Top Ten Podcast Episodes of 2020

I listen to a lot of podcasts each year. (69 days, 18 hours worth thus far in 2020 according to my Podcast Addict stats.) Some episodes merely travel in one ear and out the other, some make me think, and a few have a profound impact on me. And every year I stop to reflect on the episodes that most deeply resonated with me. The following is a list of ten episodes (okay, technically 11 as a new one came out since I started writing this) I find myself thinking about months after I first heard them.

I hope you too will learn something meaningful from these shows. Happy listening!

Choiceology- A Spoonful of Sugar | March 25, 2020

Imagine you have this dilemma. If you do something excruciatingly painful 3x a week for the next 18 months, it will drastically reduce your chances of catching a disease in 30 years. Do you do it? Not many of us would. This was the real-life situation Dan Ariely was in. And he was able to do that using the technique that Choiceology host, Katy Milkman, calls temptation bundling. It is a technique we can all use to better align our short-term and long-term desires.

Chase Jarvis Live- Get Out of Your Own Way- David Hollis | April 15, 2020

Many times a week Chase Jarvis sits down with an eclectic mix of guests, hoping to ignite the creativity in each of us. This episode really stood out to me. Dave Hollis was someone who left a "dream gig" as a studio executive to go down a completely different path.

"The absence of being able to fail, guaranteed my inability to grow"

-David Hollis

Happiness Lab- Psychopaths and Superheroes | April 2020

Time and time again in The Happiness Lab, Dr. Laurie Santos tries to answer the question "what makes us happy?" This episode looks at people who are at the altruistic extreme, specifically people who donate kidneys to strangers. What makes these heroes so different than all of us "common folk"?

Never Stand Still: WNBA Player Diana Taurasi on Success and Staying Grounded | July 29, 2020

I may be promoting the big boss' podcast here (Never Stand Still host Dan Schulman is the CEO of PayPal, where I work) but trust me, it is good. Many of the episodes are amazing conversations with his fellow CEOs like Nike's John Donahoe and Salesforce's Marc Benioff. But my favorite episode of this past season was with WNBA legend Diana Taurasi where they discuss team dynamics. The best teams never look perfect on paper, but their leaders have the ability to meet their teammates where they need to be.

This Week in Startups: Nikola's Trevor Milton | July 31, 2020

If an interviewer asks a founder "What is the product you are trying to create?" it is very telling if the response is, "We are going public because of WeWork, but we're not WeWork." (He didn't ask about WeWork, or your shareholders, he asked about the product.)

2020 has led to some pretty crazy valuations, and potentially none have been as extreme as Nikola. TWIST host Jason Calacanis does a great job of letting Nikola's now-ousted Chairman, Trevor Milton, talk about his company and vision. And time and time again Milton's answers aren't about pleasing customers but pleasing the public markets.

99 Percent Invisible- Podcast Episode | September 1, 2020

Yes, this episode has a perfect title for an episode about generics ("Podcast Episode"). This takes us back to a time in the 1970s/80s when not having a brand was a powerful branding statement.

Econtalk- Margaret Heffernan on Uncharted | September 7, 2020

The future is unknowable and we as humans don't like that. That's the central thesis of Margaret Heffernan's book. But while the future may be unpredictable, it doesn't mean you can't prepare for it.

Masters of Scale- Caterina Fake: Building a More Human Internet | October 2020

Caterina Fake has spent her career from Flickr to hosting the new podcast Should This Exist focusing on "Building a More Human Internet." My favorite takeaway is that when you are building a business, "what you tolerate, is what you are. So, if you tolerate white supremacists on your platform, you’re a platform for white supremacists."

Your First Million- Katrina Lake - Youngest women to IPO / Stitch Fix | November 23, 2020

The road to success has many ups and downs. For Stitch Fix Founder/CEO, Katrina Lake, the day of their IPO was not going as planned. Stitch Fix was being priced below their range and they felt like underdogs. Katrina owned this situation and that gave her and the team the freedom to "do things their own way". And that included bringing her one-year-old son on stage for this iconic photo.

Freakonomics- Does Advertising Actually Work? (Part 2) | November 25, 2020

Does digital advertising work? Probably. How well? It isn't always clear. This is a great episode that has us question, how effective is the digital ad market that drives much of Silicon Valley.

Tim Ferriss Show- Jerry Seinfeld - A Comedy Legend’s Systems, Routines, and Methods for Success | December 8, 2020

I just listened to this episode and keep thinking about it. It is a masterclass in the discipline of creativity and the habits you need to form to get your brain/body to do what you want them to do. Jerry Seinfeld has been doing comedy for over 40 years and he tells us that it is never easy. He sits down every single day and writes- because that's what great comedians do.

BONUS: And if you want to binge something fun over the holidays, check out:

Even the Rich: The Murdochs

For anyone who is having a hard time waiting for the next season of HBO's Succession to come out, enjoy some gossipy tales of the real-life inspiration of the Roy family. Yes, many of the stories are even crazier than what we see on Succession.

What were your favorite podcast episodes in 2020? Tell me in the comments and I will give it a listen!