GREATEST HITS NO 3: STARTUP BY ALEX BLUMBERG

In the fall of 2014, sitting in my Brooklyn apartment, I cracked a beer and popped on the first episode of a new podcast that everyone seemed to be talking about – a show called StartUp. It began simply, with the host, a guy named Alex Blumberg, talking directly to the audience. He said he’d been a producer at This American Life and was the co-creator of a podcast called Planet Money, but that he'd made a rash decision: to stop reporting on other people’s businesses and launch his own.

I’d heard this guy on the radio before but didn’t know much about him. I wasn’t immediately grabbed. But he continued,

I love podcasts. I love making them, I love listening to them, but there’s all kinds of podcasts out there. From a couple people talking around a mic, to the kind that I make, and that I have a particular soft spot for, which focus on storytelling and journalism.

I thought: Hey! Those are the kind of shows I like!

It seemed like someone should come up with money to invest in making new shows like these, and come up with a theory about how those shows could be profitable.

Synapses fired in my brain … pistons and gears that had rusted over began whirring ...

And then came this thought, a thought that’s gotten a lot of people into a lot of trouble. The thought: Well, I could do that.

And I thought: Well, I want to do that, too.

StartUp was released right around my 29th birthday.  I was an actor in New York City, feeling progressively more bored with each job I booked, each commercial for some car or soda or clothing brand that meant nothing to me. On the side, I worked at a bar that was essentially a wedding venue, pouring drinks for thousands of happy revellers who had no idea the depth of rage their friendly waitstaff felt for them as they howled along to “Don’t Stop Believin’”  at midnight – the same as the crowd the night before, and the crowd the night before that. When the greatest day of someone’s life makes you feel furious, it’s time to admit that you’re in a rut.

Enter podcasts. For years I’d been devouring interview shows like WTF with Marc Maron , You Made It Weird with Pete Holmes , and The Nerdist Podcast , to the point that I decided to produce my own interview show about the acting business called Broken Legs (this has since been scrubbed from the internet, sorry). But 2014 was the year that the word “narrative” began seeping into my consciousness. A new network called Radiotopia  had popped up and I was getting hooked on their shows, especially Love and Radio , Radio Diaries , and 99% Invisible . I desperately wanted to make those kinds of podcasts. And then, drinking a beer on my beaten-up couch, I found out that some public radio guy was trying to start his own company – in Brooklyn, no less – where I might be able to learn how.

StartUp immediately felt different than the other things I’d been listening to. It was confessional, stripped bare of pretence. Instead of positioning himself as some sort of guru with unflappable confidence, Alex leaned instead into his ineptitude, his awkwardness, his anxiety. That first episode follows him to California  as he tries to convince one of the most influential venture capitalists in the world, a guy named Chris Sacca, to give him money. Alex fucks it up, big time. But not only does he admit to fucking it all up, he’s out there, with his microphone, recording all the cringey ways in which he fucked it up:

CHRIS: If I were calling an Uber right now and it said it’s going to be here in two minutes and that’s all the time you have…what are you doing?

ALEX: So I’m making a network of digital podcasts. Uh. That we will moneti– That we will … That is gonna meet– [awkward laugh] Sorry.

From a narrative point of view, these failures are rich. Like trying a funky cheese of which, despite its funkiness (or perhaps because of it), you can’t wait to have more. And beyond that, it’s like if that funky cheese was a secret funky cheese, a funky cheese most cheesemakers keep only to their privileged cheesemakery selves.

I rooted for Alex. I cared about him. I wanted this bumbling man to succeed. Early on, we hear him waking up in the middle of the night to confess his fears about starting a company while being a parent. At another point, when he suggests that he should call his company “Orello”, his wife, Nazanin, bursts into uncontrollable laughter. And when he later asks Nazanin if she thinks their marriage will last, he gets a very long pause in response. It’s a masterclass in how to build emotional stakes into a story.

I have to admit that I became less interested in the show the further the season progressed. This says more about me than anything else. I’m a sucker for the dream phase of a project — the time right before an idea is actualized, when everything’s possible, adrenaline’s in plentiful supply, and the future seems to be beckoning you with a smile.

By the sixth episode of StartUp , this phase is over. Alex ratchets up the meta dial and explains how the first two episodes of StartUp have just been released to the public. His new show, and his big idea for a company – he’d settled on the name Gimlet  – is out in the world, and it’s attracting a ton of attention. We hear a big-time investor reach out to Alex, offering to drop $150,000 as casually as if he was explaining his dinner plans. Alex eventually decides to open the final chunk of Gimlet’s funding to the listeners themselves, and it only takes a few hours for the slots to fill up. Gimlet has been born. And it’s a gigantic, expectation-laden baby. Alex succeeded in creating the thing, he succeeded in making people care about the thing he created, and now the question was whether the thing itself would succeed.

So did Gimlet succeed? Well, to its investors, the company was a home run crushed to the nosebleed section, a certified no-doubter. In 2019, Spotify acquired Gimlet for a reported $230 million , inhaling it into its own big-tech belly and coughing up more than a few millionaires in the process.

Much hand-wringing occurred within the podcast community when this happened. To many, it seemed to portend an ominous shift in the industry, one that would lead to the squashing of independent creators and innovative shows in favour of more generic profit-churning mundanity. To some extent, regrettably, this has come to pass. But I don’t entirely blame Gimlet for it.

First off, if Gimlet wasn’t the poster child for big tech acquisition then another podcast company would have been. It’s just the way life is now. Blame … Zuckerberg? Bezos? Scrooge McDuck? I don’t know.

Second, Gimlet was at the crest of a wave of companies that changed – for the better, I’d argue – the way we make and consume podcasts. Just by deciding to produce a meta-confessional show like StartUp, Alex pushed against the many storytelling conventions wrought through decades of American Public Radio dominance (while also being influenced by those conventions, of course). How many great “reporter’s journey” podcasts are there now? He didn’t invent the conceit, but Alex made a show that was so well-told, and so quintessentially him, that it felt revolutionary. And Gimlet, by extension, felt revolutionary too. Not just to listeners, but to the people who flocked to work there. I know this, because I was one of them.

You thought I’d dropped the thread of my own journey, did you? Here’s one of my own little storytelling tricks that I learned at Gimlet – push information back. Maximise surprise.

I joined Gimlet at the start of 2016 as a 30-year-old intern. It was the beginning of a new career, one that would change my life more than I ever thought possible. Gimlet was an often-brutal boot camp; I worked constantly, ignored my personal life, and was exposed to infuriating structural issues that I’d rather discuss over a beer. But I got to work with my heroes, absorb as much of their knowledge as possible, and feel a part of a community of people who were lovely, driven and inspiring. Plus, I met the woman who would become my wife. Weren’t expecting that, were you? I certainly wasn’t.

Those early, heady days at Gimlet represent the dream phase of my current life. So now, when I re-listen to StartUp, I prefer to put myself back in 2016. I prefer to enjoy the show like I would a popular band from middle school (Third Eye Blind , for me) that comes on and slams you with waves of nostalgia — all braces and rollerblades and first kisses in darkened basements. That deep-in-your-gut thrill of being on the verge of a new future.

All that’s left is possibility. A hapless man believing he can create something great. A lost kid who’s been offered the chance to join in. A semi-charmed kind of life. Doo doo doo, doo doo-doo doo…

Listen out for: All of the cringey ways in which Alex bravely embarrasses himself in Episode 1: “How Not to Pitch a Billionaire” .

Hit replay: The entirety of episode 12: “Burnout” . Lessons for podcast companies everywhere.

See also: “Planet Money Makes a T-Shirt” , the Planet Money miniseries that follows the worldwide journey of what it takes to make a t-shirt. This was released just before Alex decided to quit and start Gimlet, and is arguably his most well-known project before that.