the caffeinated entrepreneur
For visionary entrepreneurs who want less overwhelm and more action.
Welcome to The Caffeinated Entrepreneur! The blog brewed for business owners who are ready to work smarter, not harder. If you’re juggling big dreams, an overflowing to-do list, and maybe a triple-shot latte just to keep up… you’re in the right place.
The Holiday Dump List: How to Actually Rest and Still Crush 2026

Recent Brews from The Caffeinated Entrepreneur
Pour yourself a cup and catch up on the latest! Each issue is packed with no-nonsense tips, fresh insights, and real-life lessons to help you cut through overwhelm and keep your business moving forward. Whether you’ve got five minutes or fifty, you’ll leave with something practical you can apply today.
Chapters
I AM
Alison Leigh Simmons

An AI-Powered Business Builder for 6-figure entrepreneurs who want to think like a 7-figure CEO.
I teach you how use AI tools to control your calendar, make confident decisions faster, and build a successful business you love without torching your personal life in the process.
After developing my own AI-powered business model, I quadrupled my revenue, paid off all my debt, and took control of their business in a way I had never been able to before.
And now I teach other entrepreneur’s and small business owners how do it too!
If your brain feels like a browser with 47 tabs open, you’re in the right place.
My goal is to simplify, focus, and execute your energy where it matters most, all with a little help from AI.
I’m not bossy about it, just aggressively helpful. 😉
What readers think…
★★★★★
Reading this newsletter is like sitting down with the brutally honest biz bestie I didn’t know I needed.
Finally, someone who gets what it’s like to build a business while spiraling over spreadsheets and questioning every decision. Alison says what we’re all thinking but too afraid to admit. It’s funny. It’s real. And it makes me feel way less alone.
★★★★★
It’s like she climbed inside my brain and started narrating my entrepreneurial meltdowns (with the perfect blend sarcasm and strategy mixed together)..
I’ve never laughed out loud and also immediately opened a spreadsheet to fix my systems… until I read this newsletter. Alison’s blend of transparency, wit, and actually useful advice is unmatched.
★★★★★
The only email I look forward to opening (and forwarding to my overworked founder friends).
Alison doesn’t sugarcoat anything! She calls out the chaos behind the curtain of scaling and gives real talk that somehow feels like a hug and a kick in the pants. In a good way.
