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The Unscheduled CEO

The Unscheduled CEO

By: Jonathan Courtney
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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.comJonathan Courtney Art Economics
Episodes
  • How I get my best ideas (my creative routine)

    How I get my best ideas (my creative routine)
    Jul 28 2026
    The written version of this week’s episode. The podcast is the full, unedited, chaotic version. This is the good bits, organised by taking the transcript and having an AI tool clean it up. HEY!I was supposed to fly back to Berlin yesterday.Instead I’m sitting on the ground in a forest in Sweden, recording this week’s episode on AirPods and a laptop camera. Changing my flight was quoted at €15, then the Eurowings website broke, so booking a whole new one cost €100. I paid it, because I didn’t feel like leaving yet.I wasn’t going to record at all this week. The show is called Unscheduled, I can do it whenever the hell I want, and nobody would have noticed a skipped Tuesday. But I was sitting there rereading The War of Art, and I caught myself asking: why the f**k am I recording this episode anyway?The answer turned into the episode. And I think it applies to your business as much as it does to my podcast.The nuggets (if you only read one section, read this one)* Ideas behave like fish: you can’t summon them, you can only be out on the water when they show up. This is Rick Rubin’s framing and I’m stealing it openly. The fisherman casts lines for a chance to catch something. The fish might be there either way, but if you’re not out there, you catch nothing.* A dedicated practice matters just as much for making money as it does for making art. You have to be creative to figure out how to generate revenue. It’s the same muscle, and it responds to the same routine.* If talking is how you think, build your outlet around talking. This show is one unbroken, improvised take because talking is my way of getting ideas out. Your version might be writing or walking. Find it, then give it a slot.* Your workspace trains your brain. A band walks into a studio and creating becomes natural, because the studio is where they create. My office is set up as a place where I go to check our numbers. Worth noticing what your space tells you to do.* The content you make for other people doubles as infrastructure for yourself. This podcast is my brain dump, my idea generator, and my way of staying in touch with people without networking. Last week’s video handed me the idea for a whole new workshop.* If you’re loving a trip, check what staying actually costs before assuming you have to leave. Mine cost €100. Most people never even look.Okay. The story.The fisherman ideaI have a few books with me in Sweden but the 2 that I kept rechecking were my classics: The War of Art, and Big Magic by Elizabeth Gilbert. If you listen to this show you’ll know I bang on about both of them. They circle the same concept, which is that ideas come from somewhere else, and if you’re in the right headspace you become a kind of antenna that can receive them.Whether you believe that or not doesn’t matter, and I don’t even know if I believe it myself. It’s a useful metaphor because you can experience it. Paul McCartney says the entire melody of Yesterday appeared in his mind in one go. Chris Martin says the same kind of thing all the time. Writers say it, filmmakers say it: I was just driving, and boom, the idea arrived.Rick Rubin has my favourite version of it. You’re a fisherman out at sea, casting lines into the water for a chance to catch something. That’s why writers sit at the desk from 10am until 1pm every day no matter what. They’re keeping the lines in the water.And that’s why I turned the camera on today. I’ve been doing this show for almost a year now, since September, and most episodes have no specific topic when I start. Sitting down on a Monday and pressing record is me casting the lines.I’ve felt this myself. When I was in a band and in the practice of songwriting, the songs just came. When I was writing scripts regularly in college, the film ideas flowed. Your antenna becomes more sensitive to the thing you keep showing up for.The mustard jumper problemLast week I told you about spending 2 days with my mentor Blake, so here’s the short version if you missed it. I went in with the goal of getting the company to 10 million a year. We were at six. By the end of the 2 days I realised I didn’t want that at all.What Blake actually did was watch me. In San Diego I was in a great mood, excited about buying a mustard coloured jumper in a tourist surf shop, telling him how much I loved every coffee shop we walked into. Then we’d sit down to talk about the business and he’d say: whoa, your entire vibe just changed. More serious, more closed off, kind of practised and strange. He kept saying GERMAN.When I talked about my relationship with my now fiancée, he said that’s the real version of you speaking. When I talked about the 10 million, it was the other one.We dug into it and found the uncomfortable bit: to make AJ&Smart and Facilitator work as well as they did, I’d more or less stopped using my creativity. Like a lot of entrepreneurs, I was a creative first. I was in a band. I moved to...
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    32 mins
  • Why Do Rich People Keep Making Content?

    Why Do Rich People Keep Making Content?
    Jul 21 2026
    The written version of this week’s episode. The podcast is the full, unedited, chaotic version, this is just the rundown of what we talked about, cleaned up from the transcript with an AI tool. [Spotify / Apple / YouTube]Hey,This week it’s me and Eli in the studio, plus my daughter hanging out in the background because it’s summer holidays, plus a fire alarm inspection, plus plumbers on the way. Classic Unscheduled recording conditions.It’s a hangout episode, but two proper threads came out of it: why wealthy people keep making content when they obviously don’t need to, and why adding a few thousand a month with a simple service business is easier than people think.Anyway, here’s what we talked about in the episode:We react to last week’s broken audio: Someone in the comments pointed out that I constantly complained about Laura and Eli making chair noises, and then I went and played background music so loud that it drowned out several minutes of us reviewing a drink. We replay the damage on this episode. Eli’s defence is that the music was so loud in his headphones he assumed I was just vibing extremely hard. This is what completely unedited gets you.Why rich people keep making content: It’s under every Alex Hormozi video: “why is this guy still making YouTube videos if he’s basically a billionaire?” The standard answer, “I want to help people”, mostly hides the truth. The real reasons: promoting the business is part of a CEO’s actual job, a lot of people (especially Americans, where the appetite for wealth is basically infinite) just want more, and past a certain point you’re doing it to feel useful and stay relevant rather than fade out. I’d respect people more if they just said that.An audience buys you optionality: This is the part I care about most for Unscheduled. If we keep bringing together like-minded entrepreneurs every week, we’re never locked into one business: we could run a creative retreat one year, open a video game arcade the next. A side effect I didn’t plan for: the more I do this show, the more interesting rooms I get invited into, like the two hours I spent on Greg Isenberg’s livestream on Thursday. Greg is the perfect example of all of this, he was already very successful when I met him, started the Startup Ideas podcast anyway, and it’s now one of the biggest AI shows on YouTube.The six-week hypothetical I’m never filming: Give me 30 freelancers for six weeks and I reckon I could get them making an extra $3,500 a month in profit with dead simple service businesses. Examples from the episode: helping local businesses like the Tyre King (a guy who comes to your building and swaps your tyres, we hire him all the time) show up in Google and the AI tools, for 150 a month, half of what he makes on one job. Designing and running company offsites, because an HR person is googling exactly that every minute and mostly finding crap. Building a lead-gen quiz like the facilitator.com one for a €500 one-time fee. It is NOT rocket science.Your competition is f*****g lazy: Someone pitched me this week in German, when every trace of me on the internet is in English. Someone else opened with obvious AI slop, and in my mind that person is blacklisted, because lazy outreach means lazy work. My split: use AI for the research, the strategy, the list of who to contact and what their problems are, then write the email yourself, click their website, watch their videos, maybe record a quick Loom. Ten extra minutes of effort puts you ahead of basically everyone, because the people you’re competing against will not do it.Revisiting the coaches video: We replay a piece of “I spent $600k on coaches so you don’t have to”, the Blake La Grange part. We paid Blake $100K to map the journey to $10 million, and by the end of day one he was telling me I didn’t seem like the person who even wanted a $6.3 million company, that I seemed more like an artist. I’d been waiting for someone to give me permission to say that. If your business works fine but you secretly don’t like it much, go watch that one.Where the show is at: Honest goal check: 10,000 weekly listeners by mid-September doesn’t feel realistic if we’re only counting the podcast. YouTube’s last 28 days: 11K views, almost 7K more than usual, and last week’s episode is at around 2,000 listens across YouTube and Spotify so far. Maybe the better goal is a minimum per episode instead of chasing an average. It’s good to have goals.If you only listen to one stretch of the episode, make it the simple-business-ideas one in the middle.Cheers, JonathanP.S. If you know one business owner who’d enjoy having this on in the background, send them this episode. (On the recording I said probably don’t send anyone this one. Ignore me.) 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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    1 hr and 10 mins
  • Being Weird is Your Only Unfair Advantage

    Being Weird is Your Only Unfair Advantage
    Jul 14 2026
    The written version of this week’s episode. The podcast is the full, unedited, occasionally unhinged version, this is just the rundown of what we talked about. Listen: [Spotify / Apple / YouTube]***BEFORE WE START I NEED TO TELL YOU ABOUT A VERY HILLARIOUS AUDIO ISSUE IN THIS EPISODE: Look guys, I dont listen to or watch these episodes before I hit publish so sometimes stuff is just… broken. This time around theres about 4 minutes where all you can hear is loud music and nothing else… im sorry :) **Hey,This week’s episode is more of a hangout vibe and less of a “learn something” one. Myself, Laura (who runs Facilitator.com) and Eli (our video guy) are hanging out in our new, overly complicated multicam studio setup at the AJ&Smart office, just talking about stuff. It’s classic Unscheduled.We did talk about some things that could be considered practical though, like we talked about how we’re currently using AI tools, we talked about how we deal with high monthly expenses AND we talked about how to sort of harness your weirdness as a competitive advantage.Anyway, here’s what we talked about in the episode:The new studio setup: What started as “let’s get Laura and Eli on camera” turned into a full multicam production with wires everywhere within about a week. Someone in the comments already asked if the background is AI generated, which I’m choosing to take as a compliment. If you normally just listen to the audio, this is one of the rare episodes where it’s worth having a look at the YouTube version.Laura, one month into being CEO of Facilitator: Her day to day is almost identical to before, the difference is that she owns the numbers now. It turns out owning the numbers is basically the whole job, in Germany it’s literally your legal obligation as the head of a company to keep the thing liquid, which is also why we won’t stop talking about money on a show with CEO in the name.The minus €450,000 months: There was a version of AJ&Smart where some months started at minus €450K, as in we had to make €450,000 that month just to get back to zero. It was a pressure cooker, but weirdly it was also some of the most fun and most cohesive the team has ever been. It forced us to get good, find mentors and build all the infrastructure we still run on today. Now that our costs are a fraction of that, it feels like we leveled up our video game characters so much that we’re back in the starter area. Small slow things like our Guides mastermind or this podcast, things the old “every product has to make €1M a year” rule would have killed on day one, actually get to exist now.A sparkling water review: Lacroix Razz Cranberry, Mango and Orange enter the ranking, and Orange takes third place behind Tangerine. Eli, who grew up in Colombia with actual mango trees at his school, confirms that the mango one tastes like almost nothing.How we’re actually using AI tools: Laura built one central context brain that pulls together everything she’s ever worked on with Claude and now uses the expensive model as the senior strategist and the cheaper models to execute. I use it to turn these unedited episodes into what you’re reading right now, plus research, lead magnets and a Monday morning growth report. Eli uses it for chapters, shorts and thumbnail ideas but still makes everything manually because the AI image output looks like s**t. The common pattern between the three of us is that the AI runs the machinery in the background and never touches the thing the customer actually sees.Harnessing your weirdness as a competitive advantage: The more AI standardizes everything, the more people seem to crave things that are obviously made by real humans. Clients are booking our trainings partly because we don’t pre-plan the agenda, and conference organizers are excited that the talk can never be repeated. Every listener who’s ever talked to Laura about this podcast praises exactly the things a growth consultant would tell us to cut: the mess, the tangents, the water reviews. It’s why this show will stay 100% unedited. Laura’s advice if you want to apply this in your own business is to stop taking the edges off yourself. The polish is the problem.If you only listen to one section of the episode, make it that last one.Cheers, JonathanP.S. My goal this year is to grow this show. If you know one business owner who’d enjoy having this on in the background, send them this episode. That’s the best way to help. 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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    1 hr and 40 mins
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