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.
check out the Farnam Street Knowledge Podcast episode with Jim Collins[0]. Just from the webpage there's really good ideas as excerpts from the podcast
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)
Not quite specific to entrepreneurship, but a while ago someone shared their project of a site that lists the most recommended books on hackernews [1]. The most recommended books are there for easy reference.
Blue Ocean Strategy by Renée Mauborgne and W. Chan Kim
has not been mentioned here and is an amazing read, and very well regarded by a lot of high profile folks.
As a technical founder this book on negotiation was highly valuable: "Never Split the Difference: Negotiating as if Your Life Depended on It". Negotiation is a skill you need as a startup founder that is not necessarily needed for technical work.
"Innovators Dilemma" - helps put in perspective acceptable state of early products and good strategies for deploying new innovative products
I thought that Voss's work as an FBI negotiator negated a lot of his advice. With the FBI, the building is surrounded, and the criminal is forced to negotiate with him. There are no alternatives, and there's a threat of violent action being taken against the criminal if the negotiations are refused or dont go the way Voss wants.
In business, the person on the other side has alternatives and they can walk away at any time. They don't even have to talk to you. You can be rejected because of the most minor thing or nothing at all. People say "no" all the time, and you can't send your coworkers into the building to murder them for it.
Voss just ignores the violent threat the criminal faces, and pretends the criminal is talking to him freely. But everyone in his negotiations knows every word he says is backed up with the threat of violence.
I dropped it about 2/3 through because too much of it was reading as plainly-bullshit. "I got a great deal on my truck by just saying 'how can I do that?' over and over! Here's how it went!" LOL, no you didn't, and no it didn't, and now I'm wondering whether literally any of your other stories were even a little true.
I got a very little bit out of it, but the useful bit could have been a blog post. The rest was egotistical crap that seemed to mainly be content-marketing for his business.
It's been a while and I cant remember if that was a hypothetical applying his approach to a non-criminal negotiation, or if he was saying it was a real incident... but I remember reading it, and thinking: the only way that works is if the FBI is waiting to arrest you if you refuse. If he was saying those examples were real, I agree it sounds like bullshit. It's at best, a tactic that might be rarely useful.
I'll throw in some thoughts about Never split the difference -- there's a lot of useful perspective in that book, and I appreciated it. However, speaking 'technical founderese', the book is solely about a kind of negotiation that almost never occurs in business life: a single iteration game theoretic game.
In real life, especially when you're younger than 60 and in business, every negotiation is part of an iterated game -- you are, much more than negotiating any single deal / job offer / contract term, figuring out who you want to work with, making friends and allies and partners along the way.
In those terms, most of that book is toxic, or at least sociopathic. That's fine if your only job is to get terrorists to put away their guns. But, it's definitely less fine if you are cutting a deal with someone who you will definitely intersect with multiple times in your life. And that's most people, it turns out. :)
Anyway, I think the book is super interesting, but I think technical types or those with a bit of ASD may find the relational approach hurts them more than winning any particular negotiation.
You can get all the meaning you need from The Black Swan by just reading the first few chapters. Taleb has a nasty habit of saying the same thing over and over again and stretching it out to an entire book.
"The Art of Action" It has changed how I approach everything, not just how I run my business. Is applying approaches used in militaries to organize action around the leader's intent, taking action in the right general direction, and delegating the "what" (the intent) but not the "how" of the way it is actually achieved.
From all the "business" books I've read this one is just packed with actionable advice instead of motivational gibberrish. I've built my productivized consulting offer based on these tips, and it helped me quit full-time job over 3 years ago. So far no plans to go back.
Traction by Weinberg. Understanding the distribution of your product, how to think about it and how much resources to devote to it was a missing piece for me as a technical founder. I easily fall into the fallacy of "build it and they will come" even when I don't think I do.
While I briefly ran a 'start up' with a friend (we weren't what most people here would consider a start up), we used the book 'Business Model Generation' almost weekly as we adjusted our business and pitched for new work.
I still go back to that when kicking off a new project.
Any book about org structure and incentivizing people? I always find it hard to incentivize people in a large org, and building culture is all about implementing the right incentives. Different incentives have different trade-offs, and in turn lead to different culture.
Even though it's targeted towards designers, it's actually about businesses that happen to be small design shops. The same principles apply: value your work, don't do work for free, dealing with clients, contacts, etc.
It's unconventional, because it's not strictly about businesses or startups or selling.
But if you think about, running a business is doing predictable things over and over again. Problem is, it's so complicated and there's so many things you need to take care of. Breaking them down into smallest possible steps and making habits out of them kept me moving. Write one sentence. Dial one number. Open one email. Process one invoice. It quickly snowballed.
Later, when I started scaling and delegating, I had a blueprint ready for someone else. Because they would struggle too.
And that's just a business side. The book also helped me with personal habits.
Bunch of mentions of cold start problem here already.
I at first assumed this book was just its title, and was some combination of 'launch to a lot of people in a narrow space' plus 'personal value precedes network value'.
There's actually a lot more in it, especially about the granularity of scaling at uber.
For me the book landed after I'd already tried and failed to start a network by onboarding individuals. The 'atomic networks' stuff in there is gold. (Though for someone like me who learns through failure, I needed to try everything else before the message landed).
I love seeing this on your list. Firstly because it's a great book, and secondly just because Rand is so under-appreciated in general. Especially here on HN where her name seems to be all but verboten for some strange reason.
Thanks for echoing that one, I agree. I think a lot of the dismissal of her is due to second and third-hand knowledge of what she talks about (i.e., they hate the caricature of her, not her or her ideas).
"Charles Ferguson started Vermeer Technologies and turned his very cool, very big idea into FrontPage, the first software product for creating and managing a website. A mere twenty months after starting the company, he sold it to Microsoft for $133 million, making a fortune for himself and his associates. FrontPage now has millions of users and is bundled with Microsoft Office. But getting there wasn't always fun."
It’s always funny to hear positive things about an infamously awful piece of software. Like someone would write about IE5, or Larry Ellison writing Oracle, they did irremediable harm to the world, but the people who grew when those people were young, may still have the positive initial image of them.
Lots of good suggestions here. One I don't see is Wotdke's "Radical Focus". It's about OKRs, but don't be put off by prior big-corp experiences with it. The book focuses on using them in an entrepreneurial context and it's great. Even if you decide to come up with your own system, this will help clarify what you want out of a way to set goals and make sure you're on track for them.
The Hard Thing About Hard Things. We bought a copy for every employee at my last company to help convey the messages that startups are not designed to be tons of fun but rather a tough (yet rewarding) grind. This was especially important for people who were coming from bigger companies to understand.
It's a good book, but the part where he says to collude with your friends on hiring (no poaching, no cold calling, informing the other when someone applies, etc)... that's what Google/Adobe/Apple/etc were sued for a while back. Don't do that.
Here are a few others I haven't seen mentioned.
- The Price Whisperer (pricing is important and mostly ignored by startups)
- Startup Myths and Models (title explains it)
- Measure What Matters (using OKRs)
- Growth Units (figure out your unit economics - LTV and CAC)
I've read a tall stack of business books, and in all honesty, I think only one of them was of any real value to me. It also has the benefits of being short and an easy read.
"The Incredible Secret Money Machine II" by Don Lancaster
"Built to Sell" - quick read, but transformative for me because something about it clicked with me and got me to pivot from selling "work" to selling "products"
The E-Myth is the only business book which ever left a lasting impression on me. It's about "working on your business rather than in it" and systematising everything.
Founders at Work. Just gave me a good sense of how near death and growth are just part of the game. But also tipped me to decide to move to SF Bay Area.
I am not an entrepreneur (yet) but I still want to share a few titles with you:
- "Maverick or The seven day weekend" by Ricardo Semler
- "Rework" by Jason Fried and David Hansson
- "Startup - an insider's guide to launching and running a business" by Kevin Ready
- "Bookkeeping and Cost Accounting for Factories" by William Kent (1918)
- "Practice what you preach" by David Maister
- "Don't oil the squeaky wheel" by Wolf Rinke
- "Selling The Wheel: Choosing The Best Way To Sell For You Your Company Your Customers" by Jeff Cox
- "The power of stupidity" by Giancarlo Livraghi
- "How to write a good advertisement" by Victor Schwab
- "How to Make Money Out of Thin Air" by Brian Sher
- "Good manners and business etiquette. Illustrated Guide" by Elena Ber
- "Don't just roll the dice: A usefully short guide to software pricing" by Neil Davidson
- "Message to Garcia" by Elbert Hubbard
- the TopLeaf course of 36 video lectures on management by dr. Izhak Adizes can be purchased on https://vimeo.com/ondemand/topleaf or found on ru tracker (if you have access)
The Lean Startup by Eric Ries
Zero to One by Peter Thiel
The 7 Habits of Highly Effective People by Stephen Covey
Think and Grow Rich by Napoleon Hill
The E-Myth Revisited by Michael Gerber
Good to Great by Jim Collins
The Art of Possibility by Rosamund Stone Zander and Benjamin Zander
The Hard Thing About Hard Things by Ben Horowitz
The Innovator's Dilemma by Clayton Christensen
Rework by Jason Fried and David Heinemeier Hansson
These books cover various aspects of entrepreneurship, from idea generation and innovation to leadership and management. Each one offers a unique perspective and valuable insights that can help entrepreneurs navigate the challenges and opportunities of starting and growing a business.
- Dear Founder (Maynard Webb)
- The Hard Things About Hard Things (Ben Horowitz)
- Straight Talk for Startups (Randy Komisar and Jantoon Reigersman)
- The Founders’ Dilemmas (Noam Wasserman)
- The Entrepreneur’s Daily Nietzsche (Brad Feld and Dave Jilk)
- Build (Tony Fadell)
- Zero to IPO (Frederic Kerrest)
- The Great CEO Within (Matt Mochary)
Finance
- Wharton's Introduction to Financial Accounting course: [https://www.coursera.org/learn/wharton-accounting](https://w...
- How Finance Works: The HBR Guide to Thinking Smart About the Numbers (Mihir Desai)
- Financial Intelligence for Entrepreneurs: What You Really Need to Know About the Numbers (Karen Berman and Joe Knight)
Open-Book Company (Employee Ownership, Financial Literacy, Goal-setting)
- The Great Game of Business (Jack Stack and Bo Burlingham)
Legal
- Acceleration (Ryan Roberts)
- The Entrepreneur’s Guide to Law and Strategy (Constance Bagley and Craig Dauchy)
Company Strategy and Direction (post-product/market fit)
- Crossing the Chasm (Geoff Moore)
- Zone to Win (Geoff Moore)
- Only the Paranoid Survive (Andy Grove)
- Blitzscaling (Reid Hoffman and Chris Yeh)
- The Innovator's Dilemma (Clayton Christensen)
- Good to Great (Jim Collins)
- Playing to Win (A.G. Lafley and Roger Martin)
- Tape Sucks (Frank Slootman)
- Strategy vol. 1&2 (Harvard Business Review)
Pricing
- Monetizing Innovation (Georg Tacke and Madhavan Ramanujan)
- Confessions of the Pricing Man (Hermann Simon)
Startup Phase
- The Lean Startup (Eric Ries)
- The Four Steps to the Epiphany (Steve Blank)
- Zero to One (Peter Thiel)
Management/Leadership
- The Effective Executive (Peter Drucker)
- Managing Humans (Michael Lopp)
- The Art of Leadership (Michael Lopp)
- High Output Management (Andy Grove)
- Managing Oneself (Peter Drucker)
- Essentials: Management (First Round Capital)
- The Making of a Manager (Julie Zhuo)
- The Powell Principles (Oren Harari)
- Radical Candor (Kim Scott)
- Leading Matters (John L. Hennessy) (fantastic book list in the coda)
- Turn the Ship Around (L. David Marquet) (this is THE book on delegation)
- Principles (Ray Dalio)
COO/Succession Planning
- Riding Shotgun (Nathan Bennett and Stephen A. Miles)
People Performance/HR/Culture
- Powerful (Patty McCord)
- No Rules Rules (Reed Hastings and Erin Meyer)
- Netflix culture deck
- The Five Dysfunctions of a Team (Patrick Lencioni)
- Work Rules! (Laszlo Bock)
- It Doesn’t Have to Be Crazy at Work (DHH and Jason Fried)
- The Culture Map (Erin Meyer)
- The Talent War (Mike Sarraille and George Randle)
- Great People Decisions (Claudio Fernández-Aráoz)
- The Holloway Guide to Technical Recruiting and Hiring (Ozzie Osman)
- Punished by Rewards (Alfie Kohn)
Purpose, Passion, and Self
- Start with Why (Simon Sinek)
- What You Do is Who You Are (Ben Horowitz)
- Drive (Daniel Pink)
- Mindset (Carol Dweck)
- Grit (Angela Duckworth)
- The Almanack of Naval Ravikant (Eric Jorgenson)
Fundraising/VC
- Secrets of Sand Hill Road (Scott Kupor)
- Venture Deals (Brad Feld and Jason Mendelson)
- Raising Venture Capital (Andy Sparks)
- The Business of Venture Capital (Mahendra Ramsinghani)
- Done Deals (Udayan Gupta)
- The Power Law (Sebastian Mallaby)
- VC (Tom Nicholas)
- Data-Driven Marketing (Mark Jeffery)
- Positioning (Al Ries and Jack Trout)
- Scientific Advertising (Claude Hopkins)
- Traction (Gabriel Weinberg and Justin Mares)
- Behind the Cloud (Marc Benioff and Carlye Adler)
- Ogilvy on Advertising (David Ogilvy)
- Marketing High Technology (William Davidow)
Psychology
- Influence (Robert Cialdini)
Negotiation
First, read Influence (under Psychology), then, in order
- Thinking in Bets (Annie Duke)
- Getting to Yes (Roger Fisher and William Ury)
- Never Split the Difference (Chris Voss)
- The Bald Truth (David Falk)
Self
- The 7 Habits of Highly Effective People (Stephen Covey)
Design and UX
- Creative Confidence (Tom Kelley and David Kelley)
AI (Machine Learning, Deep Learning/Neural Networks)
- The CIO Paradox (Martha Heller)
- Be the Business (Martha Heller)
Stories
- Made in America (Sam Walton)
- Shoe Dog (Phil Knight)
- The Everything Store (Brad Stone)
- Built from Scratch (Bernie Marcus and Arthur Blank)
- Hard Drive (James Wallace)
- Steve Jobs (Walter Isaacson)
- Elon Musk (Ashlee Vance)
- Creativity, Inc. (Ed Catmull)
- The Ride of a Lifetime (Bob Iger)
- Valley of Genius (Adam Fisher)
- The Idea Factory (Jon Gertner)
- Dealers of Lightning (Michael Hertzik)
- Idea Man (Paul Allen)
- Pour Your Heart Into It (Howard Schultz)
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