20+ Books that Helped Entrepreneurs Overcome Major Business Challenges
Entrepreneurs spilled the book that has saved them during their toughest times.
Starting and growing a business can feel like an endless series of challenges, but sometimes, all it takes is the right book to shift your perspective and give you the tools you need to succeed.
We’ve rounded up some top book picks from seasoned experts who’ve been through the wringer and come out stronger.
These books have been their go-to guides for tackling everything from tough leadership decisions to bouncing back from setbacks.
Shoe Dog by Phil Knight
In 2017, I hit a point where my business wasn’t growing, and I considered calling it quits. I remember reading ‘Shoe Dog’ by Phil Knight on a rainy September evening, and one part really stuck with me.
Phil talking about how he almost lost Nike due to cash-flow problems in 1975. That moment, when he faced losing everything yet kept pushing, made me rethink my own struggles.
It was the push I needed to keep going, and within six months, I saw a turnaround in my business. His persistence became my turning point.
Bhavik Sarkhedi, Founder & Creative Director, Ohh My Brand
Principles by Ray Dalio
When we were entering a new market, ‘Principles’ by Ray Dalio proved invaluable.
Dalio’s advice on embracing the harsh truths of reality rather than clinging to optimism made all the difference. Objectively assessing the market allows me to adjust my strategy on the fly.
Amar Ghose, CEO, ZenMaid
Dare to Lead by Brené Brown
The most disheartening experience we witnessed in our firm was the loss of our biggest client.
The book ‘Dare to Lead’ by Brené Brown helped me learn about vulnerability.
I openly shared the loss with my team and created an environment where the team could air their grievances and express themselves.
These sincere and empathetic touchpoints with clients and our team cemented our internal relationships while also offering essential client feedback.
Aseem Jha, Founder, Legal Consulting Pro
Made to Stick by Chip Heath and Dan Heath
“Made to Stick” by Chip Heath and Dan Heath was a game-changer when we needed to communicate our company’s value proposition more effectively to our customers.
The book’s principles on crafting messages that are simple, unexpected, and memorable helped us refine our marketing strategy and make a stronger impact.
Deep Work by Cal Newport
“Deep Work” by Cal Newport helped me revolutionize my approach to productivity and focus in the ever-distracting world of digital marketing.
The concept of deep work allowed me to block out distractions and prioritize tasks that drive the most value, which significantly enhanced my ability to manage our projects and develop strategic campaigns.
Marc Bishop, Director, Wytlabs
🌼 LeadLearnLeap summarized the book in this 6-minute animated video 🌼
Good to Great by Jim Collins
“Good to Great” by Jim Collins completely shifted my perspective during a critical period of growth.
It helped me understand the value of focusing on what our agency could be best at and aligning our team with that goal.
The “Hedgehog Principle” concept allowed us to double down on our strengths, leading to more consistent and sustainable growth in a competitive market.
Sahil Kakkar, CEO & Founder, RankWatch
Blue Ocean Strategy by W. Chan Kim and Renée Mauborgne
“Blue Ocean Strategy” by W. Chan Kim and Renée Mauborgne helped me see the power of creating uncontested market space.
Instead of competing in a saturated eLearning landscape, we focused on innovative solutions, offering unique content and marketing strategies.
This shift allowed us to carve out our niche and lead the market, attracting a wider audience and establishing long-term growth.
Christopher Pappas, Founder, eLearning Industry Inc
The One Thing by Gary Keller and Jay Papasan
The One Thing by Gary Keller and Jay Papasan significantly impacted my approach to business.
The book highlights the value of focusing on a single priority, which helped me improve productivity and make better decisions.
Concentrating on essential tasks taught me to use my resources wisely and effectively address challenges.
Ketie Zhang, Founder, Ketie Story
Crossing the Chasm by Geoffrey Moore
The book’s insights into how to market and sell disruptive products to mainstream customers helped me identify the gaps in our approach to client acquisition.
We were stuck catering to early adopters but struggled to reach a broader audience.
By applying Moore’s strategies, we refined our messaging. We positioned our services more effectively, significantly expanding our client base and propelling our growth beyond the initial ‘chasm’ holding us back.
Marcus Clarke, Owner, Searchant
The Hard Thing About Hard Things by Ben Horowitz
Horowitz’s candid sharing of his experiences as a startup CEO provides not only practical strategies for managing difficult situations but also emotional support.
The book offers honest insights into the realities of running a business, from managing cash flow to handling internal conflicts — which helped me navigate my company through tough times with a clearer perspective and renewed determination.
David Wilfong, Founder and CEO, DavidWilfong
Start With Why by Simon Sinek
As the founder of a business that helps other businesses onboard global talent to expand into new marketplaces, the greatest challenge was always being able to foster a company vision that was unified across all the teams, globally.
The book that truly enabled me to know how to make our purpose match up with operations was ‘Start With Why’ by Simon Sinek.
Focusing on ‘why’ has enabled us to have a mission-driven culture that scales seamlessly across borders to drive our international success.
Lucas Botzen, Founder, Rivermate
🌼 For reference, here’s an animated summary of Find Your Why, another great book by Simon Sinek 🌼
Profit First by Mike Michalowicz
“Profit First” by Mike Michalowicz helped me overcome my roofing and construction company’s financial challenges.
It focuses on a simple cash-management system. I learned to prioritize profit, taxes, and owner’s pay while controlling expenses.
Tyler Poole, Owner, White Oaks Construction
The Goal by Eliyahu M. Goldratt
The Goal by Eliyahu M. Goldratt is an oldie but a goodie, and it helped me immensely.
You’d think a book about bottlenecks in manufacturing would have limited application, but you’d be wrong.
As a recruiter, it was fascinating to see that holdups on a factory floor had proxies in the hiring process.
Understanding why things turned stagnant helped me streamline sourcing and placement, decreasing time-to-hire for my clients.
Linn Atiyeh, CEO, Bemana
The Checklist Manifesto by Atul Gawande
When my business was plagued with operational inconsistency and expensive mistakes, I realized that our systems lacked rigor and accountability.
Following Gawande’s example, I wrote formal checklists to help colleagues with tasks that ranged from equipment pre-checks to customer interactions.
This simple technique dramatically reduced mistakes, boosted customer satisfaction, and made the operation run more smoothly, especially during peak times.
Sarah Gibson, Director, Proactive Healthcare
Essentialism: The Disciplined Pursuit of Less by Greg McKeown
After reading “Essentialism: The Disciplined Pursuit of Less” by Greg McKeown, I realized how much time I was spending on tasks that didn’t truly move the needle for our business.
I began focusing only on the most critical activities that aligned with my strategic goals.
Now, I consistently prioritize what matters most, and it’s made a tangible difference in both my focus and business outcomes.
Reyansh Mestry, Head of Marketing, TopSource Worldwide
The Art of War by Sun Tzu
It was ‘The Art of War’ by Sun Tzu. I learned that strategy isn’t always about just planning; it’s a gradual understanding of the terrain.
I mean not in the literal sense, but in knowing the emotional and psychological landscape of your team and competitors.
After reading the book, whenever I came across a major crisis, I stopped obsessing over spreadsheets or industry forecasts and instead focused on knowing my people and their motivations.
Yogesh Kumar, Digital Marketing Head, eResource Scheduler
The Innovator’s Dilemma by Clayton M. Christensen
Clayton M. Christensen’s ‘The Innovator’s Dilemma’ showed me the importance of building an innovative culture to tackle disruptive challenges in our business successfully.
I fostered this mindset by empowering my team with opportunities for experimentation and calculated risks, thereby enabling us to remain adaptable and responsive amidst industry disruptions.
Chris Aubeeluck, Head of Sales and Marketing, Osbornes Law
The Content Advantage by Colleen Jones
Being that we are in a specific niche industry, our business faced challenges in how to develop a social media strategy, and this is when I turned to Colleen Jones’s ‘The Content Advantage.’
What makes her book unique is that it approaches content development not only from a quality standpoint but also from a stage factor as well.
Jones’s actionable tips on how to efficiently develop quality content, as well as what types to post and when, helped me navigate social media and make it an advantageous part of our strategy.
Jessica Plaskoff, Director of Marketing, One Week Bath
Grit: The Power of Passion and Perseverance by Angela Duckworth
“Grit: The Power of Passion and Perseverance” by Angela Duckworth helped me realize that consistent effort is just as important as talent when it comes to achieving long-term success.
Fostering a culture where persistence is valued helps my team to stay focused on our goals, even when results aren’t immediate.
Albert Kim, VP of Talent, Checkr
Zero to One by Peter Thiel
The book’s focus on creating something unique rather than competing in crowded markets shifted my perspective during a critical phase when we were struggling to differentiate our software in a saturated market.
Thiel’s insights on building a monopoly through innovation encouraged us to stop imitating competitors and instead focus on solving a niche problem that no one else was addressing.
Joshua Webb, Head of Growth, Kinnovis
The Challenger Sale by Brent Adamson and Dixon Matthew
The book ‘The Challenger Sale’ was a real eye-opener for me during a tough period at Opnbx.
It completely shifted our sales approach from just relationship-building to challenging our customers’ thinking. Its focus on tailored insights and commercial teaching really resonated with our AI-driven approach to prospecting and lead generation.
We saw a 30% increase in conversion rates after implementing the book’s strategies. The book’s principles have now become a cornerstone of our SDR training program.
George Suarez, Founder & CEO, Opnbx.ai
The Five Dysfunctions of a Team by Patrick Lencioni
The book ‘The Five Dysfunctions of a Team’ by Patrick Lencioni was instrumental in overcoming a major challenge in my role.
It provided clear insights into improving team dynamics and leadership.
Implementing the strategies from this book helped resolve conflicts and foster a more cohesive and productive team environment.
Joshua Schirard, Director, Byrna
The E-Myth Revisited by Michael E. Gerber
The book shifted my mindset from working in my business to working on my business.
Early on, I was so caught up in daily operations that I lost sight of scaling and building systems.
Gerber’s approach taught me how to create a business that could run without being overly dependent on me, which was key to scaling my telecommunications company and taking on bigger ventures.
Ronald Osborne, Founder, Ronald Osborne Business Coach
This book opened my eyes to the importance of working on my business, not just on it.
I realized I needed to step back from the daily grind and focus more on creating systems and processes that would allow my business to grow and run smoothly without me being involved in every detail.
Hyacinth Tucker, Owner and CEO, The Laundry Basket LLC
🌼 🌼 More game-changing books recommended by experts 🌼 🌼
