The best books for leaders feeling “lonely at the top”

Why am I passionate about this?

I have been a founder, CEO, venture capitalist, buyout specialist, Chairman, author, consultant, and coach. I’ve seen the startup world from every angle and also seen how destructive it can be if we don’t take care of our inner lives. My work now is to help people understand how we can transform ourselves to transform our businesses. These books were helpful to me when I needed them most and shaped not only my leadership approach but also my life. 


I wrote...

Reignition: Transforming Stuck Startups Into Breakout Winners

By Dave Hersh,

Book cover of Reignition: Transforming Stuck Startups Into Breakout Winners

What is my book about?

Nine out of ten startups fail, but founders believe they have an 82 percent chance of success. This disconnect fuels blind optimism and rampant fundraising and kills otherwise promising companies. It doesn't have to be that way. There are consistent patterns that can be corrected or avoided.

An entrepreneur, investor, advisor, and humble contrarian, Dave Hersh (GP, Metamorph; founding CEO of Jive; former board partner, Al6Z) has spent over thirty years building lean, profitable, mission-driven businesses. Bolstered by stories of successes and failures, Reignition is a clear and practical playbook for companies with revenue between $1M and $100M that have seen success but need a second act.

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

The books I picked & why

Book cover of Steve Jobs

Dave Hersh Why did I love this book?

This book came out when I was a struggling founder CEO and hit me in the right way. Steve is clearly a polarizing leader, and for good reason. He’s complex and deeply flawed, but he also created magic products that changed the world. As a founder, you must constantly step back and question your motivations, as they will subconsciously drive your decisions in ways you don’t always consider. 

For me, this was a call to action to understand what it takes to inspire teams to greatness, but it was also a warning to approach it from the right source of inspiration. 

By Walter Isaacson,

Why should I read it?

7 authors picked Steve Jobs as one of their favorite books, and they share why you should read it.

What is this book about?

From bestselling author Walter Isaacson comes the landmark biography of Apple co-founder Steve Jobs. In Steve Jobs: The Exclusive Biography, Isaacson provides an extraordinary account of Jobs' professional and personal life.

Drawn from three years of exclusive and unprecedented interviews Isaacson has conducted with Jobs as well as extensive interviews with Jobs' family members, key colleagues from Apple and its competitors, Steve Jobs: The Exclusive Biography is the definitive portrait of the greatest innovator of his generation.


Book cover of The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

Dave Hersh Why did I love this book?

I was lucky enough to work with Ben at a16z and found him to be a very thoughtful and brilliant guy with deeply held beliefs and perspectives on how to build great technology and organizations.

This book helped me navigate the line between knowing the answers and being stuck in the hardness in my writing and leadership development. It’s also more vulnerable than many other books and serves as a good reminder of why we do it, how hard it can be, and that we’re not alone in that path.

By Ben Horowitz,

Why should I read it?

2 authors picked The Hard Thing About Hard Things as one of their favorite books, and they share why you should read it.

What is this book about?

Ben Horowitz, cofounder of Andreessen Horowitz and one of Silicon Valley's most respected and experienced entrepreneurs, offers essential advice on building and running a startup-practical wisdom for managing the toughest problems business school doesn't cover, based on his popular ben's blog. While many people talk about how great it is to start a business, very few are honest about how difficult it is to run one. Ben Horowitz analyzes the problems that confront leaders every day, sharing the insights he's gained developing, managing, selling, buying, investing in, and supervising technology companies. A lifelong rap fanatic, he amplifies business lessons with…


Book cover of The Thousand Autumns of Jacob de Zoet

Dave Hersh Why did I love this book?

Sometimes, we just need an escape. This fiction book takes place in the Dutch trading post of Dejima in Nagasaki Harbor, Japan. The novel follows the story of Jacob de Zoet, a young and honest Dutch clerk seeking to make his fortune and return to the Netherlands to marry his fiancée.

It’s a fun, escapist read that appeals to founders and builders like me. We follow this self-made hero who is drawn into a complex world he is forced to confront. It’s a journey of personal growth and morality set against a fascinating historical backdrop.

By David Mitchell,

Why should I read it?

5 authors picked The Thousand Autumns of Jacob de Zoet as one of their favorite books, and they share why you should read it.

What is this book about?

The Sunday Times Number One Bestseller, from the author of CLOUD ATLAS and THE BONE CLOCKS.

Longlisted for the Man Booker Prize 2010

'Brilliant' - The Times
'A masterpiece' - Scotsman

Be transported to a place like no other: a tiny, man-made island in the bay of Nagasaki, for two hundred years the sole gateway between Japan and the West. Here, in the dying days of the 18th-century, a young Dutch clerk arrives to make his fortune. Instead he loses his heart.

Step onto the streets of Dejima and mingle with scheming traders, spies, interpreters, servants and concubines as two…


Book cover of Sapiens: A Brief History of Humankind

Dave Hersh Why did I love this book?

Being “lonely at the top” is often a problem of being stuck inside an infinite loop of cycling voices in your head. I can get insanely maniacal about the little things and have difficulty breaking out of the cycle.

This book came at a time when I was deep in one of those cycles. It was a mind-blowing look into why we are who we are and how homo sapiens systematically took over the planet. It was such an “aha” moment for me that it made all the voices go away, and I could see why and how my life was playing out in this way.

By Yuval Noah Harari,

Why should I read it?

21 authors picked Sapiens as one of their favorite books, and they share why you should read it.

What is this book about?

100,000 years ago, at least six human species inhabited the earth. Today there is just one. Us. Homo sapiens. How did our species succeed in the battle for dominance? Why did our foraging ancestors come together to create cities and kingdoms? How did we come to believe in gods, nations and human rights; to trust money, books and laws; and to be enslaved by bureaucracy, timetables and consumerism? And what will our world be like in the millennia to come?

In Sapiens, Dr Yuval Noah Harari spans the whole of human history, from the very first humans to walk the…


Book cover of Radical Acceptance: Embracing Your Life with the Heart of a Buddha

Dave Hersh Why did I love this book?

If there’s one thing I needed more of as a founder CEO (and didn’t know I needed), it was self-compassion. Tara’s amazing book is a calming, kind, and loving “friend” of a book that helps you connect with what matters and how our minds can get in our way.

To get in the best “athletic shape” as a leader, we need self-compassion lest we burn ourselves and our teams out and kill our companies in the process. This book was better than any medication I could have taken to calm my nervous system and make me a better leader. 

By Tara Brach,

Why should I read it?

3 authors picked Radical Acceptance as one of their favorite books, and they share why you should read it.

What is this book about?

For many of us, feelings of deficiency are right around the corner. It doesn’t take much--just hearing of someone else’s accomplishments, being criticized, getting into an argument, making a mistake at work--to make us feel that we are not okay. Beginning to understand how our lives have become ensnared in this trance of unworthiness is our first step toward reconnecting with who we really are and what it means to live fully.
—from Radical Acceptance

“Believing that something is wrong with us is a deep and tenacious suffering,” says Tara Brach at the start of this illuminating book. This suffering…


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The Oracle of Spring Garden Road

By Norrin M. Ripsman,

Book cover of The Oracle of Spring Garden Road

Norrin M. Ripsman Author Of Song Book

New book alert!

Why am I passionate about this?

I love a good short story that can convey character, emotion, and complexity. While a novel allows the writer (and the reader) to delve into the chaotic complexity of a single set of characters, a good short story collection can explore a range of humanity and a diversity of moods or feelings.  This was my motivation in writing my book. I believe a good short story collection on a well-grounded theme (such as the contributions to this list by Doerr, Kundera, and Munro) can often reveal more about human nature than an excellent novel.

Norrin's book list on short stories for a cottage trip

What is my book about?

The Oracle of Spring Garden Road explores the life and singular worldview of “Crazy Eddie,” a brilliant, highly-educated homeless man who panhandles in front of a downtown bank in a coastal town.

Eddie is a local enigma. Who is he? Where did he come from? What brought him to a life on the streets? A dizzying ride between past and present, the novel unravels these mysteries, just as Eddie has decided to return to society after two decades on the streets, with the help of Jane, a woman whose intelligence and integrity rival his own. Will he succeed, or is it too late?

In the tradition of Graham Greene, this is a book about love, betrayal, and life’s heavenly music

The Oracle of Spring Garden Road

By Norrin M. Ripsman,

What is this book about?

“Crazy Eddie” is a homeless man who inhabits two squares of pavement in front of a bank in downtown Halifax, Nova Scotia. In this makeshift office, he panhandles and dispenses his peerless wisdom. Well-educated, fiercely intelligent with a passionate interest in philosophy and a profound love of nature, Eddie is an enigma for the locals. Who is he? Where did he come from? What brought him to a life on the streets? Though rumors abound, none capture the unique worldview and singular character that led him to withdraw from the perfidy and corruption of human beings. Just as Eddie has…


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