'Give Time To Take Risks': Every's CEO On AI And Trying New Tools
The tip, shared on the deck of a cruise ship in the Hudson, comes Richard Branson approved. Plus: Upstarts readers can submit Qs for Klarna's CEO.
The Upshot
“If you need a push, this Dan Shipper episode with Lenny Rachitsky should be required listening for anyone in media.”
This line, from a roundup of takes on the state of the media industry compiled anonymously by Feed Me founder and Substack queen Emily Sundberg last month, served as our starting-off point as Upstarts interviewed Shipper on the deck of a cruise ship docked in the Hudson River this week.
We were at an event for founders, investors and media types hosted by venture firm M13, serving as the warm-up act for Virgin Voyages’ larger-than-life leader, Sir Richard Branson, who listened in.
Thankfully, Shipper is highly qualified to talk about tinkering with AI. As a publication, his startup Every reaches about 100,000 readers with practical tips on how to use new AI models and tools and other sector commentary; as a software business, Every consults companies on such adoption, and has shipped six products — Cora, an AI email app; Spiral, an AI ghost writer; and Sparkle, an AI file organizer — with just a team of 15.
“Everybody at Every is using AI tools all the time,” Shipper says. But everyone at Every is also a writer, too. And it was Shipper’s advice on how to creatively balance the two — finding the gaps to think about the future — that resonated with Branson most.
Typically, Upstarts’ paid edition focuses on exclusive interviews with elusive tech leaders, like Esri founder Jack Dangermond; in-depth analysis, like a look at a stealthy U.K. defense startup; or high-impact scoops, like a team quietly leaving OpenAI to launch a reinforcement learning lab, or Meta holding secret talks with Midjourney.
For this issue, we’re going to try something different: sharing some of the highlights of our recent chats with Shipper, both this week and earlier this summer for an episode of The GP’s podcast The General, as well as from another chat we participated in from another bonkers location — this time, a shuttered power plant being turned into a nature and community hub — with longtime media exec turned Substacker John Ellis and popular YouTube creator William Osman.
We’ll also peel the curtain back a little on Upstarts’ own (limited) experimentation with AI tools so far, and why we believe that a human community, like the one we’re building here with you, is more important than ever.Our current AI state of play, and how to pose a question, are below.
But first, in the spirit of the mailbag that kicked this off: we are excited to offer Upstarts reader a chance to pose a question to Klarna CEO Sebastian Siemiatkowski to be posed by editor Alex Konrad in an upcoming video interview. To submit a question, fill out this form.