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
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.
9 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!
10 snips
Jun 10, 2025 • 49min
I've learned an expensive lesson.
The host reflects on six years of costly experiments to make his business scalable, revealing 99% of them failed. He emphasizes the vital role of a CEO in defining business direction and the balance between collaboration and leadership. Personal anecdotes highlight the challenges of trusting others in operations and the pitfalls of relying on consultants. The discussion wraps up with updates on new initiatives and a light-hearted farewell, reminding listeners of available courses and training.
9 snips
Jun 2, 2025 • 50min
My new funnel made $100K in the first hour
Discover the thrill of launching a sales funnel that raked in over $220K in just three days! Learn how to craft compelling hooks that resonate with your audience, especially in the consulting realm. Dive into the strategic planning behind effective sales systems and the teamwork that drives success. The discussion also unpacks the challenges faced during the funnel launch and the importance of ongoing optimization for maximum impact. Get ready to transform your approach to marketing!
29 snips
May 22, 2025 • 1h 27min
The AI tools i'm actually using daily
Dive into the exciting world of AI tools in business! Discover Super Whisper, a game-changer that transforms your spoken thoughts into polished communications. Hear anecdotes that blend humor with practical applications, making AI feel accessible. Explore how automation tools like N8N streamline workflows in sales and enhance productivity. Learn about managing AI memories for better relevance and the balance between human creativity and automation. Join the conversation about fostering a community around practical AI uses!
8 snips
May 12, 2025 • 33min
Ok, i'm finally worried about AI. Here's my plan.
After a week in San Francisco, the realization hits: businesses that ignore AI will become irrelevant in 1-2 years. With just a few AI tools, productivity can skyrocket, making a small team operate like a much larger agency. The urgency to integrate AI isn’t just about efficiency - it’s about gaining an unfair advantage. Plus, industry shifts are evident, as even major companies seek employees fluent in AI tools. Embracing this transformation while maintaining human connection is key to thriving in the evolving landscape.
14 snips
Apr 24, 2025 • 46min
My weird hack for setting financial goals.
Join a journey through creative financing, as returning from Japan sparks financial insights. Explore a wealth mindset, emphasizing high-cost mentors and immediate gains. Discover personal spending philosophies that prioritize experiences over material goods. Dive into innovative ways to earn income without long struggles and rethink money in the entrepreneurial landscape. Plus, an invitation to a vibrant summer camp event awaits those eager to connect and grow.
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.
