Sheila Gulati grew up literally inside her parents' software startup doing every job from duplicating disks to writing manuals, giving her unusually deep lifelong immersion in enterprise software that she later combined with her Microsoft Azure leadership experience to become a specialist operator-turned-investor at Tola Capital. She takes a highly scenario-driven approach to AI investing, going very deep on specific enterprise use cases and focusing on where startups can win relative to mega-cap platform strategies rather than backing broad AI stories.