The Pathless Path with Paul Millerd

By Paul MillerdBusiness Entrepreneurship Careers

The Pathless Path with Paul Millerd episodes

May 29, 2024#174 Agency Is A Skill — Cate Hall on leaving law for poker, developing agency, deterministic vs probabilistic economy, risk, burnout, asking dumb questions, defining ambition, seeking real feedback, and the surface area of luck
Cate seemed to be fully entrenched on the default path — she had graduated from Yale and became the Supreme Court advocate on her way to becoming a partner in her law firm. But she didn't want to live the lives of the people around her. She pivoted hard, you could almost hear car brakes squeaking as she made the turn, and over a year she became the number one female poker player in the world. She later started art and perfume companies and led operations at Avlea — a pandemic medicine company. One might think she's simply a superhuman, and what she did is beyond the grasp of mere mortals, but Cate claims that agency is learnable and joins the podcast to tell us how.
🎥🍿 YOUTUBE: WATCH HERE
Links:
X (Twitter): @catehall
LinkedIn
Cate's Article — How to be More Agentic
⌛TIMESTAMPS
(00:00) - Intro
(01:29) - The scripts that Cate grew up with
(05:54) - Doors-opening credentials?
(09:45) - Leaving law for poker
(17:59) - Developing agency, learning form the others
(23:04) - Deterministic vs probabilistic economy
(26:15) - Risk and the diminishing prestige of the traditional paths
(30:32) - Burnout
(36:42) - Asking dumb questions
(41:21) - Defining ambition
(43:01) - Seeking actual feedback and how everything is learnable
(49:33) - The surface area of luck
(57:07) - Closing remarks
1 hr 1 min
May 13, 2024 1 Year Dad Reflections - Conversation with Sky King & Nat Eliason
This is from Sky King's podcast: https://skmp.supercast.com/
Guest info:
Nat: https://www.nateliason.com/

Nat also has an amazing book coming out which I highly recommend, "Crypto Confidential": https://amzn.to/44BJ74I
1 hr 24 min
April 16, 2024#173 Solopreneurship After Burnout — Justin Welsh on burnout, taking ownership of his time, struggling with a results oriented mindset, non-monetary success, becoming a top LinkedIn influencer, income goals, The Creator MBA, dealing with fears around mone
Justin is a former startup executive who helped build two startups past valuations of $1B, teams of 150+ people, and raise over $300M in venture capital. Now he’s building his one-person knowledge business toward $5M in annual profit.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Personal website
LinkedIn
X (Twitter): @thejustinwelsh
The Creator MBA
The Saturday Solopreneur
⌛TIMESTAMPS
(00:00) - Intro
(00:56) - The scripts that Justin grew up with
(09:21) - Attention and social media
(11:05) - Liking your job, the interest curve & having goals
(15:17) - Justin's burnout, finding a new path & taking ownership of your time
(24:52) - Not starting earlier & struggling with a results oriented mindset
(31:08) - Creativity, non-monetary success & business as a creative act
(37:31) - Being the nr. 1 LinkedIn influencer
(41:52) - Income goals on the solo path
(46:31) - The Creator MBA & Brennan Dunn
(51:31) - Not making the solo career a job & fears around money
(57:09) - Avoiding emotions, confidence
(01:01:39) - What's Justin excited about
(01:03:20) - Closing remarks
1 hr 6 min
April 01, 2024#172 Success In The Second Half Of Life — Henry Oliver on John Stuart Mill, Samuel Johnson, Penelope Fitzgerald, why we shouldn't dismiss Gladwell, writing, late bloomers, the importance of finding the others, Tyler Cowen's help and the lessons from Audre
Henry is a writer, speaker and brand consultant. He joins the podcast to discuss his upcoming book — Second Act — in which he analysises the phenomenon of late bloomers and what we can learn from them.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Personal website
Substack: The Common Reader
X (Twitter): @HenryEOliver
Second Act
⌛TIMESTAMPS
(00:00) - Intro
(00:11) - Guest introduction
(00:57) - The scripts that Henry grew up with
(05:10) - John Stuart Mill
(07:41) - Samuel Johnson
(14:23) - "The common reader" & Why we shouldn't dismiss Gladwell
(17:41) - Writing
(21:25) - His book about the late bloomers
(28:10) - Penelope Fitzgerald
(33:38) - Is it too easy to share your writing?
(36:39) - The importance of finding the others
(40:42) - Conversations, talking to yourself and writing
(43:14) - Getting disappointed early
(47:52) - There is no actual average person, the importance of taking variability into account
(52:29) - How writing a book changes people
(55:10) - Tyler Cowen and the power of the internet
(57:47) - What Samuel Johnson would be working on today?
(59:36) - The lessons from Audrey Sutherland
(01:04:53) - Closing remarks
1 hr 8 min
March 25, 2024#171 "All Work Is Noble," Montessori, and Kids & Work — Matt Bateman on starting growing up with the internet, digital and industrial literacy, studying philosophy and learning how to teach, starting the Guidepost school network, how to train teachers, h
Matt Bateman has a PhD in philosophy. He has abandoned the academic career, to pursue education in the Montessori system. A dad of three, he is passionate about educating children. Having worked a lot with training the teachers in the Montessori approach, he has now taken a step back to focus on writing his book.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Matt's Twitter — @mbateman
montessorium.com
guidepost
⌛TIMESTAMPS
(00:00) - Intro
(00:54) - The scripts that Matt grew up with
(04:40) - Growing up with the internet
(07:42) - Kids and technology, digital and industrial literacy
(13:33) - Babysitting, PhD in Philosophy and learning how to teach
(17:07) - Getting into Montessori
(19:02) - Starting the Guideposts & How to train good teachers
(23:50) - The pathological approach to work we learnt and how little children naturally want to help
(32:28) - “All work is noble”
(40:29) - The role of values in education through history
(48:11) - The Montessori system, differences in non-alphabetic writing systems
(53:19) - Agency as the aim of education
(58:30) - Advice for parents, the pros and cons of college
(01:05:10) - Matt’s new book & the hidden bad value system taught in modern schools
(01:09:24) - Closing remarks
1 hr 14 min
March 18, 2024#170 Apprenticeships, Sabbaticals & "Good Work" — Steve Schlafman & Matt Yao on slowing down, deprogramming, unlearning, learning from others, deciding to quit, going on a sabbatical, not being jealous anymore, competitiveness and enoughness, finding good
Steve is a professional coach and the founder of Downshift — the world's first decelerator. He has left a career in venture, but he remains ambitious, it's just that his ambition is now to have a good, multidimentional life, where he can be a good dad for his kids.
Matt has left a traditional path early on to write, travel and discover his own path. When he met Steve, he offered him to become his apprentice and joined Downshift.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Downshift
Steve's website
Steve's Twitter
Matt's Twitter
Matt's blog — Game of One
Matt's blog — Build in Climate
Downshift on Twitter
⌛TIMESTAMPS
(00:00) - Intro
(02:14) - The scripts that Steve & Matt grew up with
(05:00) - Slowing down, deprogramming and unlearning
(11:52) - The cocoon stage
(14:05) - Deciding to quit
(18:25) - Learning from others on the path and having children
(25:18) - Trust
(28:29) - Matt's sabbatical, finding good work
(34:26) - No jealousy, competitiveness vs enoughness
(38:36) - Matt's apprenticeship with Steve
(47:45) - Putting yourself in a place where it's easy to help you
(51:43) - Downshift & Ambition
(01:02:14) - Marriage & Family
(01:10:02) - Reframing money, skiing and oatmeal
(01:16:23) - Launching decelerator
(01:20:34) - Closing remarks
1 hr 23 min
March 12, 2024#169 "2M Subscribers, I love what I do, should I take a break?" — David Pakman on finding good work early, , how money and motivation changed over time, finding a balance in content creation, life after YouTube, his doubts about taking a sabbatical, havin
David Pakman is a political commentator and the host of The David Pakman Show. He joins the podcast to explore a possible paradigm shift in the way he approaches his work and life after the birth of his daughter.
🎥🍿 YOUTUBE: WATCH HERE
Links:
The David Pakman Show
X (Twitter): @dpakman
YouTube: David Pakman Show
Instagram: david.pakman
⌛TIMESTAMPS
(00:00) - Intro
(01:12) - The scripts that David grew up with
(03:26) - David's first steps on the internet
(06:13) - Finding an alternative path
(11:11) - Advice for young YouTubers
(13:17) - Money, motivation, workflows and how they changed over time
(18:15) - Imagining life after YouTube, doubts about taking a sabbatical
(27:57) - Having a child
(30:31) - Taking time off and fans
(34:16) - Divisive politics, public recognition and hateful comments
(41:28) - Growth ceiling, YouTube colleagues and the lack of clear role models
(46:40) - The dynamics of creator economy, YouTube & other creative projects
(52:57) - David's inspirations, what does he read
(56:55) - Closing remarks
59 min
February 27, 2024#168 Building With "margin for life" — Justin Jackson on lessons from running a skate shop, optimizing for profit, running a "calm company," co-founding Transistor, having kids early, designing margins and how money actually does make him happy
Justin is the co-founder of Transistor, a podcast hosting platform on which The Pathless Path podcast is hosted. Justin is passionate about designing his company so that all the team benefits. He achieves that by making sure that there is always a financial margin as well as a "margin for our emotional health, margin for our physical health, margin for life."
🎥🍿 YOUTUBE: WATCH HERE
Links:
Personal website
X (Twitter): @mijustin
Justin's podcast
Transistor
⌛TIMESTAMPS
(00:11) - Guest introduction
(02:30) - The scripts that Justin grew up with
(07:21) - Lessons from running a skate shop
(13:15) - Optimizing for profit in business
(25:49) - The opportunities on the internet, staying in the water, the survivor bias
(35:08) - Getting into digital business
(42:10) - The importance of the customer support
(44:29) - "A calm company" — designing the company to make their lives better
(53:36) - How Transistor has changed Justin's life?
(54:00) - Having kids early and how more money actually made him happy
(56:21) - How Justin approaches money
(58:53) - Navigating the changes in the podcasting platforms
(01:07:30) - The next chapter for Justin
(01:09:22) - Where can we find out more about Justin?
(01:10:23) - Closing remarks
1 hr 12 min
February 20, 2024#167 Wandering in the Wilderness — Dom Francks on confronting fragility, his love of nature, the disconnect from nature, working as a software engineer, viewing yourself as a piece of poetry, how we're always embedded in nature and being guided by intuiti
Dom is the lead guide at the VIVIFY Regerative Leadership Program. He helps leaders develop by taking them on an 8-day backpacking expedition in the Sierra mountains. Dom is passionate about preserving the natural world, staying connected to it and practicing aliveness.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Personal website
VIVIFY (Get $500 off if you mention this podcast)
Substack
⌛TIMESTAMPS
(00:00) - Intro
(01:18) - The scripts Dom grew up with
(06:40) - Dom's grandfather, a WW2 vet
(09:05) - Experiencing hardship, confronting the fragility
(16:19) - Dom's love of nature
(18:01) - Stanford & Golf
(21:41) - Balancing wilderness education and software engineering
(30:57) - How to avoid being perpetually dissatisfied
(32:46) - Viewing yourself as a piece of poetry
(36:44) - How liking your work makes you better at it
(38:35) - We're always embedded in nature
(41:47) - How to connect with nature
(50:09) - Leisure and wandering
(54:32) - Being guided by intuition
(01:02:21) - Closing remarks
1 hr 8 min
February 13, 2024#166 Breaking Free of the Rules — Rick Lewis on being a child actor, dropping out of college, being a professional juggler, street performing and a clowning, the corporate world as an outsider, breaking rules, parenting and how to reinvent yourself
Rick Lewis could be succinctly described as "a speaker, author & professional consultant", but such technical labelling wouldn't paint a fair picture of who he really is. He describes what he's doing as "intelligent misbehavior". He's public appearances have a much deeper goal than just pure entertainment. Rick is passionate about discovering and breaking the hidden rules that rule our behavior and stifle our growth as people.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Personal website
Pivot to the Podium
Rick's Book
⌛TIMESTAMPS
(00:00) - Intro
(00:11) - Guest introduction
(00:59) - The scripts that Tick grew up with
(08:07) - College & Entrepreneurship
(14:08) - Guided by joy
(20:01) - Getting support from others
(24:32) - Public speaking, writing the book, how to avoid plateauing
(39:43) - Observing the corporate world as an outsider
(42:31) - The biggest takeaways, finding the throughline
(59:05) - Parenting & aging
(01:06:58) - How to approach public speaking?
(01:12:24) - Rapid fire questions with Rick
(01:15:24) - Where can we learn more about Rick?
1 hr 18 min

About The Pathless Path with Paul Millerd

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The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their…