Most posts offer the obvious suggestions (The Mom Test, High Growth Handbook, The Personal MBA, The Power Law, Hard Thing about Hard Thing, Will It Fly, etc), so I'll focus on some non-obvious suggestions.
For tactical advice, I find talks/podcasts and mastermind groups more useful than books. My favorite podcast (by far) is Rob Walling's Startups for the Rest of Us, which is oriented towards building a capital-efficient bootstrapped business. The archive is full of extremely valuable tactical advice.
The books I've found most helpful on my entrepreneurship journey are about mental health, emotional intelligence, and relationships of all kinds. Sharing a few that have had a profound impact, since they helped me metabolize and understand what drove me to become a founder in the first place.
1. The Self-Compassion Skills Workbook by Tim Desmond
2. Path of Compassion by Thich Nhat Hanh
3. The Book You Wish Your Parents Had Read, Philippa Perry
4. Burnout, Emily Nagoski
5. Adult Children of Emotionally Immature Parents, Lindsay C. Gibson
6. Self-Compassion, Dr. Kristin Neff
7. How to Keep House While Drowning, KC Davis
8. Deploy Empathy, Michele Hansen
9. The Body Keeps the Score, Bessel A. Van der Kolk
10. Atlas of the Heart, Brene Brown
11. What Happened to You? Conversations on Trauma, Resilience, and Healing by Bruce D. Perry and Oprah Winfrey
Your last phrase hits home. At the moment, one of the things I'm very focused on is understanding why do I want to become an entrepreneur in the first place.
3. "The Four-Hour Work Week" (not because of the way of life promised in the misleading title, but because of the links to useful Websites, and for motivational reading)
4. "The One Billion Dollar App" (silly title but fantastic book from an actual taxi app product manager - I almost didn't buy it because of the title, thank God I opened it anyway and started reading about viral marketing which like the tracking of pandemic is based on the r coefficient).
5. "Business Model Generation" (the mechanics of making money)
6. "The Startup Owner's Manual"
7. "Why Startups Fail" (anti-patterns - better read about them before you get trapped by them)
8. "The Company Secretary Handbook" (UK only)
9. "Die Unternehmergesellschaft (UG): Gründung, Geschäftsführung, Recht und Steuern für kleinere Unternehmen und Start-Ups" (Germany only)
10. "Founders At Work" (motivational)
11. "Financial Times Essential Guides Writing a Business Plan: How to win backing to start up or grow your business" (to get clarity, write a plan - for yourself, to align all co-founders and the team, to get VC funding, to convince yourself that the business is financially viable)
I also think this is a must-read for would-be entrepreneurs. Probably nine times out of ten when someone tells me about their startup idea looking for advice I point them to this book first because they haven't done the basic validation yet and want to jump right into building something that no one actually wants.
I assume you're not interested in hearing the obvious ones (zero to one, lean startup, etc., etc.) so I'll recommend two.
At the early stages when you're defining your strategy? "Good strategy/bad strategy" by Richard P. Rumelt. "Strategy" is thrown around a whole lot in business, often by somebody who is talking about a goal, as opposed to how to reach it. This book can get a little repetitive but the overarching teachings are valuable and will serve you well throughout your entrepreneurship journey.
After the startup phase (growth/acquisition)? I recommend "The messy middle" by Scott Belsky.
I read The Messy Middle and thought like the chapter titles were phenomenal, but felt everything in the actual chapters was fluff. Maybe I'll give it another try!
+1 for mentioning Neil Rackham's (1988) classic "Spin Selling".
Got it recommended from a friend after his exit (and after buying a French mansion from his share of the proceeds) when I asked him what he can recommend on understanding sales, in particular sales of (complex) technology. It's indeed a marvel for people new to selling.
I don't understand how people here are recommending Zero to One and Lean Startup at the same time. They contradict each other. And in fact the Lean Startup is full of the kind of foolish post dotcom-crash thinking that Zero to One warns against.
The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function. - Scott Fitzgerald
I disagree that the two ideas are completely opposed. They both describe tools in building something. Though if I think about how Zero to One is approached, I feel it's more of a manifesto on overcoming challenges, and doing challenging things. Lean Startup focuses on how to run small experiments.
Nobody says building something challenging isn't just the process of running lots of experiments to find what works.
Systems of Engineering Management (Larson)
- Best practical advice for dealing with software engineering teams
Leading at the Speed of Growth (Catlin & Matthews)
- Despite the title making me want to vomit, it has a bunch of practical advice about problems you'll encounter at various "stages" of a company, and how to identify what stage you're in.
The First 90 Days (Watkins)
- Useful if you ever take on a leadership role where the current state of the organization could be described as a "shitshow".
Good Strategy / Bad Strategy (Rumelt)
- Learn the difference between goals and strategy and plans.
Rejection Proof: How I Beat Fear and Became Invincible Through 100 Days of Rejection by Jia Jiang
Highly enjoyable read! This book really captures the entrepreneurial experience of interviewing for insights while focusing on the fear of rejection, which is a major problem that isn't typically found in most other books on entrepreneurship.
1. "Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company" by Andrew Grove. It is a real CEO experiencing critical moments in a top company.
2. "How Life Imitates Chess" by Garry Kasparov (don't pay attention to the title...). Kasparov talks about different players with different styles and in different moments.
3. "New Directions in the Philosophy of Mathematics" edited by Thomas Tymoczko. Embed epistemological questions that at a higher level could be applied to business. In a way (2) is epistemological regarding chess and it ends when Deep Blue beats Kasparov and Kasparov start thinking in a new kind of chess called advanced chess (even if it was not successful).
4. Fred Wilson's blog, including MBA Mondays. Answers many questions from the perspective of a VC who can watch multiple companies execution at the same time and tell many humble stories.
5. "Idea Man: A Memoir by the Cofounder of Microsoft" by Paul Allen. It shows you the deep story before Microsoft, seems like a unique technological and advanced experience at that time by Bill Gates and Paul Allen. Spoiler: the lucky IBM/DOS event is not why Microsoft is successful, the book gives you some deep roots before the company foundation.
I joined their forums about 10 years ago and asked a question about a business idea. Basically I was asking about starting a gold/silver business directory thing based on some business described in the book. I was trying to understand some basics of what was being said. My post was not well received and MJ himself came in to tell me what an idiot I was.
I don't think I asked any more questions, and I left the PDF in the ash heap of my reading pile.
"Ready, Fire, Aim" by Michael Masterson. It's a bit cheesy, but it has a publishing industry slant which suited me and enough things resonated that filtered into decisions I made that I'm thankful for it. I never went it past the first half of the book as you're meant to be doing $10m revenue before you move on ;-)
“Badass: Making Users Awesome” by Kathy Sierra. I don’t see it often in lists like these. But it’s an awesome and approachable book for framing your products, services, user journey, and marketing from the viewpoint of how they’ll make your users successful and feeling amazing.
Start Small, Stay Small is one of the least fluffy books I've ever read, with tons of practical advice. It's unfortunately a bit dated, but I heard he's working on a new one.
Here are some suggestions on the more creative and less tactical spectrum.
How To Get Rich: Felix Dennis
Don’t be fooled by the title. A lifetime of insights and experience from a pioneering publishing magnate condensed into a light enjoyable read.
Creativity Inc by Ed Catmull
goes into great detail about the early days of Pixar. So many actionable lessons about entrepreneurship and operating a creative organization.
The War of Art by Steven Pressfield
Not just for artists this book is a bible for anyone who has difficulty getting out of their own way. provides useful frameworks to understand the concept of resistance and recognize negative self defeating thought patterns that many entrepreneurs struggle with.
The concept of Resistance put forward by Pressfield in the book The War of Art is very profound and practical. I have this book summary hanging on my wall. Gets me up every time I feel like not wanting to do the grunt work.
I like books that are actionable. Lots of books are inspirational but not that useful (e.g. crossing the chasm). I run a curriculum in my company which uses a few books I have read over the years.
emyth revisited (how to think about and structure an org)
getting to yes (negotiation)
influence the psychology of persuasion (negotiation)
spin selling (enterprise sales, supplanted by sandler)
You cant teach a kid to ride a bike at a seminar (sandler sales)
5 dysfunctions of a team (one of the best leadership books)
[+] [-] grepLeigh|3 years ago|reply
For tactical advice, I find talks/podcasts and mastermind groups more useful than books. My favorite podcast (by far) is Rob Walling's Startups for the Rest of Us, which is oriented towards building a capital-efficient bootstrapped business. The archive is full of extremely valuable tactical advice.
The books I've found most helpful on my entrepreneurship journey are about mental health, emotional intelligence, and relationships of all kinds. Sharing a few that have had a profound impact, since they helped me metabolize and understand what drove me to become a founder in the first place.
1. The Self-Compassion Skills Workbook by Tim Desmond
2. Path of Compassion by Thich Nhat Hanh
3. The Book You Wish Your Parents Had Read, Philippa Perry
4. Burnout, Emily Nagoski
5. Adult Children of Emotionally Immature Parents, Lindsay C. Gibson
6. Self-Compassion, Dr. Kristin Neff
7. How to Keep House While Drowning, KC Davis
8. Deploy Empathy, Michele Hansen
9. The Body Keeps the Score, Bessel A. Van der Kolk
10. Atlas of the Heart, Brene Brown
11. What Happened to You? Conversations on Trauma, Resilience, and Healing by Bruce D. Perry and Oprah Winfrey
[+] [-] Gooblebrai|3 years ago|reply
Your last phrase hits home. At the moment, one of the things I'm very focused on is understanding why do I want to become an entrepreneur in the first place.
[+] [-] jll29|3 years ago|reply
2. "Spin Selling" (sales)
3. "The Four-Hour Work Week" (not because of the way of life promised in the misleading title, but because of the links to useful Websites, and for motivational reading)
4. "The One Billion Dollar App" (silly title but fantastic book from an actual taxi app product manager - I almost didn't buy it because of the title, thank God I opened it anyway and started reading about viral marketing which like the tracking of pandemic is based on the r coefficient).
5. "Business Model Generation" (the mechanics of making money)
6. "The Startup Owner's Manual"
7. "Why Startups Fail" (anti-patterns - better read about them before you get trapped by them)
8. "The Company Secretary Handbook" (UK only)
9. "Die Unternehmergesellschaft (UG): Gründung, Geschäftsführung, Recht und Steuern für kleinere Unternehmen und Start-Ups" (Germany only)
10. "Founders At Work" (motivational)
11. "Financial Times Essential Guides Writing a Business Plan: How to win backing to start up or grow your business" (to get clarity, write a plan - for yourself, to align all co-founders and the team, to get VC funding, to convince yourself that the business is financially viable)
[+] [-] alex_lav|3 years ago|reply
[+] [-] diehell|3 years ago|reply
[+] [-] ary|3 years ago|reply
https://a.co/d/8KzUk8b
It ended up saving us a lot of time.
[+] [-] andrewmutz|3 years ago|reply
[+] [-] mdorazio|3 years ago|reply
[+] [-] jereze|3 years ago|reply
[+] [-] dmkirwan|3 years ago|reply
At the early stages when you're defining your strategy? "Good strategy/bad strategy" by Richard P. Rumelt. "Strategy" is thrown around a whole lot in business, often by somebody who is talking about a goal, as opposed to how to reach it. This book can get a little repetitive but the overarching teachings are valuable and will serve you well throughout your entrepreneurship journey.
After the startup phase (growth/acquisition)? I recommend "The messy middle" by Scott Belsky.
[+] [-] hkhanna|3 years ago|reply
[+] [-] collin128|3 years ago|reply
Highly recommend the book.
[+] [-] shw1n|3 years ago|reply
The Personal MBA - crash course MBA
Founders At Work - understanding how different startups survived
Buy Back Your Time - management and delegation
The Charisma Myth - to help w/ charm for sales
SPIN Selling - this + The Charisma Myth more than doubled our sales conversion rate
These books were the most crucial for me
[+] [-] wpietri|3 years ago|reply
[+] [-] jll29|3 years ago|reply
Got it recommended from a friend after his exit (and after buying a French mansion from his share of the proceeds) when I asked him what he can recommend on understanding sales, in particular sales of (complex) technology. It's indeed a marvel for people new to selling.
[+] [-] herodoturtle|3 years ago|reply
I've read countless books on this topic.
The book that helped me the most was "Good to Great" by Jim Collins.
It has memorable nuggets of advice, summarised neatly into insightful chapters.
Once you learn these nuggets you never forget them, and you end up leveraging them regularly in your day-to-day entrepreneurial decisions.
It's a bit like Covey's 7 Habits book, but geared for entrepreneurs wanting to grow a successful business.
Good luck on your journey. It's tough, but worth it.
[+] [-] harryvederci|3 years ago|reply
[+] [-] samhsmith|3 years ago|reply
[+] [-] pedalpete|3 years ago|reply
I disagree that the two ideas are completely opposed. They both describe tools in building something. Though if I think about how Zero to One is approached, I feel it's more of a manifesto on overcoming challenges, and doing challenging things. Lean Startup focuses on how to run small experiments.
Nobody says building something challenging isn't just the process of running lots of experiments to find what works.
[+] [-] dadrian|3 years ago|reply
Leading at the Speed of Growth (Catlin & Matthews) - Despite the title making me want to vomit, it has a bunch of practical advice about problems you'll encounter at various "stages" of a company, and how to identify what stage you're in.
The First 90 Days (Watkins) - Useful if you ever take on a leadership role where the current state of the organization could be described as a "shitshow".
Good Strategy / Bad Strategy (Rumelt) - Learn the difference between goals and strategy and plans.
[+] [-] manv1|3 years ago|reply
It goes over the various sales channels. How you get customers should really be the #1 priority for your startup.
Building stuff is easy. Getting customers is hard. And "if you build it they will come" doesn't really work most of the time IRL.
[+] [-] notsure357|3 years ago|reply
Highly enjoyable read! This book really captures the entrepreneurial experience of interviewing for insights while focusing on the fear of rejection, which is a major problem that isn't typically found in most other books on entrepreneurship.
[+] [-] wslh|3 years ago|reply
1. "Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company" by Andrew Grove. It is a real CEO experiencing critical moments in a top company.
2. "How Life Imitates Chess" by Garry Kasparov (don't pay attention to the title...). Kasparov talks about different players with different styles and in different moments.
3. "New Directions in the Philosophy of Mathematics" edited by Thomas Tymoczko. Embed epistemological questions that at a higher level could be applied to business. In a way (2) is epistemological regarding chess and it ends when Deep Blue beats Kasparov and Kasparov start thinking in a new kind of chess called advanced chess (even if it was not successful).
4. Fred Wilson's blog, including MBA Mondays. Answers many questions from the perspective of a VC who can watch multiple companies execution at the same time and tell many humble stories.
5. "Idea Man: A Memoir by the Cofounder of Microsoft" by Paul Allen. It shows you the deep story before Microsoft, seems like a unique technological and advanced experience at that time by Bill Gates and Paul Allen. Spoiler: the lucky IBM/DOS event is not why Microsoft is successful, the book gives you some deep roots before the company foundation.
[+] [-] erybodyknows|3 years ago|reply
[+] [-] all2|3 years ago|reply
I don't think I asked any more questions, and I left the PDF in the ash heap of my reading pile.
[+] [-] petercooper|3 years ago|reply
[+] [-] rigmarole|3 years ago|reply
[+] [-] im_down_w_otp|3 years ago|reply
[+] [-] scop|3 years ago|reply
[+] [-] mindcrime|3 years ago|reply
The Discipline of Market Leaders - Fred Wiersema and Michael Treacy
It's Not the Big that Eat the Small...It's the Fast that Eat the Slow - Jason Jennings
Mastering The Complex Sale - Jeff Thull
How To Measure Anything - Douglas Hubbard
[+] [-] joshmanders|3 years ago|reply
Company of One by Paul Jarvis
[+] [-] davidw|3 years ago|reply
[+] [-] bikeformind|3 years ago|reply
How To Get Rich: Felix Dennis
Don’t be fooled by the title. A lifetime of insights and experience from a pioneering publishing magnate condensed into a light enjoyable read.
Creativity Inc by Ed Catmull
goes into great detail about the early days of Pixar. So many actionable lessons about entrepreneurship and operating a creative organization.
The War of Art by Steven Pressfield
Not just for artists this book is a bible for anyone who has difficulty getting out of their own way. provides useful frameworks to understand the concept of resistance and recognize negative self defeating thought patterns that many entrepreneurs struggle with.
[+] [-] bhu1st|3 years ago|reply
[+] [-] achenatx|3 years ago|reply
emyth revisited (how to think about and structure an org)
getting to yes (negotiation)
influence the psychology of persuasion (negotiation)
spin selling (enterprise sales, supplanted by sandler)
You cant teach a kid to ride a bike at a seminar (sandler sales)
5 dysfunctions of a team (one of the best leadership books)
first break all the rules (management)
accounting for dummies
purple cow (differentiation)
blue ocean strategy (differentiation)
traction (strategy/operations)
rocketfuel (strategy/operations)
for professional services:
managing the professional services firm
getting naked
[+] [-] jackconsidine|3 years ago|reply
In sort of curriculum order:
- Built to Sell - really easy gateway
- The E-Myth Revisited (withstand the writing style, glib observations)
- The Business Model Generation book- massive leap in understanding after this
- Traction (Gabriel Weinberg). Marketing entrypoint zeroed into today
- Managing the Professional Service Firm (Maiser) (incidentally related to what I do but so useful)
- Thinking in Systems (Meadows)
- An Elegant Puzzle (Engineering management book by Will Larson. Actionable and bite-sized)
- Measure What Matters (Doerr)
- Crossing the Chasm
- Blue Ocean Strategy
- Never Split the difference (eh)
- Design of everyday things (not as niche as I thought, perspective altering)
Some sales books (I held my nose while reading, but useful insights)
- The Science of Selling
- S.P.I.N. Selling
- The Challenger Sale