The Unscheduled CEO
Jonathan Courtney
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
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
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.
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.
10 snips
Aug 11, 2025 • 44min
Why I Quit LinkedIn Today
The host shares his bold decision to take a break from LinkedIn, highlighting the mental health effects of social media. He reflects on a recent trip to California, including organizing an innovative event in Silicon Valley. The discussion touches on embracing wellness through a gluten-free diet and holistic health approaches. There’s also a focus on the importance of learning from others and collaborating for success, as well as promoting a lifestyle with less social media for improved well-being.
6 snips
Jul 9, 2025 • 32min
Exactly how I use AI to get paying clients on LinkedIn (Voicenote)
Discover why most LinkedIn users are missing the mark in attracting clients despite high engagement. Learn the importance of authenticity in content creation and how personal experiences can lead to better connections. The discussion highlights the pitfalls of over-relying on AI, advocating for genuine communication instead. As professionals navigate hectic lives, the podcast emphasizes forming deeper, meaningful relationships over superficial interactions, ultimately showcasing how true engagement trumps artificial shortcuts in building a successful network.
18 snips
Jun 16, 2025 • 36min
A decision-making theory that changed my life + business
Life's big decisions can be daunting, but there's a better way to tackle them. The host encourages stepping beyond binary choices, urging listeners to explore a broader range of options. Personal stories highlight the complexities of navigating career and relationship dilemmas, advocating for creativity and self-awareness. By recognizing more alternatives, decision-making can become less stressful and more fulfilling. Embrace the art of redefining choices and escape the trap of false dilemmas!
