What It’s Like to Be a Woman in Venture Capital

Ann Crady Weiss, an entrepreneur and venture partner in Silicon Valley, talks about being a female executive in tech.

Ann Crady Weiss  (Rebecca Clarke)

The venture-capital profession is less than a century old, but it controls a lot of investment capital—peaking at a record $63.3 billion in 2015, though that number is predicted to shrink this year due to a volatile stock market and fears of a tech bubble.

It is widely known that women aren’t well represented in founding or partner roles in the startup investment space: According to Tech Crunch, only 7 percent of investing partners at the top 100 venture firms are women. Most of the funds that come from these VC firms go to companies founded by men, and when women do get funded, they get less: A Bloomberg examination of 890 startups that received at least $20 million in VC funding found that women founders got an average of $77 million, compared to $100 for male founders.

Ann Crady Weiss is the founder and CEO of Hatch Baby, a start-up nursery device company in Menlo Park, California, as well as a venture partner with True Ventures, a VC investment firm. For The Atlantic’s series of interviews with American workers, I spoke with Crady Weiss about entrepreneurship, how she manages work-life balance, and the pushes for diversity and parental leave in Silicon Valley. The interview that follows has been lightly edited for length and clarity.

Adrienne Green: What influenced you to start working as a venture capitalist?

Ann Crady Weiss: I really have three jobs: the CEO of a startup company called Hatch Baby, a venture partner with the True Ventures firm, and then a parent and wife. I've been an entrepreneur for the last 10 years; I've started two companies, and been on the founding team of another. I was drawn to the venture capital side because it's a lot of fun getting to hear about exciting things, to be on the cutting edge of innovation, and to meet very smart and motivated folks who are interested in starting companies.

There are probably three parts: hearing pitches, helping companies that we've invested in, and then the internal workings of True Venture. The most fun part is hearing the pitches, what people are up to, and learning about areas that I know nothing about. Recently, I heard a biotech pitch, and I am not a scientist in any way, but I got to do a ton of research to learn whether this was worth spending a ton of time and money investing in.

Green: How do you evaluate whether someone’s idea is strong enough to invest in?

Crady Weiss: Number one is the entrepreneur has to connect with me, and I have to connect with the entrepreneur. I think much of life comes down to human connections, and that's a really important part of investing. You have to make sure that whoever is investing in you is someone that you get along with, and who you have a shared vision with.

The next criterion is the area that an entrepreneur is focused on. Is than area that I am going to be excited to hear about? A lot of the stuff that's interesting to me is consumer-based. I'm not a scientist or a technologist, but the products and services that I can see as an individual, as a mom, as a working professional, are the ones that have to resonate. Then lastly, because we invest so early on, we have to see that the idea has the potential for return.

Crady Weiss: I don't believe that venture capitalism is impersonal, or it's only about money. The reality is that there are a lot of different venture capitalists out there, and there's a lot of money-seeking companies that are interesting. And so really to be good at it, you have to be differentiated. Clearly, money is money, but the human connection matters, and being passionate about a space matters. You want to make sure that you're asking a venture capitalist for the most important things. In my experience as an entrepreneur, there's no question that there's massive value beyond the checks.

Green: What are the challenges you face by being involved with businesses in their early stages? What happens when an idea falls flat?

Crady Weiss: We invest extremely early. We are likely to be the first professional money in [as opposed to friends or family], and obviously there's huge risk involved. We are totally okay if things don't work out. Certainly, we hope every investment becomes a FitBit, but not everyone’s idea does.

What we invest in is people, and relationships. We may put a couple million dollars into your first thing, and it may not go the way you wanted it to go, but what we do is we develop a relationship with you. We get to know you, and we hope that you will come back with your next idea, and with your next idea, and with your next idea.

Green: What's an average day like for you, trying to manage your many jobs?

Crady Weiss: As a working mom in particular, life is crazy, but I feel so lucky to have the job that I have. Between 10 and 20 percent of my week is devoted to True Ventures related stuff: hearing pitches, talking to one of my partners, or interacting with a company. Then, the overwhelming majority of my time is still spent as the operational CEO at Hatch Baby. In my non-working hours, I am a parent and a wife, and a person as well. My day-to-day is super busy and are definitely times where I feel overwhelmed, but the really fantastic thing is that I love what I do, and I know that's a pretty unique thing.

Green: You described your life in three compartments. Do you look at your life as blended parts of your life or do you work to separate them?

Crady Weiss: I'm definitely more of a blended, "Hey, what's on fire right now? What do I really need to do right now?" kind of person. That's just the way life is. There are times when certain things just need more attention than others.

I have experienced times when things are not going well in one of those three components of my life, and it affects everything. If something is going wrong on the homefront—I have a three-and-a-half year old, and if she's having a hard time, which she did about six months ago—it affects everything. Finding a balance and getting as happy as you can, or as authentic as you can, each one of those experiences has been really important for me. Taking care of myself in all three components of my life is really important to be happy in the others.

Green: True Ventures just announced that it closed its fifth fund with $310 million, and you’re the first female entrepreneur that they’ve tapped as a venture partner to help run it. What is the impact of decisions like that for women in Silicon Valley?

Crady Weiss: I have a very long relationship with the company, and they asked me to do this venture-partner thing not because I'm a woman, although I think that certainly helped, but because I have been involved with two of companies they invested in. I think also, they respect me and the different perspective I bring to the table.

Green: Do you see that happening in other areas of the tech industry?

Crady Weiss: I definitely see it shifting. It's hard in America to talk about gender and race, but I think that the venture-capital industry absolutely has its heart in the right place, and really would like to diversify. Whether that's diversity in what your professional background is, what your gender is, or what your race is, I think the firms are really recognizing the importance, not for PR purposes, but for the bottom line. When you have diversity around the table, research has shown that that leads to better outcomes. Venture capitalists are self-interested like the rest of us.

Crady Weiss: I'm really encouraged about what is being done. I think what needs to continue are we need to continue to have conversations about the importance of diversity. We need to continue to hire excellent people—regardless of their race or their gender, and not just people that you know, or that you golf with, or that you went to school with—that is really important. I think it's happening, and I think it is continuing to happen.

Green: Your husband is also a tech executive and co-runs your business with you. What is it like working with your spouse?

Crady Weiss: My husband is my co-founder. I'm the CEO and he's the CTO, but we do make almost all major decisions together, as do many co-founders. It definitely adds a level of complexity to have your co-founder as your husband. The reality is you have to be very disciplined about making sure that work decisions stay at work, and that home decisions stay at home. It’s important to be very diligent about our communication as a couple, to make sure that any conflict that we have at work is put in check.

On the positive side, it adds incredible trust. My husband and I are very different people, both in our personalities and also in our areas of expertise: He is technical, he's deliberate, he's organized, he's diligent, and I am much more idea-, excitement-, possibility-, and vision-oriented. The plus side of being so different, and also being so connected as married couple, is that we trust each other.

All of that said, it's not without difficulty. If I were to fund a married couple, or frankly, any co-founder relationship, you really want to make sure that you have clear lines of responsibility, and that you also have individuals who can effectively communicate, and that you have a plan for if they cannot effectively communicate, and an alternative, what you're going to do in case it doesn't work out.

Green: You’ve written previously about the need for better parental leave in the tech industry. Tell me more about that.

Crady Weiss: It's a personal passion, for sure. I believe that we should provide parental leave, period, and I believe it should be paid. We need to normalize motherhood and make it parenthood. Silicon Valley and these high-profile companies are doing a great job with parental leave. I applaud the Facebooks and the Netflixes of the world who are paying their folks leave, both dads and moms, but the challenge is it really leaves the low-wage worker out. Those folks just happen to employ high-wage workers. The challenge is that everybody deserves that sort of support. It shouldn't just be for rich people.

Now, all of that said, I run a very small company, and I can't afford on my own to say, “Everyone at my company, here's six months paid when you have any event.” It's a really, really hard thing financially to ask a company to do. For me, I actually think it's incumbent on our government leaders and our industry leaders, to get together to figure out how we can both normalize for gender and support working families. I think it's really important to do, but I also recognize how difficult it would be for individual companies to take that on entirely on themselves.

Green: How is your work tied into your identity?

Crady Weiss: My work, for good or bad, is my identity. That's where I spend all my waking time, so I have chosen things to do with my time that I really value, and to the extent that one of my jobs or if some part of my job doesn't meet that threshold, I know that at that point, it's time to make a change. There's one job that I will never give up, being a parent, and being a wife, and being myself. None of the things are things I can, or want to, run away from.

The reality is I've had other jobs in my life where you do get to the point where you think, "It's really eating me alive." I am really lucky to have a background that has afforded me the ability to make changes in my career, and to try new things.

I don't think that there are any rules. I think it's really important that you check in with yourself, and you figure out what makes you happy. Will you be happiest as a full-time mom? Will you be happiest as a full-time working professional? Will you be happiest with some balance between the two? I think it's really important to be sufficiently in touch with oneself to be able to make that decision.

This interview is a part of a series about the lives and experiences of members of the American workforce, which includes conversations with an investment banker, a software engineer, and a stay-at-home mom.