E954 Gentry Underwood, Navigator: AI asst for mtgs, sold Mailbox to Dropbox $100M, SV SaaS burnout

Gentry Underwood, Co-founder & CEO of Navigator, demos new AI assistant for meeting efficiency & teamwork, insights from selling Mailbox to Dropbox for $100M just 37 days after launching, SaaS burnout in SV, desktop v. mobile cognition, mastering form emerging from functionality

4:20 Why Gentry built Mailbox
16:25 Optimizing email for mobile
24:36 Best aesthetic designs in tech today
45:15 Origins of Navigator
48:52 Gentry demos Navigator
1:03:54 Importance of seating arrangements in board meetings

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