AI Series Day 1 | 12 Days of AI. Stop Overthinking ChatGPT: Free vs. $20? Here's What ACTUALLY Matters for Founders

Are you spinning in circles trying to figure out if ChatGPT Plus is worth the $20? 

Let’s cut through the tech noise and make a clear, founder-focused call right now.

In Day 1 of the 12 Days of AI Quick Wins, Dawn breaks down the only AI question that really matters for founders: Do you stick with the free ChatGPT or level up to Plus? If you’ve been stalling on getting started with AI or wondering why the paid version even exists this quick-hit episode gives you the clarity (and permission) you need. No FOMO. No fluff. Just strategic direction.

Your Day 1 Action:
Head to chat.openai.com, sign up for the free version, and ask it one real business question. Try:
- “What should I focus on this week?”
- “Help me write an email to my team about [insert your topic].”
Start the conversation. You don’t need fancy—you need forward motion.

Key Takeaways:

• Free is powerful. GPT-3.5 is enough for 80% of early-stage AI use like rewriting, brainstorming, and summarizing.
• Upgrade only when… you’re uploading files, building workflows, or need real-time insights.
• Don’t pay until it pays off. Use the free version to master your prompting game first.
• The $20 decision is not a tech decision—it’s a business one. Choose based on your workflow, not the hype.
• Clarity over complexity. Skip the spiral. Start simple.

Resources & Links:

•  Get the 12 Days of AI Quick Wins Toolkit – just $7
•  Register FREE for Day 13’s Live AI Implementation Party – Win a 90-min Strategy Intensive

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Transcript

She's That Founder
AI Series Day 1 | 12 Days of AI. Stop Overthinking ChatGPT: Free vs. $20? Here's What ACTUALLY Matters for Founders

Hey, founder friends, you're hearing everybody talking about ChatGPT. I'm sure you're over it and here's the thing, some people are paying $20 a month, some are using the free version, some are using other tools, and you're sitting there thinking, do I even need this? And if I do, which thing do I need? 

Well, let me save you the spiral. In five minutes, you'll know exactly which AI tool to use and why.

Hey, hey, hey. Welcome to She's That founder, the show that helps ambitious female founders stop drowning in decisions and start owning their CEO seat with a little AI magic. I'm Dawn Andrews, and this is day one of the 12 days of AI. A Female Founder's holiday business intervention series.

Today's topic, total clarity on free versus paid AI. No guilt, no FOMO. Just a decision you can make and move on. 

Real talk. Most founders I work with are either using chatgpt free version and getting really frustrated, or they upgraded to plus, but they don't know why and they don't know what to do with it.

Here's the breakdown. ChatGPT free, the 3.5 version. It is solid for rewriting, emails, brainstorming, summarizing text, giving you first drafts of things. It's fast, it's free, and honestly, for a lot of folks, it's 80% of what you'll need to do. Starting out. The catch is, it does not remember context well between conversations. Doesn't really have instructions or a memory and it can't analyze files or access real-time information. It's just a really basic and thorough large language model. And the 3.5 version in a private account also may be scraping your data and using it to train the model. 

ChatGPT plus, which is version four and up. And right now chatGPT is on version 5.1. As of this recording is $20 a month. You get smarter responses. You get document upload and analysis. You can build custom GPTs, you can browse the internet through Atlas. You can generate images. 

So which one do you need? 

You have to ask yourself what you're doing in your business. I would say start with free. Seriously, especially if you've been a little sketchy about AI. Then upgrade to plus, when you hit one of these situations, I'm gonna give you two that are big in my business and big with all of my clients. 

So situation one, you want to upload files for analysis, like you wanna upload your bookkeeper spreadsheet and ask What's eating at my margins? It'll find the answer in 30 seconds. And free chatGPT does not open files. Or if you wanna review all of your social posts for the year and see which ones are most effective. I recently uploaded all of my podcast data and had it break down for me where I should be focusing my energy and attention.

So, situation two for chatGPT paid is if you wanna build a brand voice GPT that will write for you in 60 seconds, mimicking your exact phrases, your voice, your tone, your style, your edge. And you don't need to re-explain yourself or your strategy or your ideal client or any other brand details every single time. So if you're just starting, free is fine. Get comfortable using ai. Learn how to write good prompts, and then upgrade when you're ready.

So quick recap, chatGPT, free start there. Basics, covered chat, GPT plus $20 a month. Upgrade when you're analyzing files, when you're building workflows, when you wanna mimic your particular leadership voice or if you need to access current info, here's the main thing though, don't overthink it.

Just pick one and actually use it.

So here's your day one action in the next 10 minutes. Go to chat.openai.com. Sign up for free if you haven't, and ask it one business question, what should I focus on this week? And see what happens. 

And if it's not a satisfactory answer, then it's time to upgrade or ask it. "Help me write an email to my team about whatever the thing is." Just start the conversation.

If you wanna grab the complete 12 days of ai, quick wins toolkit. All the prompts, the templates, the workflows in one guide, go to hellodawn.live/day13 , and you can grab the whole thing for just seven books.

And day 13 is our live implementation party where we wire all these workflows into your actual business. And I'm also giving away a 90 minute AI strategy intensive. So go register for free at hellodawn.live/day13. The links in the show notes.

See you tomorrow for another holiday gift.

Grab the 12 days of AI Quick wins toolkit, all the prompts, the templates, the workflows in one guide at hellodawn.live/day13 for just $7. 

Day 13 of this giveaway is our live AI implementation party where we'll wire these workflows into your actual business, and I'm giving away a 90 minute AI strategy intensive. Register free at hellodawn.live/day13.