Discover
The Unscheduled CEO
The Unscheduled CEO
Author: Jonathan Courtney
Subscribed: 31Played: 404Subscribe
Share
© Jonathan Courtney
Description
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
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
59 Episodes
Reverse
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
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 www.unscheduledceo.com
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
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 might be an episode worth watching on the Youtube channel if you have the time this week: Cheers,JonathanP.S. You can leave comments at www.unscheduledceo.com, I read every one of them 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
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
Hey everyone!Some big news in this week’s episode:* The Unscheduled CEO is back on Youtube, so if you prefer to watch and listen, you can do it right here!* I’ll no longer email you about episodes, so please subscribe either on Apple Podcasts, Spotify or Youtube if you want to keep up with the show. * The show is going to a weekly format (for an experimental 6 weeks). Episodes will land Tuesdays at 7PM PT/10AM CET* I’ll experiment with recording LIVE on Mondays. Still figuring out when exactly, but if you’re subscribed to my channel, you’ll see when i’m live.Let’s go!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,You need to design a Sacred Space to make work feel more special. Some weird audio issues in this episode… not sure why… :) * How to build a sacred workspace you actually love. Your environment shapes your creativity, your mood, and how seriously you take yourself.* I’ve always found that when you buy ahead of where you are. Whether it’s a bigger office, better tools, or just stuff that excites you, you naturally grow into it.* Being an entrepreneur is about taking leaps and committing—those little risks create the stakes that force you to figure it out and level up.Cheers,JonathanP.S. You can leave comments at www.unscheduledceo.com, I read every one of them 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 second episode in one week??This one’s pretty personal.* The Offset * Why my creative life suffered in my 20s and early 30s* How i’m bringing more play and creativity back into my lifeCheers,JonathanP.S. You can leave comments at www.unscheduledceo.com, I read every one of them 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
Heyyyyy,Today I decided to take a minimum 1-year break from LinkedIn. In this episode I talk about that!I also talk about:* My recent trip to California* Why I also quit instagram in 2020* I do a lot of accents* Other stuffCheers,JonathanP.S. You can leave comments at www.unscheduledceo.com, I read every one of them 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 everyone,A quick iPhone voicenote for you this week.I promise you that 99.9% of people using LinkedIn to grow their audience and get clients are doing it wrong. They might be getting engagement, but nobody’s reaching out to work with them, nobodies really making money.I am. Here’s how I do 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.unscheduledceo.com
Hey everyone,You know those big life decisions like when to quit a job, whether to buy a house or the painful “to stay or go” decision in relationships?These kinds of decisions rarely have a clear answer and can cause a massive dilemma. Here’s my take on how to make these decisions feel easier.Cheers,JonathanP.S. it’s www.unscheduledceo.com now! 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 everyone, For the last 6 years i’ve spent millions on experiments in the pursuit of making AJ&Smart more “scalable” and “sellable”.99% of them failed and we lost money and momentum.Here’s what I learned and why we’re growing again without scaling.Cheers,JonathanP.S. I’m back. 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 hey!As i’m recording this, a funnel I launched with my team on Wednesday has generated over 100 high-quality call bookings and over $220K in revenue. It’s only been 3 days since I switched it on.In this episode I talk about the behind-the-scenes of a brand new, hyper-successful funnel!You can see the funnel right here: book.facilitator.com A lot to unpack in this episode.Cheers,Jonathan P.S. Waiting list for Summer Camp: https://go.ajsmart.com/summer-camp 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























