A New Podcast: Dead Cat

In the first episode, we talk with Rippling CEO Parker Conrad.

Even reporters realize that there’s an inherent artificiality to tech news. There are certain conventions of the view-from-nowhere style that can obscure the truth more than they reveal it.

As a personal antidote to that, I’ve had a long-running private Signal message thread with my reporter friends Tom Dotan and Katie Benner where we try to debate the merits of a story and discuss why its sourcing probably led it to come out looking how it does. It’s a sort of meta-look at the news that considers how the story gets told and why.

No one wants to read a publication filled with that kind of journalistic navel-gazing, and I don’t want to write one. But in a podcast, I can shoot the shit with my friends and interesting people in tech, and tackle those meta themes and others as we examine the tech media landscape.

So we’re starting a podcast. Tom is a tech reporter at Insider and previously hosted The Information’s 411. (So unlike me, he knows what he’s doing.)

As her schedule allows, Katie is going to be a regular guest. She has a busy day job as the New York Times’ Justice Department reporter.

Sometimes the podcast will be just us. Sometimes we’ll have guests. The format is going to emerge as we make this thing. There are plenty of podcasts out there doing weekly interviews with tech luminaries who pitch their businesses and, often, themselves. This isn’t that.

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We’ve already recorded a lively first episode.

We talked with Rippling CEO Parker Conrad.

There are few stories over the years that have fascinated Tom, Katie, and me as much as Zenefits. The saga pitted Andreessen Horowitz and David Sacks against startup founder Parker Conrad. The media (including all three of us) pilloried Conrad. I co-wrote a story titled Zenefits Was the Perfect Startup. Then It Self-Disrupted. Our friend Rolfe Winkler at the Wall Street Journal captured the zeitgeist with his story headlined Zenefits Once Told Employees: No Sex in Stairwells.

Always an innovator, Conrad was early to this tech cycle’s startup implosion story. But I’ve never really believed that the insurance rules that Zenefits violated were that important. Are regulations about who can sell health insurance anything more than a protection racket for incumbents? Whatever you think about those rules, there’s no question that Zenefits captured Silicon Valley’s attention because of the sheer spectacle. A highly valued startup, backed by Fidelity and TPG, was suddenly blowing up.

Going through that crucible has given Conrad a battle-tested perspective on Silicon Valley. From his perch he diagnoses a parasitic media-VC symbiosis.

I always see a lot of significance in my firsts. I launched this newsletter with a broadside against Sequoia, examining the political and organizational complications with the firm’s stake in China. Now, with this first podcast episode I’m poking at a big premise of this newsletter: That VCs serve as the stewards of Silicon Valley.

I hope you’ll give it a listen.

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