539: How to cultivate an environment where innovation thrives – with Catherine Connelly

How product managers can build an environment for breakthrough innovation Watch on YouTube TLDR In my conversation with Catherine Connelly, a 20-year tech entrepreneur who co-founded MyYearbook at 15 and grew it into The Meet Group (a $500 million exit), we explored how to build environments where breakthrough product innovation happens consistently. Catherine emphasized that innovation culture starts with founders but can be cultivated by anyone willing to embrace failure, iterate quickly, and keep customers at the center of all decisions. The key is creating psychological safety, celebrating learning from failures, and making risk-free experimentation possible. Key Topics * Building psychological safety that enables risk-taking * Structuring product results meetings that celebrate learning from failures * Creating systems that make experimentation truly risk-free * Implementing a “kill fast” mindset for unsuccessful products and features * Using customer stories to drive meaningful innovation * Balancing operational execution with innovation initiatives * Leveraging storytelling to gain support for innovation efforts Introduction Ever wondered why some teams consistently create breakthrough products while others are barely keeping up on maintenance work?   Today, we’re tackling how to build environments where product innovation actually happens! Every product leader has watched promising ideas die because of organizational roadblocks, excessive caution, or flawed decision processes. You know firsthand that brilliant concepts mean nothing without the right conditions to develop them. From this episode, you’ll walk away with methods to immediately transform how your team innovates.  Our guest, Catherine Connelly, is a 20-year female tech entrepreneur. She co-founded MyYearbook at 15 years of age and grew it into The Meet Group, a social dating company, later achieving exits totaling $600 million. Her recent book Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur captures two decades of creating environments where breakthrough innovations thrive despite constant market shifts. Building a Foundation for Innovation Culture Catherine explained that innovation culture starts with the founding team and how they approach work from the very beginning. At MyYearbook, the foundation for innovation began with a sibling dynamic between Catherine and her brothers that created natural psychological safety. Working with her brothers meant they were used to bouncing ideas off each other without fear of judgment. This family dynamic established an environment where team members could pitch ideas without worrying about negative consequences if those ideas didn’t succeed. The understanding that a person’s worth isn’t tied to the success of their last idea became a cornerstone of their innovation approach. For product managers looking to foster innovation, the culture supporting innovation typically comes from the founders or founding team. How things work from the very beginning shapes the organization’s approach to experimentation and risk-taking. Catherine described how this initial foundation allowed her team to maintain a culture of innovation throughout the company’s growth: