How Evernote Bootstrapped Then Nearly Died Then Survived

Episode 44 of Bootstrapped Business with Fexingo: Self-Funded Founders, Profit-First Growth, and Lean Operations. Lucas and Luna unpack Evernote's wild ride — from a bootstrapped note-taking app with a cult following to near-collapse after taking venture capital, and its recent turnaround under new leadership. They focus on CEO Ian Small's 2023 restructuring: cutting 87 products down to 3, laying off 47% of staff, and refocusing on paying users. As of June 2026, Evernote is cash-flow positive again with 12 million active users and $28 million in annual recurring revenue. The episode asks: can a once-bootstrapped company ever return to its profit-first roots after VC money changes everything? #Evernote #Bootstrapping #IanSmall #VentureCapital #ProfitFirst #SaaS #Turnaround #LeanOperations #NoteTaking #BusinessGrowth #CashFlowPositive #Restructuring #Fexingo #BusinessPodcast #BootstrappedBusiness #SaaSStories #StartupLessons #SelfFunded Keep every episode free: buymeacoffee.com/fexingo