Exploring Talent, Connection, and Collaboration in the Early Web

Kara is a journalist who has covered the business of the Internet since 1994. She was the cofounder and editor-at-large of Recode, and she's worked for the NYT, the WaPo, and the WSJ. She’s now the host of the podcast “On with Kara Swisher” and the co-host of the “Pivot” podcast with Scott Galloway, both distributed by New York Magazine. Her new memoir is Burn Book: A Tech Love Story. It’s a fun read, and it was good to hang out with her again after many years. We were both web pioneers and it’s good to remember those days of the blogosphere. And we get fiery at times.

For two clips of our convo — debating how woke the MSM really is, and how readers are smarter than journalists — pop over to our YouTube page. Other topics: Kara’s rough childhood on Long Island; losing her dad at an early age and contending with a bad stepdad; her military family and her interest in serving; how DADT made things worse for gays; being an AIDS quilt folder; lesbian tropes; our mutual dislike of Pride parades; her fearlessness as a young reporter; The McLaughlin Group; the condescension of legacy media; tycoons who buy media outlets; Jeff Bezos; Marty Peretz; Friendster, Zip2 and Suck.com; how Facebook was seen as a savior for media; how trolls are chagrined when you talk to them; how Zuckerberg is “lovely but awkward” in person; Bill Gates; Peter Thiel; how gay hookups drove the early internet; how the apps kill serendipity; the power of podcasts for community; how the right innovated direct mail and talk radio; Obama’s pioneering with web outreach; how Twitter made January 6 (and Trump himself) possible; Kara watching every single episode of The Apprentice; how Trump’s act is getting stale; how social media is not a good business model; Elon Musk; buying Twitter to “make him more interesting at parties”; the Walter Isaacson bio; Elon’s vile tweets on Paul Pelosi; his trans daughter; ketamine; Mark Cuban on DEI; abortion in the 2024 election; how social media is fracturing and losing appeal with Gen Z; the decline of cable news; the disinfo on unarmed black men killed by cops; how BLM led to more black lives lost; the grievance-industrial-complex of the right; how its reactionaries just want to “burn s**t down”; why Kara is a China hawk; why she disagrees with Jon Haidt; the TikTok ban; the Twitter Files; Hunter’s penis; Tipper Gore and dirty lyrics; and how Kara counsels her four kids about social media and porn.

Browse the Dishcast archive for an episode you might enjoy (the first 102 are free in their entirety — subscribe to get everything else). Coming up: Adam Moss on the artistic process, Johann Hari on Ozempic, Nellie Bowles on the woke revolution, Noah Smith on the economy, George Will on Trump and conservatism, Bill Maher on everything, and the great Van Jones! Send any guest recs, dissents, and other comments to dish@andrewsullivan.com.