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.
Saying yes to a good idea feels different once it becomes a recurring commitment on an already-full calendar. You can still care about what you’re creating and have days when finding the time and energy to show up takes more than you expected.
For this behind-the-scenes conversation, Bernie and I look at what it means to keep making something together while our businesses and lives keep happening around it. There’s a difference between enjoying someone’s company and figuring out how to create with them, especially when you each bring different expectations and ways of working.
If you’ve ever committed to a project with someone else, you’ll recognize the questions that surface once you’ve been at it for a while. What makes it worth continuing, and how do you let it grow without losing the part you liked in the first place?
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 (http://www.leadsmarterco.com)
✉️ alison@leadsmarterco.com (mailto:alison@leadsmarterco.com)
🤝 https://www.linkedin.com/in/alison-leigh-simmons/ (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/ (https://insigniatraining.com/)
✉️ bernie@insigniatraining.com (mailto:bernie@insigniatraining.com)
🤝 https://www.linkedin.com/in/badiii/ (https://www.linkedin.com/in/badiii/)
13 Oct 2026
#24 Can Your Business Change Without Changing Who You Are?
Business growth gets uncomfortable when people still expect the access you could offer before your calendar filled up and your work changed and holding a boundary can feel reasonable right up until someone treats that decision as evidence that you’re no longer the person they thought you were.
In the conversation, Bernie and I talk about the tension between being generous and being available, and why criticism lands differently when it questions your character rather than your work.
If you’re changing how you serve people and finding that not everyone welcomes the change, this conversation will feel familiar. It’s an honest chat about the expectations that stay with us as our businesses evolve, and how personal it can feel when those expectations no longer fit.
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 (http://www.leadsmarterco.com)
✉️ alison@leadsmarterco.com (mailto:alison@leadsmarterco.com)
🤝 https://www.linkedin.com/in/alison-leigh-simmons/ (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/ (https://insigniatraining.com/)
✉️ bernie@insigniatraining.com (mailto:bernie@insigniatraining.com)
🤝 https://www.linkedin.com/in/badiii/ (https://www.linkedin.com/in/badiii/)
6 Oct 2026
#23 What Future You Already Knows
It’s easy to picture future success as a more impressive version of what already exists. Still, when you ask what you actually want an ordinary day to feel like, the answer gets more personal and usually more honest.
The business you want later is shaped by choices you’re already making about your time, your work, and what you’re willing to outgrow. Future-you may not have a profound message; that version of you may simply be confirming the change you already know needs to happen.
This conversation is for the business owner who has outgrown parts of the way they currently work but hasn’t fully named what comes next. It’s a chance to think beyond the usual markers of success and listen for what your own vision has been trying to tell 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 ways that actually reduce day-to-day chaos.
🌐 www.leadsmarterco.com (http://www.leadsmarterco.com)
✉️ alison@leadsmarterco.com (mailto:alison@leadsmarterco.com)
🤝 https://www.linkedin.com/in/alison-leigh-simmons/ (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/ (https://insigniatraining.com/)
✉️ bernie@insigniatraining.com (mailto:bernie@insigniatraining.com)
🤝 https://www.linkedin.com/in/badiii/ (https://www.linkedin.com/in/badiii/)
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