I style myself a pirate, not because I steal anything, but because life is better with a little fun in it.
I craft software. These days I'm focused on figuring out what that means with the explosion of "AI". I remain a steadfast full-stack developer, but have found that I'm much more programming-language agnostic these days. The goal of delivering working, impactful software hasn't shifted, but the way I bring it into existence sure has. I remain faithful to being agile in principle instead of agile by hype. I'm so curious how we now turn juniors into seniors in this new "era" and would love to discuss any thoughts you may have on the topic—contact me here.
I've always worn multiple hats. Turns out my proclivity for asking why so much they move you from Full-stack Software Development to Product Management is a useful trait in this new frontier of agentic development. In my decade (...plus) crafting software professionally, I've held quite a few roles—Full-stack Developer, Business Analyst, Product manager. This broader view/experience on the business of software is proving an asset these days.
I'm building @Qwyn AI. I should probably sell you on the business, but I don't want to. Here, on my own site, what I want to sell you on is the people. I truly appreciate our founding team's dedication to not merely doing business, but to doing it together. As some of you know, early stage companies are full of strong emotions and tense moments. I feel incredibly lucky to be once again (cc the @pactsafe crew) working with folks who see the people involved as much as the business itself. Granted I stole this focus as any good pirate would…
Now onto the full story...
I dread the dreary drudgery of dull repetition that so often plagues the day-in and day-out of a human's professional endeavors. So I decided to say f••k it and became a pirate. Despite the potential detriment the association to actual pirates' actions may bring me (or mine to theirs), I find the moniker a useful focal point to remind myself to never become mindlessly complicit in existing systems. So, even if my childhood self is slightly disappointed with me… No, I do not raid upon the high seas. And even if you, the reader, are slightly disappointed with me... No, I am not a source of technological thievery.
I do feel compelled to disclose a bit of the background behind this decision. I did indeed steal my pirate label. Some of my more formative professional (and personal) lessons came from a time I lent what skills I had to some self-styled pirates as they were getting a business off the ground. They inspired me and taught me so much that I straight up stole their pirate imagery. They likened themselves to pirates because they were unconcerned with the status quo. Rather they were seriously focused on doing things well even if that meant doing things vastly different. It's a lesson I hope never to forget. And so, with a brazen act of persona-crafting theft, I anointed myself piratematt. It is perhaps more accurate to say they were helping me get my sea legs, than I was helping them build their ship. I'll forever be grateful for those humans who started Habitry and welcomed me so openly.
My pirate moniker serves as a constant reminder. It's a constant reminder to always be a little silly and have a little joy. It is a constant reminder to be fearless when it comes to being and doing things differently. If there is a better way, take it. It is a constant reminder to look for a good ship with a good captain and a good crew. Money is a great enabler, but I am more interested in finding places, people, and environments that help me thrive.
Unsurprisingly to those who know me. I have opinions. A lot of them. (If you want me to, I'll even create one on the spot and defend it on the fly.) However, a ways back I realized my goal isn't to have opinions; it's to get outcomes. So I'm constantly working on holding my opinions loosely. Throughout this prolific opinion having ability, I find several common threads driving the majority of my software opinions. These align quite frequently with the writings of Ron Jeffries. This is a great example from Ron. Here are a few of my own:
I've spent a decade (...plus) crafting Software. I started my career after four years at university attaining a BS in Computer Science with a concentration in "Software Development" and an additional specialization from the "Systems" program. I've been a human of many hats, holding various roles: senior full-stack software developer, technical product manager, business analyst, and more. I've spent time working for myself and I've spent time salaried working for others. Perhaps most notably, I'm currently the founding Software Developer @Qwyn AI. Prior to that my last salaried run was at PactSafe—a legal technology SaaS startup founded in Indianapolis. I joined as headcount #9 and help grow the company to and through an acquisition with Ironclad. I enjoy mentoring and I prefer to work with/on self-organizing teams.
I find the industry (and the craft) in a weird position. After more than a decade of relative stability, It took about 9 months for my day-to-day to completely transform. The problem I (and others I've talked to) see ahead in let's say 5-10-ish years is a stark gap in senior level talent. I'm very interested in how we get ahead of this gap. The problem is that the way I got here, likely won't be the way others do. For me it was years in the trenches coding. Followed by suffering the mistakes of that coding. I did dumb things that pained team members, and I fixed dumb painful things they did. I learned by writing and rewriting code. In this new era of agentic coding, now I only directly write maybe 5-10% of the code I produce. I mostly design, maintain, and evolve the systems that produce working software. I'm still intimately involved in code-reviews, architecture and the like, but this is an application of hard-won knowledge. The question of how to mentor juniors into seniors looms large in my mind. If you have ideas or just want to commiserate, I'd love to hear others' perspectives.
Our technological development has far outstripped our social systems ability to respond well (and largely speaking our biochemical responses too). I have more questions than answers. Far more. I don't believe we-the-people are handling this well enough, and seem to have entered a backslide. (Not that it was great before, but decade over decade we seemed to be slowly finding paths to progress.) I don't know precisely why I'm including this here. I'm confident recruiters would advise me to remove it, but this is my pirate ship and they're not on my crew; they don't get a vote.
When I'm not answering the siren call of an early stage employee, I often find myself with too many hobbies and desires. I play a lot of board games and TTRPGs with friends. Feeding myself oscillates between a chore, a hobby, and an art form. I randomly dabble in painting, woodworking, writing, and various other acts of creation. I walk, I run, I adventure. I value lazy days just as much as the busy ones. I prefer to treat life as a team-sport rather than a race with only one first-place.
