Tell me a little bit about your early years and where you come from?

Sure, definitely. Well, like you, I took a non-traditional path into tech.

As a child, my father ran a software company, so I was around technology a lot from a young age and really enjoyed it. I hung out at his company a lot. I remember taking a few programming classes in the ’80s – community classes with mostly adults – and it was totally unusual to find a young girl in those kinds of classes. I liked it, but it was just another hobby.

I was progressing through school, I became really interested in science and that turned into an interest in Genomics pretty early. I wanted to be a geneticist, probably a doctor, and that was the plan. So I went to Ohio State, which at the time was one of the best programs for under grads in genetics. That experience got me even more excited. From there, I went into research. My first job was at St. Jude Children’s Research Hospital, the cancer hospital in Memphis, I worked in research for four years, and my plan was to get closer to the work, find out what interested me most and go back to school to get my PhD or my MD and be a research scientist. But when I got into the work, I actually didn’t find it that interesting. I found the subject really interesting, but the day-to-day didn’t stimulate me.

The dot com boom was happening around that time, so Silicon Valley was getting a lot of attention. Programmers and computer scientists were getting a lot of attention. And I remember thinking, “I did that as a kid. It was a lot of fun, and I was good at it.” That seemed like a really exciting career to be in, where there wasn’t this ceiling.

That’s the other thing about research – it doesn’t pay very well, and that really bothered me. I wanted to be in a field where the sky’s the limit, and hearing about all of these entrepreneurs out in Silicon Valley got me really excited.

I didn’t know anyone out there. My exposure was literally from the news. I got really lucky, because this new field was emerging called bioinformatics – basically a merge of biology and computer science. A company called Celera was getting a lot of press because they were sequencing the human genome and racing to make this data available to scientists. It was the Human Genome Project. This project generated an enormous amount of data. This was big data before anyone called it big data, and that data needed to be mined. There was a need for people who could not only understand biology and the data and the science, but also write scripts and programs. That was perfect. I was already thinking about computer science, and now there’s this way I could segue from biology.

I started applying to companies in the Bay Area, Celera in particular. Celera was my target, my dream. I thought that would’ve been the most amazing thing in the world. I applied, I called, I harassed them and applied some more. After a lot of brute-force effort, they hired me, and I relocated from Tennessee to the Bay Area. It was a complete dream job – especially since, by this time, we were in the dot-com bust and not many people were traveling west. I was at Celera for around 4 years working on really interesting and high-profile projects, but I completely fell in love with computer science, so I went back to school in the evenings and got my MS in Computer Science.

Being an engineer in the Valley is a very empowering thing. You identify a problem and write code to solve that problem. It’s very gratifying. I started to become very entrepreneurial. I met my eventual co-founder at Celera, and the time was right for us to dive in head-first and start a company. And the funny thing about it is that we didn’t actually know what we were going to start. It wasn’t like, “I have an idea. I need to go start a company.” It was more, “I need to start a company, and I’ll find the right idea later.” I talk to a lot to entrepreneurs, and they always say, “I don’t know if my idea’s good enough.” And I’m like, “It doesn’t have to be, because you’re going to change your idea 10 times.”

Our first idea that really took off was a company called Spitfire Photo. It was a solution for photographers and, specifically, small, independent agencies around the world that covered global events. We were getting decent traction, but soon realized the market is relatively small and slow growing. We struggled for several years to accelerate it and eventually made the decision to pivot to an enterprise offering after seeing some adoption within organizations. So in 2010, Spitfire Photo became WebDAM. My co-founder and I actually built the first version of the product. There weren’t any other cloud solutions that could do what we doing for enterprises, and it really took off from there. We never raised outside funding, and we were eventually acquired in 2014.

That’s really amazing. So let’s step back. I’d love to hear more about your experience of fundraising and what was disenchanting to you and what fed into that idea of “let’s hold off.”

Right. Well, it was a lot of things. The first investors we approached were definitely top-tier, and we were very early stage and still refining our market fit. There were lots of learnings that came out of those conversations, but it became very clear to us that we should grow the business further before fundraising.

That was one thing, and two – and this is much more clear in hindsight – the Valley was completely male dominated and a very different experience than it is now. Today, being a female in tech is talked about and, as an investor, you have to be aware of the gender disparities and potential biases and operate with a certain level of sensitivity around the topic. But back then? Definitely not.

The other thing about it is – and this is something that I literally just started talking about in the past year, we went 10 years without ever really talked publicly about it – my co-founder is my husband. Early on, when we started the company and people knew we were married, people would say, “Can I talk to your husband?” As if I was his assistant or something! I decided at that point it was not going to define me and became very private about it. Back then, many investors were strongly opposed to investing in married couples.

I can understand that risk, but having a co-founder is like being married. You don’t need a marriage certificate to have disagreements, fights and break-ups – co-founders have fall-out all the time. Interestingly, as more women are jumping into entrepreneurship, we are seeing more and more married co-founders. It’s more accepted. But at the time it was very discouraged, so much so that the second time we started looking for funding I would seek out women investors. That was very unusual for me, because I’ve worked in male-dominated industries my entire life and I’ve never felt like it mattered much. Even when I felt bias, I was like, “Whatever. I’m excited to prove you wrong.” It just never really affected me negatively. But the second time around I said, “I really want to find women investors, because I think they’re going to be more empathetic and open minded.” And in my experience, they were. We were finally well positioned to raise when we started to get approached about acquisition and the conversations changed.

How did your life change as an entrepreneur and the head of a company once kids came into the picture?

I have two kids. My first was born right when we pivoted away from Spitfire Photo to WebDAM. Maternity leave was actually very refreshing. My mind was clearer to think creatively about other options. That’s important for any entrepreneur – to find that space to think clearly. Maternity leave was my space, my time.

I struggled to be a “normal” mom, though. I joined moms groups to meet other new moms and did baby yoga and noon stroller walks. At first it was amazing. It seemed I had a life again. But when it came time for all my “mom friends” to go back to work, I was the only one that did.

Everyone else decided to stay at home, but for me that meant shutting down the business. That was a turning point for me and I started to think differently about how I could combine my loves. Work-life balance wasn’t going to be possible, so I turned to work-life integration. I focused on teaching my son about business and software starting at a young age. I wanted him to know the company, understand it, know what I did, get excited about it, be familiar with it, know who works there. I just wanted it to be part of his life too, because it was clear it was going to be a very important part of our lives.

I have since had a second child, a daughter. And they both walk into WebDAM and know the team by their first names. We have ping pong tables and video games, and they would rather go there than anywhere else after school. Of course, it’s like any other office and we don’t have kids running around during the day, but there are late nights where the kids are having a pizza party while the team is having a hackathon. It has become an important part of their lives, too.

How do you think that experience has shaped your approach to work and your priorities? What about your management style?

It’s tough because I think, for most entrepreneurs, it’s not work. It’s a lifestyle. It’s my hobby, my passion. It’s everything. Even if I wanted to totally separate it or be like, “My kids are going to be my only priority,” it’s still my passion. That was new to me – I didn’t know that about myself. That’s why I think being able to involve them in different ways within the business has become so important.

I actually became much more empathetic to women in the workplace once I was a mom. There was a time when I found it difficult to understand how people could not be 150% invested in their careers – crazy, right? Becoming a mom changed the way I think about other people and how everyone has competing priorities, whatever they are. It’s not my job to judge what should be your priorities, but it is my job to help make it work. That changed a lot for me.

Running a business for 10 years has also increased my awareness and empathy. You come across all sorts of people from all walks of life and start to notice themes. For instance, it became very apparent that women are less inclined to participate in large meetings, always taking a back seat. As a woman CEO, this really bothered me – it’s not like they are the only women in the room? I struggled with confidence myself in the past, but didn’t realize what a systemic problem it was until I managed a large team and saw the staggering differences.

Yeah, and I’m curious to know your thoughts on how do you undo that? When that kind of damage has done over and over and over for so many of these women and other folks who have been in tack and then they come to a company like yours that is better, just because of your experience and you running it, how do you un-train them to actually believe in themself again?

It’s very hard, and I don’t think it’s just from work experience. I think it starts really, really early. At least that was the case for me. Part of the reason it took us five years to pivot was because I had some fundamental confidence issues and an inability to trust my instincts.

Not to be overly optimistic, but I do think it was a bigger issue in my generation, give or take 10 years. I was raised in a society where most moms stayed at home. Our dads were the breadwinners. Men and women held very specific roles. My kid’s generation is seeing a totally different view of women. I’m very hopeful that time will sort out a lot of the unconscious bias. This is why it’s more important than ever for women to ignore the voices of doubt in our heads and forge forward. The next generation is counting on us.

At WebDAM, we started a group called Women of WebDAM (WOW), for exactly this purpose: Come together and support one another. I don’t get a lot of face time with most of the team anymore, and I missed it, so this group provides a way for us to lean on a support network. Sometimes we just go to a wine bar and have wine and talk. Sometimes we’ll do book club, sometimes we’ll go to a networking event or a women’s film festival, whatever it is. But it’s a time for us to get together and have those conversations, and it’s been incredible. Honestly, it’s been as rewarding for me as anyone on the team.

I’m curious: as an entrepreneur, where did you get your resourcefulness from? You jumped from science to computer science to business, and you decided to start your own company and you’re planning to sell to all these clients. What was your process for learning what to do?

Resourcefulness has definitely been a critical skill over the years, as it is for any entrepreneur. I think it comes from a few places. One, I think I am just naturally a problem solver. As a child, the first database I wrote was to categorize my clothing by color and season. It sounds super neurotic now, but it seemed like a totally appropriate thing to do with the Wang business computer my dad brought home from work. I will also say that, even though my parents had traditional gender roles, they were very empowering. There was not a day that went by that I didn’t believe I could do anything I wanted to. And that meant being an astronaut, an actor – the sky was the limit.

My years as a scientist were certainly influential as well. Science teaches you perseverance – digging deeper and deeper into a problem and constantly exploring new untapped avenues.

And last, I have always been relentless in my pursuit of success. I’m not sure where this stemmed from, though I do know that my resourcefulness developed a great deal during the five-year period when we were trying every possible means to accelerate the growth of the business before eventually pivoting.

Where do you see yourself in five or 10 years? Do you think you’ll still be in tech?

No doubt. I love the tech industry. I really love it. I’ll probably either be growing a business or advising and investing in startups. Or perhaps both.

I love hearing other entrepreneur’s stories and being part of a rapidly changing landscape. It’s just a really cool place to be and, being in the Valley, it never gets old and it’s always changing. You’re always meeting someone who is doing something interesting.

Absolutely. Let’s see, if you want to dive into anything else let me know, but my last question to you would be just what major lessons have you learned and what advice would you want to give to aspiring female entrepreneurs?

I think the biggest one that took me a really long time to learn was that nobody knows what you should do. Even if someone has done it before, even if someone has done it over and over again, it doesn’t mean they’re right about what you should do with your company. Trusting our instincts became really important for us. There are so many different ways to achieve your goals in business – ask five people what you should do about a problem in your business and you’ll probably get five different opinions. Every product is different. Every market is different. Economic conditions are constantly changing. So I think it’s important to get really close to your market, really close to whomever your customer is, because that’s when you’re going to be able to develop the instincts and know what to do. You’re the one talking to the customer.