Four Books Every Entrepreneurial Leader Should Read

By Carolyn Lagermasini, CAE

At the heart of every great association is a mission. But turning that mission into a thriving, sustainable organization requires more than just passion—it requires an entrepreneurial mindset.

As the founder and sole owner of Association & Conference Group, I know firsthand the challenges and rewards of growing a business. Furthermore, I’ve seen firsthand how entrepreneurial principles can transform a non-profit. I have come to rely on a handful of leadership books as my go-to resources for navigating this business journey. They’ve provided frameworks for building a strong company culture, staying focused on our mission, and achieving sustainable growth. Here are the four books that I believe are essential for any entrepreneur.

Start with Why by Simon Sinek

Sinek’s book is foundational for any entrepreneur. It’s not about what you do or how you do it, but why you do it. For me, the “why” behind ACG is to empower people. When you can articulate your core purpose, you can inspire your team, attract the right clients, and build a business that stands for something more than just profit. This book challenged me to define my company’s core purpose and use it as a compass for every decision.

Dare to Lead by Brené Brown

In the fast-paced world of entrepreneurship, it’s easy to believe you have to have all the answers. Brené Brown’s Dare to Lead teaches that true leadership is rooted in courage and vulnerability. It’s about creating a work environment where my team feels safe to take risks, share ideas, and admit mistakes without fear of judgment. This book helped me understand that showing empathy and having difficult conversations with honesty and respect strengthens our team and builds a more resilient company culture.

Good to Great by Jim Collins

As a small business owner, the goal is always to move beyond “good” and aim for “great.” Collins’ research-backed insights in Good to Great were a game-changer. The concept of Level 5 Leadership—a leader who is humble yet fiercely determined—really resonated with me. The Hedgehog Concept, which focuses on what your company is passionate about, what it can be the best at, and what drives its economic engine, provided a simple but powerful filter for our business strategy. It helped me narrow our focus and stop chasing every opportunity, allowing us to excel in our niche.

Traction by Gino Wickman

For an entrepreneur juggling everything from sales to strategy, a clear operational system is non-negotiable. Traction introduced me to the Entrepreneurial Operating System (EOS), a practical framework for running my business. This book provided tools to clarify our vision, get the right people in the right roles, and create a disciplined approach to execution. It’s the playbook that helps me move from being a leader with great ideas to a leader who gets great results. It’s the system that keeps the wheels of ACG turning smoothly.

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