Jessica Ewing: Founder & CEO of Literati

Episode 296

Listen as Jessica Ewing, Founder and CEO of Literati, shares how being an unapologetic lover of literature can be the inspiration behind starting a company to make a difference in the world. Her company Literati aims to elevate literacy outcomes by connecting readers with books they love. And of course there is some technology involved behind the scenes. Her initial focus for the product is kids, but she shares how expanding to other demographics could be in the mix soon. Want to know about fundraising? How she did it? How starting her career in product management at Google, and co-owning five different patents in consumer technology design, were just some of the cool things that she did along the way and what she learned from her achievements too. Let’s just say that Jessica is not an underachiever! Thrilled for you to hear all about Jessica’s lessons, Literati and more. You don’t want to miss this incredible episode from an amazing entrepreneur. Today on #TheKaraGoldinShow.

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Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be I want to be, you just want to make sure you will get knocked down but just make sure you don’t get knocked down knocked out. So your only choice should be go focus on what you can control control control. Hi, everyone and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi, everyone. It’s Kara Goldin from the Kara Goldin show. And I’m so thrilled we have our next guest. Here we have Jessica Ewing, who is the founder and CEO of a very, very cool company called literati. If you are an unapologetic lover of literature, what kind of startup do you go and create? Well, Jessica can tell you because that’s exactly what she did. Her goal was really to elevate literacy outcomes by connecting readers with books. Initially, starting with the kids line, I certainly hope that they go a lot further and expand into lots of other readers as well. And hopefully she’ll get into that a little bit. But she became an entrepreneur after starting her career in product management at Google. Oh, and she is a co owner of five different patents in consumer technology, by the way, consumer technology design, a little bit of an underachiever now, not really, I can’t wait to hear more about her journey. And like I said, After experiencing her company, and watching it grow, I was so so thrilled to be able to have her here with us today to hear a little bit more about her experience. So welcome, Jessica.

Jessica Ewing 2:10
Thanks, Kara. It’s really great to be here. Excited to chat with you today and get into all the things

Kara Goldin 2:15
Awesome, awesome. So let’s start at the beginning. I think in Silicon Valley, we call it you know, the elevator speech. So how would you describe literati? And what you do?

Jessica Ewing 2:27
Yeah, absolutely. I mean, at literati, we’re really trying to find, you know, the perfect books for kids at the perfect time, you know, and kids, you know, they’re changing, and they’re growing, they’re adapting, you know, and parents are busy, you know, finding the right book at the right time can be life changing. I mean, I think that we all know that, you know, as, as adults, you know, you find a certain book, and it affects you in a certain way. And it’s just a really important, you know, problem to be solved. And so we’re aiming to really solve that problem through, you know, a variety of products. We’ve got a kids subscription book club, we operate school book fairs, we even do some some original publishing as well. But yeah, we are, you’re really trying to focus on finding books that help kids really deepen their interest in subjects and spark new interest in other subjects.

Kara Goldin 3:15
That’s so cool. So let’s back up a little bit. You I mentioned that you were in product management at Google. And so I get asked this question, when I’m speaking on college campuses all the time, should I go and start a company? Or should I go and work for a company and my experience was actually working for initially in media, and then in tech, and so and then starting my own company, eventually, but I found actually going and working for incredible companies and people more than anything, was able to gain confidence, and plus, come up with the right idea that I really wanted to work on every single day, but I’m curious to hear what your response is.

Jessica Ewing 3:58
Yeah, absolutely. I mean, I started it at Google, you know, just right out of college. And, you know, my background was more technical. I, you know, I studied symbolic systems in college, which was a mixture of kind of computer science, philosophy, psychology, and, you know, and I really just, you know, I started out I just was, you know, my parents were just hoping I was employable, you know, like, right out of school. And so, I mean, Google was my first job, you know, out of college, and I was thrilled to, you know, to get in the door, and it was a smaller company back then, I think it was around a 2000 person company. And so, you know, being I think it grew and I believe in the time I was there, it grew from around a 2000 person company to a 20,000 person company. So, wow, seeing that growth trajectory firsthand was, you know, extraordinary and, you know, and and I think at that young age, just being able to kind of rub shoulders with some of the, the great minds that are in a car somebody like that, at that, especially in that early time? You know, it was an extraordinary experience. I think, you know, the only really misgiving I have about it was was funny because you asked this question of, you know, do you start your own company? Do you work for someone else? And you know, and it’s it’s a, it’s a, you know, it’s a tricky, it’s a tricky tension, because the answer is not the same for everyone. You know what I mean? Sometimes you need to stay with the pack. And sometimes you need to break from the pack. And it’s it, can you know, what I mean? And it can be difficult to know, is my growth in in sticking with this pack? Because this is the right pack for me. And, you know, and I’m doing important work, and I’m learning things, or is it time for me to really break from the pack and kind of start over and start fresh and, and find my own voice and my own footing? Like, is my voice being amplified by my pack? Or is my voice? Am I losing my voice, my authentic voice in in this pack? You know what I mean? And I think that that’s some some of the some of the tension that I think we all feel, I didn’t leave Google to start a company, I left Google to be a writer. And so that was the big move. For me, it was just a move from tech to the arts. And I wanted to be in you know, books and literature every day and and accompany was was nowhere on the radar at that time. But you know, things happen, and you grow and you change and the arc of the story goes from there.

Kara Goldin 6:28
It’s interesting hearing you say that you were at Google, when you know, there were a couple of 1000. I was at America Online, when it was kind of a similar situation where it went through that hyper growth. And, you know, definitely, I didn’t even know what a hockey stick was until I was in it. Right. And, you know, I, I was actually working out of San Francisco, but the main office was in just outside of DC and Virginia. And, you know, every week I would show up, and there’d be new people. And you know, and some of them work for me, right? It was just Yeah, it was crazy. And anytime I experienced that, it’s really hard to describe to people if they haven’t been through it, and obviously you have been through it, I think the other thing that I really gained, as I look back at that experience is that I really loved the build, right? I loved the early stage, not just maintenance, I loved kind of the creating and, you know, building outside of the box. And but I didn’t know that until I actually started my own company that that was really what was really exciting to me. So I think that that’s another really big point as well, you know, just in terms of wanting to do something different. Sometimes people say like, you’re saying you want to be a journalist, but then you went and started a company from it. So you know, it’s definitely everybody’s journey ends up being different. And it’ll be interesting, though different.

Jessica Ewing 7:54
Yeah. Yeah, absolutely. And I mean, I think that like, if your journey looks like anybody else’s, you know, your path looks like anybody else’s. But you know, like, it should, you know, it’s not going to, you know, an authentic path is going to look so unique. And sometimes, when you’re in it can be just so twisting and turning. And you’re just like, why am I here? And it kind of like all comes together? I think when you look back at it, but like when you’re in the moment, you’re just like, what, what, why am I here? What is going on? What am I doing? You know, what am I doing? You know?

Kara Goldin 8:27
Well, and obviously there’s a tech angle to you know, what you were doing at literati. So Well, before we even get into that I’d love to hear so, you know, you made this decision to actually start the company, which came after you decided to be a journalist. So what, what was that jump? Then? What, like, how long did it take all of those kinds of questions? Yeah, the

Jessica Ewing 8:53
things Yeah, I mean, I left Google. And, you know, my goal was to just be a writer, I wanted to spend the rest of my life writing books and I, you know, I, I started working on a novel for for five years, and I just, you know, was working alone. I thought that this was going to be the rest of my life. You know, I thought that, you know, I had always loved writing as a kid for a while, like, you know, if you had asked me as a kid, what I wanted to be was always, you know, some combination of a screenwriter or, you know, a novelist or a playwright, or it just, it would always involve the written word. You know, I was, I was in my, my mid to late 20s. When I left Google and, and, you know, it was not a popular choice, you know, like leaving, leaving, secure, you know, tech job with free food and snacks to go, you know, at the time, I was sort of wandering around the desert, like writing a novel around living off the land and, like the juxtaposition between In the world of tech in the world of nature, and, and sort of those different parts of ourselves and our sort of rational side, our intuitive side, our analytical side, our creative side, I mean, these were tensions that I felt deeply inside myself. And this is the these were the tensions that I was, you know, kind of exploring in, in my work, and, you know, and I spent five years trying to, you know, piece this together. And, you know, I discovered a lot of things during those five years, you know, first of all, I discovered that, you know, fiction is really difficult fiction is really hard. And fiction is harder, I think, then, for me than nonfiction, you know, in many ways, and, you know, trying to piece together this novel, and what I will say is that, you know, you talked about how you discovered, you love to build, you know, after five years of writing alone, then going and trying to find an agent, you know, finding a publishing agent, and, you know, learning about the world of books, and publishing and literature, and I felt this desire to build again, and I didn’t ever think I would, you know, I didn’t, I thought I was done, I thought I just was going to be an introvert and isolated and just, you know, write my write my books, it took five years for that, that impetus to kind of find itself. But once I had like this small team going, and we were exploring ideas, and I was building and creating products, again, it was just like, wow, wow, like this is I love this, you know, I miss this, I miss being part of a team, I miss creating things with people. And this is so much fun. And I think literati for me is kind of the marriage of those two experiences, you know, in there to kind of extreme ends, I spent five years doing consumer technology, building consumer technology, you know, Google, and then five years basically exploring, you know, my own creativity and literary voice in isolation. And literati is sort of the marriage of the two.

Kara Goldin 12:06
So was there anybody or any specific instance that sort of led you to think, Okay, I’ve got to really focus on literacy, because there’s a lot of journalists that are out there that, you know, want to write and whether it’s books or articles or any type of medium, but then they’re not thinking about creating a mission driven company like you have. So I’d love to kind of connect that, yeah,

Jessica Ewing 12:34
yeah, I moved to Austin, and I thought I was going to work as a writer and start, like, like, right in the morning and start a company in the afternoon, which was totally crazy, right. But I didn’t actually want to totally give up writing. I just was like, Oh, I just, I want to start this business. And I saw so much opportunity in the space of books and literature, actually, because if you look at the sort of Venn diagram of the people who, you know, do tech, and the people who do arts and literature, that it’s a small overlap, you know, it’s not, it’s not, it’s not everybody, right. And, and I just saw a lot of opportunity. And I think that, you know, I was exploring a number of ideas in of, for startups in the books and literature space, and I saw a number of different problems that, you know, that needed to be solved, you know, how do you connect a writer to an agent or a publisher? How do you discover? How do you discover which, which books are, you know, out there? What are what are the unfinished manuscripts in people’s desk drawers that, you know, that are dying to, you know, just to come out and to be finished? How do you market a book? How do you discover a book? You know, and then more on the consumer side? How do you? How do you solve the paradox of choice problem, because there’s just millions of books coming out every year? And it’s like, how do you find the one? You know, how do you sift through everything and find the books that are that are right for you? And so I became very fascinated with this discovery problem, you know, so I would say, like, I went from being a writer trying to sort of figure out how to sell my own work, to thinking about how did people discover books, you know, how do you how do you discover great books and and that was really where I was sitting with my best friend who had just had her first child. And we were talking through this problem, specifically, this problem of how do you how do you match someone with the perfect book? Like, what is the mechanism for doing that? Is that is that mechanism broken? You know, is that discovery mechanism? Because it’s changed so much over the years, you know? And she started sharing with me, some of the books that she was discovering for her, her newborn son and some books that a friend of hers where she goes, You know, I would be lost without my friend, Haley. And I was like, tell me more about that. She said, Well, you know, this problem that exists of finding the perfect book, she’s like, I can’t tell you how much how much harder this problem is for finding books for my son. Because I don’t know, you know, I just became a parent. And so like, the only books I know are, you know, for kids are are sort of, you know, sort of classics or you know, what I grew up with as a kid like I don’t, and I don’t even have time to take shower, like, let alone scour around and find, like, curate this, like, perfect, but but she understood the importance of reading, she just had no time. And so, so I remember sitting with her on the couch, and you know, in her sharing with me, she said, You know, I would be lost without Haley. And I’m like that she starts handing these different books to me that a very smart friend of hers who knows children’s literature was curating for her and she’s like, look at this, look at this isn’t this genius. And so we were sitting on the couch together, and she’s like, isn’t this genius, and she would pass me these different kids books, and we would laugh and laugh. And, and it just, it was like, that was the moment where I really fell in love with kids literature, because carats a wonderful place to spend your days. It’s, it’s, it’s some of the most interesting art. And I think that we don’t necessarily find it because most parents just default to classics, or, you know, what they knew is kids or whatever. And there’s just a tremendous amount of brilliant work being done in that space. And I was just like, Ah, this is, this is a space I want to work in, you know, I love this. And I love this. And, you know, the messages are so universal, and some of the work is just so beautiful. It’s it’s an uplifting space to be and it’s a, it’s a wonderful place to build kind of, you know, more aspirational brand.

Kara Goldin 16:32
So for people who are have not received literati, tell us what you’re delivering than. So I know, You’ve described the service using data technology and personalization, to improve literacy outcomes. But talk to me a little bit about, you know, sort of how you’re different from maybe somebody going to a bookstore, for example, to pick up some books. Yeah,

Jessica Ewing 16:57
absolutely. So it’s a great question. And it’s best told through a story actually, of where it started and where it were ended. So, you know, it started with, you know, us just building these different clubs, you know, so so it was very basic, when we first started, it was just like, you know, you could join Club Neo, or club sprout or club Novant, it was all just, it all started out, just age based. And we would send, you know, let’s just say you had a two and a half year old and you would join Club Neo, and we would send you five curated books that you know that we just thought were brilliant for ages zero to three, and you would get to kind of explore those for a week, you know, at home, buy it, buy the ones you want, and send the rest back. And, you know, we’re trying to solve this problem that parents face when buying kids books online, which is just that it’s really hard to predict which books kids will gravitate to, like, it’s hard to predict which books kids will learn, sometimes kids will get obsessed with something and they’ll want to read it, you know, 100 times, and just this is the book that I want to read 100 times and that’s actually important for, for brain development and repetition. And parents are trying to find those favorites. But when you’re shopping, particularly online, you know, it’s difficult and and sometimes taking kids to a bookstore, especially little ones is is challenging. You know, there’s, there’s too many choices. There’s a lot of toys and distractions at most bookstores. And it’s just, it’s not an experience designed for, you know, or optimized for, for kids. I mean, most kids read at night, they read after bath time, read before bed. And so it seemed like a home product, you know, a home delivery product was really the right way to go. So it started out very basic, it was just like all the technology that we were building was all reverse logistics and supply chain technology that was just designed to, you know, take the books back. So you know, send the box out, let people try the books for a week, buy what they want, send the rest back. And so we were building basically an engineering reverse logistics technology to enable that, you know, a choice product for consumers. And that’s where it started to get really interesting. Because at the beginning, you know, we would, we would sit around the room and we would fight over what went in the box. And so you can imagine, like, you know, there’s certain amount of, of, you know, of taste making and you know, that that’s going on here and, and, you know, certain books that you know, that we feel passionate about, like, oh, you know, this is the greatest story or this has the greatest illustrations or this is a book that is a hidden gem that that and we just dug so deep, you know, we dug so deep, we looked at 1000s of books, and if something wasn’t in the top, you know, one out of 1000 it we wouldn’t even consider it right and so, so the service we were providing early on was just finding these hidden gems and we would get notes from customers all the time that we’re just like, you know, I love kids literature I would, you know, we have you know, we’ve got a great bookshelf already but you know, I just would never have found this this this selection you know, with about the service and, and that’s really the value that we’re providing. But where it got really interesting and keep in mind I studied, you know, I studied a certain amount of Computer Science and Artificial Intelligence at Stanford, where it got really interesting was that, you know, the fights that we were having over, what went in the box quickly got resolved when the data would come back. And we would see certain books kept by our customers with like, certain books had a 90% Keep rate, and certain books had, you know, say a 30% Keep rate, you know, and a 30%. Keep rate, you know, meant, you know, I forgot to send back the box, that’s what, that’s what a 30% keyframe meant, but you know, that didn’t mean that we had, and so we were looking at it, we were just like, This is so interesting, we, we kind of inadvertently built an AV testing platform for kids books, because we were, you know, just trying to find out what was good, but our customers were just by their purchasing choices, telling us what was what was landing, and, and what wasn’t. And so, really, where we’ve gotten today, is, you know, taking over, we have, you know, all these data points from having operated over these years. And, and now we’re operating on a much more sophisticated level, where we’re able to say, okay, you know, we know that these, you know, these books are are popular for kids in this age range, but able to take it to a much more sophisticated level, and to let parents actually fill out, you know, a profile where they can, can tell us, you know, okay, this is the level my child’s reading at, these are their interests, these are the types of books they like, these are the types of books they don’t like. And we’re actually able to personalize every single box to every single child where we’re no longer finding, like, here’s the best five books for ages three to five, but here’s the five best books that we believe are going to land for your reader, you know, who’s reading at, at this age range, who’s at this stage, in their intellectual development, who’s you are obsessed with these topics right now. And that’s really, really what gives us an edge because we want to, you know, appeal to kids interests, and also spark new interest. But there’s a fun fact, in the in the world of literacy that I love to bring up, which is that if you give a child a book about a subject that they’re interested in, and kids go through phases, you know, dinosaurs, unicorns, you know, trash trucks, you know, transportation, you know, you see all these phases. But if you can give a child a book about a subject that they’re interested in, they’ll actually read one to two, sometimes three levels higher than the reading level that they’re at, in order to be able to stretch to to access the information, which makes total sense to us as adults, right? Like, we’ll read something that’s hard to read or a little beyond our pay grade, if it’s about a subject matter that we’re absolutely fascinated by. And it can be a great way, I think just spur reading an intellectual development among kids and get them really motivated and excited to be learning with intrinsic motivation, not extrinsic motivation.

Kara Goldin 23:12
I was just having this conversation with my high school age son, because there are certain topics, certain subjects that he is not that psyched about. And there’s others that he’s, you know, totally excelling. And unfortunately, there are things that you actually do have to take in school, especially in high school. So, you know, it’s sort of a challenge, but it’s, he’ll get through it, but it’s, you know, I think it’s along the same topic, or the same type of thing that you’re talking about, I think, Yeah, same wavelength, for sure. So, fundraising, obviously, funding is is something that every founder that I know of is, you know, even if they feel like, it’s easy peasy. It’s, you know, it’s stressful, right? Finding the right yet investors, and especially if you’ve never done it before, that’s a whole other people.

Jessica Ewing 24:13
Yeah, though, I could we could do a whole a whole session on fundraising. And that is, so you know, I’ll just start out by saying that it was not easy for me, not easy at all. And so, easy peasy and fundraising are not two words that that, you know, two expressions that would ever come in the same sentence for me, especially for a category like books. Yeah, you know, yeah,

Kara Goldin 24:35
I can imagine. I mean,

Jessica Ewing 24:36
this is challenging, right?

Kara Goldin 24:38
What advice would you give to other founders that are out there sort of looking for looking for money? I mean, is there any, like things that you wish you would have known?

Jessica Ewing 24:48
Oh, 100%. No, where do I even start? I mean, first of all, you know, I’ll experience share a little bit on what you know that some of the challenges that I faced and some of the darker moments for me, you know, in the process, which was, you know, you know, I started out fundraising and, you know, I didn’t, I didn’t know what it took initially to get funding and I was trying to fundraise, you know, pre revenue with just an idea. And I thought that maybe, you know, my, you know, history building products that Google, you know, or my reputation there as a product leader, you know, would help get me started. And, and I quickly realized that it wasn’t enough, right. And I was getting just stopped left and right. And having worked for a company like Google, it made it easier for me to get some some of the introductions, I got a chance, you know, a seat at the table or whatever, but there were so many things that I didn’t know. No. Other, you know, I mean, I think my first pitch ever was, you know, Sequoia, that was, like, the first pitch I ever gave, and it was just like, I had no idea what I was doing. And, you know, I just didn’t understand any of the dynamics of how venture capital works. So, I would go in there and just guns blazing and be like, you know, this could be like, a $50 million company, and it was just like, you know, like, who cares? You know, what I mean, and it was just like, I just didn’t understand the, the table stakes, I didn’t understand that the dynamics of you’re looking for, you know, to hit a home run to build a billion dollar company to, you know, how VCs view these investments that, you know, many of them will fail, but the ones that succeed need to go big, you know, I didn’t understand that. And so I got stopped out a lot in my early rounds. Because, you know, my idea wasn’t big enough. And it was sort of, like, shocking to me, because I’m such a big idea thinker. But, you know, I needed to go think through, you know, how is this going to get to, you know, not just a $50 million company, but, you know, a billion dollar company, you know, a $5 billion company. And so, you know, that was really the first thing was just like, is this, you know, is this big enough? And I will say that, you know, I was lucky because the all the VCs that said no to me, and there were many said no, to me, respectfully and politely and they left me with some kind of insight or hint or intro or reason why, or something that made me better. Right. And so I would say that my first piece of advice when it comes to fundraising is that sometimes a no can be just as important as a yes. Right? And if, if the investor, if you’re willing to just go a little bit deeper with the investor on why they said, No, that can give you some really critical piece of information about your business, and maybe there’s a hole in it, or weakness, or something that you’re not seeing that can make you stronger. So my first piece of advice is just, you know, pitch anyone that will, you know, take the meeting, but don’t take a no as a waste of time, because you didn’t get the funding, see what the lesson is in it. And you know, and make your pitch stronger. The second piece of advice I would say about fundraising is that know that it’s hard for everybody. I haven’t talked to a founder

that I know, you know, male or female, I mean, very few that are just like, Yeah, this was like a really easy process. And I just, like walked in there. And, and I thought that I thought that it was easy for certain people, you know, and I remember talking to one of my former colleagues at Google about this, and he was kind enough to share with me like, he’s like, Listen, he’s like, I get so many rich, I’m like, you, I’m like, people should be dying to write you a check. You know, you’ve got all the right things, all the right degrees, all the right. And he’s like, no, no, it’s brutal. He’s like, I just, he’s like, if I, you know, I often don’t even get a second meeting, like only one out of 15 times do I even make and I’m just like, he’s describing his stats to me. And I was like, whoa, okay, that’s shocking. And so, you know, he was kind enough to share that with me. And that really gave me like, kind of a shift in perspective, you know, and so I’d say those, you know, it’s, you know, it’s hard for everybody. So I’d say the, you know, the first thing is really, sometimes a no can be just as valuable as Yes. The second thing is that no, that that if you’re getting I wasn’t used to facing that much rejection, candidly, you know, getting getting a door slammed in your face, like 15 times in a row, you can just feel like an absolute utter failure. So I think it’s important for people to just know, the odds that like, you know, that that’s like normal and once you like, normalize for that, you know, you stop taking it so personally, because it is it is normal, you know, and then it’s a you know, beyond that it’s just in the early stages, it is hard because you need you need vision, you need talent, and you need traction. And, and it’s very, very difficult to raise if you don’t have all three Did you raise from angels? I did. Yeah. I raised my first round was from angels and a combination of angels and funds. So about half angels one fund.

Kara Goldin 29:55
That’s great because I think a lot of pre revenue stuff unless you We’re clearly a tech company with a giant idea. It’s, you know, it’s really tough, especially today to walk into a VC pre revenue and say, hey, you know, write me a check. So the one other thing that I’ll say, which, you know, you’ve probably realized, and I certainly realized this when I started hint, and I had the same ease of being able to, you know, I knew people in Silicon Valley and, and was able to get the meetings, and I actually had many people asking me, who was taking care of the children, because they, you know, quickly, research that I had four children, and so they just decided that I couldn’t actually start a company.

Jessica Ewing 30:42
Oh, wow. Okay. Yeah. Amazing. Okay. So I’d walk into a few of these mediums that question,

Kara Goldin 30:49
Oh, yeah. And my husband would come into and actually what was so funny is he would, and they would ask me, and, you know, I’d say, he’s, he’s the father of all four of my kids. And yeah, and they said, Yeah, but he’s here with you. So who’s, who’s watching the kids?

Jessica Ewing 31:09
I mean, yeah, I mean, do you mind if I asked you a question about your experience? Fundraising. Okay, so, so I’ve had this conversation with many women, because it can be when you’re just losing, you know, losing. And believe me, I’ve had I’ve had so many noes. It’s just, it’s, it’s hard, and especially in a category like books like that, you know, it’s just like, wow, I had a lot of, but but on the subject of being a woman raising, you know, specifically that it can be hard to sort of sift out, you know, am I am I, is this, is this a factor? Is this hurting me? You know, and like it like, certainly the questions that you’ve gotten, I’ve spoken to so many female founders about this. And, you know, one thing that comes up is that, you know, in the science or in the literature that oftentimes, in these VC meetings, you know, women or men are asked more about opportunities, and women are questioned more about risks. And I want I wanted to know that you kind of felt that, in your own process that you were being asked more about the risks of like, you know, how are you avoiding these risks, rather than the opportunities of just sort of like, how big can this get?

Kara Goldin 32:15
Yeah, I mean, I think it was, and it wasn’t just one VC. It was multiple, you know, VCs that asked me this question, what I thought, and I’ll answer it sort of in two parts. But what I thought was so interesting, we would walk out of the meeting, and my husband and I would be like, sort of like, okay, here we go again, like, you know, they’re asking me who’s, you know, why aren’t you at home, taking care of the kids? And he would view it, as you know, why do they just think I’m a deadbeat dad, right. Like he was offended that they didn’t, they weren’t.

Jessica Ewing 32:51
He viewed it in a totally different lens. Oh,

Kara Goldin 32:53
yeah. Different lens, but also equally offended. I mean, that that, which I thought was fascinating, on many, many levels, but anyway, but I, but here’s the other thing that I will say, and this is how then this relates to you to what I realized later on. And as I mentioned to you earlier, I, you know, wrote my, my book on dotted, it talks about this in there to that, that the people invest in what they know. And so I walk in with my drink, hint, and I’m talking about my diet soda by diet, Coke addiction, and they’re all nodding their head. Probably none of them drink Diet Coke, because the majority of people who drink Diet Coke are women. There are some men, but they were all men sitting across from me, and I’m pitching them this idea. And a couple times people said, you know, I need to ask my mom, I think my wife drinks Diet Coke. I’m pretty sure she does. And I’m going to ask her, like, how many she drinks a day. And I always tell people, you know what he never did? Right? They just tell you that. Yes. To get you out of the rare, right. And and they’re, they’re, they’re good at sort of being cordial, but they never really do. And at the end of the day, they invest in what they know. And so my question for you is, how many of those people are actually buying books for their children? I don’t know how many they are. But I but I think it’s like maybe they aspire to, but they’re not. And so I think like, they don’t tell you that right when you’re when you’re in so, you know, I call them the doubters right? They’re like oh, you know, there’s this guy up in Seattle he’s you know, he does something like that like they’re not purchasers, right of the Yeah, and so it’s, it’s fascinating because it is

Jessica Ewing 35:04
fascinating. It is fascinating. The worst meeting I ever had was with an angel who just basically ended the call with. And this was this was a friend even this was like someone I knew. And so, you know, was having a friendly conversation. I was like, man, you know, I just keep getting stopped out by these VCs. And, you know, and I don’t know why. And he just goes, he’s like, You should just he just he goes, it’s just because you’re out of your league here. He’s like, You need to just, he just goes like, I’m just, I’m your friend. And I want to level with you. And I want to be honest with you. He’s like, There’s nothing interesting to be done in books. And there’s nothing interesting to be done in music. Those are two dead categories. And you should forget you ever had this idea. And I’m just being your friend, I’m telling you should forget you ever had this idea? You should go home. Otherwise, you’re going to come away from this experience hating books forever. And, you know, the reason why this isn’t this isn’t going for you is you’re just you’re out of your league here. Yeah. And you know, and I just like, it took me, you know, the whole night, probably the whole week to shake off that conversation. Yeah, you know what I mean? Because, because it’s just we take these we’re founders, we know, these problems are real. And we take these rejections So personally, like, because it’s hard, it’s impossible not to it’s impossible to build a company without putting your your heart and soul and mind and body and all the things into it. Those are the table stakes, right? Yeah. And then when you get these rejections, it’s impossible for me anyway, even though I’ve gotten the rejections so many times, to not take them personally. And it’s a sting every single time. And it’s just like, you have to kind of come back and kind of re architect your ego every single time.

Kara Goldin 36:49
No, let’s go. Hi. All right. I, you know, I’m reliving it. I mean, I’ve got so many we could talk, we could have a whole session on you know, fundraising, because it really is, you know, it, everything that you’re saying is true. And I write a lot on LinkedIn, in particular, I do a ton of writing about this. But the you know, it’s, it’s interesting, because we care more about when the message about doubting you comes from friends and comes from family, it hurts, right? They’re trying to be honest with you, and but it hurts, like when it’s somebody that you don’t know, and you’ll never see again, right? Like, they can doubt you and you can brush it off, but it’s much harder. And it and, you know, you have to find a way to just move forward more than anything else, and fine. And you know, the last thing I’ll say people always ask me, it was harder to raise money as a woman. And I’ve, I sort of famously said this at a fortune conference on stage a few years ago, and I said, doesn’t matter. And you know, who I think Patti Sellars was interviewing me. And I said it, she said, yeah, it does matter. And I said, well, but the point is, I want to build my company. So does it really matter? If it was harder? I mean, you know, are they profiling me in some way to say, like, Oh, she’s got four kids at home, she, I mean, how she can have time to do this, like, you know, all of these things, or, you know, she had a Diet Coke addiction, like, you know, that, you know, like, it’s just whatever they’re saying, you know, maybe they don’t want to invest in women. Right? May you never really know what the story is. But does it matter?

Jessica Ewing 38:41
Right, yeah, exactly. I mean, I think that like that, you know, I eventually got to the same place where I was like, alright, you know, I can’t boil the ocean here. I just, I want to move forward, you know, I can’t boil the ocean, I want to move forward. And I was like, 100%, is it true? I sort of arrived at the same place? I’m like, is it harder? You know, probably, but are there women getting funded? Yes. Okay, well, then I need to figure out how to go be one of them. Right, you know, to move forward, like, right, and if there wasn’t an example of a single woman, you know, getting funding, but there were there there are, you know, and so the question is, is it harder? You know, I agree with you, it’s just sort of, probably yes. But, you know, if you want to build a company, and you want to build a venture backed company, which by the way, like, you know, I don’t think that’s the only way to start coding, obviously, there’s different you know, ways of funding you know, coming and that opens up this whole can of worms and you know, and pressures and, and all these other things that it’s not for everybody, right? And so, but if you want to go that route, and you want to take that swing and you want to live that life and you’re willing to commit, you know, the seven to 10 years, or whenever you’re it’s a one way door, you know, once you take that that first check, you know, you’re you’re, you know you’re in it, well, I

Kara Goldin 39:57
love, love, love what you’re doing Seeing and if there are any investors out there that are as interested as, as I am in what Jessica is doing. I mean, definitely, it’s a great product. I should preface this by saying I am not an investor, but I’m a huge fan of what she’s doing. And she’s done a terrific job of building a great company. Definitely we will put this in the show notes all about where to sign up for literati, and also follow Jessica a little bit more, but I really appreciate your time, Jessica, for sure. Thanks, Kara. Thanks all for listening to this episode. We hope you enjoyed it. And I want to thank all of our guests and our sponsors. And finally, our listeners. Keep the great comments coming in. And one final plug if you have not read or listened to my book undaunted, please do so you will hear all about my journey, including founding, scaling and building the company that I founded. Hint we are here every Monday, Wednesday and Friday. Thanks everyone for listening, and goodbye for now. Before we sign off, I want to talk to you about fear. People like to talk about fearless leaders. But achieving big goals isn’t about fearlessness. Successful leaders recognize their fears and decide to deal with them head on in order to move forward. This is where my new book undaunted comes in. This book is designed for anyone who wants to succeed in the face of fear, overcome doubts and live a little undaunted. Order your copy today at undaunted, the and learn how to look your doubts and doubters in the eye and achieve your dreams. For a limited time. You’ll also receive a free case of hint water. Do you have a question for me or want to nominate an innovator to spotlight send me a tweet at Kara Goldin and let me know. And if you liked what you heard, please leave me a review on Apple podcasts. You can also follow along with me on Facebook, Instagram, Twitter and LinkedIn at Kara Goldin. Thanks for listening