20 Minute Playbook: Alex Simon – Co-Founder and CEO of Elude

Alex Simon is CEO and Co-Founder of Elude, a travel app that allows users to discover new destinations based on timing and budget. In this episode, Alex and Daniel discuss mentors, favorite books, and daily meditation.
Last updated
June 3, 2022
Min Read
Alex maintains a daily, 15-20 minute guided meditation practice.
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“You don't need to be doing something every single moment or every single day to feel accomplished. Actually, the best times of creativity come when you have nothing going on.” – Alex Simon

Alex Simon left a career in investment banking to start the travel app Elude, where he's the co-founder and CEO today. Elude is focused on helping people find and book incredible travel experiences. It's the only resource where you can simply input your max budget, your local airport, and how many days you'd like to be gone to find incredible destinations around the world that fit those parameters. So you can ask the question, where can I go next week for $1000?

In this episode, Alex shares why he's been fascinated with crystals, the three mentors he's learned the most from, and why one of them has continually pushed him to simplify Elude's design and user experience again and again and again. We discuss why he wishes he always trusted his gut instincts as much as he does today, and he shares his two favorite books, World Travel by Anthony Bourdain and The CEO Within by Matt Mochary. Finally, he talks about how and why he meditates at the end of each day.

For more, explore the transcript of this episode.


In this Playbook episode, we cover:

  • 00:00:00 – Introduction
  • 00:02:02 – Alex’s recent fascination with crystals
  • 00:03:47 – Networking as a superpower
  • 00:04:50 – Guidance from leaders at Lyft, Priceline, and Kelton Global
  • 00:07:18 – Always trust your gut
  • 00:09:11 – Building a startup is about marketing, tech, and everything business
  • 00:10:39 – Alex’s favorite books to recommend
  • 00:12:17 – Why daily meditation is a non-negotiable
  • 00:17:13 – Jiu Jitsu as an outlet and creative source
  • 00:18:34 – Why enjoying your daily work is so important

Books Mentioned

The following books came up in this conversation with Alex Simon

Selected Links

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