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
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!
9 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.
10 snips
Sep 23, 2025 • 46min
I'm starting to doubt myself...
In this engaging conversation, the host opens up about chronic self-doubt and the impact of ADHD on motivation. He celebrates 15 years of AJ&Smart while sharing his journey of reducing alcohol and ranks his favorite non-alcoholic sparkling drinks. The podcast also dives into the upcoming launch of Facilitator.com, discussing the challenges of leadership and the realities of entrepreneurship. With a relatable tone, he reassures listeners that struggling with motivation is a common experience.
Sep 16, 2025 • 1h 38min
Listen to my call with Sam Ovens
In this engaging discussion, Sam Ovens, CEO of Skool.com and former founder of Consulting.com, shares his unconventional journey to success. He emphasizes the importance of product development driven by user needs and founder involvement. Ovens challenges the idea that a strong social media presence is crucial for success, advocating instead for core business skills. He also reflects on navigating rapid growth, the pressures it brings, and the significance of authentic engagement in leadership. His insights are both eye-opening and actionable!
8 snips
Sep 9, 2025 • 36min
56: Chapter 3 of this book will bend your mind!
Dive into a mind-bending discussion about the challenges of creativity and entrepreneurship. The speaker candidly shares their battle with food poisoning and its impact on work, while emphasizing the importance of a well-designed workspace. Explore insights from 'The War of Art' and the dynamic flow of creative ideas, comparing them to living entities. Gain fresh perspectives on the recent Apple event and discover how engagement on social media can broaden your audience. This episode is rich with personal anecdotes and inspiration for any creative entrepreneur.
Sep 2, 2025 • 31min
What's a CEO actually supposed to focus on? + This is a Weekly Show now!
Exciting changes are afoot as the show embraces video and transitions to a weekly format! Insights from a recent entrepreneurial event shed light on the CEO's crucial role in business promotion. Effective communication is emphasized as key to success. Additionally, the importance of focusing on core goals and fostering meaningful connections for leadership is discussed. Listeners are encouraged to engage and participate in shaping future content!
13 snips
Aug 21, 2025 • 19min
You need a Sacred Space
Discover how to create a Sacred Space that transforms your work experience into something special. Learn how your environment influences creativity and mood, and the impact of meaningful items on productivity. The conversation dives deep into the importance of committing to risks, illustrating how taking leaps can accelerate personal and business growth. Embrace the idea of investing in your workspace to inspire innovation and elevate your entrepreneurial journey.
Aug 14, 2025 • 29min
I’m finally ready to tell you about “The Offset”
Explore the idea of a 'practicality offset' that champions integrating play into entrepreneurial life. The host shares personal journeys about rediscovering creativity, such as indulging in video games, highlighting its impact on growth. Listeners will appreciate the raw authenticity of unedited content, contrasting traditional polished productions. This open dialogue encourages maintaining childlike curiosity, crucial for both personal and professional innovation.
