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Tuesday, January 20, 2026

The Caterpillar’s Edge: Evolve, Evolve Again, and Thrive in Business. Sid Mohasseb (Rugged Land, 2017): Book Summary and Review


        This was an interesting book, sometimes fun. It is focused on strategy in a business world prone to disruptions and changing conditions. Though perhaps slightly dated now, eight years after it was published, it was certainly cutting-edge then in 2017. Author Sid Mohasseb is an entrepreneur, venture capitalist, investor, and business thought leader. I bought the nice hardback version from the Dollar Tree for $1 around 2018 or 2019. This book is amply peppered with quotes from business, thought, political, military, and other leaders and successful people.

               Part One is entitled Hopes and Fears: Past and Future. The first chapter examines addiction to outmoded ways of seeing and acting. He gives the sobering data that the vast majority of startups don’t find the capital they seek and end up failing. He also notes that companies and CEO tenures don’t last as long as they used to. He gives three reasons for this: 1) more diverse environments which are less predictable, 2) the pace and impact of change have increased due to technological innovation, and 3) better interconnectivity among businesses has great advantages but also risks. These factors should not be ignored. Mohasseb recounts his own experiences and some successes and failures of heading or ignoring these factors.

     Being flexible and accommodating disruption is one of the lessons of the book. Being resistant to change can be hazardous. Resisting change is reinforced by confirmation bias and overconfidence bias. Status quo bias, group thinking bias, and “now” bias may be other factors.

The age-old recipe for success was to gather data, analyze it, hypothesize around insights, choose the best plan, then execute that plan for the ensuing years. Today, this simply will not work. Why? Because set plans are by definition static, and the world in which we live and compete is dynamic, changing constantly. New technology allows for data points to come in from everywhere, all the time.”

     Fixed plans are simply not adaptive enough for dynamic markets and situations, he argues. He talks often about moments of insight he calls “Aha” moments and how certain ways of thinking can foster them.

     He cautions against corporate overconfidence. He emphasizes constant evolving and gives a three-fold formula for evolving: 1) align with uncertainty, 2) appreciate reality, and 3) aspire for more.

     The ability to deal with disruptions is very important, especially at a time when business and digital disruptors were popping up all over.

     Part Two is entitled Not Too Fast: Let’s Get Grounded. He recounts a bit of the history of the study of business strategy, arising from the Stanford Research Institute in the early 1960s, which defined business strategy simply as “a systematic means by which a company can become what it wants to be.” Business strategy was often modeled on military strategy. He mentions the influence of former GE CEO Jack Welch in the 1990s and Harvard Business School’s Michael Porter, who advocated for “competitive advantage.”

     Mohasseb does not mention AI but talks a lot about some of its precursors, like data analytics, digitization, the internet of things (IoT), and Big Data. These things enable faster and better business decisions and lead to insight. These things also lead to bigger and more data, which set the stage for the AI innovations we are seeing today. He does note that the Internet of Things (IoT) would generate massive amounts of new data, which it has and continues to do. From data analysis, we can generate insights (now AI can help with that).

     Mohasseb notes that big investments were being made in data analytics and big data. Cloud computing was taking off at the time as well. Computing and data storage costs were dropping. He notes that bigger and more data do not confer strategic advantages without analyzing that data to inform decision-making. Analytics can and often does lead to optimization. Making equipment more efficient through optimization can save money. This continues to be true. He sees data as simply one ingredient in a recipe for success. It is also, he says, a valuable corporate asset. Analyzing it can lead to insight and optimization. In a historical context, he sees the last hundred years as an age of manufacturing followed by an age of distribution, and predicts an age of obsession with the customer that big data can aid.

Let’s not just “compete on analytics.” Let’s “compete on analytically informed and dynamic strategies.”

     He says the battle over analytics will soon be over when all companies can access the same capabilities and intelligence. He also warns that basic business fundamentals should not be ignored.

The science of strategy is to leverage machines and systems to extract insights from data quickly and understandably. However, real competitive edge has always come from comprehension.”

The artful part of strategy is knowing when to go to war and when not to.”

     This refers to knowing when to make certain decisions and moves.

The secret to success is to effectively combine the art and science of strategy.”

     He talks about augmented intelligence that comes from people partnering with machines. We are seeing quite a lot of this now with AI-enabled systems, including sensor-based Internet of Things applications, which enable the collection of vastly more data.

Man-machine teams and adversaries are the future of business competition.”

      He mentions Stuart Firestein, author of Ignorance: How it Drives Science, who advises cultivating ignorance, or ‘not knowing,’ because it can lead us to insights, innovation, and advantages.

     He mentions Columbia Business School’s Ruta McGrath, whose book, The End of Competitive Advantage, notes that stability can be dangerous in a dynamic competitive environment. She cautions that every advantage is temporary.

     Part Three is entitled Breaking Static: Unleash & Embrace. First, he talks about emergence.

Organizations are complex systems. Companies are emergent. They represent a collection of human beings, processes, and practices – they are alive.”

     He also notes that each is distinct, unique, and always changing.

When a group of people (an organization) collaborates, interacts, communicates, and pursues the same purpose, emergence occurs; a collective change happens, a fresh understanding that leads to new decisions, patterns, or changes in direction.”

Your organization is emerging whether you desire it, acknowledge, or ignore it.”

     Next, he talks about connectivity, consistency, and continuity. Optimized connectivity is an essential prerequisite. This involves getting the correct and full signals about performance, the industry ecosystem, the company’s capabilities, and market dynamics.

Connectivity is critical to discovery – when the signals are broken, effectiveness is compromised.”

     Consistency, he says, is vital for data capture and analysis. He says companies should be consistent in measurement and evaluation.

     Continuity involves paying attention to time, he seems to suggest. The timing of business decisions can make or break a company. Better to coordinate with market signals as much as possible.

     He says that “life is about exchange” and therefore we should be cognizant of the value of things being exchanged, including the perceived value.

A winning strategy aims to balance the value delivered to all stakeholders at all times.”

     He says growth, risk, and efficiency must be grouped, monitored, and balanced. 








     Chapter 6: Gaining the Edge, focuses on how to gain that edge, utilizing the evolving caterpillar metaphor as he does throughout the book. First, he notes that “uncertainty is your ally,” so we must become comfortable with it. He tells cautionary tales about the growth of digital industries like Netflix and Amazon, disrupting and replacing brick-and-mortar ones. These new developments reorganized the strategies of many other companies seeking to avoid undesirable outcomes. He says that it is better to get comfortable with probability than certainty. He also gives examples of where embracing certainty was disastrous and where it paid off to embrace uncertainty. He warns that “hope is not a winning strategy.” Disruption risks show that being able to put out fires is a vital skill. The ability to get a whole team to utilize uncertainty as an ally can be very valuable, he suggests. He says that creating cultures of innovation has been beneficial for many of the tech companies. He emphasizes the importance of the free flow of intelligence within an organization, “unconstrained by functions and turfs.”

     Mohasseb advises to “capture and interrogate reality.” He gives Amazon’s development of cloud computing as an example where this has happened. The first step is to appreciate reality, to understand the performance and capabilities of the company, and the fluctuations in markets. He says to “make it achievable” and that describes execution. He also says, “plan to improvise.” Prioritization and timing are important for improvisation.

     Having reviewed thousands of business plans and working with hundreds of entrepreneurs, he cautions:

Experts may advise, “Have a firm conviction about your strategy and pursue it relentlessly.” I disagree. Convictions can be deadly – the wrong convictions will waste your organization’s energy and resources.”

    Mohasseb recommends cultivating “purposeful curiosity” as a means to attract insight. He says that the most common causes of strategic failure are solving the wrong problem or pursuing the wrong opportunity. However, finding the right problems to solve and the right opportunities requires a process of discovery. That process in turn requires effective observation of realities and uncertainties via the scrutiny of data and signals. He says that advantage is found through data analysis. Just having data or technology is not enough. It needs to be analyzed or developed for use. Finding signals in data is what many scientists and strategists do. These days, AI does it very well, oftentimes better or much better than humans do. AI does not forget and can crunch vast numbers quickly, but its ability to strategize is just beginning with agentic AI. This will improve in the future. Identification of challenges and opportunities is one result of data analysis.

Let data analytics constantly deliver the signals, news, and insights – pointing out both direction and progress.”

     More data is usually good, but too much can lead to confusion, he says. I think AI can mitigate that a bit these days.

     He also points out that we as individuals and groups use analytics all the time. It’s what we refer to as common sense in many cases. Strategies must pass the test of common sense. He also recommends keeping strategies simple.

     The final section is Part Four: Doe or Die … Evolve and Thrive. He first states that measuring the effectiveness of a strategy during its implementation is important.

Positive evolutions are purposeful, intelligent, and planned.”

He says that “friction is the unavoidable side effect of change.” Since change is natural and inevitable, so is friction. Obstacles need to be overcome.

     He recommends cultivating a curious and innovative mindset as a positive habit.

     In the final chapter, he speculates a bit about the effects of AI and our growing dependence on machines. Nine years later, we still don’t know what the full impact will be, and predictions are all over the place. He asks whether AI is any different than previous technologies like knives or fire. He notes that we should continue to build and partner with machines and segment our intelligence. That seems to be happening these days.

Politics and religion may divide us, but data and machines could connect us and make us one world. A world where the boundaries of companies, services, and products are hard to distinguish. A world where constant innovation comes from all corners of the earth. Where only the informed can truly evolve and abundance of data end ensuing insights will make the planet more knowledgeable and innovative.”

     Great book!

 

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         This was an interesting book, sometimes fun. It is focused on strategy in a business world prone to disruptions and changing cond...