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Artwork for The Thoughtful Entrepreneur
Entrepreneurship
Artificial Intelligence
Leadership
Leadership Development
Business Growth
Marketing
Customer Experience
Personal Development
Storytelling
Business Coaching
E-Commerce
Time Management
Personal Branding
Emotional Intelligence
Coaching
Uncertainty
Branding
Agentic AI
Work-Life Balance
Digital Advertising

The Thoughtful Entrepreneur features candid, commercial-free conversations with the founders, CEOs, and B2B leaders building the companies and ideas shaping their industries. Each episode runs 15-25 minutes, built for busy professionals who want substance without the filler. Guests include agency owners, consultants, coaches, and executives with real stories, hard-won lessons, and specific insight... more

PublishesDailyEpisodes2000Founded8 years ago
Number of ListenersCategories
ManagementBusinessEntrepreneurship

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Artwork for The Thoughtful Entrepreneur

Latest Episodes

The Systematized Executive: Engineering Operational Freedom with Heather Hargrove

In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Heather Hargrove, an independent consultant and the founder of Grove, to di... more

Operational Civic Leadership: Public Service, Transparency, and Grassroots Strategy with Ebie Lynch

In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Ebie Lynch, a candidate running for California Lieutenant... more

One Big Idea 6 - Creating Autonomous Enterprise Teams Through AI Squads with Superbo AI's Demetri Papazissis

In this episode of One Big Idea, host Josh Elledge sits down with Demetri Papazissis, the Co-founder and CEO of Superbo AI. Demetri joins th... more

The AI-Driven Threat Matrix: Architectural Cybersecurity and Compliance for Small Firms with Michele Novack

In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Michele Novack, the host and founder of Cardinals... more

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SmartLess
SmartLessJason Bateman, Sean Hayes, Will Arnett

Recent Guests

Anthony Reeves
Outback Kid to Global Boardrooms; author of Eat the Donkey; former Amazon executive
Author/Speaker/Former Amazon executive
Episode: 2438 - When Rerouting a Cruise Ship Becomes a Lesson in Leadership and Accountability with Anthony Reeves
Joshua Altman
Founder Beltway Media
Beltway Media
Episode: 2437 - The Growing Importance of Fractional Chief Communications Officers for Businesses with Beltway Media's with Joshua Altman
Jeremy Yang
Founder of Digital Goliath
Digital Goliath
Episode: 2436 - Winning in Online Advertising Through AI and Authenticity with Digital Goliath's Jeremy Yang
Dr. Sabrina Starling
Founder of Tap The Potential
Tap The Potential
Episode: 2435 - Farming Your Business for Freedom and Profit with Tap The Potential's Dr. Sabrina Starling
Aaron Ryan
Author and voice actor
Independent
Episode: 2434 - A Voice Actor’s Take on AI and the Future of Voice Work with Aaron Ryan
Bjorn Vikard
Growth-minded family business coach working with manufacturing leaders
Self-employed / Bjorn Vikard
Episode: 2433 - A Complete Roadmap for Family Business Success and Succession Planning with Bjorn Vikard
Greg Grand
Founder of G Squared Advisors; creator of the AI Sales Leader
G Squared Advisors
Episode: 2432 - Integrating AI to Transform Sales and Accelerate SMB Revenue Growth with G Squared Advisors' Greg Grand
Keith Gillispie
Founder of REI Automated
REI Automated
Episode: 2431 - Real Estate Investing Lessons from a Marine Corps Veteran with REI Automated's Keith Gillispie
Justin Froeber
Founder and CEO of Elite Travel Hackers
Elite Travel Hackers
Episode: 2430 - Insider Travel Hacking Tips from Elite Travel Hackers’ Justin Froeber

Host

Josh Elledge
Host of The Thoughtful Entrepreneur

Reviews

4.9 out of 5 stars from 130 ratings
  • informative podcast..

    This was such an insightful episode to listen to, especially the focus on protecting capital before chasing aggressive returns. I liked how the conversation emphasized strategy, patience, and alignment with long-term goals rather than quick financial wins

    Apple Podcasts
    5
    Mary Burruss
    United Statesa month ago
  • Outstanding interviewer

    I was lucky enough to be interviewed by Josh, he is a top professional who has perfected the craft of podcast hosting! Well done, Josh!

    Apple Podcasts
    5
    Jimjimma5
    United States3 months ago
  • Must-listen

    Josh has great conversations that hook you in with someone’s real life outside of work and then give you real tips to help you in building your business intentionally.

    Apple Podcasts
    5
    Antipasti13
    United States5 months ago
  • Smart, Real

    Sharp, heartfelt insights in just 15–25 minutes each day. You can’t beat that! Immediate thought-provoking information with from high-level B2B leaders sharing authentic stories. It’s a top-tier daily pick for growth-minded pros who value substance over hype.

    Apple Podcasts
    5
    lavhill
    United States7 months ago
  • Great interview, and amazing conversation!

    Loved hopping on the pod with Josh a few days back. Really enjoyed our conversation as it wasn’t the same old questions I usually get asked! Great guy, and the podcasts he produces are great. Cheers

    Apple Podcasts
    5
    nvguy2009
    United Statesa year ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners praise the host for thoughtful questions and practical insights.
Guests note the professional production and value offered to audiences.
Audiences appreciate concise, high-quality episodes ideal for daily routines.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

2438 - When Rerouting a Cruise Ship Becomes a Lesson in Leadership and Accountability with Anthony Reeves
Q: How should leaders handle mistakes to maintain trust with customers and employees?
Leaders should own up to mistakes publicly, apologize when appropriate, and communicate what will be done to fix the issue, because trust is built through transparency, accountability, and concrete corrective actions.
2438 - When Rerouting a Cruise Ship Becomes a Lesson in Leadership and Accountability with Anthony Reeves
Q: What parallels do you see between endurance sports, golf focus, and leading in the boardroom?
Endurance sports teach sustaining focus and embracing a difficult, repetitive state, which translates to leadership where you must stay disciplined under pressure, tune into small details, and maintain consistency with long-term objectives.
2438 - When Rerouting a Cruise Ship Becomes a Lesson in Leadership and Accountability with Anthony Reeves
Q: Anthony, might you give us a quick overview of Eat the Donkey and how it connects to leadership and discomfort?
Eat the Donkey is a manifesto against average that argues great companies embrace discomfort to drive meaningful progress. It ties to leadership by illustrating how leaders should design systems that continually push for improvement and tolerate productive discomfort, rather than settling for the status quo.
2435 - Farming Your Business for Freedom and Profit with Tap The Potential's Dr. Sabrina Starling
Q: What does the $10,000 an hour activity framework look like in practice?
She explains a time-management system where activities are categorized by value, with a laminated chart to keep herself and her team focused on high-impact work, and how delegation grows as more time is reclaimed.
2435 - Farming Your Business for Freedom and Profit with Tap The Potential's Dr. Sabrina Starling
Q: Tell us about the farm and your personal story behind it.
Dr. Starling describes becoming an accidental farmer after her husband Ned passed away, and how she learned to manage the farm—vaccinations, trailer skills, and supporting their children's entrepreneurial learning—while building a business that supports life.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About The Thoughtful Entrepreneur

What is The Thoughtful Entrepreneur about and what kind of topics does it cover?

The show features concise, practical conversations with founders, CEOs, and B2B leaders who share actionable lessons for growing and running businesses. Recent episodes center on disciplined capital strategies, regulatory compliance in service industries, biotech and longevity, leadership psychology, scalable operations with AI, AI-driven agents, franchise leadership, and modern marketing approaches like StoryBrand and UX-focused product design. Across episodes, guests emphasize practical frameworks, measurable outcomes, and authentic storytelling tailored to busy professionals seeking impact without fluff. The format tends to be short, tightly focused, and business-result driven, making it a strong fit for listeners who want clear takeaway... more

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Which podcasts are similar to The Thoughtful Entrepreneur?

These podcasts share a similar audience with The Thoughtful Entrepreneur:

1. SmartLess

How many episodes of The Thoughtful Entrepreneur are there?

The Thoughtful Entrepreneur launched 8 years ago and published 2000 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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What guests have appeared on The Thoughtful Entrepreneur?

Recent guests on The Thoughtful Entrepreneur include:

1. Anthony Reeves
2. Joshua Altman
3. Jeremy Yang
4. Dr. Sabrina Starling
5. Aaron Ryan
6. Bjorn Vikard
7. Greg Grand
8. Keith Gillispie

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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