How Ollie AI Is Using AI to Solve the Mental Load

Speaker 1: Welcome to She Built It. I'm your host, Melanie Bar. 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 Ali.ai, a personal AI assistant for families. Christy, thank you for being here.

Speaker 2: Thanks so much for having me, Melanie. I'm excited to chat.

Speaker 1: What is the moment or frustration that made you certain that Ali AI needed to exist?

Speaker 2: This goes back a few years. I am a mom of four kids. I have a 15year-old son. I have 11-year-old twins and a 9-year-old. And my my youngest are three girls and they were born really close in age. When my 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 my organization and had a really demanding career and then had busy, you know, life at home with my 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 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 elementary school at the time. And I remember early on I took my 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 like 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 this is like 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, right? I was mortified. And so I thought, "No, no worries. I have a few extra minutes this morning. I'm going to go run and grab a snack and I'll bring it right back." 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 I was fine. and I broke my wrist, but it was could have been way worse and my daughter was totally fine. Thank God for car seats. It really that moment was a wakeup call for me to 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 Ali today. But that was the moment where I realized this is a problem and I started to understand it better and realize 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

Speaker 1: because we're juggling kids schedules and our own schedules and work schedules and 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 this is a problem. So that was that was the moment where I was like we got to figure this out for myself and everyone else.

Speaker 2: Yes. It's such a mental load on parents and on moms. And I'm a twin mom. I can only imagine having three at that age. And I I also know the feeling of wanting to work, wanting to continue to work and wanting to also be a good mom and a good parent and there for your kids. It's true. There's you get you have these sort of 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 and with all of those desires are all these little decisions

Speaker 1: you have to make in your day. And yeah, there's there's a significant mental load behind all of that. And you know what we're trying to do with Olly is is help take some of that off your own mind so you can free up some of that mental space for other things like, you know, being present for your kids or spending time to do whatever it is that you love to do.

Speaker 2: Yes. And there's also keeping up with the schedule for four. I I can only imagine what that schedule's like. And also wanting to make a good life for your kids and making sure that they're happy and the family's happy and, you know, make space for joy.

Speaker 1: Yeah, the scheduling is real. You know, 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. You've got there's a lot of coordination that happens and my husband and I were doing a lot of this coordination ourselves just, you know, checking in at night in the morning like what's on your calendar, what's on your calendar, don't forget this, don't forget that. Today, we have Olly doing that for us. So, we have Ali 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, keeps us both accountable, too.

Speaker 2: And does it integrate with other apps for for sports and other other activities?

Speaker 1: We are working on that. So, right now, Ali connects to email and calendar, whether it's Google, Apple, Outlook, whatever, and pulls in all of that information. It also can connect to WhatsApp. So if you have school community chats in WhatsApp, it can it can summarize that information and let you have actions you need to take from

Speaker 2: 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 that you just see what's important. And it's

Speaker 1: great that you connect with WhatsApp because I'm on a lot of the sports [laughter] 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. Yeah. No, we don't want we don't want to drop the ball. That's not No one no one wants to do that. We want to be able to to to provide all the things, but it is a lot of work to to check all that stuff and to stay on top of it. What is the part about building Olly that you could talk about all day? The part that lights you up?

Speaker 2: It's the families. Talking to people like you about your family and and understanding what what you've got going on in your day-to-day. Um we from the very beginning of Ali Ali's been around for about three years now. We made it a priority to stay really 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 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 Ali to help file ideas that they had in their head and they at the time we didn't have Ali wasn't connected to your Google Drive. So they were asking Ali 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 and manage all of that for them. But it was such an interesting conversation to 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 as a founder and you know deep in the weeds of marketing Ali and trying to figure out how do we grow this? I'm constantly secondguessing is this the right thing? Am I doing the right thing? Is this the the real pain point that they're struggling with? And being able to talk to these families and and talking to parents really helps validate or disprove the thing I'm thinking and it it helps me make decision a lot faster. And that's just so invaluable.

Speaker 1: It's really interesting that you say Google Docs because I type I type out and this is so antiquated, but I type out the schedule and I print it out and I put it on our kids' doors because they're 12. I mean, they can check, they have phones and 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 what's going to happen. You know, personalities are different. And so then if they're if they don't know what's happening or what time their practice is or where their practice is, they can just look at it on their door. So, it's interesting to think about that pulling into a Google doc. Like at a certain point, they're going to 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 2: That's really cool that you I like that you have it like visually there for [laughter] them. I had to 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. Well, I imagine you probably create that that doc. You pro do you pull calendar

Speaker 1: information there? Yeah. Yeah. every something that Ollie could help with in doing that for you and create that routine for you. So then you just hit print.

Speaker 2: Exactly. When you mentioned Google Docs, I thought, "Oh, that's interesting because 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. How are you using AI inside Ali and where do you see the biggest opportunity?

Speaker 1: Well, we're AI native. So everything we do is with AI. Of course, Ali, the product is completely built with AI. We even go so far as if a user is using Ali and something isn't working, Ali as an agent will file a ticket, a bug for us. The user doesn't have to do that. Ali 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 customuilt. We build our our marketing website through AI and where I think the opportunity really is understanding where to leverage the strengths of AI and where to leverage your own strengths. AI is really fantastic at understanding the context that it has. 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 Ali 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. the opportunity is is leveraging that that to then inspire originality and creativity. And for Ali, 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 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 you can use with AI.

Speaker 2: Yeah. And it's so important to build that brand from the foundation and around in real life and use AI as the tool.

Speaker 1: Yeah, I agree. We're building something that touches people in a in a very personal way and we want the brand to feel very personable and relatable and that takes work and takes creativity and takes iteration. It's it's not something that we're going to get right away. We've got to evolve it and we're

Speaker 2: continuing to work on that. What is your biggest growth challenge right now and how are you thinking through solving it?

Speaker 1: Ali 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 sort of break through and show that Ali 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 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 really focused on building a product and a brand that you can feel safe with and and and is reliable. communicating that in a way that sort of breaks through is something that we're still working on and still figuring out as we grow. Ali, we're 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 2: And 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 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 stomach ache, was like, "Can you pick me up at 12:15?" Then at 3:00 a.m. my son couldn't sleep. And then I wake up ready for the day of meetings. So to go into my work world. So when you say busy families, you know, you'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 1: Yeah, it's true. 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 the benefits of it, we start to sort of connect those dots. And hopefully we'll will help kind of connect those dots and make it so 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 and try something when you're when you're running between pickups and and juggling work and home and cooking dinner and you know all of those things. I I totally get that. Yeah. Yeah. So, we're we're trying to make it as as easy as we possibly can and and that's a big reason why we put Ollie in text message because we we didn't want to give you another app that you're going to have to figure out how to use. We wanted it to be as seamless and using the the tools you already use.

Speaker 2: Yeah. and we're always on text all day anyway. Yeah. Right. [laughter] [gasps] What has changed the most in your leadership as Ali AI has scaled and what has that evolution asked of you personally?

Speaker 1: It's been a journey building Ali. So, we've been around for about three years and we've had this mission to take on the mental load through AI and and really help con families in their day-to-day lives, but we've we've had to go about it a couple different ways to find the right solution. And so for me personally, it's been a couple different things that I've really learned and I I'm still learning every day as as we do this. 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 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 and test and and keep a really open growth mindset and figure out, okay, this thing that we've been working on for a year is not really working. We're going to have to pivot and we're going to have to try something totally new and different and see if that works. And that's something I'm still kind of 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 going to 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 tooting my own horn or or sort of talking about the things that we've done, but I've realized as the only marketer in a in a tech startup, 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 put yourself out there and put that information out there. Even if it's not a huge success, share the things that you're doing and working hard on to show that progress. If it doesn't succeed, share that learning. That's something that I'm I'm continuing to work on, too, is how do we recognizing and and and acknowledging the work that we're doing as we're moving along this path.

Speaker 2: Yeah. And I don't know about you, but as a twin mom, I got really good at an or trying to anticipate what could go wrong. [laughter]

Speaker 1: Totally. almost to the point where my

Speaker 2: husband's like, "Why are you talking about what could go wrong?" I'm like, "Because I don't want it to go wrong cuz, 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 in a way that sets you up for dealing with the unknown."

Speaker 1: But it also makes you well, it's made me someone who thinks through what could go wrong. So, good for you for, you know, things change so fast, you know, because you can run from it or you could run towards it. And good for you for running towards it as it relates to Ali AI.

Speaker 2: Oh, well, thank you. It is it is tough and totally I still have nightmares of the two babies going in two different directions. [laughter] I know I had someone say, "How do you deal with that?" I'm like, "Well, it wasn't easy. [laughter] You just figure it out."

Speaker 1: You are building fast and backed by investors with a growing team. How do you protect a strong company culture through all of that? This is something

Speaker 2: also that we keep working on and I think we have to kind of keep revisiting as we grow and evolve. There are a couple little things that we do on a daily basis and I feel like for family life, this is true for work. Having rituals and being together really helps. So, we're we're a fully remote team. Although my co-founder Bill and I work together periodically in a co-working 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 rebuild those relationships even though we talk to each other dozens of times a day being in person is is different. And so that's that's really important. And the other one that we do is kind of a silly thing, but we have a couple little rituals that we do as a company every day. whether it's a good day or a bad day, we have a a daily standup 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 standup, we all kind of countdown and clap together and that's like starts the day. And it's kind of a funny silly little thing, but you know what? No matter like what the day is, we're always going to do that. We're always going to 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 like I'm wearing a mustache one day and Bill's wearing a a ponytail and like it's hilarious and it just diffuses everything and makes Fridays a little bit lighter and a little bit more fun. Keeps us smiling.

Speaker 1: I 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 2: Yeah, it does. You know, it kind of energizes you right at the end of the conversation ready to to move on to the next thing. Yeah, I love that. What is

Speaker 1: one honest lesson about co-founding a company and leading people that you wish more founders talked about? Fortunately,

Speaker 2: there's been so much of this idea of like building in public that I think there's been more transparency recently than there has in the past. We could all talk more about is that you are always selling. you just always have to be there's this idea of like building a a really excellent product that is just taking off just does not work anymore because we're in such a competitive environment we're in it's a very noisy marketplace with lots of content and lots of products and and lots of choices and so you really have to just kind of always be out there and promoting your your product your your the thing you're doing and that's that's hard and I think we probably could all talk a a little bit more about how to do that and how to make it successful. And you know, it's something we're we're certainly still still working on.

Speaker 1: It'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 2: Yeah. Yeah. It's true. It's so true. 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 like fight through that and and and put yourself

Speaker 1: and put the company out there. What is one way that you protect and celebrate your joy as you go through your work day in life?

Speaker 2: My joy comes from my family. So that's that's what's so important to me. And so I really try to protect that time with them. Keep my my evenings to myself and my my weekends as much as I can and and compartmentalize my my work days and my my family time. Outside of that, I do try to keep a routine of trying to like work out in the mornings or go for a walk in the evenings just to have a little bit of 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 and disconnect a little bit and it clears my head. Yeah, it's

Speaker 1: 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 you know take that time in the morning to make sure you get your workout in.

Speaker 2: So important. So important. Yeah, it it totally is.

Speaker 1: Thank you so much for joining us today and for helping make families live better lives with Ali AI. Can you please share with us how and where we can find you?

Speaker 2: Oh, thank you. Thanks so much for having me. You can find Ali at ali.ai and you

Speaker 1: can connect with me on LinkedIn. I'd love to connect and hear from you.