I would like to start from the early years and where you come from. Can you tell me a bit about that?

I’m from New York. I was born in Brooklyn, and lived there until grade school then my parents moved to the suburbs. I grew up in a suburb called Great Neck, which is a predominantly jewish suburb.  Lots of doctors, lawyers and business people – the proverbial golden ghetto. I went to a good high school, and my family really focused on academics. Music was a big part of my life—I studied music very seriously and thought about going to a conservatory but I didn’t love it enough to only do music. I’m the oldest of four children. Both my parents are doctors. Interestingly my mother always worked, as did my mother-in-law, actually, my grandmother also worked outside the home as a teacher.

I went to Dartmouth and majored in Government. My career goal was to be a diplomat or work for the World Bank or IMF.  After Dartmouth I got my master’s at Georgetown in International Relations and took the Foreign Service Exam, so I was on that path. I worked for the Agency for International Development when I was at Georgetown and realized that I wasn’t suited towards working for the government so I switched gears and went to get my MBA.

Backtracking bit on the personal side, my husband and I both went to Dartmouth. We met on a Government department foreign study program. We got married right when we graduated from college which I suppose is a little bit unusual. In fact I was 20 when we got married. Steve worked in DC while I went to Georgetown and then we both went to Harvard Business School together. My oldest son was born while I was at Georgetown, also a little unusual for my generation. I always knew I wanted to have children and I didn’t particularly want to wait, and just assumed I’d work while I had my children so we started our family young. My oldest son went to Harvard Business School daycare and I got pregnant with my second son when we were in business school.  We decided after graduating from business school that we’d come to the bay area because he was from California and I wanted to work in tech so we moved out to the bay area in ’88. I’ve been working in Silicon Valley since then.

My first job was at Informix—a database company—competitor to Oracle. I was there six years—four years in marketing, then two years in Latin American sales. I’ll come back to that as it’s—probably one of the more interesting things I did. Then I worked for another database company called Gupta, then consulted for a little while and then joined Netscape post-IPO, that was 97. I was at Netscape for six years, ended up running the browser division for the last two years there. I joined before the AOL merger and stayed through the AOL and Time Warner merger craziness. When AOL decided to get out of the browser business, I left. That was ‘03.

I went to Yahoo where I ran Yahoo Mail, was at Yahoo for a year—and Yahoo was getting very big and bureaucratic.  I thought I want to try a startup and I went to this little company called Metalincs that did e-mail analytics. I was their VP of marketing, launched the product and we got bought by Seagate.  I went to work at Check Point where I ran their consumer business and was VP of marketing. Check Point is one of the major security technology companies.  I realized that I’ve run businesses several times and was actually ready to run a company.  

I joined SugarSync at the end of 2008—right when the market was collapsing. SugarSync was really a great concept and the founders had tremendous vision, but the company at that point was in crisis – the debt holders had taken over and they had run out of money.  I came in and did a restart. The company had had no revenue at that point and was down to 13 people.  I grew the business from there about 75 people and a 20-million-dollar run rate over 4 years.  We had millions of users and terrific reviews.  We had multiple offers to buy it up to nine figures.  The board didn’t want to sell so we agreed to disagree and I left.  Later in 2013 I joined a company called Catch.com as CEO.  I later sold that company to Apple.  I had twice joined existing start-ups and thought if I’m going to do this start-up thing again, it would be better to start my own. I started researching some different start-up ideas I was interested in, did a little bit of consulting—I needed the right product and the right people, and those two things came together about a year-and-a-half ago and we started Context Engines.  We’re now beginning to test our product with the earliest users, and hopefully we’ll launch it in a couple months.

Back to the personal side, I have three other children that were born here in California. I was pregnant with my second son in business school, but he was born at Stanford. My kids are 20 through 30. My oldest son lives nearby, they have a three-year-old and they’re expecting a baby girl in March. It’s coming full circle and I’m so enjoying being a grandmother.

I mean, gosh, you’ve walked me through a very extensive impressive career really quickly, but kind of digging into that specifically, of all the things that you’ve accomplished, between is saving companies, building companies, selling companies, what have been the proudest accomplishments of your career?

Well, I’m very proud of what I built at SugarSync. I took a company that was on the brink and built a pretty substantial business. Unfortunately, I didn’t get to exit it so while I’m proud of what I did these things are evaluated by the end outcome and the CEO after me was not able to grow the business and sold for a modest amount. I’m extremely proud of the work I did at Catch—I achieved a really excellent outcome for the investors in just six months.  On the product side I’m very proud of the work I did at Netscape. I was promoted to VP right after Netscape 6.0 shipped. Netscape 6.0 was a pretty bad product—I pulled the team together over the following six months and shipped Netscape 6.1 which was a good product. I look back over a lot of different products I’ve worked on that I’m proud Netscape 4.5,  6.1 and 7, Yahoo Mail, Metalincs. And then I’m very proud of the teams I’ve built. I’m fundamentally a people person, so I really love that part of the role.

I’d love to hear how fundraising and building a business was while raising multiple children.

Let’s see. Where do I start? When I interviewed for the SugarSync CEO role, my youngest son was 12. I didn’t have babies at home. And in fact when I interviewed for the position, one of the board members actually asked me, “how are you going to do this job while you have children?”  I’m not sure how it would have worked to do the startup CEO role when my children were small. I had very big jobs while I had babies—I had a VP job at Netscape managing a team of 220 people, but I didn’t have the stress of being CEO. But I have always felt like having the experiences of being a parent gave me confidence. It gave me a sense of maturity, a way to deal with people. I do believe fundraising can be tricky for women.  I think actually the irony is a lot of the investors want to be open to women CEO’s– they don’t want to be biased. They think of themselves of liberal, even-handed people yet they’re just not used to women CEOs. When they do the classic pattern-matching, women don’t fit the pattern. So I do think it is challenging for women. That being said, it comes down to having a compelling business, having a compelling story and pounding the pavement. Bottom line I was able to raise money—multiple rounds. I see other women raising money despite the extra challenge.

What are some of the other challenges that you faced?

Well, child care was always a challenge. Generally I was not conflicted about, “Do I want to work?” I liked working. I wanted to work, but if our nanny quit, I was the one typically who would stress out. My husband somehow rolled with it—it didn’t get to him as much. I think with those things women tend to be the ones who are where the rubber meets the road. Childcare is really hard. It’s expensive. When you’re early on in your career, the expenses is pretty significant, and finding someone that you can trust—we definitely had some bumps there, and if you have to travel it makes it even harder. I did a fair amount of travel in my career. I was lucky that my mother-in-law lives about 90 minutes away in Stockton, and so while it was too far to do the day to day stuff, if my husband and I were both out of town (which we tried hard to avoid) she typically would come. I was lucky to have family support otherwise I don’t know what we would’ve done. We would’ve figured it out but business travel makes it challenging.

I just have a cat, and I feel the burden of traveling a lot [chuckles].

We have a cat too.

Oh yeah?

I’ve never been a pet person, however, when we moved in 2003, the kids made us feel so guilty that we were ruining their lives by moving and making them switch schools that in a moment of weakness I agreed to a cat. And now my kids are off in college and I still have their cat.

How dare they.

And she’s not even a good mouser.

Well what’s the use of that?

She’s cute. She’s a cute cat.

You as a sum of all of your life experience and your background and your four kids—how do you feel like that affects the way you approach your work and kind of what you bring to the table?

One of the biggest lessons you learn in parenting is to separate the behavior from the person. All kids misbehave, and parents need to guide them to behave appropriately. But you need to separate out I love you from I don’t love the fact that you wrote on the wall or didn’t obey the curfew etc. Fundamentally a lot of managers in the business world aren’t good at that. They do a poor job of giving feedback because they don’t make that separation.   “Hey, you’re smart, you are a really good employee, but next time you do a project like that here’s how you need to do it differently.” I think that’s hard for a lot of people yet it’s one of the more fundamental parts of management. I also believe just having my children kept me grounded and balanced. What I notice now that my kids are out of the house, where—typically I don’t have my kids around in the evening I no longer have a forcing function for me to shut off work.  I recognize how much my kids helped me keep a more reasonable balance—it  was a good thing. Now I have to develop alternative mechanisms.  For years when my kids were little I tried to shut work off from 6:30 to when my kids went to bed—I would try to be pretty vigilant unless it was an absolute work emergency to focus on the kids. People talk about work-life balance and I think that it’s healthier. For me, I can easily get overfocused on work—I’m the type that I would get more consumed with my work, probably to an unhealthy degree when I’m passionate about what I’m working on, so it’s healthy for me and my family to be not so one-sided.

I can relate in a different way. Just starting this year, to learn of the value of taking little breaks. I had to do it through meditation, but it is a life changer, honestly.

It’s funny you mention meditation, but I started when I was CEO of SugarSync.  SugarSync was exciting, but it was very stressful.  A couple of times we had very little money in the bank account when I was fundraising, and so there’s definitely a lot of stress there so I did this mindfulness-based stress reduction class. I don’t know if you’ve ever heard of the MBSR, it’s basically meditation class. I found it to be very helpful. I should meditate more often, my life right now isn’t quite as crazy, but I think it’s a really great tool.

What other disciplines, or life practices did you discover over the course of your career that made it possible for you accomplish all that you have?

At that same time at SugarSync, I started working out more regularly in the early morning. And actually, I can send you a link. There was an article on the Wall Street Journal about me doing this morning hike routine with some girlfriends, and it was a two-fer because I’d get the exercise which would clear my head. And frankly, I’ve always found outdoor exercise to really be much more of a stress reliever, head clearer. If I can’t do it outside, I’ll go to the gym and that’s helpful, but when I can, my favorite thing to do is to hike outside. Ideally with friends, and so it’s social, but if that doesn’t work out schedule-wise, I’ll listen to a podcast or listen to music, or just enjoy nature. And that’s one nice thing living here, one minute from just beautiful places to walk.  It’s amazing.

And I’ve always kept up my friendships, my girlfriends. I have more time now for that then I did with young kids at home—we hike with them or try to meet for lunch or coffee.

You were lucky to learn early on that other things matter. And taking care of yourself matters. And things other than the product, like exercise, friendships, the people in your life. I think a lot of folks take a lot longer to learn that here. I learned after I worked in tech.

I think because of having kids from the beginning of my career always had a life outside of work. And I think I’ve always been a social person. The exercise piece for me, it took ‘til about I’d say my mid-thirties for me to enjoy exercise. But now I love it, like I said, especially if I’m outside. And now I’ve gone back to my music and that’s something that with kids at home there was just no room in the schedule.  I didn’t play violin literally for about 28 years, and I’ve picked that back up about a year and a half ago. I’m enjoying that very much. I’m not as good as I use to be but I’ve made peace with that fact and am improving with practice.  I also enjoy the social since I do chamber music, that’s been fun.

That’s really neat, it’s nice that it’s all coming full circle.

Yes, the violin thing was something I had a mental block on, and I actually just wrote a blog post about that a few weeks ago.  I kept on putting it off because I didn’t like how I would play. I had set this standard for myself and then wasn’t playing because I knew I wouldn’t be above that standard. And then I finally realized, well it’s not going to get any better and I’m just missing out. When my youngest son went to college I realized if I don’t do it now I’m probably not going to ever. And so I got over that hump.

I grew up playing classical piano, competitively. I’m sure you can relate, practicing like four hours a day and it’s your life and I quit when I went to college, and wasn’t competing anymore so I didn’t see the point.

Okay. So then, you totally understand.

I have the same issue where I can’t even touch a piano, because just the pain of knowing that I can’t produce the perfect thing that I use to produce, so what’s the point.

I did those competition things with violin. We had this thing in New York called New York State’s School Music Association, where you’d go and play for a jury—chose a piece, and it would be at a certain level, and you’d get graded. So the highest level of pieces, I think was six or seven, and I was playing at that level when I was a junior and senior in high school. So, the piece I was playing when I picked it back up, and not playing easily, I think was a four or five. I don’t know if your music teacher did this, but you’d work on a piece of music and then they’d put the date, and say like, “For next week’s lesson, learn this movement or learn up to this repeat,” so I realized last spring, I was working on something I had worked on in seventh grade. I regressed a lot but I have some things I feel like I do better but the technique is not the same.

Yeah.

But, you know, I just decided to get over it.

It’s what you have to do.

I’m curious now, because I know how growing up with that discipline has affected me in good and bad ways in my tech career, which in so many ways is the opposite discipline of classically trained music. So, I’m curious to know how that upbringing—a rigid, strict, music upbringing (with perfectionist aspirations, because that’s built into it) affected your approach to your work, for good and for bad.

I’d say on the good side, it makes you appreciate diligence and working on things, especially things that sometimes come slowly. Even if you have a lot of talent, learning pieces, perfecting it, it’s sort of a day-by-day, little-by-little process. So just I think having that self-discipline and diligence is what I got out of it. But the perfectionism is dangerous, and I sometimes suffer from that. [chuckles]

The technique that my husband has tried to get me to use is, “Okay, you’re not satisfied with this. That’s fine. You have your own standard. But, if you were looking at this as a third party, how would you view it? What grade would you give yourself on a 1 – 10?” And if I really put myself in that outside shoe, I think I’m actually fair. I’ll say, “Okay, it’s a seven. It’s an eight. Whatever it is. This marketing campaign, you know what, it was pretty good,” But because, for me, when it’s not a 10, I can be very hard on myself. But I wonder if that was caused by the music or if people like you and I gravitate towards classical music, or survive through the years of classical music, because we have that. And the people who are just always going to say, “Oh, seven or eight’s pretty good. Those are the people who quit, because a lot of people quit classical music. The cause and effect of this whole topic I’m not clear on.

Yeah, it’s a big question.

I would suspect that is part of your current work too. That you go the extra effort to get the lighting and the setting, to get it all perfect—it’s like that extra diligence.

For sure. I love that we’re having this conversation.

You’ve seen tech through a couple of cycles and I’m curious to know your thoughts on where it is now, what excites you about tech, and what frustrates you about tech.

What really excites me is with the modern tools how quickly we can build interesting, useful things. My current startup, we’re two engineers—my two co-founders—and myself. Of course I wish we were going faster and that we shipped last but we’re able to leverage all these great tools in technology and build a lot quickly. That’s very exciting and satisfying to me, just the technical progress that we’ve made and the experiences we can offer. That really excites me.

What else? It has this—and I’m not talking like the unicorns and stuff—there’s a little bit of the gold rush mentality, where I feel like because tech has gotten so exciting, people who really aren’t truly passionate about it, it’s the hot thing to do. Just like when I finished business school in ’88, not that many of us came into technology. You had to be really, really interested. Most people were doing investment banking or consulting out of Harvard Business School. By the way, some of them loved finance and loved management consulting and were great at it, and some people were just the, “Well I’m going with what’s the hot, popular thing.” We’re getting a lot of people in tech here in the Bay Area who I think are doing the hot, popular thing. That is distracting. It makes for some junky stuff in the system. Even so it’s still, to me, just very exciting. What we’re able to build.

I wish we had made more progress on things like diversity. I’ve been here long enough to see that, no, we actually haven’t. It’s the same, or it may be slightly worse. That shouldn’t be. Other fields have made progress. When I graduated from college in ’85, med schools were 75-25, they’re 50-50 now. Our industry’s poor diversity is frustrating to me. I’m trying to do my part on that. Not just on the gender front, too. I read this article about Howard University—that they’re having trouble getting the Silicon Valley firms to recruit there, at their CS department. There’s no excuse for that. They claim they want to hire more people of color, then go there. I’m sure there are great students. I wish we were making more progress.

For me, technology is still just super exciting. One of the things I’ve always loved is how much variety I’ve had in my job. Most of the people in my family are doctors, and medicine is a great career, but I think what you do doesn’t change as much. It’s very important work, and I think it’s satisfying, but for me I like the fact that there’s been just so much change over, you know, what I do. For instance, in 1988—my first job was was as product manager in Informix, we did all these trade shows and seminars and data sheets and sales calls, and I just think about how the marketing discipline has changed, how technology has changed… it’s very exciting. So I think I would have been bored elsewhere. It’s never boring here.

Yeah, I agree. What sort of advice would you have for women in tech, or women entrepreneurs, or even mothers in tech based on what you’ve learned?

Good question. One piece of advice I’ve given people is, I wish I had gone to the startup world sooner. I think I perceived it as being very risky, but there’s risk anywhere. You could be at Yahoo now and chances are you’re worried about getting laid-off. You might as well be in a startup where you have more control over your destiny, there’s more transparency. Nothing wrong with big companies, I worked for big companies for 20 years, but I’ve enjoyed the startup world more.

Also, if I’m asked I always tell women not to wait to have kids. You never know. There will always be jobs but biology doesn’t wait. I’ve just had friends with a lot of disappointments and struggles. Those decisions are harder to change or undo. You can always find a different job. If you’re confident, you’re hard-working, I think that will work out.

Most importantly, If you’re planning to work and have kids, you need to really make sure your partner is committed to that. I’m very fortunate my husband and I feel like really we’ve partnered over the years, on the kids and the household stuff, and we’ve supported each other. We have different things we have done for the family, but I really felt like it was a shared enterprise.

Take the longer view—actually Sheryl Sandberg writes about this pretty clearly in her book. Let’s say you’re in your late twenties, so you’re relatively early on in your career, and you have a toddler and a baby. Childcare is going to be expensive, and because you’re early on in your career, maybe you don’t make that much more than what the childcare costs. It’s easy to look at that as, well then maybe I might as well stay home. But you’re looking at current income and current expense, and you really need to look at it with let’s say a 20 year future view. And your current childcare expense is an investment in your ability to earn income 10 years down the line. And I think when your kids are that age and you’re not sleeping, and you have maybe an annoying boss and whatever else is going on, you feel like it’s always going to be that way, but kids actually don’t stay babies for very long. It seems like when you’re in that sleepless state it’s going to go on forever. Let’s say you have two kids and they’re three years apart, after eight years everyone’s in school full-time. Maybe after three years kids are in school part-time, and it starts to be more manageable. I think it’s important to sort of step back and take the longer view. I had a lot of friends who dropped out of their careers at the baby stage and now they’re not quite sure what to do with themselves. When your kids leave for college I think it’s a tough stage and it’s really tough if you don’t have either a career or some kind of intense volunteer interest.

Yeah.

That being said, everyone has to do what’s right for them. I try to be careful not to be too judging—I mean, it’s a personal choice right?