On the Nature of Work and Derrill Osborn

I had lunch with an old friend/former colleague last week. We took awhile to catch up on life before we realized that something rare and special had happened to both of us. During the years we worked together, we enjoyed some of the best work time that either of us had experienced in our careers. Don’t get me wrong. Every day wasn’t a love fest and there were times when we just didn’t get along. This “rare experience” that we shared was an aligning of these stars:

A lot of the time, we were doing our very best work together. I mean, great output. Stuff that adds real value and helps the company grow.

And while we were doing that, at least some of the time, we were having pure fun at work. Laughing so hard we were crying and not able to hold it together. But still while working pretty damn hard.

And most of the time while all that was happening, we were genuinely enjoying the people we were working with. True talent. People who loved what they were doing and were intent on constantly improving the level of their work in a friendly competitive environment.

So, we were doing our best work, pushing hard with talented colleagues, and having exuberant times of fun with each other while we worked our asses off.

That trifecta is too rare in a career. It does not happen by accident. The conditions have to be nurtured. Above all, there needs to be an orchestrator. A magnetic force must be present to draw the necessary components together.

This finally brings me to the chief topic here. For the last few summers, I can’t get through a July without ruminating about Derrill Radcliff Osborn. The late, and very great, DRO. Derrill was a legendary merchant, an eccentric person of the highest order who was a menswear industry icon in the 80’s and 90’s, best known for his long run as the chief tailored clothing merchant at Neiman Marcus. Derrill died on July 1, 2019 at the too-young age of nearly 77. Later that month, he was celebrated in a one-of-a-kind memorial service at Highland Park Presbyterian in Dallas that honored his life and brought his giant personality into that lovely church. Always a stickler for details, before he checked out, he specified the dress code for his own service and left instructions that his ashes were to be “flushed down the commode.” Walking out of the church that day, I perfectly understood the scalability of Derrill’s personal touch. From his corner of the world, he affected multitudes, one by one.

And while his merchant genius was well-recognized, I submit that Derrill was, above all, a virtuoso orchestrator. He always seemed to bring an immaculately-groomed collection of talented people together, prodded them to do their best work, and all the while made doing the work fun. With Derrill, humor entered every interaction, taste and culture ruled above all, curiosity led to the next adventure, and excellence was the baseline expectation. Those who knew Derrill will not simply never forget him, they will always feel the impression he made. While I never worked for Derrill, I worked with him. He was my customer for many years. And if you were in Derrill’s orbit, he put you to work. So in a sense, I did work for Derrill. We all did. No matter how you look at it, I was both witness and subject to his abilities when it came to artfully blending work and life into one.

When Derrill retired, I expected he was going to write his memoirs. But he kept too busy living the next chapter of his life to spend time looking back. At the very least, I hoped that someone would write a book about Derrill, an endlessly fascinating and talented man, self-invented in an image of his own creation. When that book is written, I’ll be first in line for it. Until then, I’ll satisfy myself with memories of a singular personality, a magnetic force, who orchestrated a legendary life.

My All-Time Business Book List

Until fairly recently, I included a list of books as part of my LinkedIn profile. While these were not necessarily my all-time favorite books for sheer reading pleasure (for that I thank Haruki Murakami), these were the business books I found distinctly instructive on matters of strategy, leadership, business building and just plain “how to manage stuff.” There’s no shortage of business books, podcasts, and articles in this world, so my humble purpose in publishing this list was simple: help others sift through a mountain of books to get to the ones that really matter. After all, someone referred these to me and I’d like to pass on that favor. But also, this little collection represented my thinking about business and my approach to work, as I (hopefully) internalized and put into practice the lessons and wisdom within these great books. Well, at least that has been my aspiration.

Earlier this year, I blew up/redid my LinkedIn profile and that book list went poof. In this article, I’m re-listing those books in hopes they can be useful to some of you. In future posts, I may try to provide other highly-edited resources like this, but more along the lines of podcast episodes or articles that, in my mind, truly stand out. For now, here’s the book list. Not sexy, no AI, nothing algorithmic, just some well-written and smart books for learning and enjoyment. Hope you find this helpful…

Small Giants (Bo Burlingame) - successful businesses that challenge the notion of growth for growth’s sake and what makes them tick.

Setting the Table (Danny Meyer) - it’s really two books in one: his origin story and the subsequent development and refinement of his brand of “enlightened hospitality”. A must read for high-touch businesses.

Good to Great (Jim Collins) - this is one you read and re-read and never stop coming back to. It overflows with timeless wisdom. There is never a bad time to read this book.

High Output Management (Andrew Grove) - it’s become a trendy/staple Silicon Valley read but I’m always surprised by how little known it is outside of that sphere. Full of smart and practicable advice by someone (legendary) who actually did it.

No Rules Rules (Erin Meyer, Reed Hastings) - the unorthodox and sometimes contrarian business culture philosophy that built Netflix from the guy who built Netflix.

Creativity Inc. (Ed Catmull, Amy Wallace) - the creative ways that a company whose survival depends on creativity unleashes and harnesses…creativity.

Beyond Entrepreneurship 2.0 (Jim Collins) - more practical wisdom from Jim Collins. So core and fundamental and highly-applicable in any business context.

Working Backwards (Bill Carr, Colin Bryar) - how business is done at Amazon. Every great business has its own way of doing things. Amazon’s ways are highly indoctrinated and well-covered but this book sums it all up and explains how their unique methodologies underpin their culture and fuel their output.

What You Do Is Who You Are (Ben Horowitz) - the title sort of says it all but this book hits the topic of company culture in a fresh and digestible way.

Shoe Dog (Phil Knight) - sometimes it’s just fun to read about how a business went from nothing to something and what it had to slog through to get there. What a story.

The Power of Habit (Charles Duhigg) - I guess you could call this a “self-help book” but it’s one whose lessons apply broadly. Both high-functioning companies and individuals need to be driven by the right habits and there’s a science to how these habits are formed and kept. Maybe sounds dry but it’s engagingly readable and incredibly useful.

Only the Paranoid Survive (Andrew Grove) - the second book on this list by the great man Andrew Grove, it hits on competition and transformation with urgency and intensity.

That’s it. By the way, the above list is in no particular order…