Hunting for Boring Problems

Follow the sighs

Leeds is where the idea began on paper. The habit that got me there started a few months earlier, in a dental clinic on Tonk Road in Jaipur, where I was waiting to have a cracked molar looked at and trying not to think about the drill.

The receptionist was called Pooja. It was a Friday, a little after six in the evening, and the waiting room smelled of clove oil and the samosas someone had brought in a paper bag. Pooja had a stack of handwritten case sheets on her left and a computer on her right, and she was copying procedure codes from one to the other. Each code went into a portal run by an insurance middleman (the company that sits between the clinic and the insurer and decides whether a claim gets paid). Every few minutes the portal logged her out. She would log back in, find her place on the paper with one finger, and type again.

And every time it logged her out, she sighed. A small, practised sigh, the kind you develop for something that has annoyed you for so long it no longer deserves anger.

"How long does this take?" I asked, because I am nosy and the drill was still a while off.

"Friday evenings," she said. "All of it. Doctor writes, I type. If I make one mistake in the code, the claim comes back in three weeks and I do it again."

"Every Friday?"

"Every Friday since 2021."

I did not build anything for Pooja's clinic. I want to be honest about that, because this is not a tidy story where I rushed home and wrote software. I went home with a temporary filling and a strange itch. I had spent a year building things I thought were clever, and here was a person losing roughly three hours a week, about 150 hours a year, to a problem nobody on any startup forum was talking about. Nobody tweets about insurance codes. That silence is exactly the point.

Here is my strong opinion, and you are welcome to argue with it over chai: the best ideas for a small software business are not found by thinking. They are found by watching someone work and listening for the sigh. Brainstorming in a notebook gives you ideas that are interesting to you. Watching gives you problems that already cost someone their evenings, and often their employer's money.

After Tonk Road I started noticing sighs everywhere. The chartered accountant's assistant downloading bank statements one month at a time. My cousin's freight-forwarding office, where a man named Ramesh retyped container numbers from emails into a spreadsheet and then into a customs form. The same number, typed three times.

Pooja, I later heard, still does the codes on Friday. The portal still logs her out.

The Napkin hunt

A habit of noticing sighs is lovely, but it leaks. For about two months I noticed things and remembered none of them. Then I started keeping a page at the back of my notebook, and later just a napkin from whichever chai stall I was sitting at, and writing the sighs down before Jaipur traffic shook them out of my head.

That page became the exercise below. It takes five minutes. Do it tonight, before you read the next section, because the next section only works if you have a list.

Napkin: The Boring Problem Hunt

Write down every task you have personally seen someone do in the last year that was done badly, slowly, or at a cost. Work, family, a shop you visit. Aim for ten. For each one, note:

• Who does it (a job title, not "people")
• How often (daily, weekly, every Friday since 2021)
• Rough hours per month
• What a mistake costs (a rejected claim, a fine, a lost customer)

Then circle any task where the person is already paying for help: a temp, an agency, overtime, a junior who hates it.

The circle is what matters most. A problem someone already pays for has a price tag stuck on it before you arrive. You are offering a cheaper or faster version of a cheque they already write.

Here is how Ramesh looked on my napkin, worked through properly. His office handled about 40 shipments a week. Each container number got typed three times, and with the checking, each round took roughly two minutes. That is 40 × 3 × 2 = 240 minutes, so four hours a week, or about sixteen hours a month. Ramesh earned something like ₹250 an hour (about $3), which made the typing itself worth only ₹4,000 a month. Not exciting. I nearly crossed it out.

Then I asked my cousin what happened when Ramesh got a digit wrong.

"The container sits at Mundra," he said. "Demurrage. Last time it was ₹18,000 before we sorted it."

One typo cost more than four months of Ramesh's typing. That is the column most people skip, and it is usually where the money hides. A dull task is a decent idea. A dull task where one slip costs a fortune is a business.

A few warnings from my own napkins, which were mostly wrong. Leave off tasks only you find annoying, unless you are the customer. Leave off anything that happens once a year; nobody subscribes monthly to a yearly pain. And be suspicious of any line that makes you excited before it makes you curious, because excitement is how I lost four months the first time.

My first proper list had eleven lines. Nine of them were useless. One of them was in a building in Leeds, and I had only heard about it secondhand, in a WhatsApp message from a woman I had never met, complaining about Monday mornings.

Ten conversations, three card numbers

The woman in the WhatsApp message was Claire, office manager at a lettings agency in Headingley. A friend of a friend had forwarded her complaint: every Monday she turned landlords' scrawled notes and forty phone photos into property listings, three times over, because each portal wanted a different length and a different order. I wrote to her that evening. She replied the next morning with one line. "If you're selling something, I'm busy."

I wasn't selling anything. That is the first rule of these conversations, and it is harder than it sounds, because every part of you wants to describe the clever thing you are about to build. Don't. You are there to learn how their Monday actually goes.

These are the questions I used with Claire and the nine people after her. I still use them.

• Walk me through the last time you did this. (The last time, not "usually". People lie about "usually" without meaning to.)
• How long did it take, and what were you doing instead of it?
• What have you already tried to fix it?
• What happens when it goes wrong?
• Who else would have to agree before you paid for something?

The third question is the one that sorts people. Claire had tried a template in Word, a freelancer on Upwork at £12 a listing, and a nephew. The freelancer got the bedroom counts wrong. The nephew went to university. Someone who has already spent money and patience on a problem is someone who might spend again.

I spoke to ten letting and estate agents over five weeks, mostly on video calls at awkward hours because of the time difference. Before those calls I had a plan. I was going to build a full listings platform: photo editing, floor plans, automatic posting to every portal. Six months of work, I reckoned, and I had drawn it on the whiteboard in three colours.

Then call number four. Graham, who ran a two-person agency in Harrogate, listened patiently and said, "That's very kind, but no. The portals already post for us. I don't need another login. I need the words written properly, with the compliance bits in, so I don't get a letter from Trading Standards."

A polite no. It wiped out about four-fifths of my whiteboard. Every agent after Graham said a version of the same thing, and none of them mentioned photos at all.

So I stopped describing a platform and started describing one job: paste in your notes, get three portal-ready listings with the required legal lines, in your agency's voice. At the end of each call I asked a question that still makes my stomach tighten. "If I had this working in six weeks, would you pay $49 for the first month now, refundable if I miss the date?"

Seven people said they would think about it. Thinking is free.

Three sent card details. Claire was the first, at 11:40 on a Tuesday night her time. Her message said, "Fine. But if it calls a box room a 'cosy study' I want my money back."

One job, done annoyingly well

Three people had paid $147 between them, which meant I owed them software in six weeks. The whiteboard still had the three-colour platform on it. I took a photo of it for sentimental reasons and wiped off nearly everything.

What stayed was one box to paste notes into and one button. What went was a much longer list, and writing it down was oddly painful:

• Photo uploads and editing
• Floor plans
• A dashboard with charts
• User accounts with passwords (I emailed each agent a private link instead)
• A billing page (I charged cards by hand from the payment provider's website)
• Any way to change your agency's "voice" yourself

That last one I did manually. Each agent sent me five listings they were proud of, and I wrote their house style into the prompt myself, one agency at a time, at my kitchen table with chai going cold. Meera watched me do this for Graham's agency on a Sunday evening.

"So the robot is you," she said.

For the first two months, partly, yes.

I hold a strong opinion here, and I know some people disagree: if your first version doesn't embarrass you a little, you waited too long to show it. My candle-shop tool had beautiful buttons. I know because I spent most of a week choosing their colour. Linda never mentioned them once. What she mentioned, in an email I still have, was that it kept calling her soy candles "waxy", and she didn't want her candles to sound waxy.

The listings tool was ugly. Grey text, a white box, a button that said "Write". The first week it took forty seconds to respond and occasionally just didn't. Graham sent a screenshot of an error message with the line, "This is hideous. The Harrogate one was perfect though. Did you know about the EPC rating rule?" I did, because he had told me on call number four, and I had built the tool so it would never leave the energy rating out. That was the job. Get the legal lines right, every time, in the agent's own voice. Everything else was decoration I could add later or never.

This is the trade you are making. A narrow product that does its one thing so reliably that people put up with slowness, ugliness and the founder charging their cards by hand. People will forgive almost anything except the job going wrong. Claire checked every listing for six weeks looking for a "cosy study". She never found one. In week seven she stopped checking.

By the end of that summer I had three paying customers, a tool that worked, and a folder on my desktop with three more invoices in it. I also had a problem I recognised with a slightly sick feeling. Somewhere in Britain were a few thousand letting agents losing their Monday mornings to the same job, and not one of them had heard of me.

I had been here before. Last time, it took four months and a barking dog.