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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

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

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66:03

Forgetting this sales hack probably lost me millions

The Unscheduled CEO ·

2024/05/21

It’s Tuesday - let’s do this!This week’s episode is also available on YouTube if you want to watch some of the examples I talk about. (Just go to youtube and type in “Unscheduled CEO”)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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5:13

Voicenote: Happy Birthday to Pierce Brosnan

The Unscheduled CEO ·

2024/05/16

The most important day of the year is here!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

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57:28

Every millionaire I know uses the "Canvas Strategy"

The Unscheduled CEO ·

2024/05/14

It’s Tuesday - let’s do this!This week’s episode is also available on YouTube if you want to watch some of the examples I talk about. (Just go to youtube and type in “Unscheduled CEO”)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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10:50

Voicenote: Have you heard of the "Going First"...

The Unscheduled CEO ·

2024/05/09

It’s Thursday, here’s a Voicenote!When something comes to mind that I just can’t wait to put out on a Tuesday, i’ll make a voicenote and upload it!I won’t email you about these episodes, even if you’re on the Substack mailing list (I want to avoid spamming you), so please make sure you’re subscribed to The Unscheduled CEO podcast in any of the podcast apps.You can find the podcast in any of these places (and more!)Apple PodcastsSpotifyOn SubstackLemme know if you enjoy this mini format! You can

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37:42

The ONLY Time-Management Hack for Chaotic Entrepreneurs

The Unscheduled CEO ·

2024/05/07

It’s Tuesday - let’s do this!This week’s episode is also available on YouTube if you want to watch some of the examples I talk about. (Just go to youtube and type in “Unscheduled CEO”)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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9:48

Voicenote: Designing your workspace (so you get more...

The Unscheduled CEO ·

2024/05/02

This is a new mini-episode format called a Voicenote!When something comes to mind that I just can’t wait to put out on a Tuesday, i’ll make a voicenote and upload it!I won’t email you about these episodes, even if you’re on the Substack mailing list (I want to avoid spamming you), so please make sure you’re subscribed to The Unscheduled CEO podcast in any of the podcast apps.You can find the podcast in any of these places (and more!)Apple PodcastsSpotifyOn SubstackLemme know if you enjoy this mini

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44:50

Do this and get ONE NEW CLIENT every month

The Unscheduled CEO ·

2024/04/30

It’s Tuesday - let’s do this!This week’s episode is also available on YouTube if you want to watch some of the examples I talk about. (Just go to youtube and type in “Unscheduled CEO”)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 BlogApply for my LA business mastermind this summer —https://forms.gle/NKoeFdQH7NsMaKgy5To leave a comment go to howtobusiness/substack.com

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13:35

Voicenote: Why you never finish anything

The Unscheduled CEO ·

2024/04/25

This is a new mini-episode format called a Voicenote!When something comes to mind that I just can’t wait to put out on a Tuesday, i’ll make a voicenote and upload it!I won’t email you about these episodes after this one, even if you’re on the Substack mailing list (I want to avoid spamming you), so please make sure you’re subscribed to The Unscheduled CEO podcast in any of the podcast apps.You can find the podcast in any of these places (and more!)Apple PodcastsSpotifyOn SubstackLemme know if you

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26:39

The simple "travel hack" I use to become more successful

The Unscheduled CEO ·

2024/04/23

This is a super special episode because I’m announcing the very first in-person Unscheduled CEO event! Listen to the episode first, then fill out this form if you’re interested in applying to attend: https://forms.gle/NKoeFdQH7NsMaKgy5It’s gonna be a super fun, one-off, special weekend!In this episode:* How to spend time with more ambitious people* How to find more ambitious people* Why it can be lonely to be ambitious* How to spend time with people who have “made it” to where you want to be* The

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31:31

Our biggest product of 2023 FAILED and lost us...

The Unscheduled CEO ·

2024/04/16

We made $1,450,000 (yes that’s “million”!) LESS in 2023 than we did in 2022.Was it the economy?Nope (but of course everyone likes to make that excuse).Ah, must be our industry going through changes? Layoffs?Nope.Wait…. Online courses are dead, right??NO! It’s much more simple than that: We went against our “Zone of Genius” as a company. To leave a comment go to howtobusiness/substack.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus

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33:03

This tactic made us an extra $120,000 this week!

The Unscheduled CEO ·

2024/04/09

A small marketing experiment is set to bring us in an extra, unexpected $120,000 this week and it signals a change in strategy at AJ&Smart (credit to Dom and Laura for the idea and Rebecca and Ryan for executing it!)* Why we made LESS money in 2023 for the first time in AJ&Smart history* Why AJ&Smart not growing can mean the company simply becomes irrelevant* A marketing tactic we’ve been playing with that boosted our revenue by over 100k this week alone* Why so many entrepreneurs just never get

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