By Mark Mason. October 20, 2026. With the video (16:38), chapters, and the full transcript below.
If you run a business and you’re paying about $20 a month for AI, the best AI subscription is usually the one you already use. If you’re on ChatGPT or Claude and you’re getting value from it, stay there, because switching has a real cost. If your business runs on Google (Gmail, Google Docs, Google Sheets) and you already use Gemini, stay there too. And if you’re asking what I’d pick with my own $20, it’s Claude, every time. I’m biased: I use it every day.
But which one you pick matters a lot less than how you use it. Most people are only using about 10% of what they’re paying for, because they use AI like a search engine. The big unlock is getting it to do the work instead of answering questions. Below: my verdict, two real examples from my wife’s photography business, my honest take on Copilot, and when the $100 or $200 plan is worth it.
Watch the video
Best AI Subscription for Business Owners (I Pay for All of Them) (16:38)
- 0:00 Best AI subscription for business owners
- 0:53 AI for business: you don’t need to be an expert
- 2:13 ChatGPT vs Claude vs Gemini: my verdict
- 4:53 AI for small business: make it do the work
- 11:28 Is Microsoft Copilot worth it?
- 12:23 Is the $20 ChatGPT or Claude plan enough?
- 13:28 Does it matter which AI model you pick?
- 14:45 Which AI subscription to keep: the bottom line
Prices checked October 19, 2026: ChatGPT Plus, Claude Pro and Google AI Pro are about 20amonth(19.99 for Google). The bigger plans (Claude Max, ChatGPT Pro, Google AI Ultra) run $100 to $200 a month. Check the current price before you buy.
Do you need to be an AI expert to choose an AI subscription?
In the video: 0:53
No. You don’t want to be an AI expert. You’re trying to run a business. Meanwhile you hear people talking all the time about the magic of AI: everything is possible, you can sit on a beach somewhere and let AI run your business. So you wonder whether you’re missing out. And if you’re already spending $20, $100 or $200 a month, you wonder whether it’s the right plan, and exactly where your money should go.
I get it. Here’s where I’m coming from. I lead engineering teams, including AI engineering, at a Fortune 500 semiconductor company. In my own businesses I use AI from all kinds of providers, all the time, and I pay for it with my own money:
- Two ChatGPT accounts
- Claude’s top plan (Max)
- Gemini’s entry plan
- OpenRouter, which lets me test all kinds of other models
So here’s what I spend my own money on to run my businesses and my wife’s business, how I’d decide which AI you should pay for, and, more important, how to get the most value out of the money you’re already spending.
ChatGPT vs Claude vs Gemini: which $20 plan should you keep?
In the video: 2:13
I’ve worked in corporate America for more than 35 years, and most of the executives I know want the bottom line up front. You probably do too. So here it is:
- If you already use ChatGPT or Claude, stay right there.
- If you’re heavily invested in Google (Gmail, Google Docs, Google Sheets, all the Google tools) and you already use Gemini, stay there too.
- If you’re asking what I’d pick for $20 a month: give me Anthropic and Claude, every time. It’s my favorite tool.
If you’re attached to ChatGPT, it’s a very close second. But my personal opinion is that the best tool for small business owners today is Claude. I use Claude and Anthropic’s tools every single day: in my corporate life, my personal life, my own business, and my wife’s business. I think it’s the best value, especially at the $20 level. It’s a biased recommendation, and it’s still my recommendation.
What each one is good at
None of these tools is good at everything, but they’re all pretty good at most things.
- Claude is very, very good at writing, and very, very good at controlling your computer.
- ChatGPT wasn’t as good at controlling your computer six months ago. Since then OpenAI has released a new model that’s fantastic at it. These companies keep leapfrogging each other.
- Images are the one thing Claude still doesn’t do very well, and I need them often. That’s why I pay for ChatGPT in addition to Claude: I like the images ChatGPT creates. I actually have it set up so that when Claude needs an image, it asks ChatGPT to make it. Gemini is really good at images too, and sometimes I use it for that.
Switching has a real cost
Here’s what most people ignore. If you’re already using ChatGPT, you’re happy with it, and you’re getting value, stay there. Read the rest of this post on how to get more out of it first, and if you’re still comfortable with what you’re using, don’t switch.
If you’ve used a tool for a month, six months or a year, it has a lot of context about you and your business, and that context is what makes these tools powerful in the first place. There are ways to transfer it, but starting over has a cost. Don’t ignore that.
How do you get AI to do the work, not just answer questions?
In the video: 4:53
So why aren’t you getting the value out of these tools that you could be? Most people in small business use AI as a glorified search engine, a smart helper. They need to write a document, so they ask, “Will you research this for me?” Or even better, “Will you write this for me?” That’s asking Claude or ChatGPT to answer questions for you, sometimes in the form of a work product you copy out of the chat window and paste into a Word document.
When this all started almost three years ago, that’s exactly where I started. If that’s where you are, that’s fine. But the big unlock is a shift in mindset: from AI as a tool that helps you learn about things or know things, to AI as a tool that actually does things. There’s a big difference between AI handing you raw data, information, or an almost finished work product, and AI actually doing the work.
Here are two examples from my wife’s business.
Example 1: blog posts drafted from her social media posts
My wife, Paula, is a popular local photographer in our hometown. She does family portraits and senior pictures. Like every photographer, she needs clients, and like every business owner, she needs clients coming from Google search and AI search. That generally comes from a presence on the web: blog posts and other search-optimized content.
Writing blog posts is not her favorite thing. She’s busy taking pictures and editing them, and few people appreciate how much work a photographer does after the picture is taken: managing clients, talking to them on the phone, helping them with their photo orders. She just doesn’t have a lot of time to write blog posts.
So here’s what we set up. It goes past creating information for a blog post to actually creating the post:
- Claude watches her social media accounts, specifically Facebook and Instagram.
- When she posts about a photo shoot she just did, it takes the image and the caption and analyzes them.
- Using what we’ve told it about Paula’s business, her voice, and our marketing goals, it writes a draft blog post in her voice, using the image.
- It pushes that draft into WordPress automatically, as a draft post for review.
- It emails her to say it just created a draft blog post from her post, with a link to review and edit it.
She makes some edits, and that’s great, because it takes the content to an even higher level. The truth is, if that draft hadn’t been created, Paula might never have gotten around to it.
That’s the magic. The old way, you type, “ChatGPT, would you please draft a blog post for me based on this thing I just did?” That needs you, the user, to start it. The new way, Claude or ChatGPT comes to you: “My job is to create draft blog posts for you. I noticed you created some content. I’ve repurposed it, and it’s waiting for you to approve and publish. You don’t have to copy and paste it. It’s already on the blog.”
I like to think of that as giving Claude or ChatGPT hands: connectors it can use to reach into the tools you use every day and do that work for you. That’s the huge unlock. Move from using AI as a tool that puts a bunch of words on the screen, which you then copy and paste into a work product, to using it as a worker that creates the final result, or the result that needs your approval, your human touch, the special thing only you can do. Not only does it do the work, it keeps you accountable on a cadence for things like blog posts or invoices, whatever your business needs.
Example 2: quarterly sales tax
Paula’s business has to file quarterly sales tax. I get that job, because I’m the business helper guy in our business. I hate filing quarterly sales tax, and I don’t do it anymore. Claude does.
Every quarter, Claude:
- Gets all the sales data and downloads it.
- Sums it up and computes the sales tax we owe.
- Opens the state website and puts the numbers in.
- Writes everything we’re telling the state into the spreadsheet where we keep our records.
- Documents all the evidence.
- Notifies me that it’s time to verify those numbers and push the button.
I used to pencil it in on my calendar and go figure it all out myself. Now I see an email, log in to the website, check the numbers, and push the button to send in our state sales tax. Claude does the work, and I verify it before anything is filed. That’s a huge unlock for our business.
Is Microsoft Copilot worth it for a small business?
In the video: 11:28
Microsoft is ingrained everywhere, especially across corporate America, so Copilot is worth a mention. Honestly: I don’t love Copilot, I don’t use it very much, and so I’m not an expert on it. If you do love it, more power to you. Tell me in the comments on the video what you like about it and what I’m missing.
Personally, I feel like Microsoft is behind, which is hard for me to imagine. I’d like to do some experiments with Copilot, and your input would help me a lot.
That said, don’t switch off Copilot just because I don’t like it. If it’s working for you, keep going with it. One thing I’m sure of: a year from now, all of these foundational models will be plenty good for whatever you need them for.
Is the $20 ChatGPT or Claude plan enough?
In the video: 12:23
Yes. The question I get a lot is what size plan to pay for, and the answer is that the $20 plan for Claude and the $20 plan for ChatGPT are plenty good enough for almost everyone to start. Claude has a $20 plan, a $100 plan and a $200 plan. Start on the $20 plan: it unlocks almost every feature you’re ever going to need. The bigger plans mostly buy you more use.
| Plan | Price a month |
|---|---|
| ChatGPT Plus | $20 |
| Claude Pro | $20 |
| Google AI Pro | $19.99 |
| Claude Max, ChatGPT Pro, Google AI Ultra | $100 to $200 |
Prices checked October 19, 2026. They change often, so check the current price before you buy.
When is the $100 or $200 plan worth it?
It’s a return on investment question, and the software will tell you when to ask it. If you’re getting value out of AI, you keep running up against your limits, you’ve got more work to do, and you know a few more AI credits would get a bunch more work done, it will be obvious whether to spend more.
Then do the math. Going from $20 to $100 is another $80 a month. Can you get at least $80 of value out of it? In most cases that’s easy: one more customer or sale, or saving an hour or two in your business, pays for it. If you’re getting a return on your investment, spend the money on the bigger plan. But until the software is complaining that you’re running out, stay on the $20 plan.
Does it matter which AI model you pick?
In the video: 13:28
Less than it used to. A year ago, I felt it was really important to pick the right AI model for your situation. Things have changed, and I don’t feel that way now.
Use whatever you want. One of my very, very good friends uses ChatGPT every day, he would never consider switching to Claude, and that’s perfectly fine. As these AI models get better and better, their minimum capabilities are going to be far above what you need to run your business. It’s not going to matter which one you use. They’ll all be fine for your use case, and that’s coming sooner than you might think.
So try to ignore the AI bro FOMO videos on YouTube: “This model is incredible. You must try this or you’re missing out.” That’s not for you. You’re running a business, and you’re trying to get stuff done. AI is just another tool in your toolbox, like your computer, a typewriter or a pencil. If you’ve got a landscape business, it’s like a lawnmower. It needs to be good enough to do the job and cost effective. That’s all you care about.
What’s the bottom line on which AI subscription to keep?
In the video: 14:45
Most people today use AI like a search engine: tell me about this, what do you think about that, help me write this paragraph. Not you. You’re going to invest in AI so it actually does things for you. The way to do that is a tool like ChatGPT Work or Claude Cowork. (OpenAI launched ChatGPT Work in July 2026 to close the gap with Anthropic’s Claude Cowork.) Connect it to your tools and have it get things done.
It really doesn’t matter exactly which one you use. What matters is that you use it to actually get things done. Right now, 90% of people are getting 10% of the value out of AI. Making it do the work puts you among the 10% who get 90% of the value.
One last thing. Paula’s secret is that she tweaks her blog drafts to leave a little bit of Paula in every post, because she doesn’t want AI slop in her business. That’s what next week’s video is about: in a world where everyone has AI, what do you need to be doing as a business owner to make sure your business is uniquely yours?
Sources
- Louis Corneloup, “Claude Pro vs Max 2026: Which Plan Is Worth the Price?”, Dupple, October 14, 2026. Claude Pro is $20 a month billed monthly; Claude Max is $100 or $200 a month.
- Krater, “ChatGPT Pricing 2026: Free, Go, Plus, Pro and Business Explained”. ChatGPT Plus is $20 a month; ChatGPT Pro comes in $100 and $200 tiers.
- Anna Washenko, “The Google AI Ultra plan now starts at $100 a month”, Engadget, May 19, 2026.
- Matthias Bastian, “Google overhauls its AI subscriptions at I/O 2026 with three tiers starting at $10 a month”, The Decoder, May 19, 2026. Google AI Pro is $19.99 a month; Google AI Ultra starts at $99.99.
- Larry Dignan, “OpenAI launches ChatGPT Work, rolls out GPT-5.6 model family”, Constellation Research, July 9, 2026.
- All prices checked October 19, 2026.
About Mark Mason
Mark Mason leads engineering teams, including AI engineering, at a Fortune 500 semiconductor company. He has run online businesses since 2007 and has been podcasting since 2009. His YouTube channel, @MarkMasonCom, is practical AI for the business you already run: growth by design, not by grind.
Full transcript
The video’s words as spoken, lightly punctuated. Chapter times match the video.
Best AI subscription for business owners (0:00)
If you’re a business owner and you’re paying $20 a month for ChatGPT, and you’re sitting there hearing all the hype, wondering if you should be paying more for the higher level subscription, or switching to Claude so you can take advantage of Claude Cowork, or maybe switch to Gemini, or find out what Grok bot is about, listen, I totally get it. I run AI engineering teams for a living, but the truth of the matter is you already have everything that you need to be successful in your business with the AI that you’ve already got. The challenge is you’re only using 10% of what you’re paying for, and that stops today. We’re going to demystify all this stuff about what you should be buying and make sure that you’re getting the value out of the tools that you’re already paying for.
AI for business: you don’t need to be an expert (0:53)
So I get it. I understand exactly where you’re coming from. You don’t want to be an AI expert. You’re trying to run a business, and you hear people all the time talking about the magic of AI and all the value that they’re getting out of it, how everything is possible with AI, and you can just sit on a beach somewhere and let AI run your business and you don’t have to do a thing, and you’re wondering whether or not you’re missing out. I totally get that.
And not only that, if you are spending $20 or $100 or $200, you’re wondering if it’s the right $100 or $200, and exactly where your money should go. I get that too.
In my business, I’m actually using AI from all different kinds of providers all the time. I pay for routers that let me test all different kinds of models. I pay for the maximum Claude subscription. So I thought today what we could do is I could talk to you about what I spend my own personal money on to run my own personal businesses and my wife’s business, and how I can help you decide which AI you should be spending your money on, and more importantly than that, how to get the maximum value out of the money that you are spending on AI. Sound good? All right, let’s go.
ChatGPT vs Claude vs Gemini: my verdict (2:13)
I’ve been working in corporate America for more than 35 years, and most of the executives that I know want the bottom line up front, and I know that you probably do too. So here it is. If you’re already using ChatGPT or Claude, I would absolutely just stay right there. And if you’re heavily invested in the Google infrastructure, you use Gmail, Google Docs, Google Sheets and all of those Google tools, and you already use Gemini, I’d stay right there too.
For $20 a month, give me Anthropic and Claude every time. It’s my favorite tool. If you’re attached to ChatGPT, that’s a very close second, but my personal opinion is that the best tool for small business owners today is Claude. I literally use Claude and Anthropic tools every single day, in my corporate life, in my personal life, in my personal business, in my wife’s business. And I’ll tell you, I think it’s the best value, especially at the $20 a month level.
Now, one thing I’ll say is that all of these tools aren’t good at all the things. I think they’re all pretty good at most things. I would say Claude is very, very good at writing things, and it’s very, very good at controlling your computer. ChatGPT wasn’t as good at controlling your computer six months ago. It couldn’t even do it at all. And now they’ve just released a new model that’s fantastic at it. So these companies are leapfrogging each other. The one thing that Claude still doesn’t do very well that I need to do quite often is actually generate images. And so that’s why I pay for ChatGPT in addition to Claude, because I like the images that ChatGPT creates.
Here’s the thing that most people ignore. Switching has a real cost. So again, if you’re already using ChatGPT and you’re happy with that and you’re getting value, and after you hear from me about the ways that you should be getting value from these tools later in this video, if you’re comfortable with what you’re using, stay there, because there’s an opportunity cost involved with switching. The fact that you’ve been using a particular tool for a month or six months or a year means that tool has a lot of context about you and your business, which is what makes these tools really powerful to begin with. And while there are ways to transfer that information, starting over has a cost, and I don’t want you to ignore that.
AI for small business: make it do the work (4:53)
So the question is, why aren’t you getting the value out of these models that you could be? And the truth is, most people are using AI in small business as a glorified search engine, smart helper. They need to write a piece of document, so they say, “Hey, will you go ahead and research this for me?” Or even better, “Will you write this for me?” That’s really asking Claude or ChatGPT to answer questions for you, sometimes in the form of a work product that you can actually copy from the Claude window and paste into a Word document.
Literally, when this all started almost three years ago, that is exactly where I started. And if you’re there too, that’s fantastic. But here’s the thing. The big unlock is when you shift your mindset from using AI as a tool that can help you learn about things or know things to a tool that can actually do things. There’s a lot of difference between giving you raw data and information and things that are almost finished work products, and using AI as a tool that can actually do things.
Now, let me give you a concrete example from my actual life and my wife’s business. My wife is a very popular local photographer in our hometown. She does family portraits and senior pictures, and what does she need? Like all photographers, she needs clients. And like all business owners, my wife also needs clients coming from Google search and AI search. And where that comes from generally is from website presence, like blog posts and other search engine optimized content.
Creating blog posts is just simply not my wife’s favorite thing. After all, she’s really busy taking pictures and editing them. No one really appreciates how much work photographers have to do after the picture is taken: managing clients, talking to them on the telephone, helping them with their photo orders and so forth. She just doesn’t have a lot of time to write blog posts.
So here’s what we did that took us from this idea of creating information that could be used for blog posts to actually creating the post. We asked Claude to watch her social media accounts, specifically her Facebook and Instagram accounts. And whenever it saw a post that she did about a photo shoot she had just done, it observes that post, takes the image and the caption, analyzes it based on what’s in there, and then, using information that we’ve told it about Paula’s business and her voice and the objectives that we want to achieve from a marketing standpoint, it actually takes that information and creates a draft blog post. It uses the image, and it actually writes a draft blog post in her voice based on the event that she’s already posted in social media. And then it pushes that content automatically into WordPress as a draft post for a review. And it sends her an email and says, “Hey, I just created a draft blog post based on this. Here’s the link to go review it and edit it.” She’ll make some edits, and that’s great, because that takes the content to an even higher level.
The truth of the matter is, if that draft blog post had not been created, Paula might not have ever gotten around to it. And that’s the magic of actually changing from typing at the computer, “Hey, ChatGPT, would you please draft a blog post for me based on this thing I just did?” That requires an initiating action from you, the user, to a different, totally different kind of scenario, where ChatGPT or Claude actually notifies you that, “Hey, my job is to create draft blog posts for you. I noticed that you created some content. I’ve repurposed it, and it’s out there waiting for you to approve and publish. You don’t have to copy and paste it. It’s already on the blog.”
That’s an idea I like to think of as giving Claude or ChatGPT hands, these connectors that it can use to reach into the tools that you normally do to do your work every day, and actually do that work for you. That’s the huge unlock that I want you to take away from this video. Move from using ChatGPT or Claude as a tool that creates a bunch of words on the screen that you have to then copy and paste and do something with to create a work product. Change from that to using Claude or ChatGPT as a worker who does that content creation, or whatever it is, and creates the final result for you, or the final result that needs human approval, or that human touch, or the special thing that only you can do. That’s a huge shift, because not only does it do the work for you, it keeps you accountable on a cadence to do things like blog posts or invoices or whatever it is that you need to do in your business.
Another quick example is Paula has to file quarterly sales tax. I get to do that job because I’m the business helper guy in our business. I hate filing quarterly sales tax. I don’t do that anymore. Claude does that for me. And that’s just another example. Every quarter, Claude wakes up and says, “Hey, I’m going to go get all the sales data. I’m going to download the data. I’m going to sum it up. I’m going to compute the sales tax we owe. I’m going to open the state website. I’m going to put the numbers in there. I’m going to write in our spreadsheet that we keep a record of everything that we’re telling the state, document all the evidence,” and then notify Mark that it’s time to verify those numbers and push the button. That’s a huge unlock for me, having to pencil in on my calendar that I need to go figure all this stuff out, to seeing an email, logging in to the website, and pushing the button to send in our state sales tax. Huge unlock for our business.
Is Microsoft Copilot worth it? (11:28)
I thought I’d also talk a little bit about Copilot, because Microsoft is so ingrained everywhere, across especially corporate America. It’s worth a mention. I don’t love Copilot, and I don’t use it very much, and therefore I am not an expert on Copilot. But if you do love it, more power to you, and let me know in the comments what it is that you like about it and what I’m missing with Copilot. Personally, I feel like Microsoft is behind, which is hard for me to imagine. I’d like to actually do some experiments with Copilot, and input from you would help me out a lot.
That said, don’t change off of Copilot just because I don’t like it. If it’s working for you, keep going with Copilot, because one thing I’m sure of is that a year from now, all of these foundational models are going to be plenty good for whatever you need them for.
Is the $20 ChatGPT or Claude plan enough? (12:23)
So one question I get a lot is, what size plan should I be paying for? Is the $20 plan good enough? And the answer is absolutely yes. The $20 plan for Claude, the $20 plan for ChatGPT, they’re plenty good enough for almost everyone to start.
And let me tell you, if you’re getting value out of AI, and you recognize that you’re running up against your limits, and you’ve got more work to do, and you’re excited about the fact that if you just had a few more AI credits, that you could get a bunch more work done, it will immediately be obvious to you whether or not you should spend more money on AI. This is just a return on investment question. So don’t worry about the fact that Claude has a $20 plan, a $100 plan and a $200 plan. Just start on the $20 plan that unlocks almost all of every feature you’re ever going to need. The thing on AI is it’s all about return on investment. If you’re getting return on your investment, you should spend the money on the bigger plan.
Does it matter which AI model you pick? (13:28)
You know, a year ago, I felt it was really important to pick the right AI model for your particular situation. And now, things have changed, and I don’t feel that way. You use whatever you want. One of my very, very good friends uses ChatGPT every day, and he would never consider switching to Claude, and that’s perfectly fine. And the reason it’s perfectly fine is because as all of these AI models get better and better, most of them, their minimum capabilities are going to be far above what you need to run your business. And so it’s not going to matter which one you use. They’re all going to be fine for your particular use case.
So try to ignore all of the AI bro FOMO YouTube videos. “This model is incredible. You must try this or you’re missing out.” That’s not for you. Remember, you’re running a business. You’re trying to get stuff done. AI is just another tool in your toolbox, like your computer or a typewriter or a pencil. If you’ve got a landscape business, it’s like a lawnmower. It’s just something that you’re using to get work done in your business. It just needs to be good enough to do the job and cost effective. That’s all you care about.
Which AI subscription to keep: the bottom line (14:45)
So here’s the bottom line. Most people today are using AI like a search engine. “Tell me about this. What do you think about that? Help me create this paragraph of text.” But not you. You are going to make sure that you’re investing in AI so that you can unlock the potential of having AI actually do things for you. The way you do that is you invest in a tool like ChatGPT Work or Claude Cowork, and you actually have it do things for you. Connect it to your tools, get things done. It really doesn’t matter exactly which one you use. What matters is that you use it to actually get things done. That’s the big unlock that takes you to where 90% of the people are getting 10% of the value, and it makes you one of the 10% of the people that are getting 90% of the value out of AI.
Now, I told you that one of Paula’s secret unlocks is that she tweaks her blog posts to leave a little bit of Paula in every post, because she doesn’t want AI slop in her business. And so, in next week’s video, we’re going to talk about that very thing. In a world where everyone has AI, what do you need to be doing as a business owner to make sure that your business is uniquely yours? Until next time, I’m Mark Mason. It’s been great talking to you. Talk to you soon.



