Shall we?

Full disclosure: I basically have handlers who will make sure I don’t say anything too off-color. But generally, the only things I avoid saying are partisan things because I run a non-partisan organization. Talking about being a woman in technology, or a gay woman in technology in San Francisco, is not partisan.

Or a “loud-mouth lady gay,” as you called yourself in your application?

Yeah. Being a loud-mouth lady gay led to me realizing that, “Oh my God, I’m no longer suited to work for other people.” The last boss I ever had said that she thought I would do much better working by myself. She was correct.

Okay. So let’s start from the beginning, Tell me a bit about your early years and where you come from.

I am from Brooklyn. I’m a fifth generation Brooklynite. My family has been there since 1890 on the maternal side and since 1910 or so on the paternal side. So we’re pretty run-of-the-mill Eastern European Jews who left Europe when Europe became less-hospitable. I’m from the part of the Brooklyn where the accent is from and where hipsters still don’t live. So when you think artisanal crafts, do not think of the Brooklyn that I grew up in or the Brooklyn that my mother currently lives in. My mother would have no idea by what you meant by “artisanal soap,” “artisanal candles,” “artisanal gefilte fish.” She just wouldn’t know what any of that means.

I respect that. What part?

Bensonhurst.

Bensonhurst, I do not know Bensonhurst.

Bensonhurst is where the “Honeymooners” took place, where “Welcome Back, Kotter” took place, and where “Saturday Night Fever” took place.

Wow, that’s really amazing. No, you don’t have an accent, but you have the East coast swagger, which I appreciate as a fellow-East coaster.

Thank you.

When did you first get interested in tech, and separately, when did you become interested in politics?

Those actually overlap a bit. I’m older than I look, so the first time that I used the internet was my first week of college. This was 1995 and I was definitely an early adopter. I was one of the first people in my circle to learn HTML, and I took some entry level design courses in college.

I first became strongly interested in politics the night of the 2000 Presidential election. I was with a group of friends in North Hampton, Massachusetts, and we were watching the returns. When Florida went blue my friends were like, “Okay, great, Gore’s president,” and went to sleep. I was like, “I’m just going to stay awake and watch the rest of the returns.” This meant I was awake and alone when Florida was suddenly red.

“Being a loud-mouth lady gay led to me realizing that, ‘Oh my God, I’m no longer suited to work for other people.’ The last boss I ever had said that she thought I would do much better working by myself. She was correct.”

Keep in mind it was the middle of the night in Florida when this happened. First the state was declared for Gore and then — what was the story? — they found a truck filled with ballots for the Republican candidate, George W. Bush. This was a very surprising thing to happen in the middle of the night, and a very surprising thing to happen in what was an overwhelmingly Jewish section of Florida. And then the recount dragged on forever and wound up at the Supreme Court.

I think that night was the first time I became cognizant of how important voter turnout is. The presidential election should never come down to multiple recounts of ballots in a single county in America. At the same time, I was young and doing other things with my life. In 2004, I decided it was time to get more involved in politics. I met Sharif, a man who was staring a project called Swing the State. People would register as volunteer online with Swing the State, and Sharif would help them travel into swing states to do voter registration and get out the vote work. I told Sharif I wanted to help, and that was that. I was somewhat technical at that point, and this was a highly technical project. It was really just Swing the State and MoveOn.org that were organizing volunteers online and then deploying them on the ground back then. Swing the State was my first political tech project. I just kept going from there.

So, at first, you were working in tech, and politics was a hobby?

No, actually, I was investigating police misconduct for the City of New York.

Okay, walk me through this whole thing. I’m going to stop talking. You take me from the beginning.

My career path makes absolutely no sense. Let’s set the stage. It’s 2000 and I lived in Western Mass, because that’s where I thought young lesbians lived. In 2001, I came to my senses and moved back to New York, because it turned out that Western Mass is actually where middle-aged lesbians live. So, I moved back to New York, and puttered around for a bit. In 2004 I got a job investigating police misconduct for the City of New York. This was an awesome job: I had a badge, and cops had to answer to me, and that was great. I met Sharif that year and started running Swing the State in my spare time with Sharif and about ten of our friends. This was a fiercely partisan project. We were like, “We do not want George W. Bush to win re-election. That would be terrible, we must put an immediate end to this.”

The 2004 election did not work out the way we wanted the 2004 election to work out. I continued investigating police misconduct until 2007. Then I got a phone call from a friend from college and he offered me a job at MySpace.com. I literally hadn’t heard from this guy in years. Do you remember MySpace?

I was very active on MySpace. It took me a long time to get it out of my top Google results.

Oh, that’s really funny. I was active on Friendster and then someone I worked with investigating police misconduct literally said to me, “Oh that’s right, you’re old. You people are all still on Friendster. Young people are on MySpace.” And I was like, “I’m young too!” So I created a MySpace profile that I literally never checked. I never really used MySpace until my friend from college called to offer me this job. I was wholly unqualified for this job —I feel like this is a key part of this story. But he knew that I had been running a civic tech project, and as far as he was concerned this meant i worked in technology. I was like, “No, no, no, I have passion projects in technology.” But, you know, this was 2007 and you could accept jobs that you weren’t remotely qualified for. So in 2007 I stopped investigating police misconduct, moved from New York City to Los Angeles, and started working at MySpace.com when MySpace was pretty much the center of the online universe.

I got to LA and realized I didn’t actually have any friends in LA. This meant I had a lot of downtime and decided it was time to start another election project. And that’s where Long Distance Voter comes from. From me not having any friends in Los Angeles.

“This was 2007 and you could accept jobs that you weren’t remotely qualified for. So in 2007 I stopped investigating police misconduct, moved from New York City to Los Angeles, and started working at MySpace.com when MySpace was pretty much the center of the online universe.”

That’s beautiful.

It’s amazing what not having friends will do for your spare time and your creative drive. So backing up a bit, in 2004 I thought that the best way to increase voter turnout was to register more voters. This was a very common thought back then. So Swing the State and our partner groups, like Acorn and America Coming Together (rest in peace both groups), were part of this massive, nationwide, voter registration effort. At the end of the day, it didn’t seem to have much of an impact on turnout. Progressives were out registering conservatives four to one, but we certainly weren’t winning elections.

By 2006, I started to wonder if voter registration was related to voter turnout in any way. I’m not an academic, I didn’t have an actual funds to study this, but my gut told me to focus on something other than voter registration. I decided that my next project was going to focus on some group of people who were already registered to vote, who were highly motivated to vote, and who had some sort of roadblock that I could clear using the internet. If we’re being honest, I mostly wanted to stop doing door-to-door voter registration. I’d done a ton of that in 2004 and 2006 and it was just terrible. So late in 2006 I decided I would never again carry a clipboard.

Anyway, so now it’s 2006 and I’m in Vegas—where all great ideas are born—at a brand new political conference called Yearly Kos. A group of us were sitting around, and my friend John wanted to go ride a mechanical bull. Everyone was drunk, and I was like, “Do not go ride a mechanical bull. This is a terrible idea. Instead of riding a mechanical bull, I need you to help me figure out something.” And John was like, “What?” I was like, “I need to come up with a group of people who are already registered to vote, who are highly motivated to vote, have some sort of roadblock that we can clear using the Internet, because I really, really do not want to have to go door-to-door every again.” And he was like, “What about absentee voters?” And I was like, “What?” And he was like, “When I did absentee in college, it was really confusing and I’m still not sure if my absentee ballot was counted. Is anyone running an absentee ballot project?” And I was like, “I don’t think so.” And he was like, “Great, we should do that,” and then went off to ride this mechanical bull. And that is Long Distance Voter’s origin story.

“I’m working at Myspace during the day as a product manager. So during the day I’m identifying what people need from the internet, and what sort of tools we should build, and how you could run an engineering team. At night, I’m working with my friends, and we’re doing our nerdy voting project. I continued this pattern of having working as a product manager during the day, and volunteering with my friends to save democracy at night, through several jobs.”

I don’t remember how riding the mechanical bull worked out for John. He obviously lived to the morning, because we were all fine the next day. Anyway, that conversation happened in 2006. In 2007, I moved to Los Angeles, had no friends, and reached back out to John about his absentee ballot website. John and I recruited a bunch of our former coworkers (we had all investigated police misconduct together for the City of New York) and we started building the Long Distance Voter website. We had $5,000. I think there were ten of us—there were ten of us. Everyone took five states. We called the Secretaries of State, we asked them to walk us through it. We called every Secretary of State in America, and we asked them how you voted absentee in their state. (This is incredibly boring, I realize. Just picture us all investigating police misconduct, that makes it more exciting.) We built what was essentially a Wiki, with one page per state, and we had our first half million visitors within six months. So, we were like, “Alright, let’s keep doing this. We’re awesome.” And so we kept working on the site. Everyone was a volunteer.

We added more features to the site because users asked us to. People asked, “Hey, how come you don’t have a voter registration tool?” So we threw the Rock the Vote voter registration tool into the site, and quickly became Rock the Vote’s number one partner — in terms of registrations — out of 500 groups using their tool. People started asking us when early voting happens, so we created early voting page which is still the first hit on Google. So we just kept going with the site.

Meanwhile, I’m working at Myspace during the day as a product manager. So during the day I’m identifying what people need from the internet, and what sort of tools we should build, and how you could run an engineering team. At night, I’m working with my friends, and we’re doing our nerdy voting project. I continued this pattern of having working as a product manager during the day, and volunteering with my friends to save democracy at night, through several jobs.

That’s amazing.

Thank you. It makes no sense though. Everyone in voting assumed this was my full-time job. I’ve been Debra Cleaver from Long Distance Voters since 2008. At the same exact time, I was Debra Cleaver from Myspace, then Debra Cleaver from Truecar.com, and then Debra Cleaver from Change.org. It’s like I was Batman, but less cool. I had an election alter ego who did not get to wear a mask and a suit.

I feel like we’ve I’ve heard a lot of exciting things you’ve worked on, have we missed any of the really proud and exciting things?

No. Honestly, spending my twenties investigating police misconduct for the City of New York was awesome. I would also say—and this is a fact—that the New York City Police Department is the best trained, most heavily regulated, police department in the world. The fact that New York City has civilian oversight is really meaningful. A lot of the nonsense that happens in other places does not happen in New York, or doesn’t happen without immediate repercussion. New York City’s Internal Affairs Bureau is the model for Internal Affairs departments throughout the country. Living outside of New York, I’m astonished that there are police departments with no civilian oversight. If the police are only accountable to themselves, and not to civilians, then we are living in a police state. That is the literal definition of a police state: one where the police are only accountable to themselves. In New York City, the police are ultimately accountable to the civilians that they police. That doesn’t seem to to be the case outside of New York. New York City is certainly not without its racial and systemic biases, obviously, but it never felt like the wild west. Outside of New York, things seem nuts right now in terms of police misconduct.

What have been your biggest struggles over your career path, be it directly related to work or even personal? What have been the hardships you’ve had to overcome?

I loved investigating police misconduct. It was just awesome. I was also our union shop steward. In addition to investigating police misconduct and running Swing the State with my friends, I also engaged in a three-year battle with management. I filed all these large group grievances against management, and won them all, and that was just amazing. So I had this really amazing time, investigating police misconduct, and being a bad-ass, and driving the management nuts, and being a union shop steward. And then one day I realized, “I need to get the hell out of government.” Once you win massive group grievances, your career is pretty much over, you’re black-balled.

“Working at MySpace was amazing. If you saw a woman in the engineering department, there was a very good chance she was in charge of her team. The MySpace technical team was run by women. So my introduction to working in tech was to have all these bad-ass, fierce, unapologetic women running the show.”

So, MySpace came at the exact right time. Working at MySpace was amazing. If you saw a woman in the engineering department, there was a very good chance she was in charge of her team. The MySpace technical team was run by women. So my introduction to working in tech was to have all these bad-ass, fierce, unapologetic women running the show. The women were incredibly smart and really scary, and they’ve accepted me as one of their own, and I always had a great time at work. The guys at work would tell me that that wasn’t the case at other tech companies and that their wives and girlfriends had a much harder time working in tech. And, I said, “Oh, that’s weird, because I feel like MySpace is female dominated.” And they were like, “Well, MySpace is the exception to the rule.”

And then, I went to work at TrueCar.com, which was an automotive tech company. It was male dominated, but still a really wonderful professional experience. It wasn’t fun, the way MySpace was fun, but everyone was a professional. We came in, we did our work, and we were all paid well, so we were motivated by money, not necessarily our love for the automotive industry. Even though it was a predominantly male staff, I never thought it was a boy’s club. And then I moved to San Francisco, and the San Francisco tech scene was unlike anything I’d ever seen.

Tell me more.

I came to San Francisco tech companies and I suddenly was surrounded by people who had never heard of professionalism. Everything from “please show up to work on time” to “please do not tell jokes during the day, this is inappropriate”. I’ve never considered professionalism and fun to be at odds. I was like, “Professionalism is what enables a diverse group of people to together.” My team at Myspace was widely regarded as one of the happiest teams in the company, and Myspace was a big company. My team was 50% loudmouth white homosexual, and 50% somewhat quiet engineer who had grown up in India. So this was not a group of people that you would expect would really gel, but we did. The quieter coworkers kept the loudmouths from being bonkers and off the wall. And the loudmouth homosexuals made things light hearted and fun. And we were absolutely the happiest team in the company, and professionalism was why we could work together. Ken, my lead developer, is a wonderful person, also a devout Christian. So just during the day I didn’t make off-color comments about religion, because that would inappropriate. We just didn’t make off-color race or gender jokes in general, cause that would be inappropriate. So we had this team at Myspace that was diverse in terms, and race, and religion, and country of origin, and still managed to laugh all day, every day.

Then I moved to San Francisco, and suddenly things were just not funny. It’s not funny when you’re in HipChat, and someone is literally telling dick jokes. And it’s not funny when you’re the only woman on a team of 35. I’m used to having more men than women on a team, but I’m certainly not used to having 35 men and one woman. And I’ve found that when you build a homogenous team, people forget all about professionalism because they don’t have to moderate their behavior to accommodate people who aren’t exactly like them.

“Then I moved to San Francisco, and suddenly things were just not funny. It’s not funny when you’re in HipChat, and someone is literally telling dick jokes. And it’s not funny when you’re the only woman on a team of 35.”

I’d never actually articulated to myself, ‘I work in a boys’ club’ until I started working in SF. I’m a short-haired, loud-mouthed dyke and I’m very comfortable with predominantly male environments. But a boys’ club is very different beast entirely.

You might need to pepper me with some questions now because good Lord, do I have stories. So many stories.

What have some of your experiences been like?

Okay, some of the stories are just kind of hilarious. I had one software engineer who would groom at his desk. He’d trim his nails and comb his very long beard and it was just kind of weird. And his hygiene just wasn’t great. Really sweet guy, but terrible hygiene. And he would take off his shoes and his feet smelled terrible. I just pulled his boss aside and was like, “You got to deal with this. We have to have a shoes on policy at work.” His boss looked pretty uncomfortable, but there was no way I was going to deal with that mess. I told the boss, “Maybe you can talk to the boys about hygiene. You don’t need to say any of us have brought it up but it would be great if people could bathe once a week. That would really be great.” That’s a funny story: you don’t expect to have to tell a 40-year old man to bathe, but not the end of the world.

“I’ve found that when you build a homogenous team, people forget all about professionalism because they don’t have to moderate their behavior to accommodate people who aren’t exactly like them.”

Less funny story. At one job a software engineer punched another software engineer in the face at the holiday Christmas party. Boys will be boys, I guess. One of the boys was mouthing off at another one of the boys, and the second boy had enough of it and punched the first boy in the face. On one hand, I would say a lot of us had wanted to punch this guy in the face. On the other hand, but you may fantasize about punching a co-worker in the face but you don’t actually do it. And they weren’t boys—they were grown men and we were at the company Christmas party. There was an open bar, and everybody was drunk and dancing, and out of the corner of my eye, I see people who look like bouncers and I think, “Those look like bouncers.” And then I immediately realize those are actual bouncers because one of the engineers just punched another engineer in the face. So that wasn’t great [chuckles].

I was like great, “I’m getting out of here.” And the CEO literally catches me as I’m leaving and he’s like, “Hey, what just happened?” And I was like, “Well, one of your engineers just punched another one of your engineers in the face.” And he was like, “Why?” And I was like, “I don’t know. I haven’t ever punched anyone in the face so I can’t really imagine.” And he’s like, “But you have to have some idea.” And I’m like, “Well, first, your engineers are a bunch of man children, and second of all the one who was punched in the face is really objectively very annoying, so he probably mouthed off to someone who’s much bigger than him and got hit in the face.”

At this point I’m just trying to leave because I was pretty drunk—there had been an open bar—and I’m like, “I just cannot be talking to this jackass CEO right now.” And he’s like still talking to me, and I was like, “Hey, I’m not trying to tell you how to run your business but you need to call the company attorney, like right now.” And he’s like, “No, no, I don’t think it’s a big deal. I don’t think we need an attorney.” And I’m like, “One of your employees just punched another employee in the face at a company-sponsored event. You need an attorney.” And he’s like, “No, no.” And I was like, “Oh my God, how can I make this clearer to you?” I said, “You need the other gay Jew. I am your product manager, the other gay Jew is your attorney. You need that gay Jew. I cannot help you with this situation. I don’t know why one of them punched another one in the face, but I do know that you need an attorney.” And, of course, the next day the attorney was like, “Thank you for having him call me.”

“I would also routinely wind up the only woman in a room of company leaders. This was a global company so we had 20 country directors at least 50%, maybe 60%, were women. But if we had a meeting of the country leaders, we would only fly men in.”

This situation was ironic because just a few hours before the Christmas party another product manager and I had gone to the CEO to the lack of professionalism with the engineers. He was like, “What do you mean?” And I was like, Well, in the past week, one of them stood up and yelled at another one for no apparent reason. Another decided that he’d had enough of a meeting that we were in, so he slammed the table and announced that he was “done talking about this.” And what he was done talking about was literally his team’s plan to finish a project, so he stormed out. We had another male engineer—I should stop saying male engineers, actually, they were all men—throw something in a meeting because he also didn’t feel like he should keep answering questions. And the questions were always about work, like, “When will this be done?”, or, “Can you help us understand why this project is four weeks late because we have outside partners who are waiting.”

So anyway, the day of the holiday party I went to the CEO to talk about the lack of professionalism, and several hours later one of the engineers punched another one in the face. Way to underscore my point.

God that was a long-winded story. I would also routinely wind up the only woman in a room of company leaders. This was a global company so we had 20 country directors at least 50%, maybe 60%, were women. But if we had a meeting of the country leaders, we would only fly men in.

What??

Right? So I started talking to the CEO about this, calling him out. The first time I walked into his office and said, “Hey, I think we need to talk. I just left a meeting of 15 people and I was the only woman in the room. And the only reasons I was there is that I happen to be based out of San Francisco, and the meeting was here, and I couldn’t help but notice that you didn’t fly any women in.” And he was like, “What do you mean?” And I was like, “More than 50% of the country directors are women. So when you were choosing who to fly in, why didn’t you choose to fly any of them in?” And he was like, “Oh, I hadn’t thought about that.” And I told him, point blank, “Listen, it’s pretty uncomfortable for me to say this, but I think you’re running like a boys’ club here. I don’t think this is conscious, but when you personally picture leadership, you seem to only be picturing men, and we need to think about what that means for our company.”

“There would be these meetings with say me, and the CEO, and say two other men. And I would just pitch an idea at CEO, and he’d say, ‘Well, that’s a terrible idea.’ And one of the other guys would repeat verbatim what I had maybe five minutes later (because we would have all agreed going into the meeting like that was the best plan), and the CEO would be say ‘That’s a great idea! Debra, why don’t you come up with ideas like this?'”

And at first he seemed pretty responsive to this, but nothing actually changed. I was good friends with the head of HR and we started to have unofficial conversations about this. Then then they became official conversations. And, oh my god, there would be these meetings with say me, and the CEO, and say two other men. And I would just pitch an idea at CEO, and he’d say, “Well, that’s a terrible idea.” And one of the other guys would repeat verbatim what I had maybe five minutes later (because we would have all agreed going into the meeting like that was the best plan), and the CEO would be say “That’s a great idea! Debra, why don’t you come up with ideas like this?”

The first time it happened everyone laughed because we all thought the CEO was kidding. And the CEO asks us why we’re laughing and one of the guys says, “Well, I mean this is Debra’s exact idea. She just said this five minutes ago.” And I was like, “Yeah, that’s my exact idea.” And the CEO was honestly confused. It was like he hadn’t been in the room at all. That was the first time I had encountered sexism that was like cartoonish in nature.

“It started to feel like a comical exercise in gender stereotyping, only it wasn’t actually funny.”

I was at that company for about a year and a half. It reached the point where the conversations with HR were no longer unofficial, and the CEO and I would get into it regularly. I would say things to him like, “Hey, your revenue projections are nonsensical. I can’t even imagine where you’re getting these numbers from, but based on our actual revenue patterns, we’re going to have layoffs.” And he would say, “Well, you’re just not being optimistic.” And I was say, “No, I’m just being realistic. We have a huge staff, so I think this is a problem.” Other times he would say that I wasn’t metric-driven, which was really bizarre to me since I was always trying to talk to him about revenue. Once after he told me that I wasn’t “metric driven” I said, “I don’t know ‘metric driven’ means what you think it means, but the metric that I want to discuss with you is revenue. Revenue is a fancy way to say the money we need to operate our company. Whenever I try to talk to you about revenue, you shoot down the conversation, but then you want to spend literally hours every day second guessing every minor decision I make because you’re worried that it will have only a .4% increase in conversions instead of .6%.”

This became a constant refrain with him. He would routinely say, “Well, you’re just not numbers driven,” or “Debra, you don’t have good ideas.” Because money clearly wasn’t an important metric . And it started to feel like a comical exercise in gender stereotyping, only it wasn’t actually funny.

I was going to leave, but then we got this new female president. I decided to stick around, and see if things improved. Things got really shitty, and literally I would get criticized for the tone of voice that I used in email. As if emails have a tone. During the last two months the president started telling me—I am not making this up—that I needed to smile more during the day. But the reason I stopped smiling was that it was just not fun to come into work. My guys—my team—actually noticed and asked if I was mad at them. And I was like, “What do you mean?” And they were like, “You used to joke around with us every morning and now you don’t joke around at all. You just put your headphones on and you work.” And I was like, “No, no, I’m not mad at you guys. I have things going on in life.” I was amazed that they’d noticed because, like lots of straight men who work in engineering, they were just completely oblivious to what was going on around them.

Oh, and the one performance review I had read like that that article that was going on around on Facebook that highlighted the phrases and that are only used in women’s performance reviews. Like “abrasive.” I was “abrasive.” We did 360 reviews and this feedback came from from male colleagues who hadn’t been pulling their weight at all until I was on staff. I would say to them things like, “Hey, we pay you six figures and in return for that we expect you to do the work that you’re assigned during the day in a reasonable timeframe.”

I’m trying to think of funny stories for you, but none of this was funny. My life was a parody of stereotypical sexist behavior.

Man, you worked at a comical extreme it sounds like.

The amazing thing about this is I had just left this automotive tech company, which was just not like that at all. It was professional, it was fine and sometimes I was the only woman in a room, but only because it’s tends to be men who are jazzed at the thought of working at an automotive tech company. The company where I had the most negative experience was a social enterprise where people really prided themselves on how aware they were of systemic racism and sexism and things like that. Irony alert.

Major.

Do you want to know how that ended? This is the only good part about this entire situation. There was this project that the CEO was really stoked on even though it was a really stupid idea. It was a clusterfuck of a project but my team took it on because we’d been working on something else forever and needed a change. I spoke to the heads of every major division in the company and we figured out literally the only path forward. I got buy off from everyone before talking to the CEO. Then someone’s assistant scheduled like seven hours of meetings, and I was like, “We don’t need seven hours of meetings, but whatever.”

We start the very first meeting, there was a room full of people, and I said to the CEO “Hey listen, everyone in the company has agreed there’s only one path forward, so all we really need right now from you, CEO, is for you to sign off on this path forward so everyone can get started.” And he spends the next seven hours laying into me as a person. How it’s clear I “haven’t really thought about the project” and “I’m not taking it seriously”. After a few hours I pulled the other product managers into the meetings as well because I needed backup. Both of them repeatedly told the CEO that we all agreed that there was only one path forward. So the CEO starts saying how it’s clear (somehow) that I’m “not thinking about the metrics and blah, blah, blah.”

So seven hours later, it’s time to leave for the day, and someone has scheduled some dinner that I’m supposed to go to. But I’m in tears, which has never happened to be before at work (don’t worry, no one saw). And I called a friend from New York. This guy has known me for two decades, and assumes someone has died because I’m crying. And I tell him, ”I’m crying because I have feelings. And I’m not used to having feelings. And I don’t know what to do about this.” My friend tells me, ”Go home, get a pint of ice cream, and watch Scandal or something.” And I’m telling him I can’t just go home because there’s some fucking dinner I have to attend. And he was like, ”Okay. You know how to handle this. Do not talk during the dinner. Just sit at the edge of the table and drink your wine and don’t talk to anyone.” And I was like, ”Okay. Got it. Just drink quietly.”

“So finally I say, ‘You wanna know what’s going on?’ And I held up my fork and said, ‘I would rather stab out my own eyes with this motherfucking fork than talk about our goddamn job or our goddamn misogynistic prick of a CEO.'”

So I get there and no one’s there, and I start drinking. Everyone else was a full 30 minutes late. And then we sit down and I’m like at the very end of the table, and someone’s like, “Hey, Debra, come sit at the head of the table.” Because normally I’m the funny one. And I’m like, ”Oh, fuck.” But I tell myself, ”Just keep drinking. Just keep drinking. You have this plan.” And everyone keeps trying to engage me in conversations, but I’m not willing to talk. And none of these people have ever seen me not say a word for 90 minutes, so it’s starting to get weird that I’m not talking.

Someone, I can’t remember who, just wouldn’t let it go and kept trying to engage me in conversation. And at this point I had probably a bottle of wine on my own, and I was like, “I just don’t really want to talk right now.” And someone’s like, “No, for real. You’ve never been quiet this long. What’s going on? Blah blah blah.” And they just kept trying to talk to me about work and about the meetings we’d just had and whatnot. So finally I say, “You wanna know what’s going on?” And I held up my fork and said, “I would rather stab out my own eyes with this motherfucking fork than talk about our goddamn job or our goddamn misogynistic prick of a CEO.”

And then I went back to eating my food while everyone else sat there stunned and quiet. I ate my food, finished my bottle of wine, went home, the next day took a sick day, and the next day was told to come into work at 8AM (which is two hours before I get to work) to be fired. And so ended my illustrious career working for someone else. Misogynistic prick in question did not fire me himself, he had a woman do it. And while she was firing me, she was said, “I am really sorry about his behavior the other day.” Because she had been there in the all-day meetings.

I still think that the fork incident was my finest professional moment. I can see how calling calling someone a misogynistic prick would be a problem, if it wasn’t objectively true. But in my defense, he was a misogynistic prick. This was just a statement of fact.

As an aside, the guy who punched the other guy in the face—not fired. The guy who’s throwing things in meetings—not fired. The guy who posted a bunch of swastikas on Facebook publicly while identifying the company he worked for—not fired. None of these people were fired. Me—a bottle of wine in, state objective truth about our boss—fired. So, I don’t know. I still think it was a good way to go out.

How do you feel about the state of tech in 2016? What excites you and what frustrates you?

I’ve never been interested in technology for technology’s sake. I’m not like, “Look at this awesome app that I downloaded that lets me throw angry birds at something.” I’ve always been interested in technology as a way to solve other problems. In 2004 when I first started wading into this political work it my question was, “How can we use the internet to organize volunteers?” Now, I look at the internet as a whole and think, “this is the most powerful and least expensive information distribution system we have ever seen.” The internet is the single most important advancement in human communication and information distribution since the printing press. Only it’s cheap It’s accessible for everyone. You could host a website for seven bucks a month at DreamHost and the whole world can see it.

“I’ve never been interested in technology for technology’s sake. I’ve always been interested in technology as a way to solve other problems.”

For me it’s not that we’re going to solve the issues plaguing American democracy with technology, it’s that we can use technology to amplify the solutions we’ve already identified. I’ve focused on education—how can we educate all Americans about voting without spending a bajillion dollars? We can use the internet. Every day I see so many examples of people using technology in creative ways to solve problems that are much bigger than “how am I going to get my laundry done” or “where can I find a taxi.” I love what we can do with technology, but I don’t necessarily love technology itself. I will use the most boring, established, non-sparkly technology to solve really big problems.

“For me it’s not that we’re going to solve the issues plaguing American democracy with technology, it’s that we can use technology to amplify the solutions we’ve already identified. I’ve focused on education—how can we educate all Americans about voting without spending a bajillion dollars? We can use the internet.”

In terms of culture there interesting things afoot in the tech world and in the valley. The younger women entering the field now have mentors that women my age didn’t necessarily have. And these mentors have had enough of this weird, sexist bullshit. There are a number of women in tech groups, and lesbians in tech, and a consistent topic of conversation is how do we protect these younger women? How can we make sure that sexism doesn’t thrive in the valley? And what do you do when your team is off the wall bonkers and out of control? A lot of us also think about how lack of diversity affects not just the companies, but the world. Who has access to technology and therefore who has access to information. There is so much thoughtful conversation going on around access issues.

I’ve personally come to believe that your user base will resemble your staff. If you have a staff that is 90% white men, you might wind up with user base that is 90% white men because your team will build a product that meets the needs of the people they know. You have these companies that are hegemonist and therefore the solutions they come out with are pretty defined and not very creative. In my field the way that plays out is through the techniques we use to reach underrepresented voters. We’re talking about low income voters, voters of color, young voters, urban voters. Basically people who aren’t straight white men. Traditional voter outreach tactics don’t seem to reach these groups, likely because elections and campaigns are generally run by straight white men. So these men run campaigns that speak to other straight white men, and a significant percentage of potential voters are left out of the fold. If we want to have an electorate that isn’t just straight white men, and we want to have candidates that aren’t just straight white men, we need to bring people who aren’t straight white men into the fold. I want to reach the people who are not being reached, and therefore I will not build a team of all straight white men, even if I live in San Francisco. If we all look the same, we’re going to reach the people who are already being reached.

“I’ve personally come to believe that your user base will resemble your staff. If you have a staff that is 90% white men, you might wind up with user base that is 90% white men because your team will build a product that meets the needs of the people they know.”

I think that’s true for every tech company. And just see right now in 2016, there is some sort of shift going on, and people are calling out the lack of diversity, they’re calling out the VCs, they’re calling out the CEOs.

Yeah, it could be why we’ve hit a wall with a lot of these unicorns, of like—you had all the potential to globalize, but at some point you hit a wall.

Yeah, you somehow were unable to reach people who didn’t look exactly like you. And it turns out there’s only so many users who look exactly like your team.

Oh, i just read a quote the other day on Facebook that was great. “When the lights come on, a unicorn is just a horse in a party hat with a fake horn.”

These unicorns, when you remove the VC funding, they’re often just failed companies.