Meet the Black female founder that raised over $1 Million to make African tourism great again

We know black women are starting businesses at an all-time high. In an article, earlier this year Entrepreneur magazine stated: “Black women are starting businesses at a faster rate than any other demographic.” 

This should be a cause to celebrate and toast it up, BUT hold on don’t get your glasses out yet.

Did you know, according to reports from Digital Undivided, in 2018 there were only a little over 35 Black women in the Million Dollar Club.

The $1MM Club includes Black women who’ve raised over $1MM in venture funding. There are still several seats open in this club, but sadly not many Black women get to secure their seats.

Cherae Robinson is one of the few Black women with a seat at the table in the $1MM Club and it’s such a major accomplishment.

These days, she’s busy sharing African travel experiences to disrupt what the world thinks about Africa with her travel company. Tastemakers Africa is a digital platform and peer-to-peer marketplace that curates prices, tours, and lists African travel and cultural experiences, helping it’s users discover unique and exciting things to do on the continent.  

It hasn’t been all wins and roses for Cherae though.

Before raising $1 million in venture capital she was fired from three jobs as a single mom and as a non-technical founder was scammed out of a lot of the money she raised by design and software development agencies that took her money and gave her nothing in return.

I know! What a comeback, Right?

Let’s look into how Cherae stayed the course, believed in her vision and continued her mission with resiliency EVEN after having to move into her childhood bedroom with her son to build her business and losing most of the capital she raised.

Source – Mac-Jordan Degadjor’s Blog

I read an article on Medium where you said you quit your dream job to start Tastemakers Africa. Can you tell us about that? How did you know it was time to make that transition and take the leap to leave your full-time job?

I was a Biologist with a focus on international development for about a decade, I focused on being at the intersection between science of humanitarian work, and translating that into something both people and corporations could understand.  I really loved my job. I basically had done everything I had always wanted to do by the age of 26 and it was so amazing!

But that being said, I felt like I was in a system that didn’t let me be who I was which was 100% exhausting. One person told me that in order to survive in these systems that I had to be a really bad imposition of an old white dude instead of being myself, and so that was a challenge I couldn’t commit to.

I was doing meaningful work in Africa and I was also experiencing parts of Africa that got a lot less mainstream media attention and so over time, I found that when I shared on my experiences in Africa on personal social media it resonated with a lot of people. 

Empowered by the storytelling and the opportunity to share and showcase Africa through a new lens, I started thinking about what it would look like if I created something that let people see Africa the way I was seeing it. This sort of modern, contemporary, aspirational version of the continent and to do it in a way that made people want to travel to Africa.

It became impossible to focus on work, after coming back from Africa, so I became unemployable. I got to the point where I took a job to come to New York City, working with a celebrity foundation and within six weeks my boss said, “You don’t wanna be here” and I responded, “You know what, you’re right”. I essentially got fired from that job. I couldn’t even get unemployment, so I got a job at a start-up because I wanted to learn what it was all about. And a year to the day that I got fired from my celebrity non-profit job, I was let go from my startup, because they got VC-funded and were re-shuffling. My next thoughts were, “I don’t think I’m supposed to be working. I don’t think that this is what I’m supposed to be doing”. 

So two months after getting fired from that start-up job, I won a competition in Nigeria called She Leads Africa and I remember praying on the plane and I was like, “If I win first place in this, I’m never giving up on this idea”. 

I won first place and I never looked back.

How did you figure out your branding, target audience, and product-market fit for your business?

To be honest,  I wasn’t even that organized. I built Tastemakers originally for me, so I built what I liked. I didn’t know anything about marketing because I’m a biologist by trade, so I basically just followed my instincts at the time. A good friend of mine was a photographer in Johannesburg working in the agency world, so she had all these super dope images. Those were the images I used for branding and marketing in the beginning.

Early on, it was just leaning on my own instinct and going from there. I didn’t do market research or testing nor did I bring in professional people because I couldn’t afford it. I literally thought, “This is what I would want to see and this is what I would buy.” It resonated with people.  To this day, marketing is actually the hardest thing for me to outsource because I have so many opinions about it and I’m so close to it.

Source – Cheraé Robinson
@sasyrae

How did you navigate through the start-up world as a non-technical founder and build out your team? Tell us about how you handled hiring technologists as a former biologist.

Well, I mostly failed at it and wasted a lot of money.

With one of the first engineers I hired, I literally flew to Kenya to deliver him a brand new Mac Pro because he said he needed it to do his work. Then he just disappeared and never got online.  I also spent thousands on the second team of developers and outsourced development to a team in Vietnam which as another waste of money. We just weren’t prepared. 

Then I went through an outsourcing firm, in Africa, and just underestimated how junior the hires would be. They were charging us at senior developer rates, so I probably lost thousands of dollars with that. Most of my first investment capital literally went to these mistakes, but I don’t look at it as a total loss because I just learned a lot about product development through those failures. 

Although there were a lot of mistakes,  to be honest, I’m super fortunate. A lot of people would have lost those funds and not been able to raise money again, but for me the mistakes just fueled me. In tandem with losses on the tech side, I just doubled down on our group trips business, even though it wasn’t the part of the business I wanted to scale or grow I didn’t know what part of the business was going be scalable at that point. So in some ways, those failures allowed me the time to learn a lot more about the market and what people needed both on experience side and also on the travel side.

I’m thankful for these failures even though they cost me a lot of money!

You are one of the very few black women in the $1MM club and considering that the startup and VC spaces are lonely and dominated by white males, let’s talk about how you navigated these white male spaces. How did you feel navigating these spaces?

So I think there were a few things that helped.

 First, I found my safe space.  I was definitely the person trying to find the one black person that was in the room that I could connect with. Well, every black person is not here for you!  I was really fortunate to have another founder by the name of B Arthur who I feel like is a “G” at navigating these spaces.

Secondly, I think what really was key for me was taking a step back.  I had to take a step back and realize that I was actually already in a privileged position, so, I thought about the fact that there are so many black founders that don’t even have an invite to be in these spaces.

I really lean into the fact that I’m in a privileged space even being able to have these conversations, knowing the VCs, getting the invite and already receiving funding.

Third, it’s about transforming the narrative and understanding that I have to open the door for the next group of people so they don’t feel like this.

Shifting my perspective helped me navigate these spaces, but I also moved into a space of acceptance. It’s fine that everyone is not going to be an advocate for your business and you don’t actually don’t need everyone to be and that’s okay.

What you’re doing is incredible and revolutionary! How do you manage imposter syndrome and burnout when you’re operating at such high levels and doing extraordinary things?

I think that part of it has been really leaning into aligning myself with other women that have done what I’ve done.

One of the challenges I felt early on was not being surrounded by people on the same journey as I was on. My friends have been amazing, but my friends have not done what I’ve done in many ways and so, I struggled for the longest, feeling super isolated and realizing that the only people that get this are people who’ve done it. I really needed to align myself more with people who’ve done it, so I don’t feel alone and so that has been really helpful in level setting my own expectations for myself. 

Female founders have been really, really helpful, particularly in the past six months in helping me navigate. As far as imposter syndrome, I’ve also been told straight up that it just doesn’t go away.

 I’ve definitely adopted much more introverted traits, which I think is a positive because it’s forced me to really compete against myself.  I’ve decided that I am my own gatekeeper and really leaning into the fact that I am my own competition, has allowed me to put blinders on when I’m feeling imposter syndrome. 

Now I’ve transformed my thought process to  “Oh my God, I’m not as good as this person I met, and really transform that to… I am different from them and that’s why I’m gonna win”. That’s been something that I’ve adopted that’s really important for people to know.

How do you manage your self-care as a founder and mom?

Giving myself grace is something that I’ve started embracing. I went through a crazy, horrible break up this year and that forced me to be gentle with myself and learn how to do that.

My number one piece of self-care advice is to stop comparing yourself to other people and give yourself grace. Sometimes that means realizing that I’m doing too much, other times it means knowing how to do more.

My self-care looks like going for a run sometimes, but I’m also really into products and I calender my self-care. So, Sundays is a deep cleanse, day, that’s when I’m doing my deep condition or Wednesdays I get my nails done and that’s on my calendar. When my team sees this they already know it’s deep clean Sunday and don’t mess with Cherae. Find some things that work for you and test some things out and really be committed to doing them. At the same time, don’t be trying to be the self-care poster child because it’s cute. That only leads to beating yourself up in a different way.

feature photo credit: Source – Yahoo Lifestyle

Written by Jeneba Wint

Jeneba Wint is a creative technologist with over six years of experience leading SAAS digital product development projects. She enjoys speaking on product experience and development, digital transformation and the future of work and career development for black technologists.  As a data-driven product strategist and user experience storyteller, she is focused on digital transformation and digital product management within startups to mid-sized enterprise corporations. Her secret sauce is product design and development using customer behavior, product metrics, content, and interaction design to drive product engagement, adoption and optimization.  A good product experience makes her happier than a kid at a candy store!