Gail Wonghas advised businesses on finance, strategy, talent, and peak performance since 2001. At Morgan Stanley, she served companies like BlackRock, CIMB, Legg Mason, Netezza, OCBC, TechTarget, Siemens, and Temasek. She led diverse teams across Asia, Europe, and the United States, and successfully executed M&A and financing deals worth more than USD 10 billion through market peaks and troughs.

Gail Wong, managing partner at Her Capital

KrASIA (Kr): You swam with sharks on Wall Street, and now you’re a managing partner at Her Capital. Tell us more about your career path and how you’ve navigated different waters. 

Gail Wong (GW): My decision to work at Morgan Stanley was about excellence. I loved learning about deals and working alongside the best in industry. But I discovered there was a dark side to excellence. It’s a cutthroat environment.

The system produces certain types of winners. In western countries, the winners were white men. I was rare. I was one of the five women and non-white people in my team of 50. In Asia, it’s a bit more diverse, but it’s still clear who’s “in power.” As an associate, I was already pushing for diversity.

There are certain expectations about how women need to behave. If you are hardworking, you also have to be nice. For a woman, you have to find other ways outside of work to connect to the people that you want to cultivate as champions and allies. I learned all these lessons, like talking in a low voice. But then I was like: Why do women have to go out of their way to do that? There are so many bright people with different takes on solving problems and the world misses out on this opportunity if workplaces aren’t spaces where all can thrive.

I’ve had a career in finance, but I’m also keenly attuned to what it means to be an outsider, and why it’s important to bring outsiders into the mainstream and benefit the world.

Kr: How did you find yourself fitting into male-dominated industries?

GW: I’m naturally more of a listener and observer. Even in my third year as a senior analyst, I got feedback that I have great ideas and do the work, but why am I not using that to leave an impression on clients in a meeting? Women tend to measure themselves quite critically. They don’t speak up until they know for sure what the answer is, so that they have the best answer.

There are some cultural expectations. When you promote a woman, people ask if she’s going to get married or have kids. I think it’s a little less exclusionary in Asia. Because of the social structures, perhaps, it’s more common for women to work. But in the States, I found it baffling, until I actually became a parent and I understood the responsibility – and that the care predominantly is done by women.

There economic system in industries is completely counter to care-giving. You have to sharpen your knife, put on your game face, and go into work. Corporations need to make life work for their employees, because its good business sense. I’m sure there are dads who want that too. We can talk about how challenging it is for women, but I think there’s also very little flexibility for expectations around men. They’re two sides of the same coin.

Kr: Did your identity as an Asian woman impact your behavior in the workplace? 

GW:I went from Asia to New York, so there was already this Asian identity. I’ve never been the loudest voice in the room or the one who talked the most. And then I decided to be a diversity champion. In hindsight it might have been perceived as “career suicide” to build on pre-existing stereotypes; I just did what I felt was important.

I’m always curious about how different I could have been if I had a different mindset changed earlier in life—to just really be fearless in meetings and not worry about what I said.

There was a funny contradiction. On one hand, I totally set my terms. I asked to work in London, then Singapore, New York, and Boston. I switched from financial services to technology coverage. I asked for all those things without even second-guessing myself. But when it came time to negotiate my exit, I thought, “Should I even negotiate? Maybe I can be okay with whatever I’m offered.” But a male colleague of mine made a comment about the offer and said, “This is totally insulting.” Thinking back, I would have liked to have a clearer idea about my worth.

Gail delivering a Ted talk: the power of our financial mindsets to change the world. Courtesy of TED.

Kr: What is a translatable lesson from your investing career that can be shared with the women entrepreneurs who you are funding?

GW:There’s this concept of ikigai. It’s a Japanese word, but there are basically four overlapping circles: what you’re good at, what makes money, what the world needs, and what brings you joy. I spent my first 20 or 30 years doing what was expected of me. That hit two of the circles, and sometimes the third. But I had a deep inquiry into what I planned to do for the rest of my life.

A lot of female founders tend to be passionate, so they come from that purposeful lens. There’s a journey in terms of integrating those pieces with risk. Any time there’s a big leap of faith, there is a big risk as well—financially but also reputably. As leaders, we have to find a way to belong to yourself first, in the face of uncertainty. I suppose you can call it the soul of the business. I do think that’s the X factor in a great business plan and thriving in entrepreneurship.

Gail Wong as a panelist at the WeConnect’s Inaugural Supplier Diversity Summit. Courtesy of Gail Wong.

Kr: How have your personal experiences influenced the gender lens of Her Capital?

GW:Innovations for women are poorly understood. I’m really excited to back products that are going to make life better for half the population and are designed for people first, rather than with a default male in mind. This has huge implications for female health, but also care-giving for our aging population.

Gender lens investment [which takes women’s well being into account] is in an evolving state. Her Capital’s primary thesis is female founders of firms and that has knock-on effects to addressing women as consumers and employees. The last bit of it is really integrating the gender lens in our investment process: being aware of biases, working with an individual, and having a diverse investment team. Female founders are excited about having a diverse investor base that can be supportive, that they feel an affinity with. Women investors tend to want to roll up their sleeves and ask how they can help, to weigh in and open their networks.

Gail Wong as a panelist at the WeConnect’s Inaugural Supplier Diversity Summit. Courtesy of Gail Wong.

Kr: As more women become entrepreneurs and investors, what are your expectations for the VC world?

GW:Broader perspectives and selecting businesses that are going to shape our future. Funding is one way to supercharge the company, broaden their reach, and help them create better products. I want to think of VCs as something more than what make a few people rich, but also moves humanity forward. These are cutting-edge innovations that will change our lives.

I’d love to see the world shift not just in terms of representation, but also in terms of mindset. I want the world to recognize that we are far below our potential if we don’t include diverse perspectives. That is better for both women and men. It shows up not just in having women entrepreneurs and VCs, but also in how we evaluate our investments to take into account both the easily quantified (in dollars and data) and not-so-easily or impossible-to-be quantified.

Disclaimer:This article is part of our “Tuning In” series. All answers reflect the personal perspective of the interviewee herself, and not KrASIA’s. If you’d like to contribute as a writer or nominate someone for our “Tuning In” series, you can contact us at community@kr-asia.com.