Judgment under leverage. Thinking clearly when the downside matters.
Tag: Book Notes
Essays and reflections drawn from books that have shaped how an experienced operator thinks about capital, leadership, discipline, and decision-making.
Ben Horowitz’s The Hard Thing About Hard Things is one of the few business books that tells the truth about what it actually feels like to lead under pressure. No formulas. No cheerful frameworks. Just the raw mechanics of surviving decisions that have no good options. The concept that stayed with me longest is one he calls “Give Ground Grudgingly.”
Give Ground Grudgingly
In The Hard Thing About Hard Things,” Ben Horowitz introduces the concept of “Give Ground Grudgingly,” emphasizing maintaining growth while minimizing degradation. This principle advises leaders to make necessary sacrifices but resist unnecessary losses. It’s about finding the balance between expanding the business and preserving its core values and capabilities. Essentially, Horowitz is advocating for cautious and strategic growth, ensuring that as the company evolves, it retains its essential strengths and integrity, thus degrading as slowly as possible.
American Football Analogy
There is a great analog to this concept in American football. An offensive lineman’s job is to protect the quarterback from onrushing defensive linemen. If the offensive linemen attempt to do this by holding their ground, the defensive lineman will easily run around them and crush the quarterback. As a result, offensive linemen are taught to lose the battle slowly or to give ground grudgingly. They are taught to back up and allow the defensive lineman to advance, but just a little at a time.
When you scale an organization, you will also need to give ground grudgingly. Specialization, organizational structure, and process all complicate things, and implementing them will feel like you are moving away from common knowledge and quality communication. It is very much like the offensive lineman taking steps backward. You will lose ground, but you will prevent your company from descending into chaos.
This is the operator’s dilemma in a single phrase. You will lose ground. The question is whether you lose it on your terms or someone else’s. Every scaling decision I have made — adding structure, formalizing process, accepting slower communication — has felt like taking a step backward. The discipline is knowing that the step backward is what keeps you from getting sacked.
What we eventually accomplish in life may depend more on our passion and perseverance than on our innate talent - Angela Duckworth, Grit (2016)
📚 Core Insight
Success is rarely about raw talent — it’s about relentless passion, perseverance, and purpose.
Angela Duckworth’s research shows that grit — sustained effort over years, even decades — outpaces natural ability.
In leadership, sports, and life, greatness is the result of thousands of ordinary efforts compounded over time, fueled by belief, practice, resilience, and a clear sense of purpose.
Grit isn’t a fleeting burst of effort — it’s a culture you build within yourself and, eventually, within the teams you lead.
In Grit: The Power of Passion and Perseverance, Angela Duckworth unpacks the attributes/traits of those individuals who possess grit which is defined as holding the same top-level goal for a very long time and having the passion and perseverance to see your ultimate goal through.
She challenges the unconscious biases we all have towards talent, especially in the way that we all rush to anoint people as extraordinarily talented whenever they accomplish a feat worth writing about. As much as talent counts, effort counts twice as you can see in the following picture of skill and achievement:
What we all achieve depends on talent (how fast we improve skill) and our effort. But as you can see in the above picture, effort factors in the calculations of achievement twice. This is because effort builds skill and at the very same time, effort makes skill productive!
Similar to the findings of Daniel F. Chambliss by the end of the book it is clear the most dazzling human achievements are, in fact, the aggregate of countless individual elements, each of which is, in a sense, ordinary. High level of performance is, in fact, an accretion of mundane acts.
Steve Young: An Example of a Paragon of GRIT
“You cannot quit. You have the ability, so you need to go back and work this out.” - Steve Young’s Dad, (circa 1980s)
Steve Young is the epitome of a GRIT Paragon. When he was a freshman at BYU, he was the 8th string quarterback and was barely even getting any practice time. Like most freshmen when things don’t go according to plan, Steve called his father (whose nickname was actually Grit).
Steve’s dad basically said the following: “You can quit but you can’t come home because I’m not going to live with a quitter. You’ve known that since you were a kid. You’re not coming back here.”
With the words of his father ringing in his ears, Steve Young stepped up his game and put the work in. By all accounts, he threw over 10,000 spiral passes at a practice net the summer between his freshman and sophomore year. By his sophomore year, he had risen to QB2 and by his junior year he was BYU’s starting QB. In his final year with the Cougars, Steve Young won the Davey O’Brien award for the most outstanding college quarterback in the country.
Then … It happened all again when he got to the San Francisco 49ers. He spent 4 years on the bench as the backup to four-time Superbowl champion, Joe Montana. And because of his experience at BYU, Steve stayed, learned, and flourished under Montana’s apprenticeship. He eventually got his chance and the rest is history.
Steve Young: A Gridiron Paragon of Grit. From every touchdown to each hard-fought comeback, his relentless determination on the field defines the true essence of grit. A quarterback icon who faced challenges head-on, Young embodies the spirit of unwavering passion and perseverance.
When Steve Young retired, he was the highest-rated quarterback in NFL history.
Final Thoughts
Superlative performance is really a confluence of dozens of small skills or activities, each one learned or stumbled upon, which have been carefully drilled into habit and then are fitted together in a synthesized whole.
People with grit are paragons of perseverance and effort. As much as talent counts, effort counts twice as much with them. They develop their skills by hours and hours and hours of deliberate practice beating on their craft. They master the capacity to do something repeatedly, to struggle, and to have patience over the long-term. But most importantly, they develop the stamina to go over something again and again and again no matter how difficult it is.
In closing, greatness is actually doable because greatness is many, many individual feats, and each of them is doable. When it comes to how we fare in the marathon of life, effort counts tremendously, and consistency of effort over the long run is everything. Great things are accomplished by those people whose thinking is active in one direction, who employ everything as material, who always zealously observe their own inner life and that of others, who perceive everywhere models and incentives, who never tire of combining together the means available to them.
Little Habits and Characteristics That Can Make You More Gritty
Seek to continuously improve
Focus on the daily discipline of trying to do things better than you did yesterday
Remember that the 10-Year Rule Applies to developing skills: thousands and thousands and thousands of hours spent in deliberate practice over years and years and years
Love what you do
Remember that sustained effort over the long-run counts more than talent
Interpret setbacks and failure as a cue to try harder rather than as confirmation that you lack the ability to succeed
