15 stellar podcasts that challenge, educate, and entertain


I love listening to podcasts when walking to work, long distance running, and driving around town.

We are living in a special time as we have never had access to so much superb content. Plus, it’s never been easier to consume podcasts on our phones through apps like iTunes, Stitcher, and Podcast Republic.

I love learning new things and have found podcasts to be one of the most vibrant mediums available today for expanding your perspective.

Here are some of my favorite podcasts and why I love them (in no particular order). I’d also love to know what you are listening to as well.

Under the Influence

This is an awesome podcast about marketing and what’s behind some of the world’s most intriguing and successful business stories. Host Terry O’Reilly used to work in the advertising business so he presents his content with the perfection of a copywriter. His episode on Marketing Hit Songs is particularly interesting.

This American Life

This podcast is in a league of its own. Ira Glass started this show in the late 90s and it’s been a staple in the narrative journalism space ever since. Masterfully produced, TAL uncovers the human elements in our daily - and often mundane - lives. This show always challenges me when I listen to it. In one episode, they visit a car dealership in Long Island and follow the sales team for a month. It’s a fascinating look into the gritty world of car sales and what it takes for a dealership to meet its quota.

Hardcore History

I was a History major in school and I love this podcast because of the way it brings me back to my university days. I credit my Arts degree for helping me establish a successful business career as it forced me to communicate, ask questions, and dig deeper. Dan Carlin is spellbinding as he talks about everything from Genghis Khan to the Second World War. He’s like that cool uncle who always a has a neat story up his sleeve.


Host Nora Young dives deep into how culture is shaped by technology. She explores topics that range from big data to the internet of things and what they mean to the average person on the street. She’s quirky and offbeat which I like.


Jian Ghomeshi scandal aside, this remains an excellent radio show. When he was on the job Ghomeshi did a great job of interviewing guests and uncovering what made them tick. The Billy Bob Thornton interview from 2009 remains a highlight. This is one of the best pop culture podcasts around. CBC has done a good job of keeping the show interesting with a series of new hosts.


I got hooked after hearing about Serial on This American Life last summer.  Geek alert: I listened to 3 episodes back to back while I ran the Toronto ½ Marathon in the Fall. It tells the story of a Baltimore teenager who was convicted for the murder of his ex girlfriend in 1999. He’s been serving a jail sentence ever since. The program delves into the who, what, where and why of the murder. It’s a gripping look at the justice system. This is storytelling and investigative journalism at its very best.

Fresh Air

This is one the best interview format podcasts on the air. Terry Gross establishes a wonderful rapport with guests and gets them to open up. I really enjoyed the episode with David Carr, the rabble rousing New York Times journalist who passed away in Feb 2015.

Planet Money

This gem of a podcast is about the world of money, finance and business. They do a masterful job of explaining complex topics like bond prices and making them accessible to the everyday person. They also explore the business side of everyday things we take for granted (ie. what it takes to deliver roses on Valentine’s Day)


I love, love, love this podcast. It tells the story of how host Alex Blumberg starts his own podcasting company, Gimlet Media. Blumberg is a This American Life alum and he’s one of my very favorites. He is an incredible storyteller as he’s a master of capturing human emotion, especially the awkward bits. This is an honest look into the highs and lows of starting your own business. If you are into entrepreneurship (or business in general), this is a must listen to podcast. The last episode of season 1 is particularly amazing.

Reply All

This is another podcast from Gimlet Media. It’s a podcast about the internet and hosts PJ Vojt and Alex Goldman tackle everything from online dating fraudsters to building a database to the invention of email. It’s quirky and offbeat too.

The Tim Ferriss Show

Let’s get this out of the way first: I’m not a Tim Ferriss/Four Hour fanboy. I know he’s popular, but I never got his whole Four Hour deal. I tried, but no dice. When I learned about his podcast in early 2015, I was skeptical. However, his podcast is excellent. It’s all about uncovering what makes successful people successful. His interviews are funny, inquisitive, and intimate. I particularly enjoyed his interviews with Matt Mullenweg (founder of Wordpress) and Alex Blumberg (public radio producer and co-founder of Gimlet Media). I’m not a full Tim convert yet, but I do give him credit for having an excellent podcast.

Here’s the Thing

This is Alec Baldwin’s podcast where he interviews successful people and what makes them tick. It’s a bit like the Tim Ferriss show, though the difference is in their interview styles. Baldwin is much more laid back than Ferriss. My favorite episodes include those with Ira Glass and John McEnroe

Stuff You Should Know

This is a podcast about all sorts of things you likely don’t know a lot about. Examples include the origins of pinball, bars, or icebergs. Hosts Chuck and Josh take you on a thought provoking and goofy journey through everyday things. It’s always super interesting.

Freakonomics Radio

This is a spinoff of the popular Freakonomics books written by Stephen Dubner and Steven Levitt. Like Planet Money or Stuff You Should Know, they explore surprising facts about things you take for granted or might never have thought were interesting in the first place. Topics range from the design of public toilets to determining what’s more evil: marijuana or alcohol.

PromoKitchen Podcast

Bias alert - this is one I co-host with Danny Rosin, Bobby Lehew, and Kirby Hasseman. As a host, I get the opportunity to learn from some of the greatest minds in the promotional products industry (Jonathan Isaacson, Gene Geiger, Trevor Gnesin, Jordy Gamson, Kamran Popkin to name a few) as well some marketing greats like Seth Godin and Dan Pink.