All Episodes
Displaying episodes 1 - 30 of 181 in total
#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 money
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 buil...
#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 Audrey Sutherland
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 bloomer...
#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, how children learn and work, values in education, agency, and writing his new book
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 educat...
#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 work, ambition, the apprenticeship, Downshift, decelerator, marriage, family and reframing money
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 h...
#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, having a daughter, dealing with public recognition and hateful comments, the lack of role models
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 w...
#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 th...
#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 intuition
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. ...
#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 ...
#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 his YouTube channel, introducing new people to his audience, the probabilistic mindset and what he learnt from poker that helps him in his life
Kevin 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 w...
[Repost] My Nervous System Guru & Friend - Jonny Miller on His Own Pathless Path, Grief, Friendship, David Whyte & More
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 privile...
#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
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...
[Replay] Reinventing After Quitting A Top Job At Amazon - Christine Bader
Christine Bader is currently living in Bali, Indonesia, where she is spending time focused on her family and self. She is the author of The Evolution of a Corporate I...
[Replay] Taking a "structured sabbatical" & Calm Companies - Jacqueline Jensen
Jacqueline Jensen has been a digital nomad for 3.5 years, living and working globally. It might surprise you to find out then, that she's written a book called "Travel...
[Replay] Starting a "tribe" and living on an island with three kids - Ben Keene
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 carvin...
[Replay] How "total work" took over the world - Andrew Taggart
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 wi...
[Replay] We Adopted a 4-Day Workweek - Tash Walker
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 r...
[Replay] Living On A Boat for 1.5 Years - John Zeratsky
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 th...
[Replay] Packy McCormick on Injecting Fun To Newsletters
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 pa...
#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
Jovian 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 wit...
#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 travel
After 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⌛...
#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
Tom 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 ide...
#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
Erin is a spiritual psychology and meditation teacher, with a background in clinical psychology. She believes in experiencing rather than explaining and because of tha...
#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
Bilal 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...
#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, his love of reading and writing, self-publishing and becoming a Tik Tok creator
Ben 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 retiri...
#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
I'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.
#156 Saying "no" to something good — Jenny Blake on the inner CFO, spending every penny just to try, working at Google, running towards something vs. running away, creating assets for yourself, making yourself discoverable, and seeking advice from "friendtors"
Jenny is an author, international speaker, career and business strategist and executive coach. She has worked in a start up during her college years and then she worke...
#155 Homeschooling = Future of Education? - Hannah Frankman (Repost)
Hannah is awesome and you should listen to this podcast. She grew up homeschooled, is an endlessly curious person, has a deep sense of agency, and is a pro at carving...
#154 Learning to "Lean Out" - Dr. Dawn Baker's Journey from Medicine to 'Leaning Out', Embracing Unconventional Paths, Living Off-Grid, and Homeschooling
Dawn has a medical degree but she didn't pursue a traditional career as a doctor. She lives off grid with her husband and her homeschooled daughter. Dawn is passionate...
#153 Beyond Mimetic Desires - Luke Burgis on the temptations of conformity, contemplating life in Starbucks, thick desires and thin desires, letting go of control, the importance of play, learning from different work cultures, his stay in Rome and becoming a father
Luke has a background on Wall Street and has founded 3 companies in Silicon Valley. He describes his adult life as a constant state of uncertainty. At some point, he t...
#152 The Creator Therapist - Melvin Varghese on Emigrating to Texas, his work as a clinical psychologist, starting a podcast, the birth of his daughter, re-evaluating life and money and detaching identity from work
Melvin has a PhD in psychology but to call him just "a psychologist" would be trying to fit him in too small of a box. He has left a successful clinical career to buil...
