John Koenig is the author of The New York Times' Best Seller Dictionary of Obscure Sorrows, a dictionary of made-up words for emotions that we all feel but don't have the words to express. We talk about his book, identity and individuality, contradiction, writing, the human experience, fatherhood, and more.

—

(00:44) Why use "sorrows"?

(02:51) Did he ever expect the dictionary to be what it is now?

(05:48) Existential wonderment and loss

(08:50) Truth, internal dialogue, and contradiction

(14:00) Contradiction of definitions

(17:02) Is introspection valuable? Can you know who you are?

(20:43) Not focusing on the present

(24:18) Self-actualization vs. contentment

(30:26) How you perceive people vs. how they really are

(35:57) Next book: Sonder

(39:03) Does sensitivity make life more difficult?

(41:54) Career identity & pigeonholing

(44:24) Writing vs. video

(47:32) How fatherhood changes work & focus take on his work; finding meaning in community & ritual

(51:25) Where does meaning reside?

(53:27) Creative process takeaways for kids; self-expression and art

(55:15) John's final questions for listeners

—

John’s Twitter: https://twitter.com/obscuresorrows

Dictionary of Obscure Sorrows (Amazon): https://www.amazon.com/Dictionary-Obscure-Sorrows-John-Koenig/dp/1501153641

YouTube: https://www.youtube.com/c/obscuresorrows

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com/

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

—

Dylan’s Twitter: https://twitter.com/DylanoA4

Essayful: https://www.essayful.co/

O'Shaughnessy Ventures: https://www.osv.llc/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Steve’s Twitter: https://twitter.com/schlaf

Personal Site: https://www.schlaf.co/

Downshift: https://www.downshift.me/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Matt’s Twitter: https://twitter.com/matthewclifford

Entrepreneur First: https://www.joinef.com/

Personal Site: https://www.matthewclifford.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Joscha’s Twitter: https://twitter.com/Plinz

Joscha's Substack: https://joscha.substack.com/

Personal Site: http://bach.ai/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Gabe’s Twitter: https://twitter.com/VividVoid_

Gabe’s (Old) Blog: https://vividvoid.substack.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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?

—

Nathan’s Twitter: https://twitter.com/nathanbaugh27

Nathan’s Newsletter: https://www.worldbuilders.ai/

Vonnegut’s Shape of Stories: youtu.be/oP3c1h8v2ZQ

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Billy’s Twitter: https://twitter.com/bpoppenheimer

Six at 6: https://billyoppenheimer.com/newsletter/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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?

—

John’s Twitter: https://twitter.com/johncoogan

John’s YouTube: https://www.youtube.com/@JohnCooganPlus

John’s Podcast: https://open.spotify.com/show/2JcCU31J07hCMxw99RWVRk

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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?

—

Sasha’s Twitter: https://twitter.com/sashachapin

Sasha’s Site: sashachapin.com

Sasha’s Substack: https://sashachapin.substack.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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?

—

Ryan’s Twitter: https://twitter.com/ryanhashemi

Ryan’s Newsletter & Hashemi Studios: https://www.ryanhashemi.com/

Jubilee Media: https://www.jubileemedia.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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?

—

Chris’ Twitter: https://twitter.com/ChrisJBakke

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Arjun’s Twitter: https://twitter.com/arjunkhemani

Arjun’s Site: https://arjunkhemani.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Jack’s Twitter: https://twitter.com/Jack_Raines

Young Money Blog: https://youngmoney.co

Exec Sum: https://www.execsum.co/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Michael’s Twitter: https://twitter.com/micjm

Bottomless: https://www.bottomless.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Danny’s Twitter: https://twitter.com/dannymcmahon

Dodford YouTube Channel: https://www.youtube.com/@DodfordYT

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Rory’s Twitter: https://twitter.com/rorysutherland

Rory’s books: https://www.amazon.com/Rory-Sutherland-Books/s?k=Rory+Sutherland&rh=n%3A283155

Ogilvy: https://www.ogilvy.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Wolf’s Twitter: https://twitter.com/wolftivy

Palladium Magazine: https://www.palladiummag.com

Palladium’s Twitter: https://twitter.com/Palladiummag

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

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

—

Chris’ Twitter: https://twitter.com/_cturner

Moonrise: https://moonrise.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com