Hey there, I’m Alison Leigh Simmons.
Business manager by trade. Systems whisperer by calling. Caffeine enthusiast by necessity.
This little corner of the internet is where I share the behind-the-scenes no one’s putting on their highlight reels about running a business, scaling sustainably, and not losing your ever-loving mind in the process.
If you’ve ever found yourself staring at your to-do list like it’s a Choose Your Own Adventure book from hell… welcome. You’re in good company.
A Little Backstory (Poured Fresh)
Not too long ago, I had “success” on paper. Clients, consistent income, a calendar full of Zoom calls. And yet… I was exhausted. My business looked fine from the outside but felt like a dumpster fire of duct-taped systems and decision fatigue on the inside.
So I did what any slightly overwhelmed, highly caffeinated business owner would do: I turned to ChatGPT for help and, over a period of 6 months, built my own AI-powered business.
Not kidding. I automated the chaos, simplified the noise, and created space to breathe again.
That’s when things shifted.
Now? I use this newsletter to share the lessons, mindset shifts, systems, and occasional soapbox moments that help solopreneurs like you scale without spiraling.
What You’ll Find Here
This isn’t another “rise and grind” productivity fest. Nope.
Think of it like your weekly espresso shot of:
- Encouragement when you’re ready to burn it all down
- Strategy that actually fits into your real life
- Stories from the trenches (aka: me, learning things the hard way so you don’t have to)
- A little humor, a little humility, and a lot of honesty
If you’ve ever wished someone would just say what we’re all thinking about this entrepreneurial rollercoaster, you’ll feel right at home here.
So, Why Stay a While?
Because you’re not the only one trying to build something meaningful without burning out.
And because this newsletter?
It’s not just content. It’s connection.
It’s your weekly reminder that you’re not alone, you’re not behind, and you’re absolutely capable of doing this thing on your terms.
Ready for your weekly dose of caffeine + clarity?
Read through the published issues and subscribe below to get the newest brew straight into your inbox.
No nonsense. No pressure. Just real talk, strong strategy, and the occasional sarcastic meme.😉
And remember, keep showing up, keep taking the next step, because the caffeine is strong… and so are you.
Want to learn more about my “day job?” Check out Lead Smarter Co!
thecaffeinatedentrepreneur.com 