As you may know, we run a podcast called upside, the first podcast finding upside outside of Silicon Valley. What you might not know is that we also listen to other podcasts.
We are not alone in believing that podcast episode discovery is broken, or at the very least not personally optimized (see Hunter Walk’s take here). Our friends at Breaker are working on solving this problem using social signaling. If you’re new to podcasting or sick of Apple Podcasts, we’d recommend checking them out, following upside, and interacting with us in the episode comments.
In listening to dozens of podcasts a week, we have stumbled across a few that really stick out. Each quarter we will distill their listens down into:
Consensus – the podcast episode Eric and Jay most agree on
Classic – Jay and Eric’s individual picks that tackle a topic near the intersection of finance and entrepreneurship
Contrary – Jay and Eric’s individual picks that aren’t immediately intuitive
So, without further adieu… the best podcasts of 2019 Q1 (according to Jay and Eric).
We think we will have to be conscious about choosing ILTB podcasts on this quarterly list because hardly a week goes by that we are not stunned by the impressive people, in-depth conversations, and intelligent questions asked on that show. In our opinion, it is the best investing podcast – and it’s not close. So, I guess it’s appropriate to start with this episode with Eugene Wei which features all of the ILTB standards – a super smart guest operating at intersections of multiple industries who can distill complex ideas into simple ideas.
Our favorite brain-nibble: “there is a mathematical measure called conversational entropy which is how predictable is the next word you’re going to type.” He relates this to the new gmail autocomplete filter where Google is exposing to all of us that we have low conversational entropy. Eugene finds that there is a correlation between high conversational entropy with interestingness as a human being. Because of this little quote, Eric has found himself almost always consciously rejecting Google’s recommendations when writing emails.
Classic
The Growers Who Focused On Creating Efficient Operations Are The Ones That Are Still Around Today
This episode is the third installment in Meb Faber’s cannabis investing mini-series and was my personal favorite. I loved the dual-prong approach of public and private markets, I love the deep insights into second layer thinking about industrial hemp, and I loved the succinct way both Emily and Morgan answered questions. More than that, this interview was incredibly timely for upside as it was released less than a week before we interviewed Periodic Edibles (UP036), a THC and CBD caramels company from Oregon.
I find this space incredibly compelling and firms like Poseidon Asset Management seem to be thinking about it in the right way by focusing on great businesses with great business models.
It’s hard to go wrong with either Ben Thompson OR Shane Parrish, and oh boy here we go we got ‘em both. I am getting more and more interested in what it means to build a niche, digital media business (with both upside and my personal writing) and to learn from two of the best was a treat.
In particular, learning about how people value subscription models, how to position your subscription model, and how to consistently create content are key components of building a niche media company.
This just may be one of my favorite podcast episodes of all time. I’m a long-time You Made It Weird listener, as it was one of the first long-form podcasts (following in the footsteps of WTF with Marc Maron).
This is nearly three hours of philosophical conversation that ranges from street performing to religion (and why Penn identifies as “atheist” instead of “agnostic” out of respect), and even how we experience reality in relation to the speed of light and sound. It’s a long, cozy conversation.
Three things stuck out to me about this podcast. First, this podcast is indicative of how good podcasts are going to get. Conan is a seasoned show business professional who asks amazing questions and has incredible control over his voice and the direction of the conversation – which he can control while seeming to not try. Most podcasters, by comparison, are amateurs. Second, the ad reads are amazing. They are everything that makes ad-reads unskippable. They aren’t standard 30-60-90 seconds. They have personality and don’t read from a script. Simply incredible. And, finally, I love the concept of two people who are always so polished kind of stepping back and showing their personalities and giving some authentic insight. No bits, no scripts. Both as a fan of the future of podcasting and as a fan of Stephen Colbert and Conan O’Brien, this podcast hit on all levels.
