more modern and authentic view of traveling to Africa." -Cherae Robinson Tastemakers Africa via Her Agenda
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Her Agenda: How did you get people to pay to travel with you to Ghana?

Cherae Robinson: I created a PayPal link and shared it on Facebook. My post pretty much said, ‘You guys are always asking me what to do in Africa. I’m going to take ten of y’all with me to Ghana, and we’re going to have a next-level experience in Africa.’ 

Within two weeks, I sold out. It wasn’t just my friends that purchased it, but it was their friends, and then their friends’ friends. At that time, I didn’t have a website – I just had a Facebook post and people registered that way for the trip. By the next year, I knew it was time to pursue the idea. I built a real website and later won a startup competition in Nigeria [run by] She Leads Africa. In 2015, I built my WordPress site and the only thing you could do on it was buy a trip and read some blog posts that I was writing myself about things to do. 

After I built the site, I had tourism boards reaching out, and we tapped into the moment and started building this group travel brand. Shortly after, we felt like we weren’t doing enough so we changed the business completely and pivoted to being a marketplace in November of last year.

Her Agenda: When did you quit your 9-5 to start working on Tastemasters full-time?

Cherae Robinson: When I first launched Tastemasters I was working a 9-5 but within six months, I quit my job. Around that time, I moved to New York and was working for Alicia Keys’ nonprofit. I knew it wasn’t a space where I was supposed to be so I lasted for about six weeks. Afterward, I went and worked for a startup for a few months. Then, I traveled to Nigeria to compete in She Leads Africa’s pitch competition. While on my flight, I prayed and told God that if I were to win first place, I wouldn’t turn back. Once I got that stamp of approval by winning that startup competition, it was a sign for me.

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While on my flight, I prayed and told God that if I were to win first place, I wouldn’t turn back. Once I got that stamp of approval by winning that startup competition, it was a sign for me.

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Her Agenda: Can you share more on your experience after going full-time with Tastemakers? 

Cherae Robinson: I know often entrepreneurship sounds super glamorous, but it’s honestly usually not. The unglamorous part of my story is that when I first decided to go full time, I actually closed out my entire retirement of $40,000 and lived on that for about 6 months. From there, I raised a little bit of capital, and while I was in a relationship, my partner covered the bills and did that for a while.

We eventually broke up and I had to figure out what to do. Crazy story, I literally wrote my landlord and told him that I couldn’t pay him. My landlord ended up Googling me and looking me up on LinkedIn, and saw the press about me. He wrote me back and told me that he was a venture capital lawyer and asked if I was talking to any investors. After sharing that I was, he said I could finish closing out my investment and pay him when I was done. After I paid my landlord, I moved back home. I moved back into my high school bedroom along with my son. I didn’t want to have any extra expenses that I would’ve had by having my own apartment. I hadn’t stayed at home since I was 14, but I knew it was a sacrifice I needed to make, even at age 35.

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I literally wrote my landlord and told him that I couldn’t pay him. My landlord ended up Googling me and looking me up on LinkedIn, and saw the press about me. He wrote me back and told me that he was a venture capital lawyer and asked if I was talking to any investors. After sharing that I was, he said I could finish closing out my investment and pay him when I was done.

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"I moved back into my high school bedroom along with my son. I didn’t want to have any extra expenses." -Cherae Robinson
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Her Agenda: During that time, what made you decide to go through the process of raising money? 

Cherae Robinson: I knew that to grab any meaningful part of the market, we needed to grow fast. The only way to grow in that way was to get backed. If you want to be able to go from having infrastructure and operations in multiple cities, and being able to employ the best talent, all of that requires capital that as a marketplace, you’re not going to have from a profit perspective in the beginning. Marketplaces, as a business model, offer some of the biggest upsides if you get it right, but it’s slow-growing business because all your revenue is coming off of commission. 

I knew in order to grow fast and to take advantage of the moment, I needed to be able to have investors that not only provided financial backing, but that provided strategic insights and relationships that would allow us to scale globally and quickly. 

Her Agenda: What pitching mistakes did you make in the beginning?

Cherae Robinson: For a while, the mistake I made over and over again was being a storyteller, and not pitching in a way that translated the value of my company and the financial upside. I was good at describing the problem and sharing my passion for what we were building, but in the beginning, I just didn’t understand the key thing that investors were looking for. I knew that they cared about the story, but they also wanted to know how it was going to be a billion-dollar business.

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" the mistake I made over and over again was being a storyteller, and not pitching in a way that translated the value of my company and the financial upside." -Cherae Robinson via Her Agenda

Her Agenda: Now that you’re a full-time entrepreneur and scaling your business, what is a quote or motto that keeps you motivated? 

Cherae Robinson: I’m my only gatekeeper.

Building a business, especially one that is very much public-facing and to some degree requires social buy-in, it can be very easy to get distracted or discouraged. 

The reality is, whenever I’ve missed out on an opportunity it has largely been because of my own actions or inactions. There’s no way someone else can take an opportunity for me, so that’s why it motivates me to say, ‘I am my own gatekeeper.’ It keeps the emphasis on progress on myself. It reminds me that my goal is not to be worried about everybody else, but to be holding myself accountable, to be moving with integrity, and to be constantly growing as an individual. If I can’t do that, as a Founder and CEO, my company won’t go anywhere. 

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