

Fireside Chat with Otis Gordon, cofounder of Checkpoint Pictures (acquired)
Join us for an intimate fireside chat with Otis Gordon, cofounder of Checkpoint Pictures! Otis graduated from the University of Chicago in 2024, where he earned degrees in Fine Art, Psychology, and Neuroscience. During college, he started building Checkpoint Pictures, an innovative receipt-based photo booth that has captured memories for over 3,500 users across NYC, LA, Chicago (including right here at the MAAD center!), and beyond. At UChicago, Otis iterated many versions of the photo booth and worked on it even after graduating.
Checkpoint Pictures was recently acquired by Future Primitive, an onchain product studio that builds startups, projects, and primitives for decentralized communities backed by a16z. Come hang out and hear Otis share his journey—how he experimented with different versions of the Checkpoint photobooth, what strategies clicked (and what didn't), what motivated him to keep going, and the inside story of how his startup caught the eye of a major player.
Bring your questions, curiosity, and good vibes—it's going to be a fun, relaxed conversation hosted by Windy Ventures' own Colin Yuan. See you there!