The $100k executive assistant I hired for $20 a month

In my corporate days, all the big execs employed executive assistants. Last time I checked, the exec assistants earned upwards of $100k per year.

Nice work if you can get it. However, I’d a sneaking suspicion these exec assistants did the real work, while their bosses hopped in and out of Microsoft Teams calls in between boozy long lunches and golf games.

I liked the idea of having a right hand. So, when I quit the corporate racket and started my business, I hired my first assistant. We agreed on several hours a month. They worked on different projects, which I didn’t have time or energy to work on.

Thanks to their work, I found more time for other projects including writing a book, creating courses, and working half days to train for an Ironman in Spain. None of that would have been possible without some sweat equity.

I’m all for hiring to save time, as it’s the easiest way to grow a business. I regularly coach clients to do the same. Most solopreneurs and small business owners could do the help.

However, hiring an executive assistant will set you back several hundred to several thousand dollars a month, depending on where you hire and how much you need help with. Hiring is also expensive and risky. I’ve made some great hires over the years… and some bad ones.

One hire that’s currently working out?

ChatGPT as my new executive assistant.

It’s summarizing reading materials, giving me action points and creating daily To Do Lists. And it doesn’t take time off, get sick, or annoyed when I change priorities last minute.

ChatGPT is also taking care of mundane jobs like content repurposing and planning. ChatGPT is helping me track my goals for the year. And it’s planning my To Do list for the week. It even tells me when I’m on or off track. Here’s what my AI assistant says I need to do this week based on my goals for the next few months.

This one-to-many approach scales my output with minimal effort (or expense).

Over the past year, AI tools like ChatGPT and Claude have evolved from simple text generators into powerful productivity multipliers. They’re only getting smarter, too, which is why I intend to lean on them more to run my business.

If you want to turn ChatGPT or Claude into your executive assistant, I cover one topic in my private newsletter: PromptWritingStudio. Follow my approach AI engineering will save you at least five hours a week.

PromptWritingStudio is a paid newsletter for creators who want to use AI without losing the human touch. I’ll give you prompts, templates, and tutorials. You can also watch over the shoulder as I show you how to set up and use AI for your business.

Reply “AI” and I’ll send you details (it’s currently in beta at a tasty discount).