Dismantling Silicon Valley Stereotypes
By: Cailin Hardell
Tags: Female Founders, Ycombinator, Leadership, Entrepreneurship, Silicon Valley

“In Silicon Valley, admitting mistakes and showing your vulnerable side is one of the biggest social faux pas that I’m tired of trying to follow.” — Maren Kate, May 2016

Photo by Om Malik on Unsplash

“You sounds really young, how old are you?”

“Tell us about a time when you broke the rules.”

“Are you sure you aren’t making a pinprick blood test ”

“You need to show them who’s boss”

“Fake it ‘till you make it.”

All of these phrases have been asked of me during my time as a founder and entrepreneur, and all of them have another thing in common: they’re indicative of a larger Silicon Valley culture problem. For the first 6 months or so after starting Segmed, I felt trapped by a few things I felt had to be true of me as co-founder/CEO of my company:

1- you need to be a rule-breaker

2- your company should be your be-all-end-all

3- “fake it ‘till you make it”

4- as cofounder-CEO, you should be omniscient and omnipotent

I grew up in the Valley and watched it balloon from a tech niche into the sprawling, congested Hollywood for startups that it is today. When I started Segmed I noticed the effect that these beliefs, imprinted in me by my time in the entrepreneurship bubble at Stanford and by growing up in San Jose, were having on me. Over the last 18 months I’ve struggled against them — at first trying to be someone I’m not so that I fit the stereotype — but eventually, finding my own rhythm. And things at Segmed have gotten much better since I stopped trying to be someone I’m not. In my opinion, these cultural tenets are bullsh*t and often rooted in misogyny, and to be a great founder and leader you should throw them out the window and make your own.

You need to be a rule-breaker.

“Good girls aren’t hungry, furious, or wild. All of the things that make a woman human are a good girl’s dirty secret.” — Glennon Doyle, Untamed

Men are taught to forge their own path. Women are taught to follow the rules. Men are rewarded for being clever, cheeky, and rebelling. Women are expected to be nice, and pretty, and to keep everything together and pick up the pieces.

It follows then, that this Silicon Valley tenet that being a “rule-breaker” equates to success is automatically more exclusionary towards women than men. If you couple this expectation with the fact that women don’t tend to apply for a job unless they’re 100% qualified, then with this expectation alone you can explain a big chunk of the gap between men and women starting businesses in the Valley.

When I started Segmed I felt like a fraud because rule-breaker is the phrase you’d use if you had to describe the opposite of me. I wasn’t a rebel. I never got in trouble at home or school. I was the ‘perfect’ example for my younger siblings, valedictorian at my high school, graduated from college, went to grad school at Stanford and always made sure to cross my i’s and dot my t’s and do everything that was asked of me as exactly as I could.

The famous rule-breakers of silicon valley: Elon Musk, Travis Kalenik, Steve Jobs, etc. are sensationalized and household names. They are so unlike everybody else that they have movies made about them, and books written. But there are plenty of extremely successful founders who succeed with quality leadership and quietly inspire as much awe and strategy to their investors and teams than those notorious men do with fear and power. These founders — like Sara Blakely, Eric Mosley, Mathilde Collins, Reshma Saujani — I would much rather lead like them with consistency and collaboration than by considering myself exceptional.

You don’t need to be a rule-breaker to innovate. I’ll say it again — you don’t need to be a rule-breaker to innovate. Innovation is about doing something new and having a vision of a better future. Anyone can have a great idea and do things differently than they’ve been done before — not just ‘bad boys’ with something to prove. In my opinion, being a rule-breaker could be phrased differently to drop the rebellious connotation, be more inclusive, and better capture what the best of the phrase is getting at.

Your company should be your be-all-end-all.

“Stress is a well-known creativity killer” — Robert Epstein, PhD

Picture what you think a startup founder looks like.

What comes to mind for me is a tortured genius who is consumed with passion for his/her company and works 24/7. The founder will not rest until the idea succeeds. There’s a reason investors like and sometimes encourage this archetype.

Oddly (or not), this archetype goes against research about what makes a good leader, engineer, or otherwise productive human. We need balance. We’re more creative, empathetic, and stable when we are taking care of our physical and mental health. Early in a company’s life you make decisions that set you on certain paths almost daily. If you are sleep deprived, wired, manic or emotionally unstable it’s going to be hard to think things through and you’ll be tempted to wing it.

I have never been a tortured genius, I’ve always been a steady planner. I’ve never pulled an all-nighter. I can count on one hand the number of times I’ve had to stay up past midnight to get something done on time (and none of them have been for Segmed). It might be easy to peg me as “not working hard enough”, but my results speak for themselves.

“Your company should be your everything” was the first startup stereotype that had to go out the door for me because I’m used to feeling… good. I know myself, and if I was forced into this box and not allowed to do any of the other things that make me who I am I wouldn’t have made it very long. Having anything be your everything is scary. For me it created a pressure-chamber that I couldn’t see out of.

Creating some separation between Segmed’s success, my own health, and who I am as a person allowed me to step out of the pressure chamber and enjoy what I was doing. Having that enjoyment and passion present keeps me ideating about what could be for Segmed and makes me happy to show up for work every day. I don’t beat myself up for taking weekends off anymore, and I hope that my team can follow my example and keep a balance between their humanness and their desire for Segmed to succeed at all costs.

Read more about the problems with mental health in entrepreneurship here. If you need help, call the national suicide prevention lifeline at 1–800–273–8255.

“Fake it ‘till you make it”.

“Fake it ‘till you make it” is a phrase you hear a lot in sales and startup culture. This type of thinking means that at your most vulnerable point — early in your career, at the start of a new venture, when things are tough — instead of asking for help in an authentic way, you must project an image of success that hasn’t materialized yet.” — Maren Kate, May 2016

“Fake it ‘till you make it” is a stereotype I have mixed feelings about. On one hand, as Maren Kate points out, when it is applied too liberally it can mean bluffing and avoiding help from those who might be able to offer a lens of experience. However, I’ve also used it to feel confident and sell my startup when I didn’t feel that way.

An example of a positive use case might be getting in the door with a big customer and selling them your product or service. The first time you get a meeting like that you might have no idea if your product creates the value you hope it will, just hypothesis and hope. You should be open about your stage and you definitely shouldn’t lie, but projecting confidence in yourself and your company is going to be pivotal to making the sale. In this case, “fake it until you make it” was useful to help Segmed get off the ground with stakeholders who are important to us until we had tangible evidence.

The use case of ‘fake it ‘till you make it’ that is more harmful is when you start to fake it in all aspects. No one, and no company, is perfect. If you’re trying to convince yourself, your employees, your investors, and your customers that you have everything figured out all the time, then 1) they’ll be able to smell the bullsh*t and it’ll probably backfire anyway, and 2) you’re needlessly isolating yourself and likely missing out on some help that would make a difference.

As Maren points out, this one is all about vulnerability. Many founders that I’ve met are perfectionists who are used to being good at things. It can be tough to admit something that you perceive as a failure or a shortcoming, but it’s something you need to actively practice doing. For your sake, for your teams’ sake, for your companies’ sake.

Founder / CEOs should be omniscient and omnipotent.

“Think of how Mark Zuckerberg, Steve Jobs, or Elon Musk are portrayed in media or film — recalcitrant geniuses who have no life outside their work and no end to their drive, but likewise are utterly useless when it comes to caring about people. The company is all that matters. Projecting strength and achieving success; that’s what a real leader does.” — Rand Fisher, Lost and Founder

If your exposure to Silicon Valley was just through media, hell — if your exposure to any CEO’s personality type was just through how they’re portrayed on screen, what would you think? Command, control, strength, and power. Maybe it’s a fit of rage and firing someone on the spot. Maybe it’s changing strategy mercurially, with just the wind at your back and no one else’s input. I’ll put an end to that fantasy right there.

Being a lone wolf is scary. We should stop glamorizing it. Thinking you know everything better than everyone else is dangerous and never true. At Segmed’s outset I was terrified thinking that I needed to have all the answers like my idea of the stereotypical CEO. Once or twice since then I’ve tried to play the “we’re doing it this way since I’m the boss” card, and it has never worked out well (maybe everyone has to try that for themselves). It’s also not who I am or my leadership style.

The only way I’ve been able to effectively convince anyone to do anything has been by getting buy-in to a vision and working with everyone involved to come up with a plan that makes sense. The culture of a company is immensely important to its output, cohesion, ability to attract talent, and longevity. Starting with founders that can cultivate a sense of belonging, ownership, and inspiration is a good first step.