11 curated podcasts picks (2019 Q2)

In issue two, podcast picks, the update by jayclouseLeave a Comment

by Jay Clouse and Eric Hornung

Everyone knows the world of podcast episode discovery is broken. Whether podcast player charts, socialized discovery recommendations, or someone putting in the work of collecting answers to “what’s the best podcast you listened to this week?” – there is one underlying theme to podcast episode discovery. In the words of the fictional Barney Stinson, “New is Always Better

When you do daily or weekly podcast curation/discovery, you are helping filter the signal from the noise each week. What if you did something monthly or quarterly? You’d reduce your total number of recommendations from 365 or 52 to 12 or 4.

That strong filtering is what we do here in this part of the update, a curated quarterly publication about trends, stories, and editorials outside of Silicon Valley. Jay and Eric listened to over 400 episodes in the last three months and are giving you:

  • a Consensus pick – the podcast episode Eric and Jay most agree on
  • a Classic pick – Jay and Eric’s individual picks that tackle a topic near the intersection of finance and entrepreneurship
  • a Contrary pick – Jay and Eric’s individual picks that aren’t immediately intuitive

And here’s where it gets fun. We brought on some friends to partake in the quarterly curation task. Scroll down to find recommendations from Justin Jackson (@mijustin), Natalie Sportelli (@N_Sportelli), and Colby Donovan (@colby__donovan).


For the Billions of Creatives Out There

Brian Koppelman
a16z podcast
Listen Here


What Jay and Eric like about it:

Whenever Jay and Eric get a chance to hear from successful creators, it usually hits a cord of mutual understanding. Add in an early stage investing spin and this episode was made for the upside team.

Jay and Eric have had a motto at upside to build consistently and get a little better every week. When we have the choice to focus on making a better product or growing a larger audience, we have selected the former. One of the main takeaways of this episode, according to podcast notes, is Brian’s advice that you should “trust that if you find a way to do the work well enough, and show up every day, the rewards will come over time.”

Overall this was a fun episode that linked together venture capital and creating in a fun, entertaining, and enlightening conversation that is highly pertinent to what we do on a daily basis.


Trey Ratcliff – photography, forest bathing, buying instagram followers, and more

Trey Ratcliff
The Kevin Rose Show
Listen Here


What Jay likes about it:

I think the Kevin Rose Show is totally underrated. Kevin has the influence to pull in some really fascinating guests, and they typically aren’t making the rounds on other podcasts.

This episode in particular hears from a creative I’d never met who picked up the camera later in life. Now, he’s writing books with the stated goal of “increasing the level of consciousness in the world.”

The guy very clearly is living exactly the life he wants and has built a lot of great perspective in doing so. He dives down a rabbit hole of how Instagram “influencers” can be totally fabricated (he did it) and exactly how they do it.

Very easy listen, you’ll learn a lot, and walk away refreshed.


Emergency Broadcast – Josh’s Announcement

Josh Brown
The Compound Show
Listen Here


What Eric likes about it:

This year, Jay and I incorporated The Up Company, the company that runs upside and publishes the update, in a move that was symbolic of our realization that there is real potential in this hobby as a business. We’re still figuring out what that vision is, where we fit, and what our goals are so a lot of our time is spent exploring. What about this? How about that? Let’s try the other thing.

Why I love this episode is that it gives a little insight into what a CEO with a clear, crisp vision looks like. Someone who knows what the mission is, what success looks like, and knows that nothing is going to stop the team from achieving it. In an industry where 30 hour work weeks, captive clients, and high fees are the norm; the Ritholtz persona, from what I can gather, is that of outsiders fighting a system that favors insiders. Not so dissimilar from our position at UP.

If you run a business or manage people, you’ll enjoy this quick episode. Here’s my favorite section.


Sage Advice (and Reasons You Probably Won’t Follow It)

Jason Cohen
The Indie Hackers Podcast
Listen Here


What Justin Jackson likes about it:

Jason Cohen’s wisdom is so helpful, because he’s willing to admit that it really depends on the individual.


Leading Millennials to Financial Independence

Vicki Robin
Secrets of Wealthy Women by WSJ
Listen Here


What Natalie Sportelli likes about it:

There’s been a ton of writing on how talking about personal finance can benefit women. The podcast dives into all things money, savings, and financial planning, featuring high profile women across sectors and offers really valuable insights into professional development. Financial security and being smart about saving are important topics to me, so hearing people who’ve been successful in those capacities is definitely aspirational.


Robert Sapolsky, Ph. D.: The pervasive effect of stress — is it killing you?

Robert Sapolsky
The Peter Attia Drive
Listen Here


What Colby Donovan likes about it:

There aren’t many people I enjoy listening to more than Dr. Sapolsky. As someone who provides short-term foster care and whose wife is a child welfare case manager, seeing the ideas Dr. Sapolsky discusses (impact of stress, trauma and poverty) manifested in some of the children we have had has been incredibly eye opening.

Dr. Sapolsky discusses the connection between these three factors and our brains makeup over time, how stress and trauma literally transcend generations biologically, and how our behavior is altered when we are under stress. Regardless of your profession, this is a insightful episode to help understand our behavior as well as the people around us.


Ryan Holiday

Ryan Holiday
You Made It Weird
Listen Here


What Jay likes about it:

I’m an admitted Ryan Holiday fan boy. The good news for me is that he’s been doing a lot of podcasts lately, including one of my favorites, You Made It Weird. My oddball pick last quarter was also a You Made It Weird episode.

Ryan is just one of the smartest guys I hear from. Not to mention he is living the life that I aspire to live, making an income from writing books. Which, of course, he talks about in this episode quite a bit!

This is a rare 2.5 hours of single-session Ryan Holiday. So in a long episode like this, he gets into the weeds on his writing habits, the way he sees the world, and more. Pete’s a weirdo, mystic too — and so pulling some of the less soundbite-y perspective out of Ryan was refreshing.


Connor, Painting

Ian Chillag
Everything is Alive
Listen Here


What Eric likes about it:

This show has been on my “to listen” list for quite awhile and I recently binged the 16 published episodes. I love the premise of being able to have a conversation with an inanimate object and would love to hear more behind the scenes of the creation process for this show. It must be incredibly difficult to put yourself in the shoes of something you cannot relate to.

Howard Stern recently appeared on The Late Show with Stephen Colbert and Stephen was recounting a story about Howard asking Stephen a question to which Stephen’s only reply was “how did you know to ask that?” One thing that makes a great interview, in my opinion, is the host’s ability to ask questions no one else knows to ask. Pertinent questions phrased in a way that elicit a unique, personal response that capture a layer of emotion.

Between two humans, a beautiful conversation is so nuanced that the difference between a great interview and a legendary interview is difficult to dissect. Everything is Alive brings great interviewing out in caricature and reminds us that everybody has a perspective that we don’t fully understand.


Preparing the Way

John Siracusa
Reconcilable Differences
Listen Here


What Justin Jackson likes about it:

John Siracusa is a maniac for details. The story of him buying a fridge is incredible


Dr. Death

Listen Here


What Natalie Sportelli likes about it:

I was never one to watch Grey’s Anatomy or other medical shows (besides Scrubs), but I was completely captivated — and creeped out — by Dr. Death. What I loved about this podcast was the depth of the storytelling. Its extremely powerful investigative work exposed problems with the medical system, and this story brought some justice for the victims and families of those involved.


Behind the Scenes of Financial Fraud

Bloomberg Markets
Odd Lots
Listen Here


What Colby Donovan likes about it:

This is one of my favorite lessons I’ve ever listened to. Financial fraud is something that captivates everyone and it’s not often that someone who purposely committed fraud is an open book about what transpired.

Crazy Eddie was a NYC electronics retailer that committed fraud for years and the CFO, Sam Antar, is the guest on this episode. He got a college degree and passed the CPA exam on his first try, all the time knowing that he was going to use his knowledge to commit fraud. He explains what and how they committed fraud (income tax evasion and insurance fraud) and were able to get away with it for years by distracting auditors with beautiful women he hired just for that purpose. They didn’t get caught until after they were public and the stock tanked, making them an acquisition target and more scrutinized. This episode is a good reminder some people are full of sh*t and you have to beware of what people say and do.



Jay Clouse and Eric Hornung are the co-founders of The Up Company, co-hosts of the upside podcast, and co-editor of the update.