Rob Henderson is one of my favorite up-and-coming writers. I like him because he's one of those people who doesn't fit into a category. He's a Ph.D. candidate in psychology, but I met him in a book club about technological stagnation. He's spent years in the academy, first at Yale and now at Cambridge, but most of his influence comes from his online writing.

Most of all, he's interested in human nature. In particular, psychology, status, and social class. Those interests come from his background. During his childhood, he bounced around between foster homes in California. After working as a busboy, a dishwasher, and a supermarket bagger, he joined the Air Force at the age of 17. After his enlistment, he ended up at Yale and now, Cambridge. Please enjoy my conversation with Rob Henderson.

This week, I have two guests. Both are affiliated with Synthesis, a new kind of online school where kids learn through games and simulations. One is Chrisman Frank, the CEO of Synthesis. The other is Ana Lorena Fabrega, who is their Chief Evangelist.

Here's the backstory: A few years ago, Elon Musk asked the co-founder to start an experimental school with him at Space X. The goal was to develop students who are enthralled by complexity and solving for the unknown. Synthesis was the most innovative learning experience from that school and spun off into its own company. In full transparency, I'm an investor.

This episode presents a vision for the future of childhood education, enabled by the Internet. Please enjoy my conversation with Ana Lorena Fabrega and Chrisman Frank.

Ash Fontana is an entrepreneur, investor, and author. As an entrepreneur, he was only of the early employees at an online investing platform called AngelList. From there, he became the Managing Director at Zetta, the first investment fund focused on artificial intelligence. Now, he's the author of the AI-First Company.

This conversation is about that book. Ash says that AI-First companies are the only trillion-dollar companies, and soon they will dominate even more industries, more definitively than ever before. But we don't just talk about the book. We also talk about health, continental philosophy, and Ash's obsession with bicycling. Please enjoy my conversation with Ash Fontana.

My guest today is Li Jin, the founder and managing partner at an early-stage venture capital firm called Atelier.

She's known for her extensive writings about the Passion Economy.

Her essays explore how people can make a living from their passions and creative skills.

All of her writing is filtered through the lens of consumer startups and the technology industry.

In this episode, we explore Li's perspective on the future of the creator economy.

We talk about what it'll take to build a middle class for creators and how platforms should enable creator monetization.

But then we venture beyond the world of work and discuss the novels of Jane Austen, what Li learned by growing up in Pittsburgh, and why she thinks social media and content creation are valuable pursuits.

Please enjoy my conversation with Li Jin.

Show Notes: 2:37 - How do content creators get users to migrate platforms and engage in unfamiliar apps?

5:44 - Why is some digital content more consumable than others?

13:07 - What is the driving force behind Li’s background in English literature?

17:34 - Why Jane Austen is so incredibly important to the world of modern creatives

21:56 - What has contributed to the alienation of gig workers in modern economy?

24:57 - Where does Li Jin’s technological optimism stem from?

28:32 - What is an “Angel Investor”, and how do they influence the modern world of content creation?

32:55 - What is the difference between an artist and a creator?

37:44 - How has the modern market created space for content creators?

42:19 - What causes creative burnout in the world of content creators?

50:01 - What are the implications of viral fame in the modern world of content creators?

57:46 - Which aspects of traditional and non-traditional education were most impactful on Li Jin?

1:08:55 - What are some things that both successful and aspiring content creators often misunderstand about the industry

1:14:20 - What are some of the parallels between the worlds of writing and investing?

1:18:08 - How Li Jin embodies the spirit of a malleable fate

My guest today is Zena Hitz, a tutor at St John’s and the author of an excellent book called Lost in Thought: The Hidden Pleasures of an Intellectual Life. Her book explores the meaning and the value of learning for its own sake, through images and stories of bookworms, philosophers, scientists, and other learners, both fictional and historical.

That’s the jumping-off point for this episode. We also talked about the relationship between religion and the Liberal Arts, why studying the Liberal Arts has become so unfashionable among average people, and how an essay about Oedipus Rex inspired her to become an intellectual.

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Show Notes

1:37 - What about Oedipus Rex grabbed Zena's attention and inspired her to pursue intellectualism.

7:05 - What Zena sees as a "good" question in an intellectual frame, and why good materials can get you to them more easily.

9:55 - Why the most profound questions won't show up at the beginning of your inquiry, and how the common person's depth of inquiry has seemed to dwindle since the past.

13:19 - How Zena maintains her attention reading books when it is so easy to be distracted.

17:00 - Why it is decadent, complacent, and undermining to ourselves and our community to pursue education only in what will get us work.

23:53 - How people pursued lifelong learning in the past and why it's even more viable of an option today.

28:07 - What Zena hopes to give to the world at large through her work.

33:51 - How the monumental shifts in wealth and inequality have hindered people's ability to contemplate ideas they deem important.

36:20 - The differences in solitary and communal efforts to contemplate intellectual topics.

39:40 - Why we shouldn't be consuming books, but rather engaging directly with them.

44:03 - Why Zena believes that the idea of a patriarchal or caucasian canon is a myth.

49:02 - How education is a means of training your mind while simultaneously freeing it.

53:04 - The affinity between the liberal arts and religion.

55:11 - Where Zena learned how to write and why she has trouble writing if she doesn't have an audience.

58:42 - How to use writing to improve your thinking.

1:01:30 - Why St. John's has deliberately set itself apart from research universities.

1:05:33 - The crisis in Zena's life that kicked off her political thinking and essays, and why she believes that our current institutions are becoming increasingly disconnected from our humanity.

1:13:23 - What brought Zena to religion when there is a historic amount of people leaving it.

I have two guests today: Tiago Forte and Will Mannon.

Tiago is my business partner and the creator of an online course called Building a Second Brain. The two of us record a podcast like this every year to reflect on what we’ve learned about the online education industry. And this time, we invited our Director of Student Experience: Will Mannon.

Will oversees all aspects of the student experience with the exception of curriculum design. He’s at the frontier of thinking about live online learning, from how assignments should be delivered to how live sessions should be structured.

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Show Notes

3:21 - Why hiring your first employee is one of the most important steps you'll take in your business.

5:38 - How sharing a workforce and resources with another business or entrepreneur can help fast-track personal and professional growth.

11:00 - How running an online course is like organizing a music tour.

13:30 - The role of the alumni mentors in Tiago's courses, and how they have changed from his first to his most recent cohort.

17:16 - What different mentors can bring to the table and why the differences between them all brings strength to the program.

21:03 - Why giving as many people as possible the ability to lead allows much more effective learning for everyone.

25:04 - The nature of burnout and why creatives are so prone to experiencing it.

31:04 - Discovering the right size for a cohort and how to scale effectively.

37:13 - How to help students find each other and make meaningful and lifelong connections with each other.

40:28 - The "beer mode" and "coffee mode" of productivity.

44:32 - How to increase your focus by never giving yourself enough time.

51:02 - Why David and Will organize Write of Passage to have attendees "come for the ideas and stay for the people".

56:23 - Why running a course should be about empowering leadership in students, not in building dependence on the teacher.

1:02:33 - Why the element of shock is so fundamental to deep learning.

1:06:43 - How friendship can come so readily out of hardship and pain.

1:11:33 - The unusual growth of David and Tiago's online brand this year and what sparked it.

1:14:45 - Why writing a book summary for Tiago is so integral in internalizing the information and the message contained within it.

1:24:22 - What hands-on education and perseverance in the face of extreme difficulty can teach us that traditional education never can.

1:32:30 - What we can learn about education from businesses and markets outside of the educational sphere.

1:36:33 - Why success in a new business should not be focusing on competition, but on radical differentiation.

1:39:23 - The importance of finding your community online and curating it to inspire and inform you.

My guest today is Gagan Biyani, the current CEO of an education startup (where I’m both an investor and an advisor) that helps teachers run Cohort-Based Courses on the Internet and has students from around the world. Gagan also founded a multi-billion dollar online education platform called Udemy. Afterward, he founded Sprig, a food delivery platform that grew to a nine-digit valuation but eventually failed. So today, he has the distinct pleasure of being both the founder of a unicorn and the founder of a massive failure.

In this conversation, we talk about what he’s learned playing the Silicon Valley startup game. Then, we talk about our visions for the future of the online education industry, and how he's learned so much about cooking and restaurant operations. Please enjoy my conversation with Gagan Biyani.

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Show Notes

2:11 - How Gagan comes up with and develops his startup ideas.

7:38 - Why Gagan believes that the market is the best thing we have, but that it is still deeply random and flawed.

10:14 - The lessons we should be learning from Silicon Valley and what people in Silicon Valley need to learn themselves.

14:51 - The dogma and necessities of startups that Gagan has seen in Silicon Valley that are proven to be untrue.

21:17 - How the duality of total rationalization and going with your guy fits together.

25:18 - How the "soul" plays into optimizing our lives and why Gagan sees the future of human connection.

30:50 - What inspired Gagan to become fascinated and so knowledgeable about food.

35:58 - What changes when making food at scale and why recipes don't multiply easily.

43:01 - What Gagan looks for in determining whether a restaurant is worth going to.

47:41 - How lifelong learning changes the way you see the world.

52:22 - Why the way a company does one thing will show you how it does everything.

56:17 - Why knowledge should be something that is shared, not something that pushes people away.

1:02:54 - How the classical cohort-based learning model has evolved on the internet.

1:09:35 - How colleges and traditional institutions are adapting to the new learning paradigm.

1:11:03 - What Gagan envisions in an ideal future-thinking educational company.

1:22:45 - How cohort-based courses can be improved and where Gagan saw these flaws in his own and in other courses.

1:26:17 - What in Gagan's early life made him so driven and motivated to do what he wanted to do.

1:36:51 - Gagan's trip to the Amazon, and what he learned from the indigenous tribes that he visited.

1:43:01 - The infantilization of different ways of life, and why it is a more ethically dense topic than people realize.

My guest today is Trevor Bauer, who is arguably the very best pitcher in Major League Baseball. In 2020, he had the lowest Earned Run Average of any pitcher and won the National League Cy Young Award, which goes to the top pitcher in the game. I wanted to interview Trevor not only because he's an excellent pitcher, but because he takes a radical approach to the game. He's a physicist and a scientist. A scholar and an entrepreneur. And you don't find that combination very often. Furthermore, he might be the most polarizing figure in baseball. Some people love him; some people hate him. But every fan has an opinion on him. Off the field, he's the founder of Momentum, athlete-driven media company that uses storytelling to connect athletes and fans. To build it, he started a podcast and a YouTube vlog where he talks about pitching mechanics and what it's like to play professional baseball.

Personally, this was one of the coolest episodes I've ever recorded. I grew up as an avid San Francisco Giants fan, and I still remember getting to the field early to get autographs and catch baseballs during batting practice. This interview would have made little 8-year old David proud, and I'm lucky to share it with you today. Please enjoy my conversation with Trevor Bauer.

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Show Notes

2:18 - How Trevor would change the way baseball is marketed and to whom it should be pitched.

5:45 - Why updating the game for a modern audience would be difficult, despite what Trevor believes would be a successful move.

11:23 - Why there aren't many unique fields like in San Francisco or Boston.

15:10 - How baseball is not being evangelized well by the people who could be doing it most easily.

19:51 - How general scientific literacy can and should be improved through sports.

23:28 - What it takes for Trevor to scientifically design his pitches and then implement them in a game.

31:00 - The business of baseball, and how Trevor has learned to maneuver its quirks and difficulties.

37:13 - If could choose anybody, who else in the sports world and beyond Trevor would want to talk to.

42:15 - How Trevor looks into the future to superpower his game.

48:07 - The dangers of getting too in-depth in analyzing your game, and how it can hurt you.

54:43 - Why you should practice analytically and perform intuitively.

56:13 - What breathing techniques Trevor employs in his game.

58:18 - The different aspects of building a business and how Trevor is handling each element differently.

1:07:30 - Why Trevor's actual goals in his work and his game aren't covered by the media.

1:10:44 - How his father helped Trevor succeed in baseball by giving him the tools he needed to work hard.

My guest today is Nik Sharma, the founder of Sharma Brands and an advisor to companies like Judy and Cha Cha Matcha. Nik is one of my very best friends and my go-to person for all things commerce. Since we first met, we've spent hours exploring the future of marketing and commerce together and recorded this podcast to give you a window into what our conversations are like.

We started with Nik's philosophy of launching Direct-to-Consumer brands. I particularly liked Nik's idea of "The Brag Bar" on landing pages, where you can use social proof to sell your products. We also spoke about managing relationships with influencers and finding the supply and demand equilibrium at launch. Towards the end, Nik and I talked about our process for turning conversations into articles, and the time he cold emailed Mark Cuban. Please enjoy my conversation with Nik Sharma.

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Show Notes

2:21 - Why Nik has the "world's craziest fridge" and how it helps keep him in the know on DTC brands.

6:29 - What marketing strategies Nik has found most successful for DTC brands.

13:31 - How brands can differentiate themselves in a world of emerging brands in already burgeoning markets.

19:25 - Nik's approach to launching a successful DTC brand and when to concentrate your advertising versus diversify.

30:19 - The role of A/B testing in building a brand.

35:43 - How influencers play into the big picture of marketing and why the "shaky video" effect is so successful.

42:12 - The selection and audition process of influencers in Nik's campaigns and how he chooses those he sees as the best for his brands.

45:52 - The costs and benefits of starting your brand through heavy promotion via influencers.

49:56 - How the process of rebranding Hint Water's bottle was performed and the qualitative process that got them to the bottle you see today.

57:27 - The metrics and methods Nik uses in his development of marketing strategies with his brands.

1:05:19 - What Nik looks for in a great landing page, and why all landing pages should be easy to read for everybody from a 12-year-old to a drunk person.

1:10:07 - What UGC is and why Nik thinks it is so underrated by marketing teams.

1:13:31 - The different marketing funnels and when you should use each one.

1:17:09 - Why Nik creates landing pages for fake products and makes them live on the internet.

1:22:56 - The importance of having great merch for your brand.

1:26:22 - What about internet culture makes collaborations so successful and popular.

1:34:05 - How somebody can convert a large personal following into sponsorships and meaningful collaborations.

1:35:46 - How new brands should position themselves when huge players like Amazon are in the same space.

1:44:01 - What happened when Nik cold emailed Mark Cuban and how he got an almost instant response.

1:50:46 - How David and Nik collaborate to develop, write, and publish the articles they make.

1:56:14 - Why Nik doesn't sweat the details of his personal brand that much.

My guest today is Kevin Kelly, who co-founded Wired Magazine in 1993 and served as its Executive Editor for the first seven years. As one of the most important futurists of our generation, he's published a number of books including The Inevitable, What Technology Wants, and New Rules for the New Economy which is my favorite one. Coolest of all, he's also a founding member of the board of the Long Now Foundation, a non-profit devoted to encouraging long-term thinking.

We discussed the Long Now Foundation at the end of this episode in a conversation about what it means to be a good ancestor for future generations. A couple of things stood out from this conversation. First, I like how Kevin focuses on clarity above all else whenever he writes. He sees himself as a great editor, and writing is the process by which he discovers what he's thinking. Second, we build off the ideas of Marshall McLuhan who was the founding saint of Wired Magazine. Through McLuhan, we explored Kevin's Christianity, how screens are shaping consciousness, and how our technologies have a gravitational life of their own. Please enjoy my conversation with Kevin Kelly.

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Show Notes

2:22 - Exotropic energy and how Kevin uses it to explain the negative entropy we see throughout the universe.

6:24 - Why California has become the world hub of extropy.

10:33 - The transition from the written word to text and screens and how it affects our psyche.

15:27 - What made Marshall McLuhan's writing so paradoxical and engaging.

18:34 - How science fiction has usurped religious teachings as the modern leader of theological thought.

24:06 - Why our limitation as seeing the future only "through the rearview mirror" is driven by a disease Kevin calls "thinkism".

31:25 - How the Amish have utilized an evidence-based method in their adoption of new technologies.

44:46 - Why technology that we create will always be weaponized in the end.

49:01 - Why Kevin believes that the evidence shows the increase of accessibility of and power in technology has not correlated with our ability to harm.

53:15 - How moral progress is a natural byproduct of technological progress.

57:26 - Why Kevin sees a fundamental transformation in how Maslow's Hierarchy of Needs is thought about and utilized in people's lives.

1:05:25 - Why Kevin's futurology is much closer to simply noticing the present that it is divination.

1:15:20 - How moving away from improving everything's efficiency is against the very things we desire as humans.

1:23:35 - Why writing for Kevin is nothing but a means to an end to discovering his thoughts.

1:29:43 - How thinking with 'the long now' can help us become better ancestors and leave a better world for the future.