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
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.
9 snips
Dec 16, 2025 • 56min
An update on my ADHD journey
Dive into a transformative journey as the host shares insights from a year-long ADHD medication experiment. Discover how mindset shifts and encouraging friends can inspire bolder choices for 2026. Unpack the lessons from a favorite book that reframes life’s ambitions. Explore the tension between surrender and proactive change, along with nonchemical tools for focus and creativity. Plus, hear about the importance of letting creativity flow without the weight of skepticism. Lastly, get a fun ranking of sparkling water!
28 snips
Dec 9, 2025 • 1h 52min
Listen to a (very personal) call with my mentor...
Join Jonathan and his mentor Blake Lagrange, a creative force and former music/tech founder. They dive into the emotional aftermath of a business retreat panic attack, exploring why some live performances leave him feeling blue. Blake shares insights on transitioning between art and business, the power of intuition in decision-making, and the importance of stillness in nurturing creativity. They also discuss how life's detours can enrich one's creative journey and the role of personal loss in igniting new artistic passions.
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.
