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.

Book Review: 10 Powerful Personas By Kevin Vogelsang

Ever wonder what makes a leader great?  Ever spend time thinking about what the strengths are in your personality or how you might be able to become more like great people around you? Kevin Vogelsang has and he’s written a book to help you answer those questions.  In his just released book “10 Powerful Personas, Kevin examines key attributes of 10 different qualities found in leaders. I learned a lot from the book and I’d like to share a few of the lessons here:

1) Leaders come from everywhere

One of the most interesting things about Kevin’s book is the balance in people he uses as examples of different leaders.  He uses everyone from General Patton to his football coach to his mother as examples of the different powerful personas to great effect.  Because of his wide variety of examples, it made me think about who around me, both famous and friend, that exhibited the traits he describes; it was an excellent reminder that you can really learn from anyone around you if you simply raise your awareness and look for it.

<Click here to read the other reasons at GreenhornConnect.com>

Book Review: Gary V’s Crush It

If entrepreneurship was a team and we had a big game coming up, I have no doubt that Gary V would lead the pep rally and carry the spirit stick.  If you need a book to jump start your passion for entrepreneurship, to remind you why you do what you do and give you some tips to better succeed at what you are passionately pursuing, then Crush It is is the book for you.

When I first started reading this book, I wasn’t sure I was going to buy into it. It felt like sort of fluff.  But Gary V’s enthusiasm is contagious. Before long I was really feeling charged up about his beliefs in pursuing your passions and thinking about how I’m already doing it and how I can do more.

Compared to some more academic entrepreneurial books, this is a quick, easy read (142 pages), but it still is filled with great ideas and concepts.  After feeling like Chris Brogan’s Trust Agents was a bit verbose, I was very happy to breeze through this book. Gary hit on a lot of great points and covered a reasonable number of topics, but never dwelled on any idea too long.

If you’re looking for a quick read to get you pumped up to pursue your life’s passion AND have a method for actually making money on that passion, this is well worth the time to read this book.  If you don’t like overly casual/conversational books, you may want to steer clear of this one.  If I had to boil the book down to one principle, I’d say that it’s “Discover your life’s passion and create interesting content about that in the form you want, then be patient and get paid.”

Next Book: Steve Blank’s 4 Steps to the Epiphany

On Deck: Open to recommendations…

In the hole: Open to recommendations…

8 Resolutions in 2010

With the turning of the new year, it’s that time when people make resolutions. Yes, most people make them and soon break them, but I’m hoping to be different.  These are issues I’ve recognized and was already working to improve before the New Year. I’m simply using the turning of the year to make these goals public; I think by putting them out there for the world to see, you put a bit more pressure on yourself to deliver.  So, below are my resolutions and a few items for how YOU can help me make these all happen.

8 Resolutions in 2010

1) Improve my Punctuality: I’ve had many meetings over the past few months and unfortunately, I’ve had a bad habit of not making it on time to many of them. Sometimes it’s a beyond my control like when the T didn’t run for an hour while Obama spoke at MIT, but often, I’m just not giving myself enough time to get places.

How You can help me: Hold me accountable for punctuality. I’m open to creative ideas. Currently Cort, who films GreenhornTV for me, has it that I owe him a beer for every 5 min late I am. So far, I haven’t been late yet since we made that arrangement.

2)  Improve Time Management: As I launched Greenhorn Connect, I took the approach of doing everything all the time. That’s not a good strategy. I’ve gotten better as time has gone by, but I still find myself losing some days to doing things, but not Getting Things Done.

How You can help me: Any suggestions on how I can become more effective and efficient (books, articles or tips) are much appreciated. Thanks Apollo and Mike for your help already!

3) Get Back to the Gym: For my first 6+ years in Boston, I was a regular at Northeastern’s awesome gym, the Marino Center.  No matter how busy I was through undergraduate and graduate school, I always made time for the gym every other day.  Since I launched Greenhorn Connect, I’ve watched my gym attendance dwindle to not having made it since before Thanksgiving.  Fortunately, I have a pull up bar in my apartment and I’ve been getting creative by creating quick 20 minute workouts in my apartment, but it would be much better if I got back to my old workout routines that are a bit more diverse.

4) Get back to Running: I was a pretty good runner in high school on my cross country and track teams. I racked up a few thousand miles in that time and really look back at it as some of my favorite memories from high school. Unfortunately, I’ve never been able to hammer out a routine in Boston that compared and so I’ve progressively lost my endurance.  I can’t run on concrete (not that I think anyone really can without injury) and this isn’t suburban PA so I can’t run on the roads.  This means I need to get out and take advantage of the 2 great locations near me: the Esplanade and Jamaica Pond.  This one will probably wait until spring when weather improves.

How You can help me: I think having the team really helped me stick to my running, so if anyone lives in the Back Bay area and is looking for a running partner or knows of any running groups, let me know.  I think I’d be running in the 7-8 min mile pace right now, looking to run 3-5 miles a day.

5) Read a Book per Week: I saw this come across the Twitter scape and thought it was great: Read a Book a Week for a Year. At first I said to myself, “I’m so busy! I don’t have time to read THAT much!” Then I read that post…and I realized, that’s like 30-40 pages a day. That’s not so bad. I can do that! So, I just started this on Jan 1st and am 3 for 3 as of this writing for getting my pages knocked out each day. As I hopefully progress on this I plan to also write reviews on Greenhorn Connect for the books I like best.

How You can help me: Two ways: 1) Recommend any books you suggest I read. 2) Loan me a book. Yes, I know I can go to a library, but if I borrow it from you, I bet you’ve read it and could then compare thoughts on the book briefly.

6) Post More Often: Keeping the Greenhorn Connect Blog going became my priority over the past couple of months, but now I think it’s starting to stabilize. I like the idea of having things I write here and on Greenhorn Connect (much like there are New Years Resolutions at both places). I’m going to try to commit to posting more often. To help that, I’m going to try adopting a new Seth Godin-like style here where I just write a couple paragraphs about a thought I have and leave it open for continued thought by you and I.

7) Keep learning: Since I started grad school in September 2008, I feel like I’ve been drinking from the fire hose in learning about entrepreneurship. I look at everything I do as a learning experience and that’s led to zero regrets in my somewhat unorthodox journey.  I hope to keep that mindset in 2010 and continue to leverage past experiences to develop future success.

How You can help me: Give me constructive criticism. I really take all the advice and feedback I get from people to heart. I find many are apprehensive to give feedback, but it’s the only way you can truly improve. So please…share your advice, suggestions and criticisms…I’m listening, and more importantly, acting on them.

8.) Pay it forward: One of the things I’ve learned over the past few months is that often, you can’t help those that are helping you. Instead, the best thing you can do is pay it forward and help others regardless of what they can do for you.  I’ve met with a number of people to share what I’ve learned from Greenhorn Connect and other recent experiences and look forward to helping when and how I can in the future.

How I can help You: Ask! You don’t know unless you try. If I can help you I will.

To me, these are more than resolutions; they’re part of my evolution. I think they actually all tie together as there’s a greater theme of curiosity, learning and organization.  Success in one is likely help success in the others.   Please comment or contact me if you can help with any of those or I can help you.

MIT 100K Elevator Pitch Contest: A Lesson in Awesome

What has a roaring crowd complete with thunder sticks,  a set of hosts in costume, a dancing spaceman and people talking about everything from backless labels to prostate cancer?  No, it’s not the World Series and your average night of commercials. It’s the MIT 100k, where they set the gold standard for awesome.

When I arrived, the event was already in full swing.  As I walked into the auditorium I was hit with an incredible ball of energy; you could feel the excitement and enthusiasm of the crowd and participants. There was also a very entertaining host (dancing spaceman = good, microwave pitch = not so much) and tons of awesome elevator pitches. Where else can you go and hear someone talk about Indiana Jones, prostates and impotence and get multiple laughs, all in under a minute?

To me, the lesson in this is simple: be awesome.  MIT could have had a standard, bland event with limited sound production (sans the Star Trek sound effects), hosts in (regular, not space) suits and a reserved (thunderstick-less) audience.  That would have produced a solid event, with interesting pitches.  Instead, they dialed it  up to an “11” and went all out to entertain and energize everyone in the room.  This is how you get people excited about entrepreneurship.  This is how you make people say “wow. I wish I had pitched” and realize that entrepreneurship can be as cool as sports.

Cheers, MIT100K team. Awesome event.  Looking forward to future events.


Many have written about their experiences as emerging entrepreneurs to great effect. These books, blogs and articles all serve as inspiration to me and fellow young entrepreneurs.  One of my favorite items I’ve read is Mark Cuban’s insight on that journey.  It’s easy to look at him and say, “Wow. He has everything. He’s a billionaire. He owns the Mavericks. He has a gorgeous wife and a great family.”  But did you know he slept on the floor of a cramped, trashy apartment for a few years while he was trying to get his first company off the ground? Or that he read computer manuals in his free time so that he could become an expert with them? Behind every success story is years of hard work and sacrifice…


Now Mark Cuban is a great personal entrepreneurial “hero” of mine, but if we’re talking about inspiration to pursue your goals, nothing compares to Dr. Randy Pousch. At age 47 this Carnegie Mellon professor was given a diagnosis of terminal cancer.  Randy decided cancer could kill him, but not his spirit. In his “Last Lesson,” he shared with everyone his life story and lessons learned.  Below you’ll find the full video of this “Last Lesson.” It’s about the length of a movie, but I dare you to find one as powerful and moving:


I saved a number of quotes from Dr. Pausch for myself, but I’d like to comment on a few that resonated the most with me and others I showed the video (approximate time in the video listed in parenthesis):

(18:40) “When you see yourself doing something badly and no one is saying anything anymore…that’s a problem. It means they’ve given up on you”

I think this emphasizes the fact that feedback is so important. You always want to improve yourself and sometimes it’s really hard to get constructive criticism out of people. It’s often because they don’t want to hurt your feelings, but they’re only doing you a disservice.  Of course, if they just don’t care, you have a bigger problem.  If you ever have constructive criticism on my blog, please comment!

(1:10:35)“Decide if you’re a Tigger or Eyeore”

As my father so eloquently put it, “I always thought Tigger was an airhead.” Yes, in the most literal sense that may be true. But to me, this is about optimism and hope vs. pessimism and acceptance.  Tigger sees all the great in the world and pursues his goals of being happy in life, while Eyeore is always depressed about something and never does anything to change his situation. To me, the Tiggers of the world are those that see problems in the world as opportunities to make a difference.  I’m a Tigger. Are you?

(53:00) “If you do anything that is pioneering, you have to put up with the arrows in the back”

This quote relates to entrepreneurs in two ways.  First, there will always be doubters, critics and haters.  You have to know when to listen to them…is it constructive criticism, or deep down, do you know they’re wrong? In general, I’ve found the best way to know if I believe in what I’m doing is simply to have someone try to encourage me to go another way; if I strongly disagree with their suggestion, I know I’m fully committed to my decision.  The second way this affects us is competition.  There is always someone else with the same idea.  Even if you get a head start and have more customers, better market presence, or superior technology, they’re gunning for you.  As I learned in running cross country, if you aren’t passing someone, someone else is likely passing you.

(26:40) “The brick walls are there for a reason.
The brick walls are not there to keep us out.
The brick walls are there to show us
how badly we want something
The brick walls are there to stop those
who don’t want it badly enough.
They’re there to stop other people.”

When I was a freshman in high school, I joined the track team.  Since my father ran track in college I thought I would be good too.  As it turned out…I wasn’t a natural.  At the end of the year, we had a banquet and the coaches honored all of the best athletes, which obviously didn’t include me. I decided I wanted to be one of those guys.  My coach told me I should join the Cross Country team and so after that banquet, I told him I was going to try to make varsity that fall.  He’s a nice guy, so he didn’t tell me no way, but he basically shrugged me off. He knew I ran a 7:30 mile as my best time that track season, and that pace wouldn’t even be good enough to make varsity.  Little did he know how badly I wanted it. All summer I got up every morning and ran 7.5 miles in the morning and 2.5 miles at night.  By the start of the school year I had run over 600 miles and was doing my morning run in under 7 minute mile pace.  I made varsity, to the great surprise of my coaches and my teammates.

When I set a goal, I passionately pursue it with everything I have and refuse to give up.  It hasn’t failed me regardless of whether it’s an athletic, academic or professional challenge.  I see a few “brick walls” in my life right now; I look forward to breaking them down.


Despite only living half of the average American life, Randy Pousch accomplished a laundry list of lofty and challenging goals including working for Disney Imagineers, experiencing zero gravity, and writing an article for World Book Encyclopedia.  I have a list. Do you have a list? How are you working to check them off?   Don’t be afraid if they’re lofty. Randy’s mentor put it best:

“It’s such a shame people see you as arrogant…it’s going to limit what you’re going to be able to accomplish” -Andy van Dam