During the most profitable year of ZipX, I had full time roles as both its CTO and CEO at the same time.
I found the context switching between the roles was hard. They required completely different mindsets.
Coding is a sniper rifle
As CTO, I outlined exactly what I needed before starting anything. For instance, one goal we had to let people paste a link to any e-commerce store and we will be able to read the item pricing, guess its weight, and try to estimate the customs tax to import into different countries.
I would look at different technologies and tweak and tweak the code until the cross hair lines up. Making it work was a matter of focusing and tinkering.
Our defining feature was you could paste a link of any random e-commerce product from any other website and we would try to spit out a price for you to pay to deliver it to your country.
A board member wanted to prepare a pitch of our company for a partner. When they asked me about our product and I was in CTO mode, I would err on the side of pessimism and reality.
I wouldn’t claim we could really spit out a price for EVERY e-commerce website out there.
We used a plethora of services that specialized in being able to scrape our most requested websites. Amazon and Walmart covered about 70% of our requests.
But we also had thousands of small websites customers would randomly give us that we had never seen before. Japanese websites in particularly had designs all over the place. Another service used really basic machine learning to pull that info from pages and estimate those. It worked most of the time, but probably failed 10% of the time.
The pessimism helped me narrow down what our technical weaknesses were. If I had deluded myself into pretending the product was better than it was, I couldn’t measure and improve.
Marketing is a shotgun
As CEO, I tried a dozens of things. One channel would work out of a dozen.
We tried everything we could imagine. Social media ads, physical posters, sales calls, influencer marketing, free samples, door to door sales, customer referrals.
All of them could potentially hit but you have no idea which until it does.
In CEO mode, I was forced to be optimistic. Otherwise I would have given up when the first channel didn’t work out.
When selling our service, I am trying to ease their concerns. So you naturally start to think of your product in the most optimistic scenario possible.
Every transaction in the world is an exchange of money for reduced risk. You buy a bus ticket for the upfront cost of gas versus a car. You buy a sandwich for the flat cost of making your own.
You don’t put up an online ad and give a long description of the potential issues of your product.