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She Built It® Podcast
Welcome to the She Built It® podcast. Join me as I talk to women who have successfully built it - a life and business that they love. We dive into the topic of “how” they built it and talk about everything from having the courage to make career leaps to the details of how to lead effectively, build teams, implement growth strategies, and infuse tech innovation. Magic happens when we focus on the part of ourselves and our business that brings us joy so let’s dive in.
She Built It® Podcast
How Ollie AI Is Using AI to Solve the Mental Load
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On She Built It®, Christy Shannon, co-founder, CMO, and mother of four, opens with a stat that should stop every busy parent in their tracks: 41% of parents say that most days they are so stressed they cannot function. That’s not a personal failing; that’s a U.S. Surgeon General warning.
Christy asks a question that’s harder to answer than it sounds: if you use AI every day to make your work life easier, why hasn’t anyone brought that same logic home? She built Ollie AI to do exactly that: a Family AI that lives in your text messages, connects to your email, calendar, and WhatsApp, and sends a shared morning rundown to you and your partner so neither of you has to hold the entire schedule in your head. She also gets honest about what it actually feels like to build something completely new in a rapidly changing space: the pivots that feel like failure but aren’t, the discomfort of self-promotion, and the truth most founders still won’t say out loud: great products don’t just rise on their own.
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You have these personal desires that sometimes compete with each other and you've got to kind of figure out how you can make it all work and with all these little decisions you have to make in your day. There's a significant mental load behind all of that. What we're trying to do with Ollie is help take some of that off your own mind so you can free up some of that mental space for other things being present for your kids.
SPEAKER_00I'm Melanie Farr. Welcome back to the Cheeblet Podcast, your go-to place to empower you to live the life and business that you create. I'm here to talk about everything from having the courage to make life and career leads to the details of how to lead effectively, create successful teams, implement strategies for growth, and infuse tech innovation. I'm here to celebrate your wins and navigate through your challenges. I live in the city now, but I grew up in a town of a thousand people. I've navigated major life leads, a senior-level corporate career, worked in professional sports, and now as a successful entrepreneur who loves business, technology, family, and making meaningful connections with you and the She Built It community. I also love a good workout and dose of self-care. Magic happens when we focus on the part of ourselves and our business that brings us joy. So turn up the audio, open your favorite notes app, grab your favorite drink, and here we go. Welcome to She Built It. I'm your host, Melanie Barr. The mental load is not only a family problem, it is also a leadership, productivity, and technology problem. Today's guest is building AI to address it. Christy Shannon is the co-founder and CMO of OLI.ai, a personal AI assistant for families. Christy, thank you for being here. Thanks so much for having me, Melanie. I'm excited to chat. What is the moment or frustration that made you certain that OLIAI needed to exist?
SPEAKER_01This goes back a few years. I am a mom of four kids. I have a 15-year-old son, I have 11-year-old twins, and a nine-year-old. And my youngest are three girls, and they were born really close in age. When my twins were born, I actually, on my maternity leave, got promoted into a new role. I took on even a bigger job in my organization and had a really demanding career and then had busy life at home with my son and my baby twins at the time. And then I found out I was pregnant with my fourth not long after. They were about 15, 16 months apart. And I decided at that point I needed to take some time off. I wanted to be home with the kids and juggling both was too much for me. So I took some time off. I spent about a year or so at home with the kids. And then I wanted to sort of stair step my way back into my career. So I took on a part-time consulting role. My twins went into preschool. And my youngest, I found a babysitter to help while I was working. And my older son was in elementary school at the time. And I remember early on, I took my twins to preschool. I went to go drop them off. And I get to preschool, and the preschool teacher looks at me and says, Did you bring snack today? And I looked at her with a blank stare in my face. I'm like, oh my God. I had no idea I was supposed to bring snack today. This is not even on my radar. And I'm very much a type A person. I do not like to drop balls. I don't like to forget things. I have spreadsheets and notes and all kinds of stuff. I was mortified. And so I thought, no worries. I have a few extra minutes this morning. I'm going to go grab a snack and I'll bring it right back. So I put my youngest in the car with me. We run over to the grocery store. And in my frenzy, I run a red light and I crash into another car. And fortunately, I was fine. I broke my wrist, but it was could have been way worse. And my daughter was totally fine. Thank God for car seats. And that moment was a wake-up call for me to realize that all these little things that seem like little things that don't seem like they're that important add up. And that it adds up to a point where you can't take it anymore. And for me, that was that moment. This was a few years ahead of where we are with Ollie today, but that was the moment where I realized this is a problem. And I started to understand it better and realized that I needed a solution. And I wasn't the only one that needed the solution. But in fact, this impacts everyone. Families feel this the most because we're juggling kids' schedules and our own schedules and work schedules. Parents are overloaded by it. The US Surgeon General just last year issued a warning saying that 41% of parents most days say that they're so stressed they cannot function. And this is a problem. So that was the moment where I was like, we got to figure this out for myself and everyone else. Yes, it's such a mental load on parents and on moms.
SPEAKER_00And I'm a twin mom. I can only imagine having three at that age. And I also know the feeling of wanting to work, wanting to also be a good mom and a good parent, and they're for your kids.
SPEAKER_01Yeah. You have these personal desires that sometimes compete with each other, and you've got to kind of figure out how you can make it all work. And with all those desires, are all these little decisions you have to make in your day. There's a significant mental load behind all of that. What we're trying to do with Ollie is help take some of that off your own mind just so you can free up some of that mental space for other things, being present for your kids or spending time to do whatever it is that you love to do.
SPEAKER_00Yes. And there's also keeping up with the schedule for four, I can only imagine what that schedule is and also wanting to make a good life for your kids and making sure that they're happy and the family's happy and make space for joy.
SPEAKER_01Yeah. The scheduling is real. We've got four kids. You've got apps coming at you from all different directions. You've got emails from teachers, you've got PTA emails, a lot of coordination that happens. And my husband and I were doing a lot of this coordination ourselves. And today we have Ollie doing that for us. So we have Ollie is an assistant that connects to your email and calendar, and it lives in your text messages. And so it pulls all that information for you in a text message and it'll tell you. It sends me a rundown every morning of what we've got in our calendar and it does it in a group chat with me and my husband. So we both know from the start of the day, okay, here's what's going on. It helps identify conflicts that we might have. It helps us sort out things that are on our to-do list or reminders and just keeps us both accountable too. And does it integrate with other apps for sports and other activities? We are working on that. So right now, Ollie connects to email and calendar, whether it's Google, Apple, Outlook, whatever, and pulls in all of that information. And it also can connect to WhatsApp. So if you have some community chats in WhatsApp, it can summarize that information and let you know if you have actions you need to take from there or things that you should pay attention to. And our vision is to do all of that, to bring in the information from sports apps and from other teacher apps and all of those other sources of information that you get to consolidate it and bring it to you so that you don't have to go check all those things.
SPEAKER_00And it's great that you connect with WhatsApp because I'm on a lot of the sports chats for bringing snack bags. And you mentioned those snacks. And it's important because you're on the list and you're next to bring the soccer tent or to do something. And then you get there and there's no tent. We had a two-hour away tournament. So it's really important to have that those reminders.
SPEAKER_01Yeah. And we don't want to drop the ball. That's not no one wants to do that. We want to be able to provide all the things, but it is a lot of work to check all that stuff and to stay on top of it.
SPEAKER_00What is the part about building OLI that you could talk about all day? The parts that light you up?
SPEAKER_01It's the families, talking to people like you about your family and understanding what you've got going on in your day-to-day. We, from the very beginning of OLI, OLLI's been around for about three years now. We made it a priority to stay really close to the people who are using our products. And so we are consistently meeting with them, talking to them, trying to understand how are you using it, how is it helping you or not helping you? Tell us about your family life, your day-to-day life. And that's my favorite thing. It's interesting because sometimes I'll talk to them and it's an aha moment of they're trying to use the product in a way. I was talking with someone who was using Ollie to help file ideas that they had in their head. And they were that the time we didn't have Ollie wasn't connected to your Google Drive. So they were asking Ollie to create email drafts to organize all of these ideas. And that led us to the integration with Google Drive. So now they can create docs for them and manage all of that for them. But it was such an interesting conversation to hear about somebody using the product in a way that we had never even imagined. Other times it's really validating to talk to people, you know, as a founder and deep in the weeds of marketing Ollie and trying to figure out how do we grow this. I'm constantly second-guessing. Is this the right thing? Am I doing the right thing? Is this the real pain point that they're struggling with? And being able to talk to these families, talking to parents really helps validate or disprove the thing I'm thinking, helps me make decisions a lot faster. And that's just so invaluable.
SPEAKER_00It's really interesting that you say Google Docs because I type out the schedule and I print it out and I put it on our kids' doors because they're 12. They can check their phones. They're not always great about that. But if it's on their door for the week, also my daughter rolls with anything. My son wants to know it's gonna happen. You know, personalities are different. At a certain point, they're gonna check their phones and that'll be it. But at this age, they want to see it visually. And sometimes it's easier for me to just look at it in one place and wrap my mind around the sports schedule for the week instead of checking all the different apps.
SPEAKER_01Yeah, definitely. I like that you have it like visually there for them.
SPEAKER_00It's a great idea. Like, I need to wrap my mind around where I need to be in the afternoon or what pickups or drop-offs or things I need to do so that I can integrate my work within it.
SPEAKER_01I imagine you probably create that doc. Do you cut you pull the calendar information there? Yeah. Yeah. So that's something that Ollie could help in doing that for you and create that routine for you. So then you just hit print.
SPEAKER_00Exactly. When you mentioned Google Docs, I thought, oh, that's interesting. That's a bit like what I do today. And I know it feels antiquated every time I do it because I use AI and I'm on apps. And I, but having that visualization for this age is really helpful. Yeah, I believe that. How are you using AI inside OLI and where do you see the biggest opportunity?
SPEAKER_01We're AI native. So everything we do is with AI. Of course, OLI, the product is completely built with AI. We even go so far as if a user is using OLI and something isn't working, Oli as an agent will file a ticket, a bug for us. So the user doesn't have to do that. OLI will do it for them. It'll help manage billing and any sort of administrative stuff is all done through AI. All of our analytics are done through AI that we've, our team has custom built. We build our marketing website through AI. I think the opportunity is understanding where to leverage the strengths of AI and where to leverage your own strengths. And so for us, AI is really fantastic at understanding the context that it has. And that context could be something like the history of the information that's on the internet, or it could be the context of a website that you're sharing or a document that you're sharing. Or in the case of Ollie, it's the context of what's on your calendar and email and the history of your conversation. And so it's really great at helping parse through that information, where I think the opportunity is leveraging that to then inspire originality and creativity. And for Ollie, for us, we'll use AI to build our website, but we have a phenomenal brand designer who designed the website and designs the brand. And that's all original thinking and intuition and knowledge that we've gained by talking to families and understanding what this brand is that we really want to create. And then we'll use the strength of AI and its coding knowledge to be able to just create the site that we've envisioned. And so I think that mix is really the power that can you you can use with AI.
SPEAKER_00Yeah. And it's so important to build that brand from the foundation and around in real life and use AI as the tool.
SPEAKER_01Yeah, I agree. We're building something that touches people in a very personal way. And we want the brand to feel very personable and relatable. And that I think takes work and takes creativity and takes iteration. It's not something that we're gonna get from uh right away. We've got to evolve it and we're continuing to work on that.
SPEAKER_00What is your biggest growth challenge right now? And how are you thinking through solving it?
SPEAKER_01So OLI is a brand new category in a brand new space that's changing so, so rapidly. And we're speaking to families that are extremely busy. And so we need to break through and show that OLI is a tool that can help them in their lives and is something that they can trust. There's a lot of question and skepticism around AI. And I think a lot of that is a really healthy conversation. Our goal is to be the most trusted family assistant available. And we know that that's a big responsibility that we're taking on because we're dealing with your family's information. And so we are focused on building a product and a brand that you can feel safe with and is reliable. And communicating that in a way that sort of breaks through is something that we're still working on and still figuring out. And so as we grow, Ollie, we're trying to just get it in as many places and tell the story and encourage people to try it and hopefully share it.
SPEAKER_00And when you say families who are really busy, when you think about adding AI to our work life and making our work easier, why wouldn't we make our family life easier? And as you say this, I'm thinking about how yesterday I went to a baseball tournament game for my son. Then I don't always take my husband to the airport, but he had a red eye and I was awake and I knew I could get in and out quickly. And so I said, I'll take you to the airport. Then my daughter did a sleepover, ended up having a stomachache, was like, Can you pick me up at 1215? Then at 3 a.m., my son couldn't sleep. And then I wake up ready for the day of meetings. So and to go into my work world. So when you say busy families, we're using AI to help our work. Why not use it to help run our lives from the family perspective? Because it's just as busy.
SPEAKER_01Yeah, it's true. It is such, it is just as busy. And I think that's a great way of putting it. I hope that as we all use AI more and more, the benefits of it, we start to connect those dots. And hopefully we'll help connect those dots and make it so much more beneficial to use AI in your day-to-day life. But I understand that it can be hard to change habits and try something when you're running between pickups and juggling work and home and cooking dinner and you know, all of those things. Totally get that. Yeah. So we're we're trying to make it as easy as we possibly can. And that's a big reason why we put OLI in text message. We didn't want to give you another app that you're gonna have to figure out how to use. We wanted it to be as seamless and you know, using the the tools you already use.
SPEAKER_00Yeah. And we're always on text all day anyway. Yeah, right. What has changed the most in your leadership as Ollie AI has scaled? And what has that evolution asked of you personally?
SPEAKER_01It's been a journey building, OLI. So we've been around for about three years and we've had this mission to take on the mental load through AI and really help families in their day-to-day lives, but we've had to go about it a couple different ways to find the right solution. And for me personally, it's been a couple different things that I've really learned. One is that we're doing something new and we don't know. We just don't know. And that's hard for me. I want to help. I want to share my experience. I want to help find the solution. And sometimes we just don't know. We've got to kind of iterate through it and test and keep a really open, gross mindset and figure out okay, this thing that we've been working on for a year is like not really working. We're gonna have to pivot and we're gonna have to try something totally new and different and see if that works. And that's something I'm still flexing that muscle and building it and trying to figure out how to do that more and more because it is, I think as AI accelerates and this world keeps changing, like we're gonna have to do more and more of that. And so that's been a big piece of it. The other part is something that I don't love doing, which is like tooting my own horn or talking about the things that we've done. But I've realized as the only marketer in a tech startup, and this anyone in the startup you're wearing many hats, if you don't tell people the things you're doing, and if you don't celebrate those, no one knows. And so you really have to kind of put yourself out there and put that information out there. And even if it's not a huge success, share the things that you're doing and working hard on to show that progress. And and then if we don't, if it doesn't succeed, share that that learning. And so that's something that I'm continuing to work on too is how do I keep recognizing and acknowledging the work that we're doing as we're moving along this path.
SPEAKER_00Yeah. And I don't know about you, but as a twin mom, I got really good at trying to anticipate what could go wrong. It's totally almost to the point where my husband's like, why are you talking about what could go wrong? I'm like, because I don't want it to go wrong. Because you know, you have all, you know, life can be pretty predictable. And then you have two babies that could go in two different directions and do something that you don't know. So I think in a way that sets you up for dealing with the unknown, but it also made me someone who thinks through what could go wrong. So good for you, Bork, because things change so fast because you could run from it or you could run towards it. And good for you for running towards it as it relates to Ollie AI. Oh, well, thank you.
SPEAKER_01It is, it is tough and totally. I still have nightmares of the two babies going in two different directions.
SPEAKER_00I know. I thought some would say, how do you deal with that? I'm like, it wasn't easy. You just figure it out.
unknownYeah.
SPEAKER_00Yeah, you are building fast and backed by investors with a growing team. How do you protect a strong company culture through all of that?
SPEAKER_01This is something also that we keep working on, and I think we have to keep revisiting as we grow and evolve. There are a couple little things that we do on a daily basis. And I feel like just like for family life, this is true for work, having rituals and being together really helps. So we're a fully remote team, although my co-founder Bill and I work together periodically in a coworking space. We do try to get the team together at least quarterly, physically together, so that we spend that time together. And that that always helps. It helps just rebuild those relationships, even though we talk to each other dozens of times a day. Being in person is different. And so that's really important. And the other one that we do is a silly thing, but we have a couple little rituals that we do as a company that we do every day, uh, whether it's a good day or a bad day. We have a daily stand-up in the morning. And every morning, so we were like rooted in that daily stand-up. That's how we start our day. And at the end of the stand-up, we all kind of count down and clap together. And that starts the day. And it's a funny, silly little thing, but you know what? No matter like what the day is, we're always gonna do that. We're always gonna come back to that ritual. And then on Fridays, we have we call it Filter Friday. And so we're on Google Meets and we put on silly filters and we all wear funny hats, or I'm wearing a mustache one day, and Bill's wearing a ponytail, and it's hilarious. And it just diffuses everything and makes Fridays a little bit lighter and a little bit more fun and keeps us smiling.
SPEAKER_00I love that. And that's so fun to do on a Friday, and it just breaks up the day. And I'm sure the clap kind of sets the tone for the day and the week in in some way.
SPEAKER_01Yeah, it does. It energizes you right at the end of the conversation, ready to move on to the next thing. Yeah, I love that.
SPEAKER_00What is one honest lesson about co-founding a company and leading people that you wish more founders talked about?
SPEAKER_01Fortunately, there's been so much of this idea of building in public that I think there's been more transparency recently than there has in the past. I I would say that the thing that you probably we could all talk more about is that you are always selling. You just always have to be. There's this idea of building a really excellent product that is just taking off, just does not work anymore because we're in such a competitive environment. It's a very noisy marketplace, lots of content and lots of products and lots of choices. And so you really have to just always be out there and promoting your product, your, your, the thing you're doing. That's hard. And I think we probably could all talk a little bit more about how to do that and how to make it successful. And it's something we're certainly still working on.
SPEAKER_00It's really interesting you say that because I just recently went back to different sales tools because we know all of these things, but it's great to have those reminders, especially because we get so passionate over what we're building that we forget those things at times along the way.
SPEAKER_01Yeah. For me at least, I always had this hope that great things will always rise through. And unfortunately, the truth of entrepreneurial business is that's not true. And there are so many wonderful businesses that probably ended up on the cutting room floor that shouldn't have. And so you really have to kind of fight through that, put yourself and put the company out there.
SPEAKER_00What is one way that you protect and celebrate your joy as you go through your work day and life?
SPEAKER_01My my joy comes from my family. So that's what's so important to me. And so I really try to protect that time with them, keep my evenings to myself and my weekends as much as I can and compartmentalize my work days and my family time. Outside of that, I do try to keep routine of trying to work out in the mornings or go for walk in the evenings, just to have a little bit of like physical mental clarity. I find that really helps me, especially when I'm sitting in front of a screen all day, to be able to walk away and get outside and disconnect a little bit. And it clears my head.
SPEAKER_00Yeah, it's interesting when you say compartmentalize. I do the same thing. It's like I have a 45-minute show and that's my time to celebrate or take that time in the morning to make sure you get your work out in. So important. Yeah, it totally is. Thank you so much for joining us today and for helping make families live better lives with Ollie AI. Can you please share with us how and where we can find you? Thank you.
SPEAKER_01Thanks so much for having me. You can find Ollie at Ollie.ai and you can connect with me on LinkedIn. I'd love to connect and hear from you.
SPEAKER_00Thank you for joining us today. I'd love to hear from you. Reach out to me at hello at sheltit.com on our SheBiltit website or at she built it on social. Thank you to my editor, Rich Trafalino, who always makes us sound good. Until next time, let nothing stop you from experiencing effectively business that you crave.