I don’t write code, go to hackathons, wear a hoodie or live in Silicon Valley. I am no longer in my 20s. I am a woman. And I’m the founder and CEO of a tech startup.
I am different than most technology startup founders. This can be valuable in its own right; women-led startups are becoming the focus for many angel investors, and female engineers are now the target of recruiting efforts across the tech behemoths.
Yet despite my supposed marketability, I can’t ignore a feeling of dissimilarity from other tech CEOs. And I often feel very alone.
So what have I done about it? Play in a man’s world? Channel my inner brogrammer? No. I have created my own world. A cohort of my own. A path of my own. And wow, what a difference.
My career in technology was unplanned. Coming from a background in international relations, my first job out of college was with an international microfinance organization based in Boston. After a year I realized simply breathing the air in that city cost more than I was earning. Perhaps more importantly, I missed my friends, family, as well as the culture and lifestyle of my hometown Seattle.
I had always wanted to earn a master’s degree, but an MBA seemed too “business-y.” More importantly, it seemed incongruous to my planned altruistic career path; I envisioned myself helping the undeserved, feeding the poor — yes, saving the world. Yet after several colleagues at my nonprofit chose the business school route, I reconsidered my original stance. The University of Washington MBA program made the most sense: it would get me back to the West Coast, and hopefully provide the credentials I’d need to move up to a senior-level position at a large — hopefully philanthropic — organization.
I quickly learned most nonprofits don’t formally recruit MBA grads. With student loans knocking, I couldn’t wait forever for the perfect opportunity to present itself. Instead I applied, and accepted, an offer in partner marketing at Microsoft.
Was this a complete departure from my goals? Selling out? I often wondered, but I thought I’d give it a go for a few years, pay off my student loans, and then move on to something more “meaningful.”
Seven years later I was still at the company, surprising even myself that I had stayed so long. But the work was rewarding, my colleagues were wonderful, I was continually challenged and I learned more than I thought possible. All positives. Yet despite the perks, the corporate machine was getting old. I began slowly percolating on a few startup ideas with a good friend. One year later, we landed on an idea that had some legs. After developing a proof of concept, finding a third founder and getting a seed-round investor on board, I decided to take the leap and run the company full time. I figured, “I know the tech world, I have a business degree, I can do this!” Hubris indeed. But without it I wouldn’t have taken the risk.
Founding a startup is an experience like no other. Like a teenager who is still trying to come into his or her own, running a startup is like navigating that awkward period of adolescence. It’s a daily whirlwind of rapid learning, carving out an identity, desperately trying to be cool, and making more than a few stupid mistakes.
When I jumped into this world I was accustomed to the daily ins-and-outs of working at a large company: weekly 1:1 meetings with my boss, annual performance reviews, team projects, and let’s be honest, expense accounts and health care.
Leaving this behind and working as the sole full-time founder at my company was not only hard, it was isolating. I was alone most days, living by myself and working by myself. I would go to Trader Joe’s to talk to someone. I missed my colleagues, I even missed team meetings.
I joined a co-working space and over the next two years tried out ThinkSpace, WeWork and Galvanize — collaborative work places in Seattle that skew heavily tech, reflecting the city’s startup community at large. All offered great environments, other people, and amenities like good coffee, happy hours and professional services.
But I still didn’t find many people in the same boat as myself. Most were much younger, male, and in the case of the tech startup world, programmers of some sort. This was noticeable even compared to Microsoft, where many of my colleagues were similar in age and life stage as myself.
My feeling of isolation was replaced by a feeling of difference.
A few months later one of my co-founders joined me in working at our startup full time. Having her and our team of contract developers involved in person on a daily basis made a difference. Yet I couldn’t scratch the feeling that I was still navigating this world on my own.
It occurred to me: Being a woman in tech can be isolating. Being a woman CEO in tech even more so.
Working at a startup is stressful. Being a startup CEO is stressful in its own way. No one else shares your perspective or carries the same onus to keep everything together all the time. You can’t go on vacation and ask your boss to cover for you. You can’t punt on tough decisions and at the end of the day it has to be your call.
Being a woman in tech can be isolating. Being a woman CEO in tech even more so.
If this sounds glamorous, believe me, it’s not. Being the face of the company, the constant voice of reassurance, the overseer of accounting, legal, payroll, hiring (and firing) culture-setting, business strategy, sales and product development is downright overwhelming. I was frustrated and at times insecure. What was I doing? Who could I talk to? What model should I follow?
I didn’t quite know, but I slowly began surrounding myself with people I could empathize with, share experiences with, and lean on.
I formed a Women’s CEO group. While there are many “women in tech” groups, and “women in business” groups, there are very few female CEOs. Just 5% of Fortune 1000 companies are led by women; among tech startups the number is only 3%.
Along with my friend Sarah Blankinship, CEO of RightPatch, we invited our respective rolodexes of female CEOs to join our informal networking group. Our goals from the beginning were intentionally vague: gather together and share experiences, determine if we benefited from those gatherings, and go from there.
What I learned surprised me. Not only was this incredibly helpful in providing the support network I craved, it helped my business as well.
Over drinks and often extending into dinner, our conversations seamlessly flowed between stories about our businesses and personal lives. I’ve made business connections, customer contacts, and earned invaluable advice. Most importantly, I found my cohort.
There’s a phenomenon among CEOs to focus on the upside, portray a sense of calm and control, and view setbacks as opportunities. But that doesn’t paint the entire picture. And for other CEOs who hear those polished stories it can feel isolating and terrifying. I would often be in formal presentations or networking events hearing those accounts and wondering, “Am I the only one who doesn’t know this? Who didn’t do it that way? Who made a major mistake?”
The CEO group provided a space where I could let my guard down. Speak freely with others. Reveal my weaknesses and, often times, brainstorm solutions to my problems.
At a recent meeting, one of the women came to dinner completely exasperated with the process of raising capital. She recounted her previous evening coming home after a painful fundraising setback, laying her head on the table and bursting into tears. Her fiancé had asked what he could do to help. Her response: “Nothing, I just want to sit here and cry.” All of us could relate.
If this seems trivial, it’s not. Having someone like me, someone who shares the same responsibilities, challenges and frustrations share her experience and, most importantly, expose her vulnerabilities was exactly what I needed.
Around this same time, I started formalizing individual mentor relationships with connections I’d made in the past. Through my EO (Entrepreneur Organization) Accelerator group, through angel investor connections, and through my old Microsoft network, I made a point to meet weekly with at least one person who could provide some external guidance and support.
While my company’s advisory board served a valuable purpose in helping our company grow and succeed, I needed help growing and becoming successful myself.
Perhaps the most valuable piece of advice I received came from my EO mentor. He counseled that instead of feeling beholden to the company, viewing it as something I “work on” or even “work for,” I should view it as a vehicle. A car, so to speak, that I can drive wherever I want to go, stopping along the way to collect the experiences I desire for my own personal and professional growth.
At first this sounded self-centered. Detrimental, even, to the success of our company by putting my own needs first. What I quickly realized was that this approach opened doors and avenues for myself, but also for our business. I shared this perspective with my co-founder, who also felt inspired to take the company in different, more creative directions based on personal ambitions.
In running a startup I often felt there was a “best” approach, a template that should be followed. In forming a mentor group and having honest, revealing discussions I realized I could do things differently and that is okay.
Having a network to represent different opinions enabled me to feel at ease changing course. It allowed me the freedom to pursue different pathways and approaches to our business model. I started exploring partnerships with companies doing fascinating things, even if not directly related to our core product. Through this, we’ve made valuable contacts we otherwise wouldn’t have found.
I often ask myself, why did I start this company? My response has changed over time. At first, it was “to learn and be successful.” Now, it is “to enjoy the experiences and adventures along the way.” I have no idea what will happen with my company, and that is the point.
It takes a lot of courage to be different. It takes even more courage to do something different. It can feel solitary, uncertain and sometimes quite terrifying. As both a woman in tech and a woman CEO I represent a deviation. But recognizing my own needs — for connection, camaraderie and support — and finding that for myself provided the confidence I needed to create my own path. It hasn’t been easy and I’m still struggling to figure it out, but I know I’ll be better for it.