https://youtu.be/UCy_kXJmHY0
In this episode of The Bear Roars, Dan sits down with Gregg Spiridellis, a digital media pioneer who went from Wall Street to reshaping online entertainment. Gregg co-founded JibJab, the viral content studio behind This Land and Elf Yourself, which dominated the early internet era with political satire and personalized videos. After two decades of innovation in digital storytelling, he and his brother launched StoryBots, a modern-day Sesame Street that became a Netflix hit and featured celebrity guests like Snoop Dogg, Jay Leno, and Scarlett Johansson.
Now, Gregg is turning his focus to AI and mental wellness as Founder & CEO of Moments, an AI-driven journaling platform designed to make therapy more effective.
Dan and Gregg cover:
– His leap from Goldman Sachs to launching JibJab in 1999
– Creating viral internet sensations before YouTube even existed
– How This Land catapulted them onto The Tonight Show and Sundance
– Bootstrapping through the dot-com bust and reinventing digital content
– The evolution of StoryBots and the strategy behind selling to Netflix
– Why AI-powered journaling is his next big bet with Moments
– His move to Boulder and the energy of its entrepreneurial community
Gregg’s story is a masterclass in creative entrepreneurship, adaptability, and building businesses that stand the test of time.
Learn more about Moments at https://www.getmoments.app/
🔗 Want to be a guest on The Bear Roars? To nominate a founder or to nominate yourself as a future guest, email us at contact@loudbearproductions.com.
📖 Order Dan’s Book – Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom Reserve your copy now: dan-caruso.com/book
