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Building Belonging & Getting Outside with Kay Rodriguez of Outerly


How can we find genuine connection in the noise of the digital age? Kay Rodriguez, CEO of Outerly, shares how she's using outdoor experiences and a beginner's mindset to foster belonging at scale and counter the loneliness epidemic.


Episode Summary:
What does it mean to create true belonging in an increasingly disconnected world? Kay Rodriguez, CEO of Outerly, joins us to discuss her mission is to foster authentic interactions. She shares insights on building a human-centered company, embracing failure as part of the startup journey, and the importance of staying grounded in a mission-driven purpose.


Kay tackles the tension between social media’s potential to connect and its reality of isolating people, and she and host Kt McBratney reflect on the role of nature, human interaction, and vulnerability in building a deeper sense of community. In this candid conversation, Kay also explores her own growth as a founder, including the importance of learning new skills and being comfortable as a beginner.


Key Takeaways & Themes:

  • Creating Belonging Through Nature: How connecting strangers through outdoor experiences offers participants a third place for belonging.
  • The Problem with Social Media: While social media began as a way to connect, Kay talks about how its evolution into a space that isolates and fosters comparison, driving people away from genuine connection.
  • Human-Centered Companies: Kay shares the value of building human-powered tech and fostering vulnerability in business relationships, even when it comes to investors.
  • The Value of Being a Beginner: How embracing learning, new skills, and being a beginner is a powerful way to remain humble, creative, and adaptable.
  • Growth vs. Individual Impact: While Outerly has ambitious goals for expansion, Kay remains focused on the individual impact each walk has on participants, emphasizing the importance of genuine human connection in a scalable business model.

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