Why you should read 100 books

When I was fresh out of college with a internship at E Ink (maker’s of the display screen for the Amazon Kindle) I emailed the founder and then CEO, Russ Wilcox, to see if he would meet with me to give me some advice on entrepreneurship. Lucky for me, he was willing to schedule a meeting before my internship ended. You can read the full story here, but one of the best pieces of advice he gave me during our meeting was simple, yet powerful: Read 100 Books.

At the time it almost didn’t make sense and led to more questions than answers. What books? Why that many? How fast? By when?

I remember frantically writing down a bunch of book titles he started mentioning and then he stopped me and said the important thing was that they were on a diverse set of topics with different viewpoints instead of any specific books. He suggested trying to read 5-10 on categories like sales, marketing, leadership, negotiation, etc.

Mission Accomplished.

5 Years and 4 months after that conversation, I’ve finally hit the number and now looking back, I realize it’s one of the most important pieces of advice I ever received. I would not be where I am today if I hadn’t read as much as I have. Reading 100 books has done all the following for me:

  • Helped me better understand the responsibilities of coworkers (especially important as a product manager and startup founder).
  • Being comfortable in a conversation on just about any subject due to what I’ve read.
  • Rapidly improved my skills in key work responsibilities helping me accelerate my career and avoid costly mistakes.
  • Met other great people who also read regularly.
  • Given me the confidence and framework to help me learn anything.

If you’re reading this, I encourage you to also read 100 books. But realize it’s not about the number, but a routine of reading regularly that will serve you well throughout life.

Here’s my quick advice on how to make it happen and make the most of it:

1) Read what you can apply immediately.

I’ve managed to read a wide variety of books that have helped in my career and I’ve always chosen books based on what my current challenges and interests are. This has helped me apply concepts I pick up as I read a book, usually over the span of 2-4 weeks, depending on the length.

When I was moving to SF to run product at KISSmetrics, I started out with a great book on Product Management, then dove into a few books on design, before finding myself diving into sales, marketing, leadership and strategy books depending on what was happening at work and my personal life. Every time, I found great ways to build on what I read in my life around me which has helped tremendously with retention and understanding.

2) Get good recommendations.

Not all books are created equal. In fact, most books are pretty terrible, especially business books. There are gems out there though, so it really pays off to ask others who read what the *best* books are they’ve read on a subject. This has saved me tons of time on books that aren’t worth my time. This is why I made a list reviewing of all the books I’ve read  and some of my all time favorite books for entrepreneurs here. You’ll also occasionally find posts about books that CEOs like Jeff Bezos has his leaders read, which are usually great.

3) Build a routine of reading.

I read on public transportation. First it was riding the T in Boston and now MUNI around SF. I love this for so many reasons:

  • It gives you something to look forward to even when a bus commute might be lengthy.
  • A book won’t get stolen like your cell phone might be when you have it out as you play Angry Birds/check Facebook, etc.
  • It gives you bite size chunks of reading as most rides are 10-30 minutes…just enough for a chapter or two.
  • A book is a great way to get just a little bit more personal space on a crowded bus.
  • It’s a great warm up and cool down to your work day if you read during your commute.

If that’s not an option for you, build a routine around it in some other way. Maybe it’s 20 minutes before you go to bed, while you eat breakfast or perhaps audio books while you drive to work. It is the routine of always reading something that will carry you through that many books over the years.

4) Carry your book around with you.

Nothing sparks a conversation like someone noticing what you’re reading. Often those that notice read a lot too, which is a great way to make friends and you can get more recommendations for books from them. This also means that if a friend is running late, you always have a productive way to fill the time.  I brought Dale Carnegie’s “How to Win Friends and Influence People” with me to Bootstrap Live and ended up talking with Andrew Warner and the guy next to me about how much we all loved it.

5) Write all over your books.

Despite working in technology, I still prefer physical books in my hand. I underline, I highlight and dog ear all my books. Something about it helps me with retention of what I read. Even if you prefer to read on a tablet or Kindle, be sure to take notes and challenge yourself to think about how to apply what you’re reading. It helps a lot to review books you’ve read before when you have that subject come up. It’s amazing to me how often past events line up as examples (or counter-examples) of something I’m reading. I’m always sure to take a moment to consider it and write it down in the book.

6) Always make progress.

Life doesn’t always go as hoped or planned. There are times of frustration and stagnancy both personally and professionally in all our lives.  I’ve found one of the best things for me is knowing that no matter what is happening in my life I’m always learning because of what I’m reading. I can always look back and see progress there.

It has also helped that when I’ve had down times, if I read something related to it like a book on happiness or successfully navigating your 20s, I’m actually being proactive about the problem and getting advice from someone great who took the time to research and write a book about the subject.

Remember, this is not a race. The point of reading all these books is to absorb all the ideas and skills shared in the books, not race to the end.

I’ve heard some people like to skim books and think that doing things like reading the opening and closing paragraphs of a chapter and reading headlines in the chapter is enough. They’re either reading the wrong books or missing out on some deep lessons.

As a wise man once said, “Anything worth doing is worth doing well.” It is the journey to 100 books that I both enjoyed and grew tremendously from…not the milestone of specifically 100 that matters to me; I haven’t stopped reading and won’t anytime soon. My Amazon Wishlist is longer than ever (please suggest the best books you’ve read in the comments!) and I can’t wait to learn through more great books for the rest of my life.

3 Books Every Investor Should Read

As an entrepreneur, when I consider the ideal investor I would like to have, it’s a lot more than someone with money. I want them to have characteristics like:

  1. Able to make smart bets: Investments are largely made when it’s too early to tell with certainty who or what will win in a market. 
  2. Add value and insights: This is more than replaying personal war stories and biasing from your own experiences.
  3. Asking good questions: Someone who pushes founders to take a step back and recognize the things that matter often comes more from asking questions than providing answers.

Being great at those three things is no small task. Fortunately, there’s been some great books written that can supplement the knowledge and know-how of even the most veteran entrepreneur or get a new investor off on the right foot. These are books I’ve read and re-read because they’ve providing so much value to me and I believe can specifically help investors as well.

The Innovators Dilemma by Clayton Christensen

Disruption is a brutally abused word in tech these days. Clayton Christensen brings it back to reality and explains how it really works in this classic written in the 90s (and has arguably gotten better with age).

As an investor this is critical so you can call BS on an entrepreneur that claims they’re disruptive, but really are hopeless. This book will help you understand not only how to recognize disruptive technology in its earliest days, but what it means to get in the market, grab a position and successfully grow and take down the incumbents. Benjamin Tseng, a Bay Area VC, has a great post also discussing the value of this book for investors here.

Investor Scenario: A founder claims they have a disruptive innovation and are telling you about their immediate mass market plans, The research in Christensen’s book will help you guide them a better approach or to pass on the deal.

The Master Switch by Tim Wu

Over the past 100 years, communication platforms have dramatically changed and evolved. During this time, we’ve seen the emergence of the telephone, radio, television, email, the internet and more. Without fail, every time one of these new mediums emerged, they fought an uphill battle to eventually win the market.

This book goes perfectly hand in hand with Innovator’s Dilemma by walking you through how many technologies were slowly commercialized and changed the world. By the time you get to the end the patterns will be impossible to miss and priceless to match against what you see in new markets emerging (some of which you hopefully can invest and place strong bets on).

Investor Scenario: A founder has a transformative technology. Knowing the patterns of past innovative companies, you can help them anticipate resistance they may face both in the market and legally.

Tribal Leadership by Logan, King & Fischer-Wright

A book on culture to go hand in hand with two on innovation cycles? Absolutely. While there are other books out there I’ve rated higher on culture, none are more powerful for an investor.

You only get a limited amount of time with a founder and their team, so knowing how to quickly tell the difference between a strong team culture and one struggling is huge. What makes Tribal Leadership special is how it helps identify the key words that you can listen for to tip off how a company is really doing. 

Armed with this information, you can help a founder get back on track if some of the team has issues.  It can also help you decide if you should pass on an investment that looked good otherwise; a motivated, excited team will be significantly more productive, work longer hours and help recruit the best talent. You need those for the characteristics for a company to hit deadlines and win the market.

Investor Scenario: You visit one of your investment’s offices. If you overhear employees talking about their excitement for the mission, they’re operating at a high level. If instead they’re complaining about how much their work or a project sucks, you may want to ask the founder some questions.

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Unfortunately, many business books are a complete waste of time. Luckily, gems like the 3 books above exist and help tremendously to educate us, change our perspectives and diversify our knowledge on important subjects. I’d love to hear any great book recommendations in the comments for investors or entrepreneurs.

My Philosophy on Reading Books

I read a lot of books. For the past 3 years, I’ve averaged finishing a book every 2-3 weeks (thanks to this post inspiring me). Through all this reading, I’ve learned a tremendous amount thanks to a specific philosophy I’ve had on what I choose to read.  Since I just published the organized list of all the books I’ve read and recommend, I wanted to explain how I arrived at this list. These are my strategies when choosing how and what I read:

  1. Only read for purpose – I read books on subjects I want to learn about (i.e.: non-fiction only), so reading is about education not relaxation or escape for me.
  2. Stick to highly recommended books – I ask trusted friends, mentors and observe leaders in tech for books to read. I hate wasting time on a bad book, so I work hard to ensure anything I read isn’t a waste. This is why I include a section in my books list on books not to read.
  3. Read to solve current problems or satisfy current interests – This helps me quickly apply whatever I read to challenges I’m facing in my work and/or personal life.
  4. Write in the margins – If I don’t write down the ideas sparked in reading, I won’t remember nor apply them. It also makes it easier to revisit concepts I found interesting in any book I’ve read.
  5. Read in small bites – I read when I’m on public transportation, which generally means 15-30 minute bursts. This ensures I have plenty of time to think about each concept I read about and absorb as much as I can. Credit to Leo of Buffer for expanding on this subject here.
  6. Share - When I learn interesting concepts or a great book, I share it. The subsequent discussion with others leads to even more learning.

How do you decide what books to read? What motivates you to read?