Does Your Boss Owe You a Raise?
(oh wait…that’s YOU!)
☕ Grab your favorite caffeinated beverage and join us for today’s episode, where we’re going behind the brew of issue #15: I Made More Money and Still Felt Broke (Here’s What I Missed)
In this episode, Bernie and I talk about that maddening moment when your business is ‘doing well’ on paper… but your bank account still hasn’t gotten the memo.
We get real about the stuff that quietly drains you, like subscriptions you forgot you had, upgrades that felt “responsible,” and reinvesting so hard you never actually feel the win. We also share a couple of our own stories (credit cards, bad timing, and yes, me being annoyed that Bernie’s audio is better than mine).
Then I walk through my CEO Expense Checklist, because at some point you have to ask the question nobody wants to ask: is this decision building a business that takes care of you, or just a business that keeps taking.
If you’ve ever hit a revenue milestone and still wondered where the money went… then this one is for you.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
thecaffeinatedentrepreneur.com 