Claire Emerson is a writer and project consultant who helps business owners execute their best ideas.

She is the curator of Flourish newsletter and the creator of Implement My Course — a free 10-day email course on how to apply what you learn without procrastination poisoning your progress. 

Links Mentioned:

• Anna Macko - Crypto Queen (@lovingnotworking) • Instagram photos and videos
• We Don't Just Teach Content Marketing ... We Built Our Company With It (copyblogger.com)
• About The Kolbe A™ Index | Instinctive Strengths Assessment
• VIA Character Strengths Survey & Character Reports
• Pamela Wilson: Mid-career Online Business Coach
• 101 Essays That Will Change The Way You Think: Wiest, Brianna

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

• Twitter: @p_millerd
• Paul’s Newsletter: Subscribe to Boundless
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• I use Transistor to host this podcast. It rocks. Launch Your Here
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• 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

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
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🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here
• I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

I spoke with Tasshin Fogelman about his life's work to bring more love into the world, how he navigates life as a modern online monk, what he learned from spending time at the monastic academy, and what he see's as work worth doing.

You can learn more about his work here: https://tasshin.com/

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

• Twitter: @p_millerd
• Paul’s Newsletter: Subscribe to Boundless
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🙏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

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
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Tara McMullin is a writer, host of the What Works Podcast, and also cofounder of a podcast production studio.  She's been working with small business owners for more than 13 years and has a deep understanding of what makes them tick.  She’s recently written about realizing she was autistic and how that has impacted her role in the workplace.

🍿 Watch On Youtube

🔗 Links:

• Tara's Site: Explore What Works
• Twitter: @taragentile
• How learning I’m autistic changed the way I work 
• Finding A Way to Take Up Space 
• A Conceptual Analysis of Autistic Masking: Understanding the Narrative of Stigma and the Illusion of Choice 

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

• Twitter: @p_millerd
• Paul’s Newsletter: Subscribe to Boundless
• Video Episodes & Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• I use Transistor to host this podcast. It rocks. Launch Your 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

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here
• I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Aida Alston is no stranger to alternatives to the default path. From testing out of high school at 15, to finishing college with no debt, then going to medical school for free in Cuba, Aida has been walking her version of a pathless path for a long time.

But she's at a transition point now. She decided not to pursue clinical practice as a physician—again turning away from the default path right in front of her. She's been a full-time stay-at-home mother since then to her two children, raising them bilingually after becoming bilingual in Spanish herself during her time in Cuba.

She's a self-described early AND late bloomer, having sped through milestones early on but now slowly figuring out what's next for her work and family. She understands many of the challenges of going off the default path—like the paradox of choice—and how decision-making and prototyping are skills to be learned and practiced while building a pathless path.

She is from San Francisco originally but now lives in New York with her husband and kids.

👉 Follow Aida on Twitter and Read Her Writing

Links Mentioned:

• Life Is in The Transitions
• Late Bloomers
• Lost Connections
• The Hilarious World of Depression

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲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
• 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

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here
• I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

John Paller is a Denver-based entrepreneur and the Founder of Opolis, a Digital Employment Cooperative for independent workers. He is also the founder of ETH Denver, the world’s largest Web3 and Ethereum festival.

Prior to discovering Ethereum in 2015, John spent more than 15 years in talent acquisition, HR Technology, and employment systems, building multiple successful enterprises. John brings a breadth of experience in fundraising, investor relations, community outreach and crypto economies, guiding his vision of democratizing employment and growing decentralized communities. In 2014, John was awarded “40 Under 40” by the Denver Business Journal for his contribution to shaping the future of business.

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” during sign-up for a special discounted subscription offer. Sign Up Here

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

• Twitter: @p_millerd
• Paul’s Newsletter: Subscribe to Boundless
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• 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

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here
• I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Malcolm ocean is a fellow wanderer of the pathless path and as is such - is hard to describe. He runs a software company, Complice which helps people turn big goals into day-to-day actions. More broadly from my vantage point, Malcolm appears to be one of the most deeply curious humans alive about how we make things happen at the individual and group levels.

Follow Malcolm:

• Website
• Twitter @Malcolm_Ocean
• Sign Up For Complice and get one bonus week

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” during sign-up for a special discounted subscription offer. Sign Up Here

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

• Twitter: @p_millerd
• Paul’s Newsletter: Subscribe to Boundless
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• 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

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here
• I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

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 her own path.  She's done a ton of things including writing, coaching, and working at startups and has created jobs for herself, negotiated working remotely (before it was cool), and has done a ton of other things.  She recently founded Rebel Educator which is a media brand that aims to share more about homeschooling and alternative education with a broader audience online.

Follow Hannah:

• @HannahFrankman / Twitter
• @rebelEducator / Twitter

Links Mentioned:

• 3 Reasons Homeschoolers Often Become Entrepreneurs - Foundation for Economic Education (fee.org)
• No, You Don’t Need to be “Qualified” to Homeschool Your Children - Foundation for Economic Education (fee.org)

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

• Twitter: @p_millerd
• Paul’s Newsletter: Subscribe to Boundless
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• 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

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here
• I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Lauren and I first talked when I was locked down in Taiwan in 2021.  It was amazing to connect with another nomad and writer after weeks of not seeing people.  I was also a bit stuck in my book writing process and she gave me a ton of helpful hints to take my book to the next level.

I was excited to interview Lauren because she just finished her own book, Global Natives about her own experience as a nomad (since 2013!) and also the past, present, and future of the movement.  I think she is one of the most thoughtful perspectives on the future of work and global mobility.

Currently, Lauren is Executive Director of Plumia, the mission to build an internet country for digital nomads at SafetyWing, a Y Combinator company that raised a $35 million Series B in 2022. She is also author of the book Global Natives and writes the Counterflows newsletter) about borderless living. She tweets @LaurenRazavi.

SPONSOR: 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” during sign-up for a special discounted subscription offer. Sign Up Here

Links Mentioned

Timestamps

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path

📲Connect + Follow Paul

🙏Further Ways To Support The Podcast:

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here
• I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

This episode is with Sky King, the founder of Modern Stoa, a podcast advertising company for podcasters.  His path is fascinating - he grew up in Hawaii, rarely wore shoes, was heavily influenced by Asian culture, had a father who was retired, and somehow ended up in a massive corporation right after college.  In 2016. he became fascinated by how the media was shaping the 2016 US election and decided it was time to act.  From a cold email to Ryan Holiday to helping build Aubrey Marcus' podcast, Sky was on his way.  His long-term vision is to build an alternative to traditional advertising in audio.

We talk about this and a lot more including:

• Why he quit a good job to work at a smoothie bar
• How a cold email to Ryan Holiday changed his life
• Growing up in Hawaii
• Serendipitous events that lend to him moving to Austin
• The future of Audio

Links Mentions

• Modern Stoa
• Sky's Podcast (Paid) or RMRK.app
• The Gray Lady Winked
• The Brass Check
• @consumersky (twitter)

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” during sign-up for a special discounted subscription offer. Sign Up Here

Timestamps

• 1:41: Intro to Sky and where his name came from
• 5:03: Sky's influences growing up
• 11:34 Why he went to the corporate world
• 17:12 Cold emailing Ryan Holiday & vision for 
• 19:47 Sky's "quake moment"
• 25:15 Moving to Austin and working for Aubrey Marcus
• 30:44 Sky's desire to help people 
• 32:55 Growing up in Hawaii
• 36:10 Going to China at 10
• 39:30 Everything anywhere all at once reflections
• 44:40 The "true default path"
• 47:30 Hiring someone & responsibility
• 48:30 "what are you uniquely positioned to do?"
• 49:20 Advertising Subsidy & Media incentives
• 57:20 Meme farming & future of audio
• 1:01:30 Bucky Fuller & specialization

📕Buy Paul’s Book (Published Jan 2020): The Pathless Path 

📲Connect + Follow Paul

• Twitter: @p_millerd 
• Paul’s Newsletter: Subscribe to Boundless 
• Paul’s YouTube: Subscribe 

🙏Further Ways To Support The Podcast:

• 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

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here
• I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Being an undeclared major till his senior year of college, Lawrence didn’t really know what he wanted to do. After looking up which jobs make the most money, he decided to declare as an economics major, leading him to explore Investment Banking. While he didn’t end up working in investment banking, he was still pulled by the power of prestige, something he says “is a drug, and is most potent” when you are young and looking at schools. Over a number of years and experiments with music and creating and writing, he slowly started to figure out a better path forward for him. After leaving the corporate world for a second time, Lawrence finally found a calling - writing on his blog: More To That where he uses visual storytelling to express his ideas of pursuing alternative paths, sharing ideas, and creating online. 

Some of the topics we explore in this conversation include: 

How To Find Lawrence:

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” during sign-up for a special discounted subscription offer. Sign Up Here 

Audio Timestamps 

Buy Paul’s Book (Published Jan 2020): The Pathless Path 

Connect + Follow Paul 

Further Ways To Support The Podcast: I support the following services and recommend and/or use all of the following 

NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community

📲Connect + Follow Paul

• X: @p_millerd
• Instagram: @pathlesspaul
• Paul’s Newsletter: Subscribe to Pathless (26k+ People)
• Paul’s YouTube: Subscribe

🙏Further Ways To Support The Podcast:

• Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
• Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
• I use Transistor to host this podcast. It rocks. Launch Yours Here
• I record high-quality videos using Riverside: Sign Up Here
• I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial