The Unscheduled CEO

Jonathan Courtney
  • 5.0 (7)
  • MANAGEMENT
  • UPDATED WEEKLY

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 by someone who's been running one for over 13 years. Jonathan Courtney is the CEO of AJ&Smart.com and Workshopper.com Got a question you want to be read out on air? Comment on the current episode here: https://howtobusiness.substack.com/ www.unscheduledceo.com

  1. 2H AGO

    Oops, I went VIRAL...

    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

    35 min

  2. FEB 10

    My new $20,000 marketing funnel was completely built by AI...

    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

    1h 9m
  3. Getting clients: Easy Mode vs Hard Mode

    FEB 3

    Getting clients: Easy Mode vs Hard Mode

    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

    57 min

  4. JAN 27

    I embarrassed myself in front of 3,500 people

    HEY LOVELY PEOPLE, This is a juicy episode all about how I deal with feedback, criticism and online trolls. It’s a spicy one. Don’t listen if you don’t want spice. 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

    51 min

  5. JAN 20

    I finally found the ULTIMATE AI use-case!

    Ok ok ok, it finally clicked for me after using a new, crazy tool. The AI hype makes sense. I haven’t been this pumped about technology in like… a decade? Let’s talk about it. You can join the webinar I mentioned is right here. 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

    56 min
  6. A chat with my biggest competitor: Chad Littlefield

    JAN 13

    A chat with my biggest competitor: Chad Littlefield

    Hey! What’s up? This week i’ve got the beautiful Chad Littlefield (my mortal enemy) and we chatted about: * The Contribution Method (and How to Stop Exhausting Yourself Running Events) * AI is Going to Expose That Most Jobs Were Never Real * Ditching the Smartphone (and Why It Actually Worked) * The Return of In-Person Gatherings (and Why You’re Betting Big on Them) * Spirituality, Meditation, and Listening to Something Bigger This episode was a mess audio-wise and there was a slight delay in our connection, but you’re not listening to this crap to transcend or some s**t right? 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

    2h 13m
  7. My plan to make millions while having fun in 2026

    JAN 6

    My plan to make millions while having fun in 2026

    IM BACK YOU READY? Yeah? Ok. In this episode I talk about * How to get what you want by understanding Agency * Other stuff 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

    51 min

  8. 12/16/2025

    An update on my ADHD journey

    Hey! We made it to the final Unscheduled CEO episode of 2025! PHEW! In this episode I talk about * Results of my 1 year ADHD medication experiment * My life-changing mindset going into 2026 * My favourite book of the year * How to make sure you stay bold in 2026 See you all next year. You can listen to this episode anywhere you listen to podcasts and its also on Youtube: https://youtu.be/vDRPov6g0Rk 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

    56 min
See All (69)

Ratings & Reviews

5
out of 5
7 Ratings

About

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 by someone who's been running one for over 13 years. Jonathan Courtney is the CEO of AJ&Smart.com and Workshopper.com Got a question you want to be read out on air? Comment on the current episode here: https://howtobusiness.substack.com/ www.unscheduledceo.com

Information

  • Creator
    Jonathan Courtney
  • Years Active
    2023 - 2026
  • Episodes
    69
  • Rating
    Explicit
  • Copyright
    © Jonathan Courtney
  • Show Website
    The Unscheduled CEO

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