The Unscheduled CEO

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 idea
I 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 problem
Last 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 Berlin to be a filmmaker, not to run a business. And because the business was working so well, it was really hard to get out of that mode.
Blake’s point, over and over: there’s a state I can tap into where I do my best work. The in-person event we’d run the week before was the example. And the more time I spend in that state, the more successful the business will be.
Talking is my way in
Blake is a music producer, and he gave me an example I keep thinking about. A band puts themselves in the studio because the studio is where they create. Being in that room puts them in the headspace, and creating becomes natural there.
Which made me look differently at the AJ&Smart office. It’s beautiful and it’s fun, but it’s set up as a place where we make money, where I go in and check the numbers. So since that trip, the question has been: what situations can I put myself in where things just flow through me, no blockages, as natural as I can possibly be?
One clear answer: talking. That’s the actual reason this show exists as ONE unbroken, improvised take instead of an edited thing. If I bring any usefulness or strangeness to this business that’s hard to compete with, it’s that I can turn on a camera and talk for a long time, unscripted, and sometimes something interesting comes out of it.
There’s an exercise called morning pages, from The Artist’s Way by Julia Cameron. Every morning you fill 3 letter-size pages with stream of consciousness writing. Not a diary entry, just a brain dump. I did it for something like 7 years, I have piles and piles of notebooks. This show is my morning pages now, done out loud. The one twist is that I need the feeling that someone might get some use out of what I’m making, or I don’t feel like making it.
And it has a load of other benefits. New people find the companies through the show. People I’d never manage to stay in touch with (I’m not the best at networking) keep getting reminded I exist because episodes keep coming out. And it generates ideas for everything else. Last week’s video about Blake is what triggered the idea for the new workshop I’m building.
The €100 decision
Quick sidequest, because it belongs to the same thing. We were supposed to go back to Berlin yesterday and I didn’t feel like it, so we stayed. I know I have a flexible life because of the business I’ve built, but I’ve been around so many people mid-trip saying “we have to go now” when they don’t. If you’re loving something and dreading the return to your day to day, at least check the price of staying. Mine was €100. That was the entire cost of not breaking the flow.
And no, staying doesn’t contradict the routine-for-creation thing, because I’m still doing the routine. Same show, different location. Sometimes a new location is exactly what knocks the horse blinders off.
What I’m doing with all of this
I’m building my first personal development workshop. It’s born from the creative retreat I ran in February, 5 days, 5 nights, full digital detox, which a lot of you were actually at. I’m trying to find the compact version of that, something people could access more regularly, plus a new layer from the Blake stuff: how do you even figure out what you actually want to explore in the first place?
There’s a V1 of it done. I’ll test it on a couple of friends first, then in September on our guides in New York. (Guides are the top level of our facilitator business. A couple of you listen to this show, and yes, you’re our guinea pigs.)
That’s why the reading pile out here is The War of Art, Big Magic, The Surrender Experiment and The Second Mountain, plus my notes from February.
One more thing that fits. I saw The Odyssey at an IMAX here in Sweden on Saturday (not 70mm, in case you’re wondering). I’m not telling you it’s a great movie. What I love is watching someone get an insane, humongous thing out of their head and into reality. Long term, that’s the goal for me too: keep growing the business, sure, but make things that are creative, weird and risky. The February retreat was a first pinch of that. This show is another attempt at it. The business content has always been a bit of a Trojan horse to get you into this other stuff anyway.
If you’re in it right now
Maybe you have a switched-off version of yourself too. A thing you were before the business worked, parked because the serious mode was paying the bills.
2 small things to try this week. Notice which topics make you playful and which ones flip you into your own version of German mode. And find one slot in your week where you sit down, cast the lines, and see what shows up. You don’t need a podcast for it. 3 pages and a pen worked for me for 7 years.
Cheers, Jonathan
P.S. This is the cleaned-up version. The full episode has the forest, the rain, a very large ant, and me completely losing my train of thought after going to get my sunglasses... If you know one business owner who’d get something out of this, send it to them.
P.P.S. If you haven’t read The War of Art or Big Magic, please just read them. I have nothing to do with either of them, I just think you should.


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 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, Jonathan
P.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

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, Jonathan
P.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

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 away.
Not sell it. Give it. To anyone who’d take it. Or shut it down. I was talking to people about both options. My co-founder wanted to be bought out, and honestly, part of me wanted to be bought out too. There is a very real alternate timeline where I am not running this company today.
If you’ve never owned a business, that sentence sounds insane. Peak revenue! Great margins! What’s the problem?
If you have owned a business, you might already know exactly what the problem was. So let me give you the short version first, and then the whole story.
The nuggets (if you only read one section, read this one)
* The “held hostage in your own company” feeling is real, common, and almost nobody talks about it publicly. I now speak to founders constantly who describe the same thing: you walk into your own office and feel like you’re not wanted there. Like it’s not your company anymore. Like you’d have to ask permission to change anything.
* It’s almost never a revenue problem. It’s a hiring problem. Not “hiring is bad.” Hiring badly, for years, in ways that compound.
* Perks don’t buy goodwill. They buy expectations. We had a chef on Fridays, yoga twice a week, retreats, a basically unlimited tech budget. The result was not gratitude. It was “why don’t we have a chef every day?”
* “Hire when you need someone” is a spending instruction. The second I removed myself from hiring and told the team to hire whenever they felt they needed to, people hired the moment they felt slightly busy. At our peak of dysfunction, we had four employees managing one small office. My friend Sam Ovens was running a $12M company with nine people and a cleaner who came once a week.
* The way out was not “small team good, big team bad.” I want to be really clear on this, because it’s the lazy takeaway. Hiring is one of the only real forms of leverage a business owner has. The lesson is that there’s a right size and a right culture for you, and you probably can’t know it until you get it wrong.
* If you feel this way right now: it’s fixable. But it takes years, not quarters. And almost everyone I know who took the eject seat and sold tells me the same thing today: I wish I hadn’t done it.
Okay. The story. (You can also just watch the video if you don’t feel like reading)
My own personal utopia (and how I wrecked it)
I started AJ&Smart to build my own little utopia. A place where I could work on interesting things with people I actually wanted to be around. And for years, it was exactly that.
Then it worked too well. There was so much demand for what we did that I decided to see how far we could push it, and we scaled aggressively: from a couple of people adding one or two hires a year to 36 people. My co-founder went on a six-month sabbatical and came back to a different company. I want to be honest about the responsibility here. The negative vibes that followed were mine. I built them.
Here’s what daily life looked like at the “peak”:
Every single day, someone knocked on my office door with an irritation. A political fight with another employee. A complaint about a perk. Someone would come in, maybe pissed off, maybe sad, or flustered, tell me something going on in their family, and ask for a raise. I was in my late twenties. I had no idea how to handle that, so I just... gave people ad hoc raises. Then they’d tell their colleagues, and the colleagues would come knock on the door.
Friends hired friends. Sometimes that worked (it’s how we got Laura, who now runs Facilitator). Often it created factions. We occasionally hired someone who turned out to be, let’s say, creatively honest, or who’d just vanish for days.
And the perks. My theory at the time was: maybe people are unhappy because there aren’t enough perks. So: chef, yoga, retreats, gear, very little spending oversight, because we were making so much money anyway. And every perk generated a new complaint about the perk. The yoga time doesn’t suit me. Why only Fridays for the chef?
We hired coaches who told us we needed systems: weekly check-ins, quarterly career talks, one-on-ones. We did all of it. Then we ran the anonymous employee survey and the results were worse than the year before.
I walked into my own office feeling like the least welcome person in the building. Around that time I had coffee with the CEO of a much bigger Berlin company and asked her how it felt when she walked into her office. She said: “I feel like nobody wants me there.” She got out. Derek Sivers, one of my favorite people on the planet, got out too, and was so wrecked by the whole thing he seriously looked into legally changing his name and moving to another country to disappear.
That’s the club I was about to join.
The accidental control group
I got so irritated with the agency side of the business that I did something that, in hindsight, saved everything: I started a completely separate team, in a separate office, and kept it hermetically sealed from the mess. It was called AJ&Smart Digital Experiments (AJSDX), then Workshopper, and today it’s Facilitator.
And that little team felt... light. Positive. Fun. Everyone who works at AJ&Smart today (except Kyle, our bookkeeper who’s been here since day 1) came from that team.
That’s what finally showed me the truth. It wasn’t “companies are miserable.” It wasn’t “I’m not built for this.” The original culture was rotted, and I had rotted it. Given a clean start and everything I’d learned, I could build something completely different.
I tried the other classic escape hatch too, by the way: hire a CEO, move yourself to the board. What actually happens is you lose even more control and hate it even more. And a dark little secret nobody tells you: when you put people in positions of power in your business and step away, some of them will try to take it from you. “Give us the business or we take the clients” is a conversation more founders have had than will ever admit publicly. They might even try to force you to sell them equity “or else”. I’ve seen it all.
The reset
I’m slow and cautious by nature, so I waited for a signal. The signal arrived: one part of the business lost about €1.2 million in a single year. Either I go in and fix it, or I take it as the universe telling me the board-member experiment is over.
I came back as CEO properly. And over the following years we went from 28-ish people (post-Covid) down to around six people today. Three office spaces down to one. There was a chaotic co-founder buyout in the middle of it, and a new baby at home, and honestly the whole 2018 to 2022 stretch felt like a nonstop beating. I only feel like I’ve recovered the excitement in the last two years. You can literally watch the moment it turned, in the relaunch video that’s still on the AJ&Smart homepage. Which, btw I recorded about a week after having a MASSIVE panic attack on a work
And here’s the thing: today, the vibe is genuinely amazing. I love everyone on this team, we spend time together as actual friends, and the people who leave mostly leave to start their own companies. Some of the people who found me most annoying back in the bad years have contacted me since, after hiring their own first employees, to say: I get it now. I’m sorry. That pressure is invisible until you’ve carried it.
What we do differently now (the honest handbook)
The biggest single change is that we stopped lying. To candidates, to employees, and to ourselves, about what kind of company this is.
We now have an employee handbook (heavily inspired by, and in places directly stolen from, the Valve, Basecamp, and Panic handbooks. It says so in the handbook) whose entire job is to describe the company as it actually is, not as we wish it were. It includes lines like:
“Internal information dissemination is not our strong point at AJ&Smart, and it never will be. The only way to find out what’s going on is to be proactive about it.”
And an entire section called “What is AJ&Smart not good at?”: onboarding new people, formal career development, making remote people feel fully included, hiring anyone who needs traditional structure.
Founders read this and say “are you serious?” Yes. Because the years of misery came from hiring people with a pitch for a company that didn’t exist, then drowning in the gap between the pitch and reality. The honest handbook filters before the first day. Nobody arrives disappointed by the DNA, because we showed them the DNA up front.
I’ll share pieces of the handbook in an upcoming Thursday article. If you’re subscribed, it’ll land in your inbox.
If you’re in it right now
If you’re reading this and you feel held hostage inside your own business, even if it’s just you and three other people, I want to give you the version of this I wish someone had given me:
You are not obligated to keep running the company you accidentally built. And you don’t have to quit to escape it. There’s a third option, which is slower and harder and better: reset it, deliberately, into the company you’d actually want to walk into. It cost me years. It was worth every one of them.
And before you sell: talk to people who sold. Almost every single one tells me the same thing. The money’s nice. Having something you love doing is nicer.
Cheers, Jonathan
P.S. This week’s episode has the full, rambling, unedited version of this story, including several tangents I’ve mercifully spared you here. If you know a business owner who needs to hear it, send it to them. That’s genuinely the best way to help this show grow.
P.P.S A correction for the episode this week: I keep using dollars and euro interchangably but the actualy revenue number i’m trying to say is $6.3 million, I was saying “around 6.5” but I asked kyle after for the real number.


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!
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.
One thing that’s very clear is that it’s a completely different story depending on which country you’re from, and there’s a massive gulf between how entrepreneurs raise kids in the US vs the EU.Lots to talk about! Enjoy!
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