These are the podcasts we’re obsessed with

There are so many podcasts out there, it can be hard to tell where to start. Here are some of the top picks from across our team!


Here at Eighty-Eight, we’re all suckers for a good story so naturally we gravitate towards podcasts. Each podcast offers us new perspectives and new ways of seeing the world, or even just a little escape into a new and interesting story – whether it’s fact or fiction. We’ve compared notes across all the avid podcast listeners on the team. Take a peek to learn about the podcasts that we can’t wait to have in our ears each week.

Jamie Gillingham

What podcast does everyone need to know about? The Paris Review Podcast

What’s it all about? The Paris Review is a literary magazine, so The Paris Review Podcast dives into the archives of the magazine, with living famous authors and celebrities reading stories and poetry from (not living) famous writers, plus interviews and new pieces from the magazine. Would reco for bibliophiles.

What’s a good episode to start with? The first! It has archival interview footage with Maya Angelou.

Honourable mentions include: CBC’s Writers and Company, Sword and Scale, Always Take Notes

Where are your fave places to listen to podcasts? I mainly listen to podcasts while I’m working. I like a constant level of noise when I’m trying to be productive, but not so much noise that I’m distracted. Also when I’m going to sleep.

Erin Bury

What podcast does everyone need to know about? NPR’s How I Built This

What’s it all about? Each episode interviews successful entrepreneurs across industries – from the founders of Airbnb and Warby Parker, to the founders of Clif Bar and Southwest Airlines – and they talk about where their idea came from, how they got it off the ground, and the challenges they faced along the way – with the end of the episode highlighting how successful they’ve been to date. It’s inspiring, but also highlights the challenges that every entrepreneur faces – and the grit, resiliency, and positivity with which you need to approach growing a business.

What’s a good episode to start with? I love episode one, with Sara Blakely from Spanx – she’s the world’s first self-made female billionaire, and her story about dragging a Nieman Marcus retail buyer into the bathroom so she could show her the before and after with Spanx on really highlighted the lengths entrepreneurs will go to to make their businesses a success! I also love the episode with Whitney Wolfe, the founder of Bumble, and Joe Gebbia, the founder of Airbnb.

Honourable mentions include: I’m a huge podcast listener, and my favourites include Freakonomics (the recent series on The Secret Life of CEOs was amazing), Planet Money (it makes economics interesting!), Criminal (I love anything true crime!!), Reply All (a podcast about tech), The Tim Ferriss Show (interviews with successful people), and Under the Influence (marketing-focused).

Where are your fave places to listen to podcasts? I listen to podcasts at every opportunity. I listen to my favourite ones while I’m running (to encourage me to work out!), while I’m at the gym, while I’m getting ready in the morning (hair/makeup time is now productive!), while I’m cooking (which is very rarely…), on my commute to/from work, walking to/from meetings, and on planes. Basically anytime I have 5 minutes of downtime, I’m pressing play on a podcast.

Brittany Giles

What podcast does everyone need to know about? Still Processing

What’s it all about? Jenna Wortham and Wesley Morris are two culture writers for the New York Times and they put out this weekly podcast that takes a critical look at what’s going on in culture and society. It’s like eavesdropping on a conversation of some of your smartest pals and it’s equal parts insightful while also feeling a little cathartic as they tackle some big, tough news.

What’s a good episode to start with? They tend to be timely and topical so you can jump in with the most recent one and not be lost. Start with this week’s to hear the most relevant episode and work your way back! Some of my favourite episodes include the one about Janet Jackson around the Super Bowl, the Oscars episodes (both this year and last year’s!), “We Get Biracial,” and the episode about Trump featuring Emily Nussbaum.

Honourable mentions include: There are so many worth recommending! Keep It (another culture podcast that is a must-listen), We’re No Doctors (Steve Agee and Busy Philips talk health and medicine), Why’d You Push That Button (about the choices that technology forces us to make), Reply All, Startup, My Brother, My Brother And Me, and random podcast episodes featuring some of my favourite comedians.

Where are your fave places to listen to podcasts? My ideal podcast listening scenario is in the tub, but I also like listening to podcasts in transit (on the streetcar, on the train, on a long walk), or when falling asleep.

Andrea Pace

What podcast does everyone need to know about? Girl Boss Radio!
What’s it all about?  I know, I know, people don’t LOVE Sophia Amoruso (creator of Nasty Gal and host of this podcast), but don’t let that deter you, the podcast is great. It talks to all types of different women, who have all experienced different forms of success in business. It offers a really powerful perspective on what success actually means and serves as amazing inspiration (basically a roadmap) on how to kill it.
What’s a good episode to start with? I think my favourite so far was maybe the Kelly Mullens Brown (President of Ryan Seacrest Enterprises) OR Karley Sciortino OR the Alyssa Mastromonaco episode. I don’t know, they’ve almost all been amazing.
Honourable mentions include: The Daily, TED Radio Hour, The Current, How I Built This, The Moth
Where are your fave places to listen to podcasts? I listen to Girl Boss Radio walking to and from work everyday to get me motivated and thinking.

Jess Tat

What podcast does everyone need to know about? My Dad Wrote A Porno

What’s it all about?A comedic podcast where three friends read one of their father’s self-published erotic novel: Belinda Blinked. Definitely NSFW featuring mature content. (Fun fact — They did a live episode recording at Massey Hall recently!)

What’s a good episode to start with? Right from the beginning. The lore is deep.

Honourable mentions include: Reply All (investigative journalism), Whiting Wongs (race, writing, and television), and currently listening to The Last Podcast On The Left (conspiracies, cults, and serial killers)

Where are your fave places to listen to podcasts? Getting work done or as a bed-time story.

Fatima Almuhtaram

What podcast does everyone need to know about? Creative Pep Talk!

What’s it all about? The podcast is hosted by a full-time freelance illustrator, Andy J Miller, who shares a combination of interviews + stories + tips which are super beneficial to freelance creatives who are trying to build a career for themselves.

What’s a good episode to start with? 153, with guest Lauren Hom. She talks about her side projects and how they helped shape her career. She also shares insight + tips on making shareable content to help you grow.

Where are your fave places to listen to podcasts? Mostly while I work.