The most polite mugging

There is a conversation happening at kitchen tables, office desks, truck consoles, and after-hours shop counters across the country.

It is not especially dramatic. Nobody is calling it a crisis. There are no panels about it. No glossy reports with a stock photo of a worried entrepreneur holding a mug.

But it is happening.

A small business owner opens the laptop after dinner, or after the kids are in bed, or after the last customer leaves, and starts doing the new arithmetic of staying alive.

What can we cut?

What can we delay?

What can we do ourselves?

Which bill can wait?

Which “essential” tool is not quite essential anymore?

Can we keep the part-time help?

Can we raise prices again without losing people?

Can we still afford the software that was supposed to make the business easier to run?

These are not abstract questions. They are the quiet, brutal decisions being made in real time by photographers, tradespeople, therapists, designers, restaurants, nonprofits, retailers, coaches, farm-adjacent makers, local service providers, and thousands of people who are not trying to dominate a market. They are trying to make payroll, answer emails, serve customers, and get home before their kids forget what they look like.

And somewhere in that pile of decisions is a growing resentment toward the tools that were supposed to help.

Because the monthly software bill has become one of the strangest line items in modern small business.

It does not arrive as one big villain. It arrives politely.

Nineteen dollars here.

Thirty-nine dollars there.

Seventy-nine dollars because you need the feature that used to be included.

One hundred and forty-nine dollars because your business has committed the serious moral offence of having more than three clients.

Each bill, alone, seems reasonable.

Together, they begin to feel like a very polite mugging.

And I am becoming increasingly suspicious of software that says it wants to “simplify my workflow.”

This is usually the opening line in what later turns out to be a hostage negotiation.

It begins innocently enough.

Somebody spots a real gap in a professional market. Not a pretend gap. Not “what if dog walkers had a blockchain?” A real one.

A photographer needs a better gallery system. A filmmaker needs a smoother editing process. A small business needs a CRM that does not require three onboarding calls, a certificate in operations management, and the emotional resilience of a bomb disposal expert.

So a founder builds something genuinely useful.

And this is the beautiful bit.

For a while, everything works.

The software solves a specific problem. The customer pays a fair price. The company earns a living. Nobody is pretending to change the world. Nobody is describing a scheduling app as “democratizing human potential.” It is just a good tool, doing a good job, for people who are happy to pay for it.

Civilization, in other words.

Then something happens.

The company discovers growth.

Not normal growth. Not the healthy kind where more people discover a useful thing. I mean growth with a capital G. Growth with a pitch deck. Growth with a hockey-stick chart. Growth that comes with a photo of the founder holding an enormous cheque beside a banner that says something reassuring and terrifying like accelerating the future of work.

And that is usually the beginning of the end.

Because the company can no longer simply be good.

It must now be important.

It must expand its total addressable market, which is a phrase that often means: “We have solved one problem well, and are now under pressure to solve six adjacent problems badly.”

The simple tool becomes a platform.

The platform becomes an ecosystem.

The ecosystem becomes a walled garden.

The walled garden becomes a small administrative principality from which escape is technically possible, but emotionally ruinous.

This is the bait-and-switch.

You did not buy software.

You adopted a workflow.

And once you adopt a workflow, you are no longer a customer in the normal sense. You are a tenant.

Your forms are there. Your clients are there. Your invoices are there. Your automations are there. Your staff has been trained. Your templates have been built. Your habits have fossilized.

At this point, a $12 price increase is not really a pricing decision. It is a ransom note written in friendly UX copy.

“Great news! We’ve updated our plans.”

Nobody has ever received good news that began with those words.

The strange thing is that, individually, every subscription still seems reasonable.

The problem is that small business owners do not experience software one bill at a time. They experience it as a monthly fog. A quiet creeping mist of SaaS, rolling in under the door, until one day you realize you are not running a business. You are sponsoring a raccoon colony with login screens.

And every raccoon wants to be your operating system.

That is the truly maddening part.

Every CRM now wants to do email.

Every email tool wants to do landing pages.

Every landing page tool wants to do analytics.

Every analytics tool wants to do automation.

Every automation tool wants to do AI.

Every AI tool wants to replace the other six tools, but only after you spend three weekends watching tutorials made by a man named Chase.

None of these products are quite good enough to replace the others.

All of them are just good enough to keep billing you.

So you end up with a Frankenstack.

Not a tech stack. A Frankenstack.

A lurching, subscription-fed creature made from seven tools, four integrations, two broken Zapier connections, one spreadsheet called FINAL_final_REAL_USE_THIS_ONE.xlsx, and a vague sense that somewhere in your business there is a form submission going directly into the sea.

And this, apparently, is progress.

The great irony of modern business software is that it often creates the very complexity it claims to remove.

It begins by saying, “Let us save you time.”

Then six months later you are in a settings menu trying to determine whether a client reminder is being triggered by a workflow, a sequence, a pipeline stage, an automation rule, or an ancient curse.

This would be funny if it were not so expensive.

And it would be less annoying if the people doing it were obvious villains.

But they usually are not.

Many of these founders are sincere. That is what makes the whole thing more dangerous. They started with a real problem. They cared about their users. They built something valuable. They probably still believe they are helping.

But good intentions do not protect customers from bad incentives.

A founder may want to serve a niche.

An investor may need that niche to become a market.

A customer may want a hammer.

The board may prefer a hammer that also does invoicing, lead capture, email marketing, customer segmentation, AI-powered nail prediction, and quarterly webinars.

This is how useful tools become burdensome platforms.

Not because someone woke up one morning and decided to annoy plumbers, photographers, therapists, designers, nonprofits, coaches, and wedding videographers.

But because the incentive structure rewarded expansion over restraint.

And restraint, oddly enough, may be the most underrated virtue in technology.

There is enormous dignity in software that knows what it is.

A calendar should not secretly aspire to become a CRM.

A CRM should not dream of becoming your website.

Your website platform should not behave as though it has been chosen by destiny to manage your entire customer lifecycle.

Sometimes a tool should simply perform its task, accept money, and go home.

We used to understand this.

A hammer did not release a spring update.

A notebook did not sunset its free tier.

A filing cabinet did not announce that, due to exciting new improvements, drawers three and four were now only available on the Professional Plan.

The old tools had limitations, but at least they had manners.

Modern software is often rude in a very cheerful way.

It constantly asks for more commitment. More data. More migration. More integration. More permissions. More trust.

And then, once embedded, it begins to behave less like a tool and more like a landlord who has discovered surge pricing.

This is where I think the tech world needs a warning.

What is good for one startup is not necessarily good for the whole economy.

One company adding features makes sense.

A thousand companies adding overlapping features creates a swamp.

One subscription increase is manageable.

Every subscription increasing turns into a tax on independence.

One platform trying to own the customer relationship is convenient.

Every platform trying to own the customer relationship becomes a knife fight in the small business owner’s browser tabs.

And small businesses are uniquely vulnerable to this.

They do not have procurement departments.

They do not have software architects.

They do not have someone named Martin whose entire job is to audit vendor overlap and say things like, “We’re consolidating our enterprise stack in Q3.”

They have the owner.

And the owner is also sales, marketing, bookkeeping, delivery, customer service, payroll, tech support, and the person who has to fix the printer by turning it off and whispering threats at it.

These are the people software was supposed to help.

Increasingly, they are the people software is quietly exhausting.

So maybe the next great shift in technology is not more automation.

Maybe it is restraint.

Maybe the brave thing is not building a platform.

Maybe the brave thing is building a tool.

A good tool. A specific tool. A tool with clean exits, fair pricing, honest limits, and no secret ambition to become the central nervous system of a dog-grooming business in Moose Jaw.

Maybe not every startup needs to become a unicorn.

Some can be donkeys.

Reliable. Useful. Slightly stubborn. Capable of carrying weight. Not especially glamorous. Less likely to trample the village.

We need more donkey software.

Software that does the job.

Software that does not need to be adored.

Software that does not describe every minor interface change as “unlocking new possibilities.”

Software that lets small businesses leave without needing a priest, a lawyer, and a CSV file named export_7_FIXED_v2.

Because the current model is starting to corrode trust.

Small business owners are getting wiser. They have seen the cycle too many times.

Useful tool.

Workflow dependency.

Feature bloat.

Price increase.

Plan restructuring.

Lock-in.

Regret.

And every time this happens, it becomes harder for the next honest founder to earn trust.

That is the tragedy of the tech bait-and-switch. It punishes the good builders too.

Because when enough companies turn helpful tools into expensive traps, customers stop asking, “Can this help me?”

They start asking, “How will this eventually hurt me?”

That is a terrible place for an industry to end up.

So here is the warning to tech founders, investors, accelerators, and anyone currently describing a perfectly nice niche product as “the future operating layer of the independent economy”:

Be careful what you call growth.

If growth means making the product better, wonderful.

If growth means serving more people without making life worse for the people who trusted you first, excellent.

But if growth means trapping customers in closed systems, bloating simple tools into mediocre platforms, and raising prices because leaving is more painful than staying, then you have not built innovation.

You have built a toll booth.

And eventually, people do not celebrate toll booths.

They find back roads.