I binge-listened to tech podcasts for a week, and what I learned about Silicon Valley is kind of scary

That critical mass warrants a critical response. I wanted to hear what these shows have to say about the VC mindset. They're designed to let tech investors and founders control their own narratives, free of annoying questions from journalists like me, but they also promise a kind of education — in investing, in entrepreneurship and innovation, in business. So with the help of some expert colleagues, I put together a list of about a half dozen of the most popular and influential podcasts by tech investors — from "How I Built This" and "The Pomp Podcast" to "Acquired," "All-In," "The Twenty Minute VC," and "This Week in Startups" — and put my ears toward figuring them out.

All told, I poured something like 40 hours of podcasts into my auditory cortex. I leaped around somewhat whimsically, and I did my best to ignore the uneven production values, which rendered a few episodes almost unlistenable — and this was at 1x speed. I also tried to finish episodes rather than noping out, even when they made me squawk or swear loud enough to annoy my work-from-home office-sharer. (That happened not infrequently.) 

Well, I definitely learned some learnings. And they weren't all pretty.

Learning No. 1: The hosts know their businesses

At their best, the podcasts offer some interesting insights into how tech businesses run. I'm not sure anyone should contribute to a venture fund with a lead partner who has enough spare time to make five podcasts a week. But that said, the hosts on many of these shows are investors. They're experts.

On "The A16z Podcast" (named for Andreessen Horowitz), Michael Dell, the founder of Dell Technologies, lit into the investor Carl Icahn for lying about his effort to seize control of the company. On "How I Built This," the founder of the online game platform Roblox told charming stories about making educational software for Apple's then-new Macintosh in the 1980s.

On "This Week in Startups," Jason Calacanis explained to his cohost Molly Wood that some venture-investment contracts feature a provision known as a liquidation preference, which enables the VC investors to profit even when a startup they've backed goes bust. Wood immediately put her finger on how such provisions undercut the self-image of venture capitalists as heroic risk-takers. "So this was just some magical thing VCs started writing into contracts that said: We know our jobs are risky, but we don't want them to be risky?" Yup.

I didn't hear any tips for Startups 101, like getting a meeting with an investor or building a pitch deck or a strategy memo. But I did learn a bunch of stuff I'm unlikely ever to have the opportunity to operationalize, like how to structure a marketing division, or how to think about assembling an investment portfolio as a VC. The technical descriptions from the A16z portfolio — deep unpackings of things like the cryptocurrency ethereum's move from proof-of-work to proof-of-stake, say, or TikTok's algorithmic genius — sometimes went over my head, but I can imagine their utility to engineers and founders.

Learning No. 2: The hosts don't know what they don't know

The problem is, VC podcasts don't stick to the core issues of venture capital. When they attempt to address the wider world beyond their area of expertise, things get weird.

On one episode of "This Week in Startups," explaining his philosophy of direct-to-consumer investing, Calacanis extolled the virtues of a company that makes gummy-candy vitamins, describing it as a "game changer" for getting kids to take them. Which may be true, except that healthy children rarely need supplemental vitamins.

Another example: The "All-In" podcast is designed as a friendly chat among Calacanis and his fellow investors Chamath Palihapitiya, David Sacks, and David Friedberg — "industry veterans, degenerate gamblers, and besties," as the show's ad copy puts it. At one point, Palihapitiya talked about one of his recent investments, a nutraceutical company making some sort of supplement to support healthy gut bacteria. The besties responded with a bunch of funny poop jokes, which I appreciated. But I was surprised at how little they seemed to know about nutritional research. Though the gut microbiome has been implicated in some specific disorders, like certain infections, the hosts acted as if the science of how the myriad species of bacteria in everyone's tummies are directly connected to our mental and physical health was a done deal, ready for market. It's very much not.

Or take the episode of "The Pomp Podcast" that featured Layah Heilpern, an "author, content creator, and speaker." Heilpern, who sounded like a nice person, argued that all young women wanted to be in relationships with powerful, rich men. "I'm single, and I want to get married and I want to find a masculine man," she said. Also, Donald Trump was right about being allowed to grab women by their genitals. Why? Because he was famous.

To his credit, the show's host, Anthony "Pomp" Pompliano, asked whether Heilpern thought that was a good thing. She said it was good that free speech allowed Trump to say it. No, Pomp said, not is it OK to say, but is it OK for society to be like that?

I didn't hear her response, because that was the moment I reached above my head, pulled the ejection handles, rocketed out of my fighter jet, slammed into the canopy, and died.

Learning No. 3: The hosts want us to believe what they don't know

There's a shocking amount of this kind of drivel on the tech podcasts. That's partially because the hosts fill time with whatever pops into their heads about what they read on their favorite news app that morning. But it's also because they are consciously using the shows as platforms to spread not just entrepreneurial insights, but the ideology of Silicon Valley. They made it crazy rich in whatever startup they founded or invested in, so now they think they're experts in how the world should be run. They're not just telling us how to invest. They're telling us how to think. 

On an episode of "All-In" that touched on President Joe Biden's plan to forgive more than $300 million in student-loan debt, Palihapitiya argued that it would've been better to let the free market sort everything out through existing bankruptcy protections. That's a common trope on VC podcasts, championing free enterprise over government regulation. But then one of the show's other "besties" — with four people talking, I sometimes lost track of who was saying what — went even further. Democrats want to forgive college debt, he declared, because people who go to college are far more likely to become Democrats. Forgiving student loans is part of a liberal conspiracy to support what he called "woke madrassas" that brainwash teenagers into becoming cancel-culture social-justice warriors.

Dropping out of college is a recurring theme on these podcasts. It's part of the mythos of the heroic tech founder — ditching the University of Squaresville to make billions thinking outside the box. Actually, the über-investor Marc Andreessen had the hotter take here. On "The "A16z Podcast," Michael Dell explained that he left college because the business he was running from his dorm room was making $80,000 a month, and Andreessen suggested that all the anti-college talk in Silicon Valley was just survivorship bias. No one talks about the would-be founders who quit college and fail, he pointed out. And the best-known dropouts, such as Dell, Mark Zuckerberg, and Bill Gates, already had moneymaking businesses when they quit.

Andreessen's comment made me realize that a lot of what I was hearing on these podcasts was itself a form of survivorship bias. All these profiles of companies and interviews with founders imply that even a dummy like me could learn the secrets of engineering a unicorn or disrupting a market. But that's because the podcasts, by their nature, focus almost exclusively on success stories. We're not hearing about the failures except as narrative beats in larger stories of triumph.

Learning No. 4: Rich is more important than good

When journalists do one-on-one interviews, they're supposed to deploy tough questions. The hosts on tech podcasts rarely do that. One exception is Guy Raz, the host of "How I Built This," who clearly does a deep research dive for his hours-long interviews. His episode with David Baszucki, the founder of Roblox, explored decades of tech culture and innovation through the lens of Baszucki's career. This is what a good tech podcast should do: Use access to the best and most successful investors and innovators to illuminate the way Silicon Valley works.

But VC podcasts almost never ask the central question involved in their work: What is the definition of "success"? If success is just something that is popular and makes money, which is the overall vibe on these podcasts, then Roblox is an unarguable success. But if success is something that contributes to societal good — something that meets Silicon Valley's self-professed value of making the world a better place — then maybe Raz should have pushed Baszucki about Roblox's issues with encouraging children to spend money online and serving as a playground for actual real, live Nazis.

Rivian, the electric-truck maker, made a big splash a few years ago with its Tesla-competing high-end SUV and pickup. So props to RJ Scaringe, Rivian's founder, for telling Raz that he used to lie awake at night wondering whether his startup deserved to exist — that he wanted to have a company that did good for the world. He was the only founder I heard explicitly frame that as a metric for success, alongside revenue and growth. (Over on "This Week in Startups," to be fair, Wood explicitly invests in tech to help fix the climate.)

But as good as Raz is, he didn't push Scaringe very hard on whether his obviously well-intentioned company's goals even made sense. Are large electric trucks really the right way to address road congestion, highway deaths, and the climate crisis? By almost any measure, they are not. But that's not what matters in the world of tech podcasts. For all of Silicon Valley's self-mythologizing around doing good in the world, the only thing that founders and investors seem to care about on these shows is doing good for themselves.

Learning No. 5: The secret of successful startups is there is no secret

In his introductions, Raz is careful to lay out one or two core lessons from his interviews. The vibe is, "Here's what we can learn about business from these titans of industry." But I'm not confident that the lessons Raz lays out are the things that actually made these companies work. Raz prefaced his interview with the two founders of the Bored Ape Yacht Club — valuation: $4 billion! — by explaining that neither Wylie Aronow nor Greg Solano were technical at all. They were creative-writing majors who got interested in crypto and recruited a couple of other pals to handle the back end. It was their genius for storytelling, Raz seemed to suggest, not coding, that made their idea soar.

Both Aronow and Solano had thoughts about why personality-heavy pictures of cartoon apes might turn into a multibillion-dollar brand without an actual product. "You get to Disney-levels of empathy and belovedness for a brand much sooner when somebody can own a little piece of Mickey Mouse," Solano said. But no matter how hard Raz pushed — and he tried — he couldn't get either man to articulate what their creative insight was. They didn't seem to have any idea about why they'd been successful when so many other NFTs had failed. The main lesson of their success, if there was one, was "be lucky."

The same thing happened when Raz interviewed Sarah Kauss, the founder of the S'well brand of insulated water bottles. At the top, Raz proposed that her signal insight had been bringing sophisticated design to, well, thermoses. Which, as an explanation for tech-industry success, is a bit off message. It's hard to see how "make the bottle elegant" reflects any of the elements that investors on these shows say they look for: disruptive innovation, intrinsic intellectual property, a business with a moat around it that keeps major players from stealing it. The bottles are just … nice. They got popular. S'well became a monster brand. In short: business as usual.

Learning No. 6: The valorization of the asshole

On that "A16z" podcast with Michael Dell, the hosts — one of whom had actually worked with Dell — spent quite a bit of time talking about his reputation as being a generally nice guy. Dell himself talked about firing a relatively high-level person for not being a team player. But he also said that to succeed in business, "You have to be a deviant and mischievous and a rule breaker, and that's not for everyone."

So, fine, that's not necessarily a will to power. But lots of these shows have a creepy, almost Randian undercurrent that suggests that only a certain kind of person can really build a multizillion-dollar business — someone of unusually vast creativity and intellect. On another "A16z podcast" episode, a veteran of Amazon, Hulu, and Oculus named Eugene Wei made a revealing comment: "The truth is, most people can't originate ideas," he said. That's a striking opinion to have about one's fellow humans, as if everyone else is a non-player character.

One episode of "This Week in Startups" opened with an incredulous discussion of retiring Disney CEO Bob Iger's decision to go work for a venture-capital firm owned by members of the Kushner family. Wood and Calacanis agreed on how much they admired Iger for his brains and "high EQ." He's famously smooth. But then Calacanis weighed in on how Silicon Valley thinks about niceness. Lots of investors, he said, view the founders they work with on a two-by-two grid: likable/unlikable on one axis, and high aptitude/low aptitude on the other. The most sought-after founders, he explained, are in the unlikable/high aptitude quadrant, because they make the most money. 

Assholery, in the Silicon Valley mindset, is a key to success. It's also … bad? If I sound naive in suggesting it's better for people to be kind to one another, try it this way: When bosses act like asses, they prevent those who work for them from achieving their potential, and maybe making their numbers. Anyone who treats their fellow humans the way Steve Jobs did is ignoring all the gentle successes where people got rich and made good stuff. Valorizing assholes is just another form of survivorship bias. You think jerks are good for business because jerks are all you've known.

Learning No. 7: Bigger crowds don't always mean more wisdom

The tech-investment podcast universe feels like an invasive lily pad taking over and choking what was, admittedly, already a swamp. As the internet has taught us, high-quality information is usually behind a paywall. Tech podcasts are free. And long. "All-In" has nearly 100 episodes, all longer than an hour. "Acquired" is in season 11; its current episode on Amazon is more than four hours long. "The Pomp Podcast" routinely breaks the two-hour barrier and has posted more than 1,000 episodes. 

This is a vast amount of content, a Mjolnir-strength whack to the information ecosystem. And it's the sheer scale of the podcasts, ironically, that makes them so dumb. The morning-chat-show structure forces the hosts to talk about whatever is in the news, pushing them to apply the rules of their narrow lanes across the entire information superhighway. The overly friendly interview structure provides no countervailing information and few hard questions. So the basic ideology of Silicon Valley — money is the only metric, being a jerk is fine, don't know what you don't need to — gets pushed into every corner like grout. The philosophy drowns out, talks over, and interrupts all the other ones. With repetition and reinforcement, it starts to feel true.

Here's how I know: It worked on me. At about hour 20, I was starting to question whether I would, in fact, be man enough to start my own business instead of being a mere soyboy cog. By hour 30 I was clicking through that site that lets people invest their retirement funds in crypto and asking my partner whether it might make sense to throw a small, risk-sensible percentage of our 401(k) at it. I could feel my intuitive map getting rewritten. Government is always bad, the market solves everything, clever investment is a real job even if you don't produce anything except money. I should start a company, grow fast, get a big exit, buy a house in Atherton and spend my leisure time urging people not to go to college and fighting the construction of protected bike lanes and multifamily housing.

I shook off the impulse; I remain an un-entrepreneurial swiller of lattes, lacking the risk-taking bravado (and large vacation home) of a founder. But after 40 hours of listening to tech podcasts, I feel kind of bad about it.

Adam Rogers is a senior correspondent at Insider.