Tracy Young Has The Eye Of The Tiger

American Dreamers is a series of conversations with leading Asian American entrepreneurs and business leaders in which they open up about everything from their startup stories and company building to confronting racism and making it in America.

Tracy Young’s story starts like so many children of immigrants’ does: her parents left chaos and violence in their home country, came to the US and struggled for years to build a life for themselves and their children. But Young, an engineer-turned-founder and CEO of not one but two companies, has managed to find success beyond anything her parents could have imagined when they decided to leave Vietnam and settle in the Bay Area.

After a stint at a general contracting firm in the aftermath of the 2008 financial crisis, Young and four co-founders (one of whom is now her husband!) decided to build their first company, PlanGrid. Young eventually became CEO of the company, which totally disrupted the construction industry by allowing engineers and builders to plan and track projects via an app, instead of on paper.

Young and her husband sold the company in late 2018 to AutoDesk; she stayed on a little over a year, and then retired from AutoDesk in March 2020. “We thought we were going to take my parents, the whole family on a vacation. And then I went into lockdown with my husband/co-founder,” she told me during our interview. “And what we did instead was dissect every single minute of the ten years we ran PlanGrid. What that gives us is a long list of things that we felt we did wrong, and a long list of things we thought we did right, and we’re applying all of it to our new company.”

That new company, still in stealth mode, is called TigerEye, and like PlanGrid, it’s geared toward solving problems — this time with enterprise sales teams.

Tracy is so refreshing — she’s got a fantastic sense of humor, she’s straightforward and honest, and she doesn’t let anything get in her way. She’s also determined to share her success by encouraging more women to get into leadership positions, and has been super passionate and outspoken about this issue. Our fun and fascinating conversation, edited for length and clarity, is below.

What’s your parents’ immigrant story? My mom and dad are refugees of the Vietnam War. Wherever the line is between being homeless and just being poor, they were barely above the homeless line. So it was very tough for them to make things work, but they’re super hardworking, super responsible people. It was always about giving a better life to me, my brother and my sister. Growing up, we didn’t have much, we didn’t know what vacations were, but we had a lot of love. What drives me is, I saw how hard my parents work, and I just want to be the best version of myself that I can be to honor their sacrifice.

You know ,the most important decision of my life was not made by me. It was made by my parents, and that allowed me to have the life that I have.

What was your childhood like? I’m a first-generation American. I was the first one to be born here in San Jose. I was very lucky. I grew up in a suburb in the Bay Area. It was very boring, but it was safe.

As a child, I remember my parents working two jobs, and I never saw them, but eventually they opened up their own warehousing business, which they ran for almost forty years. They buy goods in bulk, they mark it up, and then they distribute it to restaurants.

My mom was like the Mafia, in her prime. No one messed with her.

How did your parents think about education? The conversations weren’t really about school. They would more likely be, “Dinner’s in the fridge. Make sure your brother eats,” and, “Don’t smoke pot. Come home before the sun goes down because I’m going to freak out.” It wasn’t about, “Why don’t you get straight A’s?” I don’t think they even looked at my report card.

I was the kid who wasn’t really great at school. I liked playing with blocks. I liked playing on the playground. I actually worked really hard — if I did get an A it was because I worked my ass off. I had friends who could roll out of their bed and pass a test, no problem. That wasn’t me.

How did you settle on engineering? I ended up going to a state school that wasn’t really well thought of. But it was one of the schools that accepted me, and I knew I wanted to be a builder. I thought I wanted to be an architect, but I’m actually not that naturally talented at art, I just like it. I liked buildings and math, and it was very easy for me to choose civil engineering. I knew I could be a good engineer. That was obvious. I liked math enough, but I wasn’t going to be a mathematician, though I ended up marrying a theoretical mathematician, who is also my co-founder for both my companies.

At some point, probably around sophomore year, I realized there were two paths for me. One was to become a structural engineer and sit behind a desk for the rest of my life, crunching numbers and making the math work, or being out on-site, actually being part of the building process and making it happen. That to me was more dynamic and interesting, and I could be outside. I went that route, and I studied construction and engineering management.

How did you start your first company, PlanGrid? I graduated at the worst time to graduate with a construction degree, because construction had the highest unemployment rates, and we were going through a recession and a housing crisis. I was employee number one thousand at a general contracting company, and within two or three years, we were down to three hundred people; I was one of them. It wasn’t because I was a super great engineer. It was because I was probably one of the lowest paid engineers because I was so young.

It was a super depressing time in the industry, and I think it was an easy jump. I’m very frugal; I’d been saving every penny that I’d been making. I’m a vegetarian, and beans and rice are really cheap. My parents wanted to let me live with them, and I could get rid of my apartment. So founding a company, with five of my friends, sounded way more exciting than staying in an industry that was seeing massive layoffs.

Did you have any role models or aspirations at the time? When we founded PlanGrid, it was just this fun project. It was this tool that I wanted to use in the field. Another founder was also a construction engineer; he wanted to use it in the field. It was obvious to us that we were solving a very simple problem — to get rid of all these ten thousand sheets of paper and throw it on a mobile device.

In terms of making it into a viable business, we just lucked out. We were in the right place at the right time, and it was a miracle. Two construction engineers were really good friends with three incredibly talented software developers, and we built PlanGrid.

What did your parents think when you told them you were going to start a company? They were thrilled. They were thrilled that the five of us were starting a company; they knew my friends. They knew my boyfriend, and they were just like, “That’s great. Go!” And they were business owners, too. So they told me, “Yeah, you should be your own boss.”

Plus, they didn’t like that I worked in construction; they didn’t think it was safe. We would end up working crazy hours on a construction site to get the job finished, My parents didn’t like for me to be out on a job site with a bunch of men that late.

How did you end up becoming CEO of PlanGrid? At the beginning, we were all doing everything. And then at some point we realized we couldn’t have five co-founders; you can’t run in five different directions with the team. I can’t have a team member coming to me, not liking what I say, and then going to the other co-founders in the company trying to get a better answer. It was very clear that one of us needed to lead, and my co-founders asked me to do it. At the time I was a reluctant CEO. I have these stories that are deeply ingrained in me, I was thinking, “You guys are older than me. You’re smarter than me. You’re more educated than me.” They eventually convinced me by reminding me, “You’ve been doing it anyways. Go, do it. Go, do the job.”

What were some of the most difficult aspects of being a CEO? What was surprising to you? I didn’t know anything about business. I knew more about HVAC systems and the tensile strength of rebar than I knew about business.

I didn’t know what financial metrics were important. I didn’t know how to deal with super big egos. I didn’t know how to manage people or how to lead people. I was in the biggest job I had ever done and I felt completely out of place every single day. But we were successful because we actually built a really great product that people love to use, and we were able to sell it.

The most challenging days always had to do with something internal at the business, whether there were team members who were just not working out, and needed to be managed out, or really great team members who felt it wasn’t the right place for them and wanted to leave.

The way I dealt with constantly being out of my depths was to surround myself with people way more talented than I am, who can help me, teach me, show me how to do what it is they’re good at.

Your husband is your co-founder. What’s that like? If you have a choice, don’t do it. Don’t complicate your life that way. If you do choose it, you have to know that it can work. That when there are arguments in your personal life about parenting or what have you, or arguments about the business, there need to be clear paths to resolution.

My husband and I are constantly solving problems together. That’s why we know it can work. At least for the business side, there’s a clear delineation of responsibilities. He is technical. I am not. I’m the business person; he’s the technical person. So the decisions are very easy. We rarely fight over anything, because if it’s some technical architecture thing, he’ll run it by me, and I trust him to go figure it out and do it. In terms of anything strategic about the business, or how to spend money, he defaults to me.

Women, and Asian American women, are not that common on construction sites, right? How did you deal with the challenges there? I was a very serious engineer. I would walk onto a job site where people just stared, and it was very uncomfortable, and I didn’t know why they were staring. I’m thinking,“Go do your job.” I’m trying to do my job right? So I didn’t know that I stuck out like a sore thumb. How did I handle it? I was just laser-focused on work.

In terms of having women in leadership, that’s a different story. Intelligence, hard work, leadership. It’s equally distributed across genders. It’s equally distributed across race, ethnicity, age, all of those factors. But when we look at leadership, and it looks predominantly one way, then there’s a massive problem here.

There are not enough women in leadership, and the first step to change is acknowledgment. So let’s talk about it. Let’s talk about VC funding. In 2021 female founders received only two percent of venture capital dollars.

I’ve definitely been in rooms where I give a presentation, and then all of the questions go to my male co-founder. I’m thinking, “Wow! Did I not just give you a whole presentation about the business? You can’t even look me in the eye!” I think it’s a systemic problem. I think it starts at childhood; I think it’s part of our cultural history, the way we treat women and girls, and the words we use for them.

If you are an ambitious, hard-working person who is not happy with the world, with the products, with how workplaces function, step up to the plate. Be the change that you want to see. That’s what I’m doing. And, look, you can have a lot of fun while you’re doing it. You can work with great people, because now you’re the one choosing who your team is.

You’ve started two successful companies; you’ve probably fulfilled your own dreams and your parents’ dreams for you. What are your dreams now? I dream about being a good mom. I have three young kids. Every day these kids find a way to test me on that front. So that’s the number one dream: not mess them up and let them be the creative little pure creatures they are. Number two is to be a good example for the next generation of women leaders. If even one woman starts a company because of me, then it’s all worth it.

What do you love about America? Okay, look at how I look! I’m a petite Asian female. I got to work in construction. I got to lead people. I got to found a company. I got to build a company. I get to build a second company, and I just don’t think I would have had the opportunities I had anywhere else.