Audience of One

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 t...

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 y...

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; peop...

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, unl...

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...

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 n...

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) St...

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...

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...

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; fo...

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...

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...

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 bunc...

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 l...

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 & cultiva...

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 (...

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)...

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 in...

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...

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 s...

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 & relations...

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 p...

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 bu...

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 a...

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...