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PODCAST

The Unscheduled CEO

Jonathan Courtney

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 management

All Episodes

57:13

Getting clients: Easy Mode vs Hard Mode

The Unscheduled CEO ·

2026/02/03

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

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50:54

I embarrassed myself in front of 3,500 people

The Unscheduled CEO ·

2026/01/27

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

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56:29

I finally found the ULTIMATE AI use-case!

The Unscheduled CEO ·

2026/01/20

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

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132:44

A chat with my biggest competitor: Chad Littlefield

The Unscheduled CEO ·

2026/01/13

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 BiggerThis episode was a mess audio-wise and there was a slight delay in our

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51:22

My plan to make millions while having fun in 2026

The Unscheduled CEO ·

2026/01/06

IM BACKYOU READY? Yeah? Ok.In this episode I talk about* How to get what you want by understanding Agency* Other stuffYou 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

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55:54

An update on my ADHD journey

The Unscheduled CEO ·

2025/12/16

Hey!We made it to the final Unscheduled CEO episode of 2025! PHEW!In this episode I talk about* Results of my 1 year ADHD medication experiment* My life-changing mindset going into 2026* My favourite book of the year* How to make sure you stay bold in 2026See you all next year.You can listen to this episode anywhere you listen to podcasts and its also on Youtube: https://youtu.be/vDRPov6g0RkCheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get

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111:31

Listen to a (very personal) call with my mentor...

The Unscheduled CEO ·

2025/12/09

Hey!This week I brought my friend and mentor Blake on the podcast for an open-ended conversation which ended up getting pretty personal.We talked about:* The panic attack I had after a 2-day marathon business/life design session * Why I sometimes feel sad when I see my favourite artists perform* Blake transitioning from artist to business-man back to artist* Intuition, spirituality and romantic relationshipsChapters: 00:00 - Where do I know Blake La Grange from?03:07 - Why Blake’s conversations hit

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56:15

Is working remote bad for your career? (I didn't want...

The Unscheduled CEO ·

2025/12/02

Here’s a question for you: Why do the companies who make some of the most used Remote Work tools on the planet not work remotely?Why do most CEO’s benefit more from remote work than employees?Lots to get into in this episode. Please listen before you post your comment about how remote work is actually very valuable to you etc.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,JonathanP.S. I did a little office tour video you can watch right here. This is a

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42:26

Listen to this if you want to find your purpose in life

The Unscheduled CEO ·

2025/11/25

For over 5 years i’ve been telling people that i’ve sort of lost my “business mojo”.Not that i’ve lost my ability to make money, but that' i’ve started to feel aimless, a bit fatigued and finding it hard to get excited about what i’m doing.Over these 5 years i’ve tried a lot of things, spent a lot of money on coaching, therapy, starting new businesses, trying new creative projects… but I keep ending up in the same place: losing interest and feeling a bit checkout-out.Oh, and, I even tried ADHD

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66:08

This LEAKED company handbook changed my life......

The Unscheduled CEO ·

2025/11/18

About a decade ago a company’s internal blueprint for everything they do was leaked.It changed everything about my business.That’s what this episode is about.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,JonathanP.S. I updated the podcast art to make it more serious and business-like 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

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28:30

The ONLY thing I'm focussing on to grow AJ&Smart in 2026

The Unscheduled CEO ·

2025/11/11

From this week until March 15th 2026 i’m going to be focussing on ONE thing to grow AJ&Smart.And it’s really, reallllly simple.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,JonathanP.S. I updated the podcast are to make it more serious and business-like 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

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65:17

Let's talk about how much I get paid

The Unscheduled CEO ·

2025/11/04

This week i’m talking about my day-rate, which some people are a little shocked about when they hear it.I also talk about a conference I just spoke at!You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,JonathanP.S. I updated the podcast are to make it more serious and business-like 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

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57:00

This personality trait 1000% decides your level of...

The Unscheduled CEO ·

2025/10/28

This week i’m talking about a success trait that’s not only measurable, but apparently learnable.Soo… yeah that’s what this is about.If you missed it, I have a new company: www.alreadythere.com You can listen to this episode anywhere you listen to podcasts and its also on Youtube: Cheers,JonathanP.S. I updated the podcast are to make it more serious and business-like This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit

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44:57

I have a new company. It's weird.

The Unscheduled CEO ·

2025/10/21

I finally launched the thing i’ve been too scared to create for years.I hope some of you love this and some of you think it’s extremely pointless.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

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59:13

I promise this is making your life worse.

The Unscheduled CEO ·

2025/10/14

Something’s wrong. Something’s making us less happy, more lonely, feel less purpose… numbing us.You can also watch this weeks episode on Youtube if you don’t want to just listen.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

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78:10

Jake Knapp on Creativity, ADHD and Feeling Overwhelmed

The Unscheduled CEO ·

2025/10/07

It’s been years since Jake and I did an episode of a podcast together and this one goes DEEEEEEEP into our struggles with creativity, adhd and whatever else comes up!You can also watch this weeks episode on Youtube if you don’t want to just listen. 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

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50:50

I can't find balance. (Too Stressed or Too Bored)

The Unscheduled CEO ·

2025/09/30

This week I talk about my struggle finding balance between being too busy and too bored and not really finding a middle-ground.I also talk about a few other things:* Our huge collab with Pip Decks* Trying to simplify some of the mess i’ve created around me* A new drink is reviewed!You can also watch this weeks episode on Youtube if you don’t want to just listen.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit

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45:31

I'm starting to doubt myself...

The Unscheduled CEO ·

2025/09/23

In this episode I revisit my chronic motivation issues and ADHD-related problems.I also talk about a few other things: * AJ&Smart turning 15* My favourite non-alcoholic drinks (ranked!)* How i’m planning on dealing with my motivation issuesYou can also watch this weeks episode on Youtube if you don’t want to just listen.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

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97:43

Listen to my call with Sam Ovens

The Unscheduled CEO ·

2025/09/16

Hey! If you haven’t heard yet: The Unscheduled CEO podcast is now on an every Tuesday schedule…. till I get sick of doing it. This Tuesday is a special one because I’m chatting with someone who’s influenced my life in more ways than I can count: Sam Ovens.He’s the CEO of the inanely successful Skool.com, which has over 17 million users, and ran one of the first and most successful businesses in the online education space: Consulting.com.Sam is fascinating, he’s obsessive, he’s unconventional. This

en

35:57

56: Chapter 3 of this book will bend your mind!

The Unscheduled CEO ·

2025/09/09

Let's get ESOTERIC. Also: I got food poisoning, it was super fun!Watch on Youtube: 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

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