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.
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...
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...
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...
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.
🎥�...
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".
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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.
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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.
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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
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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.
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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...
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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.
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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.
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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.
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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".
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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.
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(0:11) Introduction
(5:41) "The chronic state of perfo...
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".
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(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...
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...
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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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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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.
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In order to tell the story of a crime, you have to turn back time. Every season, Investigative journalist Delia D'Ambra digs deep into a mind-bending mystery with the hopes of reigniting interest in a decades old homicide case.
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