Ann Winblad is a Silicon Valley legend who bootstrapped her first software company with $500 borrowed from her brother, sold it for $15 million, then co-founded the world's first venture capital firm exclusively dedicated to software in 1989. Over 30+ years at Hummer Winblad Venture Partners, she backed 160+ enterprise software companies - including first-institutional-investor bets on MuleSoft (acquired by Salesforce for $6.5B) and Omniture (acquired by Adobe for $1.8B) - while becoming the most influential female venture capitalist of her generation.
Andrew Wilkinson is a Canadian entrepreneur, investor, and author who built Tiny - a publicly traded holding company (TSX: TINY) often called 'the Berkshire Hathaway of the internet' - from a one-man design agency he started with $200 at age 20. Having dropped out of university after less than a year, he transformed a $6.50/hour barista gig into a billion-dollar empire of 32+ internet businesses including Dribbble, AeroPress, Letterboxd, and Serato. His 2024 memoir 'Never Enough: From Barista to Billionaire' became a USA Today bestseller and candidly explores why wealth didn't bring happiness, his ADHD diagnosis, and his commitment to giving away most of his fortune through the Giving Pledge.