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?”
“We uniquely can tell some of these stories. So it’s a very strong differentiator, demonstrating that Sequioa can give far more than capital,” he says, adding that the firm views itself a “company-building” enterprise rather than a cadre of check-writers. (Botha revealed that the second season of his podcast is in the pipeline.)
For others, like Joubin Mirzadegan, podcasting began as a way to build relationships and learn from leaders. Mirzadegan, an operating partner at Kleiner Perkins, is behind Grit, a four-year-old interview podcast featuring technology company executives (only about one in 10 guests hail from Kleiner Perkins–backed companies, he tells me).
“The reason why it happened this way was because I was pretty young to be in this role, so I didn’t have the 30 years of experience to go draw from in my career to be able to advise our portfolio,” he says. “I thought this was an interesting way to just get to know these people.”
Not every firm has the patience for the yearslong slog required to cut through the Wayne’s World–for–investors clutter. In 2022, Khosla tried its hand at the medium by hiring Kara Miller, a public radio veteran based in Boston. Together, Khosla and Miller produced a few dozen episodes of Instigators of Change, which tapped academics, authors, VCs, and founders to discuss trends in the technology space. “People had heard of Khosla, I would say, but we weren’t in the forefront,” Daver, the chief marketing officer, says of the decision to launch the podcast.
Today, that RSS feed now sits dormant because Khosla decided to sunset the project. Daver explained that the effort required to make a stand-out podcast wasn’t worth the investment. Instead, she now tries to highlight the firm on better-established podcasts. “Starting a podcast today is an uphill battle, because you’re competing with All-In, you’re competing with Reid [Hoffman],” she says. “Why would I want to compete with them? Why don’t I just figure out a way to get on them?”
It’s a recipe that has worked for the once camera-shy Jared Kushner, who has appeared on podcasts like All-In and MIT research scientist Lex Fridman’s show in recent months (think: more friendly fireside chats, less Kara Swisher vs. Mark Zuckerberg grillings). The chitchats resulted in numerous companies and investors contacting Affinity Partners, his $3 billion firm, which boosted its deal flow, Kushner told The New York Times.
Still, in a certain strand of tech podcasting, a select few investors can’t resist the allure of becoming the Joe Rogan of software. If Silicon Valley engineers practice the “rest and vest” mentality, these high-profile Silicon Valley company pickers practice the “opine and shine” lifestyle. David Sacks, a software investor and All-In cohost, has appeared on Fox Business to discuss the federal budget. His rise to fame coincides with the celebritization of venture capital, a historically unglamorous business.
“I think what you’re seeing is very sharp, smart VCs with their own sometimes controversial points of view transcending their little walled gardens of Sand Hill Road and going and becoming more mainstream media figures,” explained investor and podcaster Kevin Rose. “There’s just a handful of people who have been able to say, ‘Yes, I’m a VC, yes, I put dollars into companies, but I can actually weigh in on a whole variety of topics and add value and become more seen as a thought leader.’”
Silicon Valley’s audio fever comes at a moment in which many VC types are souring on news outlets, believing reporters to be overly critical of technology’s possibilities. In 2021, Andreessen Horowitz, which had invested in onetime digital media darling BuzzFeed, proposed a solution by starting its own technology publication, Future. Although Andreessen wound down the publication the next year after it struggled to find an audience, firms’ desire to control their own message remains. When I ask Botha about VC firms eschewing media gatekeepers, he tells me that building a direct relationship with audiences is important for the industry. “In general, you don’t want to have intermediaries,” he says. “That applies to any business.”
Insight Partners, the New York–based investment firm, quietly bought the New Stack, a digital news company targeting software developers, a few years ago. Martell—who, together with Crivici-Kramer, sold a previous newsletter and podcast business to the trading platform Robinhood—says he believes more venture firms will buy small media companies as opposed to building a following from scratch, which can be a near-Herculean feat.
But for now, the venture capitalist archetype still includes donning headphones and hitting record. “The hedge fund guys have their Gulfstreams and their puffy vests and whatever else they tend to do,” says jack-of-all-trades Bradley Tusk, who runs a nine-figure venture firm, as well as an RSS feed. “We’ve got podcasts.”
Correction: An earlier version of this piece incorrectly identified software investor David Sacks as having written for Foreign Affairs. Essays in Foreign Affairs have been written by a different David Sacks.
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