The Unscheduled CEO

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 access to bonus episodes, visit www.unscheduledceo.com

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 BiggerThis 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

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

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 access to bonus episodes, visit www.unscheduledceo.com

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 so hard17:40 - Coaching with honesty, love & the pain of true feedback23:15 - When your business stops fitting you and who you are26:53 - The core moment that helped Blake understand me31:24 - The Squid Gods are making decisions for us35:40 - Finding a way to channel intuition on purpose39:44 - Everyone has intuition (but most people choose productivity instead )48:13 - How Blake knew it was time to leave his business54:35 - Finding your medium & seeing others live your potential1:04:17 - The Two-Mountain Life: Success vs Meaning1:11:10 - Prodigy, talent & why Jonathan’s using only 1%1:21:26 - Pressure & environments where Jonathan thrives1:26:28 - The feeling of actually doing the thing you’re talking about1:31:19 - Acting vs Delusion: Why doing the thing makes it real1:34:41 - A moment that changed Blake’s life1:44:50 - The call to create & resisting practicality1:45:48 - How to contact Blake (If you’re doing something interesting)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

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

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 medication…. which kinda worked… till it stopped working.BUT finally, F*****G FINALLY, all of that exploration has lead me to an “Aha Moment” which has started to bring back some of that energy and purpose I thought was maybe gone forever.That’s… basically what this episode is about.Hope you get something from this.Oh, I also launched a Patreon.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

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

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

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

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 www.unscheduledceo.com

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

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