Being a programmer is both the biggest bane and boon in my entrepreneurial journey.
There ought to be more tutorials on how a programmer should run a company. Because this tutorial can be easily written in a single sentence: If you want to be a CEO, don't be a programmer.
In the years that I was addicted to startup porn, otherwise known as Hacker News, there was not one article about a programmer-led company. So I will do the honors with a short story.
Wait for me
It is 2016, and I had two other programmers and me in a teeny rental office in Nanyang Polytechnic (I lied that I was an alumni), and we wanted to build the largest VPN product. One click and boom, an instant VPN connection.
We hold weekly product meetings on Mondays, and I will pepper the presentation with the features that we need to build.
Both programmers will always enquire how they can begin on their tasks. And my reply will always be along the lines of: "Ok let me write the interface first."
Everyone was always waiting for me before they can get started.
Programmer as a boon
I had a hard time raising money, so I took jack of all trade to a whole new level. I am the designer, programmer, marketer, and customer support for most of my early products. And I loved it he necessity to dip my toe in the various facets of the product business made me a great product manager. I had no choice, my products had better be good so they make me money. Or else it will be the end of my self-employed journey.
Programmer as a bane
Unfortunately, the early success of my products had me assuming that if I delegated the roles, I would lose control of the reasons that my early products succeeded. Also, what if the company downsizes? So I self-rationalized that I had to keep this control around.