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. 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.

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.

My guest today is Sara Dietschy, a YouTuber with more than 620,000 YouTube subscribers. This is 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. 

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. 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...

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. 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.

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 Y Combinator, 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 Y Combinator and starting Bottomless.

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. 

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.

Today’s guest is Alex Danco, one of my favorite writers in the world. 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.

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.

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. 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 his method of finding new artists, to the economics of concerts and music festivals. I hope you enjoy this...

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. 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.

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. We spoke about high vs. low trust societies, the difference between writing styles in New York and San Francisco, and how the Internet is raising the value of being a good photographer.

My guest today is Tiago Forte, who runs an online course called Building a Second Brain. 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.

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. Please enjoy my conversation with Ryan Holiday.

My guest today is Cameron Porter, an investor and former professional soccer player.  We begin the conversation talking about AliCorp, an investment firm in New York where Cameron is responsible for new company research and development and due diligence on seed investment. We end the podcast by exploring 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.

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...

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...

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...

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.

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.

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.

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.