This Matrix thing is really stressing me out.

The Open Sourced CEO

Kill them with candor

I’ve been thinking a lot about candor recently. Is it possible to live a more authentic life as a CEO? One that values our messy humanity as much as our shining successes and stoicism. Yes, startups require courage, but the role of CEO has begun to mirror that of the action hero in a blockbuster movie. Startups are run by humans not scripted characters. We need to be human. We need to have feelings. We need to be able to make mistakes. And we need to be able to ask for help. A handful of blog posts, brimming with just this kind of candor, mushroomed in my feeds last week and gave me hope that things might be changing.

It started when my friend Matt Munson reached out for quick feedback on a post he was about to publish. As part of the Reboot community, we’ve been talking about sharing the entrepreneurial journey so we might normalize the experience for others, help to define a more authentic leadership style, and ultimately find a healthy way to build successful businesses. It’s a brave post, full of real numbers, actual emotions, and details that are rarely shared. Check it out:

The dilemma

Being as candid as Matt isn’t an easy proposition for leaders. There are many stakeholders in a company that a CEO is accountable to and responsible for. Sharing has consequences, mistakes have consequences not just for the team but have implications for blowback from investors, press, competitors, potential business partners, trolls and even friends and family.

The potential to be misunderstood, undermined, doubted, blamed, shunned or even fired feels infinite when your finger is hovering over the publish button. It’s much safer to say nothing, or stick to the the script of, “we’re crushing it” and bottle up the rest. I speak from experience when I say that’s what most of us do.

Unfortunately, sticking to the script has consequences too. It causes us to bury and hide our fears. When we do that, we give them more credence than they deserve. Even more dangerously, sticking to the script can cause us to lose track of ourselves, to start living for the validation of others. It’s a subtle and invisible process and it all starts before we raise a dime of capital.

“Raising money can encourage you to be someone you’re not.”

How “killing it” is killing Startups, describes how the pressure and anxiety start early in an entrepreneur’s journey. James. runs a startup called Sanctus (whose mission is not coincidentally dedicated to “Making Mental Health Cool”) and he does an incredible job of capturing the hall of mirrors the ecosystem, VCs, and founders co-create when we run the gauntlet of raising money.

“The danger is that the startup landscape is telling founders (and people working in startups) that they must live to impress others. It implies that they must perform every single day and that they must put on a show to win the affection of others who will define their success. I moulded myself on what VCs and advisors said, not on who I actually was or what I actually wanted to do.”

Casey in point

By the time we’ve run the gauntlet and actually closed a round of funding, we’re fully immersed in this Matrix of expectations, real and imagined, created for us and created by us. Now fear and ambition work to create their own universe, an approximate reality we’re seduced to live in no matter how aware we are that we created it. Casey Neistat, sold his company Beme to CNN last week. This is a guy who jumps off cliffs and hangs from helicopters on an average day, but Casey acknowledged that none of his daring feats scared him as much as starting Beme. I laughed in recognition as he described the self inflicted terror he felt running the company.

“All of that in aggregate just yielded terror that I might fail and let down all these people that believed in me.”

No scapegoats

Let’s be honest, there are so many examples of bad behavior in the investor class that we could start a douchebag awards show. Raising money and running a funded business are so difficult that it would be nice to have someone to blame … but blaming VCs wouldn’t be honest or true to my experience.

In my case, and in all the examples I’ve cited here, I placed far more pressure on myself than my investors did. If, as founders, we’re going to escape being two dimensional comic book heroes, we need to dispose of the comic book villains as well. In order to do this we need to find and celebrate investors who are willing to be more candid than your average DB Award winner.

Bryce Roberts, a VC, wrote a piece last week that may point the way, with Every Business is a Lifestyle Business. In what by now should sound like a familiar refrain, he paints a picture of founder induced pressure, but he also acknowledges that investors play a tacit role in this (emphasis mine):

“With that funding came expectations placed on themselves by themselves and by the promises they’d made to their investors. And those promises added pressure. Pressure to move fast and break things. Pressure to grow the team to meet the next fundable milestones while the bank account shrinks and the milestones move. Pressure to go big or go home. No investor asked this of the founder. But every investor asks this of the founders we fund.

The red pill

There is a way out. For very real, concrete reasons, startups are hard. But we make them harder than they need to be when we paper over the anxiety and ignore the stories that fear and pressure create in our heads. The solution may seem counter intuitive because it requires us to be vulnerable exactly when we want to be armored. James writes,

“Thankfully, the solution is pretty simple and we all have access to it. It’s called authenticity. That means being open, honest and genuine with yourself and those around you. It means being vulnerable from time to time and admitting when things aren’t going well. It means being less someone else and being more you.”

It’s not enough for us as leaders to simply play to the press, valorizing (or ignoring) the grind, the rehearsed stoicism, or what Gina Trapani calls the “pathological overconfidence” in her post last week We’re All Frauds. These may well be the required roles we play in startup life today. But are they working?

Yes sometimes, otherwise we wouldn’t do them. They might even help us close the next round. However, I’m not convinced they’re healthy for us or for the startup ecosystem in the long run. If we play a role by being inauthentic, our “escape” from the reality of our fear becomes a pyrrhic victory, trapping us deeper in the hall of mirrors, further from our true selves and seducing new founders to model our behavior and fortify the collective inauthenticity.

This hall of mirrors is sort of like the Matrix, a hyper-real place we inhabit together. The rules of this ecosystem we create together are more elastic than we think. While our feelings (fear, pressure, anxiety) are real, the often misguided stories we tell ourselves about them may not be. Unfortunately our misguided stories inform our actions and our actions have real consequences. When Neo asks why he’s bleeding after coming out of an intense simulation, Morpheus tells him, “our mind makes it real.”

Change your stories about your fears and you will change your actions; change your actions and you will change your outcome. Your mind makes it real. Luckily, our startup Matrix isn’t created by evil bots, it’s created by us. So we have the power to change it. It may be scary, but it starts by being more authentic, more human, more vulnerable.

There’s a thread that winds through Matt, Gina, Bryce, Casey and James.’s posts — candor about their experiences. After Matt hit publish, he wrote to our group,

“I really want to start writing about the entrepreneurial journey and my experience of it to help normalize the experience for others. I meant what I said in the post that I think we should all talk more openly about this stuff.”