The three big AI assistants all land at the same price now. ChatGPT Plus is $20 a month. Claude Pro is $20. Google AI Pro is $19.99. That is $240 a year, which is less than most of us spend on coffee for the office.
I get asked the same question at almost every session. "Is the paid version actually different, or is it just the free one with a nicer logo?" It is different. The free tiers are fine for a quick question. The paid tier gets you the better models, a lot more usage before it cuts you off, the ability to upload files, and a place to keep your business context so you stop re-explaining yourself every time. Those four things are what make it a tool you run a business with instead of a toy you poke at.
Here are ten things I would actually do with it. Every one of these can be done today, by a person with no technical background, with nothing more than the subscription and a web browser. I am not selling any of these products. I do not get a dime from any of them. Pick whichever one you will actually open in the morning.
1. Write the thing you have been putting off
Every business owner has one. The proposal that has been sitting half-done for a month. The employee handbook. The email to the client who is 60 days late. The reason it is not done is not that you cannot write. It is that a blank page at 9pm after a full day is brutal.
Open the tool. Talk into it. Say what you want to say the way you would say it to a friend. "I need to tell this client that the delay was on their side, that I still want to work with them, and that the new date is the 30th." You will get a draft in ten seconds. It will not be perfect. It will be 80 percent, and fixing 80 percent is easy.
One tip that changes everything: paste in two or three things you have written before and say "write it the way I write." It will pick up your voice. The default voice sounds like a corporate press release. Yours does not, and it should not.
2. Read the thing you do not have time to read
Upload the lease. Upload the vendor contract. Upload the 40-page grant application packet with the eligibility rules buried on page 23. Then ask it plain questions. "What am I agreeing to here?" "What happens if I want out early?" "Is there anything in this that a small business should push back on?"
This is the single biggest jump from the free tier. File upload is a paid feature on most of these, and it turns the tool from a chatbot into something that reads for you.
It is not your lawyer. Do not treat it like one. But you will walk into the meeting with your lawyer knowing which three questions to ask, and that cuts a two-hour bill to a thirty-minute one.
3. Get an argument instead of a cheerleader
These tools want to agree with you. That is a known problem, and it is dangerous if you are using one to make decisions. So do not ask "is this a good idea." Ask it to argue the other side.
"I am thinking about raising my rates 15 percent in January. Give me the strongest case against doing that." You will get objections you had not considered, and some you had considered and were hoping to skip past. Then ask for the case in favor. Then decide. You are still the one deciding. You just get to decide with the other side of the table already argued.
I do this before every significant decision now. It is the cheapest consultant I have ever hired.
4. Make the spreadsheet make sense
Export your sales from Square, or your transactions from QuickBooks, or whatever you use. Upload the file. Ask "what is going on in here?"
It will tell you that Tuesdays are dead, that one customer is a third of your revenue, that your best month was the one you thought was your worst. It will build you a chart if you ask. It will write the formula you have been fighting with in Excel. It will tell you what the formula you already have actually does, which is sometimes the more useful answer.
You do not need to know what a pivot table is. You need to know what question you are trying to answer.
5. Turn talking into documents
I dictate almost everything I write. That includes this. The paid tiers have voice modes and the phones have speech-to-text built in, and the combination means you can walk around your shop, describe how you do something, and end up with a written procedure at the end.
"Here is how we open in the morning. First we..." Ten minutes of talking. Then: "turn that into a checklist a new employee could follow." You have just written the training document you have been meaning to write for three years. You did it in the car.
This is how you get the business out of your head and onto paper. Nobody has time to sit down and type it. Everybody has time to talk.
6. Answer the customer faster and better
Most of what customers ask, they have asked before. Set up a project (all three tools have some version of this) and put your standard answers in it. Your pricing. Your policies. Your hours. What you do and do not do. Then when the message comes in, paste it and say "draft a reply."
Same thing for reviews. A bad review at 11pm is not the time to write from the gut. Paste it in and ask for a reply that is calm, takes responsibility where it is due, and does not grovel. Read it in the morning. Send it or fix it.
You still read every reply before it goes out. That does not change. What changes is that you are editing instead of composing, and editing is five times faster.
7. Do the research you keep meaning to do
The paid tiers have research modes that go out, read dozens of pages, and come back with a report. This is not the same as asking a question and getting a paragraph. It takes a few minutes and it actually looks things up.
"Who else in central Ohio does what I do, what do they charge, and what do their reviews complain about?" "What licenses does a mobile food business need in Franklin County?" "What changed in the rules for this grant program in the last year?"
Check the sources. It will give you links. Click a few. It is right most of the time and confidently wrong some of the time, and the only way to know which is to look. But an hour of your Saturday just became fifteen minutes.
8. Hire without guessing
Write the job posting. Then ask it to write ten interview questions and tell you what a good answer sounds like versus a bad one. Then, after the interviews, paste in your notes and ask it what you might be missing.
Most small business owners have hired maybe a dozen people in their life. There is no way to get good at something you do a dozen times. This gets you a structure that a 500-person company's HR department would have handed you, without the HR department.
9. Stop starting from zero every time
This is the feature that makes the $20 worth it on its own, and it is the one nobody explains well.
Every paid tier lets you set up something like a project or a workspace. Put your business in there. What you do. Who your customers are. How you talk. Your price list. Your logo files. Your last three proposals. Then every conversation inside that project already knows all of it.
Without this, you spend the first five minutes of every chat explaining who you are. With it, you open a new chat and say "write the October newsletter" and it already knows what you sell, what last month's newsletter said, and that you never use exclamation points. Set it up once. It takes an hour. It pays you back every day after.
10. Get unstuck at 9pm
You are in QuickBooks and something is wrong with the invoice and you do not know what. Take a screenshot. Paste it in. Say "what is happening here and how do I fix it."
Same for Canva. Same for Square. Same for the Google Workspace settings you have never touched. Same for the printer. The tool has read every help article and every forum thread for every piece of software you use, and it does not mind that you asked the same thing last week. This is a live, patient tech support line for $20 a month, and it covers everything, not just the one product.
The part about privacy
You are going to paste things into this that you would not put on a billboard. That is fine. That is how it becomes useful. A few rules that are actually narrow:
Never paste a password. Never paste a full credit card number, a Social Security number, or a bank account number. There is no good reason to, and there is never a good outcome.
For everything else, the question is whose information it is. Your own numbers, your own plans, your own drafts: paste away. Other people's information, like a client's contract or an employee's file: get their okay first, and make it a normal part of how you work. "We use AI tools to draft and review documents" in your engagement letter handles most of it. Most clients say yes without a second thought, because the alternative is paying you three times as much to do it the slow way.
One setting to check the day you sign up: every one of these tools has an option for whether your conversations are used to train their models. Find it. Turn it off. It takes a minute.
If the $240 is the problem
That is exactly what the fAIr Advantage Fund is for. The application is four questions. If you are a woman- or minority-owned small business in Ohio and a year of one of these subscriptions is the thing standing between you and doing any of the ten things above, apply. We pay the vendor directly for the year. You do not fill out a grant proposal. You answer four questions and tell us what it would change.
And come to a session. They are free, they are monthly, and the second half of every one is just questions. Bring the contract you cannot read. Bring the spreadsheet that does not make sense. That is what the hour is for.