This week, to mark the two-year anniversary of the podcast, I offer a quick summary looking back and forward. Yesterday I heard about an Appalachian Trail thru-hiker named Croatoan, or Crow for short. Crow was his trail name, which all A.T. thru-hikers carry. Importantly, you can’t give yourself a trail name. Someone else has to…

I intentionally avoid the world of quantitative investing on this podcast. The whole point of this format is to learn about many different fields, and the vast majority of my time is already spent in quant world. Occasionally I’ve broken this rule because of something unique, including this week’s conversation with Richard Craib, the founder…

My guest this week has a fascinating background. He has a PhD in biology but has split his time as both an investor and an operator. As an investor, he’s involved in companies like Airbnb, Coinbase, Instacart, Opendoor, Stripe, Square, and Pinterest—not too shabby. As an operator, he helped both Google and Twitter scale their…

Show Notes 0:00 – (First Question) – How does he think about optimizing risk in terms of the capital stack when looking at deals 3:25 – What conditions would they add debt down the road after investing in a company 4:50 – What business sectors are most intriguing for Morgan to invest in right now…

An interesting question that I think about a lot: how do you balance exploring the new with savoring what you already know and love? Most of the time I prefer to explore, but the best part of this podcast experience for me has been meeting people who become close friends. For episodes 99 and 100,…

This week’s conversation is for those interested in the nitty gritty of cryptocurrencies and for those who, like me, are fascinated by that world but more than a bit skeptical of the investing prospects for the many cryptocurrencies now in existence. My guest is Ryan Selkis, who I met at an event hosted by Union…

My guest this week is Cathie Wood, the founder of ARK invest. Cathie and her team believe that disruptive innovation is the key to long-term growth and, therefore, alpha in the public markets. Because their style of investing is entirely contingent on what will happen and change in the future, it is about as different…

I’ve often heard that good investors are a bit like journalists: doggedly collecting evidence and building an understanding of how all the pieces of a company or investment fit together. My guest this week is one of my favorite writers and journalists, Bethany McLean. Across her career, Bethany has covered many of the most interesting…

A very short introduction today because my guest is anonymous. Suffice it to say he manages a large pool of private capital. He goes by the pseudonym “modest proposal” and his Twitter presence is one of the reasons I first got on and now stay on the platform. He is level-headed, smart, and skeptical by…

This week’s episode covers a new set of topics. The conversation, with Niel Robertson, covers media, e-sports, content distribution, marketing, and a lot more. Niel started a software company out of his bedroom when he was 14, and sold his first company in 1999 for $280 million, when he was 24 years old. He has…