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
Dec 2, 2025 • 56min
Is working remote bad for your career? (I didn't want to post this)
Explore the paradox of remote work as those who create the tools often choose in-person collaboration. Discover how commuting stimulates social interactions, which are hindered by prolonged isolation at home. The conversation delves into the benefits for employers versus employees and the types of roles that succeed in remote settings. Jonathan challenges the convenience of remote work, emphasizing the importance of in-person connections for creativity and growth, all while advocating for a balanced, hybrid future.
10 snips
Nov 25, 2025 • 42min
Listen to this if you want to find your purpose in life
Feeling aimless despite past success, the host explores his lost business mojo and the search for purpose. He shares an enlightening moment that reignited his passion, discussing how expressing unique traits can reshape work and creativity. Ideas are woven into business strategies, showcasing innovative products while integrating personal attributes. The launch of a new platform serves as a protective space for his voice. Lastly, a Patreon is introduced, opening doors for exclusive content and community interaction.
12 snips
Nov 18, 2025 • 1h 6min
This LEAKED company handbook changed my life... (Seriously)
Discover the art of getting free help from hyper-successful individuals. Jonathan shares how most advice requests miss the mark, often becoming creepy or annoying. Learn why expressing gratitude and taking action matters in building connections. He reflects on his company's culture of passion-driven projects, influenced by Valve, and urges listeners to avoid making excuses that stifle opportunities. A light-hearted sparkling water review adds a humorous touch to the discussion, keeping it engaging!
7 snips
Nov 11, 2025 • 29min
The ONLY thing I'm focussing on to grow AJ&Smart in 2026
Jonathan shares his singular focus to expand his business, AJ&Smart, aiming for 10,000 weekly listeners by March 2026. He reflects on how reaching past milestones halted his motivation and how ADHD drives his quest for excitement. The candid discussion reveals the podcast as a low-fidelity creative outlet, allowing for spontaneous ideas. Listeners are encouraged to share episodes and engage, all while maintaining the quirky tone he loves. Jonathan's journey underscores the balance between growth and staying true to his unique style.
12 snips
Nov 4, 2025 • 1h 5min
Let's talk about how much I get paid
In a captivating discussion, Jonathan reveals his surprising day rate and the rationale behind it. He shares insights from his recent speaking engagement at a conference, where he embraced an improvised style, earning mixed reactions. Focusing on the concept of leverage, he dissects how speaking engagements compare to other revenue-generating activities. The conversation also delves into the mistakes people make in pursuing fame rather than meaningful leverage. Jonathan's refreshing perspective offers valuable advice on negotiating and maximizing one’s time.
Oct 28, 2025 • 57min
This personality trait 1000% decides your level of happiness and success
Dive into the fascinating trait of openness, a strong predictor of success and enjoyment in life. Discover how this characteristic can be measured and even increased through experiences. Jonathan contrasts cultural differences in openness and shares how it affects entrepreneurial success. He reflects on how open individuals foster creativity and innovation in dynamic environments. Plus, get insights on managing relationships with varying levels of openness and the exciting details about his new creative retreat.
9 snips
Oct 21, 2025 • 45min
I have a new company. It's weird.
Jonathan unveils his intriguing new venture, Already There, aimed at organizing experimental retreats. The centerpiece is Expedition 1, a device-free, five-day creative retreat in 2026 that prioritizes social connection and artistic exploration. He shares the evolution of the idea, the thrill of curation, and the stakes involved as it transitions from a small gathering to a major production. With a focus on design and purity, Jonathan encourages creative explorers to apply, while humorously reviewing a sparkling water. It's a wild ride into the unknown!
12 snips
Oct 14, 2025 • 59min
I promise this is making your life worse.
Dive into the fascinating discussion about how social media acts as an adult pacifier, numbing our emotions and distorting life choices. Discover how algorithms have transformed feeds into addictive slot machines. Jonathan argues that researching experiences can spoil their magic and suggests that reducing social media exposure can spark creativity. He shares surprising insights from a Stanford study on quitting social platforms and emphasizes the power of in-person connections to combat online discord.
26 snips
Oct 7, 2025 • 1h 18min
Jake Knapp on Creativity, ADHD and Feeling Overwhelmed
Jake Knapp, an author and designer renowned for co-creating the Design Sprint, dives into creativity and ADHD. He shares personal insights on feeling overwhelmed and the complexities of balancing life’s demands. Discussions include the effects of medication on creative processes, and how boredom can be more challenging than stress. They explore the balance between creative passion and practical work, emphasizing ongoing uncertainty in artistic pursuits. Their conversation encourages a thoughtful approach to overcoming barriers while remaining true to creative integrity.
12 snips
Sep 30, 2025 • 51min
I can't find balance. (Too Stressed or Too Bored)
Struggling to find balance between chaos and boredom, a revelation unfolds about creating one's own busy life. The host dives into the organized mess around him, sharing insightful stories about launching a new product and managing a major campaign with Pip Decks. He tackles home repairs, the stress of adult responsibilities, and the allure of live events that energize connection. A fizzy drink review adds flavor as he contrasts meaningful projects with monetary targets, wrapping up with a reflection on the importance of personal choice in a complex life.
