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Drew Houston has now been CEO of Dropbox for over 17 years. In my latest conversation, he opens up about the pivotal leadership lessons he's learned, the mistakes that shaped the company, and the true challenges of going head-to-head with big tech. We also dive into the highs and lows of fundraising, how valuations can make or break a company trajectory, and discuss the opportunities AI presents for the future of work. 0:00 Intro 0:50 AI Opportunities for Dropbox 6:03 Dropbox's AI Principles 7:58 Introducing Dropbox Dash 9:24 AI Enhancements in Search 12:39 Personal Productivity with AI 17:16 Memo-First Culture at Dropbox 22:21 Reflections on Leadership and Growth 31:27 Early Challenges and Viral Growth 48:28 Facing Fierce Competition 51:57 Strategic Shift to Collaboration 53:26 Navigating Internal Challenges 55:24 Reevaluating Productivity 1:03:13 The Birth of Dash 1:16:38 You Don't Want to Feel Like a Victim 1:30:35 Closing Thoughts and Lessons Learned Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Sam Dewees and JR Bohannon Check out Unsupervised Learning, Redpoint's AI Podcast: / @redpointai 🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast... Spotify: https://open.spotify.com/show/5WqBqDb... Google Podcasts: https://podcasts.google.com/feed/aHR0... 🎥 Subscribe on YouTube: / @theloganbartlettshow Follow on Socials 📸 Instagram - / theloganbartlettshow 🐦 Twitter - / loganbartshow 🎬 Clips on TikTok - / theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.