North Star Podcast

My guest today is Ryan Holiday. He’s a writer, media strategist, and the author of ten books. He dropped out of college at 19 years old to apprentice under Ryan Greene, author of Mastery and The 48 Laws of Power. He worked at American Apparel and founded an agency called Brass Check. We begin this episode talking about two stories from Ryan’s book, Stillness is the Key. One is about Michael Jordan and the other is about Winston Churchill. Then we transition into new topics. We talk about the philosophy of stoicism, the benefits and drawbacks of anger, and what Ryan has learned from Peter Thiel. Please enjoy my conversation with Ryan Holiday. -- --  1:32 Winston Churchill – the busiest man in the 20th century: saw the last British Calvary charge, writes 10 million words, holds office for 65 years, elected Prime Minister twice, painted 500 paintings etc. 7:06 Can a change of location effect your relationship to time?   12:37 Writing as zero-to-one and the importance of getting something down in order to gain momentum. 17:02 Michael Jordan’s Hall-of-Fame Speech where we learned how importance anger as fuel and making a career of hanging onto slights was to him. Could Michael Jordan have been Michael Jordan without these characteristics? 20:30 How widespread is anger as fuel to success? Is it the best method and how much correlation is there to someone’s success? 27:20 Anger as a “purity” in our current political landscape. 29:08 Taking a look at the history of change and how the News may not be the best way to stay informed. Is the current understanding of “being informed” is a vice rather than a virtue?   36:20 To be “informed” need to have basis of understanding before interacting with News sources in order to contextualize and not come at news with hubris. Problem of the twitter approach to news: a profession, reporting, that was once about thoughtfulness, nuance, and the long-form has been boiled down to 280 characters.   41:19 Stillness is the Key as part of a trilogy involving Ego is the Key and The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph. This trilogy was what Ryan had always intended to write but had to go through his other books to get where he is now. 46:35 Truly integrating stoicism into his everyday life.   53:18 Peter Thiel’s brain is in a perpetual Mexican standoff where two competing ideas are constantly in opposition. Thiel seems to have a great ability to frame subjects correctly. Eric Weinstein's idea that Thiel is the world's wealthiest applied philosopher. 58:00 Extending Thiel’s First Principles Movement by simply reading different things than what everyone else is reading, gathering different materials. 1:00:02 Is there a danger where reading history becomes the same thing as watching the news? Ryan’s interest in reading personalized experiences of history wherein you can learn through other people’s unique experiences, and more importantly, mistakes.   1:02:25 Ryan’s writing success is owed to him taking the words of smarter people them him, re-arraigning them and repackaging them into a unique system. Does writing always have to be original?    1:05:19 What is it about daily things that is so important to Ryan?   1:10:42 The idea of looking at data that shows what artists believe is their best work and what others believe to be their best work.   1:16:11 How do you know when something is interesting?    1:20:32 How is Ryan such a prolific writer?

My guest today is Cameron Porter, an investor and former professional soccer player.  We begin the conversation talking about AlleyCorp, an investment firm in New York where Cameron is responsible for new company research and development and due diligence on seed investment. Then we move to Cameron’s experience playing professional soccer in Montreal and Kansas City, and leading the NCAA in goal scoring during his senior year at Princeton. Since Cameron is a true generalist, we explore neural networks and brainstorm ways to increase technological progress beyond the smartphone. We end the podcast with a deep and unbounded discussion about community and loneliness. In it, we explore the societal and personal impact of social media, social clubs, and the decline of religion in the West. Please enjoy my conversation with Cameron Porter.   2:19 – Idiation at Alleycorp and what is AlleyCorp? 6:17 – P-Type and S-Type Innovations 11:49 – The story of AlleyCorp 19:36 – Business Insider capitalized on being the first to use the internet to publish news during the day 26:22 – Cameron’s incredible origin story 32:05 – As Cameron’s College soccer pedigree grows he decides to go to Asia for the Summer instead of training for a potential MLS career 35:58 - After leading the country in goals Cameron is drafted by Montreal 41:52 – Cameron is traded to Kansas City after blowing out his knee but soon suffers another debilitating injury 46:12 – During your MLS time you are given the opportunity to do nothing except play soccer 52:07 – What advantages at Alleycorp do you have over large venture capitalist firms? 1:01:43 – What is something exciting happening at Alleycorp? 1:09:41 - The stagnation of innovation 1:15:43 – Emergence driven by the individual 1:20:17 – We are not pushing forward innovation with re: to the atoms of the world 1:25:38 - Kenneth Stanley’s “Greatness Can’t be Planned” vs. Peter Thiel’s “Definite Optimism” 1:33:27 – Artists and soldiers 1:42:40 - Television and Airpods have increased social isolation and our ability to avoid risk 1:51:44 – Baboons in Africa have figured out how to live better than human beings 1:59:33 – The curious case of San Sebastian 2:06:10 – Real community is a place where they miss you when you’re gone and they have a mechanism for bringing you back 2:18:37 – “Wake up excited and go to bed tired”

Emmett pioneered the Direct-to-Consumer aesthetic. The bright colors, the flat design, and the sans serif fonts are a direct result of his work. At Gin Lane, he worked with brands like Bonobos, SweetGreen, Harry’s, Smile Direct Club, and Recess. Now, he’s switching gears. Emmett and his team launched Pattern, a family of brands with products and guidance that inspire people to live a more present life.   Emmett isn’t a Luddite, but he’s skeptical of the effects of modern technology and our obsession with efficiency.     I admire Emmett’s ability to match the intuitive and the intellectual, the quantitative and the qualitative. He loves to read but doesn’t get bogged down by the dogma and precedent. He loves to be creative but isn’t trapped by the myth of the messy artist whose life is in shambles. He’s a sharp critic, a careful observer, and a prolific designer. And in this episode, Emmett reveals his true colors. But I’ll warn you, there are some curse words in this episode due to the passion of the conversation. Enjoy my conversation with Emmett Shine.

In December, I went to a live taping of the Tim Ferriss Podcast at the famous 92nd Street Y in New York City. There was a surprise guest at the event named Adam Robinson, and after hearing him speak, I tapped my friend on the shoulder and told him I’d find a way to get him on the podcast.  Adam Robinson cracked the SAT before co-founding the Princeton Review. He also wrote the only test preparation book to ever become a New York Times bestseller. He attended The Wharton School at the University of Pennsylvania as an undergrad before studying law at Oxford University in England.  He’s a rated chess master with a Life Title and as a teenager was personally mentored by Bobby Fischer—considered by many experts to be the greatest chess player of all time—as he prepared for the world championship.  Today, he applies his unique philosophy and methodology as an independent global investment advisor to the heads of some of the world's largest hedge funds.  After this conversation, I can confidently say that nobody thinks like Adam Robinson.

My guest today is Renée DiResta, who spends her time investigating the spread of malign narratives across social networks. She has advised Congress, the State Department, and policymakers in understanding and responding to the problem of misinformation. In this episode, we talk about the history of misinformation and propaganda. We go back to the roots of media theory and explore the ideas of people like Edward Bernays, Walter Lippmann, and Marshall McLuhan. I found Renée through an excellent essay called The Digital Maginot Line, which we discuss at the end of today’s podcast. I hope you enjoy this episode.

My guest today is Tren Griffin, a Senior Director at Microsoft and the man behind an excellent blog called 25IQ. Tren is one of the most prolific writers I know. He’s written books about negotiation, entrepreneurship, and Charlie Munger. He published an article every week for almost six years, and because of all that hard work, he’s now posted more than 1.3 million words online. We start the conversation by talking about his writing process. Then, we talk about distribution in the cellular business, Software-as-a-Service business models, and lessons from his legendary entrepreneur Craig McCaw. After an afternoon with Tren, I feel like he gets more excited about ideas than anybody I’ve ever met. Tren loves life, loves people, and in this conversation, you’ll see just how much he loves ideas.   SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. LINKS: Find Tren online: Twitter 25iq Other links: Bill Gurley  Benchmark Capital Craig McCaw Santa Fe Institute Patrick Collison Richard Zeckhauser Charlie Munger Ed Thorpe Lil Wayne Nassim Taleb John Malone SHOW NOTES 1:46 How did Tren get started with writing, why he is so disciplined about the writing process, and   9:44 What Tren told data scientists during his talk on complex adaptive systems, how to calibrate yourself to business cycles, and trusting the process 21:21 Acquiring judgment through seeing smart people make decisions and what Tren learned from Craig McCaw 33:25 The genesis of the software in the box business model, what the future of the book is going to look like, and the importance of curated marketplaces 41:02 The influence of the Santa Fe Institute, why distribution is so hard, and the key elements of defensibility of companies 54:03 Patrick Collison on raising the intellectual bar at Stripe, what Tren has learned from Richard Zeckhauser, and the importance of first party stories 1:05:02 Demand side economies of sale and what Tren has learn from Charlie Munger, Ed Thorpe, and Lil Wayne 1:17:48 How Tren got into hip hop, Nassim Taleb, and John Malone 1:29:53 What Tren has learned from Bill Gurley

My guest today is Mason Hartman. For years, I’ve admired Mason's perspectives on the culture, childhood, and the education system. I teach an online writing course called Write of Passage. So education –  and especially writing education – is a subject that's close to my heart. We recorded this episode in Los Angeles, where Mason works at a school for gifted children and does most of her research. In this episode, we chat about all things education early childhood development, the road to college, and why childhood has become a full time job. Then we close the episode with lessons from two of Mason's favorite people, David Deutsch and Patrick Collison. I hope you enjoy this episode. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. LINKS: Find Mason online: Twitter Other links: The Coddling of the American Mind by Jonathan Heidt and Greg Lukianoff How Schools Work by Arne Duncan   Michael Nielsen Patrick Collison David Deutsch SHOW NOTES 1:17 How to move away from the Overton window, why David’s most creative podcast guests grew up in rural environments, and why it’s important to let kids take a few bruises in a relatively safe environment 5:15 The Coddling of the American Mind, how to design schools that don’t coddle kids, and why teenage sleep deprivation leads to more accidents than drunk driving 14:05 Why standardized testing are antithetical to the underlying skills they are trying to measure, how to evaluate people when real stakes are involved, and Mason’s thoughts on the recent college admissions scandal 21:26 The binding thread that ties together Mason’s intellectual interests, how gifted kids identify each other’s strengths, and why is obsession so important to develop mastery  30:36 How obsession can equate to imagination and resilience, Masons’ thoughts on the professionalization of young kids, and the standardized expectations for kindergartners 39:44 Unbounded and bounded learning environments, how to use remixing as a way to deal with blank page syndrome, and what Mason thinks about homeschooling 52:44 What Mason thinks are the best ways to raising other’s expectations of themselves, how middle class kids are forced to pursue uncreative paths, and how exclusive colleges exploit low acceptance rates 1:01:37 The commodification of kids, the balance between rationality and intuition, and how to raise the status of obsession 1:11:47 Why you shouldn’t work on projects that you can get a grant for, how risk taking leads to progress, and what Mason learned from David Deutsch 1:23:31 Why is Mason inspired by Patrick Collison, how to ask a poignant and precise question, and why the most curious people are good at listening SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.

My guest today is Jeff Morris Jr., the Director of Revenue at Tinder. We begin this episode talking about the future of education. Jeff recently completed an MBA at UCLA and wrote his thesis on the future of Lambda School, the San Francisco based education startup. We talked about the transition from marketing funnels to marketing loops and how Tinder is growing its average revenue per user. We also explore Hollywood's transition from movies to television, and the letter Jeff received from legendary UCLA college basketball coach John Wooden. We also explore some career strategies for sparking serendipity. I hope you enjoy our conversation. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. Where to find Jeff online: Twitter Website Tinder Other links: Ryan Holdaway Lambda School K-factor by Andrew Chen  Modern Romance by Aziz Ansari RigUp Brian Nogard Show Notes: 1:18 What Jeff learned from working with Lambda school on their Outcomes team, why the incentive structure for traditional colleges is broken, and why Jeff got an MBA despite believing in the future of education looking like Lambda school? 7:43 How Jeff had to scale himself up by becoming a lot more quantitative as the Director of Revenue at Twitter, how marketing at startups has changed from funnels to loops, and the cultural power of the Tinder swipe. 12:54 How average revenue per use has come up at Tinder over the last two years, how to build a successful social product that is low in the Maslow’s hierarchy of needs, and how Tinder balances perceived coolness and utility. 18:11 The historic geographical limitations of dating, the evergreen trends in dating, and what has Jeff learned about compatibility between people through his time at Tinder 23:17 How Jeff thinks about inequality in the Tinder ecosystem, how movies and TV have set up a false idea of how people meet, and what Jeff learned about romance from film school. 30:08 The switch from Hollywood to TV for film school graduates, why TV is uniquely suited to the subscription model, and why David thinks that exporting cool is LA’s core competency 44:34 Retraining in the Lambda school era, high growth jobs that are easy to retrain for, and dynamics of proving competence and expertise 52:26 Why Jeff sent a letter to John Wooden and other celebrities, what he learned about outbound emails, and how to find the ‘underpriced assets’ when it comes to talent 1:00:55 How Jeff got a job at Zaarly ahead of hundreds of other candidates, how that experience expanded his worldview, and what you can do to set yourself apart in the job search process 1:04:47 David and Jeff give the listeners a challenge, what Jeff learned from Brian Norgard about products, and how Jeff thinks about disruption 1:17:17 The verticalization of LinkedIn and other incumbents, and why Jeff thinks being on Twitter is the reason for his high growth career SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.

My guest today is Steve Cheney, the cofounder of Estimote. Before founding Estimote, Steve was the head of business and platform at GroupMe, which was acquired by Skype. I’ve been reading Steve's writing for more than half a decade, but this year, he picked up the pace of his publishing and now I’m hooked. This episode begins with the discussion of startup dynamics. We talked about fundraising, capital efficiency, and why Steve believes that every dollar from a customer is five times more valuable than a one dollar from an investor. Then we explore the world of frontier technologies. We talked about augmented reality, self driving cars, and image recognition software. Then at the end of the episode, Steve talks about why he's been so successful writing online. Steve talks about his journey of sharing his ideas, how he started writing for Techcrunch, and why writing online is the best way to get discovered right now. This was without question, my favorite part of the episode because it ties right into my work. I teach an online course called Write of Passage where students learn to accelerate their career by writing online and by building an audience. i hope you enjoy my conversation with Steve Cheney. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. SHOW TOPICS LINKS: Find Matt online: Twitter Website Estimote Other mentions: Ben Thompson Write of Passage On How to be Discovered Knowledge and Power by George Gilder SHOW NOTES 1:53 What startups get wrong about capital efficiency, trap door decisions, and how fundraising cycles for startups work  11:35 Why Steve changed his perspective on capital efficiency, why is every dollar from a customer is five times more valuable than a one dollar from an investor, and the importance of employee retention in startups 20:09 The importance of avoiding competition for talent, why Steve’s Electrical Engineering background was very good training for startups, and the future of image recognition 33:16 Tesla and why image recognition is the next act of the internet, why frontier technologies are driven by cost curves, and the latest improvements in eyesight  43:53 The physical limits to wireless and how they are being pushed, what the future of authenticity will look like, and the defining experiences in Steve’s childhood 57:37 Steve’s core beliefs, how he has changed his views on them, and what Steve believes are his core skills 1:01:57 Why you want to work at a product-driven organization, creating something in a new area of technology, and zero sum games 1:09:40 Why Steve got back to writing online, how writing helps him learn, why writing online is the best way to get discovered 1:12:46 The switch from public to private conversations when you write online, how to crank out blog posts and get your ideas on the page, why inspiration is perishable and the importance of taking notes on things that inspire you 1:19:12 How to not get discouraged by an initial slow pace of writing, the importance of reading a lot to be a good writer, and how to become good at curation SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.  

My guest today is Matt Mullenweg, the founder and CEO of Automattic. Automattic is known for Wordpress, which powers a third of the internet. Matt and I talk about the democratization of the web, the early days of Wordpress, and how he makes sense of the incredible scale of the company. We dive into the benefits of writing online, talk about inbound vs. outbound opportunities and the open web. Then we discuss why Automattic bought Longreads, the content triangle, and the Caro books. Finally, we talk about his love for sci-fi, why writing is the ultimate long-now activity, and what’s next for Wordpress. I hope you enjoy this episode. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. SHOW TOPICS LINKS: Find Matt online: Twitter Website Automattic Other mentions: Ben Thompson Write of Passage Longreads The Content Triangle The Years of LBJ by Robert Caro SHOW NOTES 1:56 Democratizing the web, building an operating system for the open web, how Matt thinks about everything in terms of communication, and the tradeoff between powerful and intuitive 9:33 How Matt makes sense of the incredible scale of Wordpress, commodification in the age of social media, and building communities 18:57 The difference between inbound and outbound opportunities, how to reverse engineer your goals, and what Matt thinks about Ben Thompson’s Stratechery 26:26 The democratization of the means of distribution, what Matt was writing about at age 19, and the acceleration of evolution through the internet 35:23 Why Matt and Automattic bought Longreads, Robert Caro’s The Years of LBJ, and the feeling of not having anything important to say when you’re starting out 43:54 What Matt thinks about the content triangle, the good and bad ways of collaborating, and why iteration is the way to improve your writing 49:50 How a healthy comment section is like a good dinner party, why default settings are important, why Matt likes reading sci-fi, and why writing is the ultimate long-now activity SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.