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 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
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
Episodes
Mentioned books
19 snips
Mar 25, 2026 • 59min
AI is making CEOs delusional
A take on why AI flattery can make executives overconfident and distracted. Short segments explore viral AI behavior, research linking chatbots to inflated self-assessment, and how RLHF fuels addictive praise. Conversations focus on AI speeding execution but worsening prioritization, causing lots of non-revenue projects. A reminder that traditional traffic, conversions, and profit signals still matter.
Mar 10, 2026 • 33min
I finally faced my biggest fear (it's haunted me for 30 years)
A comedian recounts finally confronting a 30-year phobia tied to sedation and an endoscope procedure. He traces a long history of anxiety, therapy breakthroughs, medication trials, and lifestyle shifts that helped. There is a playful sparkling water taste test and a preview of upcoming facilitation and training plans.
Mar 1, 2026 • 46min
What happened at my experimental creative retreat...
A founder recounts running a mystery, device-free creative retreat designed for wandering and discovery. He describes emergent facilitation, intense participant selection, and rooms full of painting, music, and models. Operational risks, funding realities, and plans to train facilitators are discussed. The retreat’s personal impact and renewed phone boundaries are highlighted.
Feb 17, 2026 • 35min
Oops, I went VIRAL...
A week of sudden online fame with a 50k YouTube surge and one viral X post. Using Claude AI tools to whip up fast marketing and ship product updates in a day. Reflections on momentum, the CEO duty to promote, and balancing building with marketing. Personal anecdotes about streaks, clarity-finding pivots, and practical negotiation and mindset tips.
29 snips
Feb 10, 2026 • 1h 9min
My new $20,000 marketing funnel was completely built by AI...
A rapid-build marketing funnel created almost entirely with AI, cut from six weeks and €20,000 to a few hours and pocket change. The host explains the AI tools and data sources that powered the quiz, plus a live walkthrough of flow, email capture, and integrations. There are candid stories about a Fiverr failure, security and regional concerns, and why reliability still beats flashy talent.
5 snips
Feb 3, 2026 • 57min
Getting clients: Easy Mode vs Hard Mode
A founder’s origin story about pitching, landing that first client, and turning a project into a company. How location, coworking and events created referral snowballs. A clear contrast between ‘easy mode’ local networking and ‘hard mode’ online outbound. Why founders must promote, teach, and run events to surface customers. Honest talk about anxiety, energy, and planning in-person retreats.
Jan 27, 2026 • 51min
I embarrassed myself in front of 3,500 people
A candid dive into handling harsh online feedback, trolls, and the psychology behind hate-listening. A recount of a chaotic webinar that turned into a five-and-a-half hour marathon and why pivoting saved the event. Reflections on self-doubt, treating attendees with respect, and clearing out entitled listeners to find a real audience.
7 snips
Jan 20, 2026 • 56min
I finally found the ULTIMATE AI use-case!
Explore the excitement surrounding a groundbreaking AI tool that promises to revolutionize productivity. Discover how AI can make small teams operate like giants and automate complex tasks like sales calls and SEO work. Hear about the transformation that occurred when an intuitive agent-driven workflow was unlocked. Jonathan shares his journey of building websites and generating style guides in minutes, while also addressing the importance of embracing technology to stay ahead in business.
8 snips
Jan 13, 2026 • 2h 13min
A chat with my biggest competitor: Chad Littlefield
Chad Littlefield, a creative entrepreneur and author, dives into fascinating discussions about his 'Contribution Method,' designed to elevate audience engagement at events. He shares insights on the resurgence of in-person gatherings and the quirky decision to ditch smartphones for a more genuine connection. The impact of AI on jobs is also explored, with Chad framing it as a tool for creativity rather than a threat. Together with Jonathan, they ponder the value of reflection, learning, and the transformative power of meaningful conversations.
10 snips
Jan 6, 2026 • 51min
My plan to make millions while having fun in 2026
Jonathan returns with a vibrant plan for 2026, emphasizing creativity and balance. He shares humorous anecdotes from his chaotic post-holiday return and his innovative ideas for low-obligation holiday traditions. Diving into the concept of agency, he encourages rethinking obligations and highlights how this mindset nurtures optimism. With exciting announcements about a creative digital detox retreat and weekly creative days, he balances business with personal growth. Plus, he draws inspiration from the game design of Zelda: Tears of the Kingdom while expressing deep gratitude to listeners.
