5 Books to Reread with Experience
“Not all readers are leaders, but all leaders are readers.” - Harry S Truman.
A healthy consumption of reading is one of the few habits that every successful person, from athletes, to artists, to scientists and entrepreneurs swear by. When it comes to entrepreneurship and leadership, there are a number of essential reads. All of these books are featured on bestseller lists and are critically acclaimed so you likely have heard of them already. But I want to look at these works from a different perspective. What key concepts or stories maintain relevance over time?
Have you ever listened to a song that you loved from your youth and discovered a whole new meaning to the lyrics? The words haven’t changed, and you have listened to this exact song many, many times over. Have you noticed that at different points in your life the words can take on new meaning? Most songs are some allegory for being in love, relationships or falling out of love. As a young person these messages may have seemed aspirational and much more theoretical. But as time goes on and you progress through life, you gain experience. And with that experience you gain perspectives and deeper insights unique to you.
The same goes for great business books. They take on a deeper meaning over time and you can develop deeper insights through relevance. The five books featured here are five of my personal all-time favorite business books and all contain high impact applications for entrepreneurship.
True North, Bill George (with Peter Sims)
Tearing Down the Walls, Monica Langley
The Hard Thing About Hard Things, Ben Horowitz
The Power of Habit, Charles Duhigg
It turns out that the other phrase we have all heard, “experience matters,” is true and these particular reads have proven to take on more depth as you build real world reference points throughout your career. If you have not read these yet, it’s never too late to start, and if you have, I am confident that you will see how the concepts, advice and learnings from each book will be reinforced when you revisit them again through an experienced lens.
Good to Great, Jim Collins
There is not much I can say about this book that hasn’t already been said. It is hands down one of the all time best business books, which is validated in its 4+ million sold bestseller status.
Business and Entrepreneurship is so diverse and broad making it difficult to dive deeper than the accepted headlines that things like passion and hard work make the difference. What I find so special about Mr. Collins’s work is the discipline and depth of research behind the book. It is his team's synthesis of the research data that leads to so many useful frameworks, making it a timeless masterpiece.
The concept that continues to resonate over time with my business, and the companies we invest in, is The Flywheel Effect. To learn more about Mr. Collins’s Flywheel Concept, click here.
I tried for years to adapt a Flywheel to my business pursuits and it never seemed to work in the way I intended. Which revealed my approach to the work I was doing, at that particular point in time, wasn’t working either.
For me, there has proven to be no better litmus test to determine if your business can scale than the Flywheel. It can take years to perfect (as was my case) but when you do it's a deceptively simple model to help guide your company's actions against a broader plan.
The Flywheel doesn't care what you do, it doesn’t care about your ideas. It's a system that works if your systems work. Businesses are, in part, a collection of systems and this took me years to understand.
The genius in Good to Great is an ability to synthesize the characteristics of greatness and provide models. I would assert that if you can’t build a Flywheel around your business, then you should rethink your business plan. I know I did.
True North, Bill George with Peter Sims
I first read this during my MBA program at Fordham University in NYC. It had an immediate impact on me. The clarity and breadth of real world experiences as told by 125+ top leaders helped form the aperture through which I would start to view my aspirations to be a future leader.
Bill George was the Chairman and CEO of Medtronic and Professor of Management at Harvard. I’m sure he could have written a whole book on his experiences alone, but clearly Mr. George is a student of business leadership. He and his co-author Peter Sims had access to these leaders of industry and it's beyond me how they came to convey so much great advice in a mere 201 pages.
What stands out to me as I recently revisited this book, is how prescient the concepts of “Leadership as a Journey” have proven to be. Messrs. George and Sims map out the Journey to Authentic Leadership in one simple chart (“The Journey to Authentic Leadership”) and overlay this journey with age and experience. When I first read this book, I was taking the first steps towards my career and it was difficult to imagine how far away the ages of 40, 50 and 60 seemed. Now I’m nearing the midpoint and the path their phased leadership journey chart laid out has proven to be perfectly accurate. Everyone in their mid 40’s should take a moment to compare their path to the map they provide.
The concept of Journey has become a constant theme throughout my career when these professional and personal crucibles have metastasize. I have learnt in my journey that the point isn’t to focus on the destination, but to travel your journey to the best of your potential. There is a map to help guide you, that with hindsight, could not be more useful in preparing for the road ahead.
True North introduces the concept of leaders going through a “Crucible.” The lowest point of the provided chart is the point between 40 and 50, the “Leading Phase” of a journey. This is when individuals tend to encounter a crucible (or in my case, many crucibles). As Mr. George highlights, this is a period that tests to the core, and transforms the understanding of what leadership is about.
Source: Bill George, HBS
This is a great example of the types of experiences that cannot be taught or simulated in a University setting. Mr. George states that the crucible is generally followed by a rapid acceleration of a leader's development. In my case, that was not only true, but something I now look for when investing in other entrepreneurs. Have they had to manage through their crucible? And most importantly, did they get to the other side? Heavy stuff...
Tearing Down the Walls, Monica Langley
I am a sucker for a story that starts with someone fighting their way to the top against the establishment. We hear the names CitiGroup, American Express and JP Morgan Chase and we think of ironclad financial institutions, but none of their stories would be complete without understanding the impact of Sandy Weill. Ms. Langley captured the incredible true story of a Polish Jewish immigrant of little means who goes on to become the engineer and mastermind behind billions of dollars in transactions and shareholder value. And if that isn’t interesting enough, he almost lost it all.
For anyone in finance, the impact of Sandy Weill’s ascension from humble, back-office beginnings to one of the titans of business, cannot be overstated. But I also find one of the most compelling aspects of his story, revisited with experience, is the focus on people and teams. It's not just about the leaders, but also their supporting cast. Were it not for Sandy Weill, would Jamie Dimon have become the titan of global finance he is today?
We can lose sight of the supporting cast at times, but as this next book points out, it's very much about your team and the people you surround yourself with.
The Hard Thing About Hard Things, Ben Horowitz
Andreessen Horowitz, one of the most recognizable names in venture capital. A16Z (as the firm is known) is relatively young in comparison to the large VC firms, especially in the context of the lifecycle of Silicon Valley. The firm was founded by people who actually have experience starting, building and running companies. And believe it or not, this was an innovative model at the time.
Mr. Horowitz’s story is part hero leader who built great teams and companies, part relentless entrepreneur with an inability to give up, and part case study in the importance of operational acumen and capability. Running successful businesses is hard and I always think about this book when someone uses a phrase I love, “perspiration over inspiration.” No lesson has proven to be more true.
What is also interesting about this book, which became apparent through multiple readings, is how transparent Mr. Horowitz is about his own struggles with uncertainty and self doubt. The journey to build a company can take a toll, of which I was wholly unprepared for at the start of my career. Mr. Horowitz shares a lot of insight in how he handled seemingly impossible situations not just with his employees and investors, but his family and friends. The lonely endeavor of entrepreneurship seems a little less so thanks to radical honesty in The Hard Thing About Hard Things.
The Power of Habit, Charles Duhigg
I discovered Charles Duhigg’s The Power of Habit at a time when I was searching for answers to a lot of personal questions. It's an illuminating read that explains human behavior through simple visual models that make the concepts incredibly accessible. Everyone aspiring to lead companies and teams should have an understanding of how human nature shapes our actions and decisions.
This book also features a business case study that has had a profound resonance over the years. The story of Paul O'Neill taking the reins of Alcoa in 1987 has become the stuff of legend. In his first presentation as the new CEO he shared that the company's singular focus was going to be on worker safety. “Every year, numerous Alcoa workers are injured so badly that they miss a day of work,” he stated. “I intend to make Alcoa the safest company in America. I intend to go for zero injuries.”
When he was asked about inventories and capital ratios - the standard vocabulary for these kinds of presentations - O’Neill returned to the same theme.
“I’m not certain you heard me,” said the new CEO. “If you want to understand how Alcoa is doing, you need to look at our workplace safety figures. If we bring our injury rates down, it won’t be because of cheerleading or the nonsense you sometimes hear from other CEOs. It will be because the individuals at this company have agreed to become part of something important: They’ve devoted themselves to creating a habit of excellence. Safety will be an indicator that we’re making progress in changing our habits across the entire institution. That’s how we should be judged.“
The Wall Street analysts literally called him crazy, but his focus on the mission of worker safety resulted in him building $27 billion dollars of shareholder value during his tenure. It’s a lesson I think about often. If you have a central “Keystone Habit” that guides all facets of your business’s activities, then avoid taking outside criticism to heart.
Conclusion
These are five of the very best books I have read and stand out as books to re-read over the course of your career. They all share an element of universal truths about business, with specific anecdotes and applications that I have found become even more layered and useful the second and third time through.
I hope you find them as indispensable as I do and wish you the best of luck on your business and leadership journey.