“Our product is to surprise you.”

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For our first time hosting a guest speaker in our New York City location, we had a clear vision: to bring in inspiring entrepreneurs from a mission-driven, venture-backed NYC media startup. Alex Blumberg and Matt Lieber, co-founders of Gimlet Media, the 2 year-old Brooklyn-based podcasting company behind titles including StartUp and Reply All, immediately sprang to mind.

They joined Matter Managing Partner, Corey Ford, to share their personal “Drunken Walk*”: the transition from public media and business consulting to entrepreneurship, the birth of Gimlet on a Brooklyn rooftop, their foray into sponsored content, and their legacy-building work as champions of podcasting talent.

A tale of two former public radio producers

In Silicon Valley, startups are born on the oil-stained floors of parental garages. In Brooklyn, a graffiti’d rooftop is the suitably lofty equivalent. That’s where, fueled by beers and reflections on the shifting sands of the audio landscape, Alex Blumberg and Matt Lieber joined forces to co-found Gimlet, famously slated to become “the HBO of podcasting.”

Matt Lieber hasn’t always known what he wanted to do: “People tell you you should find your passion. I’d be like…I don’t have a passion.” Once upon a time, Lieber worked in public radio producing shows such as NPR’s On Point, before going back to school to get an MBA (“I woke up to the fact that businesses were a way you could have a really big impact in the world.”). He then went through the “intense bootcamp” experience of Boston Consulting Group, advising financial services and media companies as a management consultant. But he couldn’t get digital audio out of his system: “I was obsessed with podcasts.”

Lieber wanted to build a new kind of media business that disrupted the audio landscape like the web had upended the newspaper industry. After he went around touting the idea to everyone he could, a friend introduced him to a kindred spirit, Alex Blumberg, co-creator of NPR’s Planet Money podcast and a former producer of This American Life. The pair realized they had exactly the same vision, similar backgrounds, and complementary skills. Lieber worked 70 hours a week balancing his newfound “demon drive” with a full-time job and two small kids, wrote a business plan, came on as partner, and helped Blumberg get Gimlet off the ground.

“I didn’t know what venture-backed even meant. In my mind I thought I was going to go find some rich people.”

Blumberg says he was a “reluctant entrepreneur, forced out of the nest in a certain way.” Although he felt confident that he had a safety net should the startup go kaputt (“I had a good job, I figured I could get another good job”), leaving his former co-workers in “the warm bosom of public radio” was a hugely emotional wrench. He wasn’t prepared for the realities of being a founder, imagining he could ride to glory on the shirt-tails of previous successes: “I didn’t know what venture-backed even meant. In my mind I thought I was going to go find some rich people. I was really that naive. I really thought it was going to be that I had this proven track record at work on these [radio] shows that were at the top of the charts.”

Starting StartUp

His naivety is already a well-told story. It was captured in Gimlet’s first season of StartUp, a reality TV-style, “warts and all” podcast about founding a startup that produces podcasts. In it, Blumberg laid bare dozens of tricky moments that arose “when someone who knows nothing about business starts one” such as splitting equity between partners, finding a name for the company, and pitching to Silicon Valley super angel, Chris Sacca (Blumberg’s botched attempt is the stuff of legend). Not only was it a great marketing exercise, it proved that the team was capable of producing podcasts on a par with This American Life. Now in its third season, StartUp has since profiled the struggles of a clutch of other startups, including Dating Ring, Grooveshark, and Bento.

Last December, Gimlet raised a $6 million Series A round, bringing its fundraising total to $7.5 million. Yet, as a media company, it has had a vexed relationship with venture capitalists seeking 10X growth. “I think media companies can be really large, valuable businesses,” says Lieber. “But it takes a little more time than it takes to build a technology company where you can have really rapid scale and effects.” “It’s never going to be a hockey stick,” adds Blumberg. Despite assuring them he was the “Steven Spielberg of radio,” he says he had difficulty calming tech investors’ nerves because of the fickleness of the media “beast”, and the lack of available data to guide investment decisions.

“Our product is to surprise you and so therefore you can’t help us.”

Heads, not tails

Unlike the Buzzfeeds of the world, which distribute the content they produce in-house, Gimlet relies on RSS feeds to push its podcasts to a wider audience, meaning producers are sometimes speaking into a metrics void. This is a problem that technology will eventually remedy (though Gimlet is not planning to build its own app). In the meantime, the co-founders are confident that high production values and tightly-edited, powerful storytelling will prove to be their sustainable competitive advantage. “We don’t want to have the most shows, we just want to have the best shows,” says Lieber. “We’re not trying to make a business from the long tail.”

Their business is in fact selling “novelty, surprise and delight.” As such, the Gimlet development process runs counter to what many Lean Startup methodology adherents, and indeed Matter startups, tend to practice. Blumberg and Lieber believe getting a Minimum Viable Product out in the world would undermine the value of their offering, so they set the bar very, very high from the get-go. Their long-form audio narratives are production-heavy labors of love: “We’re not about putting out products that aren’t yet ready. We’re very much like ‘let’s make it f*****g amazing, so that when people hear it, they’re like holy s**t,’” says Blumberg.

Paradoxically, even though the listener is at the core of everything Gimlet does, its editorial teams don’t often speak to their users. Instead they rely on their own taste and experience to stand as proxies for their audience. “You don’t by definition know what’s going to surprise you,” says Lieber of podcast listeners. “So we have to come up with that. Our product is to surprise you and so therefore you can’t help us.” Gimlet borrows from the Steve Jobs school of thought, says Blumberg, i.e. “[consumers] don’t know what they want until we make it.”

“A lot of the great elements of good tape you can find in the book of Genesis.”

The “group edit” gauntlet

To attain those high production standards, every story goes through rigorous layers of editing. After a reporter has written a draft, it is pored over, “brutally criticized”, and collaboratively rewritten by five or six colleagues. Every group edit is a skill-building exercise, with newer members “learning the vocabulary of how you fix things,” including how to give and receive feedback (which Blumberg and Lieber believe is a gift, just as we do at Matter).

“We’ve been telling stories sort of since we’ve been, you know, human,” says Blumberg, who says he honed the craft under the tutelage of This American Life legend, Ira Glass. “One of the things I teach is what’s good tape. A lot of the great elements of good tape you can find in the book of Genesis.” To nurture new storytelling talent, Gimlet is working on its own academy, including a training curriculum of production basics for wannabe podcasters, and an internal radio masterclass every Friday morning.

Recently the team has been bringing its narrative prowess to bear on sponsored content. Gimlet’s new creative agency has just launched Open for Business, an eBay-branded podcast about starting out in entrepreneurship. While the brand has ultimate creative control, Blumberg and Lieber seek to cultivate balanced partnerships where Gimlet’s editorial and the client’s marketing teams are in step. They believe audio offers a unique conduit for a company’s message to an audience, and a unique opportunity to capture a listener’s undivided attention in those quiet moments, such as in the car or on the train as they commute to work.

“We’re great at doing brand advertising on your mobile phone. We can tell a really rich story,” says Blumberg. “We think audio is really good at doing things that no other medium is really as good at. It’s really about empathy and helping us all understand each other better and understand the world better.”

*The Drunken Walk is a series of live fireside chats, blog posts, and podcasts (coming soon!) from Matter Ventures, the world’s only independent startup accelerator for media entrepreneurs. We dive into the personal stories of founders, experts, and innovators in media to uncover the moments in their careers that changed everything. Our goal is to inspire and empower the next generation of media entrepreneurs to get from A to B without a map.