The Reading List That Changed How I Think as a Founder

20 Books That Shaped How I Lead, Decide, and Operate

I’ve spent most of my career inside real businesses, leading teams, selling, building systems, and making decisions when the margin for error is small. These books weren’t consumed for inspiration. They were used. Some gave language to instincts I already had. Others exposed habits that were quietly limiting me. A few changed how I think entirely. Together, they form the backbone of how I operate today.

How to Win Friends and Influence People by Dale Carnegie. I first read this in a professional sales class in college, and it changed the direction of my career. It was the first book that showed me success is shaped by human behavior, not credentials. Until then, effort and intelligence felt sufficient. They aren’t. Deals stall, teams resist, and relationships strain when people feel dismissed. Learning to slow conversations down and lead with curiosity has shaped how I sell, how I lead, and how I communicate to this day.

Principles by Ray Dalio. This book reinforced that clarity is built, not assumed. Decisions improved once I stopped relying on instinct alone and started evaluating outcomes against principles. When something went wrong, the focus shifted from blame to structure. That change reduced emotion and increased consistency. Over time, this approach shaped how I plan my weeks, review priorities, and separate signal from noise. Structure created stability rather than limitation.

Thinking, Fast and Slow by Daniel Kahneman. This book exposed how often confidence is mistaken for accuracy. It forced me to slow down decisions that felt obvious and question assumptions that felt earned. The biggest impact showed up in hiring, forecasting, and strategic planning. Judgment improved once certainty softened and dissent became welcome.

Multipliers by Liz Wiseman. This book revealed my biggest leadership blind spot. I was a do-it-for-you manager. I framed it as efficiency and high standards, but in reality it limited growth and ownership. By stepping in too quickly, I prevented others from thinking and leading. Once I changed that pattern, teams became stronger and accountability improved. Scale followed shortly after.

Never Split the Difference by Chris Voss. Voss reframed negotiation as emotional awareness rather than leverage. Conversations became more effective once I stopped pushing for agreement and started slowing things down. Acknowledging emotions reduced resistance. Asking better questions produced better outcomes. This approach improved negotiations and leadership conversations alike.

The Challenger Sale by Matthew Dixon and Brent Adamson. Mark had always led with a challenger mindset before there was language for it. He pushed clients to think differently and refused to sell comfort. This book clarified why that approach worked and how to apply it intentionally. It gave structure to instinct and helped shape how we think about leadership, sales, and growth. That clarity directly influenced what became IGTMS.

Antifragile by Nassim Nicholas Taleb. Taleb changed how I think about stress and uncertainty. Instead of trying to eliminate volatility, I began designing systems that could absorb it. Over time, that mindset reduced reactivity and improved decision-making under pressure. Strength became less about control and more about adaptability. That shift shows up everywhere from leadership to long-term planning.

Man’s Search for Meaning by Viktor Frankl. Frankl reframed responsibility as choice. During difficult seasons, that perspective brought steadiness rather than motivation. During successful ones, it kept ambition grounded. Meaning proved more durable than momentum and continues to influence how I think about leadership and resilience.

The Boron Letters by Gary Halbert. This book is a compilation of letters written by Gary Halbert to his son while he was in prison. That context matters. Halbert was deeply flawed, wildly unconventional, and undeniably brilliant. The letters move between copywriting, human psychology, discipline, and life advice with startling clarity. Reading them feels like watching raw intelligence at work. There is a sharpness to the thinking that reminds me of Leonardo DiCaprio’s character in Catch Me If You Can. Unpolished, fast, and dangerous in the best way. The lessons are simple and timeless. Attention matters. Clarity matters. Incentives drive behavior. Human behavior has not changed, and Halbert understood that better than most.

$100M Offers by Alex Hormozi. Hormozi sharpened how I diagnose problems. Instead of blaming effort or traffic, the focus moved to value and friction. Weak offers became obvious. When value was clear and risk was addressed directly, pressure came off the entire system. Execution improved because selling became simpler.

Good to Great by Jim Collins. Collins reinforced the power of discipline over intensity. Sustainable growth came from the right people, clear standards, and consistent execution. Progress slowed in the best way. Long-term wins became quieter and more durable.

The Effective Executive by Peter Drucker. Drucker changed how I treat time. Activity stopped being confused with contribution. Focus shifted toward decisions and work that actually moved outcomes. Effectiveness became intentional rather than accidental.

Influence by Robert Cialdini. Cialdini provided a framework for understanding persuasion. Patterns became visible in pricing, negotiation, marketing, and culture. Awareness changed how influence was used and how manipulation was avoided. Nothing disappeared. It became conscious.

The Hard Thing About Hard Things by Ben Horowitz. Horowitz captured leadership without polish. There are moments when frameworks fail and responsibility is heavy. This book did not promise solutions. It prepared me to carry decisions when no option felt clean.

Deep Work by Cal Newport. Newport reinforced the importance of protecting attention. Focus improved once boundaries were enforced and availability stopped being rewarded. Better thinking followed. This book influenced how I structure my time and guard against distraction.

Outliers by Malcolm Gladwell. Gladwell softened how I judge performance. Success became easier to understand once context, timing, and repetition were considered. Leadership improved when environments were designed intentionally rather than relying on individual brilliance.

Revenge of the Tipping Point by Malcolm Gladwell. This book updated how I think about influence in a modern context. Systems, incentives, and algorithms now shape momentum. Old playbooks stopped applying. Strategy improved once reality replaced nostalgia.

Talking to Strangers by Malcolm Gladwell. Assumptions slowed. Questions increased. First impressions lost authority. Hiring and partnerships improved once certainty gave way to curiosity. The cost of misjudgment became clearer at scale.

Atomic Habits by James Clear. Clear showed how systems outperform motivation. Discipline became structural rather than emotional. Small, repeatable behaviors created durable progress. Culture revealed itself through action rather than intention.

The Go-Giver by Bob Burg and John David Mann. The simplicity of this book is what makes it powerful. Value creation, trust, and generosity are framed as strategic rather than sentimental. I leave this book in the nightstands of my investment properties for tenants. That choice reflects how I want to operate. Long-term wins are built on relationships, not transactions.

I don’t recommend these books lightly. They earned their place through application, not theory. Some will feel heavy if you are early in your career. Others will feel familiar if you are already carrying responsibility. That’s the point. The right book meets you where you are and pushes you slightly further. Together, these form the operating system I continue to refine as the stakes get higher.