The Unscheduled CEO

Jonathan Courtney

Business Management

Latest episode

67 episodes

Getting clients: Easy Mode vs Hard Mode
03/2/2026 | 57 mins.
You guys ask me all the time: “How do I get more clients???”
So here I (mostly) talk about it.Enjoy!
You can listen to this episode anywhere you listen to podcasts and its also on Youtube:
Cheers,Jonathan

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com
I embarrassed myself in front of 3,500 people
27/1/2026 | 50 mins.
HEY LOVELY PEOPLE,
This is a juicy episode all about how I deal with feedback, criticism and online trolls.
It’s a spicy one. Don’t listen if you don’t want spice.
You can listen to this episode anywhere you listen to podcasts and its also on Youtube:
Cheers,Jonathan

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com
I finally found the ULTIMATE AI use-case!
20/1/2026 | 56 mins.
Ok ok ok, it finally clicked for me after using a new, crazy tool.
The AI hype makes sense.
I haven’t been this pumped about technology in like… a decade?
Let’s talk about it.
You can join the webinar I mentioned is right here.
You can listen to this episode anywhere you listen to podcasts and its also on Youtube:
Cheers,Jonathan

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com
A chat with my biggest competitor: Chad Littlefield
13/1/2026 | 2h 12 mins.
Hey! What’s up?
This week i’ve got the beautiful Chad Littlefield (my mortal enemy) and we chatted about:
* The Contribution Method (and How to Stop Exhausting Yourself Running Events)
* AI is Going to Expose That Most Jobs Were Never Real
* Ditching the Smartphone (and Why It Actually Worked)
* The Return of In-Person Gatherings (and Why You’re Betting Big on Them)
* Spirituality, Meditation, and Listening to Something Bigger
This episode was a mess audio-wise and there was a slight delay in our connection, but you’re not listening to this crap to transcend or some s**t right?
You can listen to this episode anywhere you listen to podcasts and its also on Youtube:
Cheers,Jonathan

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com
My plan to make millions while having fun in 2026
06/1/2026 | 51 mins.
IM BACK
YOU READY? Yeah? Ok.
In this episode I talk about
* How to get what you want by understanding Agency
* Other stuff
You can listen to this episode anywhere you listen to podcasts and its also on Youtube:
Cheers,Jonathan

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

More Business podcasts

About The Unscheduled CEO

WARNING: This is an extremely serious and useful business podcast with many useful takeaways and interviews. This podcast is like getting an occasional voice-note from an entrepreneur who's running a multi-million dollar (profit) business. It's raw, completely unedited but most importantly: actionable! Honestly, this should be called "Diary of a CEO", but that's... like.... taken already I think. The Unscheduled CEO, hosted by Jonathan Courtney is counterintuitive advice on running a Small Business by someone who's been running one for over 13 years. Jonathan Courtney is the CEO of AJ&Smart.com and Workshopper.com Got a question you want to be read out on air? Comment on the current episode here: https://howtobusiness.substack.com/ www.unscheduledceo.com

Podcast website

Business Management