Audience of One

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 never writing quality work or living up to your idols

(08:32) Discipline vs. inspiration

(15:49) Balancing technology & ephemerality with the timeless

(17:44) Solitude, getting better at the craft, and having a "normal" life

(21:09) Boredom

(26:32) Short attention & the effect on art & mediums

(29:54) Lack of original works & risk taking

(36:43) Digital renaissance; timeless stories & works

(44:15) What is timeless & what will become timeless

(48:17) Creativity & the subconscious

(52:08) Long form writing vs memes

(55:00) Above all, don't lie to yourself

(01:00:29) Books he’d have in his bookstore window

(01:03:38) Three favorite directors & their three movies

(01:05:34) Final question for listeners

—

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 & feelings

(25:52) The role of curiosity; people, world, self

(29:52) Using practices as a means to an end

(34:21) Is downshifting antithetical to the history of humanity (advancement)?

(41:32) When to upshift

(46:27) Stillness & silence

(52:43) Renewal, rediscovery, experimentation

(57:39) Spouse support during transformations

(01:02:35) Balancing ambition & being a father

(01:06:54) Final question for listeners: what stops you from being at your best

—

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 culture (09:16) Founder qualities: effectiveness, unlocking resources (14:37) Can you teach ambition? (16:44) Failure to learn is an anti-signal (19:13) Alternative funding: income share agreements, adverse selection, longer term bets, & government funding (27:11) Why don't we have more grant programs or patrons, like the Thiel Fellowship? Scaling taste in talent & the macro talent allocation problem (41:32) Focusing on AI & handing off the EF CEO role (47:00) Is AI safety futile? Threat models and radical uncertainty (53:31) Final question for listeners

—

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 pattern on top of base reality (11:13) Presence & perceptual windows (12:16) Is this model mechanistic & reductionist? (13:50) Life exists to minimize free energy (16:47) What makes us different from other sentient beings & structures (20:35) Creativity: self-transformative exploration (23:40) Curiosity as uncertainty reduction (29:20) Exploration vs. exploitation (32:45) Combating social norms & conditioning; being a nerd (35:18) Knowing which models to update (37:56) Being a creator; being able to build & maintain (43:21) Everything can be understood (44:13) Animism; everything is self-organizing “software” (48:48) Natural vs. human-created “software” (50:57) AGI vs. natural intelligence (55:15) Limited by the locality of our sensory inputs (56:33) Stages of lucidity & development (01:03:35) Convergence of global traditions (01:09:40) Issue with Buddhism (01:14:16) Where does the animism and software arise from? (01:17:58) Building a coherent world, together

—

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) Authentic expression; anger & competition

(16:55) Do nothing, seek wisdom: space for contemplation & rest

(20:31) What is The Void?

(25:57) Microdosing honesty & better representations

(33:27) Courage & fear

(37:48) Exposure therapy & yin-yang

(41:35) Going from conditioning back to freedom; critical thinking & being a “combat medic”

(48:30) Direct experience; understand your behavioral loop & where you can intervene

(51:53) Taking practices & ideas from ideologies; being identity-less

(59:51) Poetic writing

(01:02:48) What is Quality?

(01:04:50) Gabe’s final question for listeners

—

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 non-fiction & long form fiction

(09:54) Storytelling & world building; Virgil Abloh’s 3% Rule

(14:30) Tradeoffs of traditional publishing vs. self-publishing; going direct-to-audience

(21:54) Tech and magic; AI

(28:26) His most influential authors

(31:08) Favorite opening sentences

(34:25) Vonnuget’s shape of stories & promise, progress, payoff

(49:11) Why not go all in on fiction?

(44:41) Writer’s self limiting beliefs

(52:54) Biggest fear as a writer: not living up to expectations

(55:33) Balancing technology and the internet with deep work

(59:58) What's one work of fiction that has stuck out?

—

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 & turning what you're already doing into a job (03:31) Researching is where he gets his dopamine (05:30) Combine timeless works with popular ones; triangulate stories (10:48) His note taking system (adapted from Ryan Holiday & Robert Greene) (15:19) The evolution of Six at 6; finding your niche & learning the wrong lessons from role models (23:10) Reading to find excerpts (26:01) Curation & creation (31:03) Seeing a mirror in others’ ideas (34:10) Living in the present (37:26) Combining a known and unknown (39:34) Six at 6 themes: deconstructing creativity & putting in the work (43:06) Balancing the art & audience feedback (45:15) Don't “step into the character” (50:02) Taking the next step & writing his first book (55:45) The work is the win (58:13) Fear of not finding the right stories & concepts (01:00:02) Working with Rick Rubin (01:07:34) Orson Welles & ignorance; Paul Graham & not putting up with BS; authenticity (01:13:24) Qualities of a good research & writing assistant; get excited by what others find boring (01:20:50) Doing it because it’s a compulsion (01:24:10) Find your boredom dopamine

—

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 murdering” AI, wire heads vs. pioneers (06:06) Interest in starting his own “pioneering” company (08:37) Make something people want, solve problems for yourself (12:51) Solve the biggest problem in your area of competency (14:49) Authenticity; know the story you’re telling & believe it (21:39) Ozempic for risk tasking (25:09) Take the easy roads off the table, redirect entrepreneurial energy (31:41) Comfort is uncomfortable (34:33) Must satisfy curiosity (38:12) Techno optimism, painting a more positive future (46:13) Capitalism 2.0 (47:58) YouTube, profiles, & podcasting (57:36) Going from video essay to documentary (59:39) His new venture (01:05:31) What do you actually want?

—

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 (13:40) Recognizing essential sameness; focusing on non-striving and not goal-oriented living (23:21) Deep Okayness, self acceptance, and “The Other Thing” (27:55) You don't shed your person — you just develop a different relationship with them (30:26) How much impact does coaching have? (34:03) Bypassing the illusion vs. everything is here now (38:27) Hitting publish even when hesitating & it's imperfect (42:43) Recognizing the neuroticism & worrying; relaxed writing (44:56) Fragrance as an art form

(49:25) What’s the uncomfortable thing you want to do?

—

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, macro and micro experimentation, copying vs. being original, sabbaticals, and knowing what you want.

—

(01:11) The longevity of YouTube (10:46) Building Jubilee Media, the “Disney of Empathy” (14:33) Micro & macro experimentation, emotions, & competitive analysis (29:14) Copying vs. being original & unique (36:58) Why leave Jubilee? What is Hashemi Studios? (42:43) Ryan's unique skill set (48:29) The 80/20 on creating content early: bottoms-up approach to competitive analysis, plus focus on CTR and retention (55:14) Raw, authentic vs. edited, scripted content (01:01:22) YouTube channels as variety shows; format expansion (01:06:29) Podcasting on YouTube (01:13:31) Sabbaticals: find what you like, talk to people, & prioritize health (01:20:03) What is it that you want?

—

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; authenticity (14:11) Comedy lets you say things indirectly (17:37) Being a creator vs. using content for entertainment & sales

(21:46) Laskie & recruiting inefficiencies (27:23) The tweet & DM that led to Laskie's acquisition (35:33) Capturing more value in hiring on X (45:01) Assessments in hiring (52:47) Opportunities to disrupt multi-billion dollar staffing companies (01:02:03) Criteria for finding problems to solve (01:08:07) Passion for space, customer or business model vs. a specific solution (01:14:02) Are you working on something that is valuable to the world?

—

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, experimental episode. So, this is a collection of a bunch of asynchronously recorded audio messages on the platform. It’ll probably feel different in a couple of ways, and it’s shorter than normal, but it was a blast to record. Please enjoy.

—

(00:55) Connecting with Naval & Brian (02:45) Airchat & audio (04:30) HS drop out (06:01) Reimagining learning (10:56) How to make progress & organize (11:37) Living with uncertainty (12:42) Protecting means of knowledge creation (14:00) Truth vs knowledge (16:37) Arbitraging zip code & credentials (18:46) Big quests: education & longevity (22:16) What plans is your past self still working on

—

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 (05:34) Do a 9-5 and side hustle (08:32) Work for a large company and a small one (10:15) Everyone should travel & write (15:08) Before and after you have money (21:27) Getting an MBA & being around other high agency people in real life (30:32) There’s too much anti-university sentiment (32:30) Whoever has the most fun wins (40:18) Opportunity costs & trade offs he’s comfortable with (44:51) Mixing marketing & authenticity (49:50) Using satire to get messages across; laughs and depth (54:32) The Internet changes how we react (57:45) Working backwards from regrets (58:56) Publishing a book (01:04:27) Having a miniature media company; develop writing skills (01:10:35) Final question

—

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 Twitter

(05:23) Changing habits & cultivating a refined sense of disgust

(10:09) Leaving Twitter leaves a hole in your habit structure; news, reading, silence

(15:25) Habits

(21:28) Planning too far out in startups is harmful

(25:37) Failing is painful but uncertainty is where the rewards are

(34:43) The media’s portrayal of innovators & change makers

(45:08) Just make a better product

(48:28) AI is advantageous for the incumbents, unless you find a different use case

(52:45) Every company is a series of companies

(56:35) AI CRM

(59:23) Spaced repetition social network

(01:03:43) Not paying attention to the news; Redirect energy from “the current thing” to something more productive

(01:09:58) Decide what's fundamental & interesting vs. a fad

(01:18:03) Think for yourself

—

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 overcome hurdles

(05:14) You can't give up

(06:29) Do one small thing & one new thing every day

(09:29) Explore & exploit; using YouTube to get to cinema

(12:47) Skills he’s mastered vs. need more work; remember that you know how to do it

(16:59) The evolution of his filmmaking: from gaming to documentaries

(22:37) Balancing your story vs. the subject’s

(25:54) Removing elements & tools and adding them back later

(32:05) Never have preconceived ideas about someone else's story

(34:02) When is a video ready to publish?

(36:45) Take people on a journey, from sad to inspired

(38:11) Making what you want vs. for the audience

(42:11) Tradeoffs of excellence; no sacrifices

(44:59) Creativity isn't a skill you can ever master

(47:34) Processes vs. goals

(49:23) Biggest fear: losing the confidence & ability to create

(52:30) Knowing your main tool in your toolbox

—

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 randomness, procrastination & creativity (14:52) Measurement & efficiency over experimentation & invention; the growth of bureaucracy (27:54) Working from home (41:55) We aren't rational or irrational (45:10) Psychology & behavioral science don’t need a theory of everything — just a better map; changing social norms (49:52) Young people want absolute, context-free rules on everything (55:20) Shrinking advertising budgets limits unique discoveries (01:01:42) Evolutionary biology; looking at past events & understanding preconditions (01:14:18) Mariachi bands & more creativity

—

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 vs. tapping into an innate one (08:17) Magical internet money (11:12) Going from a bootstrapped lifestyle business to venture-backed company (14:40) Breaking down problems (19:04) Pareto principle & compound interest (23:02) Know what hat you’re wearing & how to navigate interpersonal dynamics (28:26) Look for synergy (33:37) Finding audience-content fit is a cheat code (36:55) Marvel's Cinematic Universe is a blueprint for creators (41:10) Creators need different skills to take it to the next level (43:06) Competing priorities in content creation (45:39) Global supply chain complexity (50:56) Be honest about what you want

—

Kevin’s Twitter: https://twitter.com/KevinEspiritu

Epic Gardening: https://www.epicgardening.com

Epic Gardening’s Twitter: https://twitter.com/epicgardening

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 virtuosity & experimentation

(37:34) Getting more in tune with your calling; there are only so many high agency people

(49:08) Don't be programmed by the institutions of programming

(51:56) Living at the extremes & thinking with greater stakes & agency

(58:15) Ambient learning

(01:02:19) Understanding value & re-defining your relationship to money

(01:07:20) Do it for the lulz

—

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) What’s the objective of public education vs. what should it be?

(09:36) Kids are “universal explainers” (13:39) Enjoyable spaces > curriculum (16:43) Learning needs meaningful context & application (21:20) How he gets his daughter to read (26:54) Knowing how to create value; entrepreneurship as a meta skill (33:51) Helping more people find meaning in the work; the importance of uniqueness (41:14) The value & challenges of an in-person education startup (49:37) Public education vs. Moonrise model (55:33) Importance of beauty & design in education (58:28) Tech is a blank canvas (01:06:32) Identify the right actions to live the best possible life

—

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 barriers have been lowered; networks & relationships are a moat (14:44) Why don't we have more world-class, capable founders? (19:49) Talent vortexes & curiosity (26:55) Triangulating people’s careers & admitting you were wrong (29:35) Doing what's profitable vs. good for humanity (34:08) Religion vs. science/technology is a matter of altitude (37:23) What’s always true in venture, and what won’t be in the future (45:21) Writing vs investing (47:05) Writing, reflecting, & changing behavior (53:52) Crossing out every day on the calendar (56:24) Only take opportunities that stick around (01:01:39) Regret minimization (01:03:18) Kyle’s final question for listeners

—

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) Identifying & getting the attention of world-class people: pursue deep relationships with people you admire (05:55) Operating vs. investing; exploring vs. exploiting (08:49) Are you running towards or away from something? (12:15) Criteria & considerations for what's next; the rubber must meet the road (16:02) What is the core meme he wants people to think of when they think of “Jackson” (22:36) Pulled in two directions; preserving optionality & finding your edge by combining interests (27:06) What does he want to be closest to #1 in the world at? (29:46) Change is accelerating & how to navigate it; maintaining openness (39:46) Curators and audiences; outsourcing thinking (50:49) Moving agency on the margins (53:28) Are parasocial relationships healthy? (01:03:20) How to optimally use the internet for friendships & extending those into the real, physical world; proximity is undervalued (01:10:33) Incentivizing the creation of more art; impact of AI on art (01:17:02) The beauty of film (01:21:49) Jackson’s final question for listeners

—

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, bootstrapping, and being able to focus on building (05:00) Market insights the incumbents didn’t have (07:35) Biggest problems for creators today across creation, distribution, and monetization (09:41) Being adaptable in supporting creators (13:16) The biggest problems in podcasting (16:53) Quality, trust, entertainment & analysis as a moat for creators in the age of AI (19:22) Individuals vs institutions (21:28) Email allows you to own distribution (25:09) Overlooked or under-appreciated parts of being a CEO (27:59) Ride the wave of hunger & ambition while you’re young & free (32:18) Is passion portable & the importance of luck and opportunity (34:18) Being in over your head & choosing the more difficult path (38:32) Comfort vs. stress (41:59) Credentialism vs. proof of work (45:54) The importance of ignorance & naïveté (48:15) Retaining authenticity & getting in the weeds (51:04) Problems in the music industry (53:08) What are you uniquely positioned to do

—

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+ businesses instead of 1? (04:38) Everyone is a capital allocator whether or not they know it (07:13) Impact of VC on startup growth trajectories & sustainability (16:18) What's misunderstood about building holding companies (19:29) Long term thinking (23:40) Focus is the founder master skill (27:56) Work in the medium, not the abstraction (31:14) The fear of reinventing ourselves (36:02) Build organizations that last (38:03) Legacy publishing & acquiring Scribe Media (46:22) Building an audience (52:29) Should books evolve? (56:06) Why Africa is the future (01:00:41) Children reintroduce parents to play (01:03:00) How can you be more human?

—

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 how to get it (10:58) Agency is about seeing a path forward & being willing to fail (16:42) Draw 100 owls (19:55) How to find your thing (25:21) Small talk & knowing the environment where conventional norms come from (30:00) All problems are coordination problems (37:42) Geography is still important (41:48) What's Paul Graham's next essay? (44:00) Are parasocial relationships good for humanity? (48:16) We need to articulate a positive vision of the future (50:04) Positive-sum games

—

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 (33:30) Oscillating between seriousness and unseriousness; being authenticity (39:46) Fun as motivation & using the skills/aptitudes you're given (42:22) 80/20 analysis on good storytelling; find the thing you've got good taste in (51:09) What breaks relationships (57:29) Maintaining openness in relationships (01:02:00) Becoming a better podcaster (01:06:33) Repeat struggles with podcasting (01:07:51) Final question

—

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 the first time (09:24) Children are capable (12:27) We underestimate children because they’re alien to adults (15:28) Creating an environment for children to thrive (19:38) Agency is not just about picking from the menu, but also about how you eat (25:52) Teaching backflips & the expert decomposition of tasks (29:46) Can most things be learned through systematized instruction? (35:03) Lots of things are instructional design problems, but education as a field is young (37:51) Experimentation & innovation in education; conservatism (44:03) Homeschooling (48:48) The role of the parent vs teacher (52:11) The importance of work (57:27) The good life (01:02:54) Matt’s final question for listeners

—

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 the process (08:46) Self-excavation & tracking your evolution (10:48) What's core to your identity vs. malleable & a result of your environment (13:52) Suppressing sensitivity (15:40) Pseudonymity & keeping your identities separate (17:14) High vs low self-monitoring (20:22) Becoming more heart-heavy (29:01) Find people who are free in different ways (34:07) Living in the present (37:55) Reflecting vs. living (41:42) Curiosity vs. efficiency (45:02) Disposability vs. depth (48:31) Is it ego or is it meaning (51:24) Overanalyzing yourself (54:09) Awareness, agency, & curiosity (56:15) Finding wisdom (58:25) Nicole’s final question

—

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) Having faith, following your gut (23:38) Pseudonymity (35:33) Curating your info diet & parasocial relationships (41:59) Doing things that feel authentic (50:53) The benefits of audio (56:15) Jake’s final question for listeners

—

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 (06:09) Feeling like podcasting isn't building something of value (10:15) Following curiosity vs playing status, money, or power games (16:00) Share your work publicly (16:55) You must have skill to get noticed (19:47) Asking what the world will look like in 2100 (22:40) Breadth vs depth, local vs global maxima (25:11) Evolving your maps & models of the world; focusing on science & tech (27:08) AI optimism (30:06) AI research & regulation (31:46) Other opinions about the future (36:16) Why the initial interest in talent? (38:01) Do the one big thing that stands out (48:02) What makes for good research, questions, and interviews? (52:50) When to podcast vs. write (55:25) Asking good questions, learning fast, and finding the interesting parts to highlight

—

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 (07:28) Can we listen to our intuition more intently, rather than learning through experience? (09:52) Joseph’s Campbell's Hero’s Journey as a guide for life; curiosity & the call to adventure (13:57) The pursuit of curiosity is where you find a life worth living; science of meaning & curiosity (18:21) Brett Andersen's theory & updating models to get closer to reality (22:46) Movement towards complexity; life is a process (23:57) Complex vs complicated (26:02) What does reality deem valuable? (30:49) Operating optimally as an individual in a complex system (33:47) Does everyone really have value to add to the network? (42:13) Left-right brain hemispheres; paying attention to external cues (45:34) Use energy as your guide

—

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) Why work on this problem? (04:10) Using “extreme environments” to understand concsciousness (and other hard problems) (07:46) Why do we dream? (09:42) Becoming more agentic through lucid dreaming (12:04) VR/XR vs. lucid dreaming (16:00) Potential negative scenarios with neurotechnology (19:29) Why would we not use lucid dreaming as an escape? (23:19) Consciousness-to-consciousness interfacing (26:55) Epistemological metaphysics (31:11) Barriers to epistemological metaphysics (33:19) How we answer questions about consciousness, reality, and “who am I?”

—

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, being addicted to your craft, power, living life like a work of art, and more.

—

(00:40) Why podcasting? (02:28) Why not YouTube? (04:08) Being “Tim Ferriss for dead people” (05:52) Getting people to notice (07:17) What’s the goal of HTTOTW? (09:16) Focus & speed (14:55) Getting to the point of contact quickly (17:51) Addiction (23:39) Research (25:12) Anti-characteristics we should avoid (29:38) What creates great people? (34:26) Power is freedom (39:05) Finding your groove, raising people's ambitions (43:32) Ambition vs. being well-balanced (49:52) Living life as art & Horatio Nelson's death

—

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) Research & the scientific method (06:31) Building on the shoulders of giants & adding your own perspective (10:40) Her unique perspective on productivity & work (13:45) Mindful vs. traditional productivity (15:53) The importance of metacognition (20:15) Small experiments > finding your passion (24:51) Redefining ambition (28:44) Decoupling your self from the experiment (32:17) Ambition vs. contentment (35:42) When to start a new growth loop (40:36) Combining perspectives from different fields (44:29) Anne-Laure’s final question for listeners

—

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? (04:58) The challenges of solopreneurship & content creation (07:49) Why you don’t find your niche (10:04) All good things are hard & difficult (12:36) What's he (not) optimizing for (15:13) Would he ever turn this into a large, multi-person business? (18:17) Mimetic desire & playing your own game (21:16) Is the experience & journey towards your own authentic desire unavoidable? (22:56) Avoiding the disease of more & not getting blinded by growth (25:20) You can't fast forward reality (28:24) Are there downsides to status and internet fame? (31:22) His business wouldn’t grow without the personal brand (33:36) Why he chose not be a parent (36:09) What he likes about travel & how to emulate the benefits elsewhere (40:46) Investing in local communities & helping people abroad learn how to use the internet (44:42) Justin's final question for listeners

—

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 friends, freedom, commitment, and the balance between introspection vs. action.

—

(02:47) Starting a venture capital firm instead of a startup (05:51) Career sunk cost fallacy & thinking of your life in projects (09:36) Famous among friends, picking people you don't have to explain yourself to (13:29) When to take advice vs. forge your own path (17:27) Increasing agency (22:32) Project-based learning & optimizing for failure (26:32) Breaking out of off-the-shelf games (30:14) Better models for funding people directly (36:02) Investment thesis: vertical SaaS, wealth transfer, AI category creation (41:46) Generalists vs. specialists, T-shaped people (45:46) Balancing the rational & emotional (50:39) Freedom (54:22) Closing the interest gap with commitment, having low expectations (58:14) Introspection vs action (01:01:54) Molly’s final question for listeners

—

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 on product (07:14) If you're an industry expert, you can become a creator (09:37) Workweek vs. being independent (14:27) Attributes to look for in creators (17:49) Consistency in content creation is under-appreciated (19:14) Choosing your mediums, platforms, and monetization strategies (24:28) Identifying niches (27:52) Industry focuses (29:44) VC-backed vs bootstrap (33:45) Inspirations (35:56) Being a creator & employee (38:30) Biggest challenge for Workweek over next 12-18 months (39:58) What does Workweek look like in a decade? (41:38) Choosing to commit 7-10+ years to this problem (43:52) What other problem in the creator space would he be working on? (46:44) What will look the same/different about creators in a decade (48:15) Adam’s final question for listeners

—

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 brand as big as Disney, and more.

— (00:34) How to find your obsession (02:16) His creative process (03:54) Using intuition and data (04:50) Knowing when to experiment & make big changes with your content (06:42) Experimenting & growing is just as important as consistency (07:54) His inspirations (12:52) Disney (15:27) What the obsessed brand look like 10 years from now (17:27) Leveraging AI for content creation (19:41) His biggest challenge: monetization (21:11) What he learned from his photo booth business (24:00) Having a long term mindset (25:31) Talking about obsession obsessively (27:04) Cult and community building (31:23) Knowing when to surrender (33:29) Drawbacks & tradeoffs of obsession (37:05) Winning the game with yourself & building something bigger than yourself (39:20) Take less advice, consume less content (40:23) Zach’s final question

—

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 contentment and ambition, and more.

—

(00:48) Building a community of 1000 friendly, ambitious, nerds within walking distance of one another (04:44) Why do we look so few people — especially friends — in the eye every day? (09:33) Seeing friends should be easy and fun (10:18) “Reversing the centrifuge”: why we're here and how we change it (16:24) Finding the right social technologies for your objectives (18:19) What are the small details you have to get right in physical communities? (21:08) The financial and governance systems they're using (and how that may change when they scale) (27:50) Is or will there be an online community? (30:26) Mitigating loneliness, obligation to humanity, and pooling social capital (34:54) Being content and ambitious (40:07) Can and should we encourage people to be less fearful? (42:37) Andrew’s final question for listeners

—

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 about the future, cooperation and coordination, increasing agency, commitment, and identifying what you’re good at.

—

(01:04) Why do we need better human coordination? (06:25) Straddling the line between optimistic and pessimistic; being “pro” things instead of “anti” (12:23) Stories drive cooperation (15:51) Does he have a fundamentally good view of human nature? (20:24) How to increase human agency (27:10) How and when do you know to commit to something? (33:33) Identifying what you're uniquely good at (37:57) Rich’s final question for listeners

—

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.

—

(00:38) Gurwinder’s background

(03:59) Language as the programming language of humanity

(11:21) Do humans want to recognize the bugs in our OS & can we convince people to want to do it?

(14:16) How much can we actually change our operating system?

(30:07) Are our emotions ever valid?

(32:01) What is intuition and is it useful?

(41:56) Are there systems & institutions that can help the rewiring of humanity at scale?

(54:33) How do you know where to draw the line in finding truth vs. trusting sources?

(56:25) Gurwinder's final question for listeners

—

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 the right place to build these ventures.

—

(00:50) Alpha’s background (04:59) What is Temple? (08:45) Why Africa (and Nigeria in particular)? (15:00) What's the right mix of private and public involvement to make this succeed? (18:50) Picking what to own; first principles vs. leaning into expertise (24:30) Temple's ideology & ethos (29:24) Recent city-state case studies (36:09) Pre-mortem: what could failure look like? (40:38) What do you have to get right at the beginning? (47:59) Balancing domestic & foreign talent (54:16) His first crack at Temple (58:10) Types of ventures he sees being built as a result of Temple (01:04:07) 20th century governance & infrastructure vs. 21st century technologies (01:10:57) Alpha's final question for listeners

—

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 to realize its true potential (12:25) We need clusters of independent yet connected communities encouraging pro-social behaviors (18:16) Change comes from small, bottoms-up movements (26:25) The next round of recruiters for the scene (29:04) Historical scenes & outliers, and how to manufacture more of them (34:44) Being authentic & informal, & attracting intrinsically motivated people (43:03) The lifecycle of sub-cultures (46:44) Accepting & encouraging deviants (55:26) Writing Friendly Ambitious Nerds and Introspect to Introspect (01:02:26) What he wants to write next (or rather, what wants to be written) (01:07:13) Trying to become more ambitious, & the tradeoffs of improving your strengths or weaknesses (01:20:13) Visa's final question for listeners

—

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 background (02:21) Her novel (03:40) Going from creative outlet to 100s of subscribers (06:40) Has her writing evolved with the growing audience? (10:01) Why she hasn't gone full time on writing yet (14:10) Writing authentically & vulnerably (19:30) Honesty, clarity, and emotion (23:33) What you read heavily influences your writing (25:38) Commitment & focus - finding the thing to commit to (28:58) Do 1-2 things really well & differentiating between what you find intellectually interesting vs. can actually see yourself doing (33:48) The dating game & what needs to change (38:31) Love vs. attachment & three definitions of love (41:58) How AI will impact relationships, love, & intimacy (50:01) Beauty, precision & rigor, & expression (51:34) Ava's final question

—

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) Michael's background (02:25) Why he was drawn to Alexander Technique (04:36) What is Alexander Technique? (07:05) The challenges of repurposing the technique for broader use & teaching it online (09:01) Metaphors for getting people "there" (11:57) Why we aren’t normally in a state of expanded awareness (14:58) Can awareness be permanent? (19:20) Common blockers to cultivating awareness (21:27) Non-doing & effortless effort (24:12) (un)consciousness & (un)naturalness (27:34) Can we pre-empt the need for “unlearning”? (30:40) Do we lose anything by being over-aware? (37:31) The relationship between awareness and flow (41:29) What Alexander Technique isn't & what it could be (45:13) Where Alexander Technique fits with traditions like Buddhism and Taoism? (48:43) Being emotional vs. rational (52:58) Going from consultant to teacher-solopreneur (58:09) Archeologists vs. architects (01:04:38) Michael's final question

—

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) Lenore's background (02:17) Free Range Kids and Let Grow (12:02) The root causes of social & parental fear re: children's independence (20:50) How to mitigate fear & change parental behavior (21:26) The statistics (33:25) The importance of agency (38:36) Peter Gray's research & the impact of independence later in life (46:12) The two major Let Grow projects (50:22) Independence online (52:06) Lenore’s question for listeners

—

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 aligns with his purpose

(24:23) How he and his wife chose intentional living

(29:28) How helpful are other people’s journeys?

(32:38) Whether society cares about psychological development

(34:45) Why he's optimistic about humanity becoming more aware

(44:38) Ikigai 2.0

(54:36) The birth lottery

(01:08:02) Free will & agency

(01:22:36) What he's seeking now

—

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 & buying SaaS

(01:40) Why the partnership with his co-founder works

(02:34) Investment thesis

(03:37) The investment he's most excited about

(04:12) Dream investment

(05:42) Why SaaS

(06:46) What he's learned from Andrew Wilkinson and Mark Leonard

(08:27) Proprietary deal flow

(09:46) Why he creates content

(10:53) 80/20 on due diligence

(12:48) How to avoid sunk costs in deal negotiation

(14:00) Ensuring a smooth transition post-acquisition

(16:49) How to scale and delegate

(18:10) What can be taught about buying SMBs

(19:51) How people should get into the space

(21:20) Building gradually

(24:10) Biggest challenges

(25:02) Missing infrastructure in SMB acquisitions

(27:37) The biggest reason they’ll succeed

(28:21) His definition of success

(29:08) How having a kid has changed his thinking about work

(31:04) His early parenting advice

(32:28) Final question & the work he's done to figure out what game he wants to play in life

—

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 Substack & podcasting offer compared to academia

(13:18) How he's such a prolific creator

(17:15) Why Judaism?

(18:41) Is there any conflict between obligation & the pursuit of truth?

(21:45) The decline of religion

(27:04) Knock-on effects of declining religiosity

(39:41) Reconciling Judaism & secular philosophy

(42:13) Being a bridge between the secular & the religious

(44:17) What's the goal of philosophy?

(48:52) Why aren't more people engaged with philosophy?

(53:15) Has philosophy “progressed”?

(55:38) What's the meaning of all this?

(58:54) Final question for listeners

—