What running my own venture taught me about corporate IT

Note by Khaqan Shaheen. Published 8 September 2026. About 433 words. Topics: side-venture, corporate-it, lessons, operations.

Paying the bill yourself, watching what real customers do on a booking page, finding a pipeline that had stopped without telling anyone, and having search traffic answer back. Each of those changed how I run IT for an employer.

Alongside the day job I run a small technology venture, where I built the web platform, booking flow, messaging automation, search and content systems and analytics myself, and where I run the paid search. It stays unnamed here because the name is not the point. The first lesson was owning the bill and the outcome at the same time. At work a server or an advertising budget is a line somebody approved. At the venture it comes off my own card, and I notice a runaway process, a subscription nobody uses, or a keyword bringing the wrong clicks within days rather than at the next budget review. I now look at group spend as if it came out of my account, and I keep finding things.

The second lesson was the booking page. I built the flow, and I assumed people would use it the way I had designed it. They do not. They do not read. They skip fields. They get to the form and leave, and many message on WhatsApp instead, asking the question the page already answers. That changed how I look at every form I give staff in the ERP. If a customer will not complete a form for something they want, a warehouse clerk will not complete one for something they do not, and the answer is fewer fields and a channel they already use, not a training session.

The third lesson was the pipeline that silently stopped. A scheduled job that published content stopped running, and nothing told me, because it did not fail. It simply did not run. I found out later than I would like to admit, by noticing the absence. Every unattended job I now own at work has to prove it ran, with an alert on silence rather than only on error, because silence is the failure mode nobody designs for.

The fourth was search traffic answering back. Publish a page and within weeks the search console tells you whether anyone wanted it, in clicks or in their absence. Corporate IT almost never gets feedback that direct. Nobody tells you the report you built is unread. I now check who actually opens the things I build, and I retire the ones nobody does.

None of this needed a venture to learn. I did not learn it until the bill had my name on it.