Our first guest is Yousuf Khan, who discusses what he learned on his journey from “accidental CIO” at companies like Automation Anywhere, Moveworks, and Pure Storage to “unconventional VC” at Ridge Ventures.

• Going from CIO to VC (2:22)
• Would you have hired your younger self? (4:03)
• The value of candid conversations (7:10)
• Good vs. Bad relationships with startups (9:10)
• Working with companies like Slack, Smartsheet, & Oomnitza (12:17)
• How do you decide which startups to bet on? (14:33)

Mentions: Brendan Baker, Alex Rosen, Arthur Lozinski