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.🎥🍿 YOUTU

#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

19 days ago 1h 7m

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 HERELinks:Personal webs

#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

26 days ago 1h 14m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortMatt 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 ch

#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

Mar 18th, 2024 1h 23m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortSteve 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 amb

#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

Mar 12th, 2024 59m 23s

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortDavid 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 an

#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

Feb 27th, 2024 1h 12m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortJustin 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

#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

Feb 20th, 2024 1h 8m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortDom 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

#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

Feb 13th, 2024 1h 18m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortRick 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

#165 Gardening in the Digital Ecosystem — Kevin Espiritu on his fascination with the early Internet, how Poker broke his brain on money, starting his YouTube channel, Epic Gardening, taking a long term perspective, how to structure a video, transforming h

Feb 5th, 2024 1h 12m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortKevin is the man behind the Epic Gardening channel. Although he had not read the Pathless Path at the time of the recording of this episode, he seems to be living it with ev

[Repost] My Nervous System Guru & Friend - Jonny Miller on His Own Pathless Path, Grief, Friendship, David Whyte & More

Jan 30th, 2024 1h 57m

Enroll In The 5th Cohort of Nervous System Mastery: You can get $250 OFF using the code PATHLESS => nsmastery.comJonny Miller is a dear friend and I've had the privilege to get to know him closely over the past four years on our own journeys. W

#164 Transformation For High Achievers — Joe Hudson on growing up with an alcoholic father, living around the world, transformation and self-discovery, becoming comfortable with yourself, emotional fluidity, expressing emotions, and the art of parenting

Dec 11th, 2023 1h 12m

Joe is an executive coach and the founder of the Art of Accomplishment. Having worked as a venture capitalist, a consultant and an international banker, Joe discovered meditation on a trip to Asia and has practiced it since for over 25 years si

[Replay] Reinventing After Quitting A Top Job At Amazon - Christine Bader

Nov 27th, 2023 45m 6s

Join CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless”

[Replay] Taking a "structured sabbatical" & Calm Companies - Jacqueline Jensen

Nov 20th, 2023 44m 39s

[Replay] Starting a "tribe" and living on an island with three kids - Ben Keene

Nov 13th, 2023 1h

After attending a few corporate recruiting sessions, he didn't take for granted that his path was to enter the corporate world. Twenty years later, he is still carving his own path and has recently returned from Koh Lanta, where he lived with

[Replay] How "total work" took over the world - Andrew Taggart

Nov 6th, 2023 1h 9m

Andrew is a Practical Philosopher who believes that "there may be no greater vexation in our time than the question of how to make a living in a manner that accords with leading a good life." We dive deep into the questions of "what is the good

[Replay] We Adopted a 4-Day Workweek - Tash Walker

Oct 30th, 2023 45m 44s

Tash Walker is the founder of a firm and spends her Fridays making marmalade.Before instituting a four-day workweek at her firm, The Mix, she barely had time for her relationships. She decided to start doing research about different ways of wor

[Replay] Living On A Boat for 1.5 Years - John Zeratsky

Oct 23rd, 2023 1h 6m

John Zeratsky was a designer in the tech industry has worked with hundreds of startups in his time at Google Ventures. He’s also obsessed with redesigning time and thinking about what matters in life. Earlier this year he just got back from 1

[Replay] Packy McCormick on Injecting Fun To Newsletters

Oct 16th, 2023 44m

Packy says that his differentiation "is that I’m going to be having more fun than most people”I've been a big fan of the energy he's brought to his writing over the past couple of years. But he didn't set out to have a popular newsletter. His

#163 Luck Maximization — Jovian Gautama on being Indonesian in Taiwan, learning English from MTV and Reddit, graduating from a tourism high school, selling steel, podcasting, learning "tech" online, becoming the CEO of Castro

Oct 12th, 2023 1h 26m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortJovian is an Indonesian living in Taiwan, who is deeply immersed in the American pop culture through the power of the internet. His background in tourism helps him with prob

#162 Money, Work, Parenting & 1 Month In Taiwan - Angie & Paul on money scripts, cultural differences, being Taiwanese in the US, being American in Taiwan, perceptions of work in their families, life with a newborn, impostor syndrome, remote work and trav

Sep 18th, 2023 1h 17m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortAfter a month spent in Taiwan and 6 months into parenthood Angie & Paul share their thoughts and take some deep dives into various other topics.🎥🍿 YOUTUBE: WATCH HERE⌛TIME

#161 9 Year Identity Crisis?! - Tom Critchlow on being stuck, indecisiveness, going to wander, taking every 7th week off, strategically dropping the ball, hiring an editor, and fear of finishing his book

Aug 23rd, 2023 49m 26s

🥳 Join Find The Others: Learn More HereTom and Paul talk through Tom's challenges at this inflection point in his indie career, a book he's planning on shipping and how to think through indie consultant identity crises🎥🍿 YOUTUBE: WATCH HEREL

#160 - Why Manifesting Works — Erin Doppelt on how living in Israel and India changed her life, "snapshot manifestation", why women should work aligned with their menstrual cycle, entrepreneurship as freedom for women, pregnancy, and her new book

Aug 14th, 2023 1h 9m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortErin is a spiritual psychology and meditation teacher, with a background in clinical psychology. She believes in experiencing rather than explaining and because of that she

#159 Living Intentionally After "Enough" - Bilal Zaidi on leaving Google, emigrating to the US, video games, the intensity of New York, writing poetry and spoken word, travel vs vacations, and money and creativity

Aug 10th, 2023 1h 27m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortBilal was born in London to a family of Pakistani descent. A curious kid, with an interest in computers, he developed a successful website with over 500 000 readers in his t

#158 From Rugby to TikTok Influencer — Ben Mercer on navigating the transitional periods in his life, being a professional athlete with an English literature degree, the diversity of the rugby world, various motivations in sports, his passion for rugby, h

Jul 31st, 2023 1h 12m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortBen was a professional rugby player with an English literature degree — something not unheard of in the diverse rugby world, but also certainly not usual. After retiring fro

#157 Parenting & Our Future - Paul & Angie Check-In on Five Months of Parenting, Unexpected Happiness, Parenting Scripts, and The Time Bucket Exercise from Die With Zero

Jul 28th, 2023 1h 5m

Want To Become A Better Writer? Join Write of Passage's Upcoming CohortI'm trying to convince Angie to do more episodes, so if you like it please let us know by e-mailing both of us here.(00:16) - - Introduction and agenda for the podcast(03: