Drew Houston on Steve Jobs' Attempt to Acquire Dropbox

The Invitation to Apple

• 💡 Drew Houston and Arash Ferdowsi were summoned to meet Steve Jobs in 2009, prior to Apple's iCloud launch in 2011.
• 🔍 The meeting occurred after Apple's MobileMe team expressed confusion about Dropbox's user interface, leading to discussions between engineering and their corporate development (M&A) team.
• 📌 Houston, a long-time admirer of Jobs' work, found the experience intimidating due to Jobs' reputation for being either charming or difficult.

Steve Jobs' Acquisition Pitch

• 👏 Jobs initially greeted them warmly, stating, "You guys have built a great product," which Houston considered a significant personal achievement.
• 💼 The formal part of the meeting was brief, with Jobs pitching them to "throw in with Apple" and join the company, emphasizing Apple's resources.
• 🚫 Houston's primary goal was to avoid angering Jobs while politely declining the offer, aiming for no follow-up from Apple.

Feature vs. Product Debate

• 💬 Houston expressed his desire to continue building Dropbox as an independent company, citing the enjoyment of the process.
• ⚔️ Jobs then became more assertive, arguing that Dropbox was a "feature not a product" and lacked control over distribution and operating systems.
• 💡 Houston countered that the incompatibility between different operating systems (like Android and Mac OS) precisely necessitated a common layer like Dropbox.

The Decision to Remain Independent

• ⚠️ Jobs concluded the meeting by stating Apple would "build our own thing and kill you," a direct threat to Dropbox's future.
• 💰 Houston was unconcerned by potential dollar amounts for an acquisition, as he was focused on Dropbox's rapid growth and independent trajectory.
• 🚀 He believed that if Dropbox continued to "10x every year," its value would only increase, making an acquisition less appealing.

Jobs' Perspective on Apple's Return

• 🗣️ After the formal meeting, Jobs stayed to discuss his return to Apple in 1997.
• 📊 He expressed bewilderment at how Apple, despite generating $7 billion in annual revenue, was still losing a billion dollars a year at that time.
• 🧠 Jobs shared insights about that period, much of which has been publicly reported.