North Star Podcast

My guest today is Matt Cooper, the CEO of Skillshare — a subscription-based online learning platform where people can take classes on-demand. The main categories are creative arts, design, entrepreneurship, lifestyle, and technology. Before joining Skillshare, Matt was the CEO of Visually, an online marketing place for creative work. And before that, he was the VP of Operations for oDesk, the world’s largest marketplace for online work now known as UpWork.  Matt and I spoke about the future of education, online and offline. We discussed different business models for online creators, such as Skillshare’s subscription model and the a-la-carte model that I use with Write of Passage. We also talk about what it takes to be successful running an online course, from creating a curriculum to entertaining your students to building an online audience. Please enjoy my conversation with Matt Cooper. ———— 1:55- Skillshare’s model of education. The accessibility of a subscription model. How Skillshare uses behavior to build their algorithms. 11:11- Skillshare's success and failures moving into business education. The benefits of using Skillshare for teachers. Skillshare's revenue model and why they are leaning towards shorter lessons. 15:08-How teachers should tailor their courses for online learning. The production style and schedule of a Skillshare Original class. Why the best teachers are not always the best experts.  22:17 How teachers should consider personality when creating their online materials. Matt's career creating businesses that help freelancers- from unemployment to Skillshare. Why the human element drives Matt's business sense. 30:04- What Matt loves about the open marketplace model. Supply and demand in open market learning. International pricing as an opportunity to build markets. How bundling may be the future of growing certain international markets. 40:28- Matt's experience with education and why there are so many companies based in Plano, TX. Why Skillshare is the new community college. What Matt would do if he was the president of an Ivy League School. Matt's vision for a more efficient model of higher education.  51:30- The value and the cost of a liberal arts education. 59:46- How remote work can both change the quality of life of employees and give companies access to talent they aren't competing with locals for. Why David and Matt bike in New York. Tik tok and the future of production.  1:07:40- Why completion rate is not the most important metric for Skillshare. The challenge of determining user intent. Who is doing the best on search and browse. How Skillshare manages feedback and the social aspects of learning.

My guest today is Hollywood actress, producer and director Jennifer Morrison. She’s known for her roles as Dr. Allison Cameron in the medical-drama series House and Emma Swan in an adventure-fantasy series called Once Upon a Time. She also appeared in movies like Star Trek and TV shows like This is Us and How I Met Your Mother.  We got connected through a workshop I hosted called “How to Crush it on Twitter,” which is exactly the kind of wonderful serendipity I talk about when I talk about why you should share your ideas online. We begin this conversation talking about Jennifer’s time playing clarinet in a marching band. Then, we spoke about how she finds inspiration for stories, chooses what to work on, and how she takes on the role of a character. But the best part comes at the end when we talk about imagination and a movie called “Field of Dreams." Please enjoy my conversation with Jennifer Morrison.  ———— Shownotes 1:36- How Jennifer Morrison began playing clarinet and what separates a world-class marching band from a mediocre one. How Jennifer uses a coach to hone her craft. How Jennifer keeps focus in the high-distraction environment of a live shoot. 13:25- Why Jennifer’s bottom line for judging an acting performance is “do I believe you” and “do I care about you?” How directing has changed Jennifer’s acting. How trust, research, and imagination are Jennifer’s keys to great performance. 25:25- Why Jennifer asks, “what is the ecosystem I am about to join” before signing on a project. How conflict can drive creativity. Posturing versus collaborative problem-solving in Hollywood.  35:15- The cogs of the Hollywood “machine,” and the huge financial bet a studio makes when they hire a new actor. Jennifer’s take on the downsides of celebrity, and the baffling art of being “known for being known.” 48:30- Why coming home after being present with thousands of people is one of the most dangerous moments for an actor. How Jennifer reestablishes her own identity after working. How digital streaming and the internet are like quantum physics. 58:35- How Jennifer and David navigate growing and evolving as individuals while having a backlog of performances and writing available to the public. How Jennifer deals with uncertainty and criticism while still moving forward as an actor. 1:08:12- How reestablishing trust in the world will come from individuals reconnecting to their own truth rather than from the media. Why Jennifer only works on projects that she feels strongly driven to.  2:13:27- How Jennifer thinks the current COVID-19 crisis might influence international film making and consumption.  2:18:25- Why Jennifer thinks that Field of Dreams is a perfect movie.

Today’s guest is Alex Danco, one of my favorite writers in the world. Back when I was in college and before I started writing, Alex was one of the first people who made me say “Wow I want to write like this for a living.” For years, he worked on the Discover team at Social Capital where he wrote a weekly newsletter called Snippets. Now, he’s joining the Shopify Money team, where he’s building the future of financing merchants and entrepreneurs with everything they do. This episode begins with a conversation about a book called Technological Revolutions and Financial Capital. It’s a favorite of investors like Fred Wilson and Marc Andreessen and Alex breaks it all down for us. Then, we talk about cities and the growth of suburbs in North America. And finally, we talk about the mechanics of writing online. ____________________________ Shownotes 2:10- How Alex found Carlotta Perez and her book Technological Revolutions and Financial Capital through the work of Bill Janeway. Why, if you are creating an unknown truly new product, you cannot know the value of your equity. How the venture capital community uses tested milestones to show potential value to investors. 10:20- An overview of the two main ways that risky business ventures were funded before VC. How financial capital and production capital exist fundamentally in tension with each other. Carlotta Perez’s theory on the life cycle of financial bubbles. 17:15- Is entrepreneurship across the US growing or shrinking today? Why the current VC and tech industry is a great example of "we shape our tools and then they shape us." Why founders are increasingly interested in funding that prioritizes optionality. 27:00- Why venture capital values opposite indicators of success than the general economy. Why so much education for innovators is focused on venture capitalism. Why Alex believes that financial Twitter will help fill the role of intellectual stimulation for people managing boring businesses.  34:30- Why Alex writes 5,000 words a week. How writing in public can help in ways that just thinking does not.  39:10- How to find "the villain" in your writing. How Alex believes urbanization and intellectual migration to cities will change in the US in the future. Jane Jacobs and the idea of complete communities versus gentrification. 48:18- Why complete communities are now found in the suburbs. The growing pains of Toronto. Why so many world-class musicians have come out of Toronto. How do highways create local culture? 59:10- What the organic, long-lived nature of cities means for how they change. How autonomous vehicles will change cities. How the pricing power and efficiency of large companies distorts the true cost of shipping, healthcare, and education. 1:08:10- How audio changes our brains. How the feed-forward system works in our sensory perception and motor function. Alex explains Claude Shannon's information theory and Marshal McLuhan quote "the medium is the message." 1:21:42- Why audio is the most information-heavy medium. Why great writing is not written the way that the author speaks. How Alex interprets the classic Nixon/Kennedy debate story.  1:27:22- What the rise of podcasts means for media consumption and mental processing in the US. Why Donald Trump thrives in an audio environment.  1:32:07- How Alex uses summarizing to improve his writing. How publishing every week informs Alex's content. Why the background information in your writing is some of the most important material in your post. 1:37:14 How Alex crafted his piece Social Status in Silicon Valley. How to create new ideas and work using an anchor in what you know.

My guest today is Ryan Singer, the head of Project Strategy at Basecamp. Ryan recently published a book called Shape Up where he describes his process for planning, designing, and executing projects at Basecamp. In this interview, instead of talking about Shape Up and the principles in the book directly, we danced around those topics and applied them to ideas like consciousness, architecture, and product management. We talked about the interaction between design and consciousness and how Ryan’s love of architecture lead him to Christopher Alexander. We talk about relationships between top-down and bottom-up perspectives on the world and how you can synthesize the two. Our conversation begins by applying Shape Up to the writing process. At times this conversation is practical and at times it gets spiritual. ____________________________ Shownotes 2:02- How Ryan used the core principles of Shape Up to structure, focus, and ultimately write his book, using workshops to refine how you present your ideas and the necessity of using time constraints and process clarification to move through the different processes of writing. 8:29- Ryan’s transition from being a designer to a designing programmer and the successful elements of teamwork that Ryan has identified over his 16 years at Basecamp. 15:13- How impact and team satisfaction drives productivity and focus for Ryan’s team and how the 6-week schedule at Basecamp facilitates this satisfaction. The balance you can find by asking, “How far can you push in one push?” 19:57- How enthusiasm paired with timeboxing helps a team feel energetic but still healthy, the nuance of using a firm 6-week time boundary for a project, and how hard walls with a soft middle are key to the Shape Up method.  26:44- How a team can be committed to the end goal without being attached to how to get there, why Ryan uses the deeply matured truth of architecture to inform his work in the newer field of interaction design and his appreciation of Christopher Alexander’s design principles. 35:18- How only a deep understanding of a problem can inform the comparison methods for the potential solutions, the multiscale principle as relates to Modernist buildings and design, and the playout of human scale and architecture in Minecraft and tourist destinations. Ryan asks the question, “how do we specify the large scale and allow the people living there to design the small scale?” 49:44- Why Ryan chose “Felt Presence” as the name of his website, how consciousness and the mind inform Ryan’s design work, how Bob Moesta’s work to understand why people reach for a Snickers bar informed a redesign of the candy. 55:52- How understanding the underlying causes of a situation can help you design a useful solution.

My guest today is software engineer, designer, and researcher Andy Matuschak. He’s focused on Tools for Thought — which is a fancy way of saying that he works on technologies that expand what people can think and do. Before working as a researcher, he helped build iOS at Apple, focusing on foundations like multitouch, animation, and inter-app coordination. Then, he worked at Khan Academy where he led and co-founded the Research & Development group. In this conversation, we talk about the structure of online education, how to take notes, strategies for developing new ideas over time, secrets of creative partnerships, and what it means to do creative work. This conversation begins with a discussion of my online writing course, Write of Passage. I hope you enjoy this conversation.

My guest today is Chris Zarou, the CEO of Visionary Music Group and the behind-the-scenes mastermind behind the success of Logic and Jon Bellion. I’ve been a fan of both his artists since my early days of college, so I’ve watched them both blow up with my own eyes. The episode begins with Chris’ time playing Division 1 soccer before transitioning to artist management. From there, he talks about how he met Logic and what he’s learned from Jon Bellion about the creative process. And finally, we dive into all facets of the Hip-Hop industry from his method of finding new artists, to the economics of concerts and music festivals. I hope you enjoy this episode.

My guest today is Robert Cottrell, the founder of The Browser, which has become my go-to source for articles. Here’s how it works. Every day, he recommends five articles and includes a short summary for each one. They’re wild and random — but that’s what makes his work so exciting. For example, today’s issue has an articles about how bees argue, the battle of ideas in China, how Americans should think about nuclear weapons, the circus arts, and the future of machine-created art. In this episode, we talk about why journalism is one of the most under-valued crafts in the world, what we should know about Latvia, and the cutting edge of language translation software. Please enjoy my conversation with Robert Cottrell. 

My guest today is Andy McCune, an entrepreneur and creative who co-founded Unfold, a mobile design tool kit for storytellers that was acquired by Squarespace. He also runs an Instagram account called Earth (@earth on Instagram) with 1.1 million followers. Andy is one of the very most talented people I know. And he has a more intuitive, make-it-and-test-it way of working than most of the people on this podcast. I’ve built a friendship with him as he’s flown under the radar for years. I remember talking to Andy about Unfold back when it was just a small side project, and it’s been a joy to watch Andy grow and scale the business. Please enjoy my conversation with Andy McCune.

My guest today is Samo Burja, the founder of Bismarck Analysis, a firm that analyzes institutions, governments, and companies for high net worth individuals. Samo is known for an idea called Great Founder Theory, and his research focuses on the causes of societal decay and flourishing.    This is my second time having Samo on the podcast. In this episode, we spoke about high vs. low trust societies, the difference between writing styles in New York and San Francisco, the economics of building an online audience, and how the Internet is raising the value of being a good photographer. But first, we begin talking about how-to videos on YouTube, and their influence on culture. I hope you enjoy this episode.

My guest today is Tiago Forte, who runs an online course called Building a Second Brain.   This episode is different than most of my podcasts. It’s less of an interview and more of a conversation.   Tiago and I have collaborated closely for the past year. In February, we worked together to film and produce my online writing course called Write of Passage. And throughout the year, we’ve teamed up to improve every aspect of the student experience.   We recorded this episode from Arizona where we were hosting our Creative Process Workshop, which offers a radical new approach to writing in the Information Age, just like Write of Passage.    In this conversation, we reflect on the time we’ve spent working together, explore the key trends in online education, and talk about what we’ve learned by teaching more than 1,000 students combined.   Please enjoy my conversation with Tiago Forte.     -- --    2:15 – the shifting bottleneck of online education   10:53 – discovering how much our own identities/how we perceive ourselves impact our actions   13:30 – changing identity on scale through online schooling   25:04 – the audio revolution and returning to Marshall McLuhan   28:20 – origin story of Write of Passage   35:23 – how feedback loops exponentially increases your output   41:50 – it’s easier than ever to create, so what has gotten harder   48:20 – the evolution of note taking   54:38 – C.R.I.B.S.   58:55 – to create takes courage OR the internet just magnifies humanity   1:04:49 – if you can easily describe what you are doing it’s probably not ambitious enough   1:13:05 – everything is “figureoutable”   1:19:20 – reaching quality through quantity   1:28:19 – Michigan and Ford factory visit   1:35:41 – the power of a weakness   1:41:40 – you cannot change your own identity without growth   1:44:52 – importance of constraints   1:50:40 – what’s the experience of playing with constraints and an example of an outcome?   1:56:32 – writing as thinking and re-writing as re-thinking   2:00:52 – “freedom to make a bad painting”   2:04:32 – the paradox of specificity: the more specific what you are known for is, the more opportunities you’ll attract