For Dave Jilk and Brad Feld, philosophy mirrors business

Dave Jilk is a former serial entrepreneur and startup CEO in information technology. He is author of several peer-reviewed papers on artificial intelligence as well as two books of poems, “Distilled Moments” (2020) and “Rejuvenilia” (2018). Dave earned his bachelor of science degree in computer science from the Massachusetts Institute of Technology, and currently lives near Boulder, Colorado. When not writing he is likely to be on a mountain somewhere.
Brad Feld, co-founder of Foundry Group and Techstars, has been an early stage investor and entrepreneur since 1987. Brad is a writer and speaker on the topics of venture capital investing and entrepreneurship. He holds degrees in management science from the Massachusetts Institute of Technology. He also enjoys collecting art and long-distance running, and has completed 25 marathons as part of his mission to finish a marathon in each of the 50 U.S. states.

SunLit: Tell us this book’s backstory. What inspired you to write it? Where did the story/theme originate?

Jilk and Feld: A crucial part of the backstory is the way-back-story. The two of us were college friends, then business partners, then colleagues in a variety of efforts, and have remained friends throughout the past forty years. Having worked together for a long time, each of us understands the other’s business thinking and work process quite well.

Dave reads a lot of philosophy, and around 2010 had just started reading some Nietzsche. He began to notice an occasional quip or line that rang a bell, seeming to describe entrepreneurs. At one point, we were both up at Brad’s mountain house reading by the fire, and Dave read one of these lines out loud to Brad, asking whether it resonated. He interrupted his reading, thought about it for a second, and agreed. That was the genesis of what became this book.

After Dave semi-retired (among other reasons, to do more writing) in 2013, we discussed the idea of bringing together some thoughts about entrepreneurship with Nietzsche’s ideas into book form. Brad was always looking for new directions from which to help entrepreneurs, and Dave was looking for a venue in which to encapsulate some of the things he had learned in his career. So we got started, picking off a chapter at a time.

The format evolved as we worked on it. Brad suggested gathering entrepreneur stories to complement the essays, and after we completed a few we saw that these really added value.  We read a lot of Nietzsche, perhaps with a bit of a “quote-picking” agenda. “Test readers” helped us realize that we needed to provide modern versions of the quotes. And we had both read Ryan Holiday’s “The Daily Stoic”; we decided that a similar structure with a weekly pace would be good for the level of depth we were aiming at.

Place this excerpt in context. How does it fit into the book as a whole? Why did you select it?

We selected the chapter “Style” because it illustrates some of our goals with the book particularly well. Most notably, in his narrative Tim Enwall shows his own thought process as he considers the Nietzsche quote and our essay, and how those conflict with his own view of things. By the end, he has not so much changed his mind as deepened his thinking about issues around the connection between brand image and company culture.

In the Introduction we encourage all readers to give this level of thought to each quote and essay that they approach – not to just read-and-implement, but to chew on it for a week or so, and ideally to discuss it with others in the organization. There are some great how-to books on entrepreneurship; ours does not try to be one of those. Instead it aims to help entrepreneurs think more deeply about themselves and their business.

Another important aspect illustrated by this chapter is the surprising interpretation that connects Nietzsche’s thinking to today’s world of entrepreneurship. In the quote, he was talking about actual artistic style in a national context. But it derives from his insights into human nature, not just the particular situation. We find that these unusual applications can help a reader – and us – think about organizational and leadership issues in a completely different way. We’re not making any strong claims about what Nietzsche intended – if our book is philosophy at all, it is very much applied philosophy in an entrepreneurial problem domain.

Structurally, the excerpt is one of the 52 “weekly” chapters. Most of them are structured similarly, though not all of them include an entrepreneur narrative. The chapters are organized into five major sections around a theme – this one is part of “Culture.” The other sections are “Strategy,” “Leadership,” “Tactics,” and, wait for it… “Free Spirits.” The book also contains an insightful foreword by Reid Hoffman, who really took the time to understand what we were trying to accomplish, and a couple of appendices about Nietzsche for readers who are interested in learning more about him and his legacy.

Tell us about creating this book. What influences and/or experiences informed the project before you actually sat down to write the book? 

When we were in business together in the late 1980s and early 1990s, we would periodically read a book together and then discuss it; as our business grew we’d include the entire team in these exercises. Some of these were business books, but others were not. For example, one was “Jonathan Livingston Seagull,” by Richard Bach.

We gained two really important lessons from doing this: first, gaining even a single good idea that could be applied in the business made the effort worthwhile. Second, the process of thinking through and discussing ideas about business, in the context of our own business situation, was not merely practical but also inspiring. This was particularly noticeable when we were struggling: the realization that startups are hard, that we were not the only ones fighting various issues, that what entrepreneurs do is good and important, and so forth, all gave us new energy to carry on and improve.

So when we set out to write the book, we wanted to make sure that our readers were both inspired and pushed to think harder. The particular ideas we touch on are all relevant areas to every entrepreneur. Whether the perspective captured by Nietzsche’s quote, or by our essay, or by the entrepreneur narrative is actually directly useful is almost beside the point. We’d actually be happier if a reader decides that what we say is completely wrong for her business, and does the opposite with great success. That means we helped her think, which is our real goal.

Here we offer a portfolio of 52 different topics to think about. We feel good about the likelihood that for every reader, at least one of the chapters will produce a valuable takeaway.

Once you began writing, did the story take you in any unexpected directions? If so, how would you describe dealing with a narrative that seems to have a mind of its own?

Almost every chapter was like this to some degree. The point of the book is to think, so as part of writing a chapter we would sit with the quote numerous times and reflect on it. Frequently we came up with new angles that weren’t part of the initial impetus for selecting it. That was really fun. The entrepreneur narratives were sometimes even further afield. A few of them barely connect with our essay at all. But taken as a whole, each chapter represents a thinking process, a set of reflections on a topic area. Thinking is not always linear; the best thinking, especially when you are stuck, is not merely “non-linear” or “outside the box” – it’s not even a geometric shape. 

For a more specific example, toward the end of the writing process we realized that we were using the words “passion” and “obsession” somewhat interchangeably, in part because Nietzsche uses the word “passion” regularly. But Brad has written and spoken a good deal about this: As an investor, he is looking for obsessed entrepreneurs, not passionate ones.

And then we had an epiphany – in our chapter entitled “Obsession,” the Nietzsche quote shows him trying to describe the concept of obsession, but using the word “passion.” A little more research showed that the notion of obsession was not in common use until later. In a sense, Nietzsche had made the same discovery and observation that Brad had, but 140 or so years earlier and without the terminology to say it: The two are not the same, and passion has some serious shortcomings.

Has the book raised questions or provoked strong opinions among your readers? How did you address them?

Early on, we noticed that some people had strong feelings about Nietzsche: some positive because they had read and enjoyed him in college or otherwise, and others very negative because of a certain “reputation” Nietzsche has. The latter issues go all the way back to his proto-fascist, anti-Semitic sister Elizabeth, who was his final guardian after his mental collapse and controlled his literary estate after his death.

But these issues continue to this day, in part because Nietzsche made a lot of strong statements that could be interpreted any number of ways, including ironically. His words have long been used to justify a variety of positions ranging from Marxism to the alt-right, and misinformation abounds.

We decided we needed to address this in the book, first to ensure that our efforts were not associated with any of those agendas, and also to review, for readers unfamiliar with Nietzsche, why he is probably nothing like what they’ve heard about him, whatever that might be. Thus we include in an appendix a moderately scholarly effort to explain why this has happened, and why the reader should not be too concerned about it.

There were two things we had to admit, though. We, too, had used Nietzsche’s words in ways he had not intended. We decided that was acceptable since we are very transparent about it in the introduction and throughout the book. We also admitted that one thing people have heard about Nietzsche is verifiably true: He can be difficult to read. This we addressed by limiting ourselves to fairly straightforward quotes and also by adapting them to 21st-century English.

We identified one other obstacle to drawing our audience of entrepreneurs to the book. The link between entrepreneurship and philosophy is not obvious – one endeavor is very action-oriented, the other more pensive. Anyone who has read late 20th-century philosophy might find it pedantic (if they are reading analytic philosophy) or impenetrable (if it is continental philosophy).

We discuss this issue in the Introduction, but Reid Hoffman’s foreword is where the connection really comes alive. You can read it in the Amazon free sample or on Reid’s website. Once entrepreneurs dig into the book, they find that elements of Nietzsche do speak to them, just as they did to us when we first read it. This allows them to go deep quickly.

Beyond enjoying and getting value out of our book, we hope that this will encourage them to find other philosophers they find helpful, whether it be Stoics like Marcus Aurelius, ancient Greeks like Epicurus, an existentialist like Simone de Beauvoir, or a modern virtue ethicist like Martha Nussbaum.

Walk us through your writing process: Where and how do you write?

Most interesting is how we write together. We have incompatible schedules, not only on a daily basis but on an annual cycle. Brad writes quickly and then edits; Dave labors over a paragraph until he is happy with it. We have metaphysical conflict regarding comma usage. Google Docs made it all work. We used both suggesting mode and commenting to interact on the chapters until we were both comfortable with the content as well as the language. We also used it to integrate text from entrepreneurs and chapters that had been done on the side. At the end, we used Grammarly to reduce passive voice and other linguistic crutches.

It’s worth noting that with the schedule issues and other distractions, it took five years from beginning to end to get the book done. OK, so maybe it wasn’t just Google Docs; perhaps it’s that we’ve been friends and colleagues for almost 40 years, and know how to work and persist together.

If a reader of your book wanted to explore Nietzsche directly, what would you recommend?

It depends on how much fortitude you feel. If you are feeling confident, pick up “Human, All-Too-Human.” This is the first of three books written in an aphoristic style – sections range in length from a single sentence to a few pages. It covers a wide swath of Nietzsche’s philosophy, and much of it is very readable.

If you don’t understand a section, or find it uninteresting, just skip it. These books are not really cumulative: You can jump around or even read them backward (as with our book… coincidence?). That book is great bathroom or waiting-room reading. But take your time with it. Beneath what might appear to be outrageous or snarky comments is a lot of depth.

If you prefer to ease into it, pick up a recent secondary source like Eric Steinhart’s “On Nietzsche.” This is a solid overview. Not everyone would agree with his interpretations, but that’s true of any definitive interpretation of Nietzsche. Recent books like “I Am Dynamite” (Sue Prideaux) and “Hiking with Nietzsche” (John Kaag) also give some insight into the philosophy while being mostly biographical.

If you are feeling unconquerable and want to “leap into their jaws,” try “The Genealogy of Morals” or “Beyond Good and Evil.” These are among his later works and tell a more complete story about their subject area. They probably represent the most culturally influential elements of Nietzsche’s philosophy, treating ethics as arising out of cultural evolution rather than from God or from irrefutable axioms.

Unless you were a literature major with very good grades in college, we’d recommend against starting with “Thus Spoke Zarathustra,” even though it’s possibly his most famous book. The layers of allusion and irony, and the absence of much plot, make this a very difficult book.

Are you going to follow this up with another book based on another philosopher, or on some other source of quotations?

A number of people have asked this. The answer is probably not. If you read the book, you will get the hang of it – reading a colorful line from any source can inspire some deep thought and insights. Though we hold forth on entrepreneurship in this book, we’re not looking to do more of that, and it was not the underlying goal even here.

We’re also not looking to create a brand around Nietzsche. Though we have nothing against monetization, Nietzschean motivations like gratitude and working on this together as the “reward of all rewards” are more what drove us.

For his next book, Dave is working on a science-fiction epic, but sharing any details here would be spoilers.

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