Books Of Mentors

I’ve recently discovered a book genre that I love: collections of advice from a large number of mentors, experts, or people otherwise considered to be the best at what they do.

My first exposure to this format was Getting There: A Book of Mentors by Gillian Zoe Segal, which features essays from Warren Buffett, Anderson Cooper, Jillian Michaels, Michael Bloomberg, and dozens of other luminaries, each sharing their challenges, obstacles, and lessons learned along the way.

After that, I had to check out Tim Ferriss’s famed bestseller Tribe of Mentors: Short Life Advice from the Best in the World, which, so far, does not disappoint. Ferriss takes a question-based approach to the concept, and it’s interesting to see so many varying perspectives on the same set of thoughtfully chosen questions.

Not all advice is good advice for all people—but the right advice at the right time for the right person can be life-altering.

Brief Candle In The Dark

As a long-time admirer of biologist Richard Dawkins, I thoroughly enjoyed his autobiography, Brief Candle in the Dark: My Life in Science. The book is structured as a series of stories and anecdotes, ordered by subject matter rather than chronology. It was fascinating to take a peak behind the curtain and get to know the man behind the science.

After reading several of Dawkins’s previous books, Brief Candle in the Dark offers context about how they fit into the bigger picture of his life and career. It also provides a rather candid look at his experiences, inspirations, and personal philosophies surrounding science, religion, education, the public debate format, and many other topics.

Dawkins is clearly one of the great minds of his generation, but what I think truly sets him apart is his ability to communicate scientific ideas to the general public with excitement and eloquence, instilling in millions a sense of intellectual curiosity.

If you’re a fan as well, you don’t want to miss this book.

My New Favorite Way To Read

When it comes to books, I often bounce between audiobooks and ebooks (I rarely read physical books these days). Audiobooks are great when I’m out and about and looking for passive consumption, whereas ebooks feel more appropriate when I’m sitting down and focusing on reading.

A few days ago, something compelled me to combine the two. I opened up a book in iBooks, started playing its audio counterpart in Audible, and in that moment I knew I’d just discovered my favorite way to read.

With the text in front of me and the narration chugging along (at 2x speed), I’m forced to keep up. And because I’m consuming the content in two different formats simultaneously, I’ve noticed a marked boost in comprehension—even with the increased pace.

So far, this seems like a great way to read more efficiently and attentively. I recommend giving it a try!


In 2007, Gawker published a short blog post outing billionaire and PayPal co-founder Peter Thiel as gay, unknowingly triggering one of the most elaborate conspiracies in recent history: a ten-year, meticulously planned secret effort that ended in a $140 million judgment against Gawker and ultimately, its bankruptcy and demise.

The case that destroyed Gawker was Hulk Hogan’s lawsuit for publishing portions of a sex tape that had been recorded and released without his consent. What Gawker didn’t know during the proceedings was that the case was being bankrolled and assisted in the shadows by an unnamed billionaire—Peter Thiel—so they never stood a chance.

Why Hulk Hogan? It seems the Fourth Amendment argument was an opportunity Thiel couldn’t pass up—though he was also attacking from multiple other angles to solve what he called the “Gawker Problem.”

I really enjoyed Ryan Holiday’s Conspiracy, which tells the full story in detail, informed by interviews with all of the key players, along with historical context and anecdotes about conspiracies as a whole. Real conspiracies—not the Alex Jones kind.

Whether you feel it was a petty act of vengeance or a philanthropic takedown of a toxic media outlet, Thiel’s plot to bring Gawker to its knees was ruthless, cunning, and nothing short of brilliant—and Ryan Holiday’s account of the story does not disappoint. Well worth a read if you’re interested in the Gawker story in particular, or wildly ambitious conspiracies in general.

When Breath Becomes Air

I’m deeply moved by Dr. Paul Kalanithi’s When Breath Becomes Air, a posthumously-published memoir describing the author’s quest for meaning in the face of his impending death.

Paul, an ambitious neurosurgeon, lost his hard-earned career trajectory to a diagnosis of stage IV lung cancer. After years of counseling terminally ill patients through their final days, preparing them to die, he suddenly found himself in their shoes. He now had to prepare himself to die.

In his eloquent prose, Paul explores his experience on both sides of the patient-physician relationship, grappling with questions of meaning, purpose, and direction. By the end, he had addressed not only what it means to die, but what it means to live. On his pursuit of medicine, he writes:

Don’t think I ever spent a minute of any day wondering why I did this work, or whether it was worth it. The call to protect life—and not merely life but another’s identity; it is perhaps not too much to say another’s soul—was obvious in its sacredness. Before operating on a patient’s brain, I realized, I must first understand his mind: his identity, his values, what makes his life worth living, and what devastation makes it reasonable to let that life end. The cost of my dedication to succeed was high, and the ineluctable failures brought me nearly unbearable guilt. Those burdens are what make medicine holy and wholly impossible: in taking up another’s cross, one must sometimes get crushed by the weight.

Death is a reality for all of us. We know this, but in our youth and in our health it often feels like a foreign, distant entity, looming just far enough over the horizon to be of little concern. As Paul writes, there’s a subtle but important difference between knowing you will die and knowing you will die soon:

I began to realize that coming in such close contact with my own mortality had changed both nothing and everything. Before my cancer was diagnosed, I knew that someday I would die, but I didn’t know when. After the diagnosis, I knew that someday I would die, but I didn’t know when. But now I knew it acutely. The problem wasn’t really a scientific one. The fact of death is unsettling. Yet there is no other way to live.

After the diagnosis, Paul faced the notorious dilemma of what to do with his remaining time, shackled by a series of unpromised tomorrows:

Grand illnesses are supposed to be life-clarifying. Instead, I knew I was going to die—but I’d known that before. My state of knowledge was the same, but my ability to make lunch plans had been shot to hell. The way forward would seem obvious, if only I knew how many months or years I had left. Tell me three months, I’d spend time with family. Tell me one year, I’d write a book. Give me ten years, I’d get back to treating diseases. The truth that you live one day at a time didn’t help: What was I supposed to do with that day?

The book ends rather abruptly; as Paul’s wife Lucy notes in the epilogue, he died before he could finish the manuscript. But I wonder if there could have been any better place to close than this final paragraph, addressed to his then-eight-month-old daughter:

When you come to one of the many moments in life when you must give an account of yourself, provide a ledger of what you have been, and done, and meant to the world, do not, I pray, discount that you filled a dying man’s days with a sated joy, a joy unknown to me in all my prior years, a joy that does not hunger for more and more, but rests, satisfied. In this time, right now, that is an enormous thing.

Paul Kalanithi’s life was cut tragically short, but his legacy will endure through this book, one final occasion to do precisely what he spent his career doing: helping people to cope with illness and mortality, find meaning in troubled times, and live and die with grace and integrity.

Reading In The Digital Age

When I was younger, I loved libraries and bookstores. So many books, so many fellow book lovers, and the wonderful, nostalgic scent of ink printed on dead trees (you know the one I’m talking about!). It was great.

Today, visiting a library or bookstore is a rare event—and the end feels imminent. When you have a portal containing the entirety of human literature in your pocket, libraries—and indeed, printed books themselves—obsolesce.

I have an entire library of books on my iPhone. Wherever I go, I always have something to read. And while I’m sad that libraries and physical bookstores will one day vanish, I’m equally grateful for the portability and ease-of-access that ebooks bring to the table. I can’t carry hundreds of paperbacks in my pants.

Not Giving A Fuck

The basic premise of Mark Manson’s The Subtle Art of Not Giving a Fuck:

Look, this is how it works. You’re going to die one day. I know that’s kind of obvious, but I just wanted to remind you in case you’d forgotten. You and everyone you know are going to be dead soon. And in the short amount of time between here and there, you have a limited amount of fucks to give. Very few, in fact. And if you go around giving a fuck about everything and everyone without conscious thought or choice—well, then you’re going to get fucked.

Very much worth a read.

Nothing To Envy

Just finished Barbara Demick’s Nothing to Envy, and I can’t recommend it enough. It’s a fascinating but heartbreaking look into daily life in North Korea, the world’s most secluded regime. It follows the stories of six individuals, humanizing the people who have fallen victim to the Kims’ cruel and totalitarian leadership.

The Key Difference That Makes One Startup Successful While Thousands Of Others Fail

It’s no secret that the vast majority of startups fail. But what’s so special about the precious few that succeed? What makes them gain so much traction and scale so quickly while other entrepreneurs just spin their wheels and ultimately fail?

On our Submit Your Startup page on VentureBreak, one of our tips for getting noticed is to “be a purple cow.” This links to Seth Godin’s book, Purple Cow: Transform Your Business By Being Remarkable—a must-read for entrepreneurs.

I could stop here and just tell you to read the book, but a few people have asked for clarification, so I’d like to explain why I think it’s so important to “be a purple cow.”

I get hundreds of emails a week from entrepreneurs who want me to write about their startups. After a few years of doing what I do, you start to see the same things over and over again. Things that were once interesting start to become background noise because everyone is doing it.

The startups that I actually find interesting enough to write about are those that a) do something radically different than anything I’ve seen before, or b) tell an interesting story that I’ve never heard before. Bonus points if they do both.

The same thought process takes place regardless of whether you’re looking for press, investors, or customers.

Seth Godin articulates it quite well:

When my family and I were driving through France a few years ago, we were enchanted by the hundreds of storybook cows grazing on picturesque pastures right next to the highway. For dozens of kilometers, we all gazed out the window, marveling about how beautiful everything was.

Then within twenty minutes, we started ignoring the cows. The new cows were just like the old cows, and what once was amazing was now common. Worse than common. It was boring.

Cows, after you’ve seen them for a while, are boring. They may be perfect cows, attractive cows, cows with great personalities, cows lit by beautiful light, but they’re still boring.

A Purple Cow, though. Now that would be interesting. (For a while.)

You can apply any number of analogies to this concept, but the point is that you have to be different. Don’t be just another cow grazing on the pasture. Be a purple cow.

You can get a copy of Purple Cow by Seth Godin here.