‘I think a lot of investors are intuition-based — they just won’t admit it’
A Leading by Example interview with Andrea Barrica, venture partner at 500 Startups, serial entrepreneur, award-winning pitch coach, and self-described #EmpathyWarrior.
Topics discussed: What “the diversity conversation” leaves out | Getting comfortable with grey | Aspiring to be computers | Being ruthless at doing good | What to do when you’re the only empath in the room
Read the introduction to this series here.
Miki: What does feminine energy or power mean to you?
Andrea: I think of it a little bit like neck down vs. neck up thinking. Leading from the feminine is really about intuition. It’s less about the “what,” and more about the “how.” When I am leading from the feminine, I feel like I’m in tune with the relationships between people. I also think it’s about valuing emotions, how people feel and relate to one another, over just the facts or the bottom line. I see it as more collaborative and trying to find a common goal instead of figuring out how to beat each other and edge each other out.
Miki: And how do you think about that related to gender? Is leading from the feminine different from simply leading as a woman?
Andrea: When people talk about misogyny in tech, it’s not really about women. It’s about a set of qualities that happen to be packaged more often in a woman’s body. But they don’t have to be. If you look at really successful women in tech, we often don’t see the qualities that are typically associated with the feminine. Feminine qualities exist in all genders, but either way they are not valued in business and technology. There is pressure on everyone to have a thick skin and to be very logical.
“There is pressure on everyone to have a thick skin and to be very logical.”
Miki: Are there things you think people misunderstand about the diversity in tech issue?
Andrea: When people talk about diversity, it’s often attached to gender or race, but that kind of diversity doesn’t help much if you don’t also have diversity of thinking. And that requires us to make space for feminine qualities.
It’s important to recognize that men are hurt by misogyny in tech, too. Because there are tons of sensitive guys here who aren’t able to exert their true qualities. I see a lot of companies that want a certain number of women or people of color so they can just check a box, but the diversity issue is much bigger than that.
“It’s important to recognize that men are hurt by misogyny in tech, too.”
Miki: I think we tend to focus on what people do rather than how they do it.
Andrea: Exactly, the “what” versus the “how.” A lot of the things that we attribute to the masculine, things that are more measurable and tangible, tend to be the focus of performance reviews and raises. But there are ways to take less tangible, more feminine qualities into account, too.
While we’re talking about this, I want to make sure people don’t think we’re saying that, if a woman isn’t strong in feminine qualities, it somehow makes her less of a woman. This isn’t about grading your gender. Women already have so many standards and expectations we feel we’re held to, the last thing we need is to have someone say, “Now you also have to be the most empathetic.”
Miki: I wonder if we should even try to find another set of words with less baggage. We could also say “yin and yang,” or “solar and lunar.” Left-brained and right-brained. It seems like the words “feminine” and “masculine” tend to trigger people.
Andrea: To me, even the idea of it being binary, of it being black and white, is a masculine viewpoint. Me, I like the grey. I think the reason I’ve been successful in my career is that I can tolerate grey. People tend to want things to be black or white. That includes the way we think about diversity in tech. We need to consider how to reframe the entire issue away from either-or thinking. Because the bottom line is, there are no easy answers.
“I think the reason I’ve been successful in my career is that I can tolerate grey.”
Every woman can fail at being empathetic. Every man can have moments where he’s really sensitive. When I was at inDinero, half the discussions I had were with male colleagues who did not feel valued or heard. A lack of empathy and communication in a company hurts everyone. These are things that break companies. So, for better business and better cultures, we need to value these things.
And we haven’t even talked about different cultures yet. Why, for instance, do women from Asia and India seem to be more successful in tech? Is it because their cultures tend to value more masculine characteristics, like logical right-brain decision making, and those are in alignment with the expectations of tech?
Miki: I want to talk about you a little more. What’s your personal relationship with the feminine? Has it always been something you’ve had a close relationship with?
Andrea: Absolutely not. I started inDinero with another woman, who I now see as a warrior, while I see myself as a healer. But at the beginning, I was really trying to be a warrior, too. I hid my healer side completely. In general I was more aggressive and just constantly trying to prove that I could be technical and rational. It was ok, but I was really unhappy and I felt like a fraud.
There were a few things I did at inDinero, especially relating to sales, that actually drew on my feminine skills a lot, but I didn’t think of it that way because I didn’t have the vocabulary. For instance, I reached $1 million dollars in sales just using referrals. Nobody does that. And why did my clients love me so much? Because I was militant about understanding their pain and solving it, no matter what. I think that’s where my idea for the Empathy Warrior comes from. But at the time, I would never have thought to call it that, and I was definitely scared to lead with it.
“In a way, I’ve always led with empathy, but at first I was trying to hide it.”
It was only after I met my mentor Arina and started doing serious self-work that I came to understand, “Oh, that’s my superpower. I need to lead with that.” Since I figured that out, things have been great. It’s helped me be a better pitch coach, a better investor, a better speaker, a better adviser, and a better entrepreneur. So, in a way, I’ve always led with empathy, but at first I was trying to hide it.
Miki: What does “Empathy Warrior” mean for you?
Andrea: I’m the oldest of three kids and my brother and sister say I’m “aggressively nurturing.” I guess it means that my value system is based around feelings and emotions. But that doesn’t mean I’m passive. Warrior energy is about the right use of power. Like if you’re a kung fu master, you don’t go around just striking people all the time. There’s a time and a place.
As an Empathy Warrior, I always lead with empathy, but when it’s time, I have the strength of a full-out warrior—I can actually be quite ruthless. That’s something I want to challenge the high-empathy crowd with: Are we being ruthless about reaching our goal of making this world a more loving place?
“I always lead with empathy, but when it’s time, I have the strength of a full-out warrior.”
Miki: That’s a great reminder of the way life asks us to get comfortable with paradox. Is there a particular paradox you’re holding?
Andrea: That my best trait is also my worst trait. The shadow side of empathy is you’re too easily hurt and you lose momentum. I’ve done a lot of work to overcome my natural insecurity. People who are super empathetic tend to get walked all over. So I wanted to cultivate my warrior side because that’s all about boundary setting — with others and with yourself.
Miki: Have you read Give and Take? Adam Grant did all this research and defines three categories people generally fall into: givers, takers and matchers. Givers’ main motivation in life is to help other people. Takers, their main motivation is to get ahead, so to win while others lose. And then matchers are sort of what happens when you want to be a giver but you get burned. So matchers decide, I’ll only give if someone gives back equally. They’re sort of the watchers who make sure everything’s fair and equal.
Andrea: They’re the empathy accountants!
Miki: Totally! What’s interesting is that givers are over-represented on the bottom of all the scales: the people who make the least money, who tend to burn out at work.
Andrea: The teachers, the non-profit people.
Miki: Right. But they are also over-represented at the very top of the scale. So he tries to figure out, what’s the difference between the givers at the bottom and the givers at the top? And the difference is very simple — it’s boundaries and a sense of self-worth. Givers at the bottom give everything; they’re the self-sacrificers, the martyrs. And then they burn out and they can’t give anything to anybody anymore. Whereas givers at the top are very clear about what they will give, but they also are fine saying no to things and are careful to take care of themselves, too.
Andrea: They only give when their cup is full.
Miki: I think that’s similar to what you’re talking about, right? How can we be givers, but in a way where we also take care of ourselves?
Andrea: Yes. It’s also about the perception of weakness. One thing we haven’t talked about is the way we evaluate other people in a competitive environment. Because I think people tend to equate empathy with weakness. And that’s not surprising if you look at our role models in Silicon Valley, like Elon Musk and Travis Kalanick. We’ve been taught to idolize competitiveness.
“I think people tend to equate empathy with weakness.”
It’s not always stated, but I have this intuition that people assume that leaders at the very, very top have to be cut-throat. And they assume that people who are middle-of-the-road or failures are the ones who want to support the community. There’s starting to be this assumed price to likability and empathy. People love people with more empathetic energy, but we haven’t seen as many huge wins from them yet. Or maybe it’s more that we just don’t hear those stories as much. Because the really big, aggressive personalities seem to get all the attention.
Miki: Do you feel like there are role models we should highlight who are leading from a more feminine place?
Andrea: Catherine Hoke, the CEO of Defy Ventures is. You. Dave McClure and Christine Tsai have definitely impressed me. That’s why I love working at 500. They’re not perfect, no one is, but there’s definitely little places where they lead from the feminine. And even better, I’ve seen them improve over time. Dave has gotten very, very good at positive reinforcement. He’ll send these, like, love bombs through email and Slack.
Miki: Awesome. A huge part of why I decided to start Leading By Example was to provide alternative stories about what it takes to be a successful entrepreneur. I know how powerful stories can be, and when the only success stories we’re told are about people with a more masculine energy…
Andrea: Or like Lean In and Sheryl Sandberg. I have great respect for her and I’m glad the book was written. But it’s very focused on women growing their warrior sides, instead of calling on business and society to build its empathetic side.
Miki: Yeah I have a lot of ambivalence towards that book, too. I thinks it’s also why I’m ambivalent about Hillary. Again, it’s great to see a woman in that position, but she’s not necessarily coming from a feminine perspective . Again, it’s more about how she’s being than what she’s doing. Maybe that’s just not where we are with politics yet.
So what do you do to help you stay in balance?
Andrea: Sometimes when people are so empathetic like I am, they won’t go out and be the warrior when they need to. So first off, I try to put myself in situations that push me out of my comfort zone—as long as I feel they are helping me grow. I actually have two questions I ask myself when I feel like I’m being pushed. First, is this person trying to help? Second, is there a chance this could work? And if the answer to both is “yes,” I try to find the good in it, even if it’s uncomfortable. If it’s a “no” on either front, I just walk away.
“I try to put myself in situations that push me out of my comfort zone.”
When you’re an Empathy Warrior, it’s so important to get clear on your personal values to help you evaluate and make decisions. Because I can’t say that in every situation I will do the most empathetic thing. And I also can’t say I will always be a warrior. Life is situation-dependent. Sometimes people really need a soft touch. And sometimes the goal you’re working toward is more important than being empathetic. It’s best to have a value system that helps you prioritize between different ways of being, rather than saying it’s either-or.
Miki: I hope it’s clear to people why these things are particularly important within Silicon Valley and for entrepreneurs. Because the things you’re talking about, like living in the grey area, are key for entrepreneurs.
Is that something you look for as an investor or something 500 looks for? Do you consider the team?
Andrea: 500 definitely looks at founders. However, we don’t always define exactly what kind of founders we’re looking for, which I’m trying to change. Personally, I look for self-awareness, because people’s best and worst traits are often sides of the same coin. Look at someone like Elon Musk, who is an amazing visionary. The shadow side of that is that it’s really hard to work for him, because he doesn’t give positive reinforcement. That would never work for me. My whole thing is making people feel acknowledged. But on the shadow side I can be overly sensitive, which can lead to misjudgements. And that’s why it’s the focus of my self-work. Every personality has a shadow side, which is why I look for people who are aware of it and working to improve themselves. Unfortunately, we often think that success excuses the need to do that self-work.
“Unfortunately, we often think that success excuses the need to do that self-work.”
Miki: I want to dig into this idea of a shadow side, because it’s really important and I’m not sure everyone gets what we’re talking about. I think when people hear us characterize something as masculine or feminine, they immediately think we are suggesting one is better than the other. But the way we see it, both masculine and feminine energy has a light side and a dark side. There are wonderful things and dangerous things about both. The goal is to try to get things back in balance, to recognize that we need both of them.
I was reading this post the other day that really got under my skin. The woman who wrote it was complaining about how the majority of creative culture — music, television, movies, fine art — is produced by men, often with no input from women at any stage. And even when women are in charge of their own production, there’s usually a man above them who’s making decisions. She ended by saying, basically, “It will be a great day when the first album is produced that no man has touched.” I got really upset because, to me, that’s every bit as problematic as only men being involved. It’s not “men” or “women” that are the problem, it’s the underlying perception that it needs to be one or the other.
“It’s not “men” or “women” that are the problem, it’s the underlying perception that it needs to be one or the other.”
I mean, I also understand where she’s coming from. I think there are a lot of women who are pissed off at being held back, even in really subtle ways. They want to use their new power to show men how it feels. I really encourage women to check that inclination and question if that’s going to help things in the long run. Or are we just going to have the pendulum swinging back and forth forever, never coming to a middle point?
This reminds me of a question I know we’ve talked about before. When a situation is not the way you think it should be, do you stay and try and change it, or do you leave and try to build something better?
Andrea: Jason Calacanis wrote an interesting article when the whole Ellen Pao thing was happening. He basically said, women should stop trying to join the existing investment firms, because they are just boys’ clubs through-and-through. Instead, women should start their own firms and funds and, when those are successful, people will finally have to give them their fair due. Maybe he’s right, but that’s really shitty. Especially because you have all of these well-connected groups, like the Palantir Mafia, the PayPal Mafia, that are all white men. So saying, “Just leave and do your own thing,” seems to assume a level playing field that really doesn’t exist.
Is it just me to think that staying is a more feminine approach?
Miki: To me, the feminine thing is, you do both. Right? Also, you recognize that change is going to be incremental and we need to be patient. And believe me, that’s tough for me. I so often feel like, sure, things will change at some point, but it’ll never be soon enough. And maybe that’s okay. Maybe there are important things we need to learn along the way. Things about how to do it well, in a way that will last, instead of just “getting it done.”
What about the companies that you fund? How does your Empathy Warrior play into that?
Andrea: I think you see it a lot in our focus on international companies. To paraphrase 500’s Parker Thompson, “Talent is everywhere — access to resources isn’t.” Even just that observation takes a lot of empathy to see. It would be easy to look at companies in developing countries and say, they’re not as far along and don’t have good prospects for fundraising after 500. But we try to assess entrepreneurs within the context of their community; that’s one thing I love about 500.
“Investors think it’s only possible to do well financially OR to do good in the world.”
In terms of how I choose companies, I definitely have a bias for companies that have more balanced personalities. We often talk about “complementary skills” but I also look at complementary relationships. I use my intuition to get a sense of how the team interacts. Actually I think a lot of investors are intuition-based — they just won’t admit it.
I’m also a social impact investor. We could have a whole separate conversation on my frustrations with social impact investing. It goes back to the whole dichotomy problem, where investors think it’s only possible to do well financially or to do good in the world.
Miki: Is it ever hard to be the only one in the room who says, I’m investing from my intuition?
Andrea: I think everybody is doing that to a certain extent, they’re just using data to justify it.
Miki: So why won’t they admit that’s what they’re doing?
Andrea: Because I feel like everyone wants to be logical. I guess that’s the thing in tech, you aspire to be this logical, unfeeling, emotionless…
Miki: You aspire to be the computer?
Andrea: Exactly. Technology is interesting because it doesn’t have emotions. But I don’t think we should be aspiring to that. I’m in tech because of how it affects people — and I think a lot of sensitive, emotional, empathetic people are too.
Miki: Do you have advice for anyone — of any gender — who is coming from a more feminine or empathetic place, and they feel like they’re the only one in the room?
Andrea: I think one way you can have an impact as “just one voice” is by helping to create the culture you want. This might mean calling people out — in a very respectful, one-on-one way — when they do something that’s not in alignment with your values. And that might require you to step outside your own comfort zone, because telling someone you respect that they’re doing something you disagree with, that can make you feel really vulnerable.
“I’ve worked with so many companies where people didn’t feel valued, but no one would be caught dead saying that.”
Another thing is, I try not to take it personally. Ok, so empathy is not really respected or accepted in tech. I don’t see that as a judgement against me. I see it as a reason I need to tell people I want more empathy and emotional respect around me. It’s funny, I don’t think I’ve ever met anyone in tech who would ask someone to be more sensitive or empathetic, even though they tell people to be rational or assertive all the time. It’s like asking for empathy is somehow a point of weakness. So nobody asks. I’ve worked with so many companies where people didn’t feel valued by the CEO, but no one would be caught dead saying that. So my advice is, just start talking about it. When someone hurts your feelings, we all need you to speak up and say so.
Want to know more about healer and warrior energy? Check out The Four-Fold Way by Angeles Arrien, whose work has strongly influenced Andrea and me.
