Special Guest: Ruben Garay


Ruben grew up in Sweden and made his way over to the US after publishing the world’s largest music website at the age of 18, garnering 30 million unique visitors in 5 years, before getting acquired by Hollywood.com

Since 1996,  Ruben has been immersed in the evolution of the world wide web, building recognizable brands with loyal audiences.

His already successful career in the entertainment industry led to studying at  New York Film Academy and Music Business at the Musician’s Institute in Hollywood. He then went on to work as a concert video editor for Live Nation and helmed several video and post production departments of major online publications such as MTV, VH1, Fuse, Celeb TV and Hollywire.

In 2013, he left the entertainment business and began focusing on his childhood dream of becoming an airline pilot.

With only a private pilot’s license and 125 hours of total time to his name, Ruben acquired all of the necessary ratings and became a flight instructor until he achieved 1500 hours in 2 years and 2 months. In 2015, Compass Airlines, a regional airline based of LA was the first airline who took a chance on him and within 15 months he was upgraded to the left seat of the Embray-air  E175. After being a Captain there for 3 years, he took a job as a Captain flying the Embraer E-135 for JSX. Then, 7 months later, on a bright Saturday morning, he received an interview invite from a major airline

Despite loving his job at JSX and being home based in Las Vegas, he couldn’t say no to the job offer. Nevertheless, before he new it, Covid entered the picture and Ruben was furloughed just shy of completing his 200th hour on the Airbus A320/A321 based out of LAX.

Outside of flying, his hobbies include building the latest expert mode Legos with my wife, hanging out with their two dogs (a Peagle named Charlie and a Corgi named Bella), jumping out of perfectly good airplanes, and working on side projects, such as mentoring young and and upcoming entrepreneurs with an emphasis on online e-commerce, video production and marketing.


00:00 Ruben reads an excerpt from his travels


  • Drea introduces Ruben
  • Drea & Ruben discuss how long they’ve known each other and their background of the entertainment industry in Los Angeles
  • Drea & Ruben talk about Femme Fatality web series and how successful it became pretty quickly.
  • Ruben talks about his success as a pilot coming from very little monetary help and hard work. He talks about hard work and results that will come out of it if you keep going.
  • The power of believing in yourself and the American dream


  • The beginning of Ruben’s career with the World of Brittany www.worldofbrittany.com, which was the first fan site for any celebrity on the internet and it was all about Britney Spears.


  • Ruben talks about the beginning of his life in aviation and his love for planes even as a child.  Ruben talks about his early childhood living as an expat and meeting friends who had parents who were airline captains.
  • Ruben talks about Microsoft Flight Simulator in the 90’s and his progression to getting his pilot license.


  • The story of the day Ruben decided to become an airline pilot and the transition to Compass airlines, then JSX and then over to a major airline.


  • Ruben talks about the difficulty of getting hired by a major airline and how most of the hires come from the military
  • He shares the moment when he got the call that he got hired for a major airline and how surreal it felt.
  • He shares how excited he was to finally get hired and then covid-19 hitting the world a month after his hire
  • The Gala he was invited to after getting hired and then losing it all to Covid-19
  • While he was training, he saw the way the world started evolving in front him from pre-covid to post-covid
  • He discusses his time at the hotel where he was training and how there was suddenly no staff in the hotel except for the one man at the front desk.


  • Ruben talks about him and his wife getting sick with Covid


  • Ruben was one of the 40,000 airline staff who got furloughed.  He discusses what this experience looks like.


  • Ruben talks about the pilot community and how they’ve supported each other.


  • Drea discusses the need for travel and the need for pilots as a result once the covid situation subsides
  • Ruben discusses the importance of travel and adventure.


  • Ruben shares his favorite place he’s traveled which is Cambodia
  • He really enjoyed Siem Reap, the quality of food and hotel – The Lotus Blanc $60 per night pre covid but now it’s even cheaper.
  • $50 for a 6 hour spa day.
  • He went to the Angor Kwat and loved the spiritual experience


  • Traveling is the best medicine for the soul


  • Ruben shares his most meaningful person he’s ever met on his travels


  • Ruben shares his most fulfilling moment as a pilot.  He loves the fact that being a pilot means part of everyone’s life when he’s taking you somewhere on a journey.


  • Ruben shares his advice to any aspiring pilot who is passionate about it because it’s hard but it’s very rewarding

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