The Caffeinated Entrepreneur™ Podcast

Alison Leigh Simmons
  • 0.0 (0)
  • Entrepreneurship
  • Updated Weekly

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.

Episodes

  1. #11 What Your Kids Learn From Your Business (good or bad)

    6d ago

    #11 What Your Kids Learn From Your Business (good or bad)

    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 ✉️ 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/

    41 min
  2. #10 The Gap Between Good Advice and Real Results

    May 12

    #10 The Gap Between Good Advice and Real Results

    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 ✉️ 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/

    30 min
  3. #9 Stop Chasing: “Follow-Up” Shouldn’t Look Desperate

    May 4

    #9 Stop Chasing: “Follow-Up” Shouldn’t Look Desperate

    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 ✉️ 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/

    29 min
  4. #8 When the Detour Becomes the Main Route

    Apr 28

    #8 When the Detour Becomes the Main Route

    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 ✉️ 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/

    32 min

  5. Apr 21

    #7 When Opportunities Start Punching Back

    ☕ 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 ✉️ 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/

    26 min
  6. #6: When Momentum Becomes a Distraction

    Apr 14

    #6: When Momentum Becomes a Distraction

    ☕ 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 ✉️ 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/

    25 min
  7. #5 Does Your Boss Owe You a Raise? (oh wait...that's YOU!)

    Apr 7

    #5 Does Your Boss Owe You a Raise? (oh wait...that's YOU!)

    ☕ 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 ✉️ 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/

    28 min
  8. #4 Sometimes Your Brand Choose YOU

    Mar 31

    #4 Sometimes Your Brand Choose YOU

    ☕ 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 ✉️ 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/

    28 min
  9. #3 Letting Go So You Can Grow Again

    Mar 24

    #3 Letting Go So You Can Grow Again

    ☕ 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/

    20 min
  10. #2 When Success Gets Boring

    Mar 24

    #2 When Success Gets Boring

    ☕ 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/

    24 min
  11. #1: Networking Isn’t What You Think It Is

    Mar 24

    #1: Networking Isn’t What You Think It Is

    ☕ 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/

    22 min
  12. Ep 0: The Trailer

    Mar 10

    Ep 0: The Trailer

    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 strategyWhat leadership really feels like in different seasonsWhy 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.

    1 min
  • 12 Episodes

About

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.

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