Jason Calacanis is known for a few things. First, he is an early-stage venture capitalist who bet big on unicorns like Uber and Robinhood. Others may know him as a member of Elon Musk’s inner circle, who joined the X owner’s war room during the early days of Musk’s reign. But over the last few years, Calacanis has also become one of the technology industry’s most recognizable talking heads, thanks to his two popular podcasts, This Week in Startups and All-In. “If a VC is passionate about having great conversations,” he says of audio, “it’s an excellent medium for building relationships and letting the world know your thoughts.”
Calacanis first started gabbing behind a mic in 2009, long before podcasting would eventually make hosts like Alex Cooper and Joe Rogan early-stage-investor-in-Uber-level rich. Since then, the Brooklyn-born entrepreneur has penned a book on angel investing, organized technology conferences, and amassed a following of listeners in the millions. Last year, after Calacanis set out to raise his fourth fund for Launch, his early-stage venture firm, he highlighted just how critical those podcasts were to his firm’s start-up sourcing. “The podcasts are the top response we receive when asking founders how they found out about our firm,” Launch’s fundraising materials read.
Launch is far from the only firm hoping to cash in on podcast plays. In recent years, numerous heavy-hitters on Sand Hill Road have set up RSS feeds in the hopes of reaching the eardrums of the next billionaire founder. Whereas investors once had to woo founders with tasting menu dinners or trips on their private jets, they can now do so over Spotify. And, because “deal flow is destiny” in the venture community, as Calacanis notes, any tool to burnish investors’ brands is seen as mission critical. “The product becomes the people,” Shernaz Daver, the chief marketing officer at Khosla Ventures, says of venture firms. “It’s a very different way of looking at the world.”
Today, capital allocators like Andreessen Horowitz, Sequoia Capital, Accel, and Kleiner Perkins all boast their own audio series with varying degrees of success. (Andreessen has two Top 50 technology podcasts on Spotify). Outside of venture companies, Midas-touch investors like Reid Hoffman, Brad Gerstner, and Bill Gurley have launched shows to much fanfare, while plenty of others talk, seemingly, into the void. To some, hosting podcasts feels as popular among venture capitalists as happy hour at the Rosewood on Sand Hill Road.
“If Jack and I had a dime every time that a venture capitalist mentioned to us that they were launching a podcast,” jokes Nick Martell, who cohosts The Best One Yet, a business news podcast, alongside Jack Crivici-Kramer, “we’d have raised an Andreessen fund by now.”
Before Marc Andreessen and Ben Horowitz formed their eponymous venture firm in 2009, technology’s top investment funds were known (if they were even known at all) for being media-averse. (At one point, Sequoia reportedly turned away money from public institutions so prying journalists couldn’t dig up their financials). As the disruptors, Andreessen Horowitz took a markedly different approach when it came to publicity.
In Andreessen’s previous career as cofounder of the browser Netscape, he landed on the cover of Time in 1996, perched barefoot in rolled-up jeans upon a throne. That photo, naked toes and all, helped cement a new kind of A-lister: the dot-com wunderkind. Ben Gilbert, who cohosts the PhD-level-researched podcast Acquired, believes this iconic image shaped Andreessen Horowitz’s radical strategy a decade-plus later to embrace owned and earned media, as evidenced by PR whiz Margit Wennmachers joining the firm as a partner a year into its existence.
“I haven’t talked to Marc about this, but I have to imagine that that was so formative of ‘Whoa, you really can own a movement, own a conversation, own an era by doing a media blitz,’” he tells me of the Time cover. “No other VC had a career like that before Marc to drill in that this could be a successful strategy.”
These days, feeds have supplanted the magazine cover, opening the floodgates for fledgling angels to secure funding and enter coveted deals by dint of their public persona. Harry Stebbings—the 20-something host of the The Twenty Minute VC, in which Stebbings interviews investors—raised $140 million for his funds off of the success of his podcast. Gilbert—whose podcast, which he hosts with David Rosenthal, has developed a cult following among tech executives—tells me their show has transformed their ability to invest in attractive deals.
“Even though we didn’t start it with the intention of it being our investing edge, it is now, by far, the most important thing for David and I as investors,” Gilbert says. “When I was a very young junior VC, I’d be begging for meetings. Now there’s close to three quarters of a million people that listen to every episode and I no longer need to ever do any cold outreach saying, ‘Hi, you don’t know me, but I’m interested in your company.’”
Even mega-funds, despite having nothing to prove, are jumping on the audio bandwagon. Take Sequoia, which has over $56 billion under management, recently debuting Crucible Moments, a slickly produced podcast exploring strategic decisions during a founder’s journey. Roelof Botha, the senior steward of the firm who also hosts the podcast, told me he wanted to go deep on fork-in-the-road-esque moments that shape companies’ trajectories. Botha says the show’s name, a term coined by his colleague Jim Goetz, has been part of the firm’s internal vernacular for two decades.
“It’s almost like the case studies you get to read in business school,” the Stanford Graduate School of Business alum says of the podcast, which has featured Sequoia success stories like Nvidia and PayPal, as well as duds like Jawbone. “Wouldn’t it be great to understand what was going on at Airbnb as COVID struck? What was Square thinking as they were launching a consumer service when the business had been a [small- and medium-sized businesses] service?”
