Monica Enand is founder + CEO of a tech company called Zapproved. She grew up in a loving Indian-American family in Charlotte, NC where success for her and her siblings was one of two options — to be a doctor or an engineer. She chose the engineer path because she was good at math and science and learned to love being an engineer once she gained a mastery of it. What she really wanted to be when she grew up was President of the United States (I’d vote for her)! Her response: “we’ve gotten that desperate, I know.”
Always humble, Monica shares her passion for being engaged in the community started in high school and continues to this day with entrepreneurship + tech at her kids high school and with Techtown Diversity Pledge initiative. She got the idea to start Zapproved in 2008 when seeing this huge shift of companies needing to store their data in the cloud. The company started as a general document + message collaboration tool and quickly found its niche in legal e-discovery software. Monica has had to work through the narrative in her head that she learned in society and in her family that girls can’t do everything boys can do. She is proving that women are more than capable to run amazingly successful companies and be truly comfortable in their own skin — that’s what she values most in people and herself.
Ryan: Hey there, welcome to the Faces of Marketing podcast where we talk about the human stories and lives of different people and perspectives in the marketing profession and entrepreneurs and movement makers. This is your host, Ryan Buchanan, and I'm here with Monica Enand, founder and CEO of a software company here in Portland called Zapproved. Welcome to the show, Monica!
Monica: Thank you so much Ryan. It's a blast to be here!
Ryan: Yeah, it's great. We're sitting in your office here and I got a view from the Pearl, have some traffic on I5. And it's pretty awesome to see your journey and where you are. So we've known each other for about a decade. We've been in the Portland Tech entrepreneur scene. I kinda think of you as more of a legitimate technology entrepreneur, whereas I run a digital agency. Not only do you have the software engineer background, but you started a pure software company and it's done amazingly well. I've looked up to you, because at a time where my company went through our near-business-death experience, you powered through in the recession through pretty scary times and you came out the other side in a really cool way. You and I have had similar timing to our journey around equity and things like that, but definitely different ways that we got there. I'm definitely excited to dig into some of those conversations as we go through the podcast.
Monica: Thank you so much and absolutely - that respect and admiration is mutual for sure.
Ryan: Typically in this podcast, we go right into the chronological questions - where you grew up and all that and we'll get to that in a second. But, just to start the podcast off with a little bit of drama of how scary it was when you started Zapproved in 2008. And that's exactly when the recession started in probably '09 or '10. That is when it got like, "hey, we're starting to get customers, and I also employ a bunch of people and I'm about to run out of money." How on the brink were you?
Monica: I mean, it was a pretty scary time. I sometimes wonder if I look back and just think about how I had I led a charmed life up until then. It's scary always - it's just relative. I was lucky enough to go to a great college. I went to Carnegie Mellon and studied electrical and computer engineering and that was super hard. But, it led me to Intel where I was in a group that was really fun to be part of a lot of smart people. Well, I moved up the ranks at Intel. So to be honest, I had never really faced failure. And, I think that was the first time in my life where I think failure was absolutely ... I mean, the odds were much more for failure than they were for success. And that really shakes you to your core and you end up really stripping away lots of parts of your behavior and your personality and really figuring out your core. You find out what you can dig in and what you can really do. So it's a pretty transformational thing.
Ryan: Well, cool. Well, we'll dig into that in a little bit. With that said, so we're here in your office in Portland, Oregon. Um, but you grew up in Charlotte, North Carolina in the South.
Ryan: And you're Indian-American, correct? So what was it like growing up in the south? I went to school in the south, in Virginia, at University of Virginia, but I grew up in DC, so similar. We both ended up 3,000 miles away after college at Intel. We both started there and all of that. But I just find the culture back east is so different than here. And so what was it like growing up in Charlotte?
Monica: I mean, there was a fusion of a lot of cultures in my growing up. Like you said, I'm Indian American. And so, um, you know, we were very firmly rooted in Indian culture and participated in the Indian community in Charlotte, which was really wonderful actually in many ways for me. There was a youth organization, we had a little Hindu center where we would go and do all kinds of activities. I had a school set of friends and then I had my Indian friends. That was really healthy and really good for me. But it creates complications - the nickname is that we are kind of American, boring, confused, - the confused part is really that you're trying to balance the, the culture that you're living at school and the culture that you're living at home and you know, those differences.
Monica: And that was very real, especially as a teenager, getting into things like dating and proms and making choices about careers or making choices about schools are what you do which is very, very different. And then the southern culture - I really loved growing up in the South and I miss it. I go back and visit my parents and my mom and my brother and sister-in-law live there and I have friends there. But I've really become a good Portland citizen and really gotten used to that.
Ryan: What I love about the South is people value, just slowing down, taking the time for conversation and how people value people.
Monica: Yeah. There's a lot of relationship. So you do develop that relational value of talking to people, getting to know people, um, you know, trying to, trying to make every interaction that you have with somebody, a positive one, and now people genuinely try to make you feel better when you walk away from them than you did when you started the conversation. And I think that's like an important quality.
Ryan: So how did your parents end up in Charlotte?
Monica: My dad was a textile chemist. And so the textile industry in this country really fell apart while we were growing up in the 70's and 80's. He moved around from factory to factory. So we moved around a lot when I was very young. Then, all of the textile industry kind of fell apart. And my mom - very entrepreneurial of her - opened a little gift shop. We were living in Charlotte for one of those stints. He was working in a factory and she just anticipated that he would get laid off and that the factory would shut down. And so she opened a little gift shop and she actually did it in secret. She stashed away money without his knowing and started her company. It actually was able to make it successful when he finally realized it was successful and that he did get laid off. They actually opened a few more little shops and ran them and we stayed there. Luckily for me, I was able to stay there because I went to middle school and so I was able to stay there through high school, which I think was a good thing after having moved around so much before that.
Ryan: What was the name of the gift shop?
Monica: Elite Fashions was the first gift shop, but then they started opening gift shops in hotels, like in the Sheraton and the Hilton Hotel - and running those just like the little shops that have all the things you might forget.
Ryan: Okay. So when you were a little girl playing in the cul-de-sac in the suburbs of Charlotte - were you outside playing or were you reading books or what kind of stuff were you into?
Monica: Yeah, I was definitely an outside person. I think everyone was [back then]. Nowadays, people's kids spend more time inside. We were just all kicked out on the street and I just remember it being a blast. I don't think I became very studious until closer to high school. I got the chance to run around and do all kinds of things. My parents were pretty focused. They were immigrants. I was the fourth child. My dad was in a career that was going through lots of change and shutting down. So they were pretty focused on just getting food on the table and in having a roof over our heads. They didn't have a lot more to give me.
Ryan: So since you spent a lot of time with your siblings - you are pretty tight with them, right?
Monica: Yeah, they are quite a bit older than I am. So by the time I was 11 years old, they were all gone to college.
Ryan: Kind of like aunt and uncle roles a little bit? Or, more like your second mom and dad?
Monica: Yeah, definitely. Especially for my brothers, and my sister as well, they all kind of ended up taking care of me.
Ryan: And were they over-protective so you couldn't date anyone?
Monica: The nice thing was when you have immigrant parents, and they don't understand what it's like to grow up in this country, I had this sort of buffer generation of my two brothers and my sister who had grown up in this country. And that's I think why they became such important forces in my life because instead of going to my parents and saying, you know, what should I study, what should I do? They really ended up being the ones to kind of guide me in my life and career and they had a better understanding of life in this country. So it was, it was nice to have them. Yeah.
Ryan: So were you into sports or what kind of things carried you into high school?
Monica: In high school, I participated in some sports. I was never very good at them, but I was on the soccer team. Yeah. I was actually really involved in a service organization. And in my senior year, I was president of this service organization. I was pretty community-minded and I think even in the Indian community, I ran an Indian radio station on Sundays playing Indian music and reading the news from India. I loved being part of the community and being involved in organizing people.
Ryan: What nonprofit work was in the service organization?
Monica: At a high school level, we would do little fundraisers for the local community - different things for local organizations, very local and kind of focused also even on the high school, like raising money for things in the high school.
Ryan: I'm projecting some of this on me because I did a bunch of that in middle school and high school - but I can see how it set the bar for what you do now. You're super involved in Catlin Gable and that school's young entrepreneurs as well as TechTown Diversity Pledge and you're pretty plugged into the community here. So I think it a lot of times it starts at an early age. Did your parents get you into it, or what gave you the impetus to get involved in community stuff? Or was it your siblings?
Monica: Funny, my mom was into community stuff, and I think my dad never really was. I don't think he really had the luxury of ever being able to think about anything else other than trying to provide for us. So he never was interested. In fact, when I was interested when I was younger, he was discouraging of it, you know, he would go, "oh, why do you spend your time on those things? What good is that?" But my mom was always really encouraging and said, "whatever you do with the community, whatever you try to do, you learn something." And I think that's definitely true. My oldest brother, he's actually very community minded, loved being part of the community organizing things.
Monica: He actually organized an India Day Festival in Charlotte now. I had some role models that love to do that. And I think, like you mentioned, I've been involved in the school activities and, and kind of entrepreneurship with students. And every single time I've done it, I've walked away thinking - I mean there are moments where I go, "ah, how did I sign up for all this work?" - but then, there's always that after when you get it done and you have that feeling of, "oh my gosh, uh, I'm so proud of what we did. I learned a ton. I've grown as a human in so many ways." I think it's been really valuable.
Ryan: Yeah, it's funny. We were, right before we started the interview, you and I were talking, I took my family to see the movie "Blinded by the Light" and the dad similarly was working at the factory and gets laid off and his son gets a pro bono job at the Luton Herald, which is outside of London. And it's unpaid. And the dad's like, "that's horrible". But the son who is 16 years old, is on top of the world. The dad is saying "what's happening, what's in it for you right now?" Yeah. The reason I'm bringing this up is because I think it is a total luxury and it comes from privilege to get engaged in the community, and network and some of the things that we instill in all of these college students with the Emerging Leaders program is that whatever you invest your time into networking, it comes back to you tenfold. But it's not always direct. It can come up a year or two years later. Yeah. Um, it's such a, it's almost like we need to get out of our dinosaur brain and into a mindset where the future is all about social connection.
Monica: Absolutely. Yeah. Well I've thought about this in the context of immigrants and you know, immigration is being frequently talked about and having immigrant parents, watching my dad work so hard, my parents, my mom also, but also they came from that scarcity mindset. I haven't seen the movie yet, but I'm dying to see it. And I know it's about an immigrant family and I'm sure that scarcity mindset is that they can't really wipe it away. You really have to think about the time between now and the payoff comes when you least expect it. I've found the payoff comes at totally times you don't expect it. It's not even really a payoff. It's like thinking about Karma and just, okay, I'm going to invest, but you know, things that I invested in might come around way later. My kids went to a little Montessori school, and a friend and I chaired the school auction and we still work together today. She was one of my first angel investors. You never know what connections you are going to make and when they're in it, when it's gonna be something that changes your life.
Ryan: It builds so much trust on both sides when there's nothing in it for them in the moment. And it's just about that chemistry and connection and the more beautiful elements of human nature.
Monica: Well, I find that about business and I'm sure you, you and I have gone through of similar experiences and I think building a company in Portland, one thing I learned is paying it forward. There were definitely people who were very clearly paying it forward for me. They had been through experiences and were willing to share and guide me. And our team, Chris Bright and I, we take every opportunity that way it's just sort of like I said, karma.
Ryan: So I always ask this question every podcast. When an adult came up to you as the eight year old or 10 year old or 12 year old Monica, and said, "what do you want to be when you grow up?" What was your immediate response?
Monica: Yeah, I think on the younger end of that scale, seven or eight years old, there was kind of a running thing in my family because all of my parents were, you know, I have two older brothers and an older sister and they came from India in the late sixties. And then I was born here in the US and so the running joke in our family was that I was the only one who could be President of the United States. So they used to say, "well, you're the only hope in the family to be President of the United States."
Ryan: You're still our only hope in the country.
Monica: We've gotten that desperate, I know. But, I think when I was little, everyone used to say that and I've sometimes wondered, was that little joke was really confidence building. I think, you know, I quickly discovered I was not going to be President of the United States and when I got a little older, I don't think anybody asked me what I wanted to be and I don't think they thought I should think about it. It was just not something our family did. Everyone in our family went to school for computer science or electrical engineering or something very similar. We did that because that was what we believed would make all of us successful. And it wasn't about whether we liked it or not. I just don't remember anybody ever asking me what I WANTED to do. There's just expectations that, oh, absolutely certain thing. Oh yeah, we do engineering - it's what we do. Because no one ever asked me. I don't think I even had that thought. And, in high school I was good at math and I was good at science. So I think that's just what I always thought I would do. I just don't think that was even a time of exploration honestly in college. There was a moment there where I thought, "I don't know if I like this." But everyone was like, well that doesn't matter, just keep going. So I did.
Ryan: So it's fascinating cause before this interview you and I were chatting about our daughters, mine going into college in a year and yours starting up at Dartmouth, and I'm sure it's pretty different for your daughter,
Monica: It's extremely different.
Ryan: Because I was going to ask you before you answered that about you at Carnegie Mellon, which is an engineering type of school? Like did you always know that you wanted to be in tech? But you already answered that. Yeah. It's just what your family did.
Monica: It was and because I got into Carnegie Mellon and you know, my brother said you should just apply to electrical and computer engineering cause it was the hardest major to get into. And then once you got in there was no thinking about it really. I'm really happy that my kids have the opportunity to think hard about what they WANT to do. Sometimes I think they think a little too hard and overthink it. My son is going through a little bit of that right now and sometimes I do think, wow, it was a simpler time because we just powered through. And even though there were times that I thought I didn't like something, what I discovered later is once you get some mastery of something, the joy comes from accomplishing something and feeling that sense of satisfaction or mastery or being able to overcome hard things.
Monica: While I didn't raise my kids to think there's only one job and you have to pick that as my parents kind of believed. There were two jobs that could have been a doctor or an engineer. Those were the two. Those are the only two choices in my parents' mind. And I didn't raise my kids to think that there was something good about saying, hey, it's hard. You're going to still do it and you're meant to do hard things and you're going to be fine. You'll get through it. I've had to summon that multiple times in, in life and it served me well to have that experience.
Ryan: Yeah. I'm reading this book now by David Brooks. He's The New York Times columnist and it's called "Double Mountain." The first mountain is success in life and the second mountain is significance. And one thing that I had never thought about until now is in American culture, we're so much about freedom of choice, freedom of you can do anything you want. Yeah. You know, all that. And that is crippling with anxiety, especially as a graduate from college. You've majored in whatever you wanted to, and now the realities of "what are you gonna actually do" is really, really scary. There's gotta be a happy medium in there somewhere.
Monica: Yeah. I think it's a hard question to put to our kids to say, "find your passion." Yeah. I think that's an incredibly difficult thing because what if you don't know what you're passion is? I mean, I don't feel like I understood what my passion was until my late 30's until I started Zapproved, until I realized that entrepreneurship was a thing and that I actually could do it, which took me until relatively late in my career to figure out that I could even do it. And now I realize, wow, that is my passion. I love businesses and I love building them. And I love how they grow. But I didn't know that.
Ryan: So yeah, I was going to ask this. So when I ended up right after college at Intel, my motivation was that's gonna get me to Portland and employ me and then I can do all this fun stuff once I'm here. But when I was there, I was just like, "oh, this innovation stuff in tech. Like this is like the things that consumers consume and how we live our life is so influenced by technology and it's, it's so helpful." And so I just wonder, before you got to your mid 30's when you started Zapproved, I'm sure there were elements of technology that you got passionate about.
Monica: Oh, absolutely. Yeah. I loved working at Intel. I came not knowing much about Portland at all, but knowing that Intel was an amazing company and that they work in this really cool microprocessor, and I wanted to be part of smart people all around. I felt like the dumbest person in every room, which I think is a good thing to try to be the dumbest person in every room. It was really an exciting time to build something that, you know, if we look back on just even the last 20 years and how much the world has changed and how much a part of we that we were in building faster microprocessors or whatever it is.
Ryan: So you go off to Carnegie Mellon and there are moments where you're like, oh, I'm not sure I'm into it, but then you had success and that was a driver to power through and, and get to a place to where you then go to Intel. Let's start shifting into Zapproved because that was such a foundational moment for you. What's the origin story of how you started Zapproved?
Monica: I only quit Intel because I was having kids. My son was 18 months old and I was pregnant with my daughter and my husband worked for Intel. We were both working crazy hours and we realize this was like not a way to...
Ryan: How long were you there?
Monica: I was there about seven and a half years. And we both said, "hey, one of us is going to have to quit." And we talked about it a little bit and decided that I would take some time off and take care of the kids. I sometimes look back on that and wonder if I had never done that, would I have ever left Intel? I don't know if I would've because I really did love my job there. But having that break away from Intel and spending a few years outside of it and then just wanting to observe technology and what was happening and looking at it from afar, that was what got me excited about software as a service.
Monica: What was happening with the cloud and entrepreneurship. I had gotten bitten by the entrepreneurship bug in that time. Just reading different stories and seeing different people - either friends that I met at Carnegie Mellon and Intel or my brother also did an entrepreneurial journey and realizing that it was super cool. So when I finally decided that I'm going to take the plunge, which was, as you pointed out, 2008, and I quit my job. I had gone back to work actually for another startup to learn a lot about startups and how they worked. I then decided to quit that job, take some money out of my savings and go ahead and give it a go. I started building Zapproved and recruited a few people to help me.
Monica: We all worked together in my house. And then the recession hit and it really became very clear that this was not the best time to choose, with the economy falling off a cliff. In retrospect, it ended up being a really good thing for us, though it was really painful. One of those times again where you have to go, "wow, I don't know how we got here, but we're going to have to power through because this isn't the place I want to be at this moment, but if we can power through, it's gonna lead to something good."
Ryan: So one of the places where we're a little different is when I started my company, I was 25 or 26. And, I always say that being really naive is very helpful in becoming entrepreneurial, but I didn't have that much to lose either. I had just gotten engaged, no kids and I could fall back and go back to work. I mean, you could definitely do that, but you have kids, and you're mid career and in your prime earning years at a safe company like Intel, all of that. I guess those become really big motivators. Like, "I've got to make it because I've got to do this for my kids." But it's almost scarier - what you did.
Monica: Well, I have to say, the one thing about my situation is because I was a stay-at-home mom with a husband that was working at Intel and a really supportive husband. Maybe it's like a Sheryl Sandberg thing saying, "you have this really supportive spouse." It makes all the difference. It really did because we had learned to live without my salary. Now, we had not learned to live with me drawing on our savings on a regular basis, which is what I did for
Ryan: going negative.
Monica: Yeah. Going negative was something new that I was doing and I knew that I couldn't sustain that, but we had learned to live and he was very supportive. He was very much like, "I do love working at Intel." He loved his job. He loved the technology that he was working on. So he said, "I love it. I don't want to quit. I don't want to do anything different. So if you want to do something and try something, go ahead." I was lucky in that way that I had some buffer and some feeling of - it wasn't about food on the table.
Ryan: Yeah, that's huge. And one of the things that I connected with when I heard parts of your story that just recently aired on KGW, which was pretty cool, uh, is that you also had other family members like your brother step in financially when it that support is above and beyond the call of duty and so heartwarming when family members step in and just trust you.
Monica: That's where you feel like you do get recognition and it feels good. It feels good, especially for my team when we get recognition. But I do recognize the privilege that I have. I definitely came from a more privileged position than a lot of entrepreneurs. I did have that support when I almost ran out of money from drawing negative on our account. My brother stepped in and gave me money. I had a mother-in-law who actually help take care of the kids so that I could travel a bit and supported my husband. So I had all kinds of support and I really do recognize that privilege, it would have been impossible.
Ryan: Yeah. I mean, I feel like without a supportive family or safety net, entrepreneurs have to have really good partners and investors and create a family basically. It takes a village to raise a kid - it takes a village to raise an entrepreneur. And if you don't have it biologically, you have to create it.
Monica: Those are the people I really admire. I've met a few of them and think, wow, that's crazy. Doing amazing things.
Ryan: Awesome. So, you're not a lawyer. Legal software - that happened because it wasn't like, "honey, I've got this great idea. We're going to do legal software and it's going to be amazing."
Monica: I'm super passionate about litigation support. No, no, no - it didn't work that way. I did become pretty passionate about software as a service and built Zapproved, which was originally just a tool for keeping people organized. I was really fascinated by the big amounts of money that were going into that and what the economic change, especially given that mobile was on the rise and knowing that we'd have to have thin clients and data would have to be in the cloud. So those were the trends I was seeing. I don't think entrepreneurs can time the market, by the way. I was bad at timing the market, but I think you can look at trends and say, "okay, these are trends that are irreversible and you position yourself as a good entrepreneur positions themselves to take advantage of and ride that wave when the wave crests, then ride like mad. So things like the growth of data, and the fact that mobile was there, you know, it was clear that things were going to the cloud. So being cloud-based was really important. We went to Beta with Zapproved in August of 2008 and we got great reception. All kinds of people were using it. We had thousands of users actually across all industries.
Ryan: You didn't have a niche. I remember meeting you. At that point, it was just like, oh, this is cool, but I can't quite place like how I would use it.
Monica: Yeah. And people were playing with it and using it for different things. But I was in this sort of exploration phase of like, "Hey, we'll just put something out there and see." I had some hypotheses about different industries and how they would use it before we built anything. But I was trying to validate that and then also trying to explore and keep my mind open to other things. But then in September, Lehman Brothers failed and the market started to crash and it became really clear that when we looked at our users. In the winter of that year, 2008, we sat down and did an audit of who all was using the software and why. And it became clear we were going to have to pick one thing, be the very best at it - because that was picking a niche and being really good at it was probably the only way to make it, because we weren't going to raise large amounts of money.
Monica: And then having that be non-discretionary spend - something that was somewhat recession-proof. And litigation is typically counter recessionary. Um, now it wasn't in that recession because that recession was so deep, but litigation didn't dip as much as anything else. And also we knew that with the world, if you know that the world is changing in terms of the volume of data, and you also know that part of our litigation system is that you can't delete data that's potentially relevant to a case and that's a fundamental tenant of the judicial system, right? So those things aren't going to change and the problem's going to go from 100,000 boxes of paper to terabytes and terabytes of data growing exponentially and living in all different locations and all different types of data, whether it's text messages or video or pictures or all of the different things that people that corporations are going to deal with that you know is discoverable - Slack messages - just everything.
Monica: So you know that the complexity is continuing. There's no reversing that. And you know that the fundamental tenant of our judicial system is that data relevant to the case has to be preserved and turned over to the other side. So at least it felt like this was the right horse to bet on because it was clear that it had a big problem.
Ryan: Yeah, absolutely. But other folks have come into the space. You've kind of validated it well and there were others in it.
Monica: Yeah. We took a more modern technology approach. Yes. Yeah. We didn't build anything new and we still aren't, we're really deploying it in a different way. And really the other difference is that our competitors focused on law firms spend because that's where the money was.
Monica: They really tune their products to be easy for law firms to use. We really focused on the corporation. And that gave us the Intel in-house counsel - many of the big companies - using our product, but we focused on the in-house counsel and putting ourselves on the side of that person. You know, legal is not an industry that has been known for efficiency. The incentive structures for efficiency when you're charging by the hour. It's a complicated structure to get a lot of efficiency out. And it's been that way for too long. But it's at a breaking point just with the growth of exponential growth of data. E-discovery is a large driver of cost and litigation. So we knew that, okay, this is unsustainable. There is going to have to be a forcing function for the efficiency motive and aligning ourselves with the corporations who are going to push that efficiency - it felt like the right thing to do. So that's the kind of different take that we took on it.
Ryan: Now I get it. Yeah. And so you're now a hundred and something employees...
Monica: 160 bursting at the seams here.
Ryan: Yeah. And recently got acquired by Vista Equity Partners. So they acquired you and they usually have a four to six year window to add value and.
Monica: Yup. That's about right.
Ryan: Yeah. There's a lot of myths of private equity, but very often you don't see the entrepreneur about a year later, but you're still here. So you must still be liking it.
Monica: Yeah, I'm, I'm learning a ton and I've learned for myself that I like to be constantly growing and so I'm really thankful to be working with them and have them behind me. When I first thought about doing a transaction with them. I had kind of a lot of the same impressions of private equity and they invited me to a CEO summit and I met tons of founders. So I actually spent some time with Reggie Agarwal, who is the founder of Cvent and is still with Cvent. He was on the public market. They bought it. They acquired his company off the public markets, took it private. So there were a number of founders there and I realized, you know, that that team really understood what founders bring to the party and they were very excited about working with founders. And the other thing I realized is at the size company that we were, we weren't huge there. Their old playbook wasn't gonna work. So they were absolutely interested in growth and interested in growing the company and focusing on top line growth and not focus necessarily on cost-cutting. Or roll-ups or, I mean they have those playbooks but that's not what they're doing in this fund. This is a part of a new fund that they started.
Ryan: Okay. I'm going to go backwards a little bit. You were talking about data being the core of your business model. This is, it's really an entrepreneur podcast, but we also talk about marketing and we in digital marketing are all about data and those insights and how that informs better marketing campaigns and things like that. Does data in your marketing department for how you market Zapproved to these corporate in-house counsel folks? Do you use that there? And how does that work?
Monica: Absolutely. I mean I think the first thing that we did early on was, and I think it was because we weren't attorneys and we were trying very hard to understand the market. We ended up doing a lot of curriculum marketing. So we would read case law, and write about it, and write our summaries and our positions and point of views and send it out. It turns out we were doing it because we were trying to educate ourselves. It turns out that many of our customers were really appreciative of that kind of 'cliff notes' or 'for dummies' versions because they have to stay up on all of that. You know, there's continuing legal education and credits. It's a moving target - art or science or I guess more art. You have to stay current. And so we got a lot of following because of that curriculum marketing.
Monica: And then we started to learn and study like, Hey, the people who are usually interested in these topics are the ones that seem like they are sophisticated in the way that they think about innovating. The analogy - it is going from a reactionary fire department - waiting for the fire and sending out a firetruck, which is really costly for corporations and really trying to be proactive and treat the business and the General Counsel's office into a business center that anticipates things and treats litigation as a regular business practice.
Ryan: So you could prove to those folks that if you, if they used Zapproved and were proactive, it was a hundred times less expensive.
Monica: Absolutely. Okay. And when you say 100 more, it turns out that the ROI, because there hasn't ever been this efficiency motive and the play is always kind of the same for every case - being proactive and thinking about your case early on, especially when data is growing at the volume - it really saves costs downstream. The opportunity for creating ROI is huge. In our marketing, because we were putting out all this thought leadership and curriculum marketing and we were participating and interviewing people - kind of like you are doing webinars with customers and thought leaders - we started to realize who were the people who had a propensity to buy and were ready to take on sophisticated technology to help to try to move their organization forward.
Ryan: There's very few companies that directly use data like you have in your marketing campaigns, like, and that you were speaking the same language as your clients, how you format it and all of that. But I find there's so much talk in all these marketing conferences you go to around big data and how to get smarter and all of that, but it's often siloed or used very ad hoc and not integrated into an entire marketing effort. But it sounds like you've done that.
Monica: Yeah. We've really focused on where do we spend our energy marketing and marketing against? I mean really the marketing is really trying to make sure that the sales people are spending their energy where it can be fruitful. And that's where all the data analysis goes. We believe every corporation should be using our product? Of course. Is every corporation ready right now? Not necessarily. So what are we using the data for? We're using the data to figure out who's more ready based on buying behaviors and buying signs.
Ryan: A propensity model to buy.
Monica: Yeah, absolutely. Readiness.
Ryan: Just a couple last questions. Who in your life, and it doesn't have to be an entrepreneur or anything like that, but someone who really inspires you?
Monica: I've been thinking about this question for a little while and
Ryan: So there's a lot of people out there, so it's kind of a hard one to narrow down.
Monica: I think what I've learned over time is that it's changed for me. You know, I probably would have said in my younger days, I might've said, "Andy Grove" or Elon Musk or Steve jobs or somebody like that. You know, somebody who's a technologist that I really admired. Although the older I get, the more I discover that. I think it's people that have done the work to figure out how to be comfortable in their own skin. Recently, I read her book and then listening to Michelle Obama. It's all about just the fact that you've done enough work to understand who you are and get really comfortable in your own skin. I think that's like my definition of success anymore. And I still struggle with being comfortable in my own skin.
Monica: It's constant. Like it's a constant struggle. I never had that feeling of even being comfortable in my own skin until probably maybe 4-5 years ago. I got a taste of it and then it's been this continuous journey to try to be that more often and kind of authenticity. And I read Brene Brown and I think she's awfully inspiring. Thinking about how to really get to your true authentic self when you're an overachiever and you're used to accomplishing things. You draw some self esteem from that and you have some confidence but you also have some imposter syndrome because you're trying to do something new that and blaze new trails. I think that whole thing is just been where I been spending my time and when I meet people that, that feel really comfortable, authentic, that themselves, that's what I find really inspirational.
Ryan: He's had this thought as you were talking where you mentioned some amazing women with Michelle Obama and Brene Brown. I find that the more comfortable in your skin you get, it's almost like it becomes a little bit of a target for others. I'm thinking a little bit of Trump right now, so sorry. For other people to attack and like throw you off your game and you have, and it has to be for Michelle and Brene really hard to not want to fight back to the haters. "When they go low, we go high." To live into that because you want to say, "no, like that's not how I am. This is me, but it's just got to take incredible self-discipline to stay comfortable in your own skin and not give energy to the attackers.
Monica: Oh, absolutely. And you know, you mentioned your dinosaur brain or your reptilian brain - we all have that scanning for threat. Our amygdalas are always on, everyone's going to have that fight or flight response. But it is a practice thing. I do think it's a practice thing and I think, you know, it's one of those things you're gonna always aspire to and never ever achieve because you're never going to be 100% good at that. But you have to just keep trying.
Ryan: Yeah. That's cool. I love your response because I don't know how I would answer it. Part of that question comes from a dinner table conversation that I've had with friends where it's, "who's your hero?" And it came from a place of when I had my near business death experience, I was in a place very ego-centric and all that. And so my heroes were the software entrepreneurs and the people who've made it big. And then the more I've grown, self-aware and know what I value, it's like, "Oh, both my parents are entrepreneurs. Like my hero is my dad for his work ethic and for like principles and all that. And for my mom for just being so dynamic and so magnetic and loving. It's so different than10 years ago where my inspiration, my hero were people I didn't know. It was about fame versus who your heart and soul attaches.
Monica: Yeah, absolutely. And realizing that it's dangerous a little bit to have heroes because everybody is human. They are all just people and you can't create too much expectation from anybody. Um, because it's not fair. It's not fair.
Ryan: Yeah, absolutely. So last question. Um, and so the premise of this question is that there's often a life moment that happens. Sometimes it happens in high school and college right after, um, where it's either really, really hard or it's something that is life giving and it creates independence and gives you a ton of confidence. And in any of those scenarios it builds perseverance, grit, all of those things where it's not surprising that I, Monica am CEO of this company and I'm super proud of the team here and all this stuff. Can you describe a moment or a part of your journey that you can look back to and say, "oh, this was pretty defining."
Monica: Yeah. Personally I think, um, you know, we talked about a lot of the privilege that I had as an entrepreneur and I'm really grateful for all of it. I don't know if it's fully gendered, but I do think many times in my life, and I'm sure men have this too, people talk to you about what you can't do. Well you can't start a company because what do you know anything about that. Even my mom would say that and she was a business owner who started her own business, but she would say, "well, girls don't do that because they get pregnant." We grew up with that narrative of "you're going to have to have babies and some someday you're gonna have to do these things and you can't do everything that boys can do."
Monica: And my parents very much treated my two brothers very differently than they treated me. They thought all of us were smart, but they very clearly knew that there were things boys could do that girls couldn't. And I think, there's messaging that constantly feeds in your head and you just live with that. And I think it was, I was working for a startup locally by a male founder and the founding team - all three founders were men. I was working really closely with them and I got to know all three really well. And there was just a moment where we were discussing something around a specific decision for the company, and I knew I was right and they were arguing with me, two of them in particular, but one of them very vehement, the CEO.
Monica: I knew I was right and he was wrong and he insisted that I was wrong and he insisted that we do it his way and he was the CEO. So, you know, you have to disagree and commit. And at the moment, I disagreed and committed. I thought, oh, he doesn't know that - he's not right about everything. Now again, like I said, you can't make anybody a hero. You can't make anybody because they are just human. Right? And he had his reasons for thinking. And I think at that moment I realized no one does know everything. And I don't know why. Like if you wait until you know everything, you're never going to be able to do something and no one else is waiting. So why am I waiting? And that was the moment I said, okay, I think, you know, I'm going to help you finish this, transition, this, but I want to start my own thing and I want to, I want to go for it. Um, and that was a really pivotal moment. Like, you know, there's all these brain studies, but like I remember exactly where I was and what I was doing, what I was wearing. You know, you remember all the details of that moment where the light bulb goes off and you say, screw it, I'm doing it.
Ryan: I can identify on the male side of that that because there's data that shows that applying for jobs, women will often self-select out if they don't meet all of their requirements of the job description. Whereas the guy, we'd be like, "Oh, I've got like two out of the 10, I'm good." Yeah. And I am exactly that way. And I have two sisters - I don't have any brothers and my mom's is a super strong entrepreneur and a role model that way. And one of my sisters is an entrepreneur, and I haven't had that conversation with them, but for me, I knew I could start a company even though I knew nothing about. And that was fully male privilege. I just fit exactly into that, you know?
Monica: You're so awesome for recognizing that and knowing and educating yourself as much as I know you have and how hard you've worked.
Ryan: But I think 11 years ago, that you had that kind of aha moment. If you were to be in a conversation as say the chairperson of the Board with three founders who are all male, would you lean in a little bit stronger and say, "you know what, I know you think you're right, but we really need to get this right."
Monica: Yeah. Oh definitely. I mean it's a beautiful thing to have these moments of confidence, right? Because we all live in this place where we're always doubting ourselves and worried, but there is this moment of, "I know I'm right and I know that's the right thing to do and I want to go do it. And if you don't want to go do it, that's your choice beause this is your company, but I'm going to do it."
Ryan: And you're so humble that I would imagine when your team does hear you with that level of clarity, they're like, "okay, we know what we're doing." Does that happen here?
Monica: It does. But you know, you have those moments of confidence. But one thing I've learned in the last 11 years is that things are not always what they seem, and you have to be skeptical of yourself all of the time because there are times where I've thought I was 100% right and I made the wrong decision, but you can't let that paralyze you either because I've had that happen and I looked back and thought, "wow, I was so confident I was right on that." Whether it's a hiring decision or a market decision or an interaction with a customer or a negotiation that you're hunting - you just feel like you're 100% right. But, you can still be wrong. It's great. That's why it takes a lot of trust. Trust is built on vulnerability. So being able to be vulnerable with your team is where you can create those trusting environments where you can create healthy conflict. And when you can have healthy conflict like that, that's where all the growth happens and the magic happens. And that's where you walk out of the meeting with this great sense of satisfaction that you just had a wonderful deep conversation and considered all the aspects and really thought things through.
Ryan: So few companies create that healthy conflict culture because it's initially this notion of "bring on pain" and humans don't want that, but the benefits are huge. If you can create a scenario that is vulnerable and you know that.
Monica: I don't know how you feel because you also worked at Intel when you were young, but I felt like, because I was 20 years old when I started working at Intel, and Andy Grove was the CEO then. I remember him walking the halls. I remember having a brown bag lunch with him, and that guy created conflict like nobody's business. So I did get really comfortable with that conflict, even though I don't think it was always role modeled in the healthiest ways at Intel. And I think there are healthier ways to create conflict and create psychologically safe environments and where people have hard conversations with grace. Yeah, for sure.
Ryan: It's so awesome having this conversation. I always love getting to know my friends that much better and thanks so much for being on the show!