The Truth About Starting a Startup

(I wrote this for YC’s Future Founders Conference for Women. I’ll add the recording when it becomes available. The actual talk I gave on November 18th should include bonus streams of unconscious thoughts and cursing, in case someone is into that.)

My parents were refugees of Communism. Wherever the line was between being poor and being homeless, my mom and dad lived just right above that line for many decades. Growing up, I watched them work seven days a week without ever complaining so my siblings and I would live a better life than they did. We didn’t have much, but there was a lot of love. All I wanted to do was make them proud to honor their sacrifice for us. 

I’m rarely the smartest person in any room. I went to a state school. I liked math and architecture, so I studied to be a construction engineer. My work uniform was a hard hat, orange safety vest, and muddy boots. While I worked in construction, I saw firsthand why projects are so often behind schedule and over budget. We built PlanGrid to solve the problem that we experienced in the field.  

I grew up at PlanGrid. It was the most beautiful thing to me. I loved it completely with all my heart, to an unreasonable and unhealthy degree, and I think it has to be that way for startups to work.  

When I look back at our almost decade journey, however inspiring our technology was, or how impressive our growth was, the happiest memories in my heart, the only ones I’ll remember 20 years from now, are always with people. It’s an incredible feeling, building something people want, seeing their jaw drop from awe at something you’ve made for them. One of our early users told us, “after 30 years in construction.. this is the best tool ever given to me.” And nothing compares to working hard with people you trust, running at full speed towards the same mission together.

We had a reputation for being good people building good software for the construction industry.  Some construction publications would refer to PlanGrid as the “Darling” of construction technology, and I remember I didn’t know how to feel about it at the time. I think I wanted to be associated with a noun that was less lovable and more fierce. But I now realize it was their way of rooting for us.

A big part of our reputation came from how we interacted with people. And it was so simple and true to who we were. We just treated others the way we wanted to be treated. We were normal, decent people who loved building things. If this is your vibe also, please don’t be afraid to show it because even in business, it resonates with people. I’m proud of the culture we built at PlanGrid. 

But as high as the high moments were, there were a lot of unhappy and hard ones. And that’s just how business is — When it feels really good, it probably means something terrible is about to happen. And conversely, if it is feeling awful, it will get better. That, or it’ll feel bad a little longer, but it always vacillates back to good. I’ve come to believe that a big part of our jobs as founders is to manage our own emotions through the emotional rollercoaster called building a startup.

And I think that’s why company building isn’t for the faint of heart. It doesn’t matter how well we were doing; it never got easier. Because as we’re trying to find product-market fit, as we’re trying to get people to part with money for our product, life continues. Meanwhile, life doesn’t stop just because you're stressed out doing the hardest thing you’ve ever done before.

I remember how excited we were to get accepted into YC’s Winter 2012 batch. As we were launching our product into the world, living the entrepreneurial dream, sleeping and working out of our Silicon Valley hacker house, we were also experiencing the cruelness of life. We watched our cofounder die at 29 years old. We watched cancer eat him alive, and there was nothing we could do to help him. We felt heartbroken, angry, and confused. I remember on so many occasions; I would turn the corner in our house to find one of my co-founders, who are all tall, strong men, sobbing in a corner, mourning our best friend.

And this is the journey. 

Because we weren’t unique snowflakes with this terrible thing that happened to just us. As our team grew bigger to hundreds of people worldwide, it felt like sad stuff was a constant: parents and partners dying suddenly, children getting sick, deeply tragic stories of life.

And it’s why, whatever you have chosen to work on, it has to be worthy of your time here. Because if you have any success at all, it will be at least a decade of your life. A decade of life where you are doing nothing but working on the problem you have chosen, obsessing over it and neglecting friends and family, a decade of barely taking care of yourself because there isn’t enough time to do anything but build.

We always had excellent health and dental insurance for our team. But I rarely used it. Not because I was so healthy or had great teeth, I just couldn’t find the time. So when I wasn’t CEO anymore, I finally went in to get a bunch of things checked out, including my long aching teeth I had been ignoring. My dentist found six cracked teeth, all from grinding at night. When he learned that I was a founder, he said, “that makes sense, cracked teeth from stress.” Stress messes up your body — and starting a startup will bring you to a new level of stress.

I often get asked about work-life balance.

I never figured it out. Work-life balance is such a beautiful concept in theory. You get to have your cake and eat it too. Let me give you a few examples of why it was so hard for us to find work-life balance:

When we only had months of runway left in the bank, there was no work-life balance. We had to work around the clock so that our company could survive. When we were behind on our big product launch, when we’re behind on our revenue goals, when we released nasty bugs to our users, or when our servers were down, there was no work-life balance. 

And then there are unforeseen conditions. What startup included Covid19 into their new fiscal year plan. Shit seems to happen often while building a startup.

And by the way, it doesn’t matter how big your company is and how fast you’re growing. There are never enough resources. Even when we got to $100m in recurring revenue, we still didn't have enough people to build and support our customers, not enough money to invest in our business’s growth.

And then there are competitors. 

Some competitors had way more of everything we did. And if they didn’t have more resources than we did, we had to assume they were working their hardest to eat our lunch and dinner. So the only thing we could do to compete was to make ourselves into multiple people, 10x if we could.  An easy way to 10x ourselves was by not having a personal life and not taking care of ourselves.

It might surprise you to learn that I’m not trying to convince you not to start a startup. I only want to properly warn you about the commitment of building a startup, so you can better prepare yourself than I did.

But I lucked out. We had picked a problem to solve that we cared about. And it turns out; it is much easier to do a good job at something that we love. I loved building tools for people who take showers at night because they reminded me of my immigrant parents and how hard they worked. I believed that if our software helped them get home to their kids, even 10 minutes earlier, it was all worth it.

I think there is a balance to everything in life. I believe that for every terrible thing that happens, there is also a good side; Even tragic things like a friend who didn’t have enough time. Of course, I would much rather my friend be alive, but the good side of this incredibly tragic thing that happened was that we got a front-row view of how short life is. I remember thinking: “How lucky I am to be alive and still have time here?” A big part of me realized then that I wanted to build something beautiful for myself and in memory of my friend. 

The only reason PlanGrid worked — was that we loved it, and we poured our hearts and souls into it. 

If you’re thinking about starting a startup and pursuing something you love, do it! I’m so proud of you. I know how hard it can be, in particular, to feel judged for how I looked, to feel judged for being a woman. And whether sexism was something I encountered or whether it was mostly my insecurity — what I felt was real, and it was hard and painful.

But I want you to look at me as an example and trust that it is possible to overcome all of that.  I’m not trying to downplay discrimination because it happens. There have been people who have said crazy things to me like: “but you’re too small to found a company”, “you’re not tall enough to be CEO”, “you’re too young”, “well you’re not too young, but you look too young”. Another CEO had advised me to “hire a professional CEO who can do my job better.”

The fact is, for every person who has ever doubted me, there were hundreds more who believed in me. They could have cared less about my gender and only judged me by my work ethics and output. I promise you there are many more good people in this world, and they have been waiting to work with you.

Building PlanGrid was one of the most rewarding, most challenging, most meaningful experiences in my life. The greatest privilege of this entire journey is the deep connections made by working in the trenches with people. Something magical happens when we trust and believe in each other on a startup journey that is impossible to do alone. It took me too many years to learn to raise my hand and ask for help, but when I finally learned to, a village of people came to my support.

I’ll close with the last conversation I had with Antoine, our co-founder and Chief Mad Scientist. I still think about it every day, and I hope it’ll be helpful for you too.

“Life is short.  Take care of the ones you love.  Don’t be afraid to try new things.  Never do anything that makes you unhappy.”

This post is dedicated to my co-founders: Ryan Sutton-Gee, Ralph Gootee, Antoine Hersen, Kenny Stone <3