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PODCAST

The Unscheduled CEO

Jonathan Courtney

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 management

All Episodes

31:18

What's a CEO actually supposed to focus on? + This is...

The Unscheduled CEO ·

2025/09/02

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

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18:38

You need a Sacred Space

The Unscheduled CEO ·

2025/08/21

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

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29:12

I’m finally ready to tell you about “The Offset”

The Unscheduled CEO ·

2025/08/14

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

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43:51

Why I Quit LinkedIn Today

The Unscheduled CEO ·

2025/08/11

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

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32:02

Exactly how I use AI to get paying clients on...

The Unscheduled CEO ·

2025/07/09

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

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35:56

A decision-making theory that changed my life + business

The Unscheduled CEO ·

2025/06/16

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

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49:14

I've learned an expensive lesson.

The Unscheduled CEO ·

2025/06/10

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 howtobusiness.substack.com

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50:03

My new funnel made $100K in the first hour

The Unscheduled CEO ·

2025/06/02

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

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87:01

The AI tools i'm actually using daily

The Unscheduled CEO ·

2025/05/22

HEY! Ok, I recorded another episode even though I keep saying i’m taking a break.It’s too exciting!!!!Today I had Alen, a business partner, on the podcast to talk about how we're actually using AI tools in our businesses. This was only the second time I've had a guest on the show, but I figured after my AI wake-up call episode, it made sense to dig deeper with someone who's been using this stuff way longer than me.Alen's been trying to get me interested in AI for months, and I kept ignoring him. I

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32:34

Ok, i'm finally worried about AI. Here's my plan.

The Unscheduled CEO ·

2025/05/12

Hey friends,I just got back from San Francisco, and holy s**t, I need to write this down before I forget the intensity of what I'm feeling right now.For the past year, I've been in the "AI is cool, but whatever" camp. I mean, I figured it would eventually matter, but not enough to reshape how I run my business today.That mindset is completely gone now. Like, completely.After a week of non-stop conversations with founders, watching demos, and seeing how businesses are actually using these tools, I'm

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46:29

My infinite money hack (...and how I got you to pay...

The Unscheduled CEO ·

2025/04/24

OOPSIE, i’m back early from my sabbatical…Imagine if you could pay for the life you wanted WITHOUT leaving it up to “let’s see how this year goes” or being constantly at the whims of the shaky economy?Well… listen to this!Summer Camp 2025 is SOLD OUT. Waiting list here: Join the Waitinglist.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com

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29:54

Undiagnosed ADHD Was Ruining My Life

The Unscheduled CEO ·

2025/03/24

I didn’t really want to believe that ADHD was making my life worse. I thought ADHD was a superpower… that it wasn’t really a “real” problem.I’m starting to think I was very VERY wrong, and that’s what this week’s episode is about.Summer Camp 2025 Info:* Coming to Summer Camp? Tickets are here!* Book a call with Laura from my team to see if Summer Camp 2025 is for you!* Sales close Friday 28th of MarchCheers and love,JonathanP.S. I’m not a doctor or a therapist. Do your own research. This is a public

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48:11

Listen to my call with Jason Fried

The Unscheduled CEO ·

2025/03/04

This is a call recording of Jason Fried, CEO of Basecamp, helping me out with some motivation issues I’ve been having. We didn’t know if we’d release it. It’s VERY raw and, of course, unedited.Here’s what we talk about:* Me losing some of my business “mojo” in recent years* Growing AJ&Smart to 10 million… or not* Why Jason thinks I need a real break from the business* A surprise reveal about some medication I’m testing out!Jason is the first-ever guest on this podcast And coincidentally, Jason was

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22:07

The Stupid Habit That’s Sabotaging My Business Success

The Unscheduled CEO ·

2025/02/26

Hey friends!Recorded this one in the car, posted without listening back so don’t know how bad it sounds.Comments—→ www.unscheduledceo.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com

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39:00

How to make work feel like play

The Unscheduled CEO ·

2025/01/11

Hey friends!It’s been a while, I wanted to say hey and tell you what i’m changing in 2025.Lot’s of news and new stuff. Comments—→ www.unscheduledceo.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com

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52:20

Why relaunching AJ&Smart drove me a little mad

The Unscheduled CEO ·

2024/10/11

Hey friends!Many of you have probably already seen and heard that last week we relaunched AJ&Smart.But what you don’t know is the process of getting there.It wasn’t easy. Comments—→ www.unscheduledceo.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com

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64:17

Rediscovering creativity and joy in my work

The Unscheduled CEO ·

2024/08/15

Hey friends!Just got back from a life-changing few weeks in California and wanted to update you all. This is a long episode, but I think it’s an important one.Cheers and love,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com

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9:30

Goodbye, for now (+ Summer Mastermind update)

The Unscheduled CEO ·

2024/06/04

This is the final episode of the podcast for the summer, the year, I don’t know! You’ll now find me occasionally co-hosting Greg Isenberg’s Startup Ideas Podcast, like here: Final call for the LA Mastermind here: https://forms.gle/NKPsKydaCfGFCdyZ8Thanks everyone! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com

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20:03

You don't need to find your "purpose" to make your...

The Unscheduled CEO ·

2024/05/28

It’s Tuesday - let’s do this!No Youtube this week.You can find the podcast in any of these places (and more!)Apple PodcastsSpotifyOn SubstackYou can comment by going to the How To Business Blog This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com

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9:26

Voicenote: I'm feeling a little overwhelmed...

The Unscheduled CEO ·

2024/05/23

Phew, it’s been busy!You can find the podcast in any of these places (and more!)Apple PodcastsSpotifyOn SubstackLemme know if you enjoy this mini format! You can comment by going to the How To Business Blog This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com

en

54 results

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