Recovering Entrepreneur?

Recovering Entrepreneur?
Photo by Alora Griffiths on Unsplash

I've previously described myself as a ‘recovering entrepreneur’, but I haven’t quite gotten to the details of what that exactly means for me. I wrote about the entrepreneurial journey some years back. This 'update' post has been on my mind for several minds for several months, but I haven't had the time to distill my thoughts particularly well, or perhaps I've had the courage to put it up?

Building a business from scratch is HARD, HARD, HARD. It is not for everyone. The probability of real success is pretty low. A majority of new businesses fail in just the first year. It's a hard fact (pun intended). It doesn’t mean that one shouldn’t attempt it; far from it. In fact I know people who wouldn’t do anything else - but it doesn’t make it any easier. Anyone can be an entrepreneur but not everyone should.

Incredibly Difficult

“You only ever experience two emotions: euphoria and terror. And I find that lack of sleep enhances them both.” ― Marc Andreessen

The pressures of figuring out a business model as you tackle a problem worth solving at a suitable scale, figure out revenue, compliance (very important - ask fintech companies), while at the same time trying to keep the doors open (business  and home), suppliers happy, the team content and engaged, and a myriad of other issues (wars, famine, recession), is draining, and more often than not, only another entrepreneur would be able to empathise with the ups and downs of the journey. It is a highly stressing endeavour - physically and mentally. So next time you see a business founder, give them a hug. They might be smiling but gritting their teeth as they do so.

In my case, I stepped away for reasons personal and practical: I needed a mental break, and more importantly needed to give my family a break 😃 after four years being part of two startup endeavours, and prior to that leading iHub from 2013-2016.

I briefly shared about this journey on episode 25 of 9 to 5 with Wangari (July 2022). Like Oscar Limoke once commented, I struggle really hard to listen to myself so please go listen for me.

Entrepreneur to Employee

Transitioning back to formal employment has been a journey of self discovery. It has not been easy. To start with, I was not sure what I wanted to spend the next few years doing. I was certain that this would likely still be in or adjacent to tech, and include building and growing teams, and solving a big enough ( or complex if you like) problem across Africa.

I have a diversity of interests, skills and experiences so an important decision I had to make was to decide what and where to focus on based on the opportunities available and my 'toolbox'. I suspect that I will make this decision several times  yet. I still keep clarifying my current activities and work by asking myself whether I am creating opportunities and enabling people and companies to thrive usually with tech as an enabler. Personal alignment with a big enough mission along with lifelong learning are the make or break elements of what I do on a daily basis whether it's working for someone or building a startup.

I also learned (and continue to learn) that job prospecting and interviewing is a special skill 😃 that gets better with practice. It is selling (yourself) at the end of the day so one must get in there to be good at it. This is a pretty useful thread[KE focused] on the process of prospecting and applying for a job.


As part of CSquared's Cloud team, we are enabling enterprises across Africa connect to and consume cloud services flexibly and securely. I lead our team of cloud solutions architects, and value the engaging conversations with businesses  on issues cloud and security. Do ping me if you'd like to chat more about the stuff we are doing.

Beyond my 'official' job, I like that each person at the company inevitably gets to wear at least one more 'unofficial' hat as a way of broadening one's experiences. Range is important! I've enjoyed plugging into some of the business (which includes stuff I've done in the past) and see the value of building and stretching my sales muscles.

Employee to Entrepreneur?

Will I be back someday into to the trenches of startup life?  I really enjoy building, tackling hard and complex  problems. It is like one of those itches that needs more scratching. Never say never: there are many problems worth solving and I guess it's a matter of figuring out mission alignment, timing among other things.

Entrepreneurially speaking, we're building something new and interesting at CSQ, so that itch is somewhat being scratched for the moment. More on this at the right time!