Do you really want to be a CEO?

I remember the day clearly. It was in the “winter” of 2012 when I hit rock bottom as an entrepreneur. It was winter because it was cold. It’s funny how cold and misery find each other easily.I was on a school trip in Amsterdam with my classmates and we were having one of those evenings where we had dinner and drinks.

My classmates were mostly senior managers in well to do companies and their career projections were great. We were all around a table enjoying ourselves and talking positively about the future. The only problem was that I was the only one on that table who was running a struggling start up. I was really broke and was watching my expenses during that trip. My classmates were wondering why I seemed to be avoiding spending and in their great hearts they decided to help me out to pay some bills including advancing me some credit to buy my wife and kid some nice presents from our trip in Europe. Little did they know that I had to sell my prized car (wrx) to finance this mandatory class trip and downgrade to a much smaller car (starlet).

With all the stress of a floundering business, hearing stories of success in people’s careers and a bit of tipple all came together to make me a louche. I suddenly turned into a grouch and began arguing with my classmates for no apparent reason. Up-to this day when we meet(we still do meet occasionally), I fear to bring up this episode. The argument got very heated that they all stood up,walked off and left me at the restaurant. I sat there with my mixed emotions. Mostly misery at my situation, but also jealous that these guys were very doing well in their careers and I was here running a business that seemed to be going nowhere. Most of all, if I come to think of it, I was just broke.

Rewind back to 2008. I had a corner office in a vibrant emerging start up in health insurance. My boss was charismatic. Everyone wanted to be him. I had worked here for almost 3 years rising through the ranks from a clinic doctor to eventually a corner office and a prized wrx Subaru. All this achieved before my 30th Birthday. However all this time I harboured ambitions of growing a hobby project called AskADoc (, where we helped people with free advice, from hobby into a great business. With somewhat of a push(story for another day) I handed in my resignation just after I was proposed to join my MBA class. I plunged headlong into the business mostly run out of the servants quarter where I stayed. I had done what the books say “keep enough Savings for 6 months”. It did not work s planned.I burned through those Savings fast. 6 months became 4 years when I found myself seated alone at a restaurant in Amsterdam. Cold.Miserable. Broken. Broke.

When I reflect on the 4 years I ran the company I think I was a terrible CEO. Poor cashflow management, poor marketing. Looking back I beat myself up for being a crap CEO. However, I think where I did well was in cost management. I scrimped. I have been accused of being cheap. This was ingrained from Lessons learned from my dear mother (need to do a post on this woman). This cost containment behavior still exists up-to date even though I work in a well funded start up now. I still think on bootstrapping ideology. The upside of this cost containment with the slowly growing business portfolio helped move the business from my servants quarter to a larger roomed office of karbanet road. A year later we moved into a one roomed apartment on Marcus Garvey road as the small team grew. A year later we moved to a bigger space before we made the leap into buying a hospital (see my post on 2018 the year of recovery). I stopped being CEO when I took up a job offer based on my MBA skills(a great investment). I just needed the break. This was one year after Amsterdam. One year of self doubt and agony. One of my co-founders took over the mantle and has been on the same roller coaster ride I had for 4 years. Luckily, we have tried avoiding the same pitfalls that I went through in our earlier days. Dennis has done a good job of keeping our vision of helping people with health problems and keep the business running. It is still not easy.

The beautiful thing about being employed is that you get comfortable. That is necessary at times. It is even better when the place you are employed has a great vision and leader. I was employed to get an ambitious project off the ground. The project was only for 1 year and after that I would venture back to business. However my 1 year journey has turned into 5 year madness ride and affirms the power of vision by a few crazy guys.

Do I have regrets leaving the ceo desk? Sometimes. But most times I see that you cannot always force on destiny. Enjoy the ride. You can make a change in the world and society whether you are employed, entrepreneur,poor,rich,black,white.

Do I have lessons from being a CEO. Many. Perhaps I can compile it in a blog.

But the questions linger. Would I want to do it again? It looks sexy on the outside but it is damn difficult. In places I have worked I have seen the effects (some similar) of being CEO in a start up. Poor health, strained relationships at home,depression,poor sleep and other countless problems. On the flip I see the rush in e CEO eyes when impossible targets are achieved. I see the impact a CEO has on he lives of the team. CEO s can lead teams that can change the world. Would you want to be a CEO? I leave that to you

One thought on “Do you really want to be a CEO?

  1. Wow!! clearly there is no glamour in a start up and that one question…DO YOU WANT TO BE A CEO?…not for the faint hearted!


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.