Alex Blumberg of Startup Podcast on being an entrepreneur

Alex Blumberg – the Brooklyn-based creator of Startup Podcast – has over 5m listeners tuning into his shows each month. We discuss starting a business, entrepreneurial traits and not being motivated by money…

Alex Blumberg is not your average entrepreneur. His background is in broadcast journalism – he was a producer on US radio hit This American Life and co-founded Planet Money – but he left public radio to launch his own digital media company, producing high quality narrative podcasts. This company, Gimlet Media, is now worth millions.

Alongside setting up Gimlet Media, Blumberg produced StartUp Podcast: a candid documentation of his journey from journalist to entrepreneur. He records his bumbling first pitches to billionaire Silicon Valley investors, the awkward negotiations involved in finding a business partner, his joy at securing funding and the successful launch of the company.

I stumbled across StartUp Podcast while looking for ways to monetise The Early Hour. Listening to it on my morning runs, I became captivated by Blumberg’s storytelling and was so engrossed that I’d continue listening as I walked into the kitchen; ignoring my husband and hoping my daughter would stay asleep so that I could keep going with it.

So when the opportunity arose to interview Blumberg, I was just a little bit excited. But when the time came to actually Skype him in his New York offices, I was nervous. I don’t often lose my nerve like this; but then it’s not often you develop a one-sided relationship where you feel you know everything about someone’s life and they know nothing about yours – and then encounter them.

I had this idea that Blumberg would start asking me about The Early Hour, in the same way that he questions people on Startup. But he didn’t. Which made sense – I was interviewing him, after all. So I gave him my spiel and thanked him for taking the time to talk to me. I understand you must be really busy, I said. Yes, I am, he replied. And silence. Oh right, I thought – you’re going to make me work for this. But fortunately, as well as being a massive Startup fan, I’d done my research and once he realised this, he quickly warmed up.

I ask when he first thought about recording all those early conversations. You see, alongside behind-the-scenes business conversations, the type you would never normally have access to, Blumberg keeps a dialogue open with his loyal and hilariously critical wife, Nazanin, about how it’s all going. In the first episode, she laughs at his outfit choice for a business meeting: he’s wearing old trainers. And this sideline critique – of his outfit choices, name suggestions for the business, day-to-day panics – adds an invaluable human element to the recordings.

He seems to have an understanding about what people will want to listen to, which makes him the ideal person to set up a company producing podcasts, but when I ask about the business side of things, Blumberg is clearly uncomfortable. Any questions about advice for people starting out are batted away as he explains that he feels “ridiculous trying to give people advice, as I’ve been in it for two years and I’m on record as being pretty horrible at it.” But that’s where he’s wrong. Yes – he made laughable pitches, and has admitted to many a mistake along the way – but he also has this unique ability to innovate.

Podcast advertising

For instance: he revolutionised the world of podcast advertising when he decided that rather than produce ads based on stories the company gave him, he’d go into the offices himself and ask why they wanted to advertise on a podcast. The dialogue flows freely, naturally, and is funny to listen to. It brings the person, and the company, to life. And he uses these unscripted conversations to sell their product.

“It’s all about just trying new stuff,” he says, “none of this was in the plan. Literally, when I was thinking of the original podcast I imagined four episodes, called Startup, that would be a publicity stunt for the podcast company I was launching. I planned to get one on Planet Money [the show he co-founded, aired on national radio], publicising what I was doing, and to give me a little audience – and that was my main thought.”

However, after producing the first episode of Startup, he realised it was quite good. “There were real, human feelings – and I thought: this could appeal to people. I had the pitch to [billionaire investor] Chris Sacca in there. I showed it to a friend and he was like: ‘where are the ads?’ But for me, it was a vehicle to get money raised, and I took an embarrassingly long time to think about putting ads in there. That’s how good I am at business.”

Eventually, he did implement ads into Startup Podcast, which was by now gathering momentum and listeners; quickly bypassing the originally planned four episodes – and people loved them. In fact, they were so popular that listeners would rewind the adverts, if they had been distracted, to hear Blumberg interviewing a staff member at Quickbooks, rather than continuing with the narrative content. What makes the ads so good is that he clearly gets a kick out of interviewing these people.

“I love doing ad interviews, I love interviewing people in companies, finding one weird thing about them. For the first season we did Mailchimp ads. Their tagline is ‘we make hats for cats and other small animals.’ I was talking to the head of marketing and was like: what is that hat for cats thing? I asked if they actually did that; where they came up with this idea. And he said there was this woman in Indonesia who makes them, he told me the whole story, so for the next ad we ended up calling the woman and we were like: what did you think when these people came to you asking you to make hats for cats. She told us it’s enabled her to buy a house. So that was the ad.”

Money isn’t the only priority

While advertising funds his podcasts, Blumberg has taken a step back to ensure that the focus is not just on the money. “There’s a gazillion ways to make money, he says, “not that it’s easy, and I think when you start a company, you start to think: we can make money this way, this way, we should do that – you can chase money all around. So it’s been important for us to figure out: beyond money, what do we want to do. What’s our actual mission? It’s corny, but it’s helpful – you’re deciding between two different ways of making money but money isn’t the deciding factor, it’s being consistent with your philosophy and mission. This is what we’re doing, and if we can make money from it, then that’s good. Staying true to our mission and making money? That’s awesome.”

He has found this realisation freeing, the idea that he’s doing what he loves but without sacrificing his values. And this tallies with the impression that he gives throughout the Startup Podcast episodes that money is not the motivating factor for him.

“Anyone can make podcasts,” he says, “as there are zero costs. When working in public radio, I began to associate problems with innovation because of the not-for-profit structure. When you’re organising things that way you can’t amass large sums of capital but with us, if we’re profitable, we can bank that money to do big, thrilling, elaborate, exciting projects.” And so he was, in part, motivated by money; but more the freedom it gave him to innovate than in cash to take home.

One of his most exciting projects to date, he says, was the T-shirt Project, where he went around the world with a team, following the process of making t-shirts – so where the cotton is being grown, then where it’s cut and spun as yarn to where it’s manufactured. They did a Kickstarter campaign and raised over $580,000 selling these t-shirts. “All of a sudden, I had that money and the realities that that opened up for us were amazing.”

So next, they did “this gigantic web series sending teams to Bangladesh, as we were able to mobilise resources for that project.” Blumberg won an Emmy; “one of the biggest achievements of my life.” But without the funds they’d raised, they’d have had to “beg departments for money. Amazing things are possible if you have the money.”

I wonder what the final push was, to make him start his own business. “I just saw the opportunity,” he says, “I’d been working at This American life for a long time, then Planet Money, and saw that audiences were continuously growing. Every year there was double-digit growth in our audience and the excitement was growing. We launched Planet Money, thinking it wouldn’t work – but it did. So then I thought: there must be more shows to launch.”

“We did it all without any marketing. There was no money spent. It was one of those things where I was trying to figure out how to do it within NPR, within the public radio system. It was complicated for a variety of reasons. I realised if it was going to be done I’d need to raise outside money but I didn’t want to quit my job.”

Becoming an entrepreneur

Eventually, he did quit his job, realising that he wasn’t going to be able to start a company “from the comfort of my own desk in public radio.” This meant waving goodbye to a decent salary so they were both relying on Nazanin’s income. “I was really hoping I wouldn’t have to give that up but would still have a company with a stake in. It soon became clear it wasn’t going to work.”

But it also meant that he didn’t have access to the community of fans he’d built up during his time there. “I was a little panicked – basically because I was giving up a gigantic audience. I was able to reach a bunch of people through Planet Money, this American Life – that I’d no longer have access to.”

Once Startup took off, and the panic started to subside, Blumberg could return to ensuring he was home to do bath and bedtime with his kids. He puts family life before everything, and frequently relays this in the recordings. He revels in being close to his two children – Calvin, five, and Samira, three – and knowing what food they like and dislike; what they’re scared of. However, there was a period where Nazanin wasn’t involved in the betimes at all during the week, as her job meant returning home after long after they’d gone to bed.

In one episode, after Gimlet Media has launched, the couple discuss Nazanin coming to work for the company. In true Startup style, Blumberg interviews not only his wife about this possibility but also his employees, asking whether they think it’s a good idea; his wife coming to work for the company. They tell him that even if they were against it, they wouldn’t tell him and she starts working there soon after. I ask how it’s going.

“It’s working out well,” he says, “it’s weird, it’s different for both of us. For me, it’s been more unequivocally a good thing – we see each other more than we used to. And although we hardly talk at work, as we’re in meetings all day, we see each other at night. We come in to work together and often go home together. She’s just great at her job. The main awkwardness for her is that until now, her career has been built entirely on her merits and nobody was ever going to ask: do you have that position because you’re married to the person who started the company. Then she stopped that to go on to her husband’s thing. That was hard, but it’s getting better now that her job is starting to take off.”

Competition in the podcasting world

On the subject of taking off, I turn the conversation to Sarah Koenig, who Blumberg worked with on This American Life and whom he describes as an “unparalleled genius.” When they parted ways, Blumberg went off to produce Startup and Koenig went on to make Serial – a series about a teenager who is jailed for the murder of his ex girlfriend. Serial was the fastest ever podcast to reach five million downloads and I wonder if there was uncomfortable competition between the two producers.

“No,” says Blumberg, “their success has so clearly – in terms of raw numbers, impact on culture, downloads – outdone our success. It’s the biggest podcast in the history of podcasts. It’s been nothing but great for us – it brought seven million people into the world of podcasts. Then they took a break and everyone was like ‘hey, what else can we listen to’. Sarah and I are still very close and I hope we will collaborate in the future. The hope is that we’re at the very beginning of how big on-demand radio is going to get; there are 240 million radio listeners in the US alone, and the biggest single category is talk. If a lot of those people continue to migrate towards demand, there will be lots of opportunity.”

This, as I’ve come to realise from listening to Startup and having this conversation with Blumberg, is another example of his interminable optimism. You can’t imagine he’d ever see competition as a bad thing; he’s happy for others when they succeed and rather than being bitter, he imagines ways they might be able to collaborate. A strong trait in a business owner.

And again, it comes back to this question about what makes an entrepreneur successful. I remind Blumberg of a Startup episode I listened to where he is talking to Chris Sacca – the billionaire investor who eventually agrees to invest in Gimlet Media – about exactly this: what makes someone succeed. Sacca is discussing Travis Kalanick, the founder of Uber, who he also works with. After hearing about the traits that make Kalanick stand out, Blumberg sounds awkward. He asks if he has these traits, expecting a no, but Sacca says that of course he does; and that’s why he invested in him. Why are you surprised, I ask Blumberg, that people see you as having entrepreneurial flair.

“I think the thing is this,” he says, “if Travis Kalanick and I – I’ve never met the guy, no idea what he’s like or anything, no idea if we’d hit it off – but I definitely know that we’re driven by different things. Some people say that in a pejorative way, I mean that as a statement of fact. We are driven by things, and I’m realising I am driven. All entrepreneurs need to be driven and feel passionately about something – whether that’s making the most perfect set of Russian nesting dolls, or to grow fastest growing company in history of companies. There is a drive there fuelling that, and I have that. I have profound love and enthusiasm for what we’re doing.”

He goes on to explain that now, as an employer, he looks for that same drive and enthusiasm in the people he’s hiring. “We’re a network and need programmes to put on a network, we need them to be good and to grow, to have a unique voice to cut through the clutter. We need to find hosts, producers also driven by something and to share that passion. So I now feel a little bit like we’re all investing; if you have money to employ – you’re investing in something. I’m looking for passion, uniqueness.”

And there is, in his own words, what makes Blumberg – and his podcast series – so successful: passion and uniqueness. I thank him for his time, we say a hasty goodbye and he’s gone, back into his podcast world while I return to my world of the written word. And I hope that in taking heed from Blumberg’s experience, as outlined in his podcasts and our phone call, I’ll find my own company climbing the rankings in the same way that Gimlet Media is. An inspiring man, for sure.

Have you been listening to Startup Podcast, or any of the other podcasts produced by Gimlet Media? Let us know your thoughts in the comment section below…

(This was originally published in March 2016)

Portrait of Alex Blumberg (left of main image) by Samantha Appleton