9 books every small business owner should read

I didn’t learn how to be an entrepreneur in school—I have my JD, not my MBA. That meant I had to play catch-up as I made the transition from being an attorney to being the owner and leader of Pines Federal. The most helpful resources for me were books written by successful entrepreneurs and business leaders.

I’ve read more books about business than I can count. Some are trash, some are gold. Here, I’ve curated a few of my favorites—the ones that were and continue to be the most helpful throughout my learning experience. I know everyone’s journey is different, but I hope you’re able to take as much from these small business books as I did.

1. Rich Dad, Poor Dad

In Rich Dad Poor Dad, Robert Kiyosaki compares his working-class father to his childhood friend’s rich parents to illustrate how investing and calculated risk-taking, among other things, allow the rich to stay rich. But the book also passes on valuable lessons about business and leadership. One particular quote from Kiyosaki continues to influence the decisions I make every day regarding my business:

When I first branched out on my own and opened my law firm, I quickly discovered that law school didn’t prepare me at all for the challenges I would need to overcome as a business owner and leader. Although some early mistakes cost me time and money, they also yielded practical lessons: namely, the importance of having thick skin.

2. Strategize to Win

Carla Harris’s Strategize to Win speaks to anyone who’s contemplating a career change, which makes it invaluable for new entrepreneurs. She shows you how to attract the kinds of opportunities you want, first by clearly defining your goals and what you have to offer, then by building relationships and making changes as necessary. 

Harris offers practical advice and examples for everything from resilience to navigating interpersonal conflict. Here’s one quote that stood out to me:

“Having as many conversations as possible with as many people as you can about your career aspirations will help you expand your ideas and bring to light options you may never have considered.”

I lived overseas for three years in Jerusalem and studied Talmudic law at Machon Shlomo. My time in Jerusalem was spent immersing myself in the culture and getting to know people in the local community. Through countless conversations with strangers and mentors I met in Jerusalem, I discovered so many opportunities I’d never even dreamed of.

3. Start With Why

Good leadership isn’t about telling people what to do; it’s about motivating people so that they want to do it. That’s the idea at the center of Simon Sinek’s book, Start With Why.

“We are drawn to leaders and organizations that are good at communicating what they believe. Their ability to make us feel like we belong, to make us feel special, safe and not alone is part of what gives them the ability to inspire us.”

I’ve never read a book that expresses this theory more eloquently than Start With Why. Whether it’s narrowing down your ideal client or articulating your business strategy to your employees, the ways in which you communicate as a leader will send powerful signals to those around you and substantially impact whether your words are inspiring—or ignored. 

4. Dare to Lead

Dare to Lead by Brene Brown is about creating a positive work culture. And that’s why, as Brown argues, leaders need to allow themselves to be vulnerable and emotionally honest in tough situations. 

“The courage to be vulnerable is not about winning or losing, it’s about the courage to show up when you can’t predict or control the outcome.”

By modeling this, business leaders create an environment where failure is ok, where trying new things is encouraged, and where people are heard. Brown’s words have inspired me to create a work culture that accepts and promotes vulnerability, and I’ve found that, as Brown indicates, it absolutely facilitates innovation and creativity among the people I lead.

5. The Work

In The Work, Wes Moore draws on his life story and his interactions with people from all walks of life to answer the question: what makes work meaningful? As an entrepreneur, finding meaning in your work isn’t just a nice-to-have—it’s a necessity. 

“How we spend our days is how we spend our lives, and it’s the rare person who can walk away from what feels like a sure thing.”

Before I went off on my own to start a law firm, I worked as in-house counsel for a social security labor union. The job provided me with a fair salary and career stability, but when my wife wanted to move to Houston to be near her family, I knew it was an opportunity to have a job that made me feel a greater sense of purpose. 

It was difficult to leave a secure position—especially with five young children at home—but it was the best decision for my family. Not only were we able to be closer to family, but I was able to do something that I felt more connected to, which made me more whole as a professional and as a partner and father.

6. Essentialism

There are lots of ways to make more money, but time is a non-renewable resource. As an entrepreneur, you need to protect your time, treating every waking hour like it’s costing you money.

Essentialism by Greg McKeown is about saving your energy for the things that really matter, being intentional with how you spend your time in a world where we’re bombarded by distractions. 

“The faster and busier things get, the more we need to build thinking time into our schedule. And the noisier things get, the more we need to build quiet reflection spaces in which we can truly focus.”

Essentialism taught me how to take control of my professional life and to live with purpose and intention. I still succumb to those distractions, yes, but they don’t dominate my work life, and I’ve built time into my days to think.

For example, I now go for a bike ride once a week for an hour, listening to Audible business and self-growth books. I also pray every morning for 45 minutes, and after my prayer, I take time to think about the day ahead. And I observe the Jewish Sabbath, which means I don’t use smartphones or any electronic media from Friday at sundown until Saturday at sundown. The complete detachment from my work at that time recharges me and makes sure I’m connecting with my family and myself. 

7. Mindset

Often what holds us back—in life and at work—are our own limiting self-beliefs. Carol Dweck’s Mindset examines the human capacity for growth. It asserts that assuming that your level of talent and intelligence is static limits your potential. Instead, adopting what Dweck calls a “growth mindset”—the understanding that your skills and knowledge are fluid and can be grown over time—unlocks new possibilities.

“The passion for stretching yourself and sticking to it, even (or especially) when it’s not going well, is the hallmark of the growth mindset. This is the mindset that allows people to thrive during some of the most challenging times in their lives.”

After reading this book, I tried to stop telling myself I wasn’t good at one or another thing and change my mindset to believe that I could get better at something. And it’s not just about working on my weaknesses: working on my strengths—knowing there’s always room for growth—is just as important. 

This extends into my personal life too. I’ve played guitar my whole life, but I never really improved my abilities as a musician. After reading Mindset, I was inspired to take up classical guitar and learn how to read music. I’ve grown leaps and bounds, and it was a reminder that what makes people great at what they do is mostly hard work and not innate talent.

8. Give and Take

You can’t pull yourself up by your bootstraps. Successful entrepreneurs, especially, have an entire network of mentors, clients, investors, and friends who support them on their journey. It’s impossible to repay all of that support and generosity directly, but you can pay it forward: help others achieve their goals as your support system has done for you.

In Give and Take, Adam Grant argues that giving to others isn’t just the right thing to do—it also lays the foundations for your own success. 

“The more I help out, the more successful I become. But I measure success in what it has done for the people around me. That is the real accolade.”

That sentiment has shaped the type of leader I am today. Our law firm focuses on facilitating our employees’ career development. We encourage them to grow with the firm, and we always try to find a place for them when they do. In fact, three of our intake specialists became paralegals and now assist with some of our firm’s biggest cases and high-value clients. 

9. I Got There

J.T. McCormick’s life story, I Got There, is about overcoming adversity—and how. The author started with nothing, grew up in some of the most difficult circumstances imaginable, hit rock bottom more than once, and rose above it all to become a successful CEO.

McCormick’s story is inspiring, but it also provides readers with plenty of useful advice for leading a team:

“Everything in business comes down to focusing on people—your customers, your partners, and most importantly, your team. When you care about the people you’re serving, then results are easy.” 

At my firm, we take on as many cases as we can for folks who can’t afford our services. Of course, we can’t offer pro bono work to everyone who needs it because we need to stay in business, but when we have the bandwidth, it’s incredibly energizing. Many of our clients are disabled veterans, people who have given their hearts, souls, and bodies for our country, so it’s a pleasure to be able to make a tangible, positive difference in their lives. 

We don’t focus on what’s best for us—we focus on what’s best for the people we represent. The beautiful thing is that, in the end, that’s what ends up being best for our firm as well: positive reviews, word-of-mouth referrals, and the energy that comes from using our knowledge and skills to help people.

Each of these books for small business owners has guided me in my transition from being an attorney to being a business owner. Knowledge is power when you’re an entrepreneur, and always striving to know more and learn from others will bring your business closer to success. It has for me.