Tech Podcasts: AI, Product Leadership & Industry Insights | 2024 Updates
Stewart Butterfield, co-founder of Slack and Flickr, recently appeared on Lenny Rachitsky’s podcast to discuss the mental models that underpinned his success building influential internet products. The conversation, recorded November 20, 2025, and published on multiple platforms including Apple Podcasts and Spotify, covered a range of topics from “utility curves” to “hyper-realistic work-like activities.”
Butterfield’s insights, shared in a “rare podcast appearance” following the sale of Slack to Salesforce, focus on product development and leadership principles. The discussion delved into concepts like “the owner’s delusion,” a phenomenon where creators overestimate the appeal of their own work, and the importance of understanding how users perceive value – represented by “utility curves.”
The podcast also explored practical product strategies, including the principle of “Don’t make me think,” advocating for intuitive design, and the caution against attempting to be all things to all people, summarized as “We don’t sell saddles here.” Butterfield also discussed the concept of “tilting your umbrella,” a metaphor for adapting to changing circumstances, and offered perspectives on when a company should consider pivoting its strategy.
The appearance on Lenny’s Podcast follows Butterfield’s shift in focus towards family, philanthropy, and creative projects after the acquisition of Slack. The podcast episode is part of a series featuring interviews with prominent figures in the tech industry, aiming to provide actionable advice for product builders and leaders. Lenny’s Podcast also recently featured Jessica Fain, a product leader at Webflow and former Chief of Staff at Slack, discussing the importance of influence in an age of artificial intelligence.
Other podcasts currently attracting attention include Access, hosted by Alex Heath and Ellis Hamburger, which covers the tech industry’s internal conversations; Big Technology Podcast, offering behind-the-scenes insights; Hard Fork, examining the evolving tech landscape; The Social Radars, featuring interviews with successful Silicon Valley founders; and Tools and Weapons with Brad Smith, exploring the intersection of technology and society.
As of March 23, 2026, Salesforce has not publicly commented on any strategic shifts related to Slack following Butterfield’s departure. No further public appearances by Butterfield have been scheduled.