[7][8] In August 2011, Skillshare raised $3.1 million in Series A funding led by Union Square Ventures and Spark Capital.

[11] Skillshare held the Penny Conference in April 2012, a one-day discussion on the current educational system and how to reform it,[6][12] with Michael Karnjanaprakorn, Codecademy’s co-founder Zach Sims, and Pencils of Promise founder Adam Braun as speakers.

[16] Skillshare collaborated with Levi's to launch the School of MakeOurMark in October 2013, focusing on individual creativity with courses in photography, tattooing, and various forms of illustration.

[19] Later that year, the company announced a new open platform, where anyone could be a course instructor, and a free membership option to watch a limited amount of class content each month.

[24] Skillshare organizes courses in advertising, business, design, fashion and style, film and video, food and drink, music, photography, gaming, technology, and writing and publishing.