
The Unscheduled CEO
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/ howtobusiness.substack.com
Latest episodes

9 snips
Mar 24, 2025 • 30min
Undiagnosed ADHD Was Ruining My Life
Discover a personal journey from disbelief to acceptance of ADHD as a real challenge. The speaker shares transformative insights after being diagnosed, emphasizing how medication has changed their focus and social interactions. They also tackle the common myths surrounding ADHD and reflect on the difference between viewing it as a superpower versus a legitimate condition. It’s an eye-opening discussion that sheds light on the realities of living with ADHD.

8 snips
Mar 4, 2025 • 48min
Listen to my call with Jason Fried
In this engaging chat, Jason Fried, CEO of Basecamp, delves into the complexities of maintaining motivation in entrepreneurship. He discusses the need for genuine breaks to gain clarity and rekindle passion for work. Jason shares insights on evolving perspectives, the thrill of continuous innovation, and the importance of a cohesive brand identity amidst growth. They also touch upon personal experiences with medication that enhance focus, adding a unique twist to the conversation. This raw and candid dialogue is sure to resonate with fellow entrepreneurs!

8 snips
Feb 26, 2025 • 22min
The Stupid Habit That’s Sabotaging My Business Success
In this intriguing discussion, the host shares personal struggles with motivation and decisiveness after therapy. The importance of taking proactive steps in business is emphasized, as waiting for the perfect moment often leads to missed opportunities. Personal anecdotes illustrate how indecisiveness can hinder growth and productivity. The conversation with a business coach further reinforces the need for confident decision-making to overcome challenges and achieve success.

13 snips
Jan 11, 2025 • 39min
How to make work feel like play
Dive into a spontaneous journey where creativity meets podcasting, sparked by a new synthesizer! Rediscover the balance between artistic passion and entrepreneurial duties, reigniting your creative roots. Shift gears from business travel to inspiring adventures, with Japan on the horizon. A candid reflection on how chronic stress impacts work-life harmony underscores the need for rejuvenating pursuits. Excitement brews for future projects, as the speaker embraces new energy and expresses gratitude for the audience's support.

Oct 11, 2024 • 52min
Why relaunching AJ&Smart drove me a little mad
The relaunch of AJ&Smart was a rollercoaster filled with emotional highs and lows. The speaker shares their struggles, likening the experience to pushing a heavy rock uphill while navigating high expectations for a major event. They highlight creative challenges in project management, particularly while developing a book on meetings. With a new office on the horizon, they grapple with the balance between perfection and playfulness. Ultimately, it’s a testament to teamwork and the necessity of embracing both ambition and creativity.

Aug 15, 2024 • 1h 4min
Rediscovering creativity and joy in my work
Hey friends!Just got back from a life-changing few weeks in California and wanted to update you all. This is a long episode, but I think it’s an important one.Cheers and love,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com

Jun 4, 2024 • 10min
Goodbye, for now (+ Summer Mastermind update)
Exploring decision to take a break, company direction changes, announcement of mastermind event in LA, and recommendation of valuable content creator Alex Hermose.

May 28, 2024 • 20min
You don't need to find your "purpose" to make your first million
The podcast discusses the importance of practical strategies over purpose-driven narratives in entrepreneurship. It emphasizes seeking advice from relatable business figures, implementing efficient organizational systems, and focusing on tangible goals to achieve success. The speaker also shares insights on transitioning from a consultant to making the first million, highlighting the significance of actionable advice and personal reflections on maintaining consistency.

May 23, 2024 • 9min
Voicenote: I'm feeling a little overwhelmed...
Exploring the speaker's intense workload, balancing work and personal life, navigating the highs and lows of entrepreneurship, and reflecting on upcoming projects with colleague Laura while expressing excitement and overwhelm.

24 snips
May 21, 2024 • 1h 6min
Forgetting this sales hack probably lost me millions
Discover how a unique perspective can revolutionize sales strategies, explore the casual insights of a CEO, navigate challenges in event facilitation, learn about consumer status symbols, and enhance sales through prestige marketing strategies. Delve into the psychology of status symbols in purchasing decisions and redefine value in work.
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