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Founder of Scott's Cheap Flights talks about his favorite books

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In 2013, after getting his degree in political science, Scott Keyes was working as a freelance journalist in Washington D.C.

One night, while randomly browsing flights, he ran into a bargain: an incredibly cheap round-trip plane ticket, between New York City and Milan (Italy), for only $130. The city wasn’t a priority on his travel bucket list, but he decided he couldn’t miss the opportunity. When he got back from his vacation, his friends and coworkers asked about his travel hacks, so they could also discover similar offers.

That’s how Scott’s Cheap Flights was born. Instead of just notifying each person that was interested in deals, Scott started a free newsletter that he sent to his friends, where he alerted them of extremely cheap flights. It started as small side project, but grew into what’s now a business based on a freemium-model, with more than half a million subscribers, 15 employees and $4 million annual revenue.

I reached out to Scott, curious to learn what books influenced him, what he learned from them, what books he’d recommend, what’s his reading routine and the likes. Find out more from our interview below!

What’s your favorite book and why? Business and non-business, if possible.

1491. It’s one of those books that takes everything you thought you knew about the history of European colonialists and indigenous groups in the Americas and turns it on its head. Just a fascinating deep-dive into early American history that questions a lot of dogma we were taught in school.

Business-wise, Getting Things Done. Big believer in the David Allen method.

Was there a moment, specifically, when something you read in a book helped you? Can you tell me about it?

Reading How To Win Friends And Influence People when I was young and realizing how important empathy is. Putting something in someone else’s best interest rather than your own. Few books that were written nearly a century ago are still as true and eloquent today as they were then, but Dale Carnegie’s work is certainly one of them.

What books had the biggest impact on you? (perhaps changed the way you see things, dramatically changed your career path)

Reading Daily Rituals by Mason Currey dramatically improved my productivity and work-life balance. It showed me that most great historical figures weren’t workaholics, but instead worked hard (mostly in the morning) and then had plenty of unscripted time in the afternoon to ruminate, digest, and brainstorm. It’s a model I’ve tried to emulate, waking up early in the morning, churning out a bunch of work before lunchtime, and then taking it relatively easy thereafter.

What books would you recommend to youngsters interested in your professional path? Why? (no number limit here)

Other than How To Win Friends And Influence People and Daily Rituals (for the reasons outlined above), I would recommend reading both Malcolm Gladwell’s collection, everything from Tipping Point to David & Goliath, and Michael Lewis’ as well, from Moneyball to The Blind Side. Irrespective of content, both are wonderful writers who use stories in effortless, compelling ways to make larger points. It’s something that can and should be emulated by everyone, not just writers.

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I’m interested in finding out more about your reading habits. How often do you read? In what format?

Not often enough! Once I entered the start-up world too much of my free time got eaten up focusing on work. But doing my best to get back into reading books and long-format magazines like the New Yorker.

How do you make time for reading?

I used to read before bed every night, but then my body associated reading with sleeping and it made it hard to last more than a few minutes. So nowadays usually late afternoon once I don’t have any creative juices left is when I’ll turn to a book or magazine.

Do you take notes or have any other technique for conquering the torrent of information?

Not really! I’ll keep a list of books I’ve read and enjoyed, and maybe one or two most interesting takeaway points from each, but other than that I just enjoy them as-is.

How do you choose what books to read next?

Whichever one on my ever-expanding to-read list is available from the library the fastest, I’ll grab.

Do you prioritize those recommended by certain people? Is there anyone that you consider a book-recommendations guru?

Absolutely! Not anyone public per se, though I do enjoy the book recommendations that The Ezra Klein Show always ends his podcast with. In general though I’ll usually post a bleg on Facebook to get ideas from friends about books I may enjoy.

Last question: what book are you currently reading and what are you expecting to gain from it?

Just started The Skies Belong To Us. Working in the travel industry, excited to get a sense of what flying was like decades ago.

Links where you can follow Scott Keyes or find out more about his projects:

  • Scott @ Twitter
  • Scott @ LinkedIn
  • Scott’s Cheap Flights @ Twitter
  • Scott’s Cheap Flights @ Instagram
  • Scott’s Cheap Flights @ Facebook
  • Scott’s interview @ CNBC
  • Scott’s Reddit AMA session from 2015
  • Scott’s second Reddit AMA session

  • Books mentioned by Scott Keyes in this interview:

  • 1491 by Charles C. Mann
  • Getting Things Done: The Art of Stress-Free Productivity by David Allen
  • How to Win Friends and Influence People by Dale Carnegie
  • Daily Rituals: How Artists Work by Mason Currey
  • The Tipping Point: How Little Things Can Make a Big Difference by Malcolm Gladwell
  • David and Goliath: Underdogs, Misfits, and the Art of Battling Giants by Malcolm Gladwell
  • Moneyball: The Art of Winning an Unfair Game by Michael Lewis
  • The Blind Side: Evolution of a Game by Michael Lewis
  • The Skies Belong to Us: Love and Terror in the Golden Age of Hijacking by Brendan I. Koerner

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