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Chris Oliver, Software Developer & Entrepreneur, Gives Enthusiastic Insight on The Books that Helped Him Grow

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Chris Oliver is a software developer and entrepreneur based in Missouri. He’s the creator of GoRails, an education site for Ruby on Rails developers, (easy self-hosting of Rails apps), and several other projects.

Chris has been working on GoRails for four years. Until 2014, he has been a consultant on Ruby on Rails for businesses and startups. He started documenting his programming practices on, and, when he realized he had an audience, decided to turn the educational site into a product.

Chris started programming when he was a teen, learning from a book on programming Basic that he received as a gift from his father. Over the years, he self-taught a bunch of programming languages, and took his degree in Computer Science. He now enjoys building thoughtful software and inspiring people to become better programmers (you can read him on

From our interview you’ll find out more about the books that left deep marks on him, how stoicism helped him in his business, the advantages of re-reading books, and many more interesting subjects.

Estimated reading time for this interview is 10 minutes. If you'd rather listen to it, you can do it on iTunes, Google Play or Stitcher.

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

My favorite book by far has been Mastery by Robert Greene. It’s not a business book per-se but it dissects the approaches and practices of people who are exceptionally talented in their fields, typically far better than any of their peers. I found this book to be really reassuring about the amount of practice and time it takes to become great at things. He covers the various steps towards mastery starting with apprenticeship all the way till breaking out on your own and challenging the fundamental ideas of your field.

As for my favorite business book, I’d probably say Competing Against Luck. It talks about the “Jobs to be Done” mindset when you’re thinking about why your customers buy your product. I found that it puts you in the right mindset to understand the perspective of your customers so you can serve them better. It’s surprisingly hard to understand the reasons why people buy things and this book helps you look at it from a much better angle.

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

I remember reading The Obstacle Is The Way by Ryan Holiday on a road trip one time. It was during a time that I was feeling particularly frustrated with my business and was just having an all around hard time. The idea of the book is that if you recognize things are hard, you should keep going. It teaches you to seek out the obstacles because few people even try and even fewer make it past the obstacles. When I got home from my trip, I remember sitting down and realizing I was being stubborn and not doing the work I needed to do. Immediately, I could tell things were heading in a much better direction.

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

Mastery is definitely at the top of this list. No matter what you are interested in, being truly great any one particularly thing will set you apart from the rest.

The Hard Thing About Hard Things was fantastic. Since I’m in startups, there are a lot of very tough decisions to make and you have to have a lot of courage to make them.

Surely You’re Joking Mr. Feynman I have read many times. It takes you back to childhood curiosity of learning things. Feynman was also a master at the appearance of being a “genius” because he would often make educated guesses which blew the minds of people around him, therefore earning his reputation as a genius.

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

Mastery for the reasons I mentioned previously. It’s great for anyone, no matter what career path.

The Art of Learning as well is phenomenal. You’re always learning new things in programming and startups so being good at learning is a crucial skill to have.

Masters of Doom. Many of us started our careers in programming because we wanted to make games. This book covers the story of John Romero and John Carmack as they created ID software making Doom, Quake, and many other games we grew up playing as kids. It’s truly inspiring for any software developer.

Algorithms to Live By. This is a great book talking about how you can use computer science to help you make decisions in life. How do you know when to make a decision on the perfect house? Car? etc? It helps you apply algorithms to making those decisions optimally without getting lost.

Zero To One. For anyone interested in startups, this is a highly recommended book about what it takes to start a business.

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

I usually read about 1-2 books a month these days. Most of them are using Audible because they’re super convenient and I can read while I’m doing other things. Kindle books are my second choice because I can easily highlight and leave notes there. I don’t read a lot of physical books anymore because Kindle is so much easier and I have access to any book, anytime.

How do you make time for reading?

Most of my best reading is done while driving, going for a walk, or while I’m at the gym. I can easily get several hours in a week that way and I can speed up audiobooks to 1.5x speed or more to get through them faster. I love audiobooks because I can also recall where I was when I read a specific part and that sends me back a flurry of thoughts of what I was worried about at the time and so on.

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

I keep a list of book notes shared across my phone and computer so if I come across a particularly great quote, I will stop and write it down and revisit it later. These are often the nuggets of wisdom that I’m looking for in a book and by writing them down I can revisit those quotes and remember the majority of the key points made in the book.

I also love to re-read books. It seems quite uncommon, but re-reading a book deeply solidifies the ideas of the book to me. I notice the first time I read a book I’ll get the general gist of things, but I might forget the important parts quickly. If it’s a particularly good book, I’ll read it two or three times over the next couple months. This really helps solidify the ideas in my brain because I’ve spaced out the reading and I notice ideas from the book come to mind much more often while I’m working.

Can you give me some examples of books that are on your to re-read list?

I’m currently planning on re-reading The Obstacle is the Way. It’s probably the perfect book to reinforce your New Year’s resolutions.

Mastery as well will be re-read at some point this year. I like to break that book out anytime I’m feeling particularly frustrated or unsure of where to go next. It helps rejuvenate me and get me back on track.

I also want to re-read Meditations by Marcus Aurelius again as well. I love reading the stoics.

How do you choose what books to read next?

I usually choose my next book based upon which ones are recommended the most. I keep a wishlist of books going on Audible and sift through there to find something that strikes my mood at the time. Sometimes it’s biographies and sometimes it’s business or philosophy.

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

Several people come to mind here. I am a huge fan of Derek Sivers and he maintains a long list of books he’s read and his ratings and notes on each one. I will often browse this for books he recommends and some up if I’m not sure what to read next.

I also have gotten a lot of great book recommendations from interviews with Naval Ravikant and his Twitter account. On Tim Ferriss’ podcast, he often asks guests what books they recommend and I’ll sometimes pick up a few of those if I really liked who was on being interviewed on the podcast.

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

I’m currently reading Innovators by Walter Isaacson. I love reading books like this because you learn about the lives of people who have created amazing things. It teaches you that their lives were often much harder than you realize and the struggles you’re going through are very similar to what they had to go through before they were successful. It’s really inspirational.

Links where you can follow Chris Oliver or find out more about his projects:

All books mentioned by Chris Oliver in this interview:

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