Prioritizing Happiness with Andrea Breanna

Becky Mollenkamp:

Thank you for being here. And as always, let’s start by hearing about your relationship with feminism or the word feminist. What does it mean to you?

Andrea:

Well, you know, as a transfeminine person, that word means a lot to me. You know, also I grew up in a house with four sisters. So, and a Mexican mom, where it was in many ways matriarchal in a way I know we’re all proud of, including my dad. Um, not completely. There’s a lot of patriarchal things, you know, oh my God, there’s, they come from a more traditional background, but there was always this sense of progress, and progress and feminism being completely in my mind since I can remember being linked together, that is progress. And you know, it’s so tied to the word feminine, which has when I was little, like I knew about my femininity and when I expressed it, even in a posture in the slightest way, the way society would attack. And I learned that I had to hide that part. And then you see everything around. I mean, I just cannot be a bigger fan of Barbie, the movie. I can’t stop. I scooped my daughter and I watched it together when we were in Berlin, is when it released. And like we both were crying for the whole, for days after, it just is so good. And so, you know, I know that it’s charged in society, but I think it’s a type of charge that’s necessary and right. And so it has always meant a great deal to me.

Becky Mollenkamp:

Yeah, and I agree that it being charged, there’s the charge where it’s the people that I am not concerned about. But even within the what because my feminism is intersectional, right? If it doesn’t look at all of the ways that oppression affects everyone, right, and all of our various identities and all of these things, then I don’t see it as being feminism. And there are many women of color who have felt excluded from feminism. And have historically been excluded in many ways. It’s been a white feminist vision often that is sort of associated with that word, which is why I like to ask because for some people it feels very powerful and other people like the word womanist and some people just don’t like any of these words. So I think it’s always interesting to hear.

Andrea:

Obviously with the intersectional feminists and as a trans person, that means a great deal to me. You know, you wouldn’t be inviting me here if you weren’t. And it is, you know, for me though, I have to say that I see the like trans exclusionary, the TERFs, I don’t even, I don’t think that is feminism. I don’t think feminism can be racist and transphobic and still be feminist. It’s just racist and transphobic and etc..So obviously white women are an enormous problem in the world, and certainly Barbie doesn’t do much to address that.

Becky Mollenkamp:

I’m not here to have you speak specifically around trans issues. That’s not why I have you here, but you did bring up the fact that you are trans. And I am, the one thing I’m curious about is because I believe if I’m not mistaken, that you came out publicly quite a bit later in life compared to you know, it wasn’t very young. You’ve always known, but the fact that you brought it out publicly and how that effect, I’m curious about the effect of that on your professional experience.

Andrea:

That first year and the first week and days and hours and months of coming out. Whoa, I mean, it was so terrifying. I had stayed, I mean, I know you’re asking about what happened after, but for me to explain why my experience was like it was is that some people are trans, but they find that out about themselves later in life. So they hadn’t been spending all their life thinking about this. They kind of come to realize, and it connects dots to things in their past, but they haven’t been consciously thinking about it. And that’s completely valid also. It’s not, I’m not in any way criticizing their experience in any way. But for me, I knew since I was little. And so though I was so terrified of coming out and I was braced for the worst, because I knew who I was, and also not only did I knew who I was, I thought there was this tiny little membrane of protection that I had in the closet that I was in and that everyone actually knew. It was weird for me, all the people were like, I had no idea. I was like, oh my God, I was like sweating it so many times of like feeling like it’s obvious or, so for me, because I was always hyper aware of it, in my career coming out was actually really, in the end, really wonderful and net positive. There were some smaller ugly moments that I tried, I don’t wanna focus on because they weren’t big significant ugly moments, they were small ugly moments, and the big significant things were all actually really positive and beautiful. But I do think that’s because for the first 25 years of my career, if I detected any homophobia, transphobia, anything like that, I did not want to work with you at all. So the people — my investors, my team members — all these people that I thought I’d potentially just literally lose the moment they found out, actually it was so awesome. It was really wonderful. They were very supportive and they did, I had to learn to be patient because there would be stumbles if you said my — you know, it’s hard to switch names on someone and it’s very hurtful as a trans person, it’s called a dead name. So it’s like, oh, you still see me as that. But I had to be a little patient with people where it’s, there’s a difference from I’m doing it intentionally and I’m, you know, adjusting. And so if I had, if I had that patience and that worked and it was all really wonderful and pretty quickly it was all very positive. I did find that there were some really beautiful Brené Brown type things that I never would have anticipated that were just so much more beautiful than I could have imagined. And that had to, it definitely had a huge impact, the power of being vulnerable. You know, you have founders joining and I think one thing we all share is like, you start something, not to be a scary CEO that people are nervous around, you know, that’s no one’s goal, especially everyone you’re gonna have on here. It’s like you had a vision and you didn’t wanna be victim to some asshole boss your whole life and you wanted some freedom to be able to live your life the right way and da da. What happens to you is that you end up with the CEO title and as much as you may be, like for me I love building teams. I love that like I’m for me, I’m always trying to teach my kids like it’s not competition it’s collaboration. I love team sports, but I don’t really care who wins. I care much more about all those amazing dynamics that you learn about people in the game. I always love that. So, but when you’re CEO, you do have the power and responsibility to hire and fire people. And so I found that the vulnerability, in particular, of being openly trans ended up being a wonderful way for it to all just be so obviously less scary, you know, to them in every way. And to be able to be supportive and for me to be able to be vulnerable and crying in all-hands, you know, not like breaking down crying. And there’s where you realize the aspects of being feminine in the corporate world where It’s been fascinating for me just observing and understanding and having been doing that since before and in the closet, and then out of the closet is a different experience for sure. And I do think that there’s a pressure on all women to have it together, right? To be buttoned up. And on top of that, for trans people, I think for, let’s forget my investors and my team members, my clients who were paying the company, I think it would be very scary for them to work with any person that they worried was emotionally super fragile that could end up having breakdowns. There’s a lot of these things. There’s the narrative about trans people is that we’re all borderline suicide, right? And that’s what gets told over and over and over because there’s so much transphobia. We’re at the front lines of this awful moment that used to be gay men in the ‘50s and then gay women, but now it’s like trans people are at that forefront. So literally, we lose lives every day, month. There’s not, it’s awful. And we lose for very valid reasons of the depression of being alone and being ousted and all of these things. But when you come back to the work environment and you’re a CEO or you’re trying to work in a business environment, that narrative is very dangerous to success because that’s why people are so scared to talk about mental health in the workplace, right? Because I can tell you, it was fascinating also, the truth is that we have clients across the political spectrum. We’re a technology platform and they can use us as a platform. And so we have some clients that are, we have a lot of them, the most of them are super progressive and liberal. And then some of them are kind of conservative. So I was braced that that’s the end there, even though they knew that we were like always more women, more international, really gay friendly, like you got to do a deal with a gay salesperson and head of sales. And so they had to be okay with it to some degree, but I was braced for it, like to get a little ugly on that side. The funny thing has been that actually, like all of them were incredibly respectful and really kind and supportive and nice. It was surprising to me. And then we had like actually the CEO of one of our most liberal companies was the one who had the most shockingly offensive reaction to me. So it’s like, you know, you realize that there’s this like, you know, especially as a trans person that it’s a little more complicated. But I think the point back to like being feminine and a founder is that there is this game that you have to play, where you have to find in your life a lot of places where you can be absolutely real and not posture in any kind of way at all and not worry about being composed or having it together, but have really truly safe spaces. And ideally those safe spaces are in work too, not just, oh, I have a great girlfriend or I have my wife to go to, or I have a friend or whatever it is. Literally within work environments to have a feeling of safety is actually I’ve been learning surprisingly rare.

Becky Mollenkamp:

I wanna switch to talking about Rebel Mouse, which you said you started in 2012, and you, at the beginning of that, were going down that traditional sort of VC path, raising a lot of money. I think you said in my research, I think I saw $23 million, and it was … from what I understand, it sort of came easily and then also was spent real easily that you burned through that. I think what I read you said was burned at $800K a month ‘at the peak of stupidity.’ I wanna make sure I’m saying you said that, not me. And when the money was almost gone, you moved to a sustainable model. So instead of going after more of this traditional VC sort of funding route, which you could have done again. Instead, you switched to a sustainable model. So tell me, I’m really interested to hear about that, what that looks like, how it’s different, and also what motivated that choice.

Andrea:

It all is tied together in this moment. To be clear, Becky, I don’t think I could have raised another round. Because at that point in the company, now it’s not about what you did in your past and what’s possible, it’s numbers, where you are now. So after I had raised $23 million, and to be fair, I had raised $21 million. And then I had a deal that was close to getting paperwork. We had done through proof of concept and everything and Comcast was gonna give $25 million on evaluation of $100 and the nightmare was going to continue. But I was living in a nightmare career wise. Thank God I had my family and the kids. I feel very lucky in that, but career wise. That phase where I had raised $21 million, I’d raised first in smaller rounds, but the last thing had been $15 million. Oh my God, the pressure that came with that. What came also with that was a lot of … things what happens is you wanna hit these huge goals so badly and you get such a thrill of having these powerful people validate you as one of these elite people that can create a billion dollar plus company. And it’s a drug and it’s very addictive and you really just want to keep tapping into it. So, you’re right, I have the phrase ‘at the height of stupidity’ that I use for this era. At the height of stupidity, I had a culture full of toxic people because whether you were a cultural match and whether you were kind to other people wasn’t the criteria on whether you were hired or fired. It was all about hitting these goals. And so I would spend most of my time going and apologizing. I know she’s sort of a sociopath. I’m so sorry she said that to you. She didn’t mean it. She’s just really hitting our numbers and she’s killing it. She’s just trying to get this deal done. But you’d have salespeople selling whatever to get their commission, just completely unethical. And you’d have engineering managers throwing around horrible language and just, it was a terrible culture. And I would talk about the culture that I thought I had and at the height of stupidity was starting to fully realized like, I don’t have that culture. I have the nightmare culture instead. And the Comcast deal fell apart. Our latest quarter … you have to keep it exciting, and our quarter was gonna come in too low and there was a criticism on the proof of concept. I woke up every day for three years of my life with an impending sense of doom. It clutches your stomach and it was there all day long and it lasted through the weekends and through vacations. I was, and then I will never forget we did, I used to do a lot of these in this phase, there were a lot of like these fancy dinners that are corporate type of, so it’s like Linda Boff at GE was having a dinner and it was all CEOs and I love Linda by the way, maybe as she, maybe you can have her on, she’s amazing, but I met Phil, I had met Philip from Refinery29, he was CEO then um, a few times I always liked him, he was super sweetheart, lovely person. And he was like, I, you know, I was like, how are you? He was like, well, right now I’m good cause I just saw my CEO coach. I was like, oh my God, you have one of those? And it was Katia Verresen who he introduced me to who is my resource. When you ask me like read Katia Verresen’s posts, try to get her time. She’s so amazing. And, um, in that moment. where we knew the second round wasn’t coming. We were burning all this money. The money was almost gonna be over. Then there was this moment where the current VCs are used to this moment. Most of their ventures end up there. And then we had a talk and I had to look in my heart and it would be an easy place to abandon ship. and say, let’s send the shutdown notice to clients. Let’s close the business down. And I go figure out what’s next in my life. But I really like what we do. I like what we’re building at Rebel Mouse. It’s not sometimes as a founder, over the years you get challenged. And sometimes you realize you were working on something that’s not truly you. It was an idea that sounded great and shiny, but as you get in the reality, then you should just get out of it. But for me, that wasn’t the case. I actually liked it. I had a product that was generating revenue that I love the building stuff for editors and publishers and high traffic. And we had something very real. So Katia was the one who, we had all these sessions, it took about a year of meeting with her at least once a month for me to get to that epiphany moment. But it happened where she shared that on the flight over, she had watched the Warren Buffett documentary and that he was asked in it something and he said, every key business decision that he ever made in his career, every single one, was based on his own personal happiness. And the moment she told me that, it was like this, duh, it’s so obvious. It was like, that’s me, that’s what I’m meant to be doing here. I’m supposed to follow my happiness. That’s the right path.

Becky Mollenkamp:

You say that’s obvious. And yet, I mean, I it’s interesting timing because I was just talking to one of my clients, a founder yesterday around changes that she’s needing to make in her company to reflect economic realities. And she said, I want to do this thing, right? Like there’s all of this talk around what she wants to do, what she feels like she needs to do. And yet, and those things are things like, I wanna prioritize my own needs. And she’s like, I wanna do these things because I know that that’s what’s gonna make me feel better. And yet. There’s this constant guilt, this voice of, well, but I have obligations to these people or I said I would do these things, my clients think of it this way. You know, in your case, the funders are expecting these things, right? We say it’s easy to say, my happiness should be my number one KPI. And yet that voice in our heads often says, we’re not allowed to do that. So did you wrestle with that piece or was it for you like, no, that makes so much sense that this is an easy switch to make.

Andrea:

None of it was easy. It’s hard. It’s really hard to follow happiness. The more I think about it, it’s like it’s about the pursuit of happiness. Even if you make happiness your number one cultural KPI, the number one thing we should do is be happy. You don’t want to have a, and now everyone has to show up smiling like, ah, that’s a nightmare. Give me a break. I have to be able to be sad or bummed out or low energy or whatever. So, but also, the grind, the hustle, everything about particularly American culture and in particular tech and startup culture, this is not about your happiness. This is not about the pursuit of happiness. It’s the pursuit of power and wealth and it comes at the cost of happiness. It doesn’t produce happiness. No one’s like, oh, Instagram made me so happy today. Like no one has ever said that. Oh, I was on X or Twitter and it made me happy. No, like technology has failed in general to make us happy and working in tech has in general made us miserable, stressed out, anxious, you know, and we’re producing basically that in what we make out of Silicon Valley produces basically all that ball of anxiety, that’s like the product that’s being delivered. So I think you have to become very aware that you’re fighting against a current moment and current cultural context, but for something that’s fundamentally right and will win over time and was in our Constitution for a reason, the fucking pursuit of happiness. should come first, but you have to fight for it. And I was very, you know, I came out at the same time that I changed the structure of the company because it was all aligned. It was all like, you know what? This is it, I’m done. Like I’ve always been an honest person, yet my own kids and wife don’t fully know who I am. And so enough of fear, fear of investors, fear of. clients, fear of employees, fear of being gossiped about, fear of being criticized. All of that was plaguing my life. And I was in a moment where for the corporate world, it was actually like restructuring and getting rid of everybody toxic that was also very expensive salaries was like what the company needed at that moment. So if we were growing like crazy and we had just raised another $25 million, then like I said, my nightmare would have continued. Even though that would have been apparent success, it would have just plunged me further into the nightmare because there’s no way I would have been getting rid of people who were hitting successful goals. If they were toxic, it wouldn’t matter. And that’s what Silicon Valley does  basically.

Becky Mollenkamp:

Right. You’re not in Silicon Valley, right? You’re in New York, if I’m not mistaken.

Andrea:

Yes, I grew up so much in between Mexico City and Palo Alto, and I worked from New York for Huffington Post. A huge part of my work was visiting Facebook and Twitter and LinkedIn all the time. So I can’t stand going to the Valley. I could never live there. But I think we, you know, if you work in technology, the impact the Valley has on technology, it’s just better.

Becky Mollenkamp:

I’m sure I just wonder if that is a purposeful decision because of some of the things you’re saying like I know that you can’t escape it, the attitude, you know escape that experience entirely, but I wonder if being at least removed from the actual physical location helps.

Andrea:

Oh, it helps a lot. Honestly, I can’t, when I go to visit or a business meeting, which is now very infrequently, because part of happiness for me is like, come on, let’s just meet on Zoom, let’s talk, we can screen share, don’t make me get on a fucking airplane. So I don’t do business travel anymore, really. And it’s been one of the greatest things in my life, but. before visiting the Bay Area, it’s like I’d break out in hives. It drives me crazy to be there. You can’t get a coffee without, ah, you hear what they’re saying in line. They’re like, oh God. So for me, it’s very frustrating because as a trans kid, I believed the Internet and technology was progress. Back to feminism, like what’s a true thing that should be happening. I believe feminism can still go the right direction. But technology right now, I mean, it’s just I can’t, couldn’t be more disappointed in how soulless, how much it’s just been what I’m describing as having lived in myself. I know why they’re going through it. They get addicted to the drug of all the approval and all the wealth and all the power and doing what’s right or what’s good, just gets lost completely along the way.

Becky Mollenkamp:

How do you balance your value system, the happiness, and these feelings around tech becoming a bit of a drug and the power dynamics and all that? How do you balance that with like working in tech and creating tech product? How do you bring a different attitude to your actual product?

Andrea:

I’m very proud that we’re building it in the way. I don’t think that five guys and a whiteboard is the right way to build technology. So it’s not like, it’s like, for example, abandoning feminism because of the TERFs for me would be wrong. And abandoning technology because of the Elon Musks of the world would be equally wrong. So I think it’s an obligation. The center of power will change. It’s not always gonna be, and literally that stereotype of five guys is five straight, mostly white guys. And in a room together, no remote, no international, anything like that. So we’re really dedicated, for me, I talk about it a lot. It’s not just what we’re building, it’s how we’re building it. And so the fact that we’re, I think, 70% women on the team, within leadership it’s 70%, we’re completely international. There’s 100 of us in 34 countries. We have a culture of real empathy and kindness and flexibility. We do have an obligation that you have, you have to have standards. You have to have really clear roles and responsibilities so that people can know they’re successful and then have that flexibility and know they’re working with people who are also really good at their job. And so not everyone makes it through their trials at Rebel Mouse, but if you do, it’s because you have that combination of being really good at your skill, and being really wonderful and kind and craving that, which is very easy for us to recruit on because there’s so many people in the world right now that are so sick of being treated like this by tech companies. In every all-hands, I tell everyone, the company is not more important than your life. There’s no way, your life comes first. So you have to make sure that you tell us if, wait, that messes up, I can’t pick up my kid if we do the meeting then. You know, or I don’t, or I can’t make my yoga or my Pilates or Zumba or whatever it is that makes you happy. You have to build that into your everyday, and you have to feel comfortable saying, I’m sorry, that meeting’s too late or too early or at the wrong time. Normally that’s a luxury that only the powerful are afforded. Right. So as CEO, I can say, oh, sorry, that doesn’t work for me. But if you’re, you know, an account manager who just joined, do you feel comfortable saying that? Or do you just quietly like not pick up your kid anymore?

Becky Mollenkamp:

And I assume in most of Silicon Valley or the traditional tech space, and by the way, not just tech and so many industries, but I know in tech it can be worse. That isn’t something people feel comfortable doing because they have seen that they aren’t, they really can’t. There are direct ramifications for that sort of thing. Going back then to about six years ago, I suppose, when you decided to take that risk in all the ways and looking specifically around the company, but all of the things are part of that of saying, my happiness needs to be the number one KPI. And then, I think, trickling from that is happiness in general, the happiness of my team also, right, not just you also needs to be that number one KPI. And you know, with any sort of KPI, we have to be able to measure those things, right? There need to be metrics to see is this working, are the things we’re doing working? What are the kinds of things that you have played with in that time and where are you at now as far as how do you even begin to measure something that isn’t as easy to measure as dollars and cents?

Andrea:

Listen, some things I think you have to accept at the beginning that it’s just a North Star and it’s worth it. Not everything needs to be measured in life, some things you just trust your gut and go that direction because you just know it. But over time, and that’s if someone had told me, yeah, you can do this, but I need you to outline the KPIs that you’ll use to measure it before you do it, I never would have done it, I would have been stuck. Now, when I look at it, there’s some very simple KPIs in the end. One is, as a company, what’s your churn rate on employees, not that you terminated the relationship and let them go because it didn’t work out, but that you wanted to keep them and they left anyway? And when you actually have, like we’re at a 1% rate at Rebel Mouse for the last two years on that. So that is like, you can measure that. And then that comes with a lower churn rate on clients also, which our churn rate is also really awesome there and has gotten way better because we’re aligned. So you can take core business measures. How much money were we losing? How much were we growing revenue? Your core business KPIs actually will be positively affected by a positive, happy culture. I believe that. But you often arrive to these thoughts because you know there’s a problem. So you have to address it, and there’s going to be this dip and this hard time and this da da da where you kind of regain that. And then I think those things actually can be measured and then you have to make sure that you don’t put growth as the number one KPI and that’s what capitalism and tech and investors really want all of us to have the number one KPI to be growth. But you know, growth can be the number one enemy to happiness. It’s just like, it creates a lot of stress and it creates a lot of problems. So I’ve enjoyed talking to anyone who goes through the like, I went through a company that grew like crazy. like what was it like when Huffington Post grew that way, or what was Rebel Mouse like when it grew from those? Now I’m very proud that we’re growing in a much more sustainable pace, because it’s crazy when you’re growing 100, 200% a year. It’s just, it can be very fun, but a lot of people get hurt in that ride. And the way I get to run a company now, not a lot of people, it’s a way lower pain rate.

Becky Mollenkamp:

Yeah and you’re still in the tech industry and I, you’re making all of these changes and probably trying to surround yourself with folks who are also interested in, and looking at tech in a new way and looking at business in a new way, and still you’re in this world where it is about growth and money and power and all of those things. How do you, do you still have those creeping thoughts because it’s not like we can just suddenly say I’m done with capitalism and I’m, you know, I’ll never let these slots affect me. Does it still ever start to bother you or like creep in?

Andrea:

I like to believe that we’re working on the combination dream of a company that has the potential to be a billion dollar plus company and, but that we’re doing it in our own way. And so where, you know, founders like to think that five years later, you did it, you built Instagram and you got paid $3 billion by Facebook or you’re now going public for $20 billion. It takes a lot longer than you could ever imagine. So the way I’m doing it, probably like, if we have that type of outcome, it’s five or 10 years away. But the team that is doing this with me, we share that mixture of knowing everyone who works for me has had a chance to work for another tech company at least once, if not many times. So they have tremendous gratitude as I do that we’re not doing it that way. So it’s, in the end, in terms of like talent, like with my chief creative officer or my chief technology officer, they could leave. Tech is in a slump now, but they could find jobs. But will their boss be an asshole? Will the culture be toxic? Will they ask them to work their fucking asses off? Will they make them travel inconveniently? Will they make them… All of those things, they’re like, never mind, maybe I’d have more money or more growth there, but my life would suck in comparison. So quality of life actually matters to smart people a lot, and you can keep really smart people through that. So the other, you know, the other thing, and then that balance where we do believe that we’re doing this not in a rushed way, not in a panic, not with urgency, and not that we threw out the best parts of our life in exchange for it, but that we’re working on something that has the potential to be really big. And so that is the lucky balance we have right now. And it might just be fiction, maybe 10 years from now we have the same company doing, you know, the $10 to $20 million in revenue a year, and it never became bigger than that. I won’t be like, oh, what a depressing, horrible thing, because we will have spent those 10 years living life really wonderfully and happily and supporting each other and all these things. I do have the hope that the senior leaders and the team members around me in the next five or 10 years, something happens that lets them have a big cash moment in their life. And so that’s why we all accept these horrible working conditions, right, is because there was that moment where AOL bought HuffPost and all that work I had done for all those years was suddenly turned into this thing where we could buy a place. And so I hope that we can still do that, but I don’t want that to come at the cost of having lived the miserable life.

Becky Mollenkamp:

Talking about the miserable life that you were in and where you’re at now and the shifts that had to happen. Obviously there was personal things, like you said coming out, but around the company, one of the changes I know you made was going from a physical space to an entirely remote force. I’m curious about that change and why that was part of happiness for you and how that is an advantage for you now.

Andrea:

My team at Huffington Post was always two-thirds minimum. All my teams before Huffington Post, everywhere I worked, I always loved building an international team. Um, for me, technology wants you to pull an all-nighter every night, and that’s not healthy. But actually, if you follow the sun, you can pass work off to Europe, to India, to Asia, to West coast, to East coast, and you can do this thing. So I’ve been doing that for 30 years. I love that. I’m predisposed to it. My mom being Mexican, but growing up a lot in the Valley. My dad’s side of the family lived close physically, but was not close at all. I didn’t feel like they knew who I was at all. And my mom’s side of the family, far away in Mexico, knew everything. My grandmother knew the night I lost my virginity, I’m sure. She’s like, it was, sorry for the TMI, but like it was very close and they were far away. So I’ve always believed in that. And though I don’t use Spanish in my career, understanding cultures and how they’re different has been a huge part of my career. So at Rebel Mouse, I had caved to the investor and client pressure to have an office and we had an office in the same building as HuffPost. It was a beautiful office in SoHo, and I hated it because I hate all offices. I don’t like offices. I don’t like to go to them. When we do deals with clients, now we don’t say it out loud anymore because it’s all just implicit, but we used to say we don’t have an office and you probably won’t see us in your office either. But let’s jump on screen share. Let’s jump on Video. We like to get stuff done. We’re not gonna waste time traveling, let’s just go get stuff done. So for me, the office was one of the things that made me so unhappy because especially as CEO, and if people are there way before you get to the office and they leave after you left the office, they’re like, what’s going on in this company? Even though I might’ve been working till 2 or 3 a.m. and I might’ve been up at 6 a.m. but like my presence in the office was only from 10 to 3, then oh, I hated the office with such a pressure and such a trap and such a nightmare. I know that, the other thing also from us is there were a lot of people in the company that were in the phase of their life where they really loved going to a company because they’re young, out of college, like, what do I want to do? Stay in my fucking room, because that’s my bed is here, my laptop’s on my bed, like, I need to get out and go social interact and stuff. So they were there, not for the company and the mission, but because there were a lot of other fun, young, attractive people in that office that they could go to lunch with and have a social life and go to karaoke and all those things. I think America and society has to solve those problems, but it wasn’t like for my company to be a social gathering for people. It just was a nightmare for me, the pressure to be there. I was never that type before being CEO. Like, at HuffPost everyone knew I worked like fucking crazy. But you wouldn’t see me in the office all that many hours. I’d come in for the meetings, I’d come in for some times of it, but there was never any doubt and I did that in all my jobs. But as CEO, the only way to do that was to close the office. And it saved us a lot of money too.

Becky Mollenkamp:

And allowed you to even probably even more have a diverse, a internationally diverse workforce right, I think you now have employees in like 30 countries or something. And I hear the practical piece of that of allowing you to maximize the hours of day. But what about the culture piece of that? How does having this more international workforce reinforce your vision of a more diverse workforce?

Andrea:

After some success in my early 20s in New York and in the West Coast in my career, I went to Mexico because I’ve always loved being Mexican. I love the culture. And I thought with all those accomplishments, it should be pretty easy for me to find a pretty awesome job. And why don’t I go live in Mexico for 5 or 20 years because I love it there. And it was such a frustrating experience. There’s so few tech jobs in Mexico. So they’re given to the nephew, you know, it’s like very, and well, I get into a lot of tangents there on business life that I got used to. I like working on things, you know, when you love what you work on, it can be fun. And so that’s what I love to do. And, but then I tried from Mexico, I was living in Oaxaca and I tried to apply to remote jobs and like, honestly, you could have gotten me for $25 bucks an hour then. It was a deal. Like I was going to kill it for you, and nobody would give me the opportunity. So I ended up moving back to New York. But since then, part of moving back to New York, white flag that I can’t go live in Oaxaca in Mexico and do interesting work, but I am gonna go find those people who are dying for those opportunities and I’m gonna be in New York because I’ll connect that economic potential to those jobs. And so I love that, giving opportunities to people. Also, you know, there’s more and more. In the beginning of my career, that was totally new. And then offshoring and outsourcing and all this became a culture. But the difference in how we do it is that normally when you think about it, you use the word remote, which immediately, if you pay attention to it is a red flag. Remote sounds like you’re about to lose connection and you’re on a raft in a river. Like remote doesn’t sound like someone who should be part of your leadership team or management meeting. That remote sounds like someone just perfect to do CSS or QA. This incredibly limited, trivial or defined but junior job. And no one, I also noticed in the US when they hire someone. And you meet this and their kid and they went to Brown and you know their parents or you know what their parents did in life. And though the job might be junior editor at HuffPost, you start as a manager constructing all these visions that you communicate with the kid. Yes, it starts as junior editor, but if you nail it, you can become dadada and then you can become blahblahblah, and then you can. and you give them a path because you want to help them in life. You like them, you’ve seen them in person, you think they have potential. And all of those instincts are completely dead to international workers. No one ever thinks that way with them. So that has been really a wonderful thing, a part of our culture is like, actually, like our chief creative officer in the company started off as a junior account manager. She lives in Serbia and she hates, she has a huge fear of flying. So she would never come visit any client or anything. And we, you know, in the first couple of weeks, she was just unusually smart, unusually talented. And that’s what most companies miss. Instead of giving her the opportunity and seeing that and suddenly like, whoa, giving her space to grow, they hired a junior account manager in a remote position type of a thing and that’s the limit of your potential. So for me, that’s been really fun with the team that it’s actually, it doesn’t mean you’re, if you’re in Brazil or Serbia or Japan, it doesn’t matter, you can rise to the very top of the company.

Becky Mollenkamp:

I think you mentioned earlier that something like 70% of your workforce is women, and then about 25% of your team is LGBTQ. If I’m not mistaken, something like that?

Andrea:

I think we’re up to 35% now, so I’m very happy with that, but yeah.

Becky Mollenkamp:

And so does the way you’re thinking about hiring and promoting, is that part of what is allowing you to create that more diverse workforce in all ways? Because the way I’m hearing in the past, I have a feeling, gave advantage to certain people, namely, probably white folks and male folks. And so does this other way, the way you’re thinking more expansively around hiring and promoting, is that part of that effort to have that more diverse team?

Andrea:

Yeah, I mean, it just naturally happens when you can put that first. And, uh, and so it’s just, there’s it’s we, I’m very happy. We’ve worked through a lot of unconscious bias. And then, so, you know, if you’re hiring manager doesn’t really believe in all of it, you’re screwed. You won’t get there. But so for example, our CTO. was from Ukraine. We helped them get out of Ukraine far before the conflict, though we’ve helped a lot of other team members in Ukraine get out since. But you know, you kind of like hire, when you’re doing it unconsciously, and that’s the way 99% of the world works, you hire people who look and feel and talk like you. Any of those sort of stereotypes that people just naturally carry over that that’s taken out of unconscious and it’s part of our culture to make sure, you know, people don’t feel that way. So it’s been a lot of work. It’s so wonderful.

Becky Mollenkamp:

I know you mentioned earlier that you’ve always been like, hey, if you’re somebody who’s racist, sexist, whatever, I don’t want to work with you. So that’s always been sort of part of your way of showing up. But was this consciousness piece because when you said when you went to the KPI of your own happiness six years ago and everything that happened at that time, what I heard you saying too is kind of, this is when I just said, I’m done doing things the way it’s supposed to be, and I’m gonna consciously make choices that are about what feel good to me. So was that a big shift at that point? Like, had you fallen into some of this trap around hiring prior to that, that really shifted when you made those changes?

Andrea:

Oh yeah, absolutely. And also to be honest, it’s a lot less about the hiring because, I think that actually I had a pretty good ratio on women then too, because you can, that one always mattered to me. The thing is that people who are going to be culturally toxic in your company, you don’t get to know that in the interview process. That’s something that people who are going to be toxic are almost always, It’s like a 90% rate that they’re going to hide that really well in the interview process. You don’t really find out about it sometimes until three to six months in, and sometimes it comes a year later. Sometimes it’s two weeks later. But the question is, so it’s I think it’s a lot less about who do you hire for us. I get what you’re getting to and we didn’t have. We had more straight white males than we have now for sure. But our ratio compared to tech was, there were a lot of powerful women in our company, and that was pretty good. But you know, there was one who was like, so sociopathically mean, she was so mean to everyone. And it’s like, no, it can’t all come at the cost of, and I let that go for so long. It’s really more, I think, maintaining your culture is more about like, I like gardening a lot and gardening metaphors, I think should be used in business management more. I think there is this sort of trimming and pruning and realizing, oh, this plant does not go well with the other plants. And then how to deal with that in a respectful way for everyone, because when a company lets go of someone, Mostly that’s done in, you know, in ways that are really traumatic. And I think that no matter what it is, but we try to be very conscious and very clear that this isn’t about we’re right and we’re smart and you’re wrong and you’re stupid and we’re too good for you and dadada, but just that, you know, we’re a weird company with a weird culture and weird things and it’s like it either is the right place for you or it’s not, but that doesn’t mean like we’re going to be a bad reference and you were a failure and you suck and dadada. Actually, I think a lot of toxic culture can just be prevented earlier by realizing when a job isn’t right because a lot of times people will stay in a job that’s wrong way beyond what’s good for them and certainly what’s way beyond what’s good for a company.

Becky Mollenkamp:

Yeah, and you mentioned doing trial period sort of thing to help with that, right?

Andrea:

Yeah, wherever possible, you do trial periods, you know, sometimes you have to accept that they’re leaving a full-time job to take a risk with you. So no matter what, it’s a big moment in their life. And I think you have to really respect that, that it’s not just about your company, it’s about their life. So then what’s so important is that process of pruning that it’s really respectful with self-introversion. You know, the process of talking to someone that this isn’t maybe the right place for you has to come with, but we might be so wrong. You might not be getting the right support that you need. You might have questions that weren’t answered. There’s things where you have to give them a chance to be honest where they were scared and say, no, that’s not fair. I have these things weren’t answered. I had this, dadada, and that you have a chance to make it right on your side. And then also to just give them the clarity. That’s another Brené Brown thing, but clarity is kindness. And it’s so true in business. It’s like clarity is really kindness. Like, please don’t make me spend a lot of time confused and anxious trying to figure out what you mean. And so being really clear can help so much.

Becky Mollenkamp:

The compliment sandwich that people do sometimes when they’re trying to fire or something only creates more confusion. Just say what the problem is and don’t try to make it like, oh, you’re great. You’re great.

Andrea:

Yeah, and give them a chance to address it if they want.

Becky Mollenkamp:

Speaking of toxicity, because a lot of what I read from you was around salespeople you hinted at it earlier, that in that period of time when you were really like, I’m just going after, I’m taking the funding in, it’s about growth, growth. Sales is obviously a big part of that and there ended up being a lot of culture mismatches, salespeople that are selling anything, salespeople who care only about the numbers and not about right-fit client-product, all of that. What has changed in how you feel now and how you approach sales so that you are maintaining that culture fit while also still concerned obviously about growth?

Andrea:

Well, to be totally honest, we never went back to the same types of salespeople with the same types of training as before. So, we kept Chris Anderson is our Chief Strategy Officer, but he’s really head of revenue, he could be CRO, and Chris saw all of that spectacle. And he hadn’t done a lot of like sales leadership stuff, but he’s so smart and he’s such a good person. Like he actually, you know, and that’s what my advice with salespeople is that you have to, you can’t find it out in the interview, but you’ll find it out in the first deals you work on together. What you want is someone who truly wants to look the other person in the eye a year later and feel really good about what they sold them and that they’re planning for their career to be long. They don’t see just a bunch of bridges to burn and short-term cash. They care deeply about whether that person is gonna be happy with what they bought or not. And you’d think that’s an obvious one. Really great salespeople all share that. That’s 100%. But a lot of effective salespeople who generate a lot of revenue for companies, I think also generate a disaster for companies because they just don’t fucking care. And that’s a way more likely person for you to hire as a salesperson than what I’m describing with Chris. That’s rare and you look for those people because finding someone who’s comfortable talking about the money, you end up having a high percent of people who are really douchebaggy and really sociopathic and capitalist climbers and all of these things. So there’s this thing like that, it’s like being comfortable talking about money. You have to be a fairly special person to be able to ask people for money and talk about money and feel comfortable with it and actually keep yourself really grounded. It’s easy to miss that. And then just go for like the what can they hit on total bookings number, but that’s the big thing with sales to be actually ethical and be matched to your culture.

Becky Mollenkamp:

Thank you for sharing so much around culture because I think that stuff is so important and really at the heart of a lot of what I’m wanting to talk about here is that, how do we make those shifts to create cultures that are people-first and focused on caring about our people. I wanted to ask you too something about abundance thinking because when I was listening to some of the things you were saying around happiness and that you can’t have happiness as your primary focus if you are, unless you have abundance, a more abundance mindset. But you know, most of us get really hardwired in capitalism to think in scarcity mode. That’s what keeps us in that pursuit of more, right? And so you also talk about abundance with time, not just money, but time and all of the ways to think about abundance. What were things that have helped you get to like, find abundance thinking and stay in abundance thinking?

Andrea:

I mean, listen, Katia Verresen is the one I credit for helping me realize this concept. And before then, I didn’t even know it. She helped combine one thing as CEO is recognize that words are magic, words of power. And I always thought that was true only for like, yeah, like, Gabrielle Garcia Marquez or Edith Piaf for like, you know, like these moments of like, but actually, every time you open your fucking mouth as CEO, it carries power to it and having her help me realize that. Then you realize that as a CEO in management stuff, scarcity of money is not a frequent topic, but scarcity of time becomes the number one topic all the time. And when I was at my worst as CEO, I’m so embarrassed, I go back in my mind, I have this vivid memory of walking into this meeting and there was a product manager, a UX person, a graphic designer, account manager, and they’d all worked really hard on this thing they were presenting to me. And I was like impending sense of doom, stressed as hell, and what I saw wasn’t what I was expecting. I didn’t like it when I saw it. And instead of saying to everyone, like what I would do now if I realized they worked hard on it, but it’s not what I want, yeah, it’s not where I think it should be for this client who’s trusting me, then you can use the right language and say, hey, usually there will be, there’s some really great elements here, and you guys captured some things. In that meeting, I had something interrupt me. So I literally said to them, because I had a crazy back-to-back meeting, I said to everyone in the meeting, ‘I don’t have time for this.’ It is such a hurtful thing to say. And they felt awful. So instead, like for Katia to help me realize a language change, to just say, we’re going to find time for this, we’re all going to nail it. It’s going to get exciting. Right now I have to run, so we’re going to make time tomorrow. We’re going to need more time than we thought ‘cause this one’s actually complicated and intricate. So, but we’re gonna figure it out together. I’ll be back to you soon. Thank you for putting this together. And nobody feels stressed out and harmed. But that scarcity of time thing gets in your culture and then everyone uses it on each other in this horrible way. And we’re late to due date and the drop-dead dates and all these terrible language things. So I think that pressure and scarcity on time, more than money. Of course, money is a major problem in many people’s lives, but in most of our tech careers and founders and what you’re dealing with, money you do worry about, do you have enough capital? Do you have enough to, can you pay the bills? There’s a huge stress around it. But the more present in your culture is dealing with thinking that we have enough time, we have plenty of time, we have an abundant amount of time. It’s a mind trip because society has us rigged to treat time like the number one scarcity that there’s no answer for.

Becky Mollenkamp:

Scarcity of time that creates urgency and it all feeds into capitalism. So of course it makes sense. I know our time is almost up. I have one question I wanted to ask you. If you feel like this is too big a can of worms to try and succinctly answer, let me know. But you wrote this really intriguing and I think maybe slightly controversial piece for Fortune earlier this year called “What the well-meaning critics of online advertising are missing and how they could hurt the communities they’re trying to protect.” Thought it was really interesting, I’m going to link to it in the show notes. Some advocates for marginalized communities are trying to ban relevant advertising, which is that advertising sort of is used to target a user’s search history and those sorts of things. And you said that can be a detriment to those very communities by banning that type of targeted advertising, it could actually be a detriment. Tell me a little more about that. How do you balance their concerns around privacy and safety with what you’re doing?

Andrea:

Privacy and safety is incredibly important. So what I never intended to say or imply is that we should be tracked as we move across the internet. We can’t be. Like take pride.com. You can have a kid go homeless because it tracks the activity. So they go to pride.com, read an article that’s fun. And later that night, their conservative parent goes to Fox News and gets a Pride ad and they’re like, you use the computer and it literally puts kids in jeopardy. So actually I believe and we’re working, we’re in final phases of contract with Google to work with our clients to provide relevant advertising contextual to what you’re reading at the time. That I believe is really wonderful, fair game. That’s where if I’m reading Pride.com, why don’t I get ads that are all supportive of the community? Why don’t I find all these vendors that I do it. if I’m on XO Nicole, which is for by black women for black women, why don’t I have more products and advertising offers? And right now, the way it works is that all of our advertising is not rigged to that. What we’ve gotten good at ad tech is violating privacy and tracking you all across so that oh, I saw you left this in your shopping cart and it’s very effective and that’s why it’s gone that way. That’s not the right way to go with advertising, but because there’s so much fear of advertising violating our privacy, I believe we’re missing the value of advertising done right, which is actually allowing narratives to be published and exist and stuff that I never had access to as a kid. But in a way that connects you to the advertisers that you want to see when you’re reading that content. And that’s the really important thing. So what Google has to do because of regulations on third-party cookies, we’re deep involved in in the separate world because we have all these publishers, etc. It’s going to be painful because it’s an effective way to monetize to violate our privacy, but it can’t be the right way. So what we have to do is build better ways to advertise and not abandon advertising because the concept of paywall is like, great if you can pay for the wall, but it limits access to narratives. So I believe advertising is fundamentally a very positive thing in our culture. If we can limit its privacy violations, you know, and keep it to an ethical place, then there’s a lot of room for that to be a really wonderful positive thing.

Becky Mollenkamp:

I definitely recommend people go read your piece because you talk about your own personal journey and what could have been made available to you, how that might have been helpful for you. And I think it helps people understand that better. So thank you for sharing that. You already mentioned, I always ask for a resource, you already mentioned…

Andrea:

Katia Verresen.

Becky Mollenkamp:

I will link to her in the show notes so people can go check her out. You mentioned she’s a CEO coach, somebody who helped you a lot, so I love that. And then I always ask at the very end for an organization that you support that’s doing good work that we can shine the light on.

Andrea:

I love TransTech Social. Angelica Ross is the founder. She’s amazing and gorgeous. And she’s an actress who’s super accomplished and just a wonderful human to support. And her organization helps people in the LGBT community grow in their careers and get access to job opportunities, etc. So I promise that money will go to really wonderful causes and you know, Human Rights Campaign, and Google, and Power to Fly and all these wonderful companies support them. So I think that was a really wonderful organization.

Becky Mollenkamp:

Great, TransTech Social, and I will link to that in the show notes. I’m going to make a donation to say thank you for your time, and hope that anyone who got anything out of this conversation, and I’m sure you did because I don’t know how you wouldn’t, I hope you’ll think about also going to make a donation as a way to say thank you to Andrea for her time for being here. So thank you so much. I think I could have talked to you for another hour, but I want to be respectful of your time. Speaking of time. And so thank you so much. I really appreciate it.

Andrea:

Thank you so much for having me. I equally could keep going.