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
Apr 7, 2026 • 51min
The economy is crashing again. Here's what i'm doing...
The host explains how to steer a company through market turbulence with practical moves and mindset shifts. He traces a shift from agency work to scalable productized offerings and funnels. The conversation highlights learning from masterminds, extracting what works, and relaunching products for revenue bursts. Emphasis is on focused action, surrounding yourself with optimistic, high-agency people, and avoiding endless knowledge-shopping.
Apr 1, 2026 • 43min
The PERFECT marketing funnel for small businesses
A simple webinar-centered marketing system for turning strangers into clients. Details on filling webinars using email lists and multiple traffic sources. Discussion of running repeat webinars, writing strong hooks, and pitching effectively. Personal reflections on balancing CEO life, ADHD, and creative cycles. A light detour into video games and a sparkling water taste test.
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.
