@duggan — startups

The dream of v2

2026-06-15T09:17:19.000Z

Joel Spolsky once called it "the single worst strategic mistake that any software company can make", and not for nothing:

"When you throw away code and start from scratch, you are throwing away all that knowledge. All those collected bug fixes. Years of programming work."

Even twenty years into my career, despite understanding, both logically and from experience that a rewrite is a high-risk move with limited chance of success– I still find myself daydreaming about it.

It's easy enough to dismiss other people's mistakes, or even your own, as not applicable, even easily avoidable. But software is built in a time and a place and under very specific conditions. You don't get to reset to the same preconditions and try again. Every retry is a completely different game.

Fred Brooks described one variation of this as the second-system effect in The Mythical Man Month:

"...the tendency for a successful first system (often small and relatively elegant) to be followed by a second system that becomes over-engineered or bloated."

Perhaps it's because I've mostly worked in startups, but the first systems I'm familiar with are big balls of mud^[1] ^[2]that accrue from generalists and novices building products while still trying to understand the domain – and of course find their customers.

As far as I can gather, this is par for the course in startups. It's rarer than perhaps it was in 1976 for a company to start with a team of seasoned specialists working on a domain they fully understand, for a customer that is well defined. Of course, even that is no guarantee of success.

There is also a helpful corollary:

"Brooks separately argues that teams should often expect to build a pilot (or throwaway) system to learn what is actually needed; the management question is whether to plan for that throwaway in advance or to mistakenly ship it as the final product."

I don't think I've ever seen a pilot that does not become the first version of the product. Again, perhaps this is because I've worked mostly in smaller companies, but generally a working artefact for a real problem is too valuable to discard.

I can imagine companies and products where this is different, though they all live in a cozy 90s corner of my imagination where release cycles are multi-year, cash is plentiful, and in defiance of Euclidean geometry, every office is a corner office.

For startups you often must first build a big ball of mud, and you cannot throw it away.

Until now, maybe?

#Fast, good, cheap

There is a project management model called the iron triangle which will be familiar to many software developers. If you don't know it, the basic idea is that there are trade-offs when building something. If you want it done faster, it's going to cost more, if you want it to do more, it's going to take more time, etc. Fast, good, cheap: pick two.

Coding assistants are rapidly changing how we write software. The adage that you can only pick two of fast, good, and cheap, is going to be tested.

In particular, the bar for quality will be permanently raised. In some sense this is not too different from the way that the quality bar for an app or website has risen in the last 30 years – just at a faster rate.

Software is now cheaper to produce; more niche software can be produced by people who don't need to be seasoned software developers. I think this will be good, on balance. There will be more crap, but also more interesting esoterica.

This also means that at least some of the risk of a rewrite should be going down commensurately.

My own timeline for delivering functionality and fixes has gone down, sometimes by an order of magnitude. Code I would comfortably predict would take several weeks to write, test and iterate on in 2025 can usually be produced in a matter of days now. Bug fixing, which often has a higher cognitive burden since it requires more reading than writing, has often become a background task while I'm doing something else.

#A golden era of rewrites?

There's still no magic pipeline to pour in a big ball of mud and have polished marble come out the other side. However, making the process cheaper and easier is going to bring it into the realm of attainability for some projects.

There are techniques being developed, producing results like the quasi-clean-room rewrite of chardet, or the rewrite of Bun from Zig to Rust.

Reproducing a piece of software, or transliterating from one language to another is one thing; a rewrite to me though suggests something that, at minimum, is fixing deep architectural debt. Ideally, it's unlocking new avenues for development, such as faster delivery or improved functionality.

This is a higher bar to reach than mere reproduction. Partly this is because what defines a piece of software, a product, is in people's heads. It's in the various expectations of customers, developers, and business owners, amongst others. It's also the case that providing the original code to an LLM will inevitably anchor the rewrite to the original in ways that may be undesirable.

That said, I have found an agent-based full rewrite valuable even when not shipping the final result. First, it has given me a chance to test out ideas that would have been difficult to retrofit even into a feature branch – the kind of stuff that means tearing out whole subsystems or redesigning the architecture.

Since it's so fast to do, it allowed me to get to a working state very quickly, become more ambitious, and discover things that I might never have done by incrementally improving the original codebase. Some of those ideas were then ported to the original system.

It was also truly cathartic to fix all the things that I feel are broken or badly designed in the original code.

Also, if I'm honest it helped me touch grass a bit and appreciate the value of a functioning system. Sometimes it's easy to forget how much work has been done when all you can see are the flaws.

Certainly it is now easier to produce something complex and polished. However, it still takes time, effort, and money. It still has to be deployed, improved, and maintained. There will still be bugs. Most importantly it still has to be built with intention, and serve customers. It can't just be whatever the agent decides is good enough.

Everywhere you look people are still buying software. They are still complaining about software.

Nobody has the time or money to rewrite every piece of software they use on demand. It may take the market a while to realize that, though.

Notes:

A Big Ball of Mud is a haphazardly structured, sprawling, sloppy, duct-tape-and-baling-wire, spaghetti-code jungle. These systems show unmistakable signs of unregulated growth, and repeated, expedient repair. Information is shared promiscuously among distant elements of the system, often to the point where nearly all the important information becomes global or duplicated.
– laputan.org https://www.laputan.org/mud/mud.html#BigBallOfMud
–

Traveling to Japan for three months because life's too short

2025-02-10T16:49:16.000Z

I've been fascinated by Japan since I was a teenager. Thanks to Hayao Miyazaki (among others) the food, landscape, and architecture all exist in some dreamy, liminal space in my mind alongside wood sprites and lost civilizations.

Maybe it sounds daft, but the idea of actually visiting the country always seemed like it would break the spell somehow? Like anywhere, Japan has crime, social problems, bad weather, and if I go, me.

Same sad you.

That said, I've had a plan (concepts of a plan 👐) to visit for years. I've recently dug out an old copy of Rough Guide to Tokyo that dates from 2011, which was the first time I started vaguely planning to go.

However, that was also the year I started working for Engine Yard, which changed the entire trajectory of my career. This was a huge deal for me, but Engine Yard landing in Dublin was also a big deal for the local startup community – Silicon Republic had an article in 2013 that gives a bit of a retrospective.

Plans to visit Japan went on the back burner.

#Fast forward a few years

Speaking of back burners, in 2019, I was burning out at my job. This was well past Engine Yard, which I had left in 2014. Our startup had been acquired, and corporate bureaucracy was slowly draining away my will over the subsequent three year earn-out. There were plenty of smart and thoughtful people around, but somehow I felt like I was getting stupider.

The work was the most mind numbing drudgery. I had begun to hate writing software, and was terrified that if I didn't leave, I might never recover my enthusiasm.

Then sometime in early 2020 I read a series of blog posts by someone who had cycled the length of Japan, and it rekindled those old plans, but now on a grander scale. This was something I could aim for – I was going to cycle the entire length of Japan.

Clearly this was a huge "my life is derailing, I must escape" signal, but my girlfriend was having a similar crisis and so we agreed on the broad strokes of a New Zealand / Japan cycling tour, taking six months or so to do the whole thing. We both had enough savings to take an extended break from work. I started cycling training in earnest.

On March 1st 2020, I handed in my notice – this was going to be the year I did Japan.

RTÉ News from March 19th, 2020.

As COVID-19 wore on, it became increasingly clear that there would be no Japan trip. I finished out my notice period, and it would be almost a year before I felt like I could write code again professionally. I spent the intervening time doing not very much – I exercised, lost weight, went for long rambles in the Phoenix Park. Visited South Africa while there were still travel restrictions – that was memorable – had to get "war zone" travel insurance as it was the only option that would provide cover during the pandemic.

While I was in South Africa in 2021, David Coallier called and asked me to join as CTO of his new company, Clearword. I was ready to let go of Japan – I didn't want to spend another year on the sidelines, and so I joined David on what ended up being the most interesting and, hilariously, least personally remunerative startup we've done together. We had customers. We talked to them. We zeroed in on a niche. It felt really close to being something – but it never quite got there.

So it goes.

#2025, the year we make contact

And so here we are, in 2025. I am unemployed but am not immediately looking for work.

Emotionally though, things could not be more different.

I was disappointed about Clearword, but the writing had been on the wall for a while, and I came to terms with it months ago. I'll write that all down another time, but the gist is that I am feeling ready to start something new.

I am also turning 40 this year. Life moves pretty fast, and while I feel fitter and healthier today than I did ten years ago, I have to acknowledge that time is passing, and if I put this off now I may not have the opportunity again for a long time. And it's not just my own calendar that has to line up, but that of my girlfriend.

I also no longer feel the need to find myself by cycling the length of a country I've never even been to. I don't need a grand goal. I am going instead to soak in it. To be in the place and take it as it is. I want to do it peacefully and respectfully.

There are places I want to visit, of course – Yakushima island, the inspiration for the ethereal scenery of Princess Mononoke being top of my list.

Photo by Takeshi Kuboki, via Flickr.

Climbing Mount Fuji seems like it would be neat, if it works out, but mostly we both want to go off the beaten path, and avoid bustling around in crowds gawping at geishas, etc.

So – flights are booked. We are going for three months, start of May to start of August. We've booked our flights to arrive in Seoul rather than flying directly to Japan, as it gives us some options on whether we want to go north or south to start (regional flights from Seoul are relatively cheap). North, to Hokkaido, is sort of appealing with the chance of catching the sakura blossoms, but Yakushima is in the south, and it will be better to do that before summer gets into full swing.

In the mean time, I am attending evening classes in the city to learn hopefully enough Japanese to get by. Thanks to years watching anime, I have a surprising amount of vocab floating around in my head, if not all of the practical variety. This week I managed to write out my basic hiragana table from memory, which feels impressive, yet is just the tip of the iceberg.

Three months sounds like a long time, but anyone I've spoken to tells me however long they spent, it wasn't enough. We'll be traveling light and keeping our plans loose, and we are going to have some adventures.

Can't wait. 🇯🇵

Sources

Yakushima photo by Takeshi Kuboki, via Flickr.