Leonard (Lenny's Evil Twin)
Lenny's Evil Twin's Podcast
Leonard, Lenny's evil twin, passes judgment on your startup using 5 years of Lenny's own data. Would Leonard ship it?
Author
Leonard (Lenny's Evil Twin)
Category
Podcast website
Latest episode
Jul 10, 2026
Where to listen?
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Episodes
Duolingo — Leonard would ship this 14.04.2026
They promise "free, fun, effective" learning, but their mascot literally threatens you with death memes when you skip a lesson. | They had to steal tricks from FarmVille to make people care about conjugating French verbs — that's not product-market fit, that's digital manipulation. | When your growth engine breaks, you're left with an owl making threats to teenagers. Sources from Lenny's Newslette...
Linear — Leonard would ship this 14.04.2026
They're billing themselves as purpose-built for modern teams, which is startup speak for "we couldn't compete with Jira so we added chatbots." | Linear's expensive AI-powered features risk becoming another underutilized enterprise tool that developers ignore while they go back to their trusted workflows. | You cannot cross the chasm of product-led growth because enterprise buyers need serious hand...
Slack — Leonard would ship this 14.04.2026
They turned workplace chat into a notification casino where every ping is a slot machine pull. Now they want to add Slackbot AI to coordinate your work — because what busy professionals really need is a robot scheduling their existential dread. | They're charging enterprises for AI that can't think while teams average 43 apps already. Forty-three! They built a digital filing cabinet with a chatbot...
Notion — Leonard wouldn't ship this 14.04.2026
Today's victim is Notion — the AI workspace that works for you, as long as "working" means replacing forty-seven different tools with one tool that does all forty-seven things poorly. | Notion brags about penetrating 62% of Fortune 100 but conspicuously avoids mentioning their own retention rates. | Their pricing calculator shows $4,080 in annual savings, implying high price points — but they stil...
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