14 Books Every Bootstrap Startup Founder Must Read
I consider myself an autodidact. I’m not saying this to brag. I was just never a great student. Structured classroom learning really never worked for me ever since I was a little kid.
But I did love to learn, and the art of self-learning came very natural to me. I remember even in elementary school, textbooks were more engaging to me than the classroom setting. Since I usually just relied on the textbooks, I often found myself being weeks, or even months, ahead of whatever was being taught in class. Sadly, from probably 4th grade thru high school (even through most of college)…I don’t actually remember learning much from class or teachers at all, but I do remember learning most everything from books.
I think my dad saw this problem in me early in life…cause he continually drilled into me, “if you don’t know something…just ask someone.” It was a mantra he continually repeated. He didn’t want me to merely rely on books…he wanted me to learn from people. This quickly became the second most important lesson as an autodidact.
The knowledge gained from just being intentionally inquisitive with people was transformational throughout my life. This practice also started at a young age. It became such a huge part of my self-learning approach that I often have to catch myself in social settings…cause a lot of times, I merely saw people as these rich vats of information and knowledge, just waiting to be drained dry. I’ll admit, it’s not a pretty image…me as some sort of vampire and people as my food. I’ll contend though that in practice, it often builds great relationships. People generally love to share knowledge and be helpful…and finding a conversational commonality over their area of expertise is typically welcomed.
As an adult, I finally realized that both reading and directly learning from experts is a powerful combo. You see, when you talk to people about their expertise, the conversations are fairly shallow and useless when you have zero knowledge about that subject. The expert usually just dumbs down the conversation to a degree that’s typically not very interesting. But, when you expose that you have just the slightest amount of subject proficiency…I’ve found that the level of conversation usually increases by 10 fold. This deeper level of conversation is typically where all the critical and nuanced learning takes place.
This is just natural human behavior, and I’m guilty of it as well. When someone asks me about product or UX design who knows nothing about it…those conversations usually lasts several minutes. When someone demonstrates that they can engage in even the slightest amount of intelligent dialogue about product or UX design…well, those conversations usually lasts several hours.
Sorry for the long-winded intro, but this is where the recommended reading list comes in. Over the years, for each of the subjects listed below…I’ve asked industry experts what they consider as their industry “bible”. Surprisingly, for most disciplines, there is usually just 1 or 2 standout books that represents that industry extremely well. It sounds a bit brazen and perhaps insulting to the industry professionals for sure…but I contend that reading from the list below can actually make you extremely well-versed in that field. It’s like the 80/20 rule…most of the core concepts in any particular field can be summed up quite simply.
I’ve collected and read the many books industry experts have recommended over the years, and whittled them down to a hopefully useful set below. Below are the key subjects every bootstrap entrepreneur need to know about. Reading these books should be able to give you enough foundational knowledge to hold intelligent conversations with industry experts…and then really ramp up your learning.
Would love to hear your thoughts and additions to the list in the comments.
General Business
The Innovator’s Solution
Clayton Christensen
This is perhaps my favorite business book of all time. The ideas in this book are based on years of research across hundreds of companies. Christensen presents extremely well thought out ideas on how to innovate for disruption…and even how to protect your business from being disrupted from entrants.
Product Development
The Lean Startup
Eric Ries
I consider this a book that started a movement, for both startups and large corporations. If there’s one book that I’d make my entire team read…it’d be this one. It’s just helpful getting the team on the same page, understanding the pervasive ideologies preached in this book, and even using the same jargon often utilized in many startup teams because of this book.
Product Management
Shipping Greatness
Chris Vander Mey
This is a hugely underrated book that tops my personal list as a seasoned product manager. Written by an former Google and Amazon PM, he shares all the product management processes he’s found success with at these two great companies. I almost don’t want to share this book cause most of my personal product management playbook and secrets is very consistent with what’s written here. Extremely easy to read and very practical advice.
Product Design
Hooked: How to Build Habit-Forming Products
Nir Eyal
This book reveals well researched thoughts on what makes consumers tick, and how to design great products for this consumer psychology. This is a must read for any bootstrapper developing a digital product.
UX Design
Don’t Make Me Think
Steve Krug
This book has been around since 2000, and has helped pioneer the field of UX design ever since it was published. Now on it’s 3rd edition, this is probably the one book that’s required reading for every single UX course out there…no exaggeration. It’s super simple to read that even a novice would find it engaging and useful. I definitely also recommend his other book, Rocket Surgery Made Easy…which I actually enjoy even more, as it reveals very practical advice on usability testing.
Software Development
Getting Real
Jason Fried, Heinemeier David Hansson
This is probably the first book I read about startups, and it got me hooked. I still remember reading it when 37signals first published it. They gave it away as a free PDF download (which they still do), I downloaded it at night, and I stayed up all night to finish it. The next day, I read the whole book again. I’ll admit, this book was extremely influential to my ideologies on software development…then and now. Just like The Lean Startup, this would be one of the few books on my entire team required reading list…not just the engineering team.
Project Management
Scrum: The Art of Doing Twice the Work in Half the Time
Jeff Sutherland
I’ve been a long term believer and practitioner of Agile and Scrum project methodology. In my experience, using Scrum has helped me accomplish more than any other process management system I’ve ever used. This book is written by one of the father’s of Scrum, Jeff Sutherland…and the principles presented is easy to follow, easy to implement, and highly applicable.
Growth
Traction
Gabriel Weinberg
Depending on who you ask, growth hacking is either the most important thing for a startup…or it’s merely a buzzword. It’s probably one of the most misunderstood startup/business concepts today. Definitely pick up a couple books on growth hacking, including this one called “Traction”. The thing I like about this book is it’s a great primer on a very comprehensive list of potential growth channels to explore. Of course, each channel discussed in this book can have volumes of books written about them…but they’ve put enough concepts in there to help you get started with experimentation.
Sales
Predictable Revenue
Aaron Ross
Who better to learn sales from, than from one of early sales leaders at Salesforce. Time and time again, every blog I read, every podcast I hear about sales…I hear undertones of Predictable Revenue at the core of every strategy. It’s a playbook that goes through every piece of the sales funnel in detail. I admit, I haven’t thought through if this is applicable to every startup business out there, but if your startup is a SaaS business, then this is a must read.
Marketing
The Sales Acceleration Formula
Mark Roberge
This was a tricky choice, choosing this book to represent marketing. Just looking at the title alone would seem it would fall under sales, and arguably, this would probably be one of the top all-time book on sales as well. The reason I chose this to represent marketing is because it does truly bridge the gap between inbound marketing efforts and sales. The proof of this methodology is in Hubspot’s own growth results, where the author, Mark Roberge, served as SVP of Sales. Honestly though, the perfect one-two combo would be reading this book along with Inbound Marketing, by Brian Halligan and Dharmesh Shaw, the founders of Hubspot.
Branding
The Brand Gap
Marty Neumeier
This is the book that started me thinking, that for every profession, there’s really only 1 or 2 books you need to make you well versed in that field. Many years ago, I asked a very seasoned brand expert how to learn more about branding. He literally pulled me aside as to tell me a secret, and he said just read The Brand Gap and Marty Neumeier’s other books in that series…and you’ll basically know as much as I do. When I picked up the books, I was shocked. It was short, it was easy to read, and it was very good. As mentioned, definitely pick up his other 2 books Zag and The Designful Company.
Customer Service
Delivering Happiness
Tony Hsieh
Wasn’t sure whether to categorize this book under customer service or corporate culture. Perhaps that’s the point, as the CEO of Zappos, Tony Hsieh, reveals the playbook behind Zappos’ legendary customer service. When you consider that Zappos is basically just an online shoe store, that somehow sold to Amazon for $1.2 billion…there must be something pretty remarkable going on there. Also, this isn’t just an autobiography or a company story…it’s actually a fairly detailed account on how they view and run a customer driven organization.
Startup Entrepreneurship
Do More Faster
Brad Feld, David Cohen
Who better to learn startup entrepreneurship from, than from two guys who’ve invested in and seen the startup journeys of hundreds of startups. The Authors, Brad Feld and David Cohen, founded Techstars, one of the top startup accelerators in the world. In this book, they share basically every major challenge you might encounter as a startup founder. Even though it’s written primarily for angel/VC backed startups, I’d still recommend it to any bootstrap entrepreneur. The advice is extremely practical, and you also hear direct perspectives from startup entrepreneurs interspersed in the chapters.
Extra Credit
Predictably Irrational
Dan Ariely
Behavioral economics is one of the most interesting fields to me. I put this under “extra credit” because it’s just generally useful to know what makes people tick and act the way they do. It can come in handy in UX design, marketing, sales, contract negotiations, business development…basically anything that deals with people. If you have the time and patience for a deep read, I’d recommend Thinking Fast and Slow. That’s probably regarded as the bible for behavioral economics, but it’s a real heavy read. Predictably Irrational is a bit more consumer friendly, easier to read, yet still extremely insightful.
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