Since I was 17, I knew I wasn’t cut out for the conventional path. Once I got access to the internet, I became obsessed with finding ways to make money on my own terms.

Today, I’ve decided to let you in on my past failures. I might regret this, but here goes nothing

1) Adcom Africa

Adcom was a micro-influencer marketing agency I ran from 2018 to 2020. The concept was simple: connect students with over 100+ WhatsApp views, teach them the basics of marketing, and let them earn by running ads for brands on their stories.

It worked—at first. We expanded from UNILAG to OAU and even UNILORIN. Students were making money doing the bare minimum, which was exactly what I wanted for them.

But there was a problem: I wasn’t making much profit. 90% of the revenue went to the “reps,” and I couldn’t keep running a business that wasn’t sustaining itself.

On top of that, the brands we worked with complained about low conversion rates. It wasn’t enough to just run ads. The marketing needed to resonate, and the copy just wasn’t hitting.

That realization sparked my deep dive into marketing, branding, and human psychology.

But as the visionary I am, while learning, I jumped into another project—this one’s a bit of a joke in hindsight.

2) Zone6ix

This one barely lasted a week. Seriously. I can’t even remember why we gave up.

It was supposed to be an SME marketplace where we’d drive traffic to their products and take a commission from the profits. Essentially, we wanted to be the next Amazon. Big dreams, right? But reality hit, and we were in way over our heads.

Next failure coming up…

3) 22eleven Solutions

This one stings because it had potential. We were a creative fulfillment agency with the right partners, client inquiries, and everything. I was more confident and knowledgeable in marketing and branding than ever before.

But my biggest mistake? Partnering with four people who didn’t trust each other. Tensions grew, and the underlying issues kept surfacing until I finally had to walk away. I knew success was within reach, but something was still missing.

At that point, I took a break to reflect, but, of course, I didn’t stay idle for long.

4) egbontolu

While egbontolu isn’t a failure, parts of the journey shaped what I’m building now. Plus i still use the name so the story continues but back to the gist

During my break, I noticed personal brands building huge followings by creating simple carousels with content you could find on Google. It was new to me, but I decided to give it a shot. I grew to 1k followers, served 10 clients, and things were going well—until they weren’t.

I ran out of things to say. It felt like everyone was regurgitating the same information, and I couldn’t bring myself to keep doing it. I knew I had more to offer, but talking about just one thing wasn’t fulfilling. So, I stopped.

I lost followers, engagement, clients—it all went down.

So when you say you’re afraid of failure, trust me—I get it. The pain can be overwhelming.

But here’s the thing: I wouldn’t be where I am today, financially or personally, if I hadn’t learned to overcome the sting of failure. Before we dive into how I strengthened my mindset, we need to get one thing straight: failure isn’t the enemy. It’s part of the process.

Now, as I approach my fifth venture, 5th Circle, I’m bringing with me all the lessons from my past experiences. This time, I’m doing things differently.

I’ll document everything publicly—sharing both the good and the bad. It’ll be a behind-the-scenes look at the real struggles and wins of building something from the ground up.

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Two episodes are already live, so check them out and subscribe, or whatever they do on YouTube.

Now, let’s go deeper.

Understanding Failure

Failure hurts because it challenges your sense of competence. It dents the part of you that believes you’ve got it all figured out. But in reality, it’s an ego problem.

You want to believe you have control, and when things don’t go as planned, it hurts.

First, you have to accept that there are countless variables beyond your control, and with every action, failure is always a possibility.

You’re not as competent as you think you are. The knowledge you’re working with has gaps, and that’s why things fall apart.

If you’ve been following me for a while, you know I don’t see failure as something negative.

It’s not a dead end—it’s a signal. It’s like an alarm going off in your neighborhood, alerting you to a problem.

Maybe it’s a fire. Until the fire is put out, that alarm will keep ringing.

Failure is feedback. It’s showing you where things went wrong. And if you can understand the root cause, you’ll stop hearing the alarm.

The Sole Reason You Fail

Failure can happen for a lot of reasons, but at its core, it usually boils down to one thing: clarity gaps.

In all my years of starting businesses and failing, the reasons varied, but there was always one thing in common—I didn’t know what to do next.

I didn’t have the specific knowledge needed to get to the next stage. Whether it was choosing the wrong partners or letting emotions cloud my judgment, I lacked clarity.

You need to see failure for what it really is—gaps in understanding that need to be filled. And some of that knowledge can only come from experience.

Failure is simply feedback. It’s a signal telling you what needs to change if you want to reach your goals. Take, for example, writing a book.

If you start with a blog and no one engages with it, that’s feedback—your writing isn’t compelling enough yet. It’s an opportunity to improve, to close the clarity gap.

Every failure is a chance to get better.

Avoiding the Dip

Now, while it’s important to learn from your failures, there’s a fine line between self-reflection and getting stuck in negativity.

If you only focus on what went wrong, your mind will eventually shut down. Frustration, anxiety, and doubt creep in.

You stop taking action because the thought of failing again becomes unbearable. This is what we call “the dip.”

To avoid this, balance your self-criticism with self-compassion. When you’re reviewing what went wrong, don’t forget to acknowledge what went right.

You need those positive moments, the dopamine hits that come from small victories, to keep you going.

In one of my earlier letters, I talked about the secret to staying motivated. If you haven’t read it yet, go check it out.

For instance, when I built Adcom, it may have failed eventually, but it taught me skills in design and marketing that shaped my entire career.

Those were wins, and I wouldn’t be where I am today without them.

The positives and negatives need to be in balance. If you get stuck in the deep end of failure, you’ll never find the energy to try again

One thing you should realize is that the path to greatness is non-linear. There are ups and downs and those downs are needed so you can go up.

No matter what stage you are in your life you will experience the downs.

Things won’t work out as planned, but if you loose that ego that makes you feel you should have everything in order, understand that failure indicates a gap in clarity that you need to fill with knowledge and re-enforce the parts that are positives, you develop a growth-mindset that is crucial to navigate the up’s and downs of life.

That will be all for today, enjoy the rest of your Saturday.

~ Tolu