The Pathless Path with Paul Millerd

This episode was a delight. Venkatesh Rao is the creator of Ribbonfarm and has been writing about the internet, technology, and gig life. This conversation focuses on his recently published book, The Art of Gig.  If you are thinking about working independently, becoming a freelancer, or are interested in consulting, you should definitely buy his book:The Art of Gig, FoundationsThe Art of Gig, SuperstructuresWATCH ON YOUTUBE: https://youtu.be/KC63HrF8V4EYou can find Venkatesh:on Twitter @vgron RibbonFarm (blog and substack)His consulting website: venkateshrao.comLinks Mentioned:How Karate Kid Ruined The Modern World (Cracked)Lords of StrategyWhat Theorising Is, Theorising Is NotTempo, by VenkateshJim KellerSquad WealthWe talked about:1:00 The scripts Venkatesh grew up with 5:05 Preparing for the leap, Dan Pink's books 10:48 Predictable income vs adventure18:58 Is $100 enough to build confidence in a project?21:08 Understanding the big consulting companies 27:18 The positioning vs people's school33:34 "Avoid polished deliverables" 42:17 Helping the executives take a step back 47:54 Systematic doubt and systematic confidence 51:40 What is "the clutch class" and why does it matter? 59:34 "What the clutch class is doing on evenings and weekends everyone will be doing in 10 years" 1:01:54 Keeping a 10-foot pole between your public identity and freelance gigs 1:03:38 How does Venkatesh work with clients? 1:07:53 The Yak collective and the future of indie consulting 1:12:34 Why the gig economy will outgrow the paycheck economy?📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

I believe that Kyla Scanlon is one of the most talented all-around creators. She is transcending the assumptions about what people want, especially with things like short-form videos. Her TikToks are synthesized, thoughtful, and funny, setting a new bar for what people want in an information age.We talked about her journey growing up in Kentucky, writing online, hacking into the finance industry from a non-target school, and ultimately deciding to become self-employed with less than two years of work experience.  Someone at her company told her she wouldn't "make it"🍿WATCH ON YOUTUBEKyla's Website: Educator, Creator, Investor Follow Kyla: @kylascan on Twitter, Instagram, and TikTokPath Role Model: Cody Ko⌛TIMESTAMPS1:09 The scripts that Kyla grew up with2:26 Writing her first book5:01 Finding out that people actually want deeper ideas7:31 Kyla's mindest when she was graduating9:24 Why Kyla didn't like her "cool" job in LA?11:50 DMing Paul and quitting her job16:05 Approach to work in Kyla's age cohort17:19 Kyla's parents on her leaving her job18:05 Pushback and skepticism19:27 Positive surprises after going on her own path20:27 "The passion crisis"23:24 How to find things you care about?25:26 Gatekeeping and aging out27:27 Kyla's short vertical videos33:09 AI and the future of writing35:58 Doing, not doing, and bike riding38:17 Remembering the good ideas38:48 The vibes of the economy41:20 Influence and responsibility42:58 Favourite financial leader?43:50 Why Kyla doesn't like what the Fed is doing?45:33 Generations living in different realities47:00 How did the "vibes" of Kyla's path change?50:51 Kyla's biggest supporters51:23 Putting herself out there52:04 Fame, success, and imposter syndrome54:03 Charts in Kyla's videos54:50 Kyla's TikTok's as poems55:48 What do people get wrong about short-form videos? 56:46 Going from TikTok to YouTube57:27 Bread58:32 "Money is not our moral compass".59:15 What does Kyla need help with?📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

The legible story is that Catherine is a writer, producer, and digital media consultant. She helps creative people connect with new audiences, usually writers, usually online. But she hasn't had a W-2 job since 2017. Before that she worked as an actor, worked at a company called Longreads, and then has done a bunch of solopreneur experiments over the past five years.Her recent interest is writing and speaking about how to navigate systems that make self-employment harder in the United States, like housing, healthcare, taxes, and insurance. 🍿WATCH ON YOUTUBELinks:Her How To Get A Mortgage CourseHer WebsiteThe Catastrophe of Success (Tennessee Williams)Small Bets Community📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trialAudio Timestamps:0:00 Audio intro2:10 What were the scripts Catherine grew up with?8:46 The differences in the experience of work between generations12:19 Applying to Emerson - the cold, unwelcoming Boston16:02 How Vassar teaches acting16:41 Auditioning in New York City after graduating17:16 Becoming disillusioned with a career path as an actress20:24 Producing her first play23:34 The American Booksellers Association30:24 Creating jobs for herself33:15 Working at Longreads38:00 Leaving Longreads39:30 After Longreads - moving to Austin44:17 Designing life with her husband48:18 How the system is incompatible with the new ways of life48:52 Leaving the US as a way to gain perspective49:42 "I'm breaking some law right now, I just don't know which one"50:37 Does work equal suffering? The IRS' definition of a hobby51:44 Why Catherine doesn't think in long time horizons52:59 Getting a mortgage as a self-employed person59:12 Small Bets & Dan Vassallo1:01:55 LLC vs. S Corp1:12:24 Healthcare in different states1:16:55 Catherine's course1:17:20 Tennessee Williams - The Catastrophe of Success1:23:24 Cathrine's path role models? 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

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 privilege to get to know him closely over the past four years on our own journeys. We've lived in Japan, Indonesia, and Mexico together. When we met we were both single but now are both married in cross-country relationships and have navigated finding work that matters, getting married, and living in foreign countries together.🍿Watch on YouTubeThis conversation was really special.Links:My interview with Jonny on The Curious Humans podcastPaul's Interview with Al Humphreys The Three Marriages (David Whyte)Jonny's TEDx Talk on Grief----📕Buy Paul’s Book (Published Jan 2022): The Pathless Path 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Andy Schoonover is the CEO of one of the sponsors of this podcast. After talking with him I actually thought he'd be a great guest on the podcast. He has a fascinating story from going from search-funder post-MBA grad to forming his own healthcare company. Can his company fix healthcare? Can anyone? Time will tell but I'm rooting for him.Join 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 (Sponsored Link, Includes discount)------------------📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: SubscribeFurther Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

🍿 Watch on YouTubeAli Green has been a remote worker since 2014. It took her a couple of attempts to fully unpair from the office and even when she had a fully remote job it took her another year to lean into her freedom. Now she's writing a book about what she's learned leading teams, living in different countries, and working remotely.Quitting her job and inventing a "story"Experiences working remotely since 2014Working full-time remotely for Duck Duck GoWhat people get wrong about remote workIndividual preferences & desire for freedomWhy she's writing a bookProductivity & remote workLearn more:Ali's Book "Remote Works" (Feb 2023)LinkedIn-------------📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Dr. Corey Wilks is a Licensed Clinical Psychologist and Executive Coach with over 15 years of psychological experience.In 2020, he stopped practicing therapy and ventured into entrepreneurship. Now, he coaches entrepreneurs and creates content to help people be more intentional with how they live, work, and create.His latest project is Intentional Life Design, a 5-week live cohort-based course focused on helping people overcome limiting beliefs, think bigger, and do work that matters.Find More About CoreyWriting on Psychology TodayHis personal website ------------------📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

In this episode, I talk with fellow creator and curious human Anne-Laure Le Cunff. She left her job at Google and embarked on an entrepreneurial journey about one month before I did in April 2017.  We compare the lessons we have learned over the past five years as well as talk about:How her mother's experience as an immigrant influenced her work scriptsHer creative interests vs. practical career choicesGetting into google and getting sucked into the tech worldQuitting her job and thinking she needed to found a companyShifting to freelancing and creating space in her lifeCreating and writing online and building an audienceCreating in a second languageHiring employees vs. hiring contractorsPursuing an academic path at the same time as a solopreneur pathHer personal site: Anne-Laure Le Cunff | Wellness, Creativity & CultureHer newsletter & community: The Maker Mind Newsletter by Anne-Laure Le Cunff (nesslabs.com)🍿 Watch on Youtube-------------📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Mike Steiner found himself on Penn’s campus at a young age not really knowing what he was supposed to do next. Thanks to helpful roommates, he started to figure out how to take advantage of the opportunities around him. He started getting more interested in math, statistics, and finance. He eventually ended up interviewing in New York and ending up at the famous training firm Susquehanna Investment Group (SIG). As a part-time trainer at first and then in a more central role, Mike started to experiment with different ways of teaching things like market making, probability, thinking in bets, and the behaviors needed to "make it" in the trading pits.This conversation was a delight and I think you'll enjoy it. We cover:Ending up at Penn and not really knowing what he was going to doFiguring out he enjoyed math and financeGetting a job at SIGJoining the training teamLeaving finance to spend more time with his kidsBecoming a high school teacherHow he thinks about teaching & mentorshipHis 20-year journey in creating his game "Stockslam"Prefer Video? 👉 Watch on YoutubeLearn more about stockslam:TwitterWebsite📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality videos using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Today I’m talking with Justin Moore - he and his wife was what he calls “OG Youtubers.” From creating content to landing sponsorships to building his own agency, he’s seen every angle of the creator economy. a lot over the last ten years. In the past couple of years, he walked away from the agency and has stumbled into a new path, one he’s finding a lot of joy following - helping other creators getting paid as a sponsorship coach.He turned down a buyout offer for his course and newsletter because he enjoys it so much. Check out this convo as we explore:Scripts Justin grew up withWhat he learned from his parents buying a SupercutsLaunching a successful Youtube businessHow illegible his success was to his familyHis struggles with hustle cultureFinding the work he likes doing…and moreJustin's mission is to enable creators big and small to land 1 million paid brand partnerships by 2032.You can find Justin here ⇒ Creator Wizard or Twitter📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost 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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial