Recalibrating Start-Ups: Maybe the entrepreneurs, venture capitalists and the startup world are unable to let go of the notion that all you need to make a billion dollars is a cool spokesperson and an idea.

Dave & I, Assisi, Italy

In the startup world it seems that instead of valuing ability, or great leadership, we value people who we consider cool. When they first started out, Bill Gates and Steve Jobs were anything but cool or hip. Being rich and successful makes people admire you after the fact, and somewhere down the road the cool kids learned how to take advantage of brilliant nerds. Eventually, Steve Jobs started to adopt a cool kid aesthetic, and his company followed suit. They recognized that cool sells. At the same time that Jobs started setting himself apart by wearing black turtlenecks and tiny wire-rimmed glasses, his company started walking away from whimsical-looking,  easy-to-use, long-lasting computers, to slim, stylish appliances with no removable batteries, no ports, and no buttons.

The tech world has followed suit. Today’s groomed beards, juice cleanses, kale chips, and energy work are just the latest version of Steve Jobs’ black turtlenecks and wire rimmed glasses. The tech industry was built by dudes with bad fashion sense but a well-developed sense of wonder and adventure. People who cared a lot more about epic hacks and big ideas than about trendy shoes or personal grooming. Guys like Steve’s Jobs’ Apple co-founder Steve Wosniak. But today’s entrepreneur wannabes style themselves much more like late-period Jobs than early-period Wozniak.

I think cool has its place in the success of a startup. But is being cool all you need to succeed? I am not sure. Nevertheless, I would suggest that striving for cool is undermining basic productivity, ultimately getting in the way of startups’ potential success. Before it is too late, I think it is time to recalibrate our conventional entrepreneurial norms, which means we should move past the standard appearance bias and focus on what it really takes to have a successful start up.

Dave, The Forum, Rome, Italy

First, and before I dive in, let me give you some background. I often write about feelings, dark thoughts, crazy neighbors, and family failings. My observations come straight from experience. It has been years since I have been clear about my connection to the tech start-up world. In truth, it is a world that consumes an extraordinary amount of my everyday life. See, before Dave and I were even married, we were already riding the boom. Dave co-founded an ecommerce software company in the mid 90s and also owned an e-retailer selling mountain bike equipment. I worked for another early stage startup. We both had a hand in online-commerce-enabling traditional brick and mortar companies. I still remember pitching reticent souls. I can hear them now, “No one will ever buy anything online.” As  we all know, they were wrong. It even seems ridiculous now to ever think they could have been right. That is also why I understand how compelling and frightening ideas really can be. The earth was flat until we were able to see it was round. 

Florence, Italy

In those early internet days, all of us high tech entrepreneurs goldrushed our way into this new frontier. Once on board it was easy to fantasize on paper money promises. When we hit it big, we were definitely going to buy an east coast mansion. Then the dot com boom went bust,  9/11 blew up the economy, reality set in and our dreams went sideways. Nevertheless, we had some early success, reminding us how great the startup world could be. Consequently, we held on. Dave continued (to this day) pursuing several more tech dreams. I, along with my stress-relieving nicknames for his coworkers, remain an active observer. I was good at deconstructing why Evil Shrek, Lego Darth Maul, The Chief Kale Officer,  and Tiny Hands would not function in a regular, 9 – 5 world. Their dreams were too big. Their leadership was less than mediocre. They stole success for themselves and undermined anyone who got in their way. Occasionally I would wonder out loud, 

“Dave why don’t you work for a more traditional company?” 

His always response:

“It would kill me!”

Dave & I, Rome, Italy

We continued taking risks. I knew this was a career the day we were able to take out a home loan based on and I quote, “Dave is a serial entrepreneur.” Crazy. 

I focused on raising our boys.  Dave worked on the next big thing. Even when I pressed ad nauseum, I was left in the dark about how bad or great it really was. Our success never came from where we expected — ever. Of course, it was always hindered by people like Lego Darth Maul and Evil Shrek. Instead, those trying to keep the ship afloat were often scapegoated and overlooked. I have always wondered why. Isn’t success partially about the leader’s ability to see who really is getting shit done? Isn’t promotion based on the one who actually knows the product? Alas, no. Seriously, if I had a dime for every leader who promoted the cool kid instead of the smart kid, I could fund a new startup.

Us, Castel Sant’Angelo, Rome, Italy

As a result of the “cool kid” phenomenon, functioning, healthy teams still do not seem to matter, or better, they take a back seat. Because it is a land built on napkin ideas and unearned wins, bosses continue to believe that a functioning, traditional organization is not necessary. Instead, the long held start-up belief that all an entrepreneur needs to succeed is an idea, some hip dudes, a fridge stocked with kombucha, a venture capitalist with a prestigious business degree and a board member who used to work at Google. 

The upside to this belief is that said start-up works as an exciting, dynamic team, a team where everyone pitches in and gets the work done. The downside to the narrative is that often the team is undermined by unqualified leadership and a delusional vision. And even though this reality has been exposed via television shows like HBO’s “Silicon Valley,” the narrative persists. Again, why? There has to be a reason. Is it laziness? Lack of creative vision? Or simply because that is how it has always been done? 

Castel Sant’Angelo, Rome, Italy

I sort of get it, or better, I liken it to people who week after week buy lottery tickets. Somewhere out there someone has actually won the Powerball and Megamillions lottery. In fact, in start-up land, I have seen people make millions based on an idea; sometimes even a deeply stupid idea. Back in the day, the partner of my former boss literally made 6 million dollars for registering a domain name. My boss was emotionally destroyed as a result of being left out of this nonsensical windfall. He became obsessed trying to register every single domain name he could think of. Now he is in jail. (Not for domain name squatting, but for something else). I have watched other bosses appropriate, lie, con, cheat, steal, bribe, and bluster their way to the top. Of course, once at the top, I have watched these same under qualified and greedy bosses nosedive the company into the ground. Of course in every startup there is at least one enabler. You know the one. They are the coworker who literally possesses only one job skill: self-promotion. Instead of caring about the company’s success, they thrive in pushing people into an echo chamber of their own greatness. As long as it benefits them, the self-promoter will always enable a boss’ stupid leadership and ideas. In fact, the self-promoter is really good at making a boss feel cool. These shameless self-promoters, with their ironic t-shirts, juice cleanses, paranoid insecurities, half-hearted databases, and overblown sense of their own importance, also defy logic. Using their under qualified bosses, they rise to the top. How?  Well, they are geniuses at getting their naive bosses to see the world through their greedy, self-promoting lens. While the true leaders, those who probably suck at self promotion, are busy trying to save the ship, the self-promoter is using their skill (singular) to appropriate other people’s work and to get other people to do their work. 

Me, Somewhere in Rome, Italy

Maybe it is a value thing. Meaning, we think good leaders are cool when in reality a successful leader is an excellent, hard working team player, one whose work inspires others to work hard. I am tired of having a front row seat to the nosedive or unnecessary fade into failure. That is why I would suggest that for start-ups to succeed, it is time for this hip, magical thinking-styled narrative to change. For this to happen, I would suggest that company boards, venture capitalists and the startups get over their own self importance  and adjust how they view employees and their roles. Now with a new metric regarding what makes a good leader, the decision makers are able to make space for the competent leaders; you know, those who actually need to be leading these companies. Maybe the first step is to convince all the shameless self promoters that it actually benefits them to promote the smart, capable ones, the ones who will actually make you some cash. 

I will sum my observations up with what a friend just told me:

“A car might be shiny and pretty. Without it’s engine, it cannot run.”