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The Top 22 Books Every Entrepreneur Must Read

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These 22 Amazing books have been compiled by various reviews and have come out on top as the 22 Best Books that every Entrepreneur Must Read.

Have you read any of these books yourself? If not, get your hands on a few of these and increase your skills for success in the world of Entrepreneurship.

 

The Top Entrepreneur Books:

“The Fountainhead” by Ayn Rand

Charlie O’Donnell: “I don’t know any book that sums up the entrepreneurial passion and spirit better than The Fountainhead by Ayn Rand: ‘The question isn’t who is going to let me; it’s who is going to stop me.'”

 

“Out of the Crisis” by W. Edwards Deming

Roger Ehrenberg: “Big or small, this book focuses the entrepreneur/manager on respecting employees, focusing on process, and insisting on the collection and analysis of data. The development of metrics to manage the business is critical for the start-up founder.”

 

“Extreme Programming Explained” by Kent Beck

Babak Nivi: “Revelatory. Develop your product like this book tells you to, unless you know better (e.g. you have experience building operating systems, space shuttles, Googles.) Buy the first edition.”

 

“The Four Steps to the Epiphany” by Steven Gary Blank

Babak Nivi: “The closest thing to a manual for building a startup. Marc Andreessen calls it ‘a roadmap for how to get to Product/Market Fit.'”

 

“Reality Check” by Guy Kawasaki

Penelope Trunk: “I love flipping through the chapters. Each one is like a blog post, so you learn something on every page. And each chapter reminds me to be a little bit better at something I’m doing already.”

 

“Peak” by Chip Conley

Fred Destin: “Maslow’s hierarchy of needs adapted to the business world.  Not that well written (sorry Chip) but sound advice on achieving ‘sustainable outperformance’ and leveraging crises for the better.”

 

“The Happiness Hypothesis” by Jonathan Haidt

Fred Destin:  “Not a business book, but if you assume self-awareness and knowing what you are really good at are key to success in business (and life in general), this is the best attempt I have read at deriving ‘meaning’ from the joyous mess of life.”

 

“Against The Odds” by James Dyson

Jason Fried: “One of the best books about design, business, invention, and entrepreneurship I’ve ever read. Highly recommended. It’s really inspirational. His persistence is otherworldly. You won’t believe what he went through to get this product to market.”

 

“How To Get Rich” by Felix Dennis

Greg Galant: “The self-made billionaire founder of Maxim Magazine and The Week titles this book as though it’s a snake oil self-help book. It’s really a great entrepreneurial memoir with British wit at its finest.”

 

“Transparency: How Leaders Create a Culture of Candor” by Warren Bennis, Daniel Goleman, and James O’Toole

Nilofer Merchant: “The future is invented not in the easy conversations but in the hard ones. We’ve got to know how to have and manage those conversations that lend light and transparency to WHY we are doing what we are doing. This book emphasizes how leaders create a culture of candor that can allow them to grow beyond the first idea.”

 

“The Future Arrived Yesterday” by Michael S. Malone

Nilofer Merchant: “The next type of company is going to have to grow in a very different way than companies even in the last 10 years. Mike Malone who wrote about virtual corporations 25 years ago has now written about “the protean corporation” which is a way to say organizations will organize to be more fluid, nimble, and shape shifters. He’s onto the new model and entrepreneurs should know about it so they are not surprised by the growth stages needed. ”

 

“Switch: How to Change Things When Change Is Hard” by Chip Heath and Dan Heath

Sean Ellis: “[The book’s] key message is to double down on things that are working.”

 

“The Entrepreneur’s Guide to Business Law” by Constance Bagley and Craig Dauchy

Chris Dixon: “[This one might be a] bit painful if you aren’t into legal details (I’m not), but perhaps the most useful business book you can ever read.”

 

“Crossing the Chasm” by Geoffrey A. Moore

Chris Dixon: “Although a bit too enterprise- (vs. consumer-) focused for my taste, this is an extremely intelligent and useful book.You’ve probably heard about the central thesis (lots of startups get stuck in the “chasm”, in between early adopter and mainstream customers) but there are tons of other interesting anecdotes and ideas in the book. I’ve reread this one a couple of times.”

 

“Boyd: The Fighter Pilot Who Changed the Art of War” by Robert Coram

Steve Blank: “Observe, Orient, Decide and Act – The cornerstone of Customer Development and the Lean Startup was first invented by a fighter pilot.  Read his story.”

Steve is a former serial entrepreneur who now teaches at U.C. Berkeley, Stanford University and the Columbia University/Berkeley Joint Executive MBA program. He is the author of Four Steps to the Epiphany.

 

“The Innovator’s Dilemma” and “The Innovator’s Solution” by Clayton Christensen

Steve Blank: “Why do large companies seem and act like dinosaurs? Christensen finally was able to diagnose why and propose solutions. Entrepreneurs should read these books as ‘how to books’ to beat large companies in their own markets.”

Also recommended by Chris Dixon: “The Innovator’s Dilemma popularized the (often misused) phrase ‘disruptive technology’; But there’s a lot more than that one big idea. Great insights into the ‘dynamics’ (changes over time) of markets.”

 

“Influence: The Psychology of Persuasion” by Robert B. Cialdini

David Heinemeier Hansson: “Influence teaches you how to sell and deal with customers by treating them as humans. Great stuff.”

David is a partner in 37signals.

 

“Maverick!: The Success Story Behind the World’s Most Unusual Workplace” by Ricardo Semler

David Heinemeier Hansson: “Maverick tells the story about how you can make radical change [even at] a very old-world company of 8,000 people producing industrial pumps.”

 

“Blink” by Malcolm Gladwell

Paul Jozefak: “Some great advice on how decisions are made.”

Paul is a Managing Partner at Neuhaus Partners.

 

“Lucky or Smart? Secrets to an Entrepreneurial Life”, by Bo Peabody

Mark Peter Davis: “Insight into some of the unique trials entrepreneurs face.”

Mark is a co-founder are CEO of Kohort, who previously worked as a VC at DFJ Gotham Ventures.

 

“The Zen & Art Of Motorcycle Maintenance”, by Robert M Persig

Brad Feld: “Anyone who is creating anything should read this book, slowly, and savor it.”

Brad Feld has been an early stage investor and entrepreneur for over 20 years and is the co-founder of Foundry Group.

Also recommended by Fred Wilson: “There is way more insight to be gained from stories than from business books. And these are some amazing stories.”

 

“The Thank You Economy”, by Gary Vaynerchuk

The Thank You Economy is much more than saying “thank you.” The Thank You Economy represents a much bigger movement. This book could easily have been called The Humanization of Business or Manners Marketing.

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In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”

While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.

Why This Gap Exists

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What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.

Tools and Techniques to Bridge the Gap

Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.

1. Practice Mutual Empathy

Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.

2. Maintain Professional Boundaries

Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.

3. Follow the Golden Rule

Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.

4. Avoid Micromanagement

Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.

5. Empower Employees to Grow

Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.

6. Communicate in All Directions

Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.

7. Overcome Insecurities

Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.

8. Invest in Coaching and Mentorship

True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.

9. Eliminate Favoritism

Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.

10. Recognize Efforts Promptly

Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.

11. Conduct Thoughtful Exit Interviews

When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.

12. Provide Leadership Development

Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.

13. Adopt Soft Leadership Principles

Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.

The Bigger Picture: HR’s Role

Mercer’s global research highlights five key priorities for organizations:

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  • Embrace flexible work models

  • Design compelling career paths

  • Simplify HR processes

  • Redefine the value HR brings

The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.

Treat Employees Like Associates, Not Just Staff

When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.

Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.

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