Short answers, pulled from the story.
Roll20 was founded by three college roommates Riley Dutton, Nolan Jones, and Richard Zayas. The platform officially opened to the public in September 2012 after a successful Kickstarter campaign in the spring of 2012.
By mid-2022, Roll20 had more than 10 million users after doubling from five million users in almost two years. The company tripled in size from 20 or 25 employees to nearly 60 under CEO Ankit Lal who took the helm in February 2022.
In February 2019, TechCrunch reported that Roll20 databases were hacked along with those of eight other companies. The information of over four million users was posted for sale on a dark web marketplace exposing vulnerabilities of the browser-based platform.
Roll20 acquired the digital tabletop role-playing toolset company Demiplane in June 2024. The combination of the Roll20 virtual tabletop and the Demiplane character sheet ecosystem allows users to build their first character and get into their first game with cross-platform access.
In July 2021, Roll20 increased their subscription costs for the first time with the annual Plus tier rising from 49.99 dollars to 59.99 dollars. The annual Pro tier increased from 99.99 dollars to 109.99 dollars while the free version restricts users to 100 megabytes for uploadable assets.