The Startup Playbook Review and Notes – Part 1

I have been reading tons of startup books lately and have learned a lot from all of them… Once in a while I run into a great book that is profoundly impactful and potentially life-changing.  I have just started reading a new favorite and must-read for anyone interested in starting (and running) a business. The book is The Startup Playbook and I LOVE it so far. It’s not a how-to guide for building and running your company and it’s not a “scientific” book on business and company creation. It is a compilation of very successful entrepreneurs – about 4 or 5 pages on each person, introducing them, give you a little of their back story and why you should listen to them; followed by a couple of paragraphs on their “playbook” and finally a section of the “best advice” from this person.

The advice is great. The playbook is informative. But my favorite is their stories. I just could not help being super inspired by these people and just wanting to put down the book and go build my company :)… I am about a fifth through the book and want to blog about some of the highlights so far. I am actually reading this with a highlighter in hand, marking it up and taking notes – I almost never do that. I am hoping that I can come back to these series of blog posts in the future when I am down and need some inspiration and I hope it does the same for you and maybe make you go buy the book

We are all familiar with heroic stories of entrepreneurs  These stories tell of easy, quick or inevitable success. In reality, there are almost always massive challenges, delays, setbacks, risks, and uncertainties  Indeed, entrepreneurs and pioneers have to believe that their journeys will be successful; they would never have set out without that belief. But the journey is almost always hard.

This is a great definition of entrepreneurship and what this book is about

…[entrepreneurship is] jumping off a cliff and assembling an airplane on the way down. This book is about airplane assembly, weather patterns, and flying intelligently.

This quote describes how I feel right now.

[during the discovery phase]… founders are typically roaming around in the darkness, looking for intellectual light switches to illuminate how their ideas stand up to customer needs and competitive offerings.

The introduction to the book has a very “cut to the chase” section where the biggest and most critical ideas of the book are summed up… Here are some highlights:

Know thyself

Your startup company must be rooted and flow from the founder’s innate gifts.



Ruthlessly focus on your biggest ideas. This is a personal weakness of mine and I am constantly fighting the urge to chase something “new and shiny”.

…choosing a maniacally focused path and betting it all is one of the hardest parts of the job and it requires the most courage. But it is often what’s required to truly win a market.


Build painkillers, not vitamins

If you can’t describe you company’s value as a painkiller, then I recommend you redefine and refine your business thesis.

Be ten times better

…be ten times better than your competitors. You cannot be incrementally better.


Be a monoplist

…their intentions were not predatory or abusive… simply a way to focus on building market-dominating companies.


Take Risks

I have been to many third-world countries and I have to completely agree with the author that “You’ve Won Humanity’s Lottery; Be Grateful. Take Risks.” This is true if you live in any developed country, specially here in America.

…we have a responsibility to take great risks because in truth, we have few true risks at all.


Interesting Quotes

…if you cannot lead yourself, you cannot lead others.


startups are stupidly hard… the decision to pursue them is irrational because the experience can be such a torturous one.


Chris Anderson

Founder of TED –


Wherever you see rea engaged passion, that means there’s something worth investigating.


Don’t make big decisions at a time of weakness


Everyone knows that hiring the right people is critical to an organization’s success. But you won’t get the best out of them unless you let them help shape your vision.

Charles Best

Founder of DonorsChoose –


Scratch a personal itch
Get out of the way and good things will follow.
Crowdsource front to back

Sara Blakely

Founder of SPANX –

For some reason, Sara’s section was covered with my highlighter. I guess I liked what she had to say. The only thing I didn’t agree with her on is not sharing your ideas in their infancy. I see her reasoning but I prefer transparency and openness. One of my favorite thing that she said is that her father used to ask her “What did you fail at today?” I am definitely using this with my future kids because it makes it clear that failure is an indication that you tried something and that you shouldn’t be afraid of failing but embrace it and learn form it.  Also, if you don’t fail then you are not trying hard enough.

…failures will eventually improve her efforts in a way that encouragement never could.


I was very clear in asking the universe to show me an opportunity and give me my own idea.

I love the following quote and completely relate to it.  I know I want to build an awesome software company and have a very specific vision for it – from the office space, to benefits to culture to the kind of people that I would hire… But I am not 100% clear on how to get there.

Whatever you can think, you can create; just have a very clear vision… I’m not clear on how I’m going to get there, but I’m 100 percent clear that I will get there.


…don’t be paranoid: ideas are almost never stolen until they’re already thriving in the marketplace.


Don’t be afraid
Courage is acting despite of fear
Hire your weaknesses

The following is another favorite quote of mine:

Money makes you more of who you already are. If you are a jerk, it will make you a bigger jerk; if you’re insecure, you will become even more insecure…


You’ve got to have the inner confidence to believe in yourself when everyone else is telling you no.

Steve Blank

A serial entrepeneur and academian –

Note to self – read The Four Steps to the Epiphany

Along with the book you are holding [The startup playbook], The Four Steps to the Epiphany should be essential reading for every startup founder.

Steve says that Joseph Campbell recognized a pattern thousands of years old that recurs in mythologies across every culture: the heroic quest. Whether it’s Moses, Luke Skywalker, or Jesus “The hero puts together a motley team to heed the call… and sets out on his quest, undergoing trials, then a death and a rebirth”.

Startup Books

I setup a Startup Books group at please join and add your books.