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Author, entrepreneur and tech executive Elissa Shevinksy discusses the challenges that she experienced while working in the tech sector, and what led her to write her book “Lean Out: The Struggle For Gender Equality in Tech and Start-Up Culture.” Elissa shares her perspective that gender and diversity inequality in organizations is often symptomatic of deeper problems, and how progressive movements and leaders can do a better job of creating allies and coalitions. Elissa also talks about her own evolution as a leader, and what she has learned along the way.

In this episode you’ll discover:

  • The challenge that Elissa came up against while trying to express herself in her work (3:44)
  • How to create a culture of empathy (6:30)
  • Why gender inequality is the “canary in the coal mine” for many organizations (14:00)
  • What is needed from leadership when it comes to diversity and equality (23:20)
  • How to get cooperation and support from those with different viewpoints (31:00)
  • The scarcity mentality vs. the abundance mentality (37:00)
  • How progressive organizations can do a better job of building coalitions (40:30)
  • How Elissa has taken her power back (50:00)
  • Why Elissa changed her appearance at work and how it helped her (52:00)
  • The importance of being honest and authentic about our identity in the workplace (54:45)
  • How Elissa is showing up differently now as a leader (57:30)
  • The importance of sharing our journey with others (58:15)

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Listen in now, or read on for the transcript of our conversation:

JENNIFER BROWN: Welcome to The Will to Change. This is Jennifer Brown.

Today, my guest is Elissa Shevinsky. Elissa is a technology executive, entrepreneur, cybersecurity expert, public speaker, and author.

She co-founded Glimpse, an encrypted photo and video sharing app, with Pax Dickinson in 2013. After Glimpse, Shevinsky was funded by MACH37 for Jekudo Privacy Company. In 2016, Shevinsky joined Brave as head of product.

Shevinsky has spoken and written on enterprise security policy. She spoke on the potential for social media to influence election outcomes at HOPE XI. Shevinsky is the founder and organizer of SecretCon.

Elissa, welcome to The Will to Change.


JENNIFER BROWN: Well, I am obsessed with your book, which is called Lean Out. I literally bought it just based on the title alone. I remember it came up in my Amazon recommendations feed. I said, “I wonder what this is.” I couldn’t put it down. I highlighted every page. I felt really “seen” by the stories of the women that showed so openly and vulnerably in the book.

Your story is in there as well. It was really the antidote to Lean In. It completed the picture and finished a conversation that was beautifully started by Sheryl Sandberg, and then was totally expanded by you with a point of view that I personally feel more aligned with in terms of the messaging. I really recommend folks check it out.

We’ll get to that in a moment, but I wanted to start with you and your diversity story. On The Will to Change, I always begin by asking people, “What is your diversity story?” What has been the most transformational for you in terms of aligning all of who you are and endeavoring, as you do, to bring your full self to your life and work as a woman in technology? Tell us a little bit about how you became you.

ELISSA SHEVINSKY: That’s a big question. It really started with my entrepreneurship journey. I became an entrepreneur because I wanted to bring all of my self into my work. You go into an office, and it’s only a piece of you. It’s so hard to express all of yourself in a corporate role, so I started these companies, these startups.

That’s when I started to hit up against what you could call sexism. Just like we’re seeing all of these stories in the news and all of these stories in Lean Out, as I started this journey to try and express myself more fully through my work, I ended up hitting up against Paul Graham and other folks like him. It was very difficult, but I just kept focusing on making software.

In 2011, 2012, 2013, nothing mattered to me but leading software teams. Nothing mattered to me but building apps. That was the only focus for me. No matter what happened, no matter what bad things happened, I just ignored them and kept going.

That’s one of the reasons why I became successful, I didn’t let anything stop me. My hope is that younger women who are coming into the field won’t have the same experience. I’m seeing girls’ clubs starting. You have the “old-boys network.” Now, you have the “new girls network,” where women are helping each other. I’m seeing things getting easier in a lot of ways.

Talking about journey, though, Lean Out was the other piece of that. I wasn’t fully “woke” to what’s going on until I did Lean Out, which is remarkable. I, myself, had experienced so much sexism, but I didn’t really appreciate what was going on with everyone else. I didn’t really fully understand everything until I did Lean Out. I collected these stories, and I read them. And if you think it’s intense to read the Lean Out book, imagine living in it, putting it together, and all the other stories that I heard that didn’t make it in.

For about six months, I just lived in this space where I was thinking about the experiences of these women and gender-queer people who were having a tough time.

After finishing Lean Out, I was a completely different person, and I think a better person, someone with a lot more empathy and interest in trying to be helpful.

JENNIFER BROWN: Yes. You just lived in that space of other people’s stories. There is no better way to challenge your own biases and expand your sense of other people’s experiences than doing what you did. I can imagine being the editor allowed you to be a learner at the same time. You’ve brought so many different viewpoints to a lot of people. While we can’t walk in other people’s shoes, the commitment to learn, listen, and imagine what that feels like is building empathy. That’s why the work I do with our corporate leaders in particular is asking, “How do we build that empathy through storytelling? How do we create an environment where somebody, in the context of their day job, has to parachute into somebody else’s life and experience?” It’s so difficult to do that. I’m not surprised it transformed you.

Even reading it, I picked up so many new things, but I felt validated around a lot of the things that we’re talking about whether intersectionality, gender queerness or opting out of corporate culture by a lot of talent. We hear from our clients, “We can’t attract people, we can’t find them, we can’t keep them.” When you read your book, you realize this is an intense experience that many people are up against. Just to have the energy to hang in there, navigate it, and blaze a path for others, even though you, yourself, are completely uncomfortable every single day is asking so much of diverse and underrepresented talent.

I roll my eyes and I say, “Well, culture eats strategy for breakfast,” which is one of our favorite sayings. Your culture is not one that’s comfortable, and until you fix that, you’re not going to be able to diversify. It’s not a surprise your numbers haven’t changed year over year.

ELISSA SHEVINSKY: That’s exactly right. There’s a chapter in Lean Out that I just love by Squinky. Squinky talks about how making things is easy, but fitting in is hard.

I love that because I think it speaks to anyone who is creative, who’s good at making things, who’s comfortable with the building part, but then it’s the fitting-in part that’s hard.

JENNIFER BROWN: Yes. We want to do the work, we want to be creative and do our best, but there are so many things that get in the way. I call it “static.” It’s also death by a thousand cuts. Every day, walking the halls, being on teams, being the only one “however that’s defined” not seeing any role models ahead of you in your career who have really made it work without opting out, without “leaning out,” frankly, and starting your own thing where you can have total freedom and agency.

I appreciate your story as well. I was a corporate refugee who also had to live my truth and start my own thing so that I could control it. Otherwise, it felt like I would suffocate. This is not good news for the future of work. Not everybody is going to be an entrepreneur. A lot of us need to have that paycheck and that package and that career path. If everybody starts to lean out, then who’s left?

ELISSA SHEVINSKY: That’s right. When I first published Lean Out, this was very new. It was new for women to come forward with their stories this way, and it was new to say, “We want to be authentic at work.”

We’re making some progress there because companies are now saying that they want women, they want LGBTQ, they want gender-queer people to feel at home. Even if that’s only PR, the companies still are saying it, and the companies still have to make efforts to include all kinds of people. That’s new. That’s a new thing.

I remember asking to turn the air conditioning down at an office 15 years ago. My male manager pointed to the men, who were comfortable, and told me to put on a sweater. He then looked at me, saw I was already wearing a sweater, and just kind of shrugged.

Those small things, they don’t happen the same way anymore. Companies understand that they need to at least try in small ways to make all different kinds of people feel comfortable.

I’m feeling more optimistic about corporate environments becoming a better space to express yourself. That said, they’re still not the best space. They’ll never be the best space, and that’s why we’re seeing so many young people and older people all with a tremendous interest in entrepreneurship, but that interest isn’t necessarily matched by having an entrepreneurial spirit, mindset, or training. You see a lot of people struggling for that reason. Instead of struggling in a corporate environment, they’re struggling because they want to do it on their own, but it’s hard.

Maybe that’s one reason why I’m doing some of the things that I’m doing now. I’m doing a lot of startup mentoring and advising. I’m going to colleges and speaking to students. At least for the folks who decide that they really want to make it on their own, I’m here to help.

JENNIFER BROWN: It’s not for everyone, you’re right. That opting out of the corporate life, thinking it’s not for you, it’s a brand crisis for a lot of companies right now. I don’t know how they physically will be able to make the shift needed to address the day-to-day experience for all kinds of talent.

I’m working on that as well from where I sit. It is a big challenge, but on the flip side, as an entrepreneur, I celebrate that many people are trying to go it on their own. That will build the companies of the future. I, too, try to support that. It’s interesting, I have to walk a line because I also need to talk about which companies are really jumping into the conversation and putting their money where their mouth is.

Are there some examples of companies, large and small, that you might have a front seat to, that are truly putting this in action, and you know friends of all kinds of identities who are comfortable there, where they’ve actually really succeeded in building an inclusive culture?

ELISSA SHEVINSKY: I’m seeing companies that are doing a terrible job, but I actually can’t name a number of companies that are doing the best job.

Some of that is that I’m not actively doing diversity and inclusion consulting, so I’m not necessarily seeing the companies that are making positive change.

Right now, I’m mostly doing public speaking and writing. I’m thinking about my next book. To hear you talking about work at large is so interesting to me on the feminist front.

When I first put together Lean Out, it was groundbreaking. Everyone was saying that the problem with women in tech was a pipeline problem. Everyone kept asking me how to get more women in tech. No one was talking about the reasons why women are leaving. It was really something new to present these stories and to say that it’s on industry to do better.

Now, in 2017 heading into 2018, as I think about my next book and I think about wanting to contribute to feminism, I feel like there’s nothing left. We’ve told all our stories, we’ve spilled our guts. We elected a sexual predator to be president.


ELISSA SHEVINSKY: Silicon Valley and the film industry, name your industry, it’s full of powerful, white men taking advantage of the younger women around them.

I kind of feel like, “Is there anything left that I can say on feminism that isn’t said?” There isn’t. I’m done.

I think now if I want to say anything interesting on feminism, it has to be in another genre. What I’m thinking about now is about how women and other vulnerable people or minorities or people who seem a little bit different from the leadership are the canaries in the coal mine at work. There’s this deeper problem at work. Yes, there’s misogyny, but there’s something else.

If you look at Uber, it was a misogynistic place, but the root problem at Uber was something much deeper. Women had a bad experience at Uber, but it wasn’t only because of misogyny, it was because of these other deeply rooted problems with Uber as this dystopic, late-stage capitalism monster. (Laughter.)

JENNIFER BROWN: To put it mildly. Yes.

ELISSA SHEVINSKY: To use gentle language. I’m from Queens.

JENNIFER BROWN: I love it. Companies in general, and really it goes back to capitalism, it’s the short-term thinking. Unfortunately, it’s disincentivized; it’s against humanity. It’s against treating your people as well. It’s against creating deeper and respectful relationships with your customers and your markets.

I keep doing this work because I know the individuals in these companies are trying to humanize the product or the company, how they show up in the world, how they impact their ecosystem. Those are the people I try to be around. They, like me, we’re all change agents trying to work hard to shift these massive entities that are not fundamentally aligned or incentivized towards valuing inclusion, building trust, or sustainable operations in the world, versus eating up all the resources around you—human, environmental, and otherwise.

It can feel overwhelming. What are we actually talking about? It’s so much bigger than diversity and inclusion. I’m curious, is your book going to tackle the large question of what our economy would look like if it were full of healthy utilization of resources and triple-bottom-line companies? That would require a huge shift, a huge shift. Hierarchies, for example, that are bureaucratic and all about power accruing to the few, we’re still looking at org charts that are the same as they were in 1920. It’s crazy. When you think about it, we have not innovated around business. Yet, I don’t feel like the world is going to cooperate in a massive restructure of all of that.

ELISSA SHEVINSKY: Now you’re talking about the realm of science fiction. (Laughter.) Really. You’re describing the very important work of writing science fiction, of imagining a dramatically, radically different future.

Look at Star Trek. We’re actually seeing so many of the devices that were imagined on Star Trek, and we’re getting closer. We’re starting to see some of the same kind of egalitarian structures, some of them a little bit. People are at least thinking about them.

I’ve actually thought about what if I were to write science fiction as a way to express my interest in these utopic ideas and better political ideas? I’m not trained yet as a fiction writer, so it might be a little while. Maybe someone else will be doing that work, but I’m certainly thinking about these questions.

One option that I thought about for my next book would be to do some kind of anthology that would imagine what it would look like for things to be better. I’m not sure that I’m the person who brings that optimism to bear in my writing. When you meet me and you talk to me, I’m the most cheerful person. I run around singing and I’m kind of silly to the point of stupid. That’s my temperament. I’m extremely pleasant and cheerful day to day, but I like for my work to make you cry. I’m not going to be the one who will have that happy, shiny, utopic vision book. I want to talk about why people want to burn it down right now.

I’m seeing everything that’s wrong, and it seems to be important to express that. People like you and me, our friends, our colleagues—they’re living through difficult work experiences, and it is heartening and it helps to know you’re not alone. I think that’s the work that I do, to help people understand that this dystopic thing, this awful thing that they are suffering through, they’re not the only ones experiencing that. Lean Out does that by sharing these collective stories.

For my book on work, I want to talk about why, when you show up to work, you’re having a bad time.

JENNIFER BROWN: Yes. Well, we need the voices in your book to be the architects of that future world. You will lead differently, I believe, if you’ve been on the outside and you know what being “othered” feels like. You will be more conscious, often, not always, but you will be more conscious of how you build leadership teams, what kinds of companies you build, the purpose of what you’re building. You will have that lens with you all the time. That’s why people like you and I get depressed about the lack of female, queer, minority founders and VCs supporting those founders. Without folks at the table actually participating in building this, it is still going to be more of the same. People are still going to build in their own image.

ELISSA SHEVINSKY: There’s been this lightness towards harassment. I know people who have harassed other people. As you make your way in Silicon Valley and you start to make friends and you become part of the inner circle with folks who are leading, you discover that some of them have engaged in some pretty bad behaviors. I see how they talk about the things that they’ve done.

People will talk to me or I’ll hear about their stories harassing other people. You see the lightness of it, that they’re people who made their way to the top, and they don’t appreciate how other people see them.

You look at someone like Dave McClure, who was very sexually aggressive with someone in a work situation. The word “assault” was used. And you can see that he didn’t appreciate the importance of his role.

What happens is when some of us take on these roles as CEOs, as VCs, or in some cases as journalists, we enter into these positions of authority where the power differential is such that we need to be careful with other people because they look up to us, because they’re hopeful we can help them, and that creates the situation where certain kinds of consent are no longer really possible. It creates situations where a lot of these men in leadership didn’t appreciate the responsibility.

I came to understand that myself recently as I started mentoring young people and seeing how they looked up to me. They were so hopeful that I’d be able to help them. I saw that it takes an effort on my part to remember how much they’re looking for from me.

I think that there’s been this tremendous entitlement from the people who have been in leadership, in politics, in Hollywood, certainly in Silicon Valley and tech. And as new people come up who know what it’s like to be on the other side, hopefully, they’ll have more empathy.

Sometimes what we see is people who have been abused just want to become the abusers. You see that a lot. I guess that’s the thing that I’m scared of. My hope is that we can be as emotionally healthy as possible, and lead calmly from our hearts with a lot of care and empathy. That takes a lot of work, and not everyone’s up to it. Until we see that, I try to advise people how to navigate.

JENNIFER BROWN: Yes. There’s a whole journey that needs to be taken. Let’s just call it what it is: the leadership of most companies is white, male, cisgender, and heterosexual. I wrote an entire chapter in my book, Inclusion, about how to create empathy opportunities. Whether you’ve got to convince people with data, whether you need to share a personal story, somehow getting people to imagine how important their role is to others, that they’re being asked to set a tone. Everything that they do, don’t do, say, or don’t say ripples out from them when it comes to inclusion.

I always say, “Silence speaks volumes as well.” I’ve seen a lot of companies, most companies, most executives, remain silent on everything going on outside of the four walls of their company in society. You have to know that vast parts of your workforce are walking in the door carrying all of that with them and having their identity heightened with every step that they take, feeling very self-conscious and distressed if their community has been impacted directly by something in the news. If you’re an ally to that community and you strongly believe in inclusion, you’re equally disturbed if not directly impacted.

There is a total tone deafness at the top of the house in terms of being able to speak about this. Yes, it’s not your experience because you’ve had a relative degree of privilege, whether that’s your gender privilege or ethnicity privilege, but the work is taking people who are well intended and saying, “Intention isn’t enough.” How are you going to step forward and visibly and publicly talk about this, be vulnerable, admit that you’re still learning, and express over and over again that your task as a CEO or other executive is to create a workplace that you can bring all of who you are here every day? Not only that, we don’t want you spending energy dreaming about what you’d rather be doing or disassociating yourself because it’s too painful to acknowledge who you are and be reminded of your “otherness” in this place.

That’s a journey that needs to happen and a shift that needs to happen. Yet, executives don’t make the time for it, don’t care, think that it’s not an issue anymore. They are personally well intended, maybe they define them as progressives, which I think is part of the problem. There’s this assumption that inclusion is going to be a byproduct of progress. I think we’ve all had a huge reality check around all of that recently.

ELISSA SHEVINSKY: Right. I think a lot of people just assumed that things would naturally get better, but things get better because humans put in the work, because we try. In the absence of trying and working, we get the Trump Administration rolling a lot of things back. If we don’t fight for technology and technology spaces to be warm, inclusive, and have empathy, then you end up with Reddit and Twitter at their very worst. It takes a lot of work to create safety. It takes a lot of work to make things that are really good. For a long time in technology, when we’ve thought about challenges, we’ve thought about technical challenges or we’ve just assumed that things would be fine. Some of that is the people who have been making these products have been white men who haven’t really been experiencing harassment or they don’t know what it’s like. We need to put the work in. It’s so important right now.

JENNIFER BROWN: That’s right. The storytellers in Lean Out do talk about the range of male colleagues. I loved how many people talked about their male colleagues who are true allies and how they’ve learned not to put people into a box based on what they see, and also the patience of bringing someone along and building the calling-in culture versus the calling-out culture.

I write about that a lot. I have really mixed feelings about the Google memo writer being fired in the way that he was. I wrote a piece called Calling In a Few Good Men.

I know you’re passionate also about call-in culture. Could you define call-out culture, call-in culture, and tell us: How is call-in culture operationalized? How do we invite the imperfect participation of folks who want to do more, want to be better leaders and human beings, and not shame them in a counterproductive way that shuts down the whole thing?

ELISSA SHEVINSKY: Sure. This issue is so close to my heart because my former co-founder Pax Dickinson, recently was part of a neo-Nazi march. I think it was the one in Charlottesville. I don’t remember, not Charlottesville, but there was something afterwards.

I’ve gotten some strange messages from people who have said things to me. They want me to justify the fact that I worked with this person many years ago.

What I have to say about that is when I was working with Pax, he would call me on the phone before he would post a tweet to ask if I thought it was okay. We had a women-led company, I had the majority of the shares in Glimpse, we brought in Kelly Hoey to be on our board.


ELISSA SHEVINSKY: I love her. And we were selling “lady boss” shirts to help support Glimpse, and everything that we were doing in our company was very feminist.

Pax was an outspoken feminist while we were working together because he was championing me, and he totally took my side anytime anything came up. I remember him shaking his fist and saying that something had happened because of sexism, and he meant it at the time.

Even if he hadn’t fully meant it, he was coming on board. He was supporting and championing me in everything and every way that he could. He also brought me along to his side a little bit more, I’m for sure more right-wing for his influence. It goes both ways. That’s what it is when you’re close with someone, you influence each other.

I look back and I think about the impact you can have on someone. I remember Pax really wanted to be a mainstream CTO. We were hoping to build this company and sell it to Facebook or have some kind of “acqui-hire” so we could level up. We would have loved to have had an IPO, but we were just trying to make our way in Silicon Valley and level up. All he wanted was just to be part of the tech community.

Then at some point he was blacklisted. He just couldn’t get a job anywhere. The only person who would work with him was Chuck Johnson, who is extremely comfortable expressing his racism. I don’t really have to tell everyone who Chuck Johnson is.

I think about what happens when someone like Pax, who wanted to be part of the mainstream, is completely shut out. I don’t feel bad at all about these times when I worked with people who were maybe a little bit outside and tried to bring them in. I think that’s a good thing to do, to the extent that you want to build a society that includes everyone. You can’t just throw people away, right? You toss out James Damore, who I’m really glad was fired from Google, and you toss out a dozen other people, the problem is now they have no one but each other and they’re going to organize. Now you have a really dangerous group of 12 people.

I would feel a lot better if we all tried to work together to understand each other in these earlier stages. The truth is, yes, those folks are going to shift the mainstream to the right maybe a little bit, like Pax definitely shifted me a little bit more to a very hardcore libertarian right, maybe further than that. But I shifted him a lot, too, and I think that’s a worthwhile price to pay. We should figure out before people become violent, before people become really extremist.

The point where people are neo-Nazis, the point where people are spouting hate, at that point, we need to deal with that in a swift way. That’s why we have prisons, that’s why we have people talking about punching Nazis. I’m not saying that you need to let all of that slide, what I’m saying is that there are people who still want to be included, still want to be in the mainstream. We can bring them in and make them allies.

I have one more story about this that is very sensitive for me, but I think it’s important to tell. I’ve been pushed out. I started a Kickstarter with Tara Wheeler, and we wanted to do diversity and inclusion consulting. Erica Joy said no. She called us out on Twitter and scared all of our backers. It was because she said we were doing “white woman feminism.” But we had a lot of other people, it was a very diverse group. I had just finished Lean Out, we had all kinds of people, women of color, a trans woman, lots of folks who were going to be part of this with us.

I think there’s a real problem here. If you’re not pure enough, if you’re not perfect enough, or if you’re not the right identity, sometimes you’re not allowed to be an ally or you’re not allowed to be in the progressive movement.

At that time, I needed a job. I remember that. I had just come out of my startups, and I really needed money. I also wanted to work, to make an impact, and I was hoping to do it in diversity and inclusion.

When Erica Joy came at me, we couldn’t do the Kickstarter, and I ended up working for Brandon Eich. Brandon Eich was the first person to make me a real offer, and I went to work for Brandon Eich at Brave.

That’s illustrative. I wanted to just be a champion for diversity and inclusion, and I was told that I couldn’t do that. I wasn’t good enough, I wasn’t right enough. I’m choking up thinking about that. I think it’s such a mistake. I think we need to take people like me who want to be allies and bring them in. The answer wasn’t to say that people shouldn’t support me doing diversity work. I think Erica should have talked to me. Should have gotten me on the phone and said, “How can we make your work better?” not, “How can we kick you out?”

If I’m getting kicked out after producing Lean Out and after having a great reputation as a feminist, think of all the men who we could bring in who could be helping us and we’ve pushed out. We shouldn’t be throwing people away.

JENNIFER BROWN: Oh, my God, you just gave me a whole different way to look at call-out culture that we do to each other. I personally believe it’s a scarcity mentality versus an abundance mentality. We think the pie is finite because we’ve had to struggle so much to have that piece of the pie. It becomes a habit or a muscle, then we exact that penalty on others, when really we should be joining together.

I write in the first chapter of my book about the phenomenon of the white, and sometimes male, diversity officer in companies. I’m sure you’ve probably followed the very, very few. I can count them on one hand. Some of them aren’t in role anymore, and there’s a little bit of switching around, but the assumption that you can’t do the work because you’re not in a particular identity and that is not your direct story is something I’ve been very keenly aware of, obviously because we profess to be able to guide companies on this.

We live it every day, but I’m always aware of my color, my socioeconomic background, being able-bodied, but I’m also aware of my other stigmatized identities where I have to navigate all of the complexities that go along with that.

In my keynotes, I’ve now started to just call it out at the beginning. I don’t want anyone to be able to use it as a weapon against me. I want to admit that I’m learning. I want to say I’m doing my best, and here’s the lens of privilege that I’m coming from as I talk about this, as I teach about it.

In the audiences that I’m in, which are white, male, senior-levels of companies, I find myself being a very effective bridge because of the acceptability of what they see when they look at me in their minds. I can have the conversation and get in the door and win trust quickly for no earned reason, just the fact of the packaging that I happened to be born in. Yet, I carry all of this knowledge and awareness of all these other communities and the points of view I want to represent.

It’s a really interesting situation. I know what you’re talking about, though, because I have wondered, “Do people think I can’t do this work?” You literally wrote the book highlighting.


JENNIFER BROWN: You took the step that nobody else has taken, which is to tell other people’s stories, people who don’t look like you or share your identity, giving them a voice in this dialogue. I can’t imagine more cred than that.

My friend Kenji Yoshino, who was on the podcast, calls it the “pain Olympics.” I’m really sorry that we’re still obsessed with the hierarchy of pain in this community.

ELISSA SHEVINSKY: We need to do a better job of building coalitions and bringing people in. I’ve been thinking about this so much as I’ve watched the alt-right come up because they’re still recruiting me. I still get DMs from people who want to convince me that I’m alt-right, and that’s because I was friends with Pax for so long and because I was libertarian in a very strong way. There’s a lot of proximity there.

I look at how they’ve been recruiting me. They’re really hardcore. And I think that the progressives, the lefts, the feminists, we need to do that same thing. We need to reach out to everyone. There’s this idea on the alt-right of “red pilling” people. You know? And that’s something that people are really proud of. They’re really proud of how many people they red pill.

As feminists, we’re proud of how many people we push out. No. We need to “feminist pill” people. We need to be recruiting.

Yes, there is this idea where there are a limited number of spots in the C suite, and you kind of have to claw to get there. But we’re trying to build coalitions. We’re trying to build a movement. There’s no clawing to get to the top of the movement, we need to bring everyone in. We need to bring in as many people as we can to be on our side. We need to bring people to our team. For me, that’s the most straightforward thing.

Yes, that means we have to share a little bit, but ultimately it means you’re bringing in people who will empower you. My first job out of college was as a lobbyist and a grassroots organizer in D.C., so that’s how I see this. I see this from an organizer perspective, a political perspective. We need to bring everyone in.

JENNIFER BROWN: It’s so true. We don’t have time to obsess about what makes us different or create that hierarchy or replicate the patriarchal thinking, right? I think what we’re doing is literally inflicting what has been inflicted on us, and we’re passing the abuse along. That is what it is. We can’t afford to do that.

Your book struck me in so many ways. I loved the first-person, honest narratives from queer women, from women of color in particular. Reading this, as a white woman, was transformational for me. I knew it was the exact kind of learning that I need to continue to do, apply myself to, and make time for, to be an ally.

It’s interesting to speak of myself as an ally because I’m a member of the LGBT community, like you. So I did want to talk about your coming-out process. What was the order of you deciding, “I’m going to be uncompromisingly myself as an LGBTQ person”? And then writing a book, probably even challenged you in your sense of sexual orientation and gender identity and fluidity in all the ways that people define that, right? I know it’s been a journey for me, learning how not straightforward it is. It’s interesting to be LGBT and also strongly identify as an ally. Right?

ELISSA SHEVINSKY: Yes. Identity is such a difficult and tricky thing. For sure, I have a lot of privilege, and there are people who have it very difficult right now. I try to remember that. I try to remember that they’re in a lot more pain than me, and that’s sometimes why it’s hard for us to all come together. But that said, you asked about me, so I’ll talk about myself for a minute.

JENNIFER BROWN: Yes, please.

ELISSA SHEVINSKY: For me, in 2015, I had just had it. I was in this classic, you could say “iconic” or maybe “cliché” angry feminist moment. And I was just like, “All the men just need to step back.” (Laughter.) You just need to step back. I am not here for your sex, I am here to work, and for whatever reason, you all cannot show up professionally with me. And I am going to make this as clear for you as possible.

I remember that time in my life I really wanted to run my companies, and I couldn’t believe how sexualized I was all the time. I guess I should be appreciative that people find me attractive. You know? I tried to have moments, I’m like, “People think you’re cute. That’s great. People want to date you, they like you. Try and be happy about that.”

But it’s not a happy thing when it’s interfering with very basic stuff, it’s disrespectful. It’s disrespectful that women are showing up in a professional way and men look them up and down and say, “I don’t see you, I don’t see your credentials, I don’t see your talent, I just see how lonely and horny as a white, male executive I am.” I was just so done with that.

It’s been really nice since that article about me came out, people absolutely have taken a step back. It’s really been life-changing that way. There are a lot of things that are hard. It’s been very lonely for me being an executive, that’s a lonely place to be, and it’s been interesting to be a queer woman in this moment. I have so much privilege, and in other ways, I’ve had to fight so hard. But if we’re going to bring it back to Lean Out, the thing that I did there that I’m proud of that was really good was I understood the importance of other people’s perspectives, and of having empathy. I somehow managed to gain the trust of enough people to trust me to put that together and to share their stories in a vulnerable way.

I think that’s one thing that I really do bring to that table that ability to be self-aware and have some empathy about the situation.

JENNIFER BROWN: Yes. I just want to add, we have started to call it the “gift of being LGBTQ” in some of my leadership programs. We get into a room, we close the door, it’s a safe space, and in the corporate context, we talk about what has been gained by coming out, embracing yourself, bringing your full self to work, to all of your interactions, standing up for yourself, really finding your voice, and believing that everything is available and possible to you, and that sometimes we are our own worst enemies as well?

I physically see people cast off this really heavy weight in front of me. It’s this beautiful moment, and it makes you realize that it’s been very liberating in some ways to be on the outside. It teaches you all sorts of resilience, resourcefulness, and emotional depth and for difficult reasons. I wouldn’t have chosen to learn the things that we learn for those reasons, but what you end up with as a human being is this emotional range, depth, and courage that I heard loud and clear in all the stories that you compiled.

We’re all along that journey at some point. Some of us are still just poking our head out and saying, “Is it okay to be me, and is it beautiful to be me?” And then others of us are on the other side, trying to pull other people out and give that back to them.

You and I were talking earlier about being in this position now where we’re teaching and we’re actually imparting this insight and trying to shorten the runway for people in their own journey. It doesn’t need to be as long for them as it was for us. When you get to this age and you’ve seen this, you’ve written books, people look to people like you and me and say, “Why am I struggling so much? Am I just looking at this in the wrong way?”

There’s some self-exploration and uncovering that needs to go on for many of us, but I have found it empowering to think about the gifts of the outside that have informed me, and shaped and forged who I am. What does that represent for others that they really need to see every day? That’s why I always try to come out as many times as I can. And it’s the shock and awe. You know? You can imagine.

ELISSA SHEVINSKY: That’s awesome.

JENNIFER BROWN: Yes. I walk around the stage in heels. I’m more comfortable in a feminine expression, for whatever reason, I don’t really understand all that.

ELISSA SHEVINSKY: Right, we’re both so femme.

JENNIFER BROWN: I know. We’re really femme. And it’s a total shock and awe. I’ve got to say it, otherwise I can pass every moment of my life. But when you do that, I think what you’re alluding to, you took your power and you said, “I am not here in service of anything but the work for you. This is a boundary, this is who I am, this is what’s not available, and let’s focus on what we’re here to focus on.” As a woman, taking all that off the table in a man’s world, taking it off the table and saying, “That is not something that’s going to be discussed or in the air or anything.” I think it clears the way for some possibilities, while introducing other difficulties.

Tell me, if you refer to yourself as a femme, have you found it oppressive, but also liberating relating to your interactions?

ELISSA SHEVINSKY: Can you say that again?


ELISSA SHEVINSKY: I’m not sure what the question is.

JENNIFER BROWN: It’s probably not a question, it’s maybe some solidarity around being femme. Being LGBTQ, being feminine-normative presenting, and claiming our power and the dynamic of actually being true to yourself is actually liberating and gives you that ability to get to work in a man’s world.

ELISSA SHEVINSKY: I had a date a little while back. I remember specifically dressing in a feminine way, and it was a remarkable and kind of confusing thing for me. That’s because I’d been really trying to de-feminize myself at work. I did that as a way to draw another line.

I started wearing Converse and I stopped wearing skirts. I went to a lot of effort, and I’m not the only woman who’s done this, to look as professional as possible, but also as boyish as possible. Again, another way of taking that off the table, another way of trying to draw clear lines. That’s been really helpful.

Actually, I have a lot of good business experiences showing up where I’ve helped to draw clear boundaries. I certainly don’t want to blame people for not drawing clear boundaries because I think it’s on the people in power to understand that they have that authority and to take it seriously, but it’s been really good for me to show up making things extremely clear.

I was always a very feminine girl as a kid. I was a really feminine kid, and I think that my temperament and personality are very feminine, almost a little delicate. I’m five-foot-one and 100 pounds.


ELISSA SHEVINSKY: Yeah, right? There’s something extremely feminine and vulnerable about me in person, but then I kind of “butch it up” for work. (Laughter.) I want to show up and be that lady boss and be strong. There are pieces of myself that I don’t bring to work because I haven’t figured out how to integrate them. So this feminine, vulnerable side only gets show to my most inner circle and I guess all your podcast listeners. (Laughter.)

JENNIFER BROWN: I love that you’re sharing that. I feel the same. It’s funny, bringing your femininity – however we define that – into the business world is a thing. We all make choices about how we present our gender based on how we want to play the power game, our sense of safety, and whether my colleagues are going to be able to hold all of me in ways maybe they think are contradictory.

That’s why, when I come out on stage and I tell my story, in that moment of cognitive dissonance, I have the power because I’m giving a keynote, right? I’m safe, I’m on the stage. I think to myself, “This is so small compared to the daily battles that people fight, but it is the least I can do to be honest and show as much of myself.”

I’m always challenging myself, “What else can I show?” I get that question a lot from the audience, “Why do I have to bring this into work? Does it really matter? I’m ashamed of it, it’s something I don’t want to think about or it’s in the past.” There’s a lot of resistance around whether it’s relevant. When you say, “Bring your full self to work,” why? What if that makes me feel unsafe? That’s a very valid point, and something we need to be grappling with. We need to be thinking about it and noticing it. It’s not about right or wrong, it’s going to be different for each one of us. Your delicacy, your stature, your physical size or making choices about wearing sneakers instead of heels, how you wear your hair, how you speak, how powerfully you gesture—all of that, these many choices we make, that’s another piece that’s not appreciated by others. It doesn’t even occur to them, and they never have those moments of cognitive dissonance, choice, or covering.

Increasing the empathy around that would go a long way. I believe showing up as all of who you are, including those physical attributes and how you view and express your femininity is incredibly important to show that someone can look like you, act like you, sound like you, doing the technical work that you’re doing, and being a lady boss.

ELISSA SHEVINSKY: This reminds me of something very brave that I’m trying to do that I haven’t spoken about so much, but I’ll tell you and your listeners. I am trying to write my memoir. I’m trying to write the stories of all the crazy things that I did trying to come up in Silicon Valley, and to explain myself and to be vulnerable.

The whole time that I was being a startup CEO, there was so much posturing. That’s always felt like part of the job for me as a leader that I would show one slice of who I am. I’d show that lady boss piece, and then the vulnerability, the mistakes, and all the rest, I tried to always gloss over. That’s what we do, right? We do our perfect Instagram posts, but as a leader, it’s very difficult to be vulnerable.

Now, I’m taking a step back and trying to bring all of myself into my public life. It’ll take two years to write this book. A good memoir really takes time, revision, edits. It’s a new writing style for me, and it’s the scariest thing I could do, which is one reason why I’m so excited to do it. I want so much to bring all of myself into my public life.

JENNIFER BROWN: Me, too. Me, too. So many of us need to see not only the finished product of doing that, but the journey to that place. Show your work, be public about it. Even though you don’t have that answers, that alone is going to be inspirational to countless others who are asking the same questions.

I love that you’re writing a memoir. I always think we don’t have to wait until we’re a certain age to write a memoir. So many of us have been through so much, and we can’t wait, we don’t have time to wait to teach and to share. There are generations at stake, in particular, young women, trans women, women of color, and frankly, white women, too, who need to understand your story and understand the lengths to which you’ve gone to build your ally story. I’m sure that will be a part of your memoir, and I look forward to reading it. Take your time, but at the same time, don’t take too long because the world really needs it.

ELISSA SHEVINSKY: Thank you for the encouragement. We need to encourage each other. You’re so supportive, I really appreciate that.

JENNIFER BROWN: Elissa, thank you so much for your work. Let’s recap for our audience. I know we’ve talked a lot about your book, Lean Out, it’s on Amazon. Where else can people follow your work and support you?

ELISSA SHEVINSKY: ORbooks.com is a good place to buy Lean Out. I need to set up my own Amazon shop, and I should do that this week, maybe I’ll even do that today. People can buy discounted copies of Lean Out through me. I’m able to get wholesale rates. If folks wanted to do a book club or order a few copies, I can send over signed copies at a discount.

Folks can find me on Facebook or Twitter, my DMs are open, and I’m happy to chat.

Right now, the best way to support my work would be to buy and read Lean Out and to share it, or to bring me to your company or college. I am on this book speaking tour right now, which is really wonderful. I’m able to go to schools, I’m able to go to companies, and I’m doing a mix of paid and pro-bono work depending on the venue.

If folks are listening to this and you work at a company where you think it would be fun for me to come in and talk about how to make things better, or we can get together and gang up on your boss, sometimes those talks go very well, too. (Laughter.)

There’s a talk of me at Google. The first thing I said is, “You all haven’t read my book, have you?”

JENNIFER BROWN: Otherwise I wouldn’t be here. I love it.

ELISSA SHEVINSKY: I wouldn’t be here. Sometimes at these companies like Google, things are divided. There are people inside the company who want to make things better, they really do, and they’re happy to have a community forum about that.

This is the most exciting thing I’m doing right now, going into these companies and giving these workshops and talks. I’d love to do more of it. My goal was to do at least one talk a week, and that’s about set. I’d like to push my limits. I want to see hard I can work.

JENNIFER BROWN: I think you have a lot of capacity.


JENNIFER BROWN: Thank you for everything you’ve done, Elissa. I hope everyone loves the book as much as I did and absorbs the wisdom of it. In particular, I hope everyone does some deep thinking about how we can be more supportive of others, and if we have any privilege at all, how we’re using it on behalf of others. You’ve done that, you’ve demonstrated how it’s done, and I thank you so much.

ELISSA SHEVINSKY: Thanks again for having me on the show.


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