100 Books Like Disciplined Entrepreneurship

I’ve spent my career building products, scaling companies, and leading teams through the highs and lows of entrepreneurship. I know firsthand how challenging it is to take an idea and turn it into something real—whether that’s a product, a company, or a movement. The books on this list have shaped my approach to leadership, innovation, and resilience. They’ve helped me navigate tough decisions, build stronger teams, and think bigger. I’m passionate about sharing these insights because I believe great builders aren’t just born—they’re made. If you’re looking to create something meaningful, these books will push you, challenge you, and inspire you to build something great.

I’m a 3-time B2B startup founder (Flagback, HireVoice, and Highlights). For my 2nd startup, HireVoice, we tried to use The Lean Startup methodology and struggled to get traction on the market. When we shut down the company, I knew I wanted to solve my own pain, and learn B2B. I spent the next 2 years speaking (and learning from) some of the most successful B2B founders in the world. This, eventually led to the publication of my book, Lean B2B. Since then, I’ve been at the forefront of B2B entrepreneurship. The Lean B2B methodology has now been used by thousands of entrepreneurs and innovators to help create successful businesses.

I’m a 3-time B2B startup founder (Flagback, HireVoice, and Highlights). For my 2nd startup, HireVoice, we tried to use The Lean Startup methodology and struggled to get traction on the market. When we shut down the company, I knew I wanted to solve my own pain, and learn B2B. I spent the next 2 years speaking (and learning from) some of the most successful B2B founders in the world. This, eventually led to the publication of my book, Lean B2B. Since then, I’ve been at the forefront of B2B entrepreneurship. The Lean B2B methodology has now been used by thousands of entrepreneurs and innovators to help create successful businesses.

Ever since I was a kid, I’ve always been intrigued by how people make decisions and why the words we use can significantly impact those decisions. After years of conducting customer research and writing marketing messages for clients, my interest in finding and delivering compelling messages at just the right time to the right audience has only grown. I’ve poured my experience in the online marketing trenches into my book, Finding the Right Message, where I reference more than one of the authors on my recommendation list. 

I’m a serial entrepreneur who’s built and sold several startups. I’ve been helping non-venture-backed startup founders since 2005 and now I run the first startup accelerator for bootstrappers, called TinySeed. I’ve invested in 57 startups, but I don’t believe the only way to start a SaaS company is to raise money. I host the most popular podcast for bootstrappers, called Startups for the Rest of Us. I also run the most well-known conference and online community for non-venture-track SaaS founders, called MicroConf.

We are scholars and writers, coaches and company builders, optimists, and (on our best days) accelerators of action. It’s been the privilege of our lives to work as change agents at some of the world’s most influential companies—and with some of the world’s most inspiring business leaders. But at the core of our identities, we are educators, which is why we write books about leadership. We believe that what we’ve learned in the process of changing things can be useful to anyone who seeks to lead, particularly now, when the scale and complexity of our shared challenges can seem overwhelming. 

I’m Heather Smith and I love writing. I love Accounting and AccounTech. I gratefully sit at the Ikigai inflection point, where my profession, passion, vocation, and mission intersect, and I can use my explanation skills to empower others in the accounting industry. Ikigai is a Japanese concept referring to something that gives a person a sense of purpose, a reason for living. Believing Accountants don't save lives, Accountants save livelihoods; I use my superpower of explanation to educate the accounting profession about accounting technology and modern accounting practices. I do this through many channels including my latest book Xero for Dummies, 5th edition. 

I have worked with startups since 2000, when I joined ShareBuilder, ultimately sold to Capital One in a $9.5 billion deal – one of my five successful startup exits to date. I am currently an officer of seven startups. Startups drive global job creation and problem-solving innovation. But 90% fail, often for preventable reasons. I am helping entrepreneurs beat those odds. I wrote Startup Law and Fundraising to help entrepreneurs build on a solid foundation, avoid common legal and regulatory mistakes, and fund their vision. My books are used globally in law and MBA schools, and I speak constantly on entrepreneurship-related topics, including recently to groups in Istanbul, Ramallah, and Tehran. 

I learned about leadership and building organizations in a volunteer, community-based organization growing up. I ran my first leadership workshop as an 18-year-old for 15-16-year-old kids, and at its peak, led a passionate group of 200+ kids. I then woke up from that dream into a “real job” as a product manager in a company selling products like bath soap and shampoo, and later as a strategy consultant. It was there that I noticed the significant pain people were experiencing in the corporate world, and I realized I could help leaders build organizations where both the business and its people could thrive. 

I’ve spent my career building products, scaling companies, and leading teams through the highs and lows of entrepreneurship. I know firsthand how challenging it is to take an idea and turn it into something real—whether that’s a product, a company, or a movement. The books on this list have shaped my approach to leadership, innovation, and resilience. They’ve helped me navigate tough decisions, build stronger teams, and think bigger. I’m passionate about sharing these insights because I believe great builders aren’t just born—they’re made. If you’re looking to create something meaningful, these books will push you, challenge you, and inspire you to build something great.