Over the years of working at a startup, I’ve found a number of books invaluable to help see around corners and improve as an operator. Since it took me a long time and a lot of exploration to settle on these picks, I’ve compiled a reading list that I consider very helpful, if not essential, for people working at a fast-moving company.
Many of these books are particularly useful for tech startups (which is my own background), but all are generally applicable to a variety of businesses large and small. I’ve personally found the advice and stories in these books to be both inspiring and immediately useful, and I hope that this list will be helpful to others who are operating, starting, or working at startups.
The High Growth Handbook
The High Growth Handbook is a how-to guide on building a high-growth technology company in the Silicon Valley mold: raising VC money, winning with technology, and growing fast. It was written by Elad Gil, who’s been an investor and operator at a variety of successful companies.
What I especially liked about this book is that it’s both specific and proscriptive. The book has very targeted tactical advice for technology startups (for example, advice on how your product management team should operate, or how to run a board meeting), and also doesn’t shy away from providing a point of view on what works and what doesn’t. I find that non-specific advice can often end up being less actionable, and really appreciated that the author is opinionated. It’s easy for management books to read like horoscopes, with advice that is open to interpretation. The High Growth Handbook is anything but.
Read if you are looking for targeted advice relevant to high-growth technology companies.
Skip if you are not a high-growth technology company.
The Hard Thing About Hard things
The Hard Thing About Hard Things is a combination memoir and guidebook for building a technology company. It’s written by Ben Horowitz, who worked at Netscape, was founder/CEO of an early cloud infrastructure company that was acquired by HP, and then started the well-known VC firm Andreesen Horowitz. Much of the book focuses on his experiences at Opsware (formerly Loudcloud), and the team’s trials and tribulations through the Dotcom bubble.
This book does a better job than most that I’ve read at distilling the hard parts of working at a startup – especially one that does not enjoy the monopolistic dominance of Google or Facebook. Scaling a startup is a struggle for most of us mere mortals, and Horowitz does a good job of capturing the emotions at play as fortunes rise and fall.
This book is a great complement to The High Growth Handbook. Both are specifically quite relevant to technology companies, but the advice in THTAHT is both less targeted but also less obvious, especially for a first time manager. I also find it to be a very engaging, entertaining read.
Read if you are looking for fun anecdotes and lessons that are helpful for technology companies, or if you want to be entertained while also learning about management and leadership.
Skip if you are looking for a high density of highly specific and actionable advice.
Shoe Dog
Shoe Dog is a memoir of the early years of Nike, written by Nike’s founding CEO Phil Knight. It tells the story of the early years of the company, from shortly before its founding to roughly the time of its IPO roughly 15 years later. Fair warning that about halfway through this book, if you’re anything like me, you will be consumed by an overpowering desire to buy a new pair of Nikes whether you need them or not.
This is one of my favorite books that I’ve ever read. One element that I thought was particularly excellent was the focus on the people involved in the story – Knight’s cofounder, early employees, partners, investors, and even their lawyers. Both The Hard Thing About Hard Things and Shoe Dog are startup memoirs, but Shoe Dog captures both the incredible highs and the terrifying lows (THTAHT really only evokes the latter).
While not strictly a “business book” in the sense of teaching you how to succeed at business, “Shoe Dog” is a really beautiful story that captures the feeling of a startup… when things go well. It’s almost certainly written with heavily rose-tinted glasses, and Nike is worth over $100B which gives the book the advantage of being the origin story of greatness. Nike as a brand is also just way cooler than virtually every tech startup and legitimately did change the ~50,000 year old shoe industry, so I found it a lot easier to be perhaps inordinately impressed by what Phil Knight has to say.
Read if you want to be inspired, or you want to understand what a startup feels like when it’s going well.
Skip if you are looking for actionable business tips or only care about the tech industry. If it’ll bother you that history is written by the victors, and Nike is one of the most victorious companies in recent memory.
High Output Management
High Output Management is a tactical management book written by Andy Grove, third CEO and very early employee of Intel. Andy Grove and the leadership team that he built at Intel were extremely influential in Silicon Valley and the tech industry in general, ultimately influencing the leadership practices of many of the largest tech companies; OKRs were among the more famous concepts that he and his team pioneered.
High Output Management contains a very high density of practical management advice and can deliver value to anyone who has to work with people for their job (ie, almost all corporate workers). The book spans many different topics but all are related to operating teams and being a great manager in a general sense. If you read and internalize High Output Management, I expect that you’ll dodge around 50% of the unforced management errors that you might face. It’s an extremely useful book.
I’ll admit that I found it a bit dry at times, but it’s such a seminal book and so widely applicable that I consider it required reading.
Read if you are looking for actionable management advice that is applicable to virtually any industry. If you are managing (or may one day manage) a team of any size.
Skip if you want to be entertained. But really… don’t skip it.
Extreme Ownership
Extreme Ownership is a series of military anecdotes applied alongside business lessons. It was written by two former Navy SEAL officers who now run a leadership consulting firm. When the authors served in Iraq, their team included soldier-celebrities such as the “American Sniper” Chris Kyle and a guy with one of the most over-the-top resumes in history. One of the authors, Jocko Willink, hosts a popular podcast and looks like a cross between a GI Joe action figure and a silverback gorilla.
“Extreme Ownership” is a quick and accessible read, and most of the takeaways are quite actionable. My favorite part of this book is that it viscerally describes the significance of one of the most important leadership traits for a startup: proactivity and a sense of ownership (unsurprising given the title). The central lesson of the book is that you need to own your decisions and be proactive, and that good things flow from that pattern.
Despite being short and straightforward, the book has a surprisingly thorough treatment of the concepts that it presents. The authors don’t just present an idea and let it dangle, they’ll actually discuss it in multiple ways to ensure that it sinks in unambiguously. The tradeoff is a lack of breadth – the entire book only covers about a dozen basic leadership concepts.
Even years after I read the book, I was surprised to find that some sections of the book continued to resonate. One of the chapters that I most enjoyed discussed the idea that great leadership is contagious and enduring – effective leaders can quickly turn around low-performing teams, and their legacy tends to remain even after they’re gone. I’ve since had the chance to observe this at length, and I’ve been impressed by how on-point I’ve found many of Extreme Ownership’s observations to be.
Read if you’re looking for a quick useful read, or you enjoy military stories.
Skip if you’re looking for a very high density of takeaways, or management advice that is industry-specific.