Jake Hurwitz & Amir Blumenfeld Celebrate 10 Years Of Headgum

L-R: Headgum founders Jake Hurwitz & Amir Blumenfeld

Courtesy of Headgum

Jake Hurwitz and Amir Blumenfeld seem almost shocked when I bring up the fact that their podcast network, Headgum, turns 10 this month.

“We’re so busy trying to work and grow the company, that we forgot to take a moment to celebrate,” Blumenfeld says over Zoom. “Thanks for reminding us.”

Known for their fan favorite web series Jake & Amir (formerly of CollegeHumor), the bicoastal comedy duo launched the company in August 2015 alongside fellow business partner, Marty Michael. By that time, they were already two years into their now-defunct advice podcast, If I Were You, and realized they had all the resources to strike out on their own.

“We thought, ‘Wait a minute, we can have a podcast network. We know a lot of funny people and good salesmen from CollegeHumor,” notes Blumenfeld. “’We could just take all the stuff that we’ve learned in the last 10 years, create our own podcast network, and see if it takes off like Earwolf or PodcastOne.’”

“We felt like we had it under control,” echoes Hurwitz. “And we were like, ‘This is a lot easier than everybody thinks it is. We can help usher people into this new medium.’” The endgame was to create a place that was “artist-friendly and all about the creators.”

And so, Headgum was born. The impetus behind the name was a practical one — the website URL was available. According to Hurwitz, the three founders simply combined different words together until they found one they could all agree on. “‘Headgum’ was one of 40 different pitches,” he remembers. “Marty and Amir both liked it.”

Adds Blumenfeld, “It’s easy to spell, easy to say, plus [it’s] two words that have never been together, so you can’t search it and find something else.”

As for the meaning behind it, that’s up for interpretation. Amir thought of Headgum in terms of network podcasts hopefully getting stuck in listeners’ brains — like bubblegum. Jake, on the other hand, liked the idea of “minty freshness, but for your brain,” he says. “There’s kind of something in there for everybody.”

Of course, there were some growing pains for the fledgling brand, the most disruptive of which took the form of the Covid-19 pandemic. “All of the podcasts kind of had to stop recording for a few weeks [and]

all of the advertisers stopped spending money on all of the podcasts,” remembers Hurwitz, who notes that ultimate pivot to remote recordings via Zoom was, thankfully, rather painless. “It turns out that it’s super-easy and that people still love spending money on things that they hear about online. So it all worked out [in the end], but uncertainty was definitely the scariest, hardest part.”

Amir’s word of advice for any new start-up? “Make sure you have enough capital to survive a downturn in the economy. Because things are hot and then they’re not. You have to make sure you’re a little bit recession-proof, because there might be a down month or year year when you’re not making as much money as you thought you would.”

Nowadays, the founders’ biggest concern is looking after a staff of around 30 employees, which includes Vice President of Content Kaiti Moos, who was named among “Hollywood’s New Leaders” by Variety last year.

“[We want to make] sure all the people working at Headgum are creatively fulfilled and satisfied enough to keep doing a great job,” states Blumenfeld.

“They’re all individuals with hopes, dreams, goals, families. Things that happen to them outside of work,” agrees Hurwitz. “So you get wrapped up in the individuals that help the company run, which gets complicated.”

However, neither can deny the fact that hiring more people has allowed them to stop worrying about the minutiae of running a business — from managing freelancers to fixing audio interference (in other words, “all that stuff that’s we’re not good at,” admits Hurwitz) — and allow them to focus on other endeavors like their Patreon. “We make d*** and fart jokes,” Jake adds. “So as Headgum has grown and we’ve been able to give those jobs to professionals, Amir and I can go back to basics. I think our comedy has gotten better as we’ve been able to let go some of some of the responsibilities.”

“We lean on our employees a lot more now than we used to,” corroborates Blumenfeld.

When it comes to content, the duo place a companywide emphasis on seeking out passionate storytellers with a comedy background. As such, the network currently includes a wide variety of shows from major talents like Allison Williams, Ego Nwodim, David Cross, Jake Johson Adam Conover, Wayne Brady and Tig Notaro.

But fame isn’t the sole factor in what projects they decide to take on.

Says Hurwitz: “We hear a lot of pitches that are just from people who are like, ‘Everybody’s doing a podcast. I think I have to make a podcast, so I can stay relevant.’ We want to work with people that are animated, amped and excited about creating their show, because you really can’t fake it in podcasting. You’re talking for way too long to be able to phone it in.”

What’s more, the company is not owned by a larger entity, allowing it more creative freedom than the likes of Earwolf and PodcastOne, which fall under the corporate umbrellas of Sirius XM and LiveOne, respectively.

“We’re still independent, so we’re not completely beholden to a giant trillionaire company overlord,” stresses Blumenfeld. “We’re trying to hold on to the last few indie comedy vibes that are left in podcasting.”

Perhaps the most unique draw of Headgum is the way in which it “matches brands with creators in a hopefully seamless fashion,” Blumenfeld says. The all-in-one marketplace apparatus — appropriately dubbed “Gumball” — was the result of frustration with the lack of transparency during the early years of If I Were You.

“We would get ads booked, but all of the information about our show was hidden from us,” reveals Hurwitz. “[For example], we would do an ad for Casper Mattress, but didn’t know how many people were listening to it. We didn’t even know what the podcast network was getting paid. We didn’t know what we’re getting paid. Every couple months, money would just show up in our account. There was archaic bookkeeping and it was kind of like operating in the shadows. But now, podcasting has been a lot more modernized. Advertisers know what they’re buying and especially on Gumball, podcasters know what their ads are sold for, how many people they’re reaching, what the brand is paying, when they’ve gotten paid. Our idea for it was basically, ‘What if people knew how much their show was worth?’”

At the time of our call, the Headgum founders are preparing for the conclusion of their multifaceted podcast, Segments (described as “the Swiss Army Knife of shows,” it debuted in the fall of 2023), on September 15 after “a solid run,” Hurwitz says.

But that doesn’t mean they’re done speaking into the mic. Far from it.

Jake and Amir will continue to appear in Headgum originals, including the company’s namesake podcast and the highly popular Not Another D&D Podcast (or “Naddpod” for short). To give you an idea of the company’s success thus far, Naddpod — which Hurwitz co-hosts with Brian Murphy, Emily Axford, and Caldwell Tanner — was performed live at the famous Carnegie Hall to celebrate its fifth anniversary in 2023.

Impressive, to be sure. And if you can believe it, they’re just getting started, with Hurwitz promising that “the shows are getting bigger and better.”

Here’s to the next 10 years!