North Star Podcast

My guest today is Nadia Eghbal, an independent researcher and the author of Working in Public: The Making and Maintenance of Open Source Software. She currently works on the writer experience team at Substack. She did a lot of her research at Protocol Labs where she studied the production and economics of open source. Before that, she worked on the open source team at GitHub. One of the core theses of her work is that open-source software projects don't have zero marginal cost. Maintenance can be expensive, even if the code itself is free to distribute. In this episode, we spoke about how sharing ideas on different platforms helps you express different sides of your personality, why GitHub is the center of the open source community, and what she learned running a grant program. Please enjoy my conversation with Nadia Eghbal. ____________________________ Shownotes 2:07 - Why the personal projects of a coder can unexpectedly turn into a massive public responsibility. 4:36 - The temporal nature of creating code aside from any other art form. 8:24 - How creators can become enslaved by their own systems. 12:37 - How Github differs from social media platforms, and why it might be that way on purpose. 14:54 - The similarities and differences of open source code and organized religion. 20:48 - How to efficiently externalize information to make more open source type projects possible. 24:29 - Why Nadia feels compelled to write everything down, even though to her it sometimes feels like a problem. 31:00 - How the bystander effect comes into play in the world of open source software development. 35:17 - Why Nadia believes that the way open source was started made it "set up to fail." 38:46 - The importance of granularity and modularity in maintenance, throughout people's personal and professional lives. 43:54 - What the consequences are to accepting code that causes problems downstream. 46:22 - Why Nadia chose to write and publish this book instead of going through the process of getting a PhD. 49:05 - What microgrants are, and how their different aspects play into research and development. 54:06 - How creative people can share their knowledge with each other better through story sharing. 57:28 - How Nadia focuses the scope of her projects from being too overly broad. 1:00:40 - The danger of thinking you ever know enough about any field that's not your own.

My guest today is Matthew Kobach, the Director of Content Marketing at Fast and the former Manager of Digital and Social Media at the New York Stock Exchange. Matthew and I met on Twitter, where he shares actionable strategies for building brands on Twitter, Instagram, and Facebook, and YouTube. He does it with a level of humor and honesty I’ve never seen in the social media industry. This episode is a deep dive into Matt’s philosophy of social media. We started by talking about his all-time favorite television commercials and how they inform his social media strategy today. Then we spoke about how paid and organic social media should influence each other and why Cash App’s cash giveaways are such a smart social media strategy. Please enjoy my conversation with Matthew Kobach. ____________________________ Show Notes 1:39 - Who has surprised Matthew the most with the success of their social media strategy. 4:22 - Why social media is undervalued by the majority of marketing agencies. 8:32 - Why marketing to the "wrong" audience is still effective advertising. 13:08 - Matthew's favorite TV commercial of all time and why remembering the product may not be super important. 19:39 - How good advertising realizes things about yourself you haven't yet discovered. 24:03 - What social media post has been most successful for Matthew. 29:37 - How Matthew leveraged social media to land his current marketing job. 35:49 - Why focusing on organic long-term social media marketing instead of short-term paid became Matthew's niche. 39:07 - The convergence of organic and paid advertising and why Matthew thinks it's so effective. 45:10 - How having a long time horizon on your marketing strategy can help increase organic growth. 49:40 - Why giveaways have been and will always be successful. 54:49 - The greatest marketing lesson Matthew learned from his dad. 56:53 - Matthew's greatest takeaways from Peter Thiel's "From Zero To One." 59:09 - Why a fundamental change of social media seems completely unlikely without one particular element. 1:02:34 - How writing has become Matthew's "one weird trick" as a social media marketer. 1:06:20 - Why Matthew believes that at the opposite of a good idea is another good idea and why the inverse is also true.

David Brittain is the CEO of Concepts, my favorite iPad app. It's marketed as a "flexible sketching" app and geared towards people in the early stages of the thinking process. I use it to visualize my ideas, many of which I share on Twitter and in long-form essays. People use the app for mind-maps, mood boards, sketch plans, designs, and illustrations. I particularly enjoy the screenshots of architects using the app to design buildings. On this episode, David and I talked about the business, marketing, and engineering aspects of designing an app. David talked about Concepts' position in the design world, and how it compares to ProCreate and Figma. He spoke about how changes to the App Store have influenced Concept's download numbers and finally, he talked about why trust is particularly important in remote work as compared to in-person collaboration. I'm a fan-boy of the Internet because of how it enables apps like this to thrive. Concepts has been profitable for years. Whenever I pick up the app, I feel like I have a professional-grade design app for the cost of a latte every month. Please enjoy my conversation with David Britton. ____________________________ Show Notes 2:20 - How the landscape of designing apps has and hasn't changed drastically over the years 4:19 - What and who David thinks about in his design process 7:32 - How remote work management is different from in-person 11:52 - The key to a well-functioning and efficient remote engineering team 13:26 - How David spends his days at work as a CEO 16:36 - What vector design is and their pros and cons in comparison to raster design 21:20 - David's view of the market, the design world, and his competition 24:34 - How Formula 1 driver Lewis Hamilton has inspired David and what he could learn from Lewis about marketing 27:37 - Why paid marketing is not something that David and his team have spent much time nor effort on 32:08 - What David sees as the biggest pain-points from a user perspective of his app and the solutions they've tried 35:46 - What makes a good beta tester or user to get feedback from, and David finds them 37:47 - Why David doesn't consider himself the right person for his position and why that has been an advantage for his company 40:05 - The death of the computer mouse and why sketching and drawing isn't going anywhere 44:48 - How the Concepts team approached the development of their app on different platforms 46:43 - The future of apps and why certain apps have taken off while others lag behind 53:13 - How a feature moves from an idea into development and into the hands of the end-user 56:54 - Why architects flocked to using Concepts when it came out and what makes it still popular today

  Tyler Cowen is an economics professor at George Mason University. He runs the Mercatus Center, which bridges the gap between academic ideas and real-world problems. He’s published a new post every day for the past 17 years on his blog called Marginal Revolution, where he writes about economics, arts, culture, food, and globalization. Beyond that, he also writes for Bloomberg and hosts his own podcast called Conversations with Tyler. Tyler ends every episode of his podcast asking about other people’s production function. How do you get so much done? What’s the secret sauce of all that you’ve accomplished? This episode is entirely devoted to that question. But this time, I’m asking Tyler. We started by talking about why there aren’t more Tyler Cowens in the world. Then, we moved to Tyler’s process for writing, such as choosing article topics and editing his work. Later in the podcast, we discussed Tyler’s process for choosing friends, why he would travel across the world to visit a new country for just ten hours, and what he’s learned from high-powered people like Peter Thiel and Patrick Collison.   ____________________________ Show Notes 2:40 - What Tyler considers his compounding advantage and where he got it from 5:56 - Why being born as an intelligent person is not as important as developing knowledge 8:23 - How Tyler maximizes the value of his consumption and minimizes the drawbacks 9:19 - What draws Tyler to the people he likes spending time with, and what he likes best about their friendship 12:33 - Why Tyler feels that the way he has lived his life has meant has not given anything up 15:35 - How the fundamentals of productivity came intuitively to Tyler 17:41 - Why Tyler writes in his particular style not by choice, but by necessity 22:19 - Why the things in Tyler's life that bind his output aren't what you think 24:06 - How to develop new ideas while staying focused on the subject and not getting tangled 27:36 - Why Tyler sees art as one of the most important and beneficial things you can spend your time and money on 32:41 - What writers can learn about inspiration and consistency from musicians and visual artists 37:16 - Why Peter Thiel has impacted Tyler so deeply and why Tyler believes he's one of the greatest thinkers of our time 40:30 - How Tyler is able to extract more from his reading than other people do 45:44 - How understanding most other people's intelligence is higher than his in most fields gave Tyler an edge over other thinkers 49:00 - Why Tyler sees a new visibility of talent in people and how he is using this visibility 55:24 - How Tyler constructs his interviews to maximize the freedom of his guests to speak freely on what they love 1:00:03 - How to develop skills as a teacher and where Tyler believes the strengths of a good teacher lie 1:03:34 - Why the novelty and beauty of visiting other cultures excites Tyler so much 1:07:18 - How Tyler makes the most out of his travels 1:13:32 - Why sitting in a suboptimal seat at a concert may give you worse sound but a better understanding of the music 1:16:55 - Why knowledge workers are often not motivated to improve their skills 1:20:48 - Why Tyler still responds to every email and loves it

My guest today is marketer and software engineer Patrick McKenzie, who writes mostly about software-as-a-service businesses. He currently works for Stripe as a writer and an overall software business expert. I remember when I signed up for Stripe's Atlas program to incorporate my LLC, almost all of the documentation that wasn't legal documentation was written by Patrick. Patrick has also started multiple software businesses such as a bingo card creator for teachers, an automated appointment system that sent automated reminders to clients, a gaming company for teaching programming called Starfighter, and a software consultancy called Kalezumeus Software. I have devoured Patrick's work. He is one of my favorite online writers. Before we begin, here's my attempt to summarize what I've learned from him in three sentences. First, charge more for your services and products. Second, the economy is much bigger than you thing. Three, create for unique people, not average ones. ____________________________ Show Notes 3:07- What surprised Patrick about writing online. Why writing online takes you from someone who is illegible to someone who is legible. Why blogging has a lower value for business people. 13:40- The benefits of owned platforms vs self-published. What people are missing about writing long-form. How to make the illegible structures legible in your online audience. 24:18- Where all the great bloggers went. Patrick's writing process. Why you should grow an email list. 36:43- How to identify which ideas are worth publishing. How care for the craft has influenced Stripe's culture. 46:55- What writing regularly does for a company. Why write the book before the software. 1:00:01 How "Patio11's law" explains the amount and wealth of niche software companies. How to develop a love for your craft. 1:12:36 How to increase your optimism and ambition. Why self-promotion is like cooking.

My guest today is Will Mannon, the student manager for my online writing school called Write of Passage. 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. This conversation is a deep-dive into our work together. We start by talking about the difference between Type 1 and Type 2 online courses. Then, we move towards psychological topics like how to hold students accountable to helping them navigate the fear of publishing online. Please enjoy this window into Write of Passage and the future of online learning.    _____________________________________ Show Notes 1:50- David and Will’s focus on customer happiness. Type one and type two online courses. What online educators can learn from the Navy Seals. 13:45- How fear is a part of transformational experiences. What held Will back from starting writing. What music can teach us about great writing. 19:27- Why we fear achieving our vision. Write of Passage guilt. How Write of Passage prioritizes helping people make friends.  27:23- Striking the balance between creating community and letting it grow naturally. How interest groups allow students to create their own communities. The structure of Will’s job as course manager. 35:58- Forte Lab’s yearly planning process. The three phases of Will’s course management. How Will and David are thinking about data collection. 49:14- How Will and David met. How Will’s course feedback led to working with David. Why classical education theory doesn’t really apply to online education. 59:11- Why Will and David create “type 2” courses. Why David learns from his students. How Write of Passages integrates feedback. 1:07:20- What feedback David listens to. The future of Write of Passage. Why David tries to solve very specific problems using software. 1:12:10- How the Internet makes attention a commodity. Why WOP can thrive with zero cold traffic marketing. How the Internet will help make creators money in the future.

My guest today is Sara Dietschy, a YouTuber with more than 620,000 YouTube subscribers. This is the fourth interview I’ve recorded with her. It’s her second appearance on the North Star Podcast, and I’ve been interviewed twice on her podcast called That Creative Life.  Sara makes a couple of videos every week focused on creativity, technology, and entrepreneurship. Most of her revenue comes from paid partnerships, and she’s teamed up with brands like Intel, AT&T, Visa, Squarespace, and BestBuy, and Adobe.  This episode begins with a discussion of what it means to be a YouTuber, so Sara shares lessons about hiring and monetizing a channel. Then, she talks about her creative process with ideas like her “one for them, one for me” model of creating content. We also talk about the future of influencer culture, homeschooling, the Despacito music video, and what we’ve learned about delegation. ___________________________________________ Links to Sara: Sara’s Youtube Channel Sara’s Website   Other Links: Linus Tech Tips Paul Graham’s Maker Schedule, Manager Schedule David’s Obsession Tweet Eric Weinstein- What Should We Be Worried About Epidemic Sound ___________________________________________ SHOW NOTES: 2:02- This isolation of creative hiring. What it means to be a YouTuber. How Sara learns about new technologies. 12:36- What Sara is most opinionated about. How quantification affects Sara’s creative process. 19:30- How Sara creates her content using the “one for me, one for them” model. David and Sara’s creative process. Sara’s relationship to Twitter and YouTube. The future of influencer culture.   31:01- What is good and bad about obsessive personalities. The future of public school and the positives and negatives of homeschooling. The difference between excellence and genius and how school only trains for excellence.  48:02 The gift of truly hating something. The art of video editing and what makes it difficult to delegate. How YouTube has changed over the past ten years. 1:00:55- What Epidemic Sound is doing well. Why Despacito was so popular on YouTube.  1:06:17- Who has done well with delegation. What is so difficult about hiring for creative roles. Why Sara hired a meme creator. 1:18:42- Why differentiation is free marketing on the Internet. Love languages for hiring. David and Sara’s brand dissection podcast plan.  

I have two guests this week: Austin Rief and Alex Lieberman, the founders of Morning Brew. Their business-focused daily email newsletter now has more than 2 million readers. These two gentlemen started the company in college while studying at the University of Michigan. It began as a simple idea — to make business news more interesting for young people. While helping his college classmates prepare for job interviews, Alex noticed they failed to connect with traditional business news. They wanted something better to keep them informed, so he created a daily newsletter that later became Morning Brew.  I will never forget the first time we met. We were introduced by a mutual friend and agreed to coffee at the Beekman Hotel in New York City. We spoke for two-hours about the future of media, then raced to Morning Brew headquarters where we immediately wrote an article called The Pivot to Owned Commerce. One year later, Austin and I recorded a podcast about the secrets of email marketing and the story of Morning Brew.  In this episode, we spoke about the benefits of showing how you run your company, what a Cross-Fit-for-Writing community could look like, and Morning Brew’s secret sauce for hiring writers. Please enjoy my conversation with Austin Rief and Alex Lieberman.  Links: Morning Brew Business Casual Podcast Austin's Twitter Alex's Linkedin

My guest today is Tiago Forte. He runs an online course called Building a Second Brain, which I took in August of 2017. I went from being overwhelmed by information to being in control of it. My writer’s block disappeared and my productivity skyrocketed. Tiago changed the way I thought about work and my relationship with information. Fast forward to today, and Tiago and I are business partners. He helped me create my online writing course, Write of Passage and together, we’re building the infrastructure required to scale an online education business. Tiago is one of my closest friends and the person who shaped my career more than anybody else. In what’s becoming a tradition, Tiago and I used this podcast to reflect on our work together. First, we talked about what we’ve learned about email marketing. Then, we moved onto ideas like leadership, working in small packets, and personal growth. Please enjoy this window into our work and friendship. __________________________________ Links: ConvertKit MindValley  Great Assistant No code  Things  The Decadent Society  David Allen- Getting Things Done  Venkatesh Rao  Teachable  Tyler Cowen- Emergent Ventures  ________________________________________ SHOWNOTES 1:54 Being a Citizen of the Internet. The role that ConvertKit provides for Tiago’s team. How thinking systematically changes how we work for the better. 14:05 The difference between training and teaching through SOP’s. Why David and Tiago hired expensive personal assistants. Why David and Tiago have the goal of only doing something once before finding an automation solution.  27:07 What David and Tiago have learned about running online courses. How online teaching has changed since Tiago and David began their school. What role entertainment and community have in the structure of their courses. 35:05 The dangers of only formulating for ease. The psychology of pricing. The benefits of small, self-motivated teams when you work remotely. 45:05 How “reusable packets” are the backbone of David and Tiago’s work. The “lego block” technique of creating content. How Tiago orients using objects, not humans as linchpins in his business. How David writes first and researches second.  56:33 How the “beginner’s mind” aids David and Tiago write well. How David takes 5 observations a day to create deep and insightful content.  1:04:00 Why books are a mark of legitimacy. The illogicality of fashion. Why publishers want a sure bet. 01:11:40 The next chapter of online education. How scarcity can make time important again. Tiago’s theory about how you to be your full self online now. How instinct works online. 1:23:40 The hero’s journey of sharing your authentic self online. How Tyler Cowen’s mentorship changed David’s life. How Venkatesh Rao changed Tiago’s life. 1:33:22 The shift from interchangeable courses to interesting and specific courses. Why Forte labs is creator-focused, not curriculum-focused. Why building a business is an act of discovery at Forte Labs. 1:42:16 Why David and Tiago are looking for people who have vision combined with passion. Why innovation is directly related to intuition. How to learn faster. 1:53:43 How growth is paying attention to what you are not capable of doing. The skill of knowing the difference between a challenging situation and a fundamentally incompatible one. How the internet can help people create their own definition of success.

My guest today is Michael Mayer, the co-founder and CEO of Bottomless. This episode explores business from a variety of angles. Michael talks about how he thinks about marketing at bottomless, and the accumulating advantages that drive the company. He also talks about what he learned at YCombinator, why startups that move fast have such an advantage, and how to think about execution in a fast-growing company. Five years ago, Michael was a dish washer. Then he worked at Nike before receiving funding from YCombinator and starting Bottomless. Please enjoy my conversation with Michael Mayer. _____________________________________ Links Bottomless https://www.bottomless.com/ Lateral Thinking with Withered Technology https://en.wikipedia.org/wiki/Gunpei_Yokoi#Lateral_Thinking_with_Withered_Technology Y Combinator https://www.ycombinator.com/ Paul Graham http://www.paulgraham.com/ Satoshi Nakamoto’s Bitcoin Whitepaper https://bitcoin.org/bitcoin.pdf Sam Altman- https://blog.samaltman.com/ Wyden and Kennedy https://www.wk.com/ David Ogilvy https://en.wikipedia.org/wiki/David_Ogilvy_(businessman _____________________________________ Show Notes 2:05 The inspiration behind Bottomless. How Michael reformulated coffee supply and demand as an information problem.  How advances in computing and the internet are really advances in legibility. 08:18 The original vision Michael brought to Y Combinator. Bottomless’ marketing plan. Why to buy fresh coffee and grind yourself. 15:50- How Michael’s tech and coffee journey are connected. How to find luxury in inexpensive packages. How many luxuries are just resource intensive. 22:23- What surprised Michael about working with Y Combinator. How the thinking needed in a company gets baked in with the first vector, but extreme execution is what makes success. 26:57- How execution informs Michael’s strategy. Why Bottomless and David strategize on Sunday and execute the rest of the week. How making more decisions more quickly is better than making perfect decisions slowly. 30:30 Michael’s 10-minute interview to get into Y Combinator. When to think, and when to act in your business. Why mistakes are penalized in school, but some of the best things that can happen in life. 37:09 Why to write pseudonymously. What Michael has learned from Paul Graham. Why Bottomless has outsourced a lot of marketing recently. Michael’s experience watching product development while working at Nike. 46:35 Why Michael believes the best people to be doing product development are also doing the operations and customer support. Why status and hierarchy get in the way of running a good business. Why market research should be satisfied by your customer service.