Join Will and his friend Pierre for a walking-and-talking podcast recorded against the stunning backdrop of Renosterveld in Cape Town.
In this free-flowing conversation, they explore creativity, strategy, and the value of embracing your uniqueness in a world increasingly dominated by AI.
Pierre shares his journey of compiling four years of daily letters into a book, his philosophy of “tracking desire” to guide the creative process, and why weirdness is often the most powerful business differentiator.
They discuss the pitfalls of competing solely on price, speed, or quality, and why identity and differentiation matter more than ever. Along the way, the two friends reflect on parenting, the fleeting nature of time with children, and the importance of taking ownership of your own agency.
From productivity systems using Apple Notes to the benefits of cold plunges and winter hiking crews, this episode blends business insights with personal reflections topped off with a few unexpected ostrich sightings.
Speaker Notes:
1. Opening & Setting the Scene (00:00 – 02:10)
• Greeting listeners; casual “walking and talking” intro.
• Location: Renosterveld with panoramic views towards Stellenbosch.
• Multi-tasking mindset: walking + podcast + errands.
2. Pierre’s Current Project (02:11 – 04:30)
• Compiling daily letters from 2020–2024 into a 365-entry book.
• Project is more editing and aligning than creating from scratch.
• Letters span pre-COVID, COVID, and post-COVID years.
3. Pierre’s Creative Process (04:31 – 07:10)
• Start with the desired future state; “tracking desire” like tracking an animal.
• Use emotion and gut instinct as creative compass.
• Embrace randomness and weirdness as creative fuel.
4. Three Ways to Win in Business (07:11 – 11:45)
• First: Rare and risky, but massively rewarding.
• Best: Often vague, can lead to “cheaper, faster, nicer” race to the bottom.
• Different: The most sustainable advantage; uniqueness removes direct competition.
• Link to “Category of One” concept.
5. AI & Human Uniqueness (11:46 – 14:30)
• AI will be faster and smarter but will never be “you.”
• Your wiring, experiences, and quirks are irreplaceable.
• Quote: “The only way to beat the agents is to use your agency.”
6. Parenting & Time Perspective (14:31 – 16:05)
• Shocking stat: By age 17, you’ve spent 90% of the time you’ll have with your kids.
• Encourages being present and intentional with time.
7. Pierre’s Background (16:06 – 18:40)
• Self-described “philosopher disguised as a strategist.”
• Focus: helping businesses and individuals find their differentiator.
• Meeting Will at Alchemy on the day Pierre was retrenched.
8. Systems for Capturing Ideas (18:41 – 22:30)
• Apple Notes with structured folders and smart tagging.
• Siri + Reminders to capture on-the-go ideas.
• Always-on capture to avoid losing sparks of inspiration.
9. Value Creation vs. Noise (22:31 – 24:00)
• Importance of delivering real value over social media posturing.
• Sermons, talks, and deadlines as productive cadence.
10. Cold Showers, Hiking, and Seasonal Crews (24:01 – 26:15)
• Will’s weekly Lion’s Head hikes: summer selfie crowd vs. winter hardcore crew.
• Pierre’s Clifton cold plunge tradition.
11. Closing Thoughts (26:16 – End)
• Biggest takeaway: Don’t fear your own agency.
• Make decisions and take responsibility before others (brands, AI, governments) do it for you.
• Wrap-up: coffee plans, shared photos of the walk and where to find more from both hosts.
Will https://www.linkedin.com/in/willgreen/
Pierre https://www.linkedin.com/in/pierredup/
Pierre’s Daily Letters: https://thisispierre.co/dailyletter