My most recommended podcasts
I first discovered podcasts, like most of the world, with Serial in 2014. I remember listening to each new episode on the subway the morning it was released, and then eagerly discussing the implications with my coworkers as soon as I got into the office. After the hullabaloo over Serial subsided, a coworker recommended Reply All and Startup, and I devoured both.
A couple of years later, another coworker went to work at fledging podcast startup Gimlet Media—none other than the company whose founding was detailed in the first season of Startup. Long story short: I ended up getting hired as a salesperson for Gimlet in the fall of 2016. It was surreal to come out of the subway one day and have a voicemail from Matt Lieber in my inbox after hearing him on Startup years before.
That’s a long intro to say: I spent seven years selling ads for podcasts, and along the way, listened to a lot of podcasts. My preference is generally for more highly produced and edited narrative podcasts (aka you won’t find many chat shows on this list), but my interests fall into a wide spectrum. I prefer to listen at 1.8x speeds (which helps me squeeze a lot more listening in!), and I tend to listen whenever I’m doing something else—driving, cooking, cleaning up around the house. Most of these recommendations are biased toward longer-running and regularly-publishing series, but I do love a binge release. Alas: my most recommended podcasts are below, and feel free to drop any of your favorites for me to check out in the comments!
If you like true crime but aren’t into the gore:
Criminal offers some of the most original and interesting takes on stories of true crime. A few of my favorite episodes: The Kit, Masterpiece, Crazy Eddie.
Crimetown is a sprawling and detailed look at the pernicious corruption of politics in Providence, Rhode Island. Start with episode one, season one. (Season two covers a similar and yet wholly unique winding tale of corruption in Detroit.)
If you want to laugh and cry in the same 30 minutes:
Heavyweight is probably my all-time favorite podcast. It’s hard to describe the premise, but somehow host Jonathan Goldstein manages to tell the most heartwarming stories while delivering brilliant one-liners and solving decades-old mysteries all at once. A few of my favorite episodes, although I generally recommending starting at episode 10 and going up from there (with maybe a stop at #2 Gregor, but I generally think the show really found its stride in season 2): #16 Rob, #24 Jimmy & Mark, #30 The Marshes.
If you want to just listen in on a low-stakes gossip story that doesn’t involve anyone you know:
Normal Gossip is made up of these delightful this-crazy-thing-happened-to-a-friend-of-a-friend-of-a-friend episodes, the sort of thing that might immediately make you perk up your ears when you’re out to coffee or dinner and a friend mentions she has a WILD story to tell you. A personal favorite for when I am bopping around cleaning the house on a Saturday morning. A good episode to start with is ‘Til Deb Do Us Part or Rich Mom Razzle Dazzle.
Similarly, You’re Wrong About will take a pop culture name or history topic that you haven’t heard about in years and thoughtfully dissect and disrupt everything you thought you knew about it. A few favorite episodes: Fleetwood Mac’s Rumours, The Donner Party, The Stanford Prison Experiment, Human Trafficking.
If you want to quit your job to do your own thing (or if you want to just live vicariously through other people making the leap):
How I Built This is the OG of this genre, and for good reason: I love learning more about the origins of my favorite companies (as do millions of others). Spanx is one of my all-time favorite episodes with an incredibly persistent and inspiring female founder, but I recently deeply enjoyed the conversation with the two mom founders of Primary—which is one of our go-to places to shop for Jojo.
Second Life focuses on female founders who became entrepreneurs after having a career in a different field. I especially loved learning about the story of Sugarfina!
The Pitch is where real companies pitch real investors for real money. I’m not that deep in the world of venture capitalism, but I love learning more about the companies that are being founded right now and I also enjoy the voyeurism of the “will they or won’t they” get any money. A couple of my favorite recent episodes: ECGO: Turning Trash into Treasure with AI and Bevz: A Tech Bro Walks into a Corner Store.
A bonus option here: the first season of Startup still holds up, IMO!
If you would like to be enraged about:
Freeways and noise pollution and smog, listen to Freeway Exit. (It’s based in San Diego, so an especially local element for any fellow San Diegans!)
Bureaucracy and infrastructure and how anything gets done (or doesn’t get done) in this country, try The Big Dig. (Especially relevant to those who grew up in the Boston area!)
The state of the American education system, specifically children’s literacy, try not to pull your hair out listening to Sold A Story. It has made me *fully* committed to phonics in our household (and very grateful for that cassette tape set of Hooked on Phonics that I had growing up!).
The state of our prison system, check out Ear Hustle (although I suppose this enrages me less and mostly just makes me much more aware of the inequities in our justice system as well as the ways that justice is very much not served).
If you want to improve your relationships by learning lessons through other people’s problems:
Where Should We Begin with Esther Perel is a chance to be a fly on the wall for couples counseling. It generally makes me feel better about the state of my own relationship (people out there are dealing with a lot!), but it also often gives great insight and advice on how to tackle certain difficult conversations or how to reframe a problem in your own personal life.
Nurture vs Nurture with Dr. Wendy Mogel is a similar conceit, but for parents counseling. Although not all of the parenting issues are relevant for me (yet), it’s interesting to hear how different families approach raising children and dealing with concerns.
If you would like self-contained episodes that answer some sort of question, often related to technology:
Although Reply All isn’t publishing new episodes anymore, the archive is still a gem of internet-related queries. My personal favorites: 30-50 Feral Hogs, Dark Pattern (RELEVANT FOR TAX SEASON), Long Distance (probably my most recommended podcast episode ever), On The Inside.
Search Engine is former Reply All host PJ Vogt’s new personal project, and although I think it’s missing the full magic of the Alex-PJ dynamic, I have been interested in the questions that he’s been exploring such as why are there so many chicken bones on the street (a question that vexed me with a young hungry pug living in Bed-Stuy) and why can’t we just turn the empty offices into apartments.
If you want to know the BTS of all of your favorite writers (or be inspired to read something new):
Longform is exactly what it sounds like: long conversations with writers, generally those who write longform articles and deeply reported non-fiction books although there are occasionally some novelists thrown in there. As someone who loves to read (and who is generally daydreaming about how to write more), it’s always interesting to learn more about the process behind some of these incredibly detailed and thoughtful pieces.
If you are currently singing Baby Beluga on repeat in your house, as I am:
I thought Finding Raffi was such an insightful look at this children’s music legend. He has led such an interesting life, and I learned so much about his environmental activism in the 1990’s. I grew up listening to a lot of Raffi on cassette tapes, and after this listening to this series, I’m A-OK with Raffia being the main source of music for Jojo as she grows up as well. (Side note: he is coming to San Diego for a live concert this month and I am SO tempted to go, even though I think Jojo is a little too young to truly enjoy it!)
If you would like thoughtful conversations on topics that aren’t often discussed:
Death, Sex and Money is a classic. Host Anna Sale is sensitive and inquisitive, and interviews often go places (i.e. about death, sex or money) that most other shows won’t go.
If you already listen to The Daily:
Plain English with Derek Thompson is my favorite for thoughtful commentary on the news of the day. A few favorite episodes to start with: why the US media industry is in meltdown, why it’s so hard to buy a house right now, what’s so great about marriage?
What else should I be listening to?!
