HeyJaredThe Caffeinated Entrepreneur™ Podcast
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…
- Indexed episodes, last 90 days
- 7
- Latest publication
- Aug 18, 2026
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- Earliest in this view
- Jul 7, 2026
Latest episodes
#22 What People Trust Before They Buy (opens the original)
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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,
#21 When Your Brain Waves the White Flag (opens the original)
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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 lo
#20 Finding the Price That Fits (opens the original)
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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 becaus
#19 The View You Can’t Get Alone (opens the original)
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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 reminde
#18 When Their Success Feels Like a Threat (opens the original)
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☕ 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 polishe
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