Top Takeaways For Startup Founders And CEO’s From Ben Horowitz Book “The Hard Thing About Hard Things”

My highlighter ran out of juice on the very last page.

Harry Alford
humble words
Published in
6 min readAug 13, 2016

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When you are building a business, there are no easy answers. In his new book ,The Hard Thing About Hard Things, Ben Horowitz is brutally honest about what it takes to run a successful startup. Horowitz details his journey as an entrepreneur/cofounder of Loudcloud and CEO of Opsware to eventually cofounding the well-respected VC firm, a16z.

Although I haven’t led a startup to IPO or a $1.6 billion sale, Horowitz appears relatable, amplifying business lessons with rap lyrics beginning each chapter. I dragged my highlighter across thousands of lines till I had used the very last drop of bright yellow ink. Towards the bottom of the final page Horowitz pens, “embrace the struggle.” I couldn’t help but reflect on all of the one-liners and passages from Horowitz’s own struggles and triumphs that business schools don’t cover. Below is a list of the top takeaways from one of the best books I’ve ever read:

There are no shortcuts to knowledge, especially knowledge gained from personal experience. (4)

Colin Powell says that leadership is the ability to get someone to follow you even if only out of curiosity. (5)

Looking at the world through such different prisms helped me separate facts from perception. (5)

During this time I learned the most important rule of raising money privately: Look for a market of one. You only need one investor to say yes, so it’s best to ignore the other thirty who say “no.” (20)

During the road show, as a way to break tension, Marc (Andreessen) would say, ‘Remember, Ben, things are always darkest before they go completely black. (28)

If you are going to eat shit, don’t nibble. (28)

As painful as it might be, I knew that we had to get into the broader market in order to understand it well enough to build the right product. Paradoxically, the only way to do that was to ship and try to sell the wrong product. We would fall on our faces, but we would learn fast and do what was needed to survive. (40)

Finding out the right product is the innovator’s job, not the customer’s job. (49)

Markets weren’t ‘efficient’ at finding the truth; they were just very efficient at converging on a conclusion — often the wrong conclusion. (52)

Startup CEOs should not play the odds. When you are building a company, you must believe there is an answer and you cannot pay attention to your odds of finding it. You just have to find it. It matters not whether your chances are nine in ten or one in a thousand; your task is the same. (59)

People always ask me, ‘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. It’s the moments where you feel most like hiding or dying that you can make the biggest difference as a CEO. (59)

If you don’t want to be great, then you never should have started a company. (63)

When a company starts to lose its major battles, the truth often becomes the first casualty. (85)

Nobody cares…A great reason for failing won’t preserve one dollar for your investors, won’t save one employee’s job, or get you one new customer. It especially won’t make you feel one bit better when you shut down your company and declare bankruptcy. (92)

All the mental energy you use to elaborate your misery would be far better used trying to find the one seemingly impossible way out of your current mess. Spend zero time on what you could have done, and devote all of your time on what you might do. Because in the end, nobody cares; just run your company. (92)

Take care of the people, the products, and the profits — in that order. (93)

Being a good company doesn’t matter when things go well, but it can be the difference between life and death when things go wrong. Things always go wrong. Being a good company is an end in itself. (102)

One of the great things about building a tech company is the amazing people that you can hire. (109)

Good product managers focus the team on revenue and customers. Bad product managers focus the team on how many features competitors are building. (112)

The very best way to know what you want is to act in the role. Not just in title, but in real action. (126)

At a basic level, metrics are incentives…It’s important to supplement a great product vision with a strong discipline around the metrics, but if you substitute metrics for product vision, you will not get what you want. (132)

You should strive to hire people with the right kind of ambition. (155)

Everyone views the world through her own personal prism. (156)

Bringing in the right kind of experience at the right time can mean the difference between bankruptcy and glory. (170)

If you want to make something from nothing, you have to take risks and you have to win your race against of time. (175)

The primary thing that any technology startup must do is build a product that’s at least ten times better at doing something than the current prevailing way of doing that thing. Two or three times better will not be good enough to get people to switch to the new thing fast enough or in large enough volume to matter. (179)

Dogs at work and yoga aren’t culture. (183)

Get a mentor. (185)

Offensive lineman are taught to lose the battle slowly or to give ground grudgingly. When you scale an organization, you will also need to give ground grudgingly. (187)

The first rule of organizational design is that all organizational designs are bad. (188)

Your goal is to choose the least of all evils. (188)

You want to optimize the organization for the people — for the people doing the work — not for the managers. Most large mistakes in organizational design come from putting the individual ambitions of the people at the top of the organization ahead of the communication paths for the people at the bottom of the organization. (190)

Hiring scalable execs too early is a bad mistake. There is no such thing as a great executive. There is only a great executive for a specific company at a specific point in time. (194)

Perhaps the most important thing that I learned as an entrepreneur was to focus on what I needed to get right and stop worrying about all the things that I did wrong or might do wrong. (200)

Focus on the road, not the wall. (207)

Don’t punk out and don’t quit. (208)

Decisions only get scarier as a company grows. (210)

Courage, like character, can be developed. (212)

Technological advances have dramatically lowered the financial bar for starting a new company, but the courage bar for building a great company remains as high as it has ever been. (213)

The enemy of competence is sometimes confidence. (222)

Peacetime CEO knows that proper protocol leads to winning. Wartime CEO violates protocol in order to win. (226)

Being CEO requires lots of unnatural motion. To be a good CEO, in order to be liked in the long run, you must do many things that will upset people in the short run. (230)

Bad news travels fast and good news travels slowly. (234)

Past performance is no guarantee of future results. (242)

First rule of entrepreneurship: there are no rules. (243)

The difference between being mediocre and magical is often the difference between letting people take creative risk and holding them too tightly accountable. (251)

One day you are Terrell Owens and the next day you are Terrell Owens. (254)

When analyzing whether you should sell your company, a good basic rule of thumb is if (a) you are very early on in a very large market and (b) you have a good chance of being number one in that market, then you should remain stand-alone. (258)

The best entrepreneurs will only work with the best venture capital firms. (267)

The only way to learn how to be a CEO is to be a CEO. (269)

Hard things are hard because there are no easy answers or recipes. (274)

Embrace your weirdness, your background, your instinct. (275)

To gain full context surrounding each takeaway, I highly recommend you reading this entrepreneurial management classic yourself.

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Harry Alford
humble words

Transforming enterprises and platforms into portals to Web3