June 3, 2022

#109 Alex Simon of Elude: My Favorite Books, Tools, Habits, and More | 20 Minute Playbook

#109 Alex Simon of Elude: My Favorite Books, Tools, Habits, and More | 20 Minute Playbook

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.

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In Episode #109, we deconstruct Alex Simon's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Alex is the CEO and Co-Founder of Elude. We cover mentors, favorite books, and daily meditation.

“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






In this episode, we deconstruct Alex Simon’s peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. In it 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


Alex Simon left a career in investment banking to start the travel startup Elude, where he's the co-founder and CEO today. Elude is focused on helping people find and book incredible travel experiences that help them escape and see the world. It's the only place 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. Why he wishes he always trusted his gut instincts as much as he does today. He shares his two favorite books, which are World Travel by Anthony Bourdain and The CEO Within by Matt Mochary. And he talks about why he meditates at the end of each day and how he includes reflection on how the day went into that routine.




iTunes: https://podcasts.apple.com/us/podcast/outlier-academy/id1523851182

Spotify: https://open.spotify.com/show/58edVNgqaPNaCSGSxM6pef?si=88f37a5d20434775

Overcast: https://overcast.fm/itunes1523851182


Learn timeless lessons on work and life from iconic founders, world-renown investors, and bestselling authors. Outlier Academy is the forever school for those chasing greatness. Past guests include Gokul Rajaram of DoorDash, Scott Belsky of Benchmark and Adobe, Joey Krug of Pantera Capital, Mark Sisson of Primal Kitchen, Luke Gromen of The Forest for the Trees, and Brian Scudamore of 1-800-GOT-JUNK.

Website: https://www.outlieracademy.com

Twitter: https://www.twitter.com/outlieracademy


Outlier Academy is hosted by Daniel Scrivner. Over the last 15 years, Daniel has led design teams at Square and Apple, turned around a $3M+ ARR SaaS business, and invested in more than 100 companies. He launched Outlier Academy in 2020 to learn from the world’s best founders, investors, authors, and peak performance experts.

Website: https://www.danielscrivner.com

Twitter: https://www.twitter.com/danielscrivner

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