Dylan O’Sullivan is a curator, editor, and writer at O'Shaughnessy Ventures and Essayful. Dylan and I talk about writing, taste, discipline vs. inspiration, timelessness vs ephemerality, boredom and solitude vs. the internet, inciting a digital renaissance, not lying to yourself, and more. — (00:45) Curating & editing vs. writing (05:39) Fear of ne…

Steve Schlafman is a venture capitalist turned transition coach. We talk about lostness, transformation, curiosity, mindfulness practices, his new Downshift program, being a husband and father, and more. — (00:59) Lostness, navigating liminal identity space, personal transformations (18:31) Head and heart, mind and body; intellectualizing emotions …

Matt Clifford is a co-founder of Entrepreneur First and leads their AI efforts, as well as chair of ARIA, the UK’s Advanced Research and Invention Agency. We talk about EF, talent investing, ambition, why we don’t have more Thiel Fellowships, his new focus on AI, and AI safety concerns. — (00:59) Talent matters most(03:17) Scarcity of talent x cult…

Joscha Bach is a cognitive scientist and AI researcher. We talk about our relationship with & models of reality, creativity and curiosity, animism and self-organizing software, stages of development, and more. — (01:25) The dream world; how we interact with & perceive reality(03:49) Fear(05:16) Self, consciousness, & awareness(08:10) We're a coarse…

Gabe (@VividVoid_ on Twitter) is a writer and coach, and former Marine. We talk about inferiority, art, nothingness, spirituality, courage, fear, alignment with The Void, representations of reality, exposure therapy, Quality, and more. — (00:52) You’re not inferior to anyone else (06:14) Art is the byproduct of a spiritual practice (09:28) Authenti…

Nathan Baugh writes fiction and the World Builders newsletter. We talk about writing, non-fiction vs. fiction, storytelling and world building devices, Kurt Vonnegut and other authors, getting the most out of technology and the internet, and more. — (00:47) Why writing (02:46) Loops & closing the curiosity gap (04:05) The combination of short form …

Billy Oppenheimer writes the Six at 6 newsletter, and has been a writing and research assistant for Ryan Holiday, Robert Greene, and Rick Rubin. We talk about research, naive optimism, working for legendary writers and creatives, boredom, his newsletter, curation and creation, how “the work is the win”, and his first book. —(00:52) Naive optimism &…

John Coogan is the co-founder of Soylent and Lucy, an Entrepreneur-in-Residence at Founders Fund, and a YouTuber and podcaster. We talk about AI, pioneering vs. wire-heading, identifying problems to solve, the need for more risk takers, satisfying curiosity, techno optimism, YouTube and podcasting, and his next venture. — (00:53) “Benevolent murder…

Sasha Chapin is a writer, coach, and the co-founder of a fragrance line. We talk about his book, awakening, meditation, Deep Okayness, coaching, writing, fragrance, and more. — (00:54) Writing a book on meditation & awakening(04:30) What is awakening, and is there a “destination”?(07:48) There’s a “manager” in our head(11:56) Aliveness & egoism(13:…

Ryan Hashemi is the founder of Hashemi Studios, which helps businesses and creators grow on YouTube, as well as the former Chief Strategy Officer of Jubilee Media, a media company provoking understanding and human connection. Ryan and I talk about the longevity of YouTube, building the “Disney of Empathy”, keys to creating and growing on YouTube, m…

Chris Bakke is a serial entrepreneur, most recently selling his company, Laskie, to Elon Musk and X (Twitter). We talk about satire and memes, X/Twitter, authenticity, hiring and the labor marketplace, how Laskie got acquired, criteria for finding problems to solve, passion and pivoting, and creating value. — (01:04) Satire, shitposting & memes; au…

Arjun Khemani is a HS drop out and works at Airchat, an audio messaging network founded by Naval Ravikant and Brian Norgard. Arjun and I talk about education, knowledge creation, Airchat, the power of the internet, and more. Given that Arjun is located in India on a completely opposite time zone, we thought we’d use Airchat to make a unique, experi…

Jack Raines is the writer of the Young Money blog, Editor-in-Chief of Exec Sum, and a Columbia MBA student. We talk about alternative life paths, the importance of travel, how to think about finances, writing, satire, university, prioritizing fun, and his first book that’s in the works. Please enjoy. — (01:42) Alternative life paths and scripts(05:…

Michael Mayer is the co-founder and CEO of Bottomless and owner of a popular pseudonymous Twitter account. We talk about Twitter and media, habits and cultivating a sense of disgust, failure, technology and startups, distinguishing what’s important from the noise, and more. — (00:56) Caring too much about social media & audiences; taking a year off…

Danny McMahon (@Dodford on YouTube) is a filmmaker and documentarian, known for his portraits of pop culture icons. We talk about filmmaking and art, storytelling and inspiration, simplicity and experimentation, identifying your talent, and psychology. — (00:37) Why documentaries & the ease of remixing (03:11) Profiling inspiring individuals who ov…

Rory Sutherland is an author and the Vice Chairman of Ogilvy. We talk about perception vs. technological improvements, creativity, the battle between efficiency and invention, how we’re neither rational nor irrational, changes in advertising and social norms, evolutionary biology, and more. —(00:37) Perceptual arbitrage(08:23) Making space for rand…

Kevin Espiritu is the Founder and CEO of Epic Gardening. We talk about content creation, developing your passion, the pareto principle, paradoxes, creating cinematic universes, the global food supply chain, and more. — (00:42) Writing is a foundational skill across content(03:05) To get reps, you have to really want it(05:02) Developing a passion v…

Wolf Tivy is the Founder and Editor-in-Chief of Palladium Magazine. We talk about governance and building new institutions, religion and higher callings, virtuosity, agency, and more. — (00:16) How do you build a new governing bodies, polities, or political institutions? (18:46) Wolf’s religious underpinnings (31:03) Higher callings & Darwinian vir…

Chris Turner is the founder and CEO of Moonrise, a co-learning space for homeschoolers and creative kids. We talk about the public education system, homeschooling, taking kids seriously, the internet as curriculum, skills for navigating the future, finding meaningful work, education startups, technology and design in learning, and more. — (00:48) W…

Kyle Harrison is the General Partner at Contrary Capital, as well as a writer. We talk about hype cycles, talent vortexes, investing in people, battles between tradition and progress, building systems, writing, and much more. — (00:46) Acceleration of FOMO and hype cycles in investing(07:04) Being people-centric is contrarian in VC(11:19) Most barr…

Jackson Dahl is a venture capitalist and was on the founding team of esports company 100 Thieves. We talk about finding your compulsion, oscillating between interest areas, navigating accelerating technological change, the relationships between creators and audiences, building community online and in-person, and art and creativity. — (00:50) Identi…

Tyler Denk is the co-founder and CEO of newsletter platform Beehiiv, and was the second employee at Morning Brew. We talk about newsletters, creators, running a startup, standing out, taking the path less traveled, ambition, authenticity, and uniqueness. — (00:46) Why build a newsletter platform & not another Morning Brew-like newsletter(01:48) VC,…

Xavier Helgesen is the co-founder of Enduring Ventures, a long-term holding company. He also co-founded Better World Books and was the founding CEO of Zola Electric. We talk about holding companies, the publishing industry, capital allocation, focus, reinventing ourselves, building things that last, parenting, and more. — (02:43) Why run 20+ busine…

Emmett Shear is the co-founder and former CEO of Twitch, ex-interim CEO of OpenAI, and a visiting partner at Y Combinator. We talk about agency, meta learning, deliberate practice, coordination problems, parasocial relationships, positive sum games, and more. Please enjoy. — (00:51) When to persist vs. make a change(06:16) Know what you want and ho…

Nick (AKA Critter / @becomingcritter) is a writer and podcaster. We talk about presence, skepticism, religion, fearless authenticity, balancing seriousness and fun, relationships, and podcasting. Please enjoy. — (03:01) Seeking mystery & divinity(08:54) Skepticism, presence, and realizations about conceptions like time(23:36) Impermanent immediacy(…

Matt Bateman is the Vice President of Pedagogy at Higher Ground Education. We talk about a pedagogy, Montessori, capability and agency in children, experimentation in education, how young education is as a science, the importance of work, and a conception of the good life. — (00:42) Leaving academia(02:35) Why Montessori & seeing a classroom for th…

Nicole (@startingfromnix) is a writer. We talk about writing, introspection, being heart- vs. head-heavy, what’s core to your identity, pursuing meaning over ego, living in the present, depth and endurance, and more. — (00:41) Writes helps you clarify your thoughts(02:49) The taste gap & inching closer to what you want to write(05:47) Focusing on t…

Jake (@0FJAKE) is a podcaster, writer, and the former Chief of Staff for Balaji Srinivasan. We talk about sabbaticals and taking the time to find your work, pseudonymity and authenticity, status, challenging norms, the benefits of audio, and more. — (00:44) Taking sabbaticals(06:29) People should spend more time finding their next thing(16:56) Havi…

Dwarkesh Patel is the creator of the Lunar Society newsletter and podcast. We talk about curiosity, talent, podcasting and research, status games, finding what to work on, standing out from the crowd, and AI & futurism. — (00:42) Starting a podcast out of college while others enter the workforce(04:51) How he overcomes the occasional desire to quit…

Tom Morgan is a writer and director at Sapient Capital. Tom and I discuss curiosity, Joseph Campbell's Hero’s Journey and the call to adventure, Brett Anderson’s work and the movement of reality towards complexity, the question of what is value, and more. — (00:30) Why he left finance(03:38) Directing your skills & talents towards something useful(…

Eric Wollberg is the co-founder and CEO of Prophetic, a consumer neurotechnology company building Halo, a non-invasive device for inducing and stabilizing lucid dream states. Eric and I talk about why he’s working on this problem, consciousness, the dream state, best applications for this technology, epistemological metaphysics, and more. — (00:57)…

Ben Wilson is the creator and host of How to Take Over The World, a podcast which analyzes the lives of some of the greatest people to ever live. He’s also the founder of PodRamp and the producer of the My First Million Podcast with Shaan Puri and Sam Parr. Ben and I talk about greatness, the art of podcasting, lessons from the people he’s covered,…

Anne-Laure Le Cunff is an ex-Googler, writer and founder at Ness Labs, and PhD candidate in Psychology & Neuroscience at King’s College in London. We talk about treating life as a series of experiments, mindful productivity, redefining ambition, combining perspectives across domains, and more. — (00:55) Developing a love for science & writing(03:49…

Justin Welsh is a former startup exec turned solopreneur & creator helping people launch, grow, and monetize their internet businesses. We talk about long term thinking, playing your own game, content creation, status, the value of travel, and more. — (00:47) Why he chose content creation(02:47) Did content creation come naturally or take effort?(0…

Molly Mielke is a writer and the founding partner of Moth Fund, an early-stage venture capital firm aiming to increase the agency of exceptional individuals through investments and grants. We talk about rapidly "career sunk cost fallacy", increasing agency, investing in people and ideas, off the shelf games vs. creating your own, being famous among…

Adam Ryan is the co-founder and CEO of Workweek, a collective of industry-expert creators aiming to create business content their audiences actually enjoy. Adam and I talk about all things Workweek and the B2B knowledge/creator space. — (00:37) Individuals over institutions(03:35) Is there still opportunity in the B2C creator space?(05:31) Focusing…

Zach Pogrob is a creator. He’s a writer, the man behind the animated videos on the @behaviorhack Instagram and TikTok accounts — which have amassed over 1.5M followers — and the leader of the “obsession movement” on Twitter. Zach and I talk about finding and sustaining your obsession, his inspirations, cultivating a long term mindset, building a br…

Andrew Rose, along with his wife, Priya, are building The Neighborhood in New York City, with the goal of bringing together 1000 forward-looking, abundance-minded friends within walking distance of one another. Andrew and I talk about community building and bringing friends together, isolation, implementing the right social technologies, balancing …

Rich Bartlett helps people grow high-trust communities & decentralised organisations. He’s the co-founder of tech co-op Loomio, community building network Microsolidarity, management consultancy The Hum, and director of the social impact collective Enspiral. We talk about microsolidarity, fellowship and belonging, being optimistic and pessimistic a…

My guest today is Gurwinder Bhogal. Gurwinder writes The Prism, a blog covering the ways technology and psychology conspire to fool us, and how we can withstand the assault on our senses. We talk about writing, bugs in our psychological software, how we can better understand and manage our emotions and reactions, and the pursuit of finding truth. —…

Alpha Barry is the founder of Temple, which builds cities to make the world more prosperous and beautiful, as well as Monolith, which founds and funds companies building Africa’s industrial economy. We talk about his vision for Temple and Monolith, why we need new cities — and the opportunities and challenges of building them — and why Africa is th…

Visakan Veerasamy (AKA Visa) is a writer, both on Twitter and through his books Friendly Ambitious Nerds and Introspect — both of which I highly recommend. We talk about writing; networks, scenes, and subcultures; deviants and outliers; being introspective; and more. —(00:42) Visa's background(05:45) Online networks need a cultural paradigm shift t…

Ava (@noampomsky) is the writer of the Bookbear Express Substack, where she discusses human interaction and relationships through the lens of her own life. We talk about writing, reading, how a massive audience can change your writing, vulnerability, finding your thing to commit to, and how AI will impact dating and relationships. — (01:21) Ava's b…

Isabel is a writer, both on Twitter (@isabelunraveled) and through her Mind Mine blog/newsletter. We talk about building your intuition muscle, being rational vs. gut-led, vulnerability, the importance of humility, and more. — (00:37) Isabel’s background(04:26) Gradual vs. discrete change(05:53) Nurturing intuition & balancing the practical vs. int…

Michael Ashcroft is a climate and energy consultant turned Alexander technique teacher. Michael talks and teaches about awareness through his blog and course, “Expanding Awareness”. We talk about what Alexander Technique is and isn't, how to cultivate awareness, effortless effort, the importance of direct experience, and much more. — (00:33) Michae…

Lenore Skenazy is the author of the Free Range Kids book and blog, and president of Let Grow — all of which focus on promoting childhood independence. We talk about how society and parents fears are disconnected from statistics, the importance of agency, the connection to current university culture, how let grow is helping, and more. — (00:33) Leno…

Kyle Kowalski is an ex-marketing executive and founder of Sloww where Kyle synthesizes lifelong learning that catalyzes human development. We talk about meaning crises, psychological development, ikigai, the birth lottery, agency, and more. — (00:26) Kyle’s background (07:31) Why it took him 2.5 years to finally quit his job (12:06) Why Sloww align…

Colin Keeley is the co-founder of Verne, a holding company for SaaS businesses, and the creator of IndiePE, a course for people to learn how to buy their first small business. This episode is a great primer on hold co’s and buying online SMBs for those interested in the space. — (00:27) Colin's background (01:00) What attracted him to hold co’s & b…

Zohar Atkins is a rabbi and thinker. He’s the author of the blogs “Etz Hasadeh” and “What Is Called Thinking?”, and host of the "Meditations with Zohar" podcast. Zohar and I talk about academia, Judaism, content creation, and bridging philosophy and religion. — (00:27) Background (05:24) Thoughts on academia and the peer review process (08:56) What…

Travis Jamison is a serial entrepreneur and investor. Among other things, Travis owns an SEO agency (Smash Digital), a holding company for cash flowing businesses (Smash.VC), and an online investing community and newsletter (Investing.io). Travis and I talk about how he got his start, all things investing (SMBs, hold co's, crypto, and the macro env…