What a bass guitar, a Commodore 64, and a mixing desk taught me about becoming a CTO.
A few weeks ago I was cleaning up my Google Drive, which is the digital equivalent of finally opening that one drawer everyone has at home - the one with cables for devices you no longer own, warranties for things that died years ago, and a mysterious key you will never, under any circumstances, throw away, because what if, someday, against all statistical probability, it turns out to open something important?
Buried between old invoices and long-forgotten projects was a PDF called post-production_contract.pdf, and because I am constitutionally incapable of leaving a mystery unopened (this, incidentally, will become a running theme), I clicked on it.
Four pages. Formal language. Deliverables, payment schedules, governing law, and - I want you to sit with this - a royalty clause so ambitious that present-day me would read it, laugh once, and then quietly delete the file out of secondhand embarrassment. Except I didn’t delete it. I read the whole thing, because at the top of the first page, in big bold letters, was a title I hadn’t used in years:
Marco Silvestri – Producer.
I smiled. Partly because I had genuinely forgotten I’d ever branded myself like that, partly because I immediately started mentally correcting my own English from six-years-ago (some habits never leave), and partly because I realized this document belonged to someone who, at least on paper, doesn’t seem to have all that much in common with the person writing this post today. Back then I was living in Nairobi, spending my days recording bands, mixing songs, mastering albums, and teaching music production to aspiring engineers who were, in retrospect, probably as confused as I was. I distinctly remember once negotiating over a discount of one thousand Kenyan shillings (which was roughly the price of two mediocre pizzas!) with the kind of grim determination usually reserved for hostage negotiations. At the time it felt like a battle worth fighting. Today it’s just a story I tell at dinner parties to watch people’s faces do that polite-but-confused thing.
When people ask me about my career, that’s usually where chapter one ends: “and then I left music and became a software engineer.” It’s a perfectly reasonable summary. I just don’t think it’s true anymore, and I’m going to spend the rest of this post trying to convince you of that, so buckle up. This is not going to be a “10 Lessons I Learned Becoming a CTO” post, mostly because I don’t trust anyone, including myself, who can compress a career into a numbered list with a LinkedIn-friendly hook. Life doesn’t ship with bullet points. It ships with a four-page contract you forgot existed and a title that made you smile for reasons you didn’t fully understand until you sat down to write about it.
Here’s a piece of trivia that will do a lot of unearned work later in this post: my childhood babysitter wasn’t a person. It was a third-hand Commodore 64. If you’re old enough, you already know exactly what I mean — the several minutes spent waiting for a game to load off a cassette tape, only for it to fail at 98% and force you to start the whole ritual over, which I now realize was basically an early, unpaid course in resilience engineering. If you’re not old enough, I genuinely don’t know how to explain the specific flavor of despair involved, so just trust me.
The strange thing is that, despite having a computer practically raising me, I did not become a programmer.
Not even close.
Not because I wasn’t interested in technology — I just didn’t know yet that the thing I was interested in had a name. I, instead, picked up a bass. I learned how microphones worked, then became weirdly, obsessively fascinated by compressors and equalizers and the invisible plumbing of a signal chain — the sort of thing nobody at a date wants you to explain to them, and yet I did, repeatedly, to anyone who made the mistake of asking what I “did.” Eventually I ended up teaching those subjects professionally, which felt, at the time, like the whole story.
Then, in what still feels like an absurd plot twist someone else wrote for me, I re-discovered web development. And here’s the genuinely embarrassing part: in 2020 I barely understood how a website worked. Reverse proxies? No idea. Virtualization? Just dabbled in that. Containers? Something ships arrive in, surely. If you’d told me that six years later I’d be spending my evenings happily arguing with myself about storage architectures, monitoring pipelines, and backup strategies, I would have politely suggested you turn down the reverb on your headphones, because clearly something was distorting your signal. And yet, here we are.
People generally describe this as changing careers. Music producer, then software engineer, then CTO: three careers, three identities, a tidy little LinkedIn narrative arc. The more I sit with it, the less convinced I become, because every hobby I’ve ever truly loved shares one thing, and it’s not the subject matter. It’s the structure underneath it. Take board games, which I supposedly play for fun. Somewhere around round two I stop seeing farmers or spaceships and my brain quietly starts ignoring the artwork to look underneath it instead - why this mechanic creates tension, why everyone turns hostile around round four like clockwork, why one tiny rule rewires how eight rational adults behave toward each other. My homelab is the same instinct wearing a different costume: visitors see racks and what they generously call “an unreasonable amount of Ethernet cable,” I see an experiment in redundancy and disaster recovery that happens to run on hardware. It took me embarrassingly long to notice this was also true of music. People assume mixing is about making songs sound nicer. It isn’t, or at least that’s not the interesting part. It’s about understanding a system: a microphone feeds a preamp, the preamp feeds a compressor, and every decision propagates downstream whether you meant it to or not. Nothing in a signal chain exists in isolation, which will sound extremely familiar to anyone who’s debugged a Kubernetes cluster at midnight. Years later I found myself drawing infrastructure diagrams instead of signal chains, and the nouns had changed: clients became users, mix buses became networks — but the reasoning underneath was identical.
Somewhere along the way I became a CTO, which is the part of the story where people expect the climax to happen. Ironically, it’s probably the least interesting bit. Titles are funny that way, a CTO is a bit like the bass player in a band (you’ll notice I keep coming back to bass, and no, that’s not an accident, it’s basically the thesis of this whole post disguised as a running joke). Nobody walks out of a concert saying “did you hear that incredible E on beat three?” But pull the bass out of the mix and suddenly four genuinely talented musicians sound like they met in the parking lot five minutes before the show and are only now realizing it.
Good bass players make everyone else sound better without anyone quite noticing why.
Seven months into being a CTO, I’m starting to suspect the same principle applies here. Long before I had this particular label attached to my name, I was already managing teams, coordinating people, designing studios, teaching classrooms and trying to create environments where other people could do their best work. The instruments changed. The problem didn’t.
What I am beginning to understand, though, is that my job isn’t to be the smartest engineer in the room, or to write the most code, or even to make every decision. Instead, it’s to build an environment where good engineering keeps happening even when I’m nowhere near it.
The funny thing is that “CTO” sounds like I’ve reached the final boss.
It doesn’t feel like it.
It’s just another role in another system.
In a band, nobody wins because they have the most technically gifted bassist. They win because everybody plays together. The more I experience the role, the more I notice that companies work in surprisingly similar ways, which is a roundabout way of admitting the title on my LinkedIn is basically a second-order effect of the same instinct that made me chase compressors and homelabs and board-game mechanics in the first place. The title is the artifact. The system underneath it is the actual point.
Looking back, I genuinely don’t think I’ve ever been passionate about music, or Linux, or cloud infrastructure, or board games, specifically. I’ve been passionate about systems, full stop, and music simply happened to be the first one I got my hands on. Board games are one. Companies are one. Software is unambiguously one. Even teaching, now that I think about it, was never really about audio. My favorite moments in a classroom were never the ones where I demonstrated a compressor or explained equalization; they were the moments where I watched someone suddenly connect two ideas that, five minutes earlier, looked completely unrelated. Turns out that’s a systems problem too. Learning is a system. Teams are systems. Organizations are systems. Careers, perhaps (and this is the part that genuinely surprised me while writing this) are systems too.
Sometimes I wonder what would’ve happened if I’d enrolled in Computer Science instead of chasing music halfway across the world. Maybe I’d have become an engineer ten years earlier. Maybe I’d have hated every second of it. Maybe I’d still be producing records in Nairobi. Maybe I’d be designing board games instead of infrastructure diagrams. Honestly, I don’t think any of those alternate versions of me would be fundamentally different people, because they’d all still be spending an unreasonable amount of time asking exactly the same question: if I change this one thing, what happens to the whole system?
Finding that old contract didn’t feel like remembering a previous life. It felt more like being reminded that I never really changed careers at all.
I only changed playgrounds ⚒