31 Dec 2021


The last time I wrote an end of the year review was 3 years ago. I got lazy, bored and disconnected. That feels like a long time ago and missing this year increasingly makes it difficult to connect the dots as the years go by. These writings are more of a personal journal to look back to and see how far I have come. Interestingly, I see a lot of parallels between 2018 and 2021.

I would have to start in 2020. We can all agree 2020 was a crazy year. For me, it took more turns than anticipated. Towards the beginning of Q2, it was obvious my time at Reliance needed to end. I dropped a 3 months notice and resigned end of July. I had no new job waiting and no plans, just faith that I will figure it out.

Relocating wasn’t much of an option. Covid made sure of that. I also wasn’t interested in hopping on the next job. I needed time to just be still. One evening, I was having a conversation with a friend I had launched a startup with in the past and one of my experiments came up. That conversation became Engage.

I have always been passionate about customer messaging. This is obvious in the projects I have worked on in the past and cofounding Callbase, a cloud call centre solution. If there is something I want to spend the next decade working on, then it is customer messaging. And at that moment it clicked. With my friend’s help, I started raising for Engage shortly after and through the end of Q3, it was trying to convince potential investors that it’s worth putting funds to.

Engage is the coming together of an idea I had tried to solve in different forms and separate experiments. The goal is an answer to the question, “how do I effectively use my customer data to send the right message to the customer that needs it at the right time?”. Here are just a few examples of what that translates to:

  • Automate payment reminders when a Stripe/Paystack/Flutterwave payment or subscription fails
  • Create an onboarding flow that automatically sends customers messages based on what they have done or not
  • Track inactive users and automatically send them a nudge when they have been inactive for a period of time
  • Send abandoned cart reminder emails

This was a challenge I had noticed in my everyday interaction with startups, businesses and organisations. At that time, a bank account I created out of curiosity and never used kept sending me SMS that I quanlify for a loan. The day I decided to try it, I dialled the USSD code and the response was: “Sorry, you do not have a salary account with us”. Why tell me to get the loan in the first place?!

Raising money was a crazy new experience. Some days, I was averaging 2 to 3 investor calls that were 45 minutes minimum.

“What’s your MOAT?”
“Why do you think you can build for a global market from here?”
“Why you?”

I started feeling drained. I couldn’t even build. I would finish the day mentally exhausted, open my code editor, stare at the screen for a bit, manage to move a few things around then close my laptop. All I was getting were nos, maybes and let’s talk again.

By December, the Yes started coming in – friends, VP, Voltron, DAN, and many more. Some investors even introduced me to others. Ridwan only saw a tweet and sent me a message that he is in. When I asked him when to schedule a call to demo the product to him, he literally told me not to worry about a demo.

By the first week, February 2021, I figured I had raised enough to get things on the roll. I wanted work to start in full throttle. The distraction of raising was too overwhelming. I shut out every pending conversation that was yet to translate to a yes. Big mistake. Work started in full gear and Engage became my 2021.

Yes. Engage was literally my 2021. I had done 2 startups in the past as a technical cofounder but even that didn’t prepare me for the chaos of being a founder, a solo one at that. For the first time I could remember, I started struggling with sleep. You know it’s real if in a year I don’t work on any side project.

I tried to bring in a growth cofounder earlier but he had other priorities and we didn’t work. The 3 months felt like a waste and I was devastated. I then decided I wasn’t even going to sweat the “get a cofounder” thing unless I get the right person.

On the evening of the first Friday of August, I felt a sudden chill, threw myself on a couch in the living room and decided to nap. A few minutes later, I started shivering uncontrollably. J gave me some drugs and I managed to pull through the night. I woke up the next morning feeling a bit ok but very tired. I attributed it to stress and felt I needed to get more rest. I went to the hospital for tests after church on Sunday but all the usual suspects, viral infection, Malaria and co, turned out negative.

I was useless for the best part of that week. I was waking up extremely tired. I’d come on Slack, see what’s going on, give some directions and that was it. I couldn’t set up or join meetings, write any code or do any serious work. It was really humbling seeing myself zapped out. I spent days just sleeping and watching Netflix. I was completely physically drained.

We were supposed to travel to see my folks the next weekend. Two nights before the planned day, J came into the room asking if I smell what was burning.

“Hmmm….something is burning? I can’t smell it”

Then it dawned on me, I might be Covid positive.

I buzzed Francis immediately and asked him how to get a test at their lab. The next morning, I took the test, and 24 hours later, my guess was right. I was positive.

As I read the report around 3 am that night, many things were racing through my mind. I have a 7 months pregnant wife. I have a 4-year-old. And yes, J tested positive. Even if J turned out fine, what about the pregnancy?

The following days were long and nights were cold. Psalms 91 was our comfort. We welcomed Oluwadarasimi (God is good to me) to the family at the end of October – mum and son, perfectly fine.

I was reviewing Engage’s numbers when drafting update last night. They are not where I want us to be but things are starting to align. It may take some turns but we will figure it out. There is where I’d rather be.

Here is to a better 2022.


Looking for a simple marketing automation tool to automate your customer onboarding, retention and lifecycle emails? Check out Engage and signup for free.


My name is Opeyemi Obembe. I build things for web and mobile and write about my experiments. Follow me on Twitter—@kehers.


Next post: [Building Engage] #2. Rethinking our pricing model