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The Caffeinated Entrepreneur™ Podcast
Updated 12 days ago · Refreshed hourly
businessentrepreneurship

The Caffeinated Entrepreneur™ Podcast

Hosted by Alison Leigh Simmons · 🇺🇸 US · EN · 11 episodes

Where this show ranks

Episodes
11
Last ep.
16 days ago
Avg length
25m
Booking Probability™
36
Stretch.
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Estimated audience
,
Audience size not yet estimated
Listen Score
15
Niche reach.
Virality (30d)
45
Steady cadence.

Pitch Analysis

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Required Pod Score
80/ 100
Premium

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Contact path
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Guest openness
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Best topics to pitch
businessentrepreneurship

About this 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 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.*

businessentrepreneurship

About the host

Alison Leigh Simmons hosts The Caffeinated Entrepreneur™ Podcast, a business show with 11 episodes published.

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Recent episodes

Our AI reads these to draft pitches

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

Jun 2, 202640mEp. 11S1

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

Show notes

#10 The Gap Between Good Advice and Real Results

May 12, 202630mEp. 10S1

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 worki

Show notes

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

May 4, 202628mEp. 9S1

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

Show notes

#8 When the Detour Becomes the Main Route

Apr 28, 202631mEp. 8S1

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

Show notes

#7 When Opportunities Start Punching Back

Apr 21, 202625mEp. 7S1

☕ 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

Show notes

#6: When Momentum Becomes a Distraction

Apr 14, 202625mEp. 6S1

☕ 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 w

Show notes

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

Apr 7, 202627mEp. 5S1

☕ 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 ab

Show notes

#4 Sometimes Your Brand Choose YOU

Mar 31, 202627mEp. 4S1

☕ 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

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#3 Letting Go So You Can Grow Again

Mar 24, 202620mEp. 3S1

☕ 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 le

Show notes

#2 When Success Gets Boring

Mar 24, 202624mEp. 2S1

☕ 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 lin

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

Mar 24, 202622mEp. 1S1

☕ 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

Show notes

Ep 0: The Trailer

Mar 10, 20260mEp. 1S1

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

Show notes

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Audience demographics

Age
25-54
Consumer type
Professionals & Founders

Topics covered

businessentrepreneurship

Successful pitch examples

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Best industries to pitch The Caffeinated Entrepreneur™ Podcast for

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Frequently asked questions

How do I pitch The Caffeinated Entrepreneur™ Podcast as a podcast guest?

The Caffeinated Entrepreneur™ Podcast has a verified contact on file. Create a free PitchCentric account to access it and generate a personalised pitch in seconds. Research at least 3 recent episodes first and lead with a specific angle that serves their business audience.

Who is the host of The Caffeinated Entrepreneur™ Podcast?

The Caffeinated Entrepreneur™ Podcast is hosted by Alison Leigh Simmons. The show is categorised under business (entrepreneurship) and has published 11 episodes.

How many episodes does The Caffeinated Entrepreneur™ Podcast have?

The Caffeinated Entrepreneur™ Podcast has published 11 episodes.

What topics does The Caffeinated Entrepreneur™ Podcast cover?

The Caffeinated Entrepreneur™ Podcast regularly covers business, entrepreneurship. It sits in the business category, with a entrepreneurship focus.

Is it hard to get booked on The Caffeinated Entrepreneur™ Podcast?

The Caffeinated Entrepreneur™ Podcast is accessible for guests with genuine business expertise. A personalised, episode-aware pitch will still outperform a generic one every time.

Is The Caffeinated Entrepreneur™ Podcast currently accepting guest pitches?

The Caffeinated Entrepreneur™ Podcast hasn't explicitly signalled guest openness in recent episodes. That doesn't rule out pitching. your hook just needs to be especially compelling and relevant to their recent content.

How long are The Caffeinated Entrepreneur™ Podcast episodes?

Episodes of The Caffeinated Entrepreneur™ Podcast average 25 minutes. a focused format where a clear narrative arc and tight preparation matter most.

What guest credentials does The Caffeinated Entrepreneur™ Podcast typically look for?

Our data rates The Caffeinated Entrepreneur™ Podcast's guest bar at 80/100 (Premium tier). Established thought leaders with verified media credentials. Sign in to PitchCentric to see how your own Pod Score compares against this show.

Methodology. Booking Probability™ blends Listen Score, 30-day Virality, open-to-guests detection, and Apple ratings. Data refreshed every 60 minutes. Listen Score and Booking Probability are calculated by PitchCentric. Last enriched 12 days ago.

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