Revisiting the Zen of Entrepreneurship

In Silicon Valley, it’s easy to find lots of advice on what I call the “external” how-tos of startups, including: structuring your company, building a minimum viable product, negotiating a term sheet with investors, selling your company, and on and on!

This post, on the other hand, is about the less publicized “inner side” of the entrepreneurial journey. In this journey, there are no ready made prescriptions. Every company, entrepreneur, and market is unique. Rather, it’s about developing a “clear mind” to see what’s really happening, trusting your “gut” to find a path through uncharted terrain, and recognizing and transcending your personal patterns to find your calling in life.

Do any of these things really help in building a successful startup? When I started my first software company fresh out of MIT, I didn’t think so. Imagine my surprise when, a few years later, the issues I was struggling with in my path of personal growth turned out to be the same issues that would determine life or death for my startup! I wrote my book, Zen Entrepreneurship, which is free this week on amazon kindle here, to share some of the lessons I learned.

Here are some highlights:

1. Stay Calm and See Clearly.

Running a startup can be like having several firehoses aimed at your from different directions, each one trying to knock you off balance. How can you retain a calm mind and not panic with every burst of the unexpected?

Taking a little time away from your startup to develop focus and clarity of mind is an essential practice that I highly recommend. In Eastern traditions (and increasingly in the west), this means meditation or yoga. While these practices provide practical benefits like increased concentration, calm and endurance, the real goal of these practices is something else entirely: awareness.

In the yogic traditions, our mind-body consists of a several clear sheaths (called khosas), and as we experience stress in our lives and our work, we build up imperfections in these sheaths (called samskaras) to the point where they become muddy and don’t let light shine through. Ultimately this blinds us to seeing the results of our actions clearly, and we get caught in repetitive patterns. Unlike exercise, which is primarily a physical activity, meditation and yoga practices helps to clear these sheaths, like cleaning a dirty windshield, which allows us to perceive more clearly what we’re dealing on the road around us, and then take appropriate action.

As entrepreneurs, we are so busy convincing investors, employees, advisors and customers of our vision of the future, sometimes we’re blinded to the underlying reality of the market around us until it’s too late. In Silicon Valley, the blogs are full of reasons why companies and products fail after the fact.

Unlike the famous (fictional) Japanese blind swordsman, Zatoichi, who often saw the results of a particular sword swipe in his mind before he acted, it’s never possible to predict the results of an action completely. It is, however, possible to perceive those results more clearly as soon as they happen, if we’re in the right state of mind. Rather than seeing how we would like a product to perform, we can see what’s really happening in the market — and then take appropriate action.

2. Entrepreneur, Know Thyself! Your Patterns are like Dragons.

If there’s one thing I’ve learned from starting multiple companies and investing in dozens of entrepreneurs, it’s that sooner or later, your personality affects the trajectory of your startup — whether you want it to or not!

In my book Zen Entrepreneurship, my mentor uncovers a pattern in my life that I was only barely consciously aware of at the time: I was always looking for something new and exciting, and would end up doing too many things at once. Eventually, I’d be forced to drop some of the activities I was juggling in order to salvage the rest. To qualify as a pattern, something has to happen at least 3 times, and it had — in high school, in college, and now in my first startup after school.

When we raised VC money for this rapidly growing startup, this pattern got worse, not better! It crystallized into what I now call the “Acting vs. Singing” issue (“In Hollywood, all actors want to be singers, while all singers want to be actors”). Every one of the startups I’ve been involved with since have faced a core issue like this in some form. We couldn’t decide whether we wanted to be a product company or a service company, so we kept doing both, which almost led to disastrous results. To make my company succeed, I had to recognize and deal with this internal pattern that was unconsciously driving my business.

As another example, I know one entrepreneur in Silicon Valley who always finds himself in a similar situation with new investors and advisors. There’s always a honeymoon period when the “new guy” can do no wrong in his eyes and he wastes no time boasting about this to the rest of the team. Sooner or later, one of the decisions they make doesn’t turn out so well. Then the entrepreneur starts to blame the “new guy” entirely for the failure, rather than taking any responsibility himself. Eventually, the new guy gets fed up with the entrepreneur, and they part ways, never wanting to have anything to do with each other ever again.

The remarkable thing about this pattern, which I only recognized after it had happened several times, was that the entrepreneur had no idea this was happening. Like Bill Murray in GroundHog Day, that he was caught in a ever-repeating drama of his own making. Only by consciously recognizing this pattern as a reflection of his own issues, which he was unwilling to do, would he be able to transcend the pattern.

Think about your own patterns, or those of entrepreneurs that you know. Like some young men (or women) who find themselves in similar relationships with different people, the more I invest in Silicon Valley startups the more I see ambitious entrepreneurs repeating their inner dramas outwardly in their startups.

Your internal patterns are like dragons. There’s an old Chinese proverb about dragons: “Ignore the dragon and it will eat you. Confront the dragon and it will defeat you. Learn to ride the dragon and you will take advantage of its might and power.”

The key is to recognize and learn to utilize the strengths that are hidden in your patterns, not to be consumed by them.

Read about the inner art of entrepreneurship — this week for free on kindle!

3. Learn to use your intuition and follow the clues.

As you learn to clear your mind, you will also be able to tune into your intuition much more clearly. Sometimes, a little hunch, gut feeling, a funny feeling, an unexpected coincidence, synchronicity, or even a particularly vivid dream can lead you out of a troubled situation to a whole new level of success. I call these forms of intuition clues. Like a good treasure hunt or mystery, clues are only revealed one at a time and we have to be able to both recognize them individually, and assemble them into a larger pattern.

A few years ago when I was starting an XML-content management company, we couldn’t find a name that we liked. I happened to be visiting my parents in Michigan, and was driving on I-94 near Ann Arbor when I noticed a vaguely familiar name on the side of a building: Arbortext. I had a funny feeling when I saw it, the kind that stays with you even if you don’t know why, sort of like a déjà vu.

Taking this feeling be a clue, I decided to follow it. Initially, it provided a simple answer to our naming problem. The founders of Arbortext had named their company after their college hometown. We decided to do the same and named our company CambridgeDocs. But that wasn’t all. Following the clue further, I did some research on this company an realized they were in an adjacent market space, so I got in touch with one of the founders of Arbortext to tell him about our product. To make a long story short, they became our biggest customer and gave our little startup a ton of credibility in our market — all because I followed the clue to see where it would lead.

Whether they admit it or not, most investors rely heavily on their gut feelings and intuition when making investment decisions. They then add the logical justification that’s necessary to get their partners to agree that it’s a good investment.

A few years ago, when I was at Stanford Business School, a well-known Sand Hill Road VC told us something about his process that would’ve made my analysis-oriented professors run for the hills. He said that in addition to the usual factors (market size, management team, competition), he looked for “signals” in the environment around him as confirmation before making an investment. Basically what I would call clues. Once, when he was agonizing over whether to invest in a multimedia streaming company, he went to a ballgame. While there, he co-incidentally overheard a child whose vision wasn’t great tell his father that he wished he could watch the game on his phone because their seats were so far away. This clue was enough confirmation and the VC decided to go ahead with the investment.

That’s how clues work — if you or I had overhead this kid, it might not have meant anything to us — they’re highly personalized messages from our unconscious telling us to pay attention to something. So where are they leading?

4. Connect the dots and find the larger Pattern.

Sometimes, following our intuition will lead to individual dots that won’t connect to reveal a larger Pattern until many years later. A famous example of this is Steve Jobs quitting all his college classes and falling in love with calligraphy instead. The implications of this weren’t clear until years later, when they were building the first Macintosh computer. If it weren’t for his passion for typefaces from that calligraphy class, it’s possible that you’d be reading this on a black and white or green screen in courier!

What are you intrigued by that you’ve never followed up on? This relates not just to your current startup, but your calling in life, the larger Pattern.

I used to love the idea of being a film-maker, playing out whole scripts in my mind during junior high school. Years later, after I had started investing in and mentoring entrepreneurs, I was approached by a different kind of young entrepreneur that no one wanted to fund: a fresh graduate from film school. Connecting the dots, I started mentoring film-makers and it has become as personally rewarding for me as tech startup investments.

True success and fulfillment come not just from selling a company or making millions of dollars, they come from feeling aligned what you were meant to do in this life. I call this your unique Warrior’s Path — the contributions you are here to make, and the lessons you are here to learn (which usually have to do with dealing the kinds of patterns and issues that I mentioned earlier).

Once again, in the words of the ever-quotable Zen Master of Silicon Valley, Steve Jobs: “You have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

Follow the clues. Connect the dots. Find the larger Pattern at work in your life. That’s what the Zen of Entrepreneurship is all about.

NOTE: This week, my book, Zen Entrepreneurship, is free for kindle, download it here.

Revisiting the Zen of Entrepreneurship was originally published in Hacker Noon on Medium, where people are continuing the conversation by highlighting and responding to this story.