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.com...
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.unscheduledceo.com...
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
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 like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo...
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://ajsmart.com/partners This is a public episode. If you would like to discuss this with other subsc...
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
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 episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visi...
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 Partners: https://ajsmart.com/partners This is a public episode. If you would like to discuss this w...
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.ajsmart.comFacilitator.com: https://www.facilitator.comStudio: https://ajsmart.com/studio Partners: ht...
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, visit www.unscheduledceo.com...
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 to bonus episodes, visit www.unscheduledceo.com...
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.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get ac...
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
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
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 get access to bonus episodes, visit www.unscheduledceo.com...
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
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...
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...
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 ou...
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...
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 2026 See you all next year. You can listen to this episode anywhere you listen to podcasts and its also on Youtube: https://youtu.be/vDRPov6g0Rk Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscriber...
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 relationships Chapters: 00:00 - Where do I know Blake La Grange from?03:07 - Why Blake’s conversat...
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,Jonathan P.S. I did a little office tour video you can watch right here. T...
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 ADH...
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,Jonathan P.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...
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,Jonathan P.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...
Jonathan Courtney delves into his experience speaking at the Why Oslo conference, where his unscripted, humorous approach and high day rate surprised many. He explains that his ability to dictate terms and earn significant income stems from strategically building "leverage" through his "tiny" podcast, which generates far more value than traditional speaking engagements. Courtney emphasizes prioritizing enjoyable, high-output activities and the power of confident negotiation, even sharing personal anecdotes about securing autonomy early in his career by simply asking for what he wanted and being willing to walk away.
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,Jonathan P.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.uns...
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
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
