2024–2026: Starting again

The specification wasn’t written about any market in particular. Every clause was the negation of something that had cost me.

Then a friend showed me his inbox.

Mike runs a fresh produce import business. His operational life, it turned out, looked like mine in 2007 — not metaphorically, literally the same shape: critical information trapped in email attachments, retyped by hand into systems, by people whose actual job was something else. Bills of lading, phytosanitary certificates, packing lists, arriving as PDFs from shipping lines and exporters, transcribed into the ERP, error by patient error, while containers of perishable fruit crossed oceans on deadlines measured in shelf-life. The spreadsheet-emailing of 2007, wearing a hi-vis vest.

And the specification matched. Fresh produce importers don’t google for software; they buy from people they trust, at trade shows, on the recommendation of someone they’ve traded with for twenty years. There is no keyword auction to be outbid in, because there is no auction. Deep ERP integrations are the natural shape of the product, and switching costs the natural consequence of doing the job well. And at the center sits the exact technology that deflated translation — document AI — except here it creates the value: machines reading the paperwork that humans were wasting their days retyping.

I should be accurate about the competition, because “nobody is looking at this” would be false and easy to check. Document AI for supply chains is a busy, well-funded space. Customs and freight document automation has taken serious venture money, several companies are doing it well, and the large logistics platforms are adding it to what they already sell. What is different about my corner is the customer: small and mid-sized fresh produce importers, companies of dozens rather than thousands, running specific ERPs, on perishable-goods timelines where a document arriving late has a cost measured in spoiled fruit. That is too small a wedge for anyone who needs six-figure contracts to make the model work, and too particular to serve with a general document pipeline. The moat isn’t that the space is empty. It’s that this part of it is unglamorous, sold through trade halls rather than demos, and takes more integration depth than a funded roadmap wants to spend.

I started building in January 2026. The stack, you will be unsurprised to learn, was Rails — the same instrument, twentieth year of practice. I called it Trackberry.

What eighteen years bought

Building the second company revealed what the first one had actually been for.

The speed came from WTI. A working product in weeks, not quarters, because every architectural decision had been rehearsed for eighteen years — including background jobs for the heavy document processing, the same unglamorous plumbing that beat the incumbent in 2008, still working in 2026. The file-handler months turned out to be a transferable discipline: parsing the world’s messy, undocumented, lying file formats is the same job whether the file is an Android XML or a scanned packing list from Peru — you sit with the real files until the edge cases surrender.

The market judgment came from the scar tissue. I priced from day one. I charged for integrations. I kept costs near zero — the entire company runs on less than what I once paid monthly to defend my own brand name. And when the first prospects went quiet for two months, I did not conclude the product was wrong, because I had finally learned to tell the difference between a broken product and a market that simply buys slowly. In translation, slow buying would have meant death by funded competitor. In fresh produce, it means the moat is real: any market this hard to enter is this hard to leave.

Even the distribution is the mirror image. WTI’s customers arrived through search results I eventually couldn’t afford to stand in. Trackberry’s arrive through a freight forwarder who was impressed by what I’d built, through an ERP integrator who trusts me because I shipped what I said I’d ship, through a trade journalist, through a hall in Madrid every October. There’s a private irony in that. The only competitor email I ever answered in the old days was the one that arrived carrying a customer’s word-of-mouth about the man who sent it. It took me until my forties to notice that if that was the only door into me, it was probably the only real door into everyone.

I still build alone, happily, and picking up the phone still costs me more than writing a thousand lines of code. What changed is scaffolding: pilot frameworks, follow-up rules, pre-booked meetings, every prospect interaction ending with a date. Mechanics where charisma should be.

One knock per gate

For years I told the story of the old defeat wrong — first as “they cheated,” later as “the game was rigged.” Both contain truth. Neither is the verdict.

The rigging was real: auctions priced by other people’s investors, search results owned by compounding content budgets, network effects that sent every open-source project to wherever everyone already was. I tried the fair channels, mostly once each — the ads that worked and couldn’t be affordably scaled, a conference application that was refused, a free open-source tier that couldn’t move the network, an MIT-licensed CLI that bought no halo. All true. And when five different channels fail for one operator over one decade, the common variable stops being the channels.

Here is what I actually did at each gate. The product got eighteen years of daily iteration; the file handlers alone got months of grinding until every edge case surrendered. Each distribution channel got one knock. When the knock went unanswered, I accepted the verdict instantly and went back to code — where verdicts could be appealed with effort, where effort reliably paid, where I was safe. Look at the design of those experiments: minimum exposure, single attempt, immediate acceptance of failure, return to comfort. That is not a growth strategy that happened to fail. That is a shy man’s experiment design, built — I genuinely believe unconsciously — to confirm that the uncomfortable work didn’t pay, so the comfortable work could continue with a clear conscience. I A/B-tested my parsers relentlessly for eighteen years and never once iterated a growth channel.

Beneath the choices sat a bigger one, remade annually without ever being examined: I stayed solo. A solo operator spending every hour on product and support has structurally zero hours for the slow, compounding channel work that growth requires — so staying solo was the decision not to grow, renewed every year for fifteen years. And the enabler deserves naming: the business was too successful to force me. The comfortable game paid well enough, for fifteen consecutive years, to fund avoiding the uncomfortable one. Broke founders learn sales in year two or die. I never had to, and so I never did. I avoided sales for fifteen years, and it cost me the decade.

So: was I cheated? Some tried. Was the game rigged? Substantially. Did either of those decide my decade? No. What decided it was one knock per gate, an empty chair I declined to fill, and a life comfortable enough that nothing ever made me knock twice.

Where things stand

The memoir format tempts a founder to narrate victory before it happens, so here is where things actually stand. Trackberry, as I write this, is not yet a success. It is a strong start: an excellent paying client, a shipped ERP integration, a real pipeline, a trade show in October where the next chapter gets decided. The “two successful companies” sentence gets earned somewhere around client five. I’ve stopped predicting.

WebTranslateIt, meanwhile, settled into something better than the cash cow I once resigned it to. Over eighteen years it has grossed more than €3.5 million, and it is still gliding gently — but in 2026 I gave it a full redesign and a set of AI features, not to re-enter the growth fight, but because a product I’d stopped resenting turned out to be a product I could enjoy improving again. Several of the funded competitors ended up consolidated into private-equity rollups and rebranded around the AI that shrank the category, their boom-year valuations quietly underwater. The fairest player of my cohort — a bootstrapper who found distribution nobody was contesting and built it into the product itself — is thriving, and deserves it.

One more thing has started happening, and I’ll report it flatly, because it is too early to mean much. Private equity does a predictable thing to the software it harvests: prices rise, support thins, roadmaps freeze. I wasn’t planning a comeback — I was keeping the lights on and the door unlocked. Lately a few customers of the consolidated competitors have come through that door with migration questions. It is a trickle, not a flood, and WTI’s category is still deflating under everyone. But the shape of it is worth writing down: the rollups’ pricing is quietly sending some customers back to the product that was supposed to have been made obsolete.

What it was for

If you’re a bootstrapper somewhere in your own second act — outbid on your own name, out-shouted by content farms, watching effort and outcome come apart and concluding the broken variable is you — this piece exists for the sentence I needed in 2019 and didn’t have: the game can be unwinnable while you are playing it perfectly. And for the harder one: check how many times you actually knocked. Merit didn’t die when the money arrived; it moved — out of the auctions and the search results, into trust, domain depth, integration work, the boring verticals.

The next chapter gets decided next month, in a hall in Madrid, at the trade show where fresh produce importers buy from the people they trust. I’ll be there, doing the thing I spent a career hiding from.

Málaga, 10 September 2026.

In this series
← 2012–2024: When the money arrived