What I Learned From Reading 100 Small Business Questions on Reddit

The numbers show the scale. Reddit reveals the problem.

I ended the previous article with this line:

The numbers show the scale. People reveal the problem.

It sounded like a closing sentence.

In practice, it became the beginning of the next piece of research.

Over the past few months, I have been collecting data on how small businesses are adopting AI.

The numbers tell a clear story.

In 2025, 58% of small businesses in the United States reported using generative AI, compared with 40% a year earlier and 23% in 2023.

Another study found that 76% of small businesses are already using AI or exploring how they might use it.

AI is no longer a future idea for small businesses.

It is already here.

But the more data I read, the more I felt it left one question unanswered:

If so many business owners are already using AI, why do so many of them still not feel that it is truly helping them run the business?

In a survey by Reimagine Main Street and PayPal, more than half of the businesses were classified as "Explorers" - owners who are experimenting with AI but have not yet fully integrated it.

Seventy-four percent said they would adopt more AI if the financial value were clearer. Seventy-three percent wanted tools that were easier to use.

They are not necessarily opposed to AI.

But many of them are still unsure what, exactly, to do with it.

To understand that gap, I turned somewhere entirely different.

Reddit.

Not to read what AI companies say business owners need.

To read how business owners describe what is bothering them when they talk to one another.

One hundred questions. Only nine of them started with AI.

I collected a manual sample of 100 questions and discussions from communities for small business owners, solopreneurs, consultants, freelancers, agency owners, and other professionals.

This was not an academic study or a representative sample. It was not designed to tell us what every small business owner thinks.

But it was broad enough to reveal patterns.

Only nine of the 100 questions began directly with AI.

The others were about things like:

• How do I get customers?
• How much should I charge?
• How do I know what to focus on this week?
• How do I stop leads from slipping through the cracks?
• How do I know whether the business is actually profitable?
• How do I manage everything alone without burning out?

The topics that appeared most often were marketing, pricing, priorities, customer acquisition, bookkeeping, cash flow, lead follow-up, and business loneliness.

Business owners were not saying: I need a more advanced AI system.

They were saying:

• I do everything myself.
• I do not know what to focus on.
• I am afraid I have forgotten something.
• I work all day, but the business is not really moving forward.
• I do not know whether I am charging enough.
• I have no one to think this through with.

And that language changed several things I thought I understood.

I thought they mainly wanted automation. They talked far more about guidance.

It is easy to understand why the AI industry talks so much about automation.

Automation is easy to demonstrate.

A task that took an hour is completed in a minute. An email sends itself. A meeting schedules itself. A post writes itself.

But when business owners talked about what they were missing, many of them were not asking for another system to operate independently in the background.

They were asking for something more basic:

Tell me what matters now. Tell me what I should focus on this week. Tell me whether I am missing something.

They are not necessarily against automation.

But another system that needs to be configured, supervised, checked, and corrected when it makes a mistake is not always a relief. Sometimes it is simply another responsibility.

I spent a lot of time thinking about how much work AI could take off a business owner's plate.

The research made me think more about a different question:

How much uncertainty could it remove from it?

The fear that kept appearing was not necessarily a fear of AI.

It was the fear that something important would fall through the cracks. A customer who never received a reply. A lead that was forgotten. A cash flow problem developing quietly. Money being spent on the wrong marketing channel.

In that sense, business owners were not only looking for something to do the work.

They were also looking for a safety net.

I thought I would mainly find overload. Underneath it was the question of priorities.

I expected to find many stories about endless task lists.

I did.

But beneath the overload, another idea kept appearing:

I work all day, and the business is still not really moving forward.

This is not only a question of how much work there is.

It is a question of direction.

Small business owners are rarely short of tasks. In most cases, they have more tasks than they could ever complete.

What they lack is a way to distinguish between what is urgent, what appears important, and what could genuinely move the business forward.

In the sample, questions about focus, priorities, and the next step appeared repeatedly - far more often than the language the AI industry tends to use: automation, workflows, and agents.

That gap matters.

A system that generates more tasks does not necessarily help.

It may simply help a business owner do the wrong things faster.

AI has dramatically reduced the cost of execution.

It has not yet solved the problem of choosing.

I thought the main difficulty was doing everything alone. Thinking alone is also part of the burden.

What surprised me most was not only how much work business owners do by themselves.

It was how many thoughts and decisions they carry alone.

I make every decision myself. I have no one to talk this through with. I want someone to tell me whether I am missing something. I want someone to think with.

This loneliness does not always look like loneliness.

Sometimes it looks like procrastination. Sometimes it looks like constantly moving between tools. Sometimes it looks like another course, another consultant, another Google search. And sometimes it looks like a full day of work without a single decision that moves the business forward.

I thought small business owners mainly needed another pair of hands.

I realized that often, they also need another point of view.

Not someone to replace their judgment. Someone to help them avoid carrying it alone.

I thought category language mattered. People use different words.

I have spent a great deal of time thinking about the term AI Operating System.

I still think it describes the direction these products are moving in: a system that connects knowledge, work, memory, decisions, and areas of responsibility over time.

But almost no one on Reddit is asking for an AI Operating System.

The words that appear naturally are more human:

A team. A partner. An advisor. An assistant. A right hand. Someone to think with.

That does not mean the language of the vision is wrong.

It means it belongs at a different stage of the conversation.

We can think about the product in terms of operating systems, information layers, and coordinated agents.

But when speaking to the person we are building it for, it makes sense to begin with their words.

And their words usually do not describe technology. They describe the kind of support they are missing.

One thing became even clearer

Business owners do not trust AI blindly.

And their concerns are very specific:

• It will make things up.
• It will give generic advice.
• It does not know my business.
• I will have to double-check everything.

The problem, then, is not only whether the model is intelligent enough.

The problem is whether it understands who it is thinking for.

The same marketing advice can help one business and waste another business's budget. The same price can be too low for one consultant and impossible for another. The same task can be the most important thing to do this week - or a complete distraction.

Without context, AI can sound highly convincing while still having no idea what matters to the specific business.

The numbers and the people tell two parts of the same story

The statistics show that AI use among small businesses is growing quickly. They show interest, competitive pressure, and a willingness to experiment. They show that the adoption question is gradually shifting from "whether" to "how."

But the Reddit questions show that there is still a gap between use and value.

Business owners are not looking for AI simply for the sake of AI.

They are looking for a way to bring in customers. To price correctly. To understand the numbers. To know what to focus on. To notice something important before it becomes a problem. And to stop carrying the entire business alone inside their heads.

The numbers tell us that the market is moving.

People help us understand where it needs to move.

Because the opportunity is not simply to bring more AI into small businesses.

It is to build AI that begins with the small business itself. Its reality. Its constraints. Its decisions. And the questions the owner did not yet know they needed to ask.

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Sources

• U.S. Chamber of Commerce - Empowering Small Business: The Impact of Technology on U.S. Small Business, 2025
• Reimagine Main Street and PayPal - Small Businesses Look to AI for a Competitive Edge, 2025

Methodology note

The Reddit analysis was based on a manual qualitative sample of 100 question formulations drawn from public discussions in relevant communities. It was intended to identify recurring language patterns and business problems, not to statistically represent all small business owners.