Harvard in Tech Spotlight: James Ruben, founder and CEO of Hellosaurus (Y Combinator S20)

Jess Li
Harvard in Tech
Published in
3 min readMar 18, 2021


James Ruben, founder and CEO of Hellosaurus

I spoke with James Ruben, founder and CEO of Hellosaurus (Y Combinator S20), a media company reinventing children’s programming for touchscreen audiences.

Prior to founding Hellosaurus, James was head of product at HQ Trivia, where he learned a lot about the interactive video world. In particular, he learned that creating a successful interactive video software company required two components: content for which interaction was a fundamental component and a market full of content creators who could serve as the production arm. Kids media was the perfect fit on both of those dimensions: kids shows have always turned to the screen and asked the kid to participate and a series of content moderation and policy changes at YouTube have pushed many kids media creators on YouTube to look for alternatives. So, James founded Hellosaurus to create interactive video for kids through a network of external creators.

James shared his advice for leadership, product development, user research, and the founder journey.

Hire people with a big passion for the product. At HQ Trivia, some of the best hires were previously successful players of the game. They were able to bring this energy, user empathy, and product insight with them to create enormous impact at the company. Similarly, when building the team at Hellosaurus, James prioritizes prior experience building meaningful children’s education or entertainment programs.

Be a transparent leader. When managing a team, be transparent with them about what you are thinking, whether it is challenges you foresee, areas for improvement, or opportunities on the horizon. Transparency is core to building trust with your team. Give your team clarity into your thought processes and decision making.

Ensure that user interaction shapes the content. When creating interactive content, the interaction component must never feel secondary for the consumer. Consumers must feel they have the agency to impact the show and content outcomes through their engagement.

Ask your users to sell your product to you. Oftentimes, when you are conducting interview based user research, people will say what they think you want to hear and generally share positive feedback. However, when you ask them to sell your product to you, you can see if their genuine excitement is there and if they truly understand your product’s value.

See the world through different perspectives. Looking back on his time at Harvard, James is grateful for the diverse set of classes he was able to take and the liberal arts education he received. Learning about new spaces and considering problems from diverse lenses has helped James make better product development decisions.

Get experience building. What best prepared James for the founder journey was his experience tinkering on different projects throughout college and beyond. In these building experiences, James was able to develop the “nothing is ever final” mindset, iterating constantly and finding new ways to improve. He was also able to find joy in the process rather than the outcome, being exposed to temporary failure and learning to overcome these challenges and enjoying the ride.

Take pride in your first draft. Don’t take yourself too seriously in your building or experimentation processes. While the first draft is never utterly ideal, there is a lot of power and magic in creating it. Take pride in your creation and find the inspiration to keep building.