Boundless: The Human Side Of Work

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)

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 crea

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

Gary Ware is someone that inspires me. I've seen him give two walks, both at the World Domination Summit in 2018 and then in 2022.  In each, he stood out for his ability to show up as himself and share playful and powerfully true stories about his journey.  I love when I get to meet people like Gary and this interview was no different.  You can feel his positive energy flowing through the screen (or earbuds!).

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 videosWe Don't Just Teach Content Marketing ... We Built Our Company With It (copyblogger.com)About The Kolbe A™ Index | Instinctive Strengths AssessmentVIA Character Strengths Survey & Character ReportsPamela Wilson: Mid-career Online Business Coach101 Essays That Will Change The Way You Think: Wiest, Brianna

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/

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.

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 an

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 Her

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:WebsiteTwitter @Malcolm_OceanSign Up For Complice and get one bonus weekCrowdHealth: 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

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 / TwitterLinks 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)

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 Ex

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 barHow a cold email to Ryan Holiday changed his lifeGrowing up in HawaiiSerendipitous events that lend to him moving to AustinThe future of AudioLinks MentionsModern StoaSky's Podcast (Paid) or RMRK.appThe Gray Lady WinkedThe Brass Check@consumersky (twitter)CrowdHealth: You ditched the traditional path… why haven’t you ditched

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:  The influence of money and prestige  Burnout and reflection The importance of the right partner  Finding the right medium  The Arc

I offer a short little update on the next steps for the podcast and include a live Q&A I did on youtube last week. Video link: https://youtu.be/CGbw7Q8hoys

Tim Malnick has always lived between the two worlds of business and creative/activist circles.  In his twenties, he stumbled into a creative group of young people, of which “none of them following the obvious path.”  This gave him a lot of confidence that different kinds of paths were possible and enabled him to offer a diversity of perspectives that he was able to bring to many different environments. One of the things he spends a lot of time on now is helping people transcend their relationship with money.  He runs The Money Workshop with people helping them explore the scripts people have with money and realized that people have one of two orientations towards the world: #1 The Money Path: “One day when I sorted this out I’ll get to do what I want” #2 The Life Path: “Do what you love and the more you follow it you will have your needs met with and without money” Which one are you? Learn More About Tim’s work here

Paul Canetti is a professor at Columbia Business School and sits on the Strategic Advisory Board of Riverside Acceleration Capital. We explore his initial passion for music growing up, how he became an accidental founder, and how he's exploring his relationship with work after exiting his startup.   He was named one of Inc.'s “30 Under 30” and has founded multiple software businesses including MAZ and ClickEasy (originally Bounce House), both of which were acquired in 2021. He is an angel investor, startup advisor, and the author of an upcoming book about the business implications of augmented reality. He also hosts Tech News for MBAs ---- New to Reimagine Work?  Learn more about Paul here JUST LAUNCHED:

I talked with writer and writing coach Sasha Chapin about the role of writing in our lives, how we think about writing, and how he specifically helped with my process in the book. Check out Sasha here: Sasha Chapin (imsashachapin.com) & Buy Paul's Book https://think-boundless.com/the-pathless-path/

Join Khe's Supercharge Your Productivity course: https://10k.radreads.co/join-syp11/yzrsv (affiliate)Get access to Khe's $10k training which will help you wander towards the pathless path: https://radreads.co/millerdFrom a live event where Paul & Khe talk about their shared journeys of self-employment, creating online & more

Just launched my book, The Pathless Path!  Purchase the book here. This is the introduction of the book. I'll be releasing some clips of me reading the book and will eventually publish an audio book.