☕ 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/

☕ Grab your favorite caffeinated beverage and join us for today's episode where we're going behind the brew of issue #3: Why You Keep Moving the Goal Post

Three years ago, Alison thought $2,000 a month was the finish line. Then it was $5,000. Then $10,000.

The problem wasn't greed. It was ambition that drove her to keep changing the goal before she even reached it. In this episode, she talks about what that pattern cost her, how it turned her into the kind of business owner she didn't want to be, and the mindset shift that helped her stop chasing and start building.

If you've ever hit a goal and immediately felt behind, this one's 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 #11: If ‘networking’ feels like speed dating… you’re doing it wrong.

A typo on a website. A networking group I didn't think I belonged in. And a guy who believes in culture over conversions.

This is the story of how Bernie and I went from "nice to meet you" to "let's build a podcast together" and how one weekly Zoom call turned into the biggest business opportunity I've ever had.

In this episode, we're pulling back the curtain on how a “puppy entrepreneur” with 97 LinkedIn connections and a former corporate education trainer ended up here, co-hosting a show about what it takes to keep a business going long after the excitement of launch phase is over.

If you've ever wondered whether networking actually pays off, grab your coffee and settle in. This is where it all started.

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/

If “entrepreneurship” has ever felt like you’re carrying the vision, the execution, and the emotional weight… all at the same time, this podcast is for you.

The Caffeinated Entrepreneur Podcast is where I take the weekly newsletter conversation and bring it into real life. Not as a lesson. Not as a step-by-step training. But as the honest behind-the-scenes version: the decisions, the doubts, the momentum, the messy middle, and the “I cannot believe this is my job” moments.

You’ll hear me (Alison), your super high-energy host, and Bernie, my mustached partner-in-crime who keeps the vibe grounded, talk through what building a business actually looks like when you’re trying to grow without burning out.

We’ll cover the stuff founders don’t always say out loud:

• What’s happening under the strategy
• What leadership really feels like in different seasons
• Why certain decisions drain you, even when they’re “right”
• And how to keep moving without turning your business into a chaos machine

If you you’d rather listen to a real conversation you can relate to than another lecture, press play.