Jackson Lester is a civil engineer specialising in airport design and a rapper who makes music under the name Lester. Originally from Auckland, New Zealand, Jackson recently relocated to Vancouver, Canada, where he's joined a new band, picked up ice hockey, and is plotting to secretly...

Jackson is one of those friends where the conversation picks up exactly where it left off, no matter how many months or time zones sit between us.

We get into: what the default sound of a human would be if we didn't have words, why writing dark things you never release is still worth doing, the difference between a cliché and a truth that's been told so many times it lost its texture, using AI tools to create guitar riffs, the 1% change in the mirror that you never notice until you look back at old photos, why hugging a tree is only embarrassing if you let the label ruin the experience, and Jackson's hot take on the lottery.

"Are you satisfied with your life in its current form? And if not, why not?" — Jackson Lester

Find Jackson:

• SoundCloud: https://soundcloud.com/lester_jackson
• LinkedIn: https://www.linkedin.com/in/jackson-lester-5812ba15a/

Find Tay:

• Rejection Collection: https://rejectioncollection.vercel.app/
• Big Action | Tay's consulting company
• LinkedIn: https://www.linkedin.com/in/taypattison/
  

Books Mentioned:

• Project Hail Mary — Andy Weir
• We Need to Talk About Kevin — Lionel Shriver
• Atomic Habits — James Clear
  

People & Concepts Mentioned:

• Tom Scott — NZ rapper (Home Brew, Avantdale Bowling Club), Jackson's favourite artist; "the personal is universal"
• Kofi Stone — UK rapper, another of Jackson's current favourites
• Dexter and the News Agent — artist behind "With You," Jackson's song on repeat
• Doechii — rapper discussed; confirmed Tiny Desk performer
• Kendrick Lamar / Eminem / Joey Badass — early influences on Jackson's writing
• Rap Genius — website for breaking down rhyme schemes and lyrical structure
• Jody Blatchley ("Jodeo") — Tay's snowboard coach; unshakable confidence
• Jesse Itzler — entrepreneur/author; quarterly habits, Kevin's Rule (mini adventures), and the misogi concept
• Rejection therapy — collecting rejections as a practice; Tay's commitment to 5 asks per day
• The "personal is universal" — idea attributed to Tom Scott: specific stories resonate more than generic ones

  
  
  

Charlotte Rand is a creative matchmaker and the driving force behind the network at AUFI (Ask Us For Ideas, soon to be Ask Us For Introductions) — a company that connects brands with the right creative agencies to solve their biggest challenges. She's built relationships across every sector and stage of business, from Chanel to a startup selling vampire-themed tampons, and works with some of the most remarkable creative problem solvers in the world. Originally from New Hampshire, Charlotte has called London home for the past seven years.

Charlotte is one of those people I've been lucky enough to build a friendship with where we skipped the résumé exchange — we just liked each other as humans first. In this conversation, she shows up thoughtful and reflective, wrestling honestly with big questions about where the world is headed and what a meaningful life looks like.

We get into: why the most personal thing you can share is also the most universal, using yourself as a prism to split white light into something only you can make, the Cherokee parable of the two wolves and which one you're feeding right now, how a startup called Vampons turned menstrual care into the Liquid Death of tampons (and why the best opportunities are the ones you almost ignore), what the spiral teaches you that a straight line never could, the moment you realize a place hasn't changed but you have, why trust might be migrating from institutions back into our own bodies, the creative Renaissance that technology could unlock if we let it, and what's actually holding you back from the life you want.

"If you could do anything, what would you be doing? How close do you feel you are to doing that? And what's holding you back?"

Find Charlotte:

• AUFI (Ask Us For Ideas) | Creative matchmaker https://aufi.com/
• On LinkedIn - https://www.linkedin.com/in/charlotterand/
  

Find Tay:

• 10,000 Ideas (project sandbox mentioned in this episode)
• Futurecast: https://futurecast.fm
• Land Library: https://www.landlibrary.co/
• Nature Club: https://nature-club.co/
• Life-time Studio:

Books Mentioned:

• Braiding Sweetgrass — Robin Wall Kimmerer
  

People & Concepts Mentioned:

• Anna — the prism metaphor for individuality
• Rick Rubin — art as exploration vs. known outcomes
• Nelson Mandela — returning to a place unchanged to see how you've changed
• Thomas Breghiato / ATV (All-Terrain Vehicle) — LA-based creative collective
• Notpla — London-based material innovation company (seaweed-based materials)
• Vampons / Brie (founder) — vampire-themed sustainable period care startup
• iNaturalist — app for identifying plants and wildlife
• The Emerald (podcast) — mythic lens on modern life, individualism
• The two wolves — Cherokee parable about which inner wolf you feed
• The spiral vs. the straight line — progress as cyclical upward movement
• Santosh (yogic principle) — contentment and feeling you have enough
• Jesse — friend working in physical therapy, AI-proof profession
• Stoic philosophy — controlling what you can in uncertain times

Ed Thurlow is the founder of S33D.life — a distributed seed and story library turned living atlas of the world's ancient trees. What started ten years ago as an idea to use cryptocurrency to subsidize transparent hemp trade in Colombia has evolved into the Ancient Friends Network: a platform where you map ancient trees, mint NF Trees, share songs at banyans, and send whisper messages through nature. Based in Norfolk, UK, Ed is part gardener, part vibe coder, part pilgrim — building at the intersection of Web3, biodiversity, and the belief that every gardener is a futurist.

Ed and I share a mutual friend in Max, and this conversation had the energy of two people meeting for the first time but already speaking the same language. Ed showed up from a gray Norfolk spring with a decade of quiet conviction about a project most people would have abandoned — and the timing felt right, with vibe coding finally making it possible for him to build what he'd been dreaming.

We get into: why watching oak leaves come out after years of traveling felt like coming home, what happens when you stop working to survive and start trading the surplus of your passions, a ten-year journey from Bitcoin and hemp seeds in Colombia to mapping the world's oldest trees, why the biggest elephant ever recorded led to the oldest people on earth and a twinkle in their eyes that billionaires are missing, a tree radio where you can listen to every song shared at every banyan on the planet, sending whisper messages through ancient trees that your friend can only pick up by going into nature, the poetry tree at Equilibrio festival, predicting Max would appear in a top hat and a skirt within 30 seconds, why effectiveness beats efficiency when you're choosing what to build, and the difference between asking AI for answers and asking a tree.

Links:

• S33D.life: https://www.s33d.life/

Books Mentioned:

• The Faraway Tree — Enid Blyton

People & Concepts Mentioned:

• Jensen Huang (Nvidia CEO) — on redefining what intelligence means
• Alan Watts — being completely selfish as the most selfless act
• The San / Bushman communities — the oldest living group on earth
• The Ghost Elephants — Disney documentary about searching for giant elephants in Angola's highlands
• The Woodland Trust — UK ancient tree mapping organization
• What3Words — location tagging used for early tree mapping prototype
• Forest (app) — phone timer that grows a tree when you don't touch your screen
• Tāne Mahuta — one of the biggest trees in New Zealand
• The Buddha & Genghis Khan — Tay's dream tree visitors (playing poker)
• Bela — organizer of the poetry tree at Equilibrio festival in Portugal
• Max — mutual friend, top hat and skirt energy
• Tony Robbins — state first, then thoughts follow
• Bitcoin mining model — inspiration for the NF Tree minting mechanism
• Equilibrio — festival in Portugal
• Loveable / Codex / ChatGPT — tools Ed used in his vibe coding journey
• Andrew Robinson (previous guest) — left the "morning person" question
• Andy's morning person question premise: everybody is a morning person if you're five years old and it's Christmas

Andrew Robinson is a communication coach, endurance athlete, and the founder of The Grit Academy. Over the last 15 years, he's taught door-to-door sales, coached business owners, and worked with teenagers on the skills most adults never learn. He's placed top five in the world in 24-hour obstacle course racing, run all of New Zealand's Great Walks in 10 days, and recently cycled all of the Great Rides in a month. Through Tough Yarns, he's on a mission to encourage people to do difficult things and have meaningful conversations.

Andrew was the first person to really coach me. He drilled door-to-door sales methodology into me until I stopped intellectualizing and started doing. In this conversation, he shows up as himself. Honest, exhausted, in all senses of the word — and somehow full of gratitude.

We get into: why everyone thinks other people need communication skills but never themselves, the gap between telling people to ask for help and knowing how to hold space when they do, why an honest compliment is free energy, what it means to practice everything you've preached when it's your turn to need it, playing hide and seek with Jesus, and many more tangents.

Find Andrew: toughyarns.com | @toughyarns on Instagram

Projects:

• Tough Yarns: https://toughyarns.com
• Instagram: https://www.instagram.com/toughyarns
• The Grit Academy | Communication Coach
  
• Lasting Pages (book learning tool mentioned in this episode): https://lasting-pages.vercel.app

Books mentioned:

• Never Split the Difference — Chris Voss
• To Sell Is Human — Daniel Pink
• Man's Search for Meaning — Viktor Frankl
• The Subtle Art of Not Giving a F*ck — Mark Manson
• Everything Is F*cked — Mark Manson
• Atomic Habits — James Clear
  

People & concepts mentioned:

• Jordan Belfort — Straight Line Persuasion
• Robert Cialdini — Influence
• Daniel Pink — everybody is in sales
• David Whyte — the conversational nature of reality
• Ted Lasso — "Be a goldfish"
• IHC New Zealand
• The Dunning-Kruger effect
• Rejection therapy / Cringe Club

In this conversation, I have the pleasure of speaking with Erin Stafford. Erin is a full-time speaker, author of The Type A Trap and is an absolute sweetheart of a human being. She was a human-doing for a long time (and still often is). Currently, Erin helps people and organizations figure out how to perform at the highest level without destroying their health and relationships in the process. Erin has lived many lives to earn her perspective. She's been an advertising exec at MTV, a celebrity stylist in Hollywood, a jewelry designer, a fashion journalist, a news reporter, and the chief marketing officer of an $11 billion healthcare company that grew 27x through the pandemic. It was that last chapter — leading a team that scaled from 4 people to 75 while staffing 50,000 nurses across the country — that finally broke the pattern and forced her to confront her own achievement addiction. Now she gets on stages around the world to talk about what she's learned and how to live a life that not only looks good, but feels good too.

The conversation delves into personal reflections, the impact of tourism and gentrification, cultural integration and language, surfing culture and localism, emotional intelligence and self-reflection, experiences with anger and conflict, the egg cracking theory and personal growth, parenting and future aspirations, and emotional awareness and child rearing. We go into the topics of parenting and lifestyle changes, living a performative life, exploring desires and values, and the creation of ambient music and film. The discussion provides insights into the complexities of parenting, the performative nature of life, the exploration of desires and values, and the creative process of making ambient music and film. The complexity of human nature and personal relationships, exploring the blurred boundaries between personal and ideological aspects of life. It also touches on the process of film production and the pursuit of passion, as well as the importance of understanding personal energy and building healthy habits. The discussion concludes with reflections on planning for the future and the importance of personal connections.

Takeaways

• Openness and tolerance in a globalized world
• The value of critical thinking and kindness in parenting Parenting and lifestyle changes
• Living a performative life
• Exploring desires and values
• Ambient music and film creation Complexity of human nature
• Exploring personal relationships

Chapters

• 00:00 Emotional Awareness and Child Rearing
• 36:42 Parenting and Lifestyle Changes
• 47:20 Living a Performative Life
• 01:05:17 Exploring Desires and Values
• 01:12:06 Ambient Music and Film Creation
• 01:17:33 Personal vs. Ideological
• 01:23:12 Visual Storytelling
• 01:29:44 Transition to Filmmaking
• 01:36:08 Diet and Daily Routines
• 01:43:06 Planning for the Future

The conversation begins with a discussion about physical practices such as planking and the potential for new challenges. It then transitions into a deeper exploration of self-love and curiosity in relationships, highlighting the importance of setting boundaries and understanding introversion and extroversion. The conversation delves into the nuances of introversion and extroversion, exploring the differences in feelings and experiences in various social situations. It also touches on the impact of digital communication on introversion and extraversion, highlighting the challenges and dynamics of digital interaction. The conversation delves into the concept of balance and its connection to technology, as well as the role of libraries and collective knowledge in society. It explores the impact of technology on human behavior and the importance of maintaining a balance in the digital age. Additionally, it discusses the significance of libraries as spaces for collective knowledge and the preservation of indigenous wisdom. The conversation delves into the concept of nature's rights and the attribution of legal personages to natural entities. It explores the contrast between natural systems and man-made systems, highlighting the complexity and balance of nature compared to the limitations of human-created legal systems. Additionally, the discussion touches on podcasting aspirations and the idea of field notes as a format for sharing ongoing learning experiences. The conversation delves into the concept of planning mini adventures, embracing enthusiasm, and exploring the tension between anticipation and expectation. It highlights the value of planning and experiencing mini adventures, the importance of embracing enthusiasm in life, and the dynamic between anticipation and expectation in conversations and experiences.

Takeaways

• Self-love through slow pace
• Curiosity in relationships Introversion vs. Extroversion
• Digital Introversion vs. Digital Extraversion Balance is essential
• Technology and its impact on human behavior Nature's Rights
• Legal Systems vs. Natural Systems Planning mini adventures
• Embracing enthusiasm
• Exploring the tension between anticipation and expectation

Chapters

• 00:00 Connecting Through Physical Practices
• 41:52 Understanding Introversion and Extroversion
• 01:21:05 The Role of Libraries and Collective Knowledge
• 01:58:21 Nature's Rights and Legal Personages
• 02:12:39 Podcasting Aspirations and Field Notes
• 02:35:04 Mini Adventures and Planning
• 02:46:57 Embracing Enthusiasm
• 03:05:03 Tension Between Anticipation and Expectation