Second-level thinking & how to get better at it

Second-level thinking is a deep and complex approach to decision-making that goes beyond superficial analysis. Second-level thinkers ask probing questions and consider multiple perspectives to gain a more comprehensive understanding of a situation. They examine a range of potential outcomes, assess probabilities and compare their views to the consensus. They uncover insights that others may overlook, allowing them to make more informed decisions and achieve superior results. By thinking unconventionally and holding well-reasoned, non-consensus views, second-level thinkers position themselves to succeed in investing, business and life.

But how do they do it? Howard Marks is the Chairman and cofounder of Oaktree Capital Management and one of the finest purveyors of second-level thinking (sometimes referred to as second-order thinking). In his book The Most Important Thing: Uncommon Sense for the Thoughtful Investor, Marks explains why second-level thinking is so important and how you can get better at it.

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Col. John Boyd’s Strategy Masterclass: “The Fighter Pilot Who Changed the Art of War”

Robert Coram, author of Boyd: The Fighter Pilot Who Changed the Art of War describes John Boyd as “first, last and always a fighter pilot – a loud talking, cigar-smoking, bigger-than-life fighter pilot”. But also as more than that: “he was that rarest of creatures – a thinking fighter pilot.” Boyd is widely considered to be one of the world’s greatest military strategists, despite the fact that it’s unlikely you have ever heard of him. Over his career he bought the Air Force its Aerial Attack Study, invented Energy-Maneuverability (E-M) Theory, was the father of the F-15 and F-16 fighter jets and created a decision making framework called the OODA loop. His thinking about strategy spread across the US armed forces: his Patterns of Conflict briefing provided the basis for the US military’s strategy in the first Gulf War, leading to their 100 hour victory. It still underpins US Marine Corps fighting doctrine to this day.

John Boyd was an endearing eccentric and strategic genius who is brought wonderfully to life by author Robert Coram in his meticulously researched book. Coram demonstrates what one man, surrounded by a few devoted and loyal Acolytes, can do to change the world. Maneuverability, as it relates to military (and business) strategy, we learn is key. 

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Daniel Kahneman on the cognitive biases of entrepreneurs

Thinking Fast and Slow is a book about biases of intuition. It’s ideas are so potent that they won it’s author Danuel Kahneman a Nobel in economics. Kahneman identifies that the human brain works very well most of the time and our judgments are sound. However, it is prone to engage in a number of fallacies and systematic errors that lead to flawed opinions and adverse decision making, otherwise known as cognitive biases. We assume certain things automatically without having thought them through carefully. Kahneman calls these assumptions heuristics and, for entrepreneurs, they can be deadly. An awareness of them is the first step to countering them.

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The best business & leadership quotes from ‘Shoe Dog’ by Phil Knight

Phil Knight is the founder, former CEO and now Executive Chairman of Nike. In Shoe Dog: A Memoir by the Creator of Nike he tells his story of taking the business from humble origins, through an IPO in 1980 and onto its current $30 billion market capitalisation.

Nike is still widely regarded to be one of the most innovative companies in the world. Phil Knight started and grew the business out of the back of a van in the early 1970s. A Stanford graduate, avid reader of the Classics and books about military strategy, and a natural introvert, he captures a wonderful story about what he calls his Crazy Idea and the determination and grit it takes to become successful beyond what he’d ever imagined. In Shoe Dog, he also includes some wonderful accounts of the hustle and sometimes downright dirty tactics that it can take to overcome the odds: “you are remembered for the rules you break” is his mantra throughout the book. I’ve captured the best of the rest of his business and leadership wisdom in the quotes from the book below.

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Yuval Harari explains Capitalism

Yuval Noah Harari’s book Sapiens: A Brief History if Humankind charts our origins from hunter gatherers 2.5 million years ago on to the rise of Homo Sapiens 200,000 years ago. He takes the reader through the Cognitive Revolution 70,000 years ago, the Agrarian Revolution 10,000 years ago, into the Scientific Revolution in the 1500s, the Industrial Revolution in the late 1700s and on to the present. Harari covers a lot of ground that includes a deep dive into capitalism: “an economic-led system based on private ownership of the means of production and their operation for profit”. He explores how something that began as a theory about how the early economy of the modern age functioned, has grown into much more than an economic doctrine.

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Cancer & Entrepreneurshit

On 13th February 2015 I was diagnosed with Stage 3 colorectal cancer. At the beginning of August this year my treatment was complete. After nearly two years of grappling with a life-threatening illness, whilst at the same time hanging on to the bones of a business that I had set up just eighteen months before diagnosis, it is time to embrace the new normal. This is my story about cancer and entrepreneurshit. Continue reading →

Cancer & Entrepreneurship

Disillusioned with the corporate world and mesmerised by a whole season living in my campervan in the French Alps, I decided it was time for another change. In September 2013 I resigned from Deloitte Consulting and set up my own business as an entrepreneur coach. After five months spent climbing and skiing consequential lines, my rationale was simple: entrepreneurship was going to push me hard and I might end up penniless, but I’d learn a lot and it couldn’t kill me. On that basis, and with some ideas about how I’d grow my business in mind, the decision was made. Just 18 months into my entrepreneurial journey I was told I had Stage 3 colorectal cancer. That most definitely could kill me and I was petrified.

I don’t want to use my illness to define me but it hit at a very specific time in my life. Given the craziness of the experience, it feels like a missed opportunity not to share it and raise awareness. I didn’t keep a diary, so this is an opportunity for memories and personal reflection. I have also recorded a Podcast with Jerry Colonna and the gang at Reboot, a coaching company that helps people to deal with the internal ups and downs of entrepreneurship.

This is my story of being an entrepreneur with cancer.

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What’s wrong with The Lean Startup

The Lean Startup, by Eric Ries, was first published in 2011 and has since become the bible for startup entrepreneurs around the world. More recently, the approach outlined in The Lean Startup has received criticism, but is that fair? In this post I argue that it is not, because that is all it is, an approach, albeit a very good one. 

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