People lie about being vulnerable and fake humility all the time. Entrepreneurs, however, are experts at this deception. Although it might seem like a minor issue, it can mean the difference between success and failure of your career or venture.
Vulnerability has become a big business. Brene Brown, its cheerleader-in-chief, describes it as “uncertainty, risk and exposure” that is the birthplace of “love, belonging, joy, courage, empathy and creativity.” This is a heady promise: that by removing your defenses, you will be able to foster greater connection and success.
It makes sense on the surface. The received wisdom is that romantic relationships thrive on honesty and authentic vulnerability, so why wouldn’t this apply to the rest of our lives? The X Factor of this seemingly simple equation is: what is the definition of success?
If success is being married for 40 years, I’m sure you know examples of couples that are deeply emotional, vulnerable and connected — and also those that are aloof, distant and guarded, though no less loving. If success is making a billion dollars, plenty of examples exist of emotional, connected and sensitive CEOs, and their hard-charging, cold and distant peers. When success is measured in demonstrable metrics (time, money, etc) it is unsurprising that people may choose either path.
For many entrepreneurs, success is in and of itself the goal; whatever strategies are necessary to achieve it are usually fair game. This often means authentic vulnerability isn’t our strongest suit, and it is deployed as a tactic to accomplish our success goal. Over time, it’s also become trendy to seemvulnerable as an entrepreneur — so there’s a lot of pressure to express vulnerability.
In the entrepreneurial profession, you are taught a number of things that may interfere with your ability to be authentically vulnerable while simultaneously pressuring you to express it. You learn these from other entrepreneurs, investors, the media, and from your own experience. While it isn’t clear whether these biases cause you to be an entrepreneur or are a result of living as an entrepreneur, you may relate to some or all of them.
Always Be Closing
The number one skill of entrepreneurship is sales. Selling investors, employees, advisors, the media, your family and even yourself is a critical success factor for most high-growth startup CEOs. The best entrepreneurs are extraordinarily good sales people, even if they come with a disarming or nebbish exterior (think Bill Gates).
To be good at sales, you must be able to identify the underlying needs or demands of your target. Great sales people can readily adapt their personality and methods to give people what they think they need. I’ve seen plenty of great CEOs put on the cloak of vulnerability if they think that’s what people want. I’ve even done it myself, tweaking my humility and confidence levels on the fly to match my target’s desires.
I’ve learned that while it’s a good strategy for closing the deal in the moment, if it’s not authentically you, it may be like writing a check you can’t cash.
Only the Paranoid Survive
In order to fit into tech’s co-working or accelerator culture, you often need to take a more vulnerable posture. The stated values of such organizations always focus on fostering community and mutual support. Smart entrepreneurs learn to turn this vulnerability on and off as needed.
My favorite script is when advisors, mentors or investors ask “How Can I Help You?” In this moment, you are expected to have some burning issue that is keeping you up at night at the ready, and be able to spill your guts on command. If you don’t respond with sufficient vulnerability, you may not get their help. Conversely, if you say you don’t need any help, they will think you’re lying. And if your real issues are deeply competitive, you need to carefully assess their potential loyalties before laying your soul bare.
A major missed opportunity is for accelerators and co-working spaces to help train CEOs on how to be vulnerable, rather than just assuming it comes naturally. The lack of forethought on this is evidenced by the steady increase in founder mental health issues despite the proliferation of entrepreneurial “community” organizations. If people were being honest about their issues, they would get more help, faster. Somehow, it seems the inverse is true.
Investors are Sociopaths
Though there is little scientific research on the psychology of venture investors, if you’ve been around for a while and raised money from many different people (as I have), a pattern starts to emerge: investors are mild (medium?) sociopaths. I’m generalizing here — many investors are clearly not this way — but it sure feels like it.
Sociopaths have many characteristics, but the unifying idea is that they don’t care about the welfare of others. This conflicts with the overt posture of most venture investors of course. They have taken great pains over the last 20 years to talk about how “founder friendly” or “mission driven” they are. And if you socialize in tech circles, there are always investors hanging out at parties, making a point of fitting in and befriending upstart entrepreneurs.
You quickly learn however that they often don’t really care about you, your well-being or the mission itself. The goal is to grow as quickly and aggressively as possible, and no matter what they say, they expect you to sacrifice everything to create value for them. Under those terms, it is vanishingly easy to manufacture the kind of vulnerability they want to see (openness to collaboration, for example) while hiding real issues, such as mental health, founder conflict, etc.
Again, not all investors are sociopaths. But some very clearly are — and because it’s hard to tell the difference, entrepreneurs have mostly learned to share their true feelings with great caution.
Stay Calm and Protect the Team
One of the other barriers to entrepreneurial vulnerability is our m/paternalistic instincts. Many founders enjoy the challenges and opportunities associated with developing and nurturing the team. Though most of your earliest hires will be very pro-risk, pro-failure and pro-startup folks, sooner or later you’ll be needing to recruit people with a lower tolerance.
In response to this, many CEOs believe they must act as a buffer between the vagaries of the outside world (e.g. financing) and the day to day of the team. The main idea is that nothing good can come of folks being scared or distracted. We’re also taught that equity shares should be somewhat proportional to the amount of success-stress each person is under. That is, the closer you get to sleepless nights, the more of the company you deserve.
So founders learn not to be super vulnerable with the team, usually driven by the best of intentions. But if you don’t learn how to code switch your vulnerability, the default pressure to protect everyone else will likely leave you starved. That is, your default mode will be to withhold instead of share — and long term this may undermine your personal and professional relationships.
For all these reasons (+toxic masculinity) it is obvious why false vulnerability is so pervasive in tech entrepreneurship. It doesn’t seem to be genuinely rewarded, and it often gets punished, even when it might produce superior results. Founders therefore tend to be good at knowing when to be vulnerable rather than how to be vulnerable in their professional and personal lives.
This leads to a host of mental health, wellness and cultural issues that impoverish our society and the individuals most entrusted with creating change. The sooner we address these structural problems, the sooner we can foster a more connected, authentic and positive entrepreneurial culture.
It feels really great to be your authentic, vulnerable self. It’s time we gave entrepreneurs the tools to feel that free.