I’m writing the below on a Saturday evening (December 13th, 2025), while sipping on tea from Tea House Theater, located in Vauxhall (London).
Although I more or less shut down my software (consulting) business earlier this year, Crossbill close down officially as of December 04, 2025.
As I type this out, a few questions come to mind:
- How do I feel about the business shutting down?
- What were the motivations?
- What are the lessons learned?
- What would I have done differently?
How do I feel about the business shutting down?
Surprisingly, not really filled with much guilt. I do feel a sense of pride of what I had accomplished during those 4 years of operation though. Creating something out of nothing (see hunting for clients below). Finding different ways to generate revenue; providing jobs and finding jobs for people
And the primary emotion I am filling right now is relief.
Relief from no longer having to pay taxes and managing Quickbooks.
Relief from all the unnecessary overhead of running a tiny little business.
Relief.
What were the motivations of launching Crossbill
I started Crossbill in the summer of 2021. The business came to life shortly after I had left Amazon Web Services (AWS) as software development engineer. I had always wanted to run my own business and had the desire to “be my own boss.”
While there are huge upsides of running your own business, there are significant drawbacks that I had not fully considered when I had made the leap. Like many others who venture out on their own, I found myself in a situation in which I was fully responsible for making shit happen, fully responsible for generating revenue: nobody was coming to save me. Goodbye to the steady payroll. I had to make something, out of nothing.
Lessons learned
On learning how to sell
Totally forgot that I had done this but I ended up signing up for SPIN course (here). Prior to running Crossbill, I had zero experience in a sales position. Upon reflection, I think some of my challenges — in addition to lack of experience — was my high need for acceptance, my sensitivity to receiving rejection. After becoming aware of this baseline disposition (present in my dance / creative life), I’ve learned (and continue to learn) how to overcome (perceived) rejection, which is the cost to play. It’s like dating: receiving “no” is part and parcel of the experience.
Hunting for my clients
They say innovation is sometimes born out of frustration and desperation and think that also applies to how I went about landing clients. A few memorable ones:
- Responding to a LinkedIn message for a software engineering position, which lead to going on a walk with the CEO around the Arboretum park in Washington and within a few days, converted them to my first paying client
- Cold e-mailing and calling a rather (deliberately) anonymous user on hacker news – reading a thread about customer relationship management (CRM) software and had reached out to someone who I had viewed as very knowledgeable on the topic and that phone call translated into them becoming a customer of mine
- Cold e-mailing a YCombinator backed company (i.e. Quadrant Eye)
What would I have done differently?
- Hired someone to manage my books for me
- Secure a physical mailbox
- Put myself on payroll sooner
- Had more expenses / business write offs during the early stages
- Hold my contractors and third parties more accountable for their actions
Summary
I have so much more to say about this but this blog post was something I wrote as a means to brain dump.
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