Excerpt from”Moral Letters to Lucilius/Letter 59″

From Moral Letters to Lucilius/Letter 59:

“The wise man is joyful, happy and calm, unshaken, he lives on a plane with the gods.  Now go, question yourself; if you are never downcast, if your mind is not harassed by my apprehension, through anticipation of what is to come, if day and night your soul keeps on its even and unswerving course, upright and content with itself, then you have attained to the greatest good that mortals can possess.  If, however, you seek pleasures of all kinds in all directions, you must know that you are as far short of wisdom as you are short of joy.  Joy is the goal which you desire to reach, but you are wandering from the path, if you expect to reach your goal while you are in the midst of riches and official titles, – in other words, if you seek joy in the midst of cares, these objects for which you strive so eagerly, as if they would give you happiness and pleasure, are merely causes of grief.”



Inspiration or Innovation

Time is a teacher. With age, fundamental shifts in my perspective have emerged that I neither anticipate nor ask for and that, ultimately, highlight how little I know about much of anything. Examples abound, but one such shift took place while viewing a 2005 Bezos recording about “taking on the challenge” of entrepreneurship.

We’re hopefully in agreement that Bezos is one of the greatest businesspeople in recent memory and, even in February 2005 — when Amazon was priced at roughly $35/share (you do the math) — it’s apparent that he excels at something so common among the brilliant: namely, making complex ideas accessible to the layman.

His resonating point concerns how people approach the generation of new ideas. To many, myself included, the easiest way to frame or define idea generation is by attributing a new thought or concept to inspiration — the proverbial “light bulb” going off. We all have ideas, and chalking this up to some random inspiration multiplier that functions slightly differently from one person to the next makes it easier to rationalize that some will inevitably have better ideas than others.

Bezos describes this as people seeing a problem that annoys them, which then motivates them to find a solution; inspiration strikes to offer solutions to the annoyance. For as long as humans have been conscious enough to be annoyed, these moments of inspiration have spawned the creation of tools, technology, art, acts of charity, WD-40 and so on. But far more frequently, inspiration yields little more than a moment of self-congratulation and a passing “I should write that down” which we quickly forget once we’re confronted with the menu at Starbucks.

How Bezos continues is what struck me:

Sometimes you can work this from the backwards direction and, in fact, in high-tech I think a lot of the innovation sometimes comes from this direction. You see a new technology or there’s something out there, some new understanding in the world, and you work backwards from a solution to find the appropriate problem.

The process that Bezos identifies is the opposite of inspiration. He points to the conscientious and active channeling of brainpower to identify an annoyance before it strikes — in my mind, innovation. Where inspiration is fleeting and self-indulgent, innovation is pointed and educated. Understanding a market takes time, particularly from the outside looking in. To further bet on this market by inventing and investing in solutions to problems or annoyances that have not yet emerged: that’s vision, that’s insight, that’s innovation.

It takes but a few moments to connect the dots between recently notable founders and markets they upended through conscious and calculated innovation. Daniel wasn’t a record producer, Brian didn’t run hotels, the Jennifers weren’t dry cleaner franchisees. In each case, the market silently screamed for attention and they tuned in to the frequency before anybody else cared to actively listen.

Why so personally pivotal? Because it’s easiest to explain the success of our innovators by attributing it to a moment of inspiration that the divine weren’t kind enough to impart upon us personally. It acts as both an excuse — “well, the idea didn’t come to me” — and an exemption — “…so I didn’t do the work”. A naive avoidance of giving credit where credit is clearly due which also serves as a method for conveniently excluding ourselves from the ranks of the exceptional.

As a person who closely guards the idea journaling habit, this perspective gave me pause. The “billion dollar partnerships” formed over a few pints, the woodshed inventors that tinker for a lifetime, the silent genius that keeps her ideas hidden from the world are legion. While I doubt it was his intention, in just a few sentences Bezos sent a chilling message: maybe the majority of our most successful doers find themselves there because it was their exact intention. The partners wrote the business plan, the invention left the woodshed, the silent genius chose not to keep silent.

Waiting for the mythical “right idea” is just that, a myth. An individual with an authentic passion to change the way we humans interact with our world, despite best intentions, may wait on inspiration for a lifetime. But the hard-won progress of innovation, that’s available to us whenever we’re ready to hunker down and do the work.

Inspiration or Innovation

Success = failure

If we have a true authentic purpose, and remove ego from the equation, is there any difference between success and failure? Can we not be ambivalent about making the money, getting the recognition, securing the legacy if we are in the pursuit of something real?

Endeavoring to make the world a safer, friendlier, more sustainable place presents us with an interesting goal: the goal of impact. The goal to motivate and act as a catalyst for some kind of change. If we fail in this endeavor, the loss is not money / recognition / legacy…it’s a of loss impact. The change doesn’t happen.

But if we were truthful in our pursuit, in our purpose, then failure is a hiccup. Similarly, unless we plan to bask in our greatness, success offers a comparably brief respite.

There’s really no time to dive in failure’s pools of sorrow or to linger in the throne of praise presented by success. Unless the plan is to be consumed by our ego and to preserve the narrative structure of our success story (“I’m a genius”) or failure story (“I’m an idiot”), it’s right back to purpose. Right back to the authentic cause that keeps our spirits roiling and our eyes from shutting at night.

It’s worth considering if there’s any difference at all between success and failure if our plan and purpose is clear. Either sequence of events seems capable of expediting our demise if ego takes control.

Success = failure

What Billionaires Read

Picking a new book for our reading group often feels like a Sophie’s Choice of sorts. We’re overcome with joy to jump into something new, and consumed by sorrow that we can’t read everything.

…So it comes as no surprise that our reading wish-lists have ballooned to grotesque lengths. To add insult to injury, we consistently discover reading lists of other mentors / achievers / thinkers that we feel inclined to attach to our own.

One such list was recently published which collects all of Marc Andreessen’s tweet-endorsed reads. We’re big fans of his colleague Ben Horowitz’s Hard Part About Hard Things — turns out so is Marc — but otherwise this list is fresh territory for the DMR crew.

Topics span business, politics, history, finance, art, fiction, and more.  Happy reading.

Andreessen’s Favorite Books


What Billionaires Read

Hustle Con 2016 – Takeaways


Hustle Con is the anti TechCrunch Disrupt.  It’s not about crushing code in a dark room while you slurp down cup-0-noodles.  (Okay, maybe there are cup-o-noodles involved.)  Instead, it’s a conference designed for non-technical founders that are striving to build physical world businesses.  These are hungry entrepreneurs in the worlds of fashion, food, furniture, and beyond…all coming together in a 1-day sprint to learn from the best.  And go figure, there are actually a few entrepreneurs who built / are building massively successful business without using Sublime Text.

You can check out the full guest list for Hustle Con 2016 here, or just dive right into the recordings on their YouTube page.  In the meantime, here are my notes and three key takeaways that have kept me up for the last few weeks:


You are the guardians of simplicity in your organization.

David Bladow, BloomThat

Successful entrepreneurs build their businesses around one core idea, only expanding once they’ve validated a simple concept that appeals to an identifiable market.  New ventures can so easily spin out of control as founders attempt to pack on new products, designs, pitches, etc…but scaleability cannot be reached through complication.  If you think focus is challenging as a small company, the conditions only get more worse as you grow.


The evolution of mankind, starting with pants.

Andy Dunn, Bonobos

Even if your soon-to-be unicorn company is still an organization of one, have a mission.  A one sentence, no frills statement that characterizes your business and all it hopes to accomplish, that explains the “why”.  This is important not just for you, not just for maintaining focus (see takeaway 1), but also for attracting purpose-driven people as you scale.  For an entrepreneur, not having a sense of mission is crippling.  For a team, it’s fatal.


We set out because we believed in something…there’s no fear, nothing to lose when you’re passionate about something.

Andy Puddicombe, Headspace

Authenticity is a secret weapon of all successful entrepreneurs.  While it’s intoxicating to believe that a great idea can sustain you through the inevitable trials of an entrepreneurial venture, it’s a falsehood.  Without an authentic purpose, without a true meaning and momentum behind your venture, you’ll find that you’re faking it, that you’re operating without real passion.  And without passion, no success can there be.  Yoda said that, right?

Hustle Con 2016 – Takeaways

Quote 5.11.16

Let the soul be roused from its sleep and be prodded, and let it be reminded that nature has prescribed very little for us. No man is born rich. Every man, when he first sees light, is commanded to be content with milk and rags. Such is our beginning, and yet kingdoms are all too small for us.

-Seneca, Letter 20


RIP Wolf


I didn’t come to know Jim Harrison like so many around the release — literary or theatrical — of Legends of the Fall, the epic drama of the American west that ushered the author into his greatest period of financial success and critical acknowledgement.  In fact, it was an episode of No Reservations with Anthony Bourdain — a terrific author in his own right —  that introduced me to this callous American storyteller.

Bourdain’s interview encouraged me to pick up Wolf, Harrison’s (supposedly) semi-autobiographical book about a young man wandering America in search of his identity (and sex).  Once completed, I proceeded to devour everything else he’d published.  His prose reminded me of a soft-spoken Cormac McCarthy, with a layer of compassion and wonder for the natural world.  His stories are haunting and visceral, but somehow keep the reader in awe of the small beauties that impart all the meaning to our lives.

I suppose I’ve been drawn to Harrison not only for the quality of his writing, but also for his unapologetic hunger for life.  Few have the courage to live with the relish that Harrison did over the course of his 79 years.  Beyond his reputation as a poet, essayist, and author, Harrison was also an avid gourmand and enjoyer of the finer tastes that life has to offer (check out his memoir The Raw and the Cooked for more on this facet of his life).  Margalit Fox of The New York Times cleverly summarized the pursuits that defined his life in a series of monosyllabic words: walk, drive, hunt, fish, cook, drink, smoke, write.  Could there be anything more pastoral, idyllic, and wildly inviting than a life lived to pursue these tasks?

Harrison leaves this world having had a permanent impact on my life, but also, and far more importantly, on the landscape of American literature.    He was an insatiable man in every sense, and I hope I’ll have learned to live just a bit more bravely and authentically having read his words.

RIP Wolf

Mindful Ambition

One of the more popular topics of discussion in our reading group is how to balance ambitious goals with a strong desire to remain mindful, humble, and grateful.  At times, these two priorities can feel like oil and water and the group reading we’ve completed has yet to reveal the “silver bullet” solution that harmonizes powerful self-motivation with a balanced state of mind.

mindful ambition, the practice of maintaining awareness, humility, and gratitude in the pursuit of extraordinary accomplishment

Last week, I took a stab at providing some answers to an audience of colleagues.  “Being Mindful While Making It Rain” introduces the concept of mindful ambition: the practice of maintaining awareness, humility, and gratitude in the pursuit of extraordinary accomplishment.

We cover five different elements of our lives that demand attention if we hope to pursue great accomplishment without sacrificing the energizing and grounding impact of a present mind.  I also throw in five corresponding activities that can be used to introduce mindful ambition in more concrete terms: taking a success inventory, keeping a gratitude journal, reconnecting with nature, plotting your wealth columns, and (most importantly) initiating a meditation practice.

Check out the video below and download the deck so you can follow along.

Please note, the video is cut a few minutes short.  Everything you missed — including helpful book and app resources — can be found in the deck PDF (link above).


Chamath at LAUNCH

Chamath Palihapitiya is a beast.  He’s most notably a key member of the executive team that brought Facebook over the 1B user mark.  More recently, he’s been running The Social+Capital Partnership and acting as part-owner and board member for the Golden State Warriors (you know, the NBA team with six losses after 62 games).

He also brings the heat anytime he speaks publicly, and was by far my favorite speaker at this year’s LAUNCH Festival.  Topics covered include sports, politics, morality, gambling, tech, and beyond…but Chamath’s comments on diversity in tech and the dusty, overly white hierarchy of venture capital steal the show.

He’s an influencer worth following and definitely one that will get you thinking about the big things.


Radio Headspace Is A Thing


Each member of the DMR team incorporates a meditation practice into their daily routine.  The return on investment for just 10-15 minutes is too good to pass up, and Headspace is one of the apps that has made this habit a very easy add.

As a major podcast fanboy — Tim Ferriss, a16z, TWIST, etc. — I was blindsided when I discovered that the Headspace team is 50+ episodes into Radio Headspace, a podcast covering anything and everything related to our mental capacity and the journey within.

One of the latest episodes — #54 — brings in three different authors that have been commissioned to write books for The School of Life, an amazing project created by one of the group’s favorite authors, Alain de Botton.

I’m overwhelmed by this nexus of amazing people and projects…and while I can’t yet speak to the overall quality of Radio Headspace, I certainly intend to check it out.

You should too.

Radio Headspace Is A Thing