☕ Grab your favorite caffeinated beverage and join us for today's episode where we're going behind the brew of issue #5: 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.

🌐 www.leadsmarterco.com

✉️ alison@leadsmarterco.com

🤝 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/

✉️ bernie@insigniatraining.com

🤝 https://www.linkedin.com/in/badiii/

☕ Grab your favorite caffeinated beverage and join us for today's episode where we're going behind the brew of issue #25: The Cat Poop Coffee of Branding

Okay, real question: would you drink the cat poop coffee… and what would it take for you to say yes?

That’s where we start today’s conversation, but what it turns into is the kind of honesty you usually only get from entrepreneurs deep in the trenches of building their brands.

If you’ve ever felt like your work is solid but you’re still blending into the noise, we talk about why “good” isn’t memorable, and why playing it safe is usually the problem. We walk the line between what is authentic vs. gimmicky, and what it feels like when you intentionally stop trying to be universally liked.

Plus, the touching origin of Mustache Moments and the story about the eyelash that abandoned ship mid-zoom call give you a peek behind the curtain of how we developed our own signature brands… because sometimes you don’t choose your brand, it chooses you! Tune in, you’ll probably have an opinion on this one.

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.

🌐 www.leadsmarterco.com

✉️ alison@leadsmarterco.com

🤝 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/

✉️ bernie@insigniatraining.com

🤝 https://www.linkedin.com/in/badiii/

☕ Grab your favorite caffeinated beverage and join us for today's episode where we're going behind the brew of issue #42: Why You’re Not Making More Money (Even Though You’re Brilliant)

Bernie bought a business. Or at least he thought he did. Turns out, what he really bought was a name and a handful of relationships that weren’t fully his yet.

In this episode, we talk about what it felt like to have a million-dollar year… and then watch major clients disappear. About holding onto an old model longer than you probably should. And about that moment where you realize the thing that used to work isn’t what’s going to carry you forward.

This isn’t a “here’s how to pivot” episode. It’s just an honest conversation about what it looks like to loosen your grip, stop splitting your focus, and finally commit to the direction that’s actually gaining traction.

If you’ve ever known something needed to change, but weren’t quite ready to let it go, this one will probably feel familiar.

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.

🌐 www.leadsmarterco.com

✉️ alison@leadsmarterco.com

🤝 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/

✉️ bernie@insigniatraining.com

🤝 https://www.linkedin.com/in/badiii/