The Caffeinated Entrepreneur™ Podcast
Alison Leigh SimmonsThe 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 heate... more
| Publishes | Weekly | Episodes | 16 | Founded | 4 months ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | EntrepreneurshipBusiness | |||
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Latest Episodes
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 episo... more
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... more
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,... more
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 som... more
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 ... more
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 epi... more
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 ... more
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 r... more
Key Facts
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Chart Rankings
How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.
Apple Podcasts | #202 |  Colombia/Business/Entrepreneurship |
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Listeners, social reach, demographics and more for this podcast.
| Listeners per Episode | Gender Skew | Location | |||
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Frequently Asked Questions About The Caffeinated Entrepreneur™ Podcast
What is The Caffeinated Entrepreneur™ Podcast about and what kind of topics does it cover?
Two high-energy, pragmatic founders discuss the messy realities of entrepreneurship, focusing on real-world decision making, pivots, and the emotional cadence of building and growing a business. Across episodes they swap personal anecdotes, methods, and systems-driven tactics—covering topics from branding and client follow-up to pivots in service offerings, virtual events, and the role of coaching and accountability. The tone is candid, no-nonsense, and caffeine-fueled, with an emphasis on sustainable progress over quick frameworks. The show often leans into the human side of entrepreneurship—motivation, burnout, and the tensions between doing things themselves and outsourcing—making it especially useful for solo founders, small teams, and ... more
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How many listeners does The Caffeinated Entrepreneur™ Podcast get?
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How many episodes of The Caffeinated Entrepreneur™ Podcast are there?
The Caffeinated Entrepreneur™ Podcast launched 4 months ago and published 16 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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