The Biggest Battles I Face As an African Technology Entrepreneur are in The Mirror

Wiza Jalakasi
7 min readSep 2, 2016


Sometimes I’m the biggest impediment to my own progress

Photo credit: Kalle K (

Three weeks ago, I wrote about my experiences as a tech entrepreneur in Africa. I had told my friends that I’d write a second post if I got 15+ recommends.

I didn’t really expect it to be “good enough” to go viral, but that article now has over 490 recommends and has been republished on Startup Grind. The republished article has picked up 50+ more recommends and is growing by the day. I guess I’m not doing too bad.

And yet somehow, I still d̶i̶d̶n̶’̶t̶ don’t feel confident about publishing this post. My mind has a funny way of playing tricks on me, often leading me to overestimate my ability in certain areas and underestimate them in others.

#1: Confidence

Writing this brought back a familiar feeling. I felt the same once before in 2015 when I was about to pitch Djuaji to an audience of over a hundred people at Pivot East 2015 (East Africa’s Premier Mobile Startups Pitching Competition). It was a two-minute pitch, but I’d spent the last 2 weeks revising and practicing it with the Pivot East Team and my co-founder.

Over the last 6 years, I have become a pro at pitching. You’d be surprised how fast you can learn how to do something when you really need the money .

When it’s do or die, and dying is not an option, do will always have to happen. It’s that simple.

By the time I was walking up to the stage, the content was etched on my mind. I knew it inside out and could recall any information about the company on demand.

<rant>I was going to write a Redis vs MySQL joke on this line but I can’t find one that won’t be too nerdy.</rant>

Pitching time came. Mic was on, presentation remote in hand, I glanced at the two monitors in front of me and the timers started counting down.

For a moment, I was frozen, paralysed by an irrational fear that the pitch wouldn’t be good enough, that I would drop the ball and the whole world would see through the ruse and find out that I’m just an ordinary guy with a computer and some ideas.

I didn’t feel like the guys you see in Silicon Valley (not the TV show), at the very bleeding-edge of innovation, able to confidently defend any decision they’ve made in their products or companies.

Was it Imposter Syndrome? Or were we really just lying to ourselves? Here we were with some elegant pitch decks, a gorgeous front-facing site and dirty, hacked-together PHP prototype of the product and between us, about less than a year of real market research experience.

I wondered if even I would believe my own pitch.

It didn’t matter. Mercy stood beside me and delivered the intro and we were already 20 seconds into the pitch, I didn’t have anymore time to think — I just went into autopilot and pitched my ass off.

Photo credit: Pivot East Media Team

It was beautiful. The audience was engaged, we had captured their attention. We ran through the slides like clockwork and completed the pitch with seconds to spare.


They were actually impressed! I was surprised, but at the same time elated because this was validation. Before I could even begin to relax and pat myself on the back, the questions came. We were standing in front of about 5 expert judges who started firing hard.

Again for a moment, I wondered whether this was it. And yet again, we handled their questions with ease.

As we walked off the stage, it hit me. Maybe we’re just as good, if not better than those Valley founders we adored so much.

<rant>I just wonder why I didn’t see it then. Was it because there weren’t enough of our own examples to look up to? Where is our Zuckerburg, Africa?

I opened my email a few days ago to read the Index Newsletter. RackSpace just got acquired for an amount equivalent to my country’s GDP. One of our old competitors just raised a million dollars which is great, but I’m just not sure whether that’s supposed to inspire me or discourage me.</rant>

A few hours elapsed. It was a pitching competition, so a winner needed to be declared. From the reactions on social media, I honestly thought we’d won our category.

I tensely walked up to the stage hoping it was true. A victory here would be massive for our exposure, considering that we were looking for strategic partnerships and not money like most other startups pitching. Erik Hersman stood with the results in hand, the winner of Pivot East 2015 Enterprise Category was… DumaWorks!

I felt shock for a moment, then disappointment. I stood there visibly defeated as Allan Matata walked up to claim the prize that was seconds away from our hands.

Photo credit: Pivot East Media Team

We had lost, and losing sucks.

DumaWorks did deserve the win though. They had an excellent product, a fantastic team and plenty of traction. On top of that Allan gave an incredible pitch, and ours wasn’t too bad, but theirs was better.

Competition in the tech startup scene is intense — there’s no other way to describe it.

The biggest lesson I learned that day was about confidence. That no matter what you’re pitching, no matter who you’re pitching to, you’re likely to feel some degree of self-doubt. Never let it win.

#2: Hubris

Should have Googled this sooner.

One question that keeps me up at night somedays is how the hell I thought we could build a market research startup without a founder who has at least several years of industry experience?

I think I greatly overestimated my ability in that scenario.

The funny thing about knowledge is that you don’t know what you don’t know until you actually know it.

My philosophy to startup building these days is to always approach a situation with a rookie mindset. There is something new to be learned about everything, everyday.

This really dawned on me in a meeting with a big market research firm that was considering using our services. They emailed us a really complicated excel sheet with their requirements and I couldn’t make sense of it. I mean how hard can it be to just build a survey and deploy? I was wrong.

There’s so much more that goes into market research than just data collection and analysis. If I’d known this months before we started building, we’d have built a totally different product and approached the market in a completely different way.

#3: Consistency

Some days I wake up feeling like the best technology entrepreneur on the continent, other days I just want to sit down, eat bacon and play Fallout 4.

At the end of the day, I have an obligation to my customers and my team to deliver on what they need for the company to be successful. Being a startup founder is really exciting, when you’re travelling all over the continent, pitching, raising money, watching metric graphs grow and just generally winning like a boss.

Some days, you’re just sitting down reading through customer support emails dealing with irate users who don’t understand that the thing is broken and it’s not really your fault.

Dude, I know. I’m working on it.

Other days, you’re with a pen and paper and a scientific calculator still trying to figure out how to record certain expenses, so that you can send your investors the financial position update that you promised them yesterday.

Most days in a startup are pretty underwhelming, but all of these days are just as important. Wrapping my head around this has been a big challenge, but I’m getting the hang of it now.

Trying to do these more frequently, aiming for a new post every two weeks but it’s always an emotional journey having to revisit these experiences.

Some days were good days, but most days were hard days.

I appreciate all the fantastic feedback on my last post, and I’ve learned so much from all of you.

Till next time!

(A note of thanks to my new friend Opeoluwa Oyewole who has generously donated some of her time to helping me edit this post. If the grammar on this is on point, you have her to thank.)

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Questions or comments are more than welcome and if you want to have a chat, I’m available on email (yes it works), Facebook, Twitter and Instagram and Snapchat. I do my best to respond to everyone.



Wiza Jalakasi

🇲🇼 Africa fintech, travel, love, culture, life / 🎮 Gamer / Merchant Payments Executive / 📩 social@wiza.gq