When Women Lead

While there may be plenty of discussion about closing the gap in funding between women-led startups and those led by men, women still receive just 2% of all venture capital funding. And yet, many women are still finding success as entrepreneurs. How?

CNBC Senior Media & Technology reporter Julia Boorstin dug into the stories of women entrepreneurs founding, funding, and running companies, and uncovered a variety of smart approaches. As it turns out, they do so by deploying a variety of tactics that are often unique to the individual. But what they have in common is striking.

“There is not singular model of leadership that worked across the board for the women I profiled,” says Boorstin, who interviewed more than 100 women and shared the stories of 60 in her new book When Women Lead. “But the women succeeded by finding leadership traits that were really true to who they were.”

Boorstin’s data-rich account of female entrepreneurs and leaders illustrates how women are operating in an ecosystem rife with challenges – lack of access to funding, pervasive bias, smaller networks – and defying the odds to find success. Running companies across multiple industries, female leaders may differ in their approach, but utilize many of the same qualities that have proven to be an advantage, says Boorstin.

“Across the board, they all have a growth mindset, which to me is the combination of humility and competence. And that is essential,” says Boorstin. “But also, female leaders are more likely to lead with empathy, vulnerability. They’re more likely to found purpose-driven companies. They’re more likely to lead in a communal way, bringing in perspectives from across an organization rather than top-down.”

Julia spoke with me in front of a live, female-majority audience as part of Greylock’s Iconversations speaker series. You can listen to the interview at the link below or wherever you get your podcasts, and you can watch a video of the interview on our YouTube channel here.

EPISODE TRANSCRIPT

Elisa Schreiber:
Can we take a minute and look around the room? How often do you get a room like this? This is unbelievable.

Just on behalf of Greylock, I want to thank all of you for coming and welcome you all to our offices. I’m so excited to have this conversation with Julia Boorstin. Woo woo. Let’s get started. Welcome, Julia.

Julia Boorstin:
Thank you so much. This is really a dream. I feel like we talked about this a year ago when the book was not done. And so to actually be here and see so many of you amazing people (who I included in the book but I have never met before in person, face to face), is just like a dream.

So thank you all so much for being here. It means the world to me, and thank you, Elisa. This is awesome.

ES:
Well, congratulations on the book.

JB:
Thank you.

ES:
Okay. Writing a book is a full-time job, and then you have a full-time job, and then you have a family and all the things. So we’re going to get into it. And plus, I don’t know how many of you had a chance to read the book yet, but it’s basically a PhD dissertation written with the lens of such a human voice and it’s very accessible, but it’s so data-rich on exactly what it takes or how these women have become incredible leaders; the patterns of incredible women leadership. And so, we’re going to talk a lot about that today. So thank you.

But I think let’s just get started. So you’re at CNBC. You’ve been at CNBC for 16 years. Why don’t you give a little summary of your background?

JB:
So I’ve only had two jobs. I was at Fortune Magazine for six years straight out of college, and then I switched over from print to TV business news. And I’ve been at CNBC for 16 years. And in that time, I’ve covered media and technology. And one of my favorite projects I do is the CNBC Disruptor 50 list, which I created over a decade ago now. And I always was fascinated by entrepreneurs, and I figured – CNBC’s focused on the public companies – but the entrepreneurs were always so exciting and interesting to me; the way they were thinking differently about business and trying to transform industries.

And so, the Disruptor 50 gave us a lens to look at these founders. And I found in interviewing them, I was of course struck by the fact that the women were in a tiny minority, but I was also really inspired by the women in particular. And as I interviewed more and more of them, I found myself leaving these conversations just so jazzed up, seeing how these women had defied the odds. And I wanted to dig more into their stories. And at the same time, some of my colleagues at CNBC, including Sally Chen who’s here, were working on trying to highlight the people and companies who were closing gender and diversity gaps. We did a huge amount of coverage of the Time’s Up and Me Too movement, but we wanted to focus on the solutions.

So as we were digging into some companies, whether it was PayPal or Salesforce (that were really using data to close pay gaps and promotion gaps) I kept on coming across the stats about VC funding. Over the past decade, about 3% of all VC dollars have gone to female founders. Last year, that number dipped to 2% of all VC dollars. About 15 and a half percent went to co-ed teams. So last year, about 82% of all VC dollars went to all-male founding teams.

So the stats were so crazy to me, and so persistent, and we’ve seen so much change in other parts of the business world or in politics. But to see such sort of static numbers in terms of equity in investment, I thought these women have defied crazy odds. The women who have succeeded have done so despite every deck being stacked against them. So if we can figure out how they succeeded, they would have leadership lessons for everyone.

ES:
So that’s why you decided to dig in and write this book. I have to ask before we get started, what was your process for writing?

JB:
So at first, I started off by connecting with VCs because they see so many companies come through. And I talked to Pam Kosta from All Raise, Aileen Lee, who’s not here, Maha Ibrahim, and Sonja Perkins. And I would ask them, “Tell me about some of the women you’ve invested in.” And this goes back to when I remember interviewing Maha at a Fortune’s Most Powerful Women’s conference maybe five or six years ago. “Who are the women who seem really exceptional to you, and who have you seen really approach problems and sort of company building in a different way?”

So I started with the VCs and then I started interviewing people, and one person led to another, and each woman I interviewed would often connect me with five other women. And so, I met so many phenomenal people through this process. And some of them, like Heather from Solv, I didn’t get to include her in the book, but through meeting her through this process, I got to put her on CNBC.

I feel like it all sort of bolstered my coverage at CNBC and exposed me to so many new companies. And also I was just inspired by these amazing women. Deji Packat is here. And so one person led to another. Heidi was really helpful introducing me, but this sort of daisy chain exponential introductions. And so, I was doing these interviews on Zoom. I started the process before the pandemic, but then once everyone went into lockdown, people were around. So I said, “Can you Zoom with me please?” And one thing that I actually think was really valuable about that time is that for everyone, their schedule stopped. And I think actually people were really reflective. I think people were thinking, what do I care about? What matters to me? Is this a moment where I can make some introductions? And so many people helped me in that time, and I think really opened up about what mattered to them and what was driving them for their companies or for their investments.

ES:
It’s interesting that you talk about the sentiment of being reflective in that time, because I found the entry point in your book, you were doing a lot of reflection. You were talking about your career and your journey. Maybe you can share a little bit about your own experiences and you started at Fortune. You’re now at CNBC. Can you share a little bit of your experiences of how you’ve also been a woman who led?

JB:
I mean, it’s interesting because I really started working on this book around the time I turned 40. And I was like, “Ok, I’ve been in this business a long time. I now have the confidence to know that I’ve seen so many amazing leaders, including many male amazing leaders. But also, what can I do to have an impact in my storytelling?”

I think journalism does have an impact on the images we share, the narratives we share. I know this is something we talk about a lot, and I thought this is something that I feel like I can sort of move the needle on in getting some of these stories out there because they’ve impacted me. I want other people to know about them.

I think back to my childhood and the time I was in college, my mom always was like, “By the time you grow up, men and women will be equal. Everything will be fine. Don’t worry about it.”

And yeah, she was wrong, but by the way, I believed her. And it was really empowering in college not to worry about that and to have this feeling of I was going to do the same things as my male counterparts and didn’t have to be intimidated by anything. And then I entered the workforce, and lo and behold, I was at Fortune Magazine, and not only were all the senior editors men, but all the companies we were reporting on were of course led by men with very few exceptions. Very, very few exceptions, because right now, female CEOs represent eight and a half percent of the Fortune 500, and that is an all time high.

So I think in my journey as a journalist, I had to grapple with the fact that this myth I had been told of the gender equity in our future was entirely false. Things were moving incredibly slowly, and though there was some progress, the progress was slow. So I figured out how to exist in that world.

In my early days at Fortune Magazine, I would wear these hideous boxy suits and glasses. I really don’t need glasses, but I just tried to seem older and more serious than I was. I was 21 years old when I started. I really felt out of my depth and I was oftentimes criticized by these older men I was interviewing for being so young. Literally they’d be like, “How could you possibly know what you’re talking about? You’re so young.” And I would say, “Well, I did my homework, here are my questions.” So I figured out how to navigate that. But then once I joined CNBC and got older, I did start to see many more women in leadership roles, and especially in the startup space, I thought I sort of felt things changing. And even if it was the female COO and not the CEO, or a smaller company, I started to feel like things were starting to shift. And even if you look at the numbers, just in the past seven to 10 years, things have been starting to change. And I was really excited by that and wanted to tell some of those success stories.

ES:
Well let’s dig into what you’ve learned. So how many women did you interview? Sixty?

JB:
I talked to about 120 people and there are about 60 included in the book.

ES:
Got it. And what were some of the biggest takeaways?

JB:
Well, the one thing that struck me across the board is that we have this very specific archetype of leadership. And I’m sure you’ve seen it on CNBC or in all the movies that perpetuate the stereotypes, but it’s a very male, top-down hierarchical decision made in a corner office. And the reality is that people can succeed by leading in all sorts of different ways. And there was not a singular model of leadership that worked across the board for the women I profiled. But I think that the women succeeded by finding leadership traits that were really true to who they were and saying, “This is what I’m good at, this is what I’m not good at. How can I take what I’m good at and develop that and really push myself to figure out how to be better at that trait, and how can I surround myself with people who compliment me?”

So I think this idea that any of us has leadership traits, maybe even some traits that we think of as flaws, that can be developed into leadership superpowers. And I think of the women who are self-professed introverts and figured out how to use that toward their advantage, or super empathetic and figured out how to use that to be better at connecting with their employees and customers. So I think there’s not a single model, but this idea of knowing yourself, figuring out what you’re good at, getting better at it, and really pushing yourself not to compete with others, but that self-competition is really essential.

ES:
So you talked to a lot of women in a lot of different industries for this book. In fact, one of my old bosses and mentor Gail Becker who started Caulipower is in the book. But my question, because of the room that we’re in and the community here, is really focused on the venture-backed ecosystem. So was there anything specific that you found, I guess good or bad, about what’s happening in venture?

JB:
Well, I mean, I guess there are a couple things. They’re like the traits that are working, and I think those are true outside of venture as well. And then in venture, I mean the numbers are not really moving, but there are a couple things that are enabling women to succeed more.

So to the first question of what those traits are, Gail Becker, I write about in the chapter about a growth mindset, which Deidre is also in that chapter as well. And the women all have a growth mindset, I would say, across the board. A growth mindset, which to me is the combination of humility and competence. And that is essential. But also, female leaders are more likely to lead with empathy, vulnerability. They’re more likely to found purpose driven companies. They’re more likely to lead in a communal way, bringing in perspectives from across an organization rather than top down. Female leaders have been ranked better at developing diverse teams and stuff like that.

So one thing I have to say though is I was doing all these interviews, but I realized the more interviews I did, that just telling these women’s stories was not going to be enough, that I needed to dig into the data and the research to explain what it was that I was seeing in these stories. And also, to have an academic validity to my argument that female leaders have amazing traits that everyone should be studying.

ES:
Well, it’s interesting you mentioned a couple traits there, and one that caught my attention was this notion that women tend to start purpose based companies, or mission driven companies with a social element to it. But I also know your data uncovered something about that. Do you mind sharing?

JB:
Yeah. So some of the stats have found that women are about 20% more likely than male founders to create a purpose-driven company. Other stats have the numbers higher. And based on the number of women I’ve interviewed, I actually think the numbers are higher than 20% more than men. And that means just in addition to pursuing profits, having some social or environmental impact. Heidi invests in these companies and introduced me to an amazing founder, Christine Mosley, who has a company that – oh, Christine, you’re here, hi!. [For her company] success is having a positive environmental impact. So really not doing a buy one, give one, but really aligning the positive outcomes for the company with helping the environment or people. So, women are more likely to found [companies like] these. But what’s really interesting from a VC standpoint is that having a purpose shows an element of nurturing. And all the studies find that women are expected to demonstrate nurturing even when they’re running companies or doing whatever.

And so oftentimes, that brings bias. So if women succeed in male-dominated fields, they’re judged more harshly. If women fail at sort of so-called nurturing fields, they’re judged far more harshly than a male failure in that same field. But interestingly, when women are launching purpose-driven companies, that actually eliminates an element of bias because the investors, male and female investors, think “Yes, this woman is being a hard-driving entrepreneur, but she is also being nurturing.” So it checks both boxes in the brain in terms of fitting that pattern and matching that stereotype of what women are expected to be. So it’s not necessarily a good thing that this is still based on stereotypes, but the idea that having a purpose component to a company can eliminate some impact of bias in fundraising is really surprisingly interesting.

ES:
Or it amplifies the bias, but it lubricates the capital.

JB:
Yeah.

ES:
Right. Yeah, it’s still some bias, which, I don’t know…capital. You need to be able to fundraise.
So the other thing that I thought was really interesting in the book was you talked a lot about the importance of having diverse networks, and not just women talking to women, but women from different industries connecting with each other and also women coming together in the same industry. Can you talk a little bit about what you learned there?

JB:
Yes, and I’m so glad to have some women from All Raise here, which I know has been so impactful on this community here in San Francisco and Silicon Valley. So I write a chapter about the power of community because one reason I’m so optimistic that there will be change is because there are all of these networks and communities, both in the tech space and also just in the sort of more mainstream business world. And there’s data that has found that men are successful if they have the biggest network. But that is not true for women. Women have the most success if they have a tight but diverse network. And there’s all of this research that finds that women are successful, not if they have their friends around them saying just good job, keep on going. That’s important. But what’s even more important is to have a diverse network of people who are not your friends, who are not your work colleagues, who are giving you honest feedback and pushing you and trying to hold you accountable.

And that’s the whole thing of this idea. [This question of] Who’s going to make you be your best self? Not just those who are saying you’re doing great, but saying don’t forget you set that goal, you’ve got to try to hit it. So this idea of the power of diverse networks and also the power of networks to help combat the negative impact of bias.

There is this research that I just love so much, and I think about often, that found that yes, when people are subject to stereotypes or bias, it has a negative impact on performance. These researchers got together, a group of women engineers, they gave them math tests, and measured their scores. They also got female engineers together and told them that women are bad at math, women are bad at engineering. Take the math test. Scores went way down, not surprising. Bias and stereotypes can really hurt performance, as well as feelings. Then, they got together these groups of women in small groups, they called them micro environments. They put them together. They let them talk to each other. They told them the worst stereotypes possible about how badly they were going to do on the math test. And then they took the test, and the scores were fine. They did not move at all. And ultimately, what it comes down to is these micro environments, small groups of people who otherwise would feel like they were all alone, can combat the negative impact of bias.

And that’s why it’s so important for big companies to have what they call affinity groups, but also for people who are outnumbered to find each other and to help each other, and then to help build bridges into the macro environment, if you will. But in the broader world, that is dominated by men. And that’s why what All Raise is doing is so important because you’re both creating those communities and also bridging into the more male-dominated world where women traditionally have not had as much access.

ES:
What did you find in terms of venture funding and some of the patterns? I think there’s stuff that women can do, build networks, build relationships. Those are the things that are within our control. And then there’s externalities. So I know you dug in a lot in terms of the women who do get funded and why and how, and there was a big exploration of pattern matching. Maybe we can explore that a little bit.

JB:
Yeah. So we talk a lot about unconscious bias and I feel like it’s a term that’s used so much, it almost loses its meaning. And ultimately, what is such a powerful force in Silicon Valley is this idea of something very simple: pattern matching. People are always looking for patterns. What does success look like? What does failure look like? Does this woman who came in with a company in a field I’ve never thought of before just not fit into a pattern, so I can’t categorize her as potentially being a good investment?

So there’s so much data about how, especially at the early stages, investors are betting on the entrepreneur and the idea and they don’t have any track record. And there was some great data out of Harvard Business School showing that well over 50% of all investors say that, at any stage, what they’re really betting on is the entrepreneur. So if you’re looking for a pattern of someone who is an engineer who graduated from Stanford and has had an enterprise software company that he already sold to Microsoft, that’s going to really limit. That pattern is pretty narrow. And though it works for a lot of situations, it is not going to be inclusive of some people who could end up being incredibly successful.

ES:
So what were some commonalities of the women that did make it and that did come out of the book? How do we pattern match for those women?

JB:
Well, I hope that the book will share new patterns, and this idea that there will be a new archetype of what leaders could look like, or new archetypes, I should say, because the more we can have a diversity of those images, the better. But I think that women do have a tendency to do more with less. And that has traditionally been because they’ve had less access to capital. But now in this market environment where we see investments go down, so much economic uncertainty, I actually think that’s going to be incredibly helpful because female founders didn’t have the option of blowing money on a foosball table or beer gigs or whatever it was. But maybe now that sort of more fiscal responsibility, it’s going to be an advantage. So I think that’s one of the key things.

ES:
Yeah. And actually, I recall too there was a lot of exploration around the women leaders that you profiled (this is my takeaway) they all seemed to have been very good at navigating crises. So whether it’s the financial downturn that we’re in now or something happening acutely with their company, it was very clear that there’s this solid mastery of getting through a crisis. I don’t know if that was something that you [saw as well]?

JB:
So actually, employees would rather have a female leader in a time of crisis, which is interesting. And women have been found to have a higher adaptability quotient. This idea of being able to look at data to look around corners and figure out how to swiftly make decisions based on data, not get stuck in what maybe you had decided to do six or 12 months ago.

There’s some really interesting data around the financial crisis, but also around the pandemic about how female governors outperformed their male counterparts in very similar states. Even if they had the same policies, the female-led states minimized death to a greater degree. Same thing is true of female-led countries. And then if you look at the companies, there’s less data at this point, but this idea of being able to quickly adapt to new situations and also maybe being better prepared in the first place.

I write about Caryn Seidman Becker, who’s the CEO of a company called Clear. And as many of you probably use Clear, but this is a company that was entirely reliant on airplane travel, and she now has-

ES:
And big concerts.

JB:
Well yeah. And that’s still even a relatively new thing, but they totally adapted during the pandemic a month before. Or almost a month before our pandemic was declared, she decided to slash $24 million in spending for the entire year in advertising. So not waiting, not hoping things are going to get better, not making decisions piecemeal, but saying we need to cut our losses in marketing now. And now they have this entirely new health business. So this is a perfect example of someone looking at the numbers, reading the numbers, and saying, “What can we do to make sure we’re not going to just be playing defense and making little tiny decisions every month?”

ES:
So we’re going to open it up. I have one more question and then we have some mics that we’re going to open it up. So if you guys have questions for Julia, start thinking about it.

It’s funny. When we started the conversation and you were mentioning your experience growing up with your mom, we’re in a post world, we could do whatever we want. And I had very much the same experience growing up. It never occurred to me that because I was a woman, I wouldn’t be able to do something, because our moms all fought for these rights. Why do you think (as we’re at the end of 2022) this is still happening, Julia?

JB:
I wish I had an answer to that. I think things move really slowly. I think change happens really slowly. And it was interesting. I was just in New York talking to some women in finance, some women in the advertising industry, in very-male dominated industries. And they were saying that they see more opportunity for female entrepreneurs because it’s going to take forever until the banks have equal numbers of men and women at the top, or whatever it is. But if women strike out on their own, they don’t have to wait. And that was something that I actually thought was interesting and I hadn’t thought about it that much like that before.

So I think the barriers to entry for founding startups have come down. This is something we talk about, and I’m hopeful that the amazing women like those in this room will start to really drive change. But it’s crazy how low the numbers are, and I think just structures of power are pretty entrenched and things move slowly.

ES:
Any questions? Right there.

Miriam Rivera:
Hi Miriam Rivera from Ulu Ventures.

ES:
Miriam. Hi Miriam.

MR:
Today, I was reading The Broadsheet, and there was a discussion by Sheryl Sandberg around the great breakup and how more senior women are leaving positions in corporate America than before, and also more of them are experiencing burnout. How do you think this will impact the ability to change the Fortune 500 and/or change how women work?

JB:
I’ve been hearing a lot about that, and I guess the question is, do those women go off and start their own things and do they say, “I don’t want to work for someone else and be subject to the hierarchy, let me just go found my own thing”?
And I think that would be an opportunity for growth. But I think it’s hard, and I think women have been shouldering so much during the pandemic, and so much before the pandemic, and McKenzie and Lean In have done really important research about the broken rung and this idea that women are entering the workforce at the same levels, but they’re not making it to the senior levels because they’re dropping out or they’re not getting that promotion around when they have kids. And this new kind of early retirement, if you will, of women who are more senior I think could have really negative repercussions. But I just hope that they go off and start things and hire women. I hope there’s a way to spin that.

Sarah:
Hi, I’m Sarah. I run Cleo Capital, and would love to know what you found around [this concept of] whenever you talk about gender, the elephant in the room tends to be race, which is women who look like you tend to do a much better job at navigating the absolutely horrific minefield that is the world, than women who look like me. And so, I would love to just know what findings, if any, there were around race and how to make it sort of an intersectional success.

JB:
It’s very important to look at intersectionality. The percentage of VC funding that goes to women of color is minute compared to the tiny percentage that goes to all women. And I have a lot of data in the book from Digital Undivided, which is a New York based organization, which is doing awesome work. They put out a report every year called Project Diane, and I believe the latest status, 0.27% of VC funding goes to Black women, or did as of the last study. So, the numbers are horrific. There is great work being done on intersectionality from an organization called Project Include that’s run by Ellen Pao. And they’re really looking at how every layer of identity brings additional bias, and sometimes even more so than just twice as much. It can have a really massive impact on the way founders, women of color in particular, are facing challenges in the VC space.

But Project Include is really working on that, and also working on training white male led companies to be more inclusive around not just hiring, but also retention, which is a massive problem, especially at these tech companies.

So I think the answer is that the vast majority of corporate programs that are affinity groups for women have been found to help white women and not to help women of color. And so, I think it’s this entrenched problem where companies think they’re doing the right thing by having an affinity group and they’re not realizing that they’re excluding a huge piece of the population.
There’s a great diversity of stories that I feature in the book and I hope the more we can get out the imagery that successful entrepreneurs are not just white women, but women of every race and background, I think is a big part of the story, but I think that the numbers need to change as well. And so, that’s why I think it’s so great that there’s starting to be a lot more granular data on the intersectionality and more companies, more organizations, nonprofits focused on that.

ES:
We have time for one more question. We have one of them in the back. Oh, we have a few actually. I’ll get to all of them. I’ll get to all of them. I mean, listen, now or never. Right?

Audience Member:
Julia, you spoke a little bit about some of the challenges during the pandemic that women faced and we’re at this really interesting moment now where we hear a lot of the men CEOs say, “We want people back in the office.” You don’t hear that as much from women, it occurs to me. And while it was really challenging at the beginning of the pandemic, it’s given us so much flexibility, if you have kids, if you have families to do things in addition to your work and kind of figure out your schedule on its own. So how do you think that this evolves? Any sort of early anecdotes or data from the women that you talked about in terms of going forward and how that work-life balance hybrid or remote work is going to look like?

JB:
It’s such a good question, but one of the challenges also is this idea that, if men are more eager to get back to work, they might get more promotions or pay increases because they have the face time. And so, I know a lot of companies are trying to have consistent expectations for their teams, so women are not left out. And so, there’s this sort of double bind here, whereas women may prefer to stay home, but if they do, they may miss out on opportunity. And I think that’s why we’re seeing companies like our parent company, NBC Universal, say you need to be in the office these three days a week. So there’s consistency, and then managers can sort of consistently not think like, “Oh, I haven’t seen her around, has she been doing her job?” They just know everyone’s sort of on the same schedule. So I think this is going to be a really hard question to navigate because, obviously in a lot of situations, flexibility is great, but you want to make sure that not being in the office and having the face time doesn’t prevent you from rising through the ranks.

ES:
We have another question right here.

Brena Lee:
Hi, I’m Brena Lee. I’m an entrepreneur at Heart, and so I’ve done the whole raising thing and everything through VCs, and what I think striked me, what you said was 3% of VC money goes to women, at least in the last year.

JB:
2% in the last year.

BL:
Or 2%.

JB:
Yeah. 3% on average over the past decade.

ES:
Not great.

JB:
Not great.

BL:
No, no, no. It’s not great. But what my question is is, do we have a problem with the funnel of women entrepreneurs on the board? Is that also another reason why that percentage is so small?

JB:
So I really wanted to know how many women were pitching, and I was trying to figure out what that total universe is to know what the fail rate was of women. There is not comprehensive data on this. I dug really deep. The closest thing I could find were these two data points: Female founders are 42% of all small business owners. So when it comes to, not VC but just overall small business, women are 42%, and they are founding companies at a higher rate than men. So there’s that fact. Then, if you look at Silicon Valley Bank, they’re clients. So these are people who have had enough success that they need to be working with Silicon Valley Bank. 28% of them have at least one woman, or had at least one woman on their founding team, at the same time that I think 14% of all deals went to women.

So the success rate would be based on that data. And so, I had to do some extrapolation. There are many more women who are operating and trying to raise money than are actually succeeding and raising money. So women are raising less frequently and raising lower amounts. But the numbers, if you’re looking at the 28% and that’s a couple year old data, and then the 42%, many more women are trying than are succeeding in raising. And then also, I’m hearing a lot about how more women are trying to bootstrap because they don’t even want to start the fundraising process until they’ve had some metric of success because they know it’s going to be harder for them. So we are seeing more women bootstrap the seed and the pre-seed stage.

Audience Member:
Is there anything we can do to help with the funnel?

JB:
The question is what part of the funnel are you talking about, the pitching or the-

Audience Member:
Probably the women entrepreneurs, probably the one piece, and then if they become entrepreneurs, they obviously will need to pitch and raise money.

JB:
Yeah, this is really something to talk to All Raise about because they’ve been working to help women understand when they should raise money and when they shouldn’t. Like, when’s too soon, when’s it not worth it, when is it going to be really helpful? And I think, by the way, the small cohorts that All Raise is doing are really valuable in helping women navigate that. So I think mentorship is key, which again, All Raise is doing. But this idea of mentoring and helping women navigate these challenges and making sure they know they’re not doing it alone.

Stephanie:
Hi Julia, Hi Elisa, this is Stephanie. I’m an AI and infrastructure angel. So this book is uniquely striking to me because it is so data rich, and in a way that is going to allow it to be better received and supported by the ecosystem. So my question is, with this group of people that Greylock has assembled in this room today with the Greylock team, what are one or two things that we can do right now?

JB:
Well, I really did want it to be data-driven because I started off just wanting to tell the stories, and I was like these stories of inspiring female leadership are not going to be taken seriously without data to back it up. And I thought that was really important. And I think the more the women in this room and men in this room can sort of help spread the word about the data, I think that that’s really helpful. And I think it could be really empowering going into a room knowing what types of questions women are more likely to be asked, and just using this data to try to help defeat bias because I ultimately do believe that the numbers will speak for themselves, if we could strip out all the layers of bias that are preventing investors and everyone from seeing the opportunity right in front of them.

ES:
Will you pass the mic right to your… There you go. Thank you.

April Underwood:
Hey. Nice to meet you in person. Hi, I’m April Underwood. I’m an Angel investor and co-founder of the group Hashtag Angels. And I know Julia got to speak to one of my co-founders in the book, which is awesome. So thank you for telling the story. I’m curious if you can speak to the media perspective. You’ve written this amazing book. You’re doing the work to tell these very positive stories about female leaders. So thank you. I think one of the things that female leaders often just can see is that there is sort of a long history of hit pieces on female leaders, oftentimes seemingly for behaviors or for situations that are not so different than their male peers that may not have that sort of media coverage. So can you comment a little bit on is there anything happening inside newsrooms that potentially pushes against that dynamic and that bias literally playing out in the media?

JB:
Well, thank you for being here. I do have a whole section on the Hashtag Angels in the book. So you’re doing really important work to get women and more diversity on cap tables. This is a sort of perpetual question of the hit visas on female founders. I do think part of it comes down to token theory. Whenever someone is in a minority, they’re going to be drawing increased scrutiny and more attention to them, usually in a negative way. So I think there’s just that fundamental curiosity. And then I think that it’s the pattern matching. And I’ve been talking this week about the Elizabeth Holmes trial starting up again, and how I will obsessively watch what happen-

ES:
Hashtag girl boss.

JB:
Yes. But I think that there’s this perpetuation of these archetypes and that idea that female CEOs look like Elizabeth Holmes and act like her is really dangerous for society, both in terms of the intersectionality of that’s not what founders look like. They’re not all white blonde women. And to say that they’re all frauds and defrauding their investors obviously adds another level of toxicity into that. So I think it’s a combination of a number of factors. I can’t imagine any newsroom saying, “Let’s go out and take down women.” I don’t think it works that way. But I do think that these things go in cycles. It’s all about the stereotypes and the archetypes just being perpetuated over and over. And I think it’s time to break free from those cycles and start telling positive stories. And that’s why I wrote the book.

Audience Member:
First, thank you, April, for asking the question as you did. I got chills up and down my body. So sort of a vulnerable question is, do you have any advice for female founders? Because on the one hand you want to provide a visible example of what’s possible. On the other, it feels almost inevitable that an overexposure will lead to something negative. So it’s sort of a silly question cause I don’t know what you’re going to tell me, but I feel that I want to wait until I’m more successful, right, before I act bigger, which I know is not what happens with your male counterparts.

JB:
Yeah. It’s hard. I think just knowing what you’re up against. I’ll be honest, I was really depressed when I was going through the research on how women are judged more harshly. And I was telling Alyssa, “That’s the chapter of the book I didn’t want to write because it was so painful.” And I probably had 50 studies about all the ways women are judged more harshly. They’re judged more harshly for using humor. They’re judged more harshly for showing any emotion. Obviously judged more harshly for showing anger. They’re judged more harshly if they’re not seen as nurturing all the time. And then, they’re judged more harshly if they’re also not aggressive. It’s so many different things, and I don’t know how you would ever contort yourself to meet all those expectations, period. But what I realized is women are succeeding because either they’ve figured how to navigate these things or not to let them bother them.

And I think just having information about it and seeing the numbers and knowing how, if you go into a pitch meeting, you’re going to be asked slightly different questions than a man would. Just having that information is so empowering. And I talked to one woman, Kim Taylor. So you have a company called Cluster. And we were talking about this study about how women are judged more harshly by their employees if they give critical feedback. And she was like, “Oh, I have to give critical feedback, that’s my job.” But there was a situation in which she didn’t have time to deal with blowback and she needed to get this done. And so, she had a male deputy go and deliver the feedback, and ultimately that’s not the world she wants to live in or the world any of us want to live in. We want to be able to do our jobs.

But she said in this situation, having that information about how I might face backlash was really helpful because I could just get my male deputy to deliver the feedback and I could go on with my life and not be bogged down in backlash at that moment. So I think having the information about what you might face is going to prepare you, and then just making those calculated decisions about when you’re going to take the risk or not to do something that will not… You’re never going to conform with a stereotype of the male leader, but knowing what you’re up against I think can be helpful.

ES:
Well, I think we’re at time. Hopefully this has filled your cup a little bit. You can go into today and feel really empowered and excited about the future for us. Julia, thank you so much for spending time and sharing your insights and your incredibly data rich reporting and putting it into an easily read book for us all. And we really appreciate your time.

JB:
Thank you so much. It means so much to me to see all of you here. I really appreciate it. And thank you so much, Elisa.