The Adventure Capital Pod

Tried or die with a Dirtbag CEO


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Ride or die with a Dirtbag CEO

Meet Kay Rodriguez, the self proclaimed Dirtbag CEO of both Outerly and Urban Outdoors. Kay’s outdoor entrepreneurship started from a logical, yet surprising, place. She worked at Bain as a strategy consultant. After a few years, she knew her path needed to change - so when she started to sense a problematic pattern - she hit the ground running. Her background, plus desire to help get people outside, set her on this exciting journey.

Startups are all about acting quickly, learning faster and adapting to new information. Kay discusses the process from the early days of Skyline Adventurer to it’s current iteration, Outerly. There were critical moments where new info challenged Kay to reimagine and reevaluate - much of this while writing about badass adventures all over the country in her converted van.

We learned a number of high-level perspectives from Kay in this episode about founding an outdoor industry business:

  • Passion, dedication even obsession is a necessity
  • Decide on something, anything, and just go do it
  • It’s better to try and fail -> because that way you learn something
  • There are two key tactical takeaways from this episode. Both are tactics that give you tremendous insights into your business. Our job is to solve peoples problems and provide value, you need to always be learning and adjusting based on new information.

    • Interviewing customers
    • Google Alerts Daily Digest
    • Much about this episode epitomizes the Founder journey. Kay says it best, “I guess there's a couple morals of this story. The first is if you're in a situation where things might be precarious, a little risky, it's better to enjoy that experience while laughing and making light of it then freaking out”. But, you’re going to have to listen to the episode to found out exactly what she’s talking about. 🙂

      Learn more about Kay! https://outerly.co/

      Twitter: @kaygoesoutside, @urbanoutdoors, @letsgetouterly

      Instagram: Kay Rodriguez, Urban Outdoors, LetsGetOuterly

      Linked In: Kay Rodriguez

      Be sure to check out what we're building at Rerouted too! https://linktr.ee/rerouted

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      The Adventure Capital PodBy Chap Grubb