Penelope Trunk, Co-founder & CEO, Quistic, Author, Blogger

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ON MOTIVATION IN JOINING THE IT INDUSTRY

I wanted to make money. I was sick of being poor. I had been in graduate school for English and I felt I dodged a bullet by getting out of academia and into the tech sector.

I was almost always the only woman wherever I worked. And often people assumed I had no idea what I was doing because people assumed women were not technical.

ON THE JOURNEY TO ENTREPRENEURSHIP AND MATH.COM

I came up with the idea for my current CEO to launch Math.com with the company’s intellectual property. I wrote a business case for why the IP would be more valuable in a different company. But I didn’t know I was writing a business case. I had no business background whatsoever.

When he said okay to the idea, I negotiated to buy Math.com (less than $500 at the time!) and I wrote a business plan. Each night after work I’d go to the bookstore and read about how to start a business. Then I’d go home and do next steps, and then I’d bring it to my CEO. I worked like that for five months – having two full-time jobs, until we got the startup funded and he made me full-time at the startup.

ON GENDER BIAS AND WOMEN AS STARTUPS

When you have a startup with investors you have to be all in. That’s part of the deal – investors want things to move fast so they get return on their investment fast.

This is a terrible lifestyle for having children. Most founders with children either have a stay-at-home spouse or a very young child with a full-time nanny. After having done both of those things I have to say it’s not the best way to be close to your child. To put it mildly.

I think of startups as a sickness. Only do it if you can’t stop yourself. It’s scary, lonely and financially ruinous.

ON WOMEN, CAREER AND FAMILY: CAN A WOMAN HAVE IT ALL?

No. Of course not. Both careers and children are about time and commitment. You can’t give lots of time to both. You can’t be hugely committed to both. People who say they do that are delusional.

ON WOMEN AND THE TURNING TIDE: CHOOSING FAMILY OVER CAREER

Women are choosing family over career at higher and higher rates. I think women are realizing that you can work for ten years before kids and twenty years after kids, so you can have a career and kids. You just can’t have them at the same time.

ON ALTERNATIVE WORKING ARRANGEMENT, WORKING FROM HOME: CAN EVERY WOMAN DO THIS?

It means I’m doing both part-time. Parents who stay home and don’t work do more parenting than I do. And people who work full-time at an office do more work than I do. I have half of each. I can’t tell right now if that means I will have two, lame experiences. Or if I will be glad I got to do both at the same time.

For most parents I think it’s BS that they can’t afford this option. I was on public assistance in New York City for two years when we ran out of money. We ran out because I was the sole breadwinner and I didn’t want to leave the house after I had a baby. But I had no idea how to make money from my house

We ruined all our credit. We paid rent late every month. We were scared all the time that we wouldn’t have money for essentials – like medicine, clothes, etc. But in those two years when we had no money, I figured out how to support the family working from home.

It’s very scary to go after the life you want. For anyone. There are a million solutions for poor parents to make staying at home work. People’s sense of how much risk they can take is very low. We lead cushy lives. That’s fine. It’s fine to not want to take a risk. But don’t say you have to work. Say you are too scared to take a risk to stay home with your kids.

ON WORK-LIFE BALANCE

I have nagging guilt every day. This morning my son saw I was doing email and he asked if I’d watch South Park with him. I said I didn’t have time.

Then I said to myself why am I sending email instead of watching South Park?

And then I said: because I like email better than I like South Park. But I want to spend time with my son, and
that’s what he wants to do. And there are some times when I can’t say yes to what he asks, but this time I can. So I watched South Park.

And we laughed together. It’s funny. I told him I’d watch another.

ON THE DEARTH OF WOMEN REPRESENTATION IN THE LEADERSHIP STRUCTURE: WHAT SHOULD WOMEN DO?

I don’t know. Make tough choices. Work ten-hour days. If you want to have representation in a world where it’s all or nothing, then put your all into being part of it.

Or how about voting. I vote. That’s enough for me. We can’t participate in everything. Here’s a question I want to see you ask: How can people, who run the economic and social life in their country at large, participate in changing diapers and wiping vomit at 2am?

ON GENERATION Y AND Z AND WORK-LIFE BALANCE

Generation Y and Z know that balance is not possible. I do a lot of career coaching, and I’m constantly coaching Gen X parents who thought they could have it all and then hit a wall and don’t know what to do. Whereas my coaching sessions with Gen Y-ers are about how to plan for a life where they know they can’t have it all.

ON FUTURE CHALLENGES

I want to be more confident as a parent – self-doubt plagues me on a daily basis. And I want to have more self-discipline about how I work. I notice lots of time during the day when I could get bits and pieces of work done, but instead I space out. It’s very difficult to get work done in fits and starts, but if you parent while you work you have to get really great at doing that.

ON MY WAY OUT, I TAKE…

My phone, a Cliff bar and my kids.

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