Startup Advice from the Zen Masters

Startup Advice from the Zen Masters
May 10, 2016 Brett A. Cenkus
balance business high wire tight rope

“The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.” – F. Scott Fitzgerald

The Dangerous Side of Unflinching Confidence

Early in my career, I invested in a startup with a very charismatic CEO. He had an answer for every question. He exuded confidence and certainty. He knew exactly where the company was headed. I felt so great getting in on the opportunity.

Until real life intervened. Things rarely go perfectly in startup world, and this startup was no different. When a company marketing initiative failed to generate the results we all expected and we asked the CEO about it, he was as clear about what went wrong as he was originally about why it was going to be a massive success. Now, he was championing a new initiative with unflinching confidence.

It didn’t take a few of us very long to realize this CEO only knew one approach – 100% certainty, lots of bravado, “come with me, I know the way” leadership. When things got really tough about a year in, the investors and employees started to get a little tired. All that confidence and certainty was looking wildly misplaced. It was impossible to have an honest conversation with the CEO about real risks, let alone offer him startup advice. Investors want to provide startup advice, but not if founders won’t listen. This CEO was either completely unable to hear our startup advice and talk candidly with us or he simply refused to engage at a thoughtful level. It was always more of the same – “follow me, I know the way”. I soon learned that it’s a fine line between confidence and delusion and this startup CEO was a mile over it.

I never once saw that CEO present a front of anything but unbridled optimism and unflinching certainty in the path the startup was on. That investment didn’t pan out, although I learned a couple lessons I will never forget. The most important of them is that I want to work with startup founders that realize honest communication and consideration about what we are doing isn’t weakness. It doesn’t undermine passion or leadership. Some level of openness and authenticity is necessary in order that we can make the best decisions together. There is a time for confidence and a time for honest communication about what we know and don’t know.

Startups are a Series of Highs and Lows

The startup journey is a tough one. It’s rarely a straight upward trajectory. Instead, it’s a series of highs and low. One day you are up, the next you are down. You have conquered the world on Monday, and by Tuesday you’ve convinced yourself that you made a massive mistake leaving that cushy corporate job to launch a startup.

Even when you learn to live with these emotional swings, running a startup will challenge you in all sorts of other ways. Among them is figuring out how to lead. Some startup founders fall into natural approaches they have learned earlier in life. Others model successful, public leaders and CEOs.

Beyond general leadership style, there are the myriad of questions about how to raise funds from investors, how to handle employee issues and giving out equity and things like how to manage projects and execute on initiatives. These specific situations generally require more custom and actionable advice. Startup founders generally look to mentors and other advisors for answers here. Or, they drink from the bottomless well of information and startup advice that is the Internet.

Awash in a Sea of Conflicting Startup Advice

However, processing all the startup advice you’re bound to take in leads to its own challenge – how exactly do you make sense of it all? How do you reconcile the startup advice and apply it to specific situations in your startup?

Everyone seems to know exactly what you ought to do. Investors, friends, family, bloggers, advisors – everyone has an opinion and is quick to offer their startup advice. However, the advice will often conflict. At times you will feel precariously perched on a high wire, stuck in the middle, not knowing which way to move. And, if you cast a wide net and look to a lot of sources for startup advice, as I’m always inclined to do before making a decision, this need to process a lot of contradictory advice is a common eventuality.

Perhaps you have heard that you should follow your passion. Gary Vaynerchuk preaches following your passion and he knows what he is doing. Gary is brilliant, confident and successful. On the other hand, Mark Cuban said the advice to follow your passion is “easily the worst advice you could ever give or get.” Mark will tell you that passion isn’t “worth a nickel” and that you better create something people need and will pay for.

On one hand you will hear that you have to be teachable, on the other hand someone will tell you that confidence and unwavering commitment to your idea and vision are the key to startup success.

You will be told to focus on a niche and own it, but meanwhile the venture capitalist all seem obsessed with the raw size of your startup’s target market. Which is it?

We celebrate entrepreneurs who “fake it ‘til they make it,” but how do you reconcile that with the broader movement for greater authenticity and vulnerability. Which is better in startup world?

Startup founders are told to measure, measure, measure, but follow their instincts. Is it logic or intuition that carries the day?

Persistence is key, right? Yet at some point, you know you are supposed to pivot.

Venture capitalists will tell you that startup ideas don’t matter, startup execution does. Meanwhile, no venture capitalists or angel investor hand out blank checks, even to successful serial startup founders. So, the idea must mean something.

We are told that competition is a great thing. It validates and builds markets. Who doesn’t want other companies building up their market demand? Too much competition, though, and no venture capitalist or angel investor is going to write a check to your startup.

Is it about aggressively chasing market share or reaching profitability in your startup as quickly as possible?

You are told to “just ship”, “perfect is the enemy of progress” and follow the lean startup method. But, meanwhile entrepreneurs are told to have pride in their work and make amazing things.

Are customers forgiving or do companies never get a second chance to make a first impression? You’d better know which it is, otherwise the lean startup method may be your death knell.

Are startups supposed to listen carefully to their customers? We all thought so, until Steve Jobs convinced us that no customer has any idea what they want, so there’s no point asking. I suppose we can ask and not listen. Is that the right approach?

Step 1: Realize the Seemingly-Conflicting Startup Advice Can often be Reconciled

It’s enough to make your head spin. Or, at the very least, paralyze you up in the high wire, not knowing which way to move. It’s tempting to just tune out all that noise and do whatever feels right. However, while seemingly contradictory, all this different advice isn’t necessarily contradictory. And, frankly, it’s not all that different from what’s expected of a great entrepreneur or businessperson in a more mature company, other business contexts than the startup journey.

In their ground-shifting work, In Search of Excellence (1982), Tom Peters and Bob Waterman point to simultaneously loose-tight properties as a common theme among successful companies. What they meant is that successful companies balance worker autonomy with centralized direction; they focus on their current core competencies but still invest in R&D for the future; they empower employees to be individuals while espousing collective core values. At first glance, these things all seem like mutually exclusive approaches, but they are not. It turns out that companies that strike the right balance between each opposite approach achieve uncommon success.

Balancing Two Different Approaches in Business and Life

There are generally two very different approaches to execution in the workplace — two very different management styles (e.g., Theory X and Theory Y), two different paths to growth (e.g., organic versus mergers & acquisitions), opposite approaches to marketing (e.g., it’s all about beauty/design vs. selling features and benefits). Success can be more easily found by balancing the different approaches than by going all-in on one approach.

And, in this way business actually mirrors life. There is justice and mercy and a society needs to balance them. We all have thinking (logic) and feeling (intuition) selves and we operate at our best when we use both. In negotiations, you are best served at times by playing hardball, at other times by taking a more collaborative approach. When you play poker, you should not always play super tight (i.e., only play good cards) or your opponents will size you up and take advantage. Now and again it pays to be caught playing loose.

Republican and democrat, rich and poor, yin and yang, hot and cold, fast and slow. Our world offers us extremes, and they help us make sense of things. But, the fact that extremes exist doesn’t mean we should always operate at the extremes. The startup CEO I talked about in the opening story had a great trait – he was confident, at least he was able to exude confidence. That’s useful. However, if isn’t ever balanced by honesty and thoughtful consideration about the way forward, it becomes a huge risk. I won’t ever partner with him again. It’s maddening.

The Middle Ground is not Lukewarm

The problem with all the advice out there isn’t that it’s conflicting, it is that everyone presents their advice on absolute, uncertain, always applicable terms. As the startup CEO in my opening story knew, we are suckers for confidence, even when it’s not genuine. We think we have finely tuned BS meters and over time I like to think mine has gotten fairly sharp, but it’s not infallible.

We fall for delusion masked as confidence. Nothing is more textbook than false bravado, actually insecurity, masquerading as true confidence. Nothing that is, except our collective willingness to ignore the signs of it. We do this for a lot of reasons – excitement, greed, the desire to belong. Although I think we mainly buy the 100% certainty pitch because Americans are notorious for disliking ambiguity, and operating in the middle may feel like ambiguity at times. Consequently, we gravitate toward the extremes. We like things black and white. We read books that champion extreme approaches. We like extremes and the certainty provided by espousing that there is always one way to do things, often a crystal-clear, extreme approach.

But, here we aren’t talking about ambiguity. We aren’t talking about the lukewarm, can’t make a decision, stuck in the middle ground. We are talking about choosing the middle, embracing it as the right place to be. This isn’t about being stranded on the high wire. It’s about loving being out there. This is fundamentally about balance.

A Lesson from the Zen Masters

Buddhism refers to this concept as the middle way. It means to avoid extremes. The story goes that while growing up as a prince, the Buddha had access to everything he could possibly want. Nevertheless, he left his home in search of meaning and enlightenment. He wandered, living an ascetic life, living on very little foods and denying his own body. Eventually he realized that asceticism didn’t lead to enlightenment. To the contrary, the Buddha found enlightenment through balance and harmony.

I don’t necessarily recommend avoiding extremes in business. I caution against blind allegiance to them. Don’t get stuck in extremes. At times, though, extreme action is warranted. Going all-in on the startup idea that you’re super passionate about is an awesome thing. That’s how you should launch. You simply need to keep your eyes open and truly hear the feedback you get. That isn’t lukewarm, but it also isn’t blind, never flinching, going down with the ship delusion.

Startup Advice Worth Listening To

As for how to navigate all the startup advice out there, here’s my handy rule of thumb. Be very cautious before accepting startup advice, any advice, from someone who sees the world in black and white. You know, the never and always people. That kind of 100% certain, (allegedly) never failing advice makes for good sound bites, but if your investors, lawyer, accountant, consultant or best friend trade in this type of advice, move on. A confession – I’ve been guilty of doling out advice in this way. Witness my recent blog post, The Only Startup Advice You’ll Ever Need I admit, you’ll need more than this one piece of advice. It’s a good one, but it doesn’t say everything there is to say.

There is rarely one way to handle things. Rules of thumb are malleable. Apply them blindly to every situation and context at your own peril. Very few issues you will wrestle with in your startup and business career are simple, textbook issues. That’s not how the startup ride goes. Business, like life, is messy. It’s about people, and people are emotional and unpredictable.

This doesn’t need to be paralyzing. You don’t need to function as though you’re adrift at sea. And, you will find plenty of wise mentors and startup advisors who can help guide you through solid, thoughtful decisions without resorting to “one-size-fits-all” approaches.

Startup Zen: Living the Nimble Life in the Middle

When you get comfortable operating in the middle, picking and choosing approaches based on the situation, you will develop a feel for what each situation requires. This is where your intuition and gut come into play. I hear a lot of people criticize intuition. They trust logic. My experience says that logic is what you need to fear more. I’m not suggesting you abandon logic. After all, this article is about balance. That include balancing logic and intuition. But, as you move through your business career and life, you will begin to just know what a situation requires. In that case, the larger your box of tools, the wider the range of approaches you’re willing to consider, the better.

Embrace the unknown. The startup journey, like the rest of business and life, is an exciting ride. Never boring, always challenging, don’t let its unpredictability frustrate you. Be willing to try different approaches. Act, watch, listen, calibrate. Not only will your startup life be more interesting, but you’ll eventually be infinitely more effective. Perhaps one day you will be a Startup Zen Master. When you are, remember to balance all that experience and knowledge with the eyes of a beginner.

Brett is The Startup Shepherd™. He has 20+ years of experience in business law, entrepreneurship and finance. He spends most of his time on startups, joint ventures and mergers & acquisitions. Brett believes there are a lot of dumb questions, but we should ask them anyway, along with the challenging ones (and sometimes it's hard to know the difference). The real travesty is silence when you have something to say.


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