Podcast Review: Start-Up by Gimlet Media

I just finished binge listening to Start-up; 5 seasons, 60 episodes and 2,263 minutes of listening time. Before you commit 1.57 days of your life to catching up, read through my season by season review.

Season 1: If I had one word to describe this season, it would be honest. From the very first episode, Alex Blumberg, Gimlet Media's CEO, shares his dreams, his worries and his awkwardness with complete honesty. His dreams to own and run a podcast company. His worries about quitting a solid job. His awkwardness… in almost every way.

But it is his honesty that endears, not only his listeners, but investors, to him. His awkwardness as he stumbles through pitches and business deals. So many cringe worthy moments where I felt like “Yes! It’s not just me who is making it up as I go.”

This season really is the epitome of the show. It is so refreshing to hear as-it-happens telling’s of a real life start-up, and one that has gone on to do some incredible things.

It would be amiss not to mention how Alex’s wife, Nazaneen, contributed to the season. It was obvious that the good and bad of achieving his dream, was her reality. She supported his goals, laughed at his lame company names and was an analytical sounding board for him, with several dashes of wit.

Season 2: In season two, Lisa Chow joins Alex as co-host. And with a new season and a new host, comes a new start-up to focus on.

The ladies of “Dating Ring”, Emma Tessler and Lauren Kay, bring a new approach to online dating, with their more personalized matchmaking app. This season started off strong, with a powerful pitch to investors. I am immediately on board with Emma and Lauren as they struggle not only with navigating the world of tech start-ups, but also navigating it as women.

Soon enough, it becomes clear that there isn’t one dating ring to rule them all.

Emma and Lauren struggle. They struggle through most of the episodes. With investors, with subscribers and with each other.

If you like happy endings, don’t listen to this season. But if you like to hear about the reality of starting and coming to grips with building a business, listen to this season.

BONUS: There are six bonus episodes where we revisit Gimlet Media a year later. Again, we get an honest look into the company and how they are doing. They are growing (Nazaneen joins the team), they are taking an honest look at diversity and corporate structure, and they are learning about the growing pains of moving from a start-up culture to a full blown company. If you skip season 2, at least listen to these episodes!

Season 3: In this season, Gimlet changes things up. The show no longer focuses on just one start-up, but features several companies for one or two episodes. I’ll be honest, some episodes were forgettable. I had to re-read the synopsis to remind myself of each story. Here are the ones I suggest:

Episode 3 and 4: Grooveshark, the music streaming app that famously shut down following allegations of copyright infringement. These two episodes, for the first time, focused on a company I have actually heard of! A very interesting story and quite the fall from glory.

Episode 6: This episode reminds me of season 2 all wrapped up in one episode. Bento Box is high quality fast food service app, where delivery guys are sitting in cars at the ready for incoming orders. The concept is interesting, but extremely hard to apply. These guys face a lot of the same challenges as Dating Ring, but with the added complexity of fresh food.

Episode 7 and 8:  – I liked these two episodes best of the season; call me a sucker for the underdog story. Con Body features an ex-con who lost tons of weight in jail. He turned his darkest hours into something positive; a fitness business that integrates jailhouse style workouts. I also loved that his business wasn’t tech based and that his primary clients are millennial females (me!). Who doesn’t love a bad boy?

BONUS: No bonuses

Season 4: As the success of the show grows, the interest of “big names” does too. This season is about Dov Charney, founder of American Apparel, and his new venture, LA Apparel.

From one episode to the next, I went through wide ranges of emotions. First I admire his genius, next I’m disgusted by what a pig he is. While this season does talk somewhat about his new venture, there is a lot of looking to the past. Looking at who are how he was when he ran American Apparel. This is a memorable season, but one that left me feeling ookey. I would like to give my kudos to Lisa Chow for putting up with his shit!

BONUS: The bonuses on Gimlet Media are interspersed within the regular season, perhaps to give us some relief from the polarizing character that is Dov Charney.

Season 5: This season goes back to the format of season 3, where multiple start-ups are featured. The team has clearly grown, as each episode is led by a different producer. The quality of the show has also changed and each member of the team can focus more deeply on their subject. From the slap bracelet to cricket chips to the universal flu vaccine, this season covers a wide range of businesses. My particular favorites were episode 2 and 3 on Friendster and episode 10 on the most expensive coffee.

BONUS: There are two episodes from the Gimlet Media offices in this season. Episode 7 that revisits previously featured start-ups was somewhat sad to listen to, since none had achieved their goal. Episode 9, was another honest look at the company, this time with the listeners asking Alex Blumberg their questions.

There are takeaways with every episode, and each is incredibly well produced. I hope this review helps you decide which episodes are for you.

And if you were worried about the amount of time I spent listening to this show (1.57 days), don’t worry, I didn’t do it in one sitting. In fact I wasn’t sitting at all. I was walking, I tracked 152,841 steps at the same time 

How and where do you listen to your podcasts? Comment below with your thoughts on Start-up!

1 thought on “Podcast Review: Start-Up by Gimlet Media

  1. Solid post! I actually wasn’t aware of this. It’s refreshing to read because I get so annoyed when writers put no thought into their work. It’s obvious that you know what you’re writing about. I shall definitely visit again!

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