The Unscheduled CEO

What nobody tells you about having kids as a CEO 30.06.2026 46min

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

Selling Was Hard Until I Understood This Concept 23.06.2026 36min

Guys… i’m BOILING over here.It’s the second heat wave of the summer here in Germany, 36°C in a country where almost nothing has air conditioning, so this is a short episode. But it’s a good one!Last week I talked about the ideal business model for a consultant. This week I want to talk about a concept that changed how I sell.For years I made selling harder than it needed to be, and then I understood one thing that made everything click. It’s a little unfair advantage hack that I rarely hear anyone mention. I use it all the time, and when it’s used on me, it makes me more likely to buy.Btw last week’s episode looks like it’'ll be the first “non guest episode” to hit 10K listens, wohoo!Anyway… sales…It comes down to two things: speed and convenience.The thing I didn’t getI’m on both sides of this all day. As a CEO I’m constantly buying services. As the CEO of an agency I’m constantly selling them. And the thing that actually decides whether I hire someone is almost never that they were the best. It’s that they made it easy to start while I was still excited.In January I was looking for help with the SEO of facilitator.com. I ended up on one call with one company. Not because they were the best, I didn’t do any research. Because they were the first to reach out and they could jump on a call straight away. Then they said they’d go away and make a proposal. By the time they came back, I’d figured out how to do it myself. They didn’t get the job.Momentum is the whole gameHere’s the truth about CEOs. If you give them too much time to think, they’ve already moved on. The SEO thing was exciting to me for about a week. Then I was done.So when someone gets on a call with me at AJ&Smart, it’s never about a big proposal. It’s about the soonest possible starting point. Someone wants help with a funnel, I don’t say I’ll prepare a proposal and we’ll have another call. I say: when can we start? This thing starts with a two-day kickoff, and at the end you might not even need us. No retainer to decide, no contract to sign. We just start.That gives the other person the feeling that this can start now. Because I know they’ve got a million things going on. Right now this is a high priority. In two weeks it’s nothing.Be the Michelin chefA friend started a business this week and had a deal slipping. I told him: if you lose it, it won’t be the price or the service. It’ll be that the other CEO lost momentum. We’re so used to doing everything ourselves that if it takes you too long, we’ll just say f**k it and do it ourselves.Too many of you get on a call, list everything you can do, then go away to make a proposal, then come back, then make the client choose a package. You’re handing the client the job of figuring out what they want from you. You’re the service provider. Be the Michelin chef. Say: this is what I think you need, let’s just start here and see where we get to.Stop giving people homeworkA CEO asks me, “Do you know someone for SEO?” I say yes. Two weeks later: “Oh, they sent me a proposal, I haven’t looked at it yet.” That person gave them homework. A lot of entrepreneurial people have that now-or-never thing, and a long proposal is a task they’ll never get to.The best proposal anyone ever did for me closed a 100K deal in a Google doc, live, on the call. By the time we hung up, that was the deal. We started, I flew out, the paperwork happened in the background, and neither of us cared because we’d already begun.Stay disconnected from the moneyThe move is to say: I’m excited, I can do this, let’s start. This is roughly my price. If it works out, my finance person will sort the contract. I want the client talking about the project and the dates, not the contract. If you’re a one-person show, your partner or a family member handles that part so you can stay on full speed.And talk the price on the call. No jump scare in an email three days later. “Ballpark, around 15 to 20.” If you can’t say that on the fly, get better at running your business.That’s the concept. Speed and convenience. Once I understood it, selling stopped being the hard part. You don’t need a better script or better marketing. You need to stop making it a job for people to say yes to 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

If I Knew This At 20 I'd Have Retired By 30 16.06.2026 1h

Hey,this week I want to try something a little different with the pod: i’m adding an enhanced summary of the “main takeaway” of the episode for those of you who prefer to just get to the good stuff and skip the rest.Of course I still think you should listen to the full episode to get the context, or at least put it on in the background while you scan through this. But whatever way you like to consume my content, enjoy!So!Here it is:The problem I hadMost consultants sell exactly one thing, and it happens to be the most expensive, hardest-to-buy thing on the menu.It’s the lowest leverage thing too, meaning you have to put in a lot of time to get paid to do this… which takes away from being able to actually run your business. For me it was selling design work to clients. Meaning the more design work I did, the more I would get paid. It was a 1:1 relationship with time and money.Around 6 years in to my design career I learned that there was a completely differently way to approach running an agency, a completely different set of business models that I had no idea about… and honestly I wish I had known about them from the start because GODDAMN they changed everything for me.Let me show you the other things you could be selling.The three rungsEvery consulting business can be split into three offers.Done For You. You do the work. The client pays top dollar and gets your hands on their problem. This is where almost every consultant lives, and most of them never leave.Done With You. You don’t do the work. You teach their team to do it. Workshops, training, group coaching. Cheaper for the client, way more leveraged for you.Do It Yourself. Courses, books, content. The client never interacts with you at all. Cheapest rung, fully scalable.When AJ&Smart was a UX agency, Done For You was us running design sprints for clients. Done With You was teaching their teams to run sprints themselves. Do It Yourself became the Design Sprint Masterclass.The part nobody expectsDone With You ended up being the most lucrative tier for us.Here’s why. You train ten people at a company. Another team hears about it and wants the same thing. Then another. The training spreads inside the company in a way a one-off project never does. And the rungs feed each other: trainings generate sprint requests, sprints generate training requests.There’s also a second thing that happens once you have three rungs instead of one. On a huge number of our sales calls, when the price for the top tier is too high, we don’t lose the client. We move them down a rung. If you only sell Done For You, every call is all-or-nothing. With three rungs, “no” to one offer is “maybe” to another.“But my work is too custom to teach”I said this exact sentence for years. I was certain there was no Done With You version of UX design. Too subjective, too dependent on me being in the room.I was wrong, and if you’re thinking it right now, so are you.The goal is not to turn the client’s team into you. It’s to find one fragment of what you do that can be taught. Maybe it’s just how you run a kickoff. Maybe it’s one part of your process. That fragment is a product.And if you’re experienced, there’s a move most consultants never consider. You don’t only have to sell to clients. You can sell to you, ten years ago. There are people who would do anything to be where you are now, and teaching them is a whole second business. That’s where Facilitator.com came from.Stop selling your timeThe last piece. Once you have your rungs, price them as packages, not hours. No day rates, no itemized lists of what’s included. The moment you itemize, you invite people to negotiate you down line by line.A rule of thumb I picked up that’s stuck with me: one month in your group program should cost about the same as one hour alone with you. That gap is what makes the cheaper rungs feel like a deal and the expensive rung feel exclusive.Do this this week* Write your three rungs. One sentence each: what’s your Done For You, what could your Done With You be, what could your Do It Yourself be? Don’t build anything yet. Just name them.* Find the teachable fragment. Ask yourself what you do that feels boringly easy to you but looks like magic to clients. That’s your Done With You seed.* Add a down-sell to your next sales call. When someone balks at the price, instead of “no problem, bye,” try: “There’s another way to work with me. I can teach your team to do this themselves.”* Price by the rung. Top expensive, bottom cheap, and stop itemizing.You don’t have to build a course this month. You just have to stop being a business with one product, where that product is the single hardest thing on the menu to say yes to.Cheers, JonathanP.S. The book that flipped this switch for me on packaging and pricing is Built to Sell by John Warrillow. It’s a short read. Worth doing this week. 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 pushed myself too hard this time... 09.06.2026 1h 3min

My friends, I’m tired!After a long weekend camping with the family combined with a hospital visit… how do I still find the time to record a show? In this episode I talk about how I still get content out there even when I really don’t feel like 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

I Went Back to LinkedIn, It Was a Mistake (feat Jake Knapp!) 02.06.2026 1h 52min

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 Episode Will Make You Better At Sales TODAY 26.05.2026 1h 23min

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

I said no to $10 million... do I regret it? | EP #81 19.05.2026 1h 35min

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

My plan to make $1,000,000 with my side hustle | The Unscheduled CEO 80 12.05.2026 1h 8min

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.com

It's time for a change... | The Unscheduled CEO 79 05.05.2026 32min

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,JonathanGet notified when a new episode drops:https://unscheduledceo.comMy active companies:AJ&Smart: https://www.ajsmart.comFacilitator.com: https://www.facilitator.comStudio: https://ajsmart.com/studioPartners: https://ajsmart.com/partners 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

Voicenote: How I avoid burnout 28.04.2026 12min

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

I'm Lazy and Moody. Here's how I still get things done... 21.04.2026 49min

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, visit www.unscheduledceo.com

Do this and life gets 23% easier 14.04.2026 48min

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!JonathanSummer Camp Mastermind Tickets: https://ajsmart.com/summercampGet notified when a new episode drops:https://unscheduledceo.comMy active companies:AJ&Smart: https://www.ajsmart.comFacilitator.com: https://www.facilitator.comStudio: https://ajsmart.com/studioPartners: https://ajsmart.com/partners 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 economy is crashing again. Here's what i'm doing... 07.04.2026 51min

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/summercampGet notified when a new episode drops:https://unscheduledceo.comMy active companies: AJ&Smart: https://www.ajsmart.comFacilitator.com: https://www.facilitator.comStudio: https://ajsmart.com/studioPartners: https://ajsmart.com/partners 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 PERFECT marketing funnel for small businesses 01.04.2026 43min

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

AI is making CEOs delusional 25.03.2026 59min

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

I finally faced my biggest fear (it's haunted me for 30 years) 10.03.2026 33min

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

What happened at my experimental creative retreat... 01.03.2026 46min

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

Oops, I went VIRAL... 17.02.2026 35min

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

My new $20,000 marketing funnel was completely built by AI... 10.02.2026 1h 8min

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

Getting clients: Easy Mode vs Hard Mode 03.02.2026 57min

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