Reboot: Leadership and the Art of Growing Up

Reboot is a book by Jerry Colonna, a venture capitalist who is now a startup coach. Since his VC days, he's taken a huge dive into Buddhism and Jungian therapy. This book aims to help founders develop psychological patterns and behavioral patterns to help them succeed. On Fred Wilson's blog, I've read that Jerry Colonna is a great coach and many others have acclaimed the same thing. As a matter of fact in the introduction of the book he states:> "Reading the book should feel like a coaching session or boot camp"It is anything *but* that. Which is very ironic because the introduction is written extremely well yet immediately the first chapter transports you to an empty white room with two stools. On the other stool is Jeremy Colonna just talking without giving you eye contact or any physical indication that you're there. And just talks. If you take a potty break between chapters, you come back and find that he's still been talking without having noticed that you went to the bathroom. After a while, you wonder if he's okay.I haven't encountered a book so difficult to read purely due to the author's laziness. I can acknowledge that there are lessons and important takeaways in each chapter. However, this book is not a business or coaching book. It's really Jerry Colonna's stream of consciousness and memoirs that was written for himself or maybe close friends he knows of.This book is a swamp of extremely long set of anecdotes about certain memories of his startup career. Random anecdotes do not make a story. For example, the first chapter is an almost *whopping* 20 pages of his childhood memories. It goes into 9/11, kids who used to bully him, 3 paragraphs about the weather and seasons, his dad's relationship with his grandpa, his mom having several children. However, you, the reader, are left utterly confused when the coaching will begin. Maybe you're still in the introduction? Maybe you missed the coaching? So you reread the chapter and confirm that you aren't crazy, Jerry was just talking into the void.While the grammar, prose, and presentation of the book is very nice and clean, it does not look like the author or editor put any effort into asking serious questions like:- Why is this paragraph, this sentence , this story, or important to my reader?- Is this lesson that I learned while running a business something that my reader can learn?- What journey should the reader go on? What is my responsibility as an author to guide them?My suggestion, this should have been **two books:**- One book that is Jerry Colonna's book about his memories that is for the audience that is Jerry Colonna and his friends. Which I suspect are all the 5 stars on amazon, whose reviews don't even indicate that they've read the book at all; just are praising the person.- Another book that is for the audience of startup founders and executive members that is heavily re-engineered to enlighten **them**, the customer. The people who wrote the 2 star reviews who were also left dumbfounded like me.It's such a shame, because the way the book is written is what is holding it back. There are lessons about finding purpose, being honest to yourself, self inquiry and the values of overcoming challenges somewhere in pages. But Jerry didn't seem to want to share them or be clear at all. It was made purposefully difficult to read with extremely forced and artificial Buddhist commentary that only had a purpose of being theatrical. I think it's critical that this book be rewritten to surface up the important and tone down the noise.

Jerry Colonna is the wisest person I know on issues of leadership, organizational dynamics, thriving in the workplace, and being fully present to ourselves and each other, and to our work. He’s a coach and consultant who never advises from 35,000 feet, but dives into the thickets of what it means to be human, grounding his work in messy experience, not in theoretical abstractions. He is also a truly good man, who brings intelligence, compassion, common sense, and the saving grace of laughter to everything he does. Whether or not you are a CEO (I am not), Colonna is a good guide for everyone who knows that he or she still has growing to do (that describes me). If you’re interested in the issues I’ve named, I highly recommend this book, subtitled "Leadership and the Art of Growing Up.” God knows we can use all the grownups we can find these days!

I did not know anything about Jerry Colonna until Seth Godin recommended "Reboot" on his blog. I trust Seth's taste, so I picked it up and ended up reading it in two sittings. The main premise of the book, in Colonna's words: "I believe that better humans make better leaders... that the process of learning to lead well can help us become better humans. By growing to meet the demands of the call to leadership, we’re presented with the chance to finally, fully, grow up."What I like about this book:• Colonna has been a big-cheese venture capitalist (co-founder of Flatiron with Fred Wilson), successful entrepreneur, and CEO coach. The stories with which he illustrates the principles come from first-hand experience, not second- or third-hand journalism, and thus ring true.• The archetypes that Colonna introduces to help us become better leaders have staying power: the Broken-Open Hearted warrior who can empathize and therefore lead better; the Irrational Other, who can get us stuck in self-righteousness; the Crow, whose protective negativity we'd do better to embrace than ignore.• Colonna shares the teachings of his own seriously wise teachers: leading American Buddhist Sharon Salzberg; Parker Palmer; and his late therapist, Dr Avivah Sayres. The whole book is permeated with teachings from Eastern wisdom and contemplative traditions, of which I'm a perennial fan.• The journaling prompts at the end of each chapter are deep. The three that I liked the most, which may well be the centerpiece of the book: "What am I not saying that needs to be said? What am I saying that’s not being heard? What’s being said that I’m not hearing?" And a profound question he asks all his clients: “How are you complicit in creating the conditions of your lives that you say you don’t want?”The book is also a candid memoir of Colonna's struggles: a turbulent childhood with an alcoholic dad and mentally ill mom; suicidal ideations; debilitating migraines; crippling self-doubt. Colonna's transformation of the raw material of heartbreak into success and stewardship is the inspirational rocket fuel of this book.In terms of total quantity of life-altering wisdom, I'd put this book alongside "The Untethered Soul" and "The Power of Now." It's written with candor, compassion, and grace. Get it for an entrepreneur or leader you love. I'm hoping that's you.-- Ali Binazir, M.D., M.Phil., Happiness Engineer and author of  The Tao of Dating: The Smart Woman's Guide to Being Absolutely Irresistible , the highest-rated dating book on Amazon, and  Should I Go to Medical School?: An Irreverent Guide to the Pros and Cons of a Career in Medicine