Zen, Motorcycles, and the Art of the Startup

Jeff Bussgang
4 min readOct 19, 2020
The Classic Pink cover that I remember from when I was a teenager

Over the last few weeks, I was inspired to re-read Zen and The Art of Motorcycle Maintenance, a book I read in my late teens and remember enjoying.

At the time, I embraced its emphasis on Quality (hard to define, easy to discern) as an organizing mantra for living a purposeful life. The book was published in the 1970s at a time when many young people were waking up from the hangover of the 1960s and feeling aimless and unfocused. What was the meaning of life and how should a good life be lived? Author Robert Pirsig does a brilliant job trying to address these big questions with a ranging review of Buddhism, Socrates, Plato, Kant, and other philosophers all told through the prism of an autobiographical journey on a motorcycle through the great expanse of the West with his young son. It has since become the best-selling philosophy book of all time.

Reading Zen decades later, though, gave me a new perspective on the book and its lessons for the art of startup building. Pirsig spends time highlighting the limitations of the scientific method and those limitations are ones that I’ve been thinking about recently in the context of startups.

The scientific method is a process for experimentation that rests on the belief that hypotheses should be sharply defined and then rigorously tested through well-constructed experiments. Eric Ries popularized applying the scientific method to startups through his book, The Lean Startup.

At Harvard Business School (HBS), in both my class and the entrepreneurship department more broadly, we teach the importance of treating startups like experimentation machines. But HBS and other entrepreneurship programs and startup accelerators typically fall short when giving guidance as to how to determine which experiments to run. I have written in the past that for founders, test selection is all about strategic choices.

Entrepreneurs need to be thoughtful and disciplined regarding test selection, design, and prioritization. In short, entrepreneurs need to analyze their business model critically and select the tests that matter the most at each phase of their journey.

What is less well-understood is the process for determining which experiments to run and how to sequence those experiments. Given that founders have a discrete envelope of time and money before they need to produce positive results, experimentation selection is one of the most critical factors in startup success.

Pirsig speaks to this point in a more general sense. Written in the 1970s, Zen could not have anticipated the impact of his words on tech startups. But his argument applies beautifully to tech startups when he states that test selection must come from intuition. At one point late in the book he observes:

“You need some ideas, some hypotheses. Traditional scientific method, unfortunately, has never quite gotten around to say exactly where to pick up more of these hypotheses…Creativity, originality, inventiveness, intuition, imagination…are completely outside its domain.”

The problem for entrepreneurs, then, is how to build up this intuition. How should an entrepreneur best navigate the Idea Maze (a lovely metaphor from Chris Dixon)?

As with the elusive definition of Quality in Zen, the answer is subtle and not easy to deliver or communicate. We think we know how to identify a quality entrepreneur, a quality business plan, a quality consumer value proposition, a quality initial product, and a quality go to market plan. But is there a rule set that entrepreneurs can follow to know that they are on the right path? The sad answer is no. But founders can do a few things to help in developing that critical entrepreneurial intuition required to navigate the Idea Maze:

  1. Customer Development. Immerse yourself in the customer problem set (i.e., perform deep customer development in the classically defined manner of Steve Blank and Four Steps to the Epiphany) to develop an intuition on the customer’s pain points to hypothesize compelling value propositions.
  2. Domain Knowledge. Study the domain through both direct research (i.e., be an autodidact founder, defying the myth of Founder-Market Fit) and by surrounding yourself with domain experts to develop an intuition on the market dynamics and trends.
  3. Strategy 101. Apply rigorous strategic thinking to the market dynamics, the value chain, substitutes and complements to develop an intuition on where profit pools may lie.
  4. Built a Test Machine. Build an organization that is able to run tests rapidly and efficiently so that your testing throughput is faster than your competitors, building a startup organization that is a learning machine as well as an execution machine.

Follow these steps and, hopefully, you will find your path to Quality experiments, execution, and company-building.

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Jeff Bussgang

Former entrepreneur turned VC @Flybridge, teach @HBS, author of Entering StartUpLand and Mastering the VC Game