The Caffeinated Entrepreneur™ Podcast

Entrepreneurship can feel like you’re building something important while the street stays weirdly empty, no water cooler, no built-in coworkers, and not always a clear place to put the hard stuff (or the good stuff) when it happens.

In this episode, Bernie and I talk about what that loneliness actually looks like in “real life business” and the difference between needing someone for the tough days versus the wins you’re scared to say out loud, the way we each spiral (or shut down) when it’s an “empty parade” season, and why oversharing with the wrong people can cost you more than staying quiet.

We also get practical about the kind of support that actually helps from your “Core 4” and how a relationship-first networking culture can quietly become the bench you lean on when you need perspective, encouragement, or someone to talk you off the ledge.

If you’ve ever felt like your “parade crowd” looked more like an empty street, 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

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 https://www.linkedin.com/in/badiii/

You can work hard, show up consistently, and still feel like your audience is just… watching. This episode is for the moments when you’re doing “all the things” but sales feel oddly quiet, and you can’t tell if it’s your offer, your messaging, or something you’re missing entirely.

Bernie and I talk about the kind of market research that actually matters…the kind that tells you what people want in their own words, not what you hope they want. Because it’s a whole lot easier to sell someone something they already want than to convince them they should want what you built.

If you’ve been posting and praying and calling it strategy, consider this your nudge to stop guessing and start asking. This is founder-level, real-life clarity for anyone who’s ready to get out of the “create and hope” cycle without reinventing their entire business.

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

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 https://www.linkedin.com/in/badiii/

This episode is really about the part nobody talks about: your kids are learning business from you whether you’re trying to teach them or not. They’re watching what success does to you, what failure does to you, and what you make it mean and they’re quietly building their own beliefs about work, risk, money, and resilience from the way you handle it.

Bernie and I talk about the difference between what we say we value (boundaries, family, staying steady) and what we accidentally model when the pressure hits (when the launch flops, when the cash feels tight, when you’re winning but still living like you’re behind). Because your kids don’t take your advice. They copy your actions.

If you’ve ever wondered whether you’re passing down grit… or anxiety… or a workaholic badge of honor… you’ll hear yourself in this one. It’s a coffee chat about succeeding, failing, and recovering out loud, so the people watching you learn the right lessons.

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

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 https://www.linkedin.com/in/badiii/

Most of us aren't stuck because we lack access to good advice. We're stuck because we treat someone else's strategy like a buffet, taking what looks good, skipping what's uncomfortable, and then wonder why it's not working like promised.

In this episode, Bernie and I get honest about what actually has to happen for advice to move from "that's so good" to actually changing how you operate and we are honest about the gap between consuming content and implementing it, why good intentions aren't the problem, and what it really means to surrender to an approach versus just going through the motions.

If you've ever taken a course, had a great coaching call, or bookmarked a podcast and done absolutely nothing with it (my hand is raised!!)…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

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 https://www.linkedin.com/in/badiii/

If you’ve ever stared at an open email thread and thought, “Okay, is this quality follow up, or did I just turn into a teenie bopper waiting on a text back from their crush?”… this one’s for you. We talk about the moment a warm lead turns weird, and how fast your confidence can leak out when you start trying to interpret someone’s silence instead of responding to it.

In this episode, Bernie and I get honest about where that line actually is between professional persistence and straight-up chasing. We unpack the subtle signals people give (and the ones they don’t), what it looks like to close the loop without burning the bridge, and why “fortune is in the follow-up” doesn’t mean you need to keep knocking on a door that’s clearly not opening.

You’ll walk away with a clearer gut-check for your next follow-up, a better way to stay in your CEO energy when someone’s dragging their feet, and a little permission to stop making excuses for prospects who won’t decide.

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

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 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 #19: When “Under Construction” is an Understatement

What does it actually looks like when your business is “under construction” for real? Not just a cute rebrand season, but the kind where the platform shifts under your feet and the systems you built on suddenly stop cooperating.

In this episode, Bernie and I get into the very specific pain of rebuilding while you’re still delivering, still selling, still trying to act like you’re totally fine… while your brain is quietly running a demolition crew in the background.

We also pull apart that tricky question: is this broken, or is this just growth? And what do you hang onto as non-negotiable so you don’t rebuild the wrong thing.

And yes, we’ve both had a moments where we discovered “if the detour is better, you have to make that the main route” which is annoyingly true, but also kind of relieving if you’re in a season where the best next step isn’t the one you planned.

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

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 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 #16: Opportunity —> Problem —> Repeat

I laughed when I pulled this issue from the archive because it’s one of those “oh cool, we’re doing this again” themes and apparently my business heard me and said, “Bet.”

Bernie and I swap stories on the funniest “opportunities turned problems” experiences (someone offered to book me private jets…I don’t think my LinkedIn profile makes me look that successful!), and we talk about what to do when people interrupt your day with a cold pitch. I tend to Uno-reverse them, but Bernie has a mischievous approach, of course.

Then we get into the less-funny part of growth: when the role that helped you build the business isn’t the role you need now and we wrap by normalizing the cycle: bigger problems usually mean you’re playing a bigger game, but repeating the same problems might mean you’re the problem you keep having!

Give it a listen and if you’re in the trenches, fighting business battles right now too, just know you’re not alone… we’re in it with 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

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 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 #43: Why Your Word of the Year Is Lying to You

I’m not anti–Word of the Year… I’m just very familiar with the moment you look up and realize you ghosted yours by February without even noticing. Mine was “Focus,” and the funny part is, I didn’t rebel against it. I just got busy and called it momentum.

Bernie and I talk about shiny-object season and why it’s almost impossible to label something as a “distraction” in real time (especially when the opportunity is genuinely good). We also get honest about how quickly “fun” collaborations can start quietly hijacking the commitments you swore were non-negotiable.

By the end, the question isn’t “Should I try harder?” It’s “Is this a recommit moment or a release moment?” And if you’re not regularly asking what’s working and what isn’t, you’re basically outsourcing your year to whatever shows up loudest.

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.

🌐 http://www.leadsmarterco.com

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 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 #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

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 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

✉️ [email protected]

🤝 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/

✉️ [email protected]

🤝 https://www.linkedin.com/in/badiii/