The Caffeinated Entrepreneur™ Podcast Podcast By Alison Leigh Simmons cover art

The Caffeinated Entrepreneur™ Podcast

The Caffeinated Entrepreneur™ Podcast

By: Alison Leigh Simmons
Listen for free

The Caffeinated Entrepreneur Podcast is where we say the thing we’re all thinking… but no one really wants to admit.

Each week, Alison (high-energy, coffee-fueled, systems-obsessed) and Bernie (calm, steady, mustache-powered) take one issue of The Caffeinated Entrepreneur newsletter and go “behind the brew” of what’s really happening in business life: the messy decisions and identity spirals heated up with the never-ending pressure felt and soooo many pivots required, with just a splash the stuff you cannot wrap up in a neat little 5-step framework stirred in.

No teaching. No pretending we’ve got it all together. Just two entrepreneurs, talking it out like real people.

Same brew. Different cup. Extra caffeine.

All rights reserved.
Economics Leadership Management & Leadership
Episodes
  • #3 Letting Go So You Can Grow Again
    Mar 24 2026

    ☕ 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/

    Show more Show less
    20 mins
  • #2 When Success Gets Boring
    Mar 24 2026

    ☕ 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/

    Show more Show less
    24 mins
  • #1: Networking Isn’t What You Think It Is
    Mar 24 2026

    ☕ 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/

    Show more Show less
    22 mins
No reviews yet