Outschool turned children’s enthusiasms into a marketplace for live classes. Its harder lesson has been learning how to sell freedom without making families feel trapped.
The $900 million take-private turned Cambium into a collection of specialist K-12 brands. Its latest move - merging two of the best known - reveals where the house-of-brands strategy bends.

Matt Ragland is a creator-economy builder, founder of HeyCreator, and host of The HeyCreator Show podcast. He went from camp counselor to ConvertKit employee #5, to full-time creator, building a 100,000+ audience across YouTube, newsletters, and social media. Through HeyCreator and Good People Digital, he helps creators turn their expertise into sustainable businesses via courses, communities, and newsletters. Known for radical transparency, outdoor adventures, and a systems-first approach to creative work.