The Pathless Path with Paul Millerd

The Pathless Path with Paul Millerd

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 perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Khe Hy, Ben Hunt, Wade Foster, Dan Vassallo, Kris Abdelmessih, Steph Smith, Amir Salihefendić, Alex Pang, Visakan Veerasamy, and more.

Episodes

#147 You Can Love Cooking Too - Myles Snider on intuitive cooking, living in Argentina, working in Tulum, food industry scripts, health myths, the beauty of "slow cooking"

May 29, 2023 • 79 mins

Myles is a chef and a farmer's market enthusiast. He studied economics and was pursuing many other interests like filmmaking on the side. During his stay in Argentina, he realized that he wanted to follow his true passion - cooking. Although he hasn't gone to a fancy cooking school, he managed to get a position working under a former Michelin star chef in Tulum and now he's sharing his love for cooking on the Internet, mak...

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#146 Separating Work & Identity - Simone Stolzoff on the myth of a "Dream Job," last-minute around the world trip, journalism, work, identity, writing his book, knowing when to quit, and the dangers of turning passion into a livelihood

May 22, 2023 • 66 mins

Simone Stolzoff has worn many hats. He's worked as a writer, designer, and now, Author. He grew up with "four parents", each having a unique influence on him,  He grew up being told he could do whatever he wanted but realized there were assumptions behind that. Over the last couple of years, he's contemplated how we can design a life not centered around work (which obviously interests me as well) and has come to some inter...

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#145 Capitalist by Day, Spiritual by Night - Alex Hardy on achievement, Wall Street, tech startups, exiting his company, pride & suffering, his sabbatical, suppressing his curiosity and rediscovering his passions

May 15, 2023 • 92 mins

Alex was crushing it early in his career, ending up on Wall Street after getting a combined JD/MBA.  But after a few years, he went looking for his next mountain, aiming his ambition at the tech sector. He ended up co-founding LiveOak, a company he eventually sold in 2020. After that, he struggled to determine what was next and finally decided to walk away from more than a million dollars. Now he's embracing non-doing, rec...

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#144 The Creator Pivot - Khe Hy on laying people off, collapsing course demand, seasons of creativity, having zero change in net worth in eight years, competitiveness, investing, coaching, and marriage on the pathless path

May 8, 2023 • 71 mins

In 2015 Khe left a Wall Street carrier to pursue his own path of "uncomfortable introspection", reevaluating his life. This is a constant process - Khe is always being emergent to himself. Now he finds himself at a crossroads - after a great initial success in 2020, he recently had to scale down his cohort-based course. Although laying people off was tough, Khe welcomes the change as entering a new season of creativity.

🎥�...

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#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

May 1, 2023 • 72 mins

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:

⌛TIMESTAMPS


📕Buy Paul...

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#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

April 17, 2023 • 50 mins

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
  • E...
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#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

April 10, 2023 • 65 mins

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:

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#140 Tom Peters - Fired from McKinsey to Top Business Thought Leader

April 3, 2023 • 32 mins

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


📕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

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#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

March 27, 2023 • 51 mins

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:


⌛TIMESTAMPS

  • (02:12) - College a...

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#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 your wedding

March 20, 2023 • 71 mins

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:


⌛TIMESTAMPS

  • (01:19) - The scripts that Ste...
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#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 Israel in his 60's

March 13, 2023 • 70 mins

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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:


⌛TIMESTAMPS

  • (03:25) - The influence of Russ' fat...
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#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 work failures, podcasting with his brother, and the importance of a retrospective meeting

March 6, 2023 • 71 mins

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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:

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#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

February 27, 2023 • 69 mins

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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:


⌛TIME...

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#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 Middle-Skilled Job, Inequality and The End of The Offices

February 20, 2023 • 85 mins

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:

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#133 Creation Without The Ego - Isabel Unraveled on writing, "the chronic state of performing", detaching your sense of self from the work, finding the inner child, paying attention to your emotions, trusting your intuition and why people should stop pretending

February 13, 2023 • 65 mins

Isabel is a writer who is very passionate about the creative process. She has some powerful original ideas about the relationship between the artist and their creation, trusting one's intuition, and why people should stop pretending.

🎥🍿 YOUTUBE: WATCH HERE

Links:


⌛TIMESTAMPS
(0:11) Introduction
(5:41) "The chronic state of perfo...

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#132 Making Money Simple & Smart - Nick Maggiulli on blogging into a new career, writing for smart people, building relationships in the finance world, the lifestyle creep myth, dying with too much money, and money emotions

February 6, 2023 • 69 mins

Nick Maggiulli is a finance data analyst and writer. He is the author of "Just Keep Buying" and has a blog titled "Of Dollars and Data".

🎥🍿 YOUTUBE: WATCH HERE

Links:


⌛TIMESTAMPS
(0:47) The scripts nick grew up with
(5:35) Writing books and blogging
(32:44) Building relationships in  the NYC finance scene
(36:07) W...

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#131 The Art of Sabbaticals - Cécile and Michelle on finding "forgotten hobbies", writing online, improving their relationship with money, abundance mindset and rediscovering joy

January 30, 2023 • 88 mins

Cécile has had a successful career in consulting, acquiring a senior position in a big company that has taken a leadership role in the energy transition in the UK. Although she was passionate about her job she decided to go on a yearlong sabbatical from work, traveling around the world and writing - creating space for her curiosity & creativity.

Michelle has a background in sales but after a couple of years in the busin...

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#130 You Have One Life - David Senra on finding his life's work, trial & error, the necessity of talking risks, mortality, balancing his entrepreneurial endeavours and family life and what can be learned from reading hundreds of biographies.

January 23, 2023 • 95 mins

David Senra has sponsored a $1,000 giveaway of copies of my book. You can grab a copy of The Pathless Path Here or https://tally.so/r/n0V0XZ (Check out Founders Podcast!)


David Senra is the creator of Founders Podcast and is obsessed with bringing alive the knowledge of the most driven, curious, courageous, and interesting founders throughout history.  He has spent almost all his time reading, re-reading, and recording ...

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#129 Friendly Ambitious Nerd World-Building - Visakan Veerasamy on Long-Orbit Friendships, Preemptive Defensiveness, "Hot Streaks," Writing A Book, Making $1000 for one copy & Negative Comments

January 17, 2023 • 98 mins

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Visakan Veerasamy is an internet creator and writer, he is passionate about the future of the internet, ideas, and how people can be bolder on their creative journeys. 

His mission is to build the greatest social graph of friendly, ambitious nerds that the world has ever seen.

This is our second conversation and dives much more into his current work and how he thinks about the int...

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#128 Crafting A Life You Love - Amy Tangerine on working in fashion, carving her own path, starting a business, a third-life crisis, scrapbooking as contemplation and learning from and inspiring her children

January 11, 2023 • 54 mins

🥳 Join Find The Others: Learn More Here


Amy Tangerine is a long-time creator, entrepreneur, and mother. We talk about her path, starting a business that took off, her "third-life" crisis, learning to inject rest into her path, her relationship with her mother, having children, scrapbooking and building a business around work she loves.

WATCH On YouTube


FOLLOW AMY

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