The Caffeinated Entrepreneur™ Podcast cover art

The Caffeinated Entrepreneur™ Podcast

The Caffeinated Entrepreneur™ Podcast

By: Alison Leigh Simmons
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About this listen

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.

All rights reserved. Economics Leadership Management & Leadership
Episodes
  • Ep 0: The Trailer

    Ep 0: The Trailer
    Mar 10 2026

    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 strategy
    • What leadership really feels like in different seasons
    • Why 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.
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    1 min
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