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Best Entrepreneur Podcasts of 2019

By 2020-01-12 April 20th, 2020 No Comments

I listen to hundreds of podcast episodes every year, possibly thousands. These are some of the episodes I found interesting enough to listen to more than once in 2019.

Interestingly, I’m drawn more towards people and how they think, rather than particular topics. So once I find somebody who changes my thinking, I look for other podcast appearances they’ve done. It’s a great way to discover great new podcasts.

Eugene Wei on ILTB and North Star. Love Eugene’s ideas around status (as a service), proof of work, and entropy. Also learned how filmmakers setup the zolly shot (I had always wondered).

The North Star Podcast has tons of great guest episodes, like Keith Rabois and Daniel Gross. The host, David Perell is also a great and prolific writer (we featured his What the Hell is Going On essay in issue 33 of Hackerpreneur Magazine). I’d been waiting to see what the best of the new digital native generation would look like. And it looks something like David.

Venture stories is a real-time lens on Erik Torenberg figuring stuff out through interesting conversations. The Sovereign Individual features a lot in his thinking – it’s a staggeringly prescient book and it’s interesting to see Erik talk through its contexts on the podcast. Probably my goto podcast if 2019 but the standout episode for me was Joel Monegro on Crypto Networks and Investing in Crypto. Particularly curious about distributed vs centralised, the way Joel defines capital, and what we currently use for the three jobs of money.

Patrick Collison on the Farnam Street podcast. Paul Graham described Patrick and his brother/co-founder, John as “theoretical physics smart, Napoleon ambitious, and brother tight.” This conversation with Shane Parish shines a light on Patrick’s beautiful first-principles thinking.

Naval is another one of those thinkers who has managed to tease out a simple yet dense world view from the complex chaos and articulate it in a distilled, lucid and intriguing way. His own podcast episode on wealth creation (How to get rich without getting lucky) is 3+ hours of wisdom and the clearest example of how he thinks. I also enjoyed his first appearance with Tim Ferriss (2015) and this episode of After On.

Now that I mention it, that episode was a gateway into the After On podcast which has many great episodes and guests, like Don Hofman’s case against reality.

I’ve been delving more recently into money and wealth and the John Parise episode of the Meb Faber Show stood out. Basically how ultrarich families ($10-100 million) protect their generational wealth through efficient tax planning and trust funds. I think I found Meb through the Jason Calacanis episode, which is also worth a listen. Jason’s This week in Startups showcases founders and it’s probably the best pure entrepreneur podcast out there.

The Drive by Peter Attia is my go-to for keeping up with my past life as a biologist. It’s difficult to pick a standout episode but his (non-science) conversation with Tom Bilyeu was surprisingly good.

Dan Carlin’s Hardcore History is the astounding unscripted story of how we got here. The punchline… the intrinsic nature of violence has been the most foundational force in our history. Makes me think that we’re always just inches away from the next war. And how fluid the world is. My fav series, Wrath of The Kahns is now behind a paywall so go with the newer seasons to get a flavour first.

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