The Pathless Path with Paul Millerd

By Paul MillerdBusiness Entrepreneurship Careers

The Pathless Path with Paul Millerd episodes

May 01, 2023#143 The Art of Living - Kyle Kowalski on how to have an existential crisis, synthesizing the art of living, curiosity as fuel, his relationship with money, "killing himself to work" and "purpose washing" in big companies
Kyle was a marketing executive who believed in the "hard work" ethic. After an existential crisis, he decided to carve his own path as a solopreneur and started Sloww - "a trusted resource of lifelong learning". Kyle describes his purpose as "synthesizing the art of living for students of life".
🎥🍿 YOUTUBE: WATCH HERE
Links:
Twitter: @KyKow
Sloww: sloww.co
Happiness Book
Igikai 2.0
⌛TIMESTAMPS
(01:22) - The scripts that Kyle grew up with
(13:21) - How to have an existential crisis
(29:51) - Decompressing from his career
(42:39) - Sloww, thinking and the art of living
(52:59) - Kyle's next phase, sharing the personal story
(01:02:41) - Long form content, Kyle's course on synthesis
(01:08:55) - Where can we find Kyle?
(01:09:26) - Thanks and Goodbyes
1 hr 12 min
April 17, 2023#142 Goofing Off On Purpose - Kevin Kelly on why we should subsidize travel for young people, owning his time, a rest ethic, riding his bike across US, his love of YouTube, staying optimistic about the future, raising children and his new book
Kevin is the founding executive editor of Wired magazine, a writer and a photographer. When he was young he dropped out of college and travelled to Taiwan, which he describes as a live changing experience. Kevin is passionate about owning his time, the importance of goofing off and staying optimistic about the development of technology.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Kevin's website: kk.org
Kevin's articles on Wired
Excellent Advice on Living: Amazon
⌛TIMESTAMPS
(01:01) - Taiwan and the importance of travel
(08:53) - Owning time instead of money
(14:12) - Work, rest ethic, taking time to goof off
(24:57) - Riding his bike across US
(28:45) - YouTube
(33:12) - Patience, optimism and technological changes
(39:59) - Raising Children
(45:10) - Kevin's book and the power of outsourcing
51 min
April 10, 2023#141 Ryan Holiday's Secret Weapon - Billy Oppenheimer on growing in Philadelphia, almost going to law school, role models, working with Ryan Holiday, his research process, the notecard system, skiing, and the downsides to fame
Billy used to be an avid skier, working odd jobs and traveling between the northern and southern hemispheres trying to catch the best skiing. In 2018 he e-mailed Ryan Holiday and pitched him on doing some work for him for free. In a couple of months, he was hired as Ryan's research assistant. Billy is one of the most curious people I know and we dive into his journey.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Twitter: @bpoppenheimer
Website: billyoppenheimer.com
Billy's Newsletter
⌛TIMESTAMPS
(00:56) - The scripts Billy grew up with
(13:07) - Reaching out to Ryan Holiday
(17:14) - The research process and learning from Ryan
(24:43) - Skiing, Australia and finding his own voice
(39:45) - Animal courtship
(43:04) - How Ryan Holiday manages his team
(51:04) - Ambition and learning from past models
(01:02:32) - Downsides to fame
(01:03:23) - Where can we find Biilly?
1 hr 6 min
April 03, 2023 #140 Tom Peters - Fired from McKinsey to Top Business Thought Leader
I'm sharing this conversation I had a couple of months ago with Tom Peters. Our convo got cut a bit short but it was a fun conversation reflecting on his trajectory, why he got kicked out of McKinsey
To learn more about Tom: His Website
33 min
March 27, 2023#139 Compounding Memes - Trung Phan on his great grandfather, living abroad, the expat community in Asia, writing, working at The Hustle, children and work, balancing his various activities, going solo, and playing the long game
Trung is a writer at Workweek, cofounder of bearly.ai, and co-host of the Not Investment Advice podcast. He is passionate about playing the long game and unleashing the power of compounding.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Twitter: @TrungTPhan
Website: trungtphan.com
Bearly.AI
Podcast: Not Investment Advice
Trung's writing at Bloomberg and Workweek
Trung's Newsletter

⌛TIMESTAMPS
(02:12) - College and getting up late
(04:06) - Trung's great grandfather - Vietnamese hero
(08:53) - Vietnam, important lessons from living abroad
(21:27) - Writing & productivity
(42:11) - Kids, work & flexibility
(46:05) - Playing the long game
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community

📲Connect + Follow Paul
Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe
🙏Further Ways To Support The Podcast:
I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial
51 min
March 20, 2023#138 Money & The Creator Economy - Steph Smith on our lack of wisdom about money, reaching "ice cream freedom", The Hustle, balancing employment and side gigs, unconventional paths, opportunities in the creator economy and how not to get disappointed at y
Steph Smith is the host of the a16z podcast and is an online creator, former consultant, former digital nomad and all-around badass. We talk about money, work, relationships, and weddings...
🎥🍿 YOUTUBE: WATCH HERE
Links:
Twitter: @stephsmithio
Steph's book: doingcontentright.com
a16z Podcast
The Sh*t You Don't Learn in School Podcast
Blog: stephsmith.io

⌛TIMESTAMPS
(01:19) - The scripts that Steph grew up with
(03:09) - Perceptions of money over time
(28:37) - Working at The Hustle
(33:19) - A16Z and Beginner's Mindset
(37:26) - Solving the life puzzle with a partner
(46:18) - Scripts around kids
(51:42) - Avoiding long wedding planning cycles
(55:32) - Full-time employment and podcasting
(57:23) - Opportunities in the creator economy
(01:01:45) - Is Paul underpricing his book?
(01:05:19) - The most interesting opportunities in the creator economy
1 hr 11 min
March 13, 2023#137 Life as Conversation - Russ Roberts on his relationship with his father, starting the EconTalk podcast in 2006, Adam Smith, why people want to be "lovely", aiming high, why it's hard to have fun, misunderstandings of the academic world, and moving to
Russ is an economist, a research fellow at Stanford University's Hoover Institution and president of Shalem College in Jerusalem. One of pioneers of podcasting, he's been hosting EconTalk since 2006.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Twitter: @EconTalker
EconTalk Website: www.econtalk.org
EconTalk YouTube Channel

⌛TIMESTAMPS
(03:25) - The influence of Russ' father
(10:35) - What modern economics often fails to observe
(15:37) - Adam Smith and human nature
(26:27) - Starting EconTalk in 2006
(40:04) - Moving to Israel in his 60's
(44:57) - How people misunderstand the Academia
(49:05) - How Russ' approach to his podcast developed over time
(52:23) - The metaphor of a conversation
(56:33) - Mortality & fatherhood
(01:03:11) - Russ' dream guest and what's next
📕Buy Paul’s Book
: The Pathless Path
🤝Join Find The Others: A Community For People On Unconventional Paths
📲Connect + Follow Paul
Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe
🙏Further Ways To Support The Podcast:
I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial
1 hr 9 min
March 06, 2023#136 Complexity & Complicatedness - Sam Spurlin on playing hockey, why he quit teaching, studying at Claremont, leaving a PhD program, working pro bono too start his career, complicated vs complex systems, how to deal with ego in organizations, remote wor
Sam is a partner at The Ready - an organizational design consultancy operating fully remotely. He is also a prolific writer, passionate about personal development, self-managing organizations and adopting a more human, adaptive, and meaningful way of working.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Twitter: @samspurlin
Instagram: samspurlin
LinkedIn: linkedin.com/in/samspurlin
Sam's writing: samspurlin.com/writing
Sam's writing on Medium: samspurlin.medium.com
Newsletter: thedeliberate.substack.com/p/landing-page

⌛TIMESTAMPS
(00:53) - The scripts that Sam grew up with
(09:31) - Teaching and why Sam quit
(16:32) - Claremont and letting go of the PhD
(25:11) - Working pro bono to become a consultant
(30:48) - Complicated vs complex systems, ego in the organizations
(53:11) - Writing, podcasting, farming and retrospective meetings
(01:01:24) - The trap of a "dream job"
(01:04:49) - Closing remarks
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community

📲Connect + Follow Paul
Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe
🙏Further Ways To Support The Podcast:
I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial
1 hr 10 min
February 27, 2023#135 Beyond Comfort - Derek Sivers on why great musicians shake things up, ambition, and moving to a new country as a superpower, lessons from Singapore, and the scripts around having children
Derek Sivers has been a musician, producer, circus performer, successful entrepreneur, TED speaker, and book publisher. He has lived all around the world and has never let himself be too comfortable - constantly changing and following his inner ambition.
🎥🍿 YOUTUBE: WATCH HERE
Links:
Twitter: @sivers
Website: sive.rs
My Favorite Derek Book: Anything You Want

⌛TIMESTAMPS
(00:54) - The scripts that Derek grew up with
(05:07) - Comfort as a plateau that needs to be shattered
(11:08) - Travel as a tool to change your life
(16:48) - Beliefs and actions
(22:10) - Learning from other people's approaches to life
(27:06) - Derek's future and how to learn from when our lives go off track
(33:15) - Scripts around having kids
(44:25) - Retirement & Ambition
(55:47) - Closing remarks
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path
😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community

📲Connect + Follow Paul
Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe
🙏Further Ways To Support The Podcast:
I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial
1 hr 8 min
February 20, 2023#134 The Office-Based Reality is Over - Dror Poleg on entrepreneurship in Israel, studying in Australia, working in China, Future of Remote Work and The Real Estate Business, How To Write A Top 5 Book in Almost Any Category, The Disappearance of The Middl
Dror worked as a real estate private equity exec, startup founder, front-end developer, parliamentary advisor, and soldier. Having lived all around the world he is now based in NYC, writing as an “Economic Historian”.
Having predicted that remote work is going to become the new norm back in 2015, he has just published a survival guide titled "After Office".
🎥🍿 YOUTUBE: WATCH HERE
Links:
Twitter: @drorpoleg
Website: drorpoleg.com
After Office
⌛TIMESTAMPS
(13:30) - Living in Australia and China
(22:32) - Writing and Work in Dror's life
(27:08) - Remote Work and Real Estate
(41:48) - Using information from the Internet - writing a top 5 book
(49:04) - Unconventional Paths and The Disappearance of The Middle-Skilled Jobs
(58:18) - Inequality, Luck, and Challenges for The US
1 hr 25 min

About The Pathless Path with Paul Millerd

From the publisher's feed

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…