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The Caffeinated Entrepreneur™ Podcast
The Caffeinated Entrepreneur™ Podcast episodes
- #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
🤝 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://www.linkedin.com/in/badiii/
45 min - #22 What People Trust Before They Buy
Reputation is one of those things we like to think we control, but the truth is a little messier than that. It is shaped in the moments people remember, repeat, and quietly use to decide whether they trust us enough to work with us or send someone else our way.
This conversation is about more than the usual “referral talk.” It is really about trust, character, experience, and the small behaviors that make someone feel confident putting their own name next to yours.
If you are growing, pivoting, or stepping into a more visible role in your business, this one is worth sitting with because what people say when you are not in the room may be your strongest sales asset, or it may be showing you where the next layer of leadership needs to happen.
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
🤝 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://www.linkedin.com/in/badiii/
36 min - #21 When Your Brain Waves the White Flag
There is a point where life stress and business pressure stop politely taking turns. They collide, they pile up, and suddenly the things you usually handle without thinking start feeling heavier than they should.
This conversation is about that founder-level moment when the issue may not be your strategy, your discipline, or your ambition. It may be that your capacity is maxed out, and your brain is asking for support before it turns every decision into a much bigger problem.
If you have ever looked at your calendar, your family, your inbox, or your to-do list and thought, “I cannot keep doing it like this,” this one will feel familiar. Not because it fixes the hard season, but because it names what is happening underneath it.
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
🤝 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://www.linkedin.com/in/badiii/
33 min - #20 Finding the Price That Fits
Pricing gets uncomfortable when the number on the invoice no longer matches the version of the offer you are actually delivering. What used to feel generous can quietly turn into resentment, especially when the scope, support, experience, or transformation has grown but the price stayed behind.
This conversation is about the tension between charging with integrity and holding a price that no longer fits. There is a real difference between overdelivering because you care and overdelivering because your boundaries, confidence, or offer structure have not caught up yet.
If you have ever wondered whether your price needs to go up, your offer needs to get stronger, or your client relationships need cleaner expectations, this one will feel familiar. It is a grounded conversation about value, maturity, and learning to say the number without spiraling afterward.
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
🤝 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://www.linkedin.com/in/badiii/
35 min - #19 The View You Can’t Get Alone
There is a strange kind of frustration that shows up when you are great at seeing the next move for everyone else, but your own business feels harder to sort. When everything has history, context, pressure, and possibility attached to it, it gets harder to tell the difference between what’s working, what’s not, and what you need to just wait out.
If you are in a season of business where your brain feels tangled trying to hold it all, this episode will feel familiar. It is a coffee-fueled reminder that needing outside perspective does not make you less capable. It may be the thing that helps you lead with a little more clarity.
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
🤝 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://www.linkedin.com/in/badiii/
33 min - #18 When Their Success Feels Like a Threat
☕ Grab your favorite caffeinated beverage and join us for today's episode, where we're going behind the brew of issue #68: When Comparison Hijacks Your Brain
Comparison gets weird fast when someone else’s win starts feeling like a threat. It is one thing to notice success and feel inspired by it. It is another thing entirely when your brain starts building a whole story around why someone else got what you wanted faster, easier, or louder than you did.
This conversation is about the less polished side of comparison - the part where jealousy, frustration, and public reactions can start shaping how people experience your brand. Because the way we handle someone else’s success says a lot, especially when we are still building our own.
If you have ever felt that sting when another founder seems to be winning faster, this one will feel familiar. We are talking about what happens when comparison gets loud, how to process it without letting it spill everywhere, and why someone else’s visible success is rarely the whole story.
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
🤝 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://www.linkedin.com/in/badiii/
31 min - #17 When Success Stops Looking Like a Number
There is a strange thing that happens when you spend years chasing business goals. You can hit the number, book the client, cross the milestone, and still feel like you are waiting for success to finally arrive.
This conversation sits in that uncomfortable space between achieving something you’ve been working towards and actually feeling the thing you thought achievement would give you. Because sometimes the evidence that the business is working does not show up as a dramatic win or big milestone. Sometimes it shows up in a very normal moment that suddenly feels like a reason to celebrate.
If success has ever felt harder to recognize than achievement, this one is for you. It is a conversation about ambition, perspective, and learning to notice the ordinary moments all your work is making possible.
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
🤝 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://www.linkedin.com/in/badiii/
29 min - #16 When Help Turns Into Rescue
If you’ve ever left a client situation feeling guilty, this episode will feel uncomfortably familiar. There’s a difference between guiding someone through the work and quietly taking responsibility for results they aren’t fully owning.
Bernie and I talk about how this shows up in real life with clients: expectations that were never truly aligned, the “easy button” energy that sneaks into the room, and the moment you realize you’re trying to want someone’s success more than they do.
This one is for the service provider who wants to help people win, but wants to do it without becoming the hero of someone else’s story.
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
🤝 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://www.linkedin.com/in/badiii/
29 min - #15 The Thin Line Between Your Vision and the Danger Zone
There’s a kind of belief you need in business that looks a little unhinged from the outside. Not because you’re reckless, but because you’re willing to move before you have proof, and you’re willing to be misunderstood while you do it.
In this episode, Bernie and I talk about that line founders cross without realizing it, the moment vision stops being leadership and starts turning into obsession, overreach, or the danger zone. We also get honest about how much your environment and inner circle can either steady you… or quietly push you into decisions you’ll have to clean up later.
This one’s for the established entrepreneur who’s building something bigger than what their current season can comfortably hold, and wants to stay ambitious without losing integrity, relationships, or sanity.
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
🤝 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://www.linkedin.com/in/badiii/
32 min - #14 The Reps That Build Real Momentum
If you’ve been stuck in a loop of “I know what I should do… I’m just not doing it,” this is your permission slip to stop making it dramatic. In this episode, Bernie and I talk about the 30-day challenge mentality: picking one uncomfortable action and doing it daily long enough to build the habit and strengthen the muscle.
We get into why the first week feels clunky, why your brain starts negotiating around day 10, and why the reps matter more than the mood. Because by the time you hit week four, you’re not just “doing the thing,” you’re better at it, calmer doing it, and you’ve built real momentum you can actually ride.
And Bernie and I both declare our own personal 30 Day Challenges to each other (and you are welcome to be a part of it!)
If you want a founder-level reset that isn’t a total reinvention, this is it. One decision. One daily rep. Thirty days. And a very real chance you’ll surprise yourself with what happens when you stay in it.
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
🤝 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://www.linkedin.com/in/badiii/
28 min
About The Caffeinated Entrepreneur™ Podcast
From the publisher's feed
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.