Jonathan Courtney
The Unscheduled CEO
Close your eyes...Now imagine The Diary Of A CEO but without the interviews, without the production value, without editing and without any topics. Imagine if the host was just sitting by himself, talking about... nothing really? What's the guy's name? Steven? Yeah, imagine him just sitting there rambling incoherently for like an hour. Thats The Unscheduled CEO!!This podcast is hosted by Jonathan Courtney, a hairy, Irish, Business Man. ENJOY! www.unscheduledceo.com
Author
Jonathan Courtney
Category
Podcast website
Latest episode
Jul 7, 2026
Where to listen?
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Episodes
I Hated My Company So Much I Tried To Give It Away 07.07.2026 1:09:03
This is the written version of this week's episode. As always, the podcast is the full, unedited, occasionally unhinged version — this is the good bits, organised. Listen on [ Spotify / Apple / YouTube ]. Hey, So this is a crazy one: Between roughly 2018 and 2022, at the exact moment AJ&Smart hit its peak revenue (around $6 million revenue, with a 47% profit margin), I wanted to give the company a...
What nobody tells you about having kids as a CEO 30.06.2026 46:19
Hey what’s up! In this week’s episode of Unscheduled I talk about what it’s like to run a business while being a fairly involved father. It’s a very complicated and nuanced topic that gets a lot of people VERY angry on the internet. My hope for this episode is to speak to the reality of what it’s like raising kids as an entrepreneur from both my perspective and my entrepreneur-friends perspectives...
Selling Was Hard Until I Understood This Concept 23.06.2026 36:02
Guys… i’m BOILING over here. It’s the second heat wave of the summer here in Germany, 36°C in a country where almost nothing has air conditioning, so this is a short episode. But it’s a good one! Last week I talked about the ideal business model for a consultant. This week I want to talk about a concept that changed how I sell. For years I made selling harder than it needed to be, and then I under...
If I Knew This At 20 I'd Have Retired By 30 16.06.2026 1:00:31
Hey, this week I want to try something a little different with the pod: i’m adding an enhanced summary of the “main takeaway” of the episode for those of you who prefer to just get to the good stuff and skip the rest. Of course I still think you should listen to the full episode to get the context, or at least put it on in the background while you scan through this. But whatever way you like to co...
I pushed myself too hard this time... 09.06.2026 1:03:16
My friends, I’m tired! After a long weekend camping with the family combined with a hospital visit… how do I still find the time to record a show? In this episode I talk about how I still get content out there even when I really don’t feel like it. 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.unschedul...
I Went Back to LinkedIn, It Was a Mistake (feat Jake Knapp!) 02.06.2026 1:52:12
This week I sit down for a chat with my old friend Jake Knapp (the guy who wrote Sprint and lot’s of other great books!).We chat about the new Ferrari thing, AI, and then we realise that we both don’t know what the P in Chat GPT stands for…. 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.c...
This Episode Will Make You Better At Sales TODAY 26.05.2026 1:23:32
This is a pretty special episode with some very special guests! In this episode you will learn the absolute best way to improve your sales and marketing, and it’s NOT something you hear a lot of people talk about. Enjoy and let me know what you think! 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.unsche...
I said no to $10 million... do I regret it? | EP #81 19.05.2026 1:35:09
It’s Tuesday AGAIN???? This week talk about why I haven’t sold my company yet, whether I’m thinking about it and a huge offer I turned down. Hope you guys enjoy the show! Enjoy! 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 $1,000,000 with my side hustle | The Unscheduled CEO 80 12.05.2026 1:08:23
ITS TUESDAY! And the podcast has a new look and feel this week (if you watch on Youtube anyways!) This week I talk about the plan to get Unscheduled as a brand to its first million in revenue. It’s going to be a long road, but it’s exciting to start something new again! Oh, and you can write into the show now too (more on that in the episode).Enjoy! Jonathan This is a public episode. If you would...
It's time for a change... | The Unscheduled CEO 79 05.05.2026 32:09
Hey listeners! This week’s episode of unscheduled is about my new focus at AJ&Smart… or outside of it. Lot’s to discuss and lots more in the coming weeks! ENJOY! Cheers,Jonathan Get notified when a new episode drops: https://unscheduledceo.com My active companies: AJ&Smart: https://www.ajsmart.comFacilitator.com: https://www.facilitator.comStudio: https://ajsmart.com/studio Partners: https://ajsma...
Voicenote: How I avoid burnout 28.04.2026 12:16
Hey all, Not in the mood to do a full pod this week so I recorded this little voicenote for you on my drive home today. Hope it tickles some of you. 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'm Lazy and Moody. Here's how I still get things done... 21.04.2026 49:29
You guys know me by now. I’m a moody, inconsistent, chaotic motherfucker. But… I still get s**t done. A lot of s**t! Isn’t that weird? It’s even weird to me! Anyway, this episode is about how I actually manage to get myself to do stuff even though I barely know anybody lazier than me. Cheers and love,JonathanP.S. leave a comment so I know you’re paying attention you cuties!!!! This is a public epi...
Do this and life gets 23% easier 14.04.2026 48:43
Hey friends, I recorded a poddy about something I do that makes my life easier. A lot easier! Like… 23% easier i’d say. Enjoy! Jonathan Summer Camp Mastermind Tickets: https://ajsmart.com/summercamp Get notified when a new episode drops: https://unscheduledceo.com My active companies: AJ&Smart: https://www.ajsmart.comFacilitator.com: https://www.facilitator.comStudio: https://ajsmart.com/studio Pa...
The economy is crashing again. Here's what i'm doing... 07.04.2026 51:03
So the markets are turbulent again. Another recession? Who the hell knows! What I do know is that it’s STILL my job to make sure my company both survives and thrives through whatever happens. Here’s my plan to deal with it. Summer Camp Mastermind Tickets: https://ajsmart.com/summercamp Get notified when a new episode drops: https://unscheduledceo.com My active companies: AJ&Smart: https://www.ajsm...
The PERFECT marketing funnel for small businesses 01.04.2026 43:19
Hey! In this weeks episode of the Unscheduled CEO I show off my very simple system for turning strangers into clients. I also review some new water and talk about videogames. Oh, and I announced Summer Camp 2026 which you can get tickets to right here: https://ajsmart.com/summercamp This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes,...
AI is making CEOs delusional 25.03.2026 59:11
Hey friends! This week I talk about the biggest problem i’m seeing with CEO’s using AI tools. Hint: THEY’RE MAKING LESS MONEY BECAUSE OF IT. But it’s even worse then that, because while they make less money, they get more and more lost in the AI-HOLE. Listen or watch on Youtube for the full breakdown. This is a public episode. If you would like to discuss this with other subscribers or get access...
I finally faced my biggest fear (it's haunted me for 30 years) 10.03.2026 33:17
The title you’re reading isn’t an exaggeration: I’ve had a severe phobia for over 30 years and in many ways it’s controlled my life. After over 5 years of therapy and COUNTLESS other approaches, I finally faced it last week. This episode is about what happened. Oh and also I review a can of sparkling water. Thanks to everyone for listening to this absolutely useless nonsense. I love you all. Cheer...
What happened at my experimental creative retreat... 01.03.2026 46:29
Releasing an episode on a Sunday?? Let’s chat about our first ever Experimental Creative Retreat… 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
Oops, I went VIRAL... 17.02.2026 35:01
This was a BIG week, first I got 50k views on a Youtube video… then I had my FIRST viral tweet! The only question is: what will I do with my new found fame? Let’s find out! 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 new $20,000 marketing funnel was completely built by AI... 10.02.2026 1:08:50
I just built a new funnel that would have taken 6 weeks and $20,000 in a few hours. This isn’t hyper or exaggeration, this is where these tools are at right now. Uhhhmm… that’s what this weeks episode is about. 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...
Getting clients: Easy Mode vs Hard Mode 03.02.2026 57:13
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 27.01.2026 50:54
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.unsche...
I finally found the ULTIMATE AI use-case! 20.01.2026 56:29
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 oth...
A chat with my biggest competitor: Chad Littlefield 13.01.2026 2:12:44
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...
My plan to make millions while having fun in 2026 06.01.2026 51:22
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
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