The Hard Thing About Hard Things: Free Bullet Point Book Summary
The author's upbringing in Berkeley, California, surrounded by a diverse group of friends, instilled in him
the importance of perspective.
While at Columbia University, studying computer science, Horowitz immersed himself in the burgeoning hip-hop
scene, resonating with its portrayal of ambition and struggle.
Working at Netscape with fellow genius Marc Andreessen, Horowitz witnessed the transformative power of the
internet through the success of Mosaic, the first web browser. This experience, coupled with his time at America
Online, solidified his belief in the internet's potential to revolutionize businesses. Recognizing the need for
cloud computing in the late 1990s, Horowitz joined forces with Andreessen to co-found Loudcloud, the first cloud
Seeking rapid growth, Ben Horowitz and Marc Andreessen secured millions for Loudcloud during the dot-com
bubble. However, the company's rapid expansion soon collided with the market crash, leaving them desperately
seeking funding. With limited options, Horowitz took the controversial step of taking Loudcloud public despite its
lack of IPO readiness, guided by his mentor Bill Campbell.
Facing bankruptcy and the aftermath of 9/11, Horowitz made the unpopular decision to sell Loudcloud while
retaining its cloud software, Opsware. This "wartime CEO" approach, focused on survival above all else, saved the
company but required Horowitz to explain his controversial actions to his employees.
With Opsware separated from Loudcloud and plagued by issues, Horowitz released it anyway to learn from its
flaws. He saved a critical contract by offering unexpected value beyond Opsware's core functionality.
To turn Opsware into a winning product, Horowitz challenged his engineers to identify an unmet need, and
this led them to automate networks.
The company's focus, combined with rising cloud computing adoption, led to a successful sale to Hewlett
Packard for $1.65 billion, marking a rare success story amidst the dot-com bubble burst.
“The hard thing isn't setting a big, hairy, audacious goal. The hard thing is laying people off when you
miss the big goal. The hard thing isn't hiring great people. The hard thing is when those “great people” develop a
sense of entitlement and start demanding unreasonable things. The hard thing isn't setting up an organizational
chart. The hard thing is getting people to communicate within the organization that you just designed. The hard
thing isn't dreaming big. The hard thing is waking up in the middle of the night in a cold sweat when the dream
turns into a nightmare.”
Every CEO dreams of building a successful, world-changing company and getting rich, but inevitably faces
crises and setbacks ranging from the macro (e.g., market crashes) to the micro (e.g., poor hiring decisions) that
challenge those dreams. This conflict between aspirations and reality that all CEOs encounter is dubbed
The Struggle. Though draining, The Struggle is where greatness can emerge.
Problems are inevitable, dwelling on them is unproductive. The CEO's role is to find creative solutions and
move forward, not be paralyzed by past mistakes or future uncertainties.
Racecar drivers concentrate on the road ahead rather than all the surrounding hazards. To conquer their own
psychological struggles as a leader, a CEO should mimic racecar drivers and learn to focus on solutions, not
Transparency breeds trust. Open and preemptive communication about company challenges fosters a healthier
work environment and empowers employees to be honest as well.
Positivity delusion refers to the misconception that employees require insulating from harsh
Layoffs are difficult and CEOs should own their responsibility for hiring errors.
Announce layoffs immediately to minimize anxiety and speculation. Delaying inevitable layoffs creates
uncertainty and damages trust.
Treat departing employees fairly by offering generous severance packages and positive references. This
fosters goodwill, eases the transition for departing employees, and helps future recruitment.
Don't sugarcoat the layoffs. Take ownership and acknowledge that the company failed the employees by
necessitating layoffs. Explain that the company missed its goals, requiring difficult decisions like reducing
“If you are going to eat sh*t, don't nibble.”
Do not publicly berate anyone.
We all have a natural tendency to lie to ourselves to avoid painful truths, thus businesses often shy away
from confronting problems head-on. However, CEOs must embrace the reality that complex issues rarely have easy
solutions. Difficult decisions and hard work are the path to progress.
Ultimately, stakeholders only care about results, not the CEO's effort or the pain endured in making
difficult choices. Excuses are irrelevant. Delivering results is everything.
People are a company's greatest asset. CEOs should hire for strengths rather than lack of weaknesses,
seeking people with abilities the company particularly requires even if they have flaws.
“Take care of the people, the products, and the profits -- in that order.”
There are two dangerous mismatches when hiring executives.
Rhythm mismatch: For example, a large company executive's habit of waiting for instructions rather than
showing initiative will clash with the fast-paced environment of a startup.
Skillset mismatch: For example, startup success requires adept hiring, domain expertise, creative
process-building, and identifying new opportunities, whereas large organizations prioritize complex
decision-making, communication, and organizational design.
Training and clarity around expectations and performance are essential for both employees and executives,
noting that those from large companies may struggle in smaller ones.
“A lot of companies think their employees are so smart that they require no training. That's
“Sometimes an organization doesn't need a solution; it just needs clarity.”
Careful hiring and HR processes are essential to ensure management quality.
CEOs, executives and managers must give and receive constructive feedback regularly.
Sh*t sandwich: a guideline to provide feedback where the unpleasant criticism is sandwiched between
comments. Seniors may find this method insincere.
Though some conflict is inevitable, screening for team-oriented ambition during hiring helps prevent selfish
Hire for specific and immediate needs, not projected ones, to ensure efficient scaling and avoid unnecessary
The CEO role is emotionally demanding, requiring resilience strategies to withstand continual pressures,
unpopular decisions, and flexible thinking when problems have unclear solutions.
“Whenever I meet a successful CEO, I ask them how they did it. Mediocre CEOs point to their brilliant
strategic moves or their intuitive business sense or a variety of other self-congratulatory explanations. The
great CEOs tend to be remarkably consistent in their answers. They all say, ‘I didn't quit.'”
Great CEOs are not born, but cultivated.
Great CEOs excel at two crucial things: finding the right direction for their company and inspiring everyone
to follow. They do this by articulating a compelling vision, communicating with authenticity and motivation, and
driving execution with decisiveness and conviction.
Two leadership styles exist for CEOs: Ones and Twos. Ones
prefers to make big decisions and define the path, while Twos excel at implementation. Both types benefit from
developing skills outside their comfort zones to achieve true leadership mastery.
Companies face two distinct environments: peaceful growth or wartime survival.
Peacetime CEOs focus on enhancing existing advantages and encouraging creativity (e.g, Google lets
use 20% of time for independent projects, sometimes they turn into full Google products).
Wartime CEOs make decisive pivots and fight for survival in the face of threats (e.g., Andy Grove saved
Intel by pivoting the company from semiconductors to microprocessing in dire times).
“What's the secret to being a successful CEO? Sadly, there is no secret, but if there is one skill that
stands out, it's the ability to focus and make the best move when there are no good moves.”
Though different personalities can succeed, effective CEOs are strong leaders, performing under pressure
with courage to set direction, making tough calls, aligning the organization behind decisions, and achieving
CEOs should encourage creativity and not over-emphasizing accountability at the expense of
Selling your company requires navigating emotional and rational hurdles. Every situation is different, but
in general, you should not sell if you have an early lead in a sizable market you can still dominate.