This is the greatest comeback story in history:

At 12, This Man witnessed his father’s murder.

Later Lost his life savings on 3 failed startups.

Bet everything on one last idea.

Today, his company is worth $3 billion.

This is the story of Tope Awotona, the Nigerian-born tech. entrepreneur, founder of Calendly

and the 3 lessons his journey teaches us about failure, resilience, and success:

At just 12 years old, young Tope witnessed his father’s murder during a carjacking in Lagos.

That moment shattered his world.

But little did he know, this tragedy would ignite a fire within him,
a drive to build something extraordinary.

After his father’s death, Tope moved to America as a teenager.

He studied computer science at the University of Georgia but found himself drawn to sales roles.

Yet, something was missing.

He wanted to create something that mattered.

So, he took the leap into entrepreneurship.

His first venture? An e-commerce site selling projectors.

It failed

His second startup? A garden tools business.

It failed too

His third attempt? A dating website.

That also crashed and burned

Each failure cost him time, money, and confidence.

But each one also taught him something invaluable:

His first failure exposed the importance of supply chain management.

His second failure showed him the value of operational efficiency.

His third failure taught him about market timing and the need for proper funding.

By 2013, Tope was out of money, out of ideas, and out of options.

But he wasn’t out of the fight.

He had one last idea, and he went all in.

Invested his entire life savings, $200,000, into a scheduling tool called Calendly .

Friends thought he was crazy.

Investors called the idea "boring" and "unscalable."

But Tope had discovered a universal pain point: the endless back-and-forth emails just to schedule a single meeting.

He knew this wasn’t just an annoyance, it was a productivity killer.

With no external funding, Tope hired Ukrainian contractors to build the first version of Calendly.

He kept it simple:

A clean interface.

Easy functionality.

One core problem solved perfectly.

And it worked.

Calendly spread like wildfire.

Freelancers loved its simplicity.
Sales teams appreciated its efficiency.
Recruiters shared it with their networks.

By 2020, Calendly was generating over $70 million in annual recurring revenue.

Then, COVID hit.

The world shifted to remote work, and virtual meetings became the norm.

Calendly became essential.

In 2021, investors who once dismissed Tope’s idea poured in $350 million.

Calendly’s valuation skyrocketed to $3 billion.

Today, Tope Awotona is worth over $1 Billion dollars become the few Nigerian-born Entrepreneurs who has crossed the billionaire line

The boy who witnessed tragedy in Lagos had built a tech empire.

But His journey revealed three profound truths about success to Us:

- Rejection is redirection

Every failed startup taught Tope something critical.
The lessons from those failures became the foundation for Calendly’s success.

- Solve real problems

Calendly didn’t chase trends, it solved a pain point Tope experienced firsthand.
The best ideas come from personal frustration.

- Constraints breed creativity

With no funding, Tope focused on simplicity.
That constraint became Calendly’s greatest strength.

Tope Awotona’s story is proof that success isn’t about avoiding failure it’s about learning from it.

So, the next time you face rejection, remember Tope Awotona’’s journey.

Your greatest comeback could be just one idea away.

#TechStories
#calendly
#tope

AI Startup ‘BuilderAI’ has collapsed after it was found to be powered by 700 engineers in India, not AI but AI (Alternative Intelligence)

#talktechafrica

“The $100 million we invested in Iroko TV was a mistake. If I had another opportunity, I would not do it again.”

Jason Njoku shares his terrible, brutal experience running Iroko TV.

Let's read him:

STREAMING IN NIGERIA. DID THE MARKET WIN?

Iroko’s first funding was in August 2011; our mandate was to build a large streaming business in Nigeria.

Tiger Global believed that one of the largest growth areas would be online entertainment, and like most content, the winners would be local content in large domestic markets.

They invested $200 million in Netflix back in 2010 and then invested in IVI in Russia, YY in China, Netmovies in Brazil, and us in Nigeria.

With super-expensive data bundles and inelegant payment options (I remember waiting for Interswitch to enable us to integrate), our market took a while to mature. In most opportunities, you can be too early or too late; only in hindsight can you gauge when the best time to strike would be. iROKOtv was very early when we launched in 2011, but we were fortunate that there was a ready-made international market in the diaspora who were willing to pay and able to overcome any technical hurdles (payment/bandwidth/devices) to enable us to at least generate a sizable income.

We actually waited until 2015 (four years post-launch), building the product, securing a sizable content library, and assembling a team to attempt to take on Nigeria and Africa. Between the revenues we generated and the venture capital we raised ($35 million) over the first ten years, we easily spent $100 million trying to win.

But we weren’t winning; we weren’t really losing either. We were just there, in full survival mode, operating in the toughest conditions possible. Streaming, even domestically, is a scale game.

Africa wasn’t immune to those costs. It’s incredibly expensive across marketing, content, delivery, and product platforms. Our largest, most serious competitors were Showmax, Netflix, Amazon, and Iflix. Collectively, they easily invested $1 billion or more from 2015 to 2023.

During that period, we often had tense board meetings about why iROKOtv wasn’t succeeding; it was challenging to feel that all my hard work and dedication were constantly reduced to “you’re not doing enough”.

We have been, and remain, the most aggressive in trying to distribute content across Nigeria—deploying hundreds of manned kiosks, teams of outbound contact centre agents, creating agency networks, adjusting our product to prioritise Android downloads, and pioneering peer-to-peer file sharing.

At one point, it dawned on me, and I finally shot back in a board meeting: if iROKOtv was losing, could they point to someone who was beating us? In the startup world, that’s usually the outcome of underperformance.

You are simply being out-executed by a better-capitalised or higher-performing startup. In this case, there simply wasn’t anything anyone could point to to establish that.

So my simple assertion was that the market was winning. In 2019, we went out to fundraise; for the first time, we used a bank, Stanbic IBTP, to support that.

We were looking for $10-20 million to keep pushing into and across Africa with our outbound, agency, and kiosk models.

I believed my tales of survival would inspire the (primarily) PE investors that we were going to be the eventual winners in a brutal, long-fought civil streaming war. Instead, they all largely concluded that perhaps there was no market there, that the unit economics were simply not viable at any reasonable scale.

What they were all interested in was the ROK content, TV channels, and distribution business. It was straightforward (fewer than 30 employees), had clear revenue recognition (billion-dollar paid TV platforms – DStv, Multichoice, SKY, etc., with 3-5 year contracts in non-local currencies), and was amassing a sizable IP library funded by the same paid TV platforms. Once we separated out ROK, it was clear where the value lay in Iroko. It represented 80% of revenues and 25% of costs. EBITA margins of 35-40% were achieved without even realising it.

The outcome of that fundraise was the $25 million partial exit (Iroko sold her shares; Mrs Njoku remains a significant shareholder in the studio) to Vivendi/Canal+.

We closed in July 2019.

Before the end of 2019, we had distributed $5 million as a special dividend and were primed to take on the world.

Then COVID-19 happened. Streaming temporarily boomed in the West (our North American business tripled in subscriber growth), while Nigeria closed borders and grappled with peculiar economic principles (devaluations, FX windows, etc.).

The local market in Nigeria simply collapsed. We saw it and stubbornly decided to keep investing and doubling down until we were all tapped out, having burnt through most of the post-exit capital. To save iROKOtv, we considered crowdfunding, an AIM LSE listing (you could raise $10-30 million easily back then) with relatively little revenue but a strong narrative.

In the end, we raised $1.1 million in convertible notes, then recapped the company a year later and paid it back.

In 2023, we finally accepted there was no market for paid premium services and exited Nigeria. We haven’t processed any Naira payments there in almost two years.

As I humbly survey the wreckage of the last 15 years of streaming in Nigeria and Africa, it’s clear our (then $2k GDP per capita) was too small to support even a $5/mo product. It’s clear this wasn’t even a question of capital.

Showmax alone continues to pour tens, if not hundreds, of millions to make it work. But the global giants tapped out last year; their costs (content and marketing) were clearly unsustainably high, and their product needed to be localised to make sense and actually work; it’s just not how platforms sustainably scale.

So I wasn’t surprised when either Amazon or Netflix rolled back their considerable investments in Nigeria. $5/mo is a luxury I doubt even 250k can reliably afford in Nigeria.

You can see the impact of what GOtv and DStv are suffering at the hands of the market. It’s okay that we tried and failed. It’s okay that we accept the limitations in the domestic market we find ourselves in. Did it need $1B+ to figure this out?

Absolutely not. I believe, with my newfound knowledge, that iROKOtv could have reached the same conclusions with $5-10 million versus the $100 million+ we ended up investing.

In hindsight, streaming wasn’t the winning model for Nollywood in Nigeria. Content, channels, and distribution were.

With the economics that business had in 2018, we could have shut down iROKOtv and her $5 million/year in losses and either listed it or just had a fantastically profitable business.

But I was a believer and walked away from millions of dollars in personal liquidity to put it all in to build streaming in Africa.

My lessons were expensive, and that’s why I am so consistent in telling founders not to over-raise.

I am not surprised by the story of Obi from Kobo360; I lobbied him pre-$30m raise not to raise too much capital or later on to seek a merger with his nearest competitor whilst they were engaged in a brutal price war.

The unit economics and payment cycles were brutal, and capital wasn’t going to dramatically change the market dynamics, and it appeared that no one was really going to win that market. It’s only with deep, lived, and expensive experience that I can glance at unit economics coldly and get a feel for whether, with the usual macro turbulence, a startup has a better chance at long-term success.

Nigeria is currently a massive drag on the entire operating business of Multichoice. Their most recent H1 reports indicate.

Reminder that this is the largest pay platform in Africa, which is currently being acquired in a $2.8B deal.

Sola Akintayo is a digital content creator, strategist, and media expert with a passion for helping brands and individuals tell powerful stories that connect and convert. With over a decade of experience across social media marketing, video production, blogging, and brand consulting, Sola has carved a unique niche as one of Nigeria’s leading voices in content creation.

Her journey began with a simple blog in 2013, where she shared everyday lifestyle stories and social media tips. Today, Sola runs a thriving multimedia brand that empowers businesses to grow online using engaging content, smart strategies, and authentic storytelling. From managing viral Instagram campaigns to producing YouTube tutorials that have impacted thousands, she has helped shape the digital presence of startups, fashion labels, NGOs, and thought leaders across Africa.

Sola holds certifications in Digital Marketing, Video Storytelling, and Social Media Strategy. Beyond content creation, she speaks at workshops and conferences, mentoring the next generation of African female creators to embrace their voice and own their space online.

Her content philosophy is simple: "Create with clarity, show up with confidence, and always connect with purpose."

When she’s not creating, you’ll find her curating playlists, exploring Nigerian art galleries, or hosting her weekly Instagram Live sessions where she shares tips on growing a personal brand.

Let’s connect and create magic together.