Why Being Real Matters

Lying is a requisite and daily part of being a founder, the grease that keeps the startup flywheel running. No one likes to put it that way of course. Instead, we use phrases like “hustling” and “fake it until you make it” to make the idea of lying more palatable. “Information control” is among the most important skills a founder has traditionally needed for success, and these euphemisms change nothing of the daily behavior.

But times are changing, and everyone is getting more sophisticated about startups. People know what questions to ask, and are not afraid to aggressively probe to get the answers they seek. That means that some of the key myths about success in Silicon Valley are at risk. We need a new transparent approach toward information, but we also need to understand that startups are inherently risky – and accept the lies as they come.

— Danny Crichton in Startups and The Big Lie.

Crichton, who is a former colleague back in my days at The Stanford Daily, has a great line about how startups “run on an alchemy of ignorance and amnesia that is incredibly important to experimentation” and that entrepreneurs essentially have to lie a lot of the time about how things are going.

The Relentless Push to Be Positive

It’s very popular to lament the fact that founders are always saying their startup is “crushing it” and growth is through the roof. But most of those people don’t have startups of their own, because otherwise they’d understand the pressure to make it seem like everything is awesome. No one wants to invest in, work at, or buy from a company that is struggling. This is also true for people: no one wants to hang out, work with, or date a negative person or a whiner.

But that kind of talk comes at a psychic cost, and is why nearly a third of founders struggle with depression and/or anxiety problems. The typical point here is that you need to build a support network of friends and family who you can be open with and who won’t judge you for your lack of success.

But I want to make a broader point – one that applies not just to founders, but anyone really. The point is this: being vulnerable and honest about your struggles is important not just to get things off your chest, but because it creates deeper connections.

Real Relationships Come from Being Real

At the end of the day, no one is perfectly happy with their lives. Everyone has insecurities and struggles, and if when they interact with you, they only hear the good stuff, then they are less likely to talk about themselves, especially if they’re perhaps less outwardly confident or have external indicators of success to point to.

By opening up and talking about the things that worry you or are not going well, you allow the other person to bring down their guard, and both of you can form a better relationship. I have a few very close high school friends and I remember the moments that brought us closer together were when we were talking about girls we liked, which for a 15 year old guy, probably the scariest and most vulnerable thing you could talk about.

More recently, I’ve been going through several difficulties in my own life. I send out a quarterly newsletter to friends and family and included a very honest and un-sugarcoated version of what happened. What surprised me is how many people then reached out to tell me they were there for me and that they cared. Typically the newsletter gets a few responses, but this time, I probably had 2 or 3x as many people writing back. I was touched, and I was reminded how important it is to just be real.

The Power of Vulnerability

University of Houston professor Brene Brown gave a popular TED talk on the topic of vulnerability, shame, and worthiness. She argues that being vulnerable is both the “core of shame and fear and our struggle for worthiness” but also the “birthplace of joy, of creativity, of belonging.” To some degree, a lot of the bravado around startups, and our ambitions to achieve in our careers, or look good, or be popular, are around want to feel accepted, to fit in and to feel worthy.

The talk is interesting, funny, and convincing and Brown went on to publish a book on the same topic that I’ve heard good things about: Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead

At the end of the day, there are of course times when we want to be prudent about what we’re sharing. Things that we say can be used against us, and our goal isn’t to go around spilling our deepest darkest secret to total strangers. But don’t underestimate the power of disclosure, of being open about difficulties. It helps you accept your own situation for what it is, engender trust and good will, and builds real relationships.