My life as an entrepreneur has been a fantastic journey of ups and downs. Through it all, I’ve learned a lot in the trenches – living it every day, burning the midnight oil, and then repeating the process over and over again. Sometimes when you’re ‘in it’ that deep, you crave some perspective, which is how I also came to be a voracious reader. I can’t say it enough – reading is one of the most cost-effective and impactful investments you can make in your entrepreneurial journey.

Over the past 20 years, I’ve read hundreds of books. (My wife will diplomatically confirm that we house literally hundreds of books.) In those hundred, a few stand out for their profound impact on not only my career but also the way that I manage my life.

The Hard Thing About Hard Things, Ben Horowitz

The Hard Thing About Hard Things is the first book I read that so accurately portrayed life in a startup. (I’ve read it twice more since the initial reading.) Why does this book matter so much? Horowitz shoots it straight, telling it like it is – the real-down-and-dirty view of a business that is fighting to stay alive despite the odds.

On an even more personal level, this book mirrored my psychological experience in startups more than any other book that I’ve ever read. I believe that much of my success and positive outcomes were driven by my sheer will to win – to keep pushing and never to give up. And this book tells that story – a high-growth business fighting to win and making it happen. This book continues to support you as you make your way through the journey, too; I’ve found myself referring back to it for “advice” in tough times – firing people you care about, making tough decisions, communicating with your board or investors. All the “stuff” no one really talks about.

It’s a powerful read that I strongly endorse for entrepreneurs and aspiring entrepreneurs.

Only the Paranoid Survive, Andy Grove

I bought Only the Paranoid Survive early in my entrepreneurial career. I was young, inexperienced, and still struggling to figure out how I felt about startups – the challenges and the success. In this book, Former Intel COO, CEO, and Chairman, Andy Grove, warns us (‘us’ being any of us, really – not just entrepreneurs) about one of our culture’s biggest threats – the danger of complacency and arrogance.

When companies of any size start to succeed, they experience a tendency to lean into what’s working. They feel like if they’ve found their rhythm; they might as well stay there. But, as we know, the innovative young will gobble up the old and comfortable; the fast and nimble will eat the slow and steady. Grove’s book infused an appropriate amount of paranoia into my early career; the kind of paranoid that helps you to stay innovative, fast, nimble – ahead of the curve.

My biggest takeaway from this read: Never sit idle. Never assume you’ve made it. When you start to feel safe and steady, and comfortable, double your efforts. Innovate. Think. Rethink. Smart paranoia will help drive your success.

The Monk and the Riddle, Randy Komisar

I’ve practiced “lifestyle design” most of my working life. Early in my career, I boldly and unequivocally made decisions to prioritize important life priorities – family, travel, and flexibility. I’ve cared about “where and how” I work. I’ve asked myself “why” I do what I do.

I’ve never been great at “balance,” – but I’ve always been good at “fusion,” fusing together different areas of my life around my priorities. A great example: I’m writing this from my back porch with my dogs at my feet and my wife 10 feet away in the middle of a workday. The Monk and the Riddle is the book that helped me frame this way of working life.

This book is part fiction, part personal experience, but it is a complete manual of sorts that forces you to really think about work and really like about life design.

If you want to crush it AND do it while living a great life – this is a MUST-READ.

The Purple Cow, Seth Godin

As a thought leader, Seth Godin is just the best. I’ve been a fan of his through much (if not all) of my entrepreneurial life. He wrote smart books, taught smart classes, and published smart blogs as I was starting my first tech companies in the mid to late 1990s, so I was digesting and implementing his advice early on.

I recommend any (all, really) his works and his daily blog to any aspiring entrepreneur, but it was The Purple Cow that had the greatest impact on my career, and here’s why: I’m a big believer in brands and a strong advocate for powerful design, and The Purple Cow opened my eyes to the simplicity of what’s possible when you pair brand with design. You should always position yourself and your company so that your product will BE the marketing. It’s really that simple. Make great products. Period.

This served as a foundation for much of our work launching Mountain Khakis. In a retail landscape where we were trying to differentiate the seemingly generic khaki pants, we shifted our thinking to just that – the seemingly generic khaki pant becoming GREAT.

I carry Seth’s lessons from company to company, but, most importantly, I will always shout from the rooftops that we need to build amazing products. The fact that he is the only writer here that I feel comfortable referring to by his first name is proof of another lesson that digs a level deeper into The Purple Cow – you are your best brand; you design your own brand. Buy this book.

I want to hear from you – what books have shaped your entrepreneurial journey, your lifestyle design, and your own brand?

Yours in startups,