The real magic of StartUp, a new podcast about one man's attempt to launch a podcast network, is that it shows--warts and all--the real experience of building a company. The man broadcasting his adventures is former NPR economics reporter and Planet Money co-founder Alex Blumberg, and the company he's building is called Gimlet Media.

Over the course of seven episodes so far, you hear Blumberg fumble a once-in-a-lifetime meeting with VC Chris Sacca, admit to an investor that he doesn't get Excel, and have tough conversations with his critical but helpful wife, who isn't afraid to laugh in his face. It's entertaining raw material, to say the least, and a big part of what makes Blumberg so endearing. You really want him to succeed, but it's hard not to laugh when he royally screws up. Besides, what's a story without conflict? 

"From a story perspective, that's a natural," Blumberg says of his gaffes. But he admits recording StartUp is "a strange, schizophrenic experience. It is a very conflicted feeling knowing that the producer, me, wants one thing and the character, also me, wants a totally different outcome." 

From a listener's perspective, the extreme transparency makes the show so addictive. But for a founder, is it wise to reveal so much when your reputation--and more than a million investor dollars--are on the line? It's not unusual for entrepreneurs to rehash some gory startup details--but usually that comes after they've found success. Could broadcasting everything as it happens come back to haunt Gimlet? 

I decided to put that question to Blumberg and to the investors who have appeared on StartUp podcast.  

The Virtues of Oversharing 

Much of Blumberg's charm comes from the fact that he owns up to everything he doesn't know--which is a lot. You'd think that charm could only go so far. At a certain point, ignorance isn't exactly an ideal founder quality, right? At least one investor I talked to said that Blumberg's openness might have made the pitching process harder than it needed to be. 

Investors "want to hear the aha! moment, and the uglier and messier it seems, the more they'll poke holes in it," says Micah Rosenbloom, a seed stage investor with Founder Collective who appears on the podcast but has not invested in the company. "The more nitty-gritty details there are around relationships, the bigger the window you have into the company, and the more there is to find wrong with the company."

But that's a risk Blumberg is willing to take. And so far, he says, instead of repelling investors, his candor mostly has helped him build credibility. 

Investors actually want a founder like him--someone who knows what he knows and knows what he doesn't know. In fact, Blumberg's clear lack of business acumen led him to enlist his co-founder, Matt Lieber, when Matt Mazzeo, an investor with Sacca at San Francisco's Lowercase Capital (which eventually backed Gimlet Media), politely suggested he find one. "That was very valuable, recognizing I'm not going to do this on my own," says Blumberg. "That took me on the journey of finding Matt, and once Matt came on board, he really did sort of jump-start everything." 

"When you invest in a company that's exposing the hardships of startup life, you have to understand that not all of it will be pretty," says Mazzeo, who's had a hand in several early-stage tech investments. "There are a lot of holes in people's skill sets, so the goal is filling those in over time and hoping you have a team that can figure it out when they encounter something they don't know." 

Given Blumberg's knack for surrounding himself with the right people--co-founders, investors, advisers, and a supportive spouse--Mazzeo thinks the founder has enough resources to see Gimlet through. And, he admits, he was intrigued by Blumberg's vulnerability. "I think there's a pressure today, more than ever, to project your best self," Mazzeo says, "so when you're admitting you don't know an answer, I look at that as a sign of strength." 

Though Blumberg doesn't know what investors were thinking during all of those pitch meetings, he says he did feel a "certain kindredness of spirit." "That's what they're looking for," he adds, "people trying new things and who can take a new idea and execute it. They didn't see the execution [immediately], but they at least saw the attempt at documenting it. At least people would look at it and go, 'That guy's got gumption.'" 

Eventually, Blumberg learned that investors were attracted to Gimlet for their own reasons. For some, it was indeed his gumption, but for others it was something entirely different. 

Knowing Blumberg was capable of producing a world-class podcast (with Kaitlin Roberts's help) was enough to convince Groupon founder Andrew Mason to open his wallet. When asked on the show why he invested $100,000 in Gimlet, he admitted "it wasn't to make money." It was purely exploitative. "I just want you close to me for the purpose of my own business, Detour," a GPS-enabled audio service, he said. "You're good at what you do, and I'm a believer in investing in people."

Mike Quattrocki, mainly known for investing in financial technology, threw in $50,000 because he was simply a fan. And the Knight Enterprise Fund, which focuses on innovation in the media, invested in Gimlet because it aligns with its mission. 

The Entrepreneur as Storyteller

Before you read this and decide that maybe you, too, ought to broadcast your startup story in a brutally honest way, there's another side to all of this transparency that can't be overlooked. At bottom, Blumberg is a storyteller and he's building a company that promises to tell lots of compelling stories through podcasts. So the decision to use a podcast to tell his own startup story is a very savvy move. Lest you forget, while you're learning all of the ways in which Blumberg doesn't know what he's doing, the podcast proves to listeners and to backers that he is an expert in one very important area: producing podcasts.   

Blumberg himself wouldn't necessarily recommend the strategy to other entrepreneurs. "I don't think the answer is yeah, change yourself and bare all," Blumberg says. "I don't know if it's something other people should do; I don't know if it's something I should have done." 

"You don't know the potential downsides until well into the future, and this could wind up coming back to bite us in the ass," he continues. "If it is going to come, it's going to come later."

So if extreme transparency isn't for everyone, what's the lesson here? I think it's that every entrepreneur must be a good storyteller. You may not have listeners, but you have investors, customers, and employees. It's your job to make them feel as if they have a stake in your story.  

Sacca, the big-time tech investor Blumberg first pitched, offers some sage words of advice. "Human beings just want to feel helpful," he wrote in an email, and "colleagues are happiest when they know their talents are valued. So when a business leader is transparent about where help is needed, it leaves room for those around him or her to step up and contribute." 

And Gimlet just went one step further in that vein. On Monday the company announced that it was opening up the last $200,000 of the $1.5 million round it has raised so far from the likes of Lowercase Capital, Betaworks, and angel investors like Mason and Marco Arment, to listeners of StartUp podcast. And listeners responded immediately: Gimlet met the goal in a number of hours.  

Published on: Nov 11, 2014