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.

The Lean Startup Movement’s Guidebook: The Lean Entrepreneur

I was lucky enough to get an advanced copy of the Lean Entrepreneur* and have been reading it on my commute for the past few weeks. After having spent time reading many other Lean books and blog posts, I’m excited to see this book released. In the interest of keeping a review MVP, here’s why you should, and shouldn’t read this book:

Reasons to Read the Lean Entrepreneur:

1. You’re not fully convinced to use Lean.

This book is like an FAQ on Lean. It beats down all the stereotypes (like Lean is only for software) with specific examples and thoughtful explanation.

2. You want to hear real life case studies of Lean in action.

The authors went to great lengths to get great case studies from everything from hardware companies to commercial cleaning products to prove that you can apply lean to *any type of business*.

3. You want help evaluating how you’re really doing at being Lean. 

One of the best things about this book is that between the concepts and case studies are a ton of checklists that help you see if you’re really properly evaluating your company at each step of the lean process.

Reasons to Not Read the Lean Entrepreneur:

1. You are already a 100% lean practitioner.

I’ve been doing lean basically full time for 3.5 years now and I still learned a lot. You’re bound to learn a few new things.

2. You like detailed, helpful diagrams and pictures.

Sorry, I know we’re all supposed to love @FakeGrimlock, but I’m underwhelmed by his drawings. I don’t think his drawings added much to the book or were helpful other than to give the book a lighter, more accessible feel.

3. You were hoping for the nitty-gritty details of exactly what to do.

This book won’t help you write your customer development interview script (here’s a post for that) nor help you find the phone numbers of your customers. What it will do is answer the critics’s questions and get you asking the right questions about your business.

Overall, I thought this was a solid book that adds a lot to the conversation of the evolving Lean Startup movement. I read a lot of books and this falls in at a 7.5 on my rating scale.

It goes much further and deeper into how to approach actually doing Lean in your business than Eric Ries’s The Lean Startup book. I hope that some of the people at companies with case studies in the book will share some more tactical advice that didn’t fit in this book.

The Lean Entrepreneur came out today. You can dive into Lean best practices and get your copy here.

*Disclosure: Patrick Vlaskovits is a friend of mine and he asked me to review his book.

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?

Why you should take your 20s seriously

“Don’t take life too seriously, you’ll never get out alive.” – Van Wilder

It seems like the prevailing advice today for anyone in their twenties is to live their lives free of any commitments and as independent and undirected as possible.  As a workaholic entrepreneur since I finished school, it never really resonated with me, but even I have found myself prioritizing based on the fact that my 20s are unique time I can do things I wouldn’t be able to any other time in my life.

A friend recently recommended I read The Definining Decade: Why your twenties matter – and how to make the most of them now. After reading it, I realized the importance of my twenties to a degree I never had and it has changed how I plan to approach the last few years of my 20s.

Written by a clinical psychologist, the book hits on all the key aspects of your life: Work, Love and your Body. There are many great takeaways, but the 3 biggest that have stuck with me are:

1) Your 20s lay the groundwork for success in the rest of your career.

Whether you’ve spent too much time as a bartender or waitress or in tech living in your parent’s basement as you “work on your startup”, you could be preventing your life from moving forward in a way that will make you successful and happy in the future.

Maybe Starbucks is enough to be happy now, but can you raise a child with that pay? More importantly, do you want to be doing exactly what you’re doing now in 10 years? If not, does your current job get your foot in the door?  If you aren’t Mark Zuckerberg, maybe you should think about how to build a career in a startup as opposed to being a young, fledgling founder forever.

No one starts at the top. It starts with a dues-paying low level job where you excel and get more and more opportunities. I had a master’s degree and still had to start with a part time internship to get my foot in the door in tech. That internship led to the person I interned for getting me a full time job at a startup they were on the board of. The founder of that company then introduced me to Hiten Shah as a mentor and now I run product for his company, KISSmetrics. This is how most successful people I know have built their careers, and it always starts small.

Lesson: Don’t put off starting to build a career. The sooner you start out in an industry and role you like, the sooner you can grow into a satisfying career.

2) Statistically, women need to have all their children by 35.

According to the author, a woman’s ability to get pregnant plummets starting in her mid-thirties. To make matters worse, the odds of a miscarriage for a woman over 35 is one in four.  This is a scary statistic that brings images to my mind of a couple struggling to get pregnant only to lose their child during pregnancy. No one wants that.

The thought of a family has been far from my mind all through my 20s. I’ve put my career goals ahead of everything else.  At the same time, I’ve known I do eventually want to have a family. Realizing these statistics has led me to better understand the choices I make and the time I’m working against. It now makes a lot more sense why there’s so many founders in their early 30s that have started families.

Lesson: If having a family is part of your life’s goals, you probably have less time than you think. If you’re a guy that wants to marry a woman relatively the same age as you, the clock is ticking on you just as much as it is for her.

3) Your brain finishes forming in your 20s.

I always thought your mind was formed as a child and that by the end of your teens your brain was probably what it was going to be until the decline began in your 30s or 40s. As it turns out, your frontal cortex goes through great change in your 20s before it is set more permanently in your 30s (imagine wet concrete hardening). Per Wikipedia,

The executive functions of the frontal lobes involve the ability to recognize future consequences resulting from current actions, to choose between good and bad actions (or better and best), override and suppress unacceptable social responses, and determine similarities and differences between things or events.

As a person whose goal is build a massive company, I realize I need to develop as many of the skills I need to lead such a company now, because in a few years it may be difficult or almost impossible to grow in the ways necessary to handle the role. As I hear about founders that can’t (or don’t want to) run a company once it reaches a certain size, I think about the challenges of scaling yourself and the development required.

Lesson: Whatever your career and life goals, realize that the skills you develop and the personality you forge in your 20s will determine many of your abilities the rest of your life.

Few books I’ve read have led to as much personal introspection as reading this one. If these concepts interest you, I highly recommend you check out: The Definining Decade:

11 Books Every Entrepreneur Should Read

On Amazon.com there are…

…over 2,000,000 books on “Business”

…over 750,000 books on “Technology”

…over 500,000 books on “Design”

…over 81,000 books on “Leadership”

…over 7,500 books on “Startups”

…and most of them suck. 

So even if you want to commit to reading books to make yourself a better entrepreneur, what are you to do?

Over the last 3 years, I’ve read over 60 books on a variety of subjects to try to better my own entrepreneur knowledge base (see the sidebar on the right for the full list).  Every book came from at least one recommendation from a friend, a tweet from an expert or a blog post explaining why it’s great. Because of this, very few of the books I’ve read would fit in the “waste of time” category most of those 3 million or so books on Amazon fit into. A lot of my friends have asked for what I think are the essential books I’d recommend, so here’s that list.

11 Books Every Entrepreneur Should Read

How to Win Friends and Influence People by Dale Carnegie

Category: Leadership

Why You Should Read This: There is no book more successful people I know have read than this one. 

Being a leader is not easy. No matter how natural a great leader makes it look, it takes a lot of work to learn how to build relationships and inspire others on a regular basis. How to Win Friends and Influence People will teach you what you need to succeed.

Most importantly, the book is specific, it’s actionable and filled with solid example stories to help emphasize the rules. I’ve re-read this book at least 5 times and every time I learn something I could improve.

The Alchemist by Paulo Coelho

Category: Inspirational

Why You Should Read This: This book explains all those strange feelings you have that make you want to throw away a cushy life, a nice salary and the life you’re “supposed to follow” and live the uncertainty of the startup life.

It won’t teach you how to incorporate your business or market your product. It will teach you how to make sense the of the journey you’ll go on if you follow your heart.

Founders at Work by Jessica Livingston

Category: Startups

Why You Should Read This: The journey in building a startup is far from glamorous. As many have written before, over night successes are usually years of pain in the making.

Founders at Work captures this essence with stories of entrepreneurs anyone in the web and mobile startup space will recognize. It’s a great primer to understand how dark some of the dark days can get in a startup and how the best persevered.

The Entrepreneur’s Guide to Customer Development by Patrick Vlaskovits & Brant Cooper

Category: Lean Startups

Why You Should Read This: Want to stop guessing and start actually figuring out what your customers/users actually want? Want to not waste your time, money, energy and life on a startup no one cares about? There’s tons of blog posts, books and other content out there on Lean Startups, but nothing distills it down to its core concepts and action items like Patrick & Brant’s book does.

This book will get you 80% of the way there on understanding and taking action on Lean Startup methodology and you can read this book in an afternoon. It’s such an easy and important read, you should have everyone in any role at your startup read it in my opinion.

Switch by Chip and Dan Heath

Category: Culture, Leadership

Why You Should Read This: You can only get people to do things they want to do.  If you force them to do it, they won’t do great work and will quit the first chance they get. Chip and Dan explain how you can inspire your team and get them to accomplish major goals even when things look bleak.

They introduce the concept of the Elephant and the Rider which is an invaluable metaphor for the human pysche in both your employees and your own life.

The Master Switch by Tim Wu

Category: Technology

Why You Should Read This: “Every age thinks it’s the modern age, but this one really is.”  Dating back to the days of Western Union telegrams in the late 1800s, The Master Switch discusses what happens when a new technology emerges and disrupts the status quo. Without fail, it always involves the existing players fighting to hold back the technology until they’re crushed.

You may think that all of this has only happened more recently in the age of computers, but this is a battle that has repeated itself for generations.  In particular, you’ll find that Twitter is surprisingly similar to AT&T when Alexander Graham Belle built his early empire. Instead of APIs and shutting down developers though, AT&T literally cut phone lines and physically attacked rival, small phone companies. This book will help put into perspective what happens during these cycles of disruption.

The Mating Mind by Geoffrey Miller

Category: Psychology

Why You Should Read This: Not that long ago, our world was driven by a purely tribal culture. Lives were simple and our evolutionary habits were driven towards survival. Today, those same instincts still exist, but they’re in a foreign world where many actually do us a disservice at worst or at least make us less predictable than you’d expect.

You should understand your customer better than they understand themselves. This book will help you understand people in ways you wouldn’t expect. You can’t put a price on the insights it can give you as you position your product and design it effectively.

The Design of Everyday Things by Donald A. Norman

Category: Design

Why You Should Read This: Many of my design friends have recommended this as the seminal book on design. Upon reading it, I can see why. The book focuses on explaining what great design really means with a lot of great examples with images.

Everyone today is focused on simplicity, but the real word that matters is intuitive. Norman asserts that the functionality of a product should be obvious based on the design of the product. While all of his examples are physical items like stoves and door handles, it’s easy to see how it should impact the layout of your site.  After reading this book, you will never look at doors the same way again.

Crucial Conversations by Patterson, Grenny, et al

Category: Leadership

Why You Should Read This: Ever have a discussion devolve into a shouting match? Ever have a debate where you realized you and your opponent were actually in agreement? Do you wish you could get someone to open up to you, but they’re being icey cold? Crucial Conversations does exactly what the title suggests: it teaches you how to handle the tough, important conversations.

As entrepreneurs, we’re confronted with difficult conversations every step of the way from investors to cofounders, partners to employees. Then you go home and have to try to maintain a relationship with a spouse, significant other or roommate. This is a skillset you can’t afford not to have…unless you love stress, tension and resentment towards you.

Tribal Leadership by Dave Logan

Category: Leadership, Culture

Why You Should Read This: Making a great culture at your company is one of the hardest things to do at your startup, especially as it grows. Even harder is finding a decent book that actually helps you build that culture.

Tribal Leadership will help you understand how every person is doing in your company and how to raise their game to become a greater contributor and part of a truly great team.

When I joined KISSmetrics, I strongly encouraged Hiten, our CEO to read it and he loved it so much he got copies for the entire team and had us spend significant time discussing it.  Since then, the whole company has had discussions on the stages we’ve all been in and we can see the impact positive actions have had.

What Every Body is Saying by Joe Navarro

Category: Psychology

Why You Should Read This: There is a language every human speaks that most people not only cannot understand, but they don’t even realize they’re speaking: body language.

Being able to read body language is huge for any entrepreneur as it gives them a leg up on negotiations, reading their employees for warning signs (or positive signs) and better detecting when something is shady.  This book is written by an ex-FBI agent who did this for a living and it does not disappoint.

I cannot put a price on what I learned from this book as I’ve seen it show when a CEO has lost their staff, when coworkers aren’t buying into something I’m sharing and reading when a person is truly interested in me and my ideas.  Don’t spend another day missing both the obvious and subtle signals people are sending you. Most are involuntary, which means they’ll be more truthful than the words coming out of their mouths.

I believe these books will give you a well-rounded view of the skills you need as an entrepreneur and in their category, they’re the best.

What books do you recommend most?

Book Review: Founders at Work

A startup has the most uncertainty in the beginning. You have no customers. Your team may be incomplete. You may not even fully understand what your market is or even your product. If you’re an entrepreneur, you’re either in this situation now, or you’ve been there before.

Jessica Livingston’s book, “Founder’s at Work” profiles some of the most famous startups of the past few decades (and some you didn’t know) by interviewing founders and asking them what the “early days” were like.

Despite hearing stories from 32 different companies, ranging from hardware to software to consumer web, there were a few common themes I noticed throughout:

1) You’re idea will change.

Whether it was PayPal, Apple, or 37 Signals, where you start out may not be where you finish.  Paypal originally thought they’d manage transactions on the Palm Pilot. 37 Signals was original a web development consulting firm. Apple thought they’d sell some kits to computer hobbyists.  We all know how all those turned out. Don’t be surprised if your startup experiences the same thing.

2) Not every great business knows how they’ll make money from the start.

Blogger, Trip Advisor (an exhibitor at the Career Combine!) and many others struggled greatly with finding the right revenue model.  Does that mean we should all adopt the Underpants Gnomes business model? No. But it does mean that you should be open to adapting and trying multiple revenue opportunities.  Trip Advisor even went as far as walking away from some deals when they decided a different path was the best model, even though it was unproven and would take longer to bring in revenue.

3) Choosing the right investor is important.

There are a few horror stories of when bringing in investment money was a disaster. Most notably, ArsDigita went from a growing profitable business to infighting and self-destruction after taking VC investment. There were also stories of where investment worked out fine.  I think the key is to remember that the people who you take investment from are you partners for the life of the business. You can fire co-founders, divorce your wife, but investors are forever.  Choose people you feel comfortable working with and trust.

4) Every company has its Dark Days.

One question that Jessica seemed to make sure to ask every founder was if they ever “thought about quitting.”  Most responded with stories of their darkest days, when they weren’t sure they were going to make it, that they had to fire a friend or when a key deal fell through.  Fortunately, everyone interviewed stuck with it, which is why their businesses were successes and they were profiled in a book like this.

I think the biggest lesson I learned from all of the stories was just that you need to be insanely passionate about your business; it’s going to be hard, there will be setbacks and only persistence and diligence will give you a chance* at succeeding.  If you can see yourself not doing your business, then you may want to save yourself the torture of uncertainty and long hours.

If you’re starting a business or thinking about it, this is a great book to give you an idea of what it’s really like in the early days.