From Flying Special Ops Helicopters To Building An AI Startup I Ep 11. Lindsey Chrismon

My guest today spent over five years as a combat helicopter pilot in one of Army's most elite special operations unit. She flew helicopters on high stakes mission and then she traded the cockpit for a Harvard MBA and a startup. In October 2023, in the middle of her degree, she founded Opley, an AI powered home assistant which predicts and automates home maintenance. She was also named in Inc.'s 500 female founders, Lindsay Chrisman.

Welcome to Women Lead AI. [music] So thank you so much for coming on women lead AI podcast and I would love to know first of all where did you get idea for the uh your for your company Alley? Yeah first off thank you so much for having me this is this is really cool to be uh on women led AI. Um, so where the the concept for Opley started, um, I was actually serving in the military. Um, I was in the United States Army and my husband who had just recently got out of the army started his first business.

Um, and it was in residential restoration. So, water, fire, mold remediation inside of residential properties. If you ever had like say a dryer fire or a water heater that exploded or you had mold that was found like all of those different types of things, his company restored it. And around 50% of the time he was going in these homes and recognizing that these these horrible things that were happening to homeowners could have been prevented if the homeowner just knew what to do and when to do it. And so we started to think um I I I had transitioned out of the military at the time.

and I was up at Harvard Business School and we kind of just like were thinking through this this problem that we were seeing. Wait, why don't homes come with operating manuals just like our our cars, right? They have a dashboard and it immediately tells you when it's time to get your oil changed or, you know, your check engine light comes on, but your home, your most valuable asset leaves you out to dry. And so, uh, we just started to recognize through seeing these problems inside of all of these homes, these homeowners spending so much money and having to deal with insurance companies and just an absolute nightmare of an experience. And we wanted to help homeowners.

How come we are living in this world where, you know, we have Uber and Airbnb and Instacart and everything else is so streamlined and so easy, but taking care of our homes is still such a fragmented, antiquated process. So that is kind of where the the concept for it all started and just really ran through all of like Harvard has an innovations lab and just kind of like brought this problem set to the innovations lab and just kind of worked on it with mentors and all the resources and that's really where Opley was born. This is uh so interesting because when you uh when you explain it like that uh you know any product that I buy comes with instruction manual but uh the house uh doesn't. So uh I love the fact that uh you know you're solving this uh problem. So, uh, let's say that, uh, I'm a homeowner.

Walk me through what happens once I, uh, get onto your, uh, app and how does it work from, uh, what are the benefits and how am I going to use it? Yeah. So, what I would encourage everyone first off, right off the bat, if you're in the US, go and download OPI, OPY, and as a homeowner and and see for yourself. I I will 100% be able to talk through everything that you experience and you know the value um that homeowners are are gaining from using Opley, but but definitely go try it out. Right now it's free.

We don't have a payw wall up at at this point. So um it's it's a free platform to use, but essentially when you when you go through the onboarding process as a homeowner, the first thing you're going to do is you're going to put your address in. And what that does is it allows us to pull in a bunch of publicly available data. This is information that's already out there. And so we can start to kind of like paint a picture of what your home is.

Number of bedrooms, number of bathrooms, little things like that. Um, and then we start to ask a little bit more intricate questions, a couple of like editing some property details. Uh, and then we right off the bat ask you what are what value do you want to get from this platform? Are you looking for everyday comfort? Did you just buy your home?

Uh, are you looking to sell soon? because everyone that's coming into OPI as a homeowner has kind of a a different reason why they want to use this platform as a home management tool. We're all in different um I guess like phases of our homeowner journey. So, we want to make sure that we're pointing each of our users to the right in the right direction inside of Opley itself. And then when you get through the onboarding process, which doesn't take take too much time, um we actually have a phenomenal rate of of activation for for our users right now.

Um 78% of our downloads actually convert into um the first action taken inside of the platform, which is meaningful action. Yeah. So it's it's great because we're we're really like trying to show our users the value that they're going to get um right off the bat. there's no time wasted essentially. Um, and then inside of Opley, there's I mean there are a lot of things that you can do.

We're very featureheavy because there's so much that goes on inside of the home. So, first off, you can start to build a maintenance plan around your home. So, you add all these different types of um like OPI recommendations and all of these recommendations are personalized to your home. So, for example, if if your home doesn't have gutters, you're not going to get a gutter re a gutter cleaning recommendation. And what this does is it starts to add these to to your OPLY calendar so that you know you'll get nudges throughout the year on like, hey, it's it's time to change your HVAC filters.

It's time to uh flush your water heater. And these are such unsexy things to to do. Um and so what's exciting about each of these tasks is there's a savings associated with it. So whether or not it's like an educational um you know, hey, if you if you do this, you're extending the life of your system by x amount of years. This is how much you're saving over the course of the over its life.

Um or hey, we have a we have a a discount um that's exclusive from let's just ream for example for a water heater. If your water heater is certain amount of years old, you need a new one. So, like everything is kind of like tied together to help you as the homeowner make the right decision so that you can take care of your home properly. You can inside of Opley, you can um scroll through a bunch of daily deals so you can see all of these like aggregated discounts that that we've um pulled together for you on your home for like home like tools and cleaning products and scrub daddies and like things like that. Um you can have a quick to-do list.

So, you know, little little things around the house that you just got to get knocked out. Um, add DIY projects. Man, there's so much. Another thing that you can do is if you want to hire a home service professional, boom, the flow is so easy. It automatically writes the job description for you.

Um, and then that job description lands directly into the software that these pros are already using into their CRM. So, you're going to get notified very very quickly um with the information that you need to get that job done. So, uh really the the the concept of of OPPLY is to reduce the amount of stress as a homeowner um and to start to OPY starts to gets really smart on your home. It starts to learn the ins and outs, starts to learn how, you know, are you more of a DIYer? Are you more of a higher out?

and it'll start to, you know, make these types of recommendations um with personalized insights for you as a as a homeowner so that you can, you know, spend your time doing things you actually want to do instead of taking care of your home, which is always kind of like a burden to to homeowners. I uh I love this because uh as you were talking, I was thinking about a recent situation uh in the home uh where I live. And we had a washing machine that had a problem with uh mold. And I was, you know, horrified uh to discover this. But it turned out that uh something I didn't realize uh you have to do cleaning of it every month.

Uh and you know it's always would slip my mind and uh having those reminders I think would definitely uh mean that that washing machine would have longer life. So um I I uh immediately can can see the value proposition. Um what I would love to know is how did you get from the idea to actually putting this app on um on the marketplace? >> Yeah. Um I think going from like zero to one is is is a really huge hurdle and a really big challenge for early stage founders.

This was our second company. Um, but this was our first like app-based company really. Um, and and my co-founder is my husband and neither of us are technical. So, um, we needed right off the bat like we had this idea. Um, we had, you know, we did all the market research.

This was like before we had all the AI assistants. So, like we're like really digging into the research ourselves. Um, and what the first thing we needed to do is we needed someone technical on our team. Um, and in order to find someone technical, I needed to raise capital so that we could hire the right person for for that role. So, one of the first things that I set out to do was to raise a preede round.

So, we raised 1.2 million um in a preede round, which allowed us to essentially get from zero um to I'd say like.5 [laughter] um and what that capital allowed us to do was to hire we hired a CTO. Um we hired someone for product. Um and then that CTO basically um was the one who was you know initially building the in the prototype the beta version of this while at the same time myself and uh my Gabe my husband/cof-founder we'll call him co-founder in in this instance um we were going out and really marketing this in a local capacity.

We really just wanted to to prove we live in Nashville in Tennessee. Um, and we wanted to it's a it's a great market to to launch this because it's very like this is a very like homey type of uh area. Like we're not it's not very big city. It's a little bit more suburban. So, there's a lot more homes and there's a lot of new construction and new homes that are um being put up in in Nashville.

So, what we wanted to do was we would go out and we would set like sell this. We generated a weight list of I think we had like 2500 homeowners on this initial weight list before we had even really even started to build a product. So we kind [snorts] of like tackled it in multi- multi-stages and everyone was kind of um we put this this little mini team together raised a little bit of capital um and at that point once we got um OPPLY onto the app marketplace we got it on both Google Play Store and the um Apple store that's when we got to convert our weight list into actual users um which is another challenge to go through. Yeah, that's such an incredible journey. And um I would love to know uh uh am I correct in um thinking that you haven't raced before?

Um so how did those first few investor meetings uh go? It's so funny cuz when I think so we've raised 6 million to date. Um so we've we've we opened up a seed round and closed that last year. Um, but thinking back to like my one of some of my first pitches with VCs, I was like, "Oh my gosh, I had no idea what I was doing." I I was like, it's really like funny to like look at your first version of your pitch deck and say like, "Wow, I I really put myself out there.

This is what I was doing." But it's just one of those things where like I feel at every stage of being a founder, you're always going to look back and say, "Oh my gosh, I didn't know what I especially as a first- time founder. I didn't know what I was doing." But that's that's part of this. That's part of the of the journey.

You have to learn. You have to make mistakes along the way. And yes, of course, the initial conversations were were rough. I at that point, I didn't realize that everyone didn't just want to give me money. I was like, "Oh, I had a I have a I have a phenomenal background.

I'm at Harvard, like all these I have this great idea. Of course, you know, defense tech firms don't care that I served in the military and but I'm building a prop tech company. Like having having the um wherewithal to just like put those like I just needed to I was not doing a very good job of like putting myself in front of the right types of investors that had the potential to say yes. And that was something that I learned pretty early on. And then I could finally like refine who I'm talking to and at what stage.

And I started to learn a little bit more about the investor's psyche, you know, what are they looking for? What are the economics that um that like what are the returns that they're looking for as a as a fund? When are they deploying their capital? and really starting to understand the the VC world allowed me to really position the vision that I was selling at that point because we really in a preede round I didn't even have anything built because I needed the capital to hire the the technical person. So I was selling a vision and I was selling myself and my co-founder as founders that are committed to this 100% dedicated um and we will be the ones to figure this out.

like it's really in my opinion all about like authenticity, all about momentum, like those types of things as as you're going through the fundraising process. So, all that to say, I know it's kind of like long- winded. Um, it was ugly at first, very ugly, but eventually when you when you start to to kind of figure out the game of raising capital, it it starts to fall into place a little bit better. And then once you get your first yes, those second, third, fourth yeses really do start to fall into place. What I've learned is, and no, you know, shade at all to investors, but a lot of them like to follow.

If you have uh a good terms that have come on and you know, you've had a firm that's done some diligence, uh even in a preede round, we call them a lead investor, other investors will will follow that. So landing that first lead is a huge challenge, but once you get that, it's it's a little bit easier there on out. And how did you find those right investors because um that must be really challenging finding someone who will not only invest the money but also their knowledge and really help you grow that business. Yeah. [gasps] So really I think what it came down to because we were so early raising that first bit of capital and I think this kind of goes into our seed round as well is I was looking for an investor who believed in me who believed in the vision that we were building.

It's we we really had no traction. There was no revenue uh to raise off of. It was it was truly let's find someone who understands the space even a little bit um and who really believes in in us as founders and that we can take this company and make it absolutely huge. Um in terms of like the specifics on which types of investors we really relied heavily on our um network. So there were a couple of um veteran VC firms who invest nearly exclusively in either academy grads, so like West Point, Naval Academy, Air Force, or um in veterans.

Um and so that def like digging into your network even as niche as it is, that for sure helped us um raise that first little bit of capital. And it also did help that I was in business school. So I could I could rely on some of the resources at the school. So um inside of the innovations lab, you know, they had VCs who would just sit in booths and just wait for students to come in to practice their pitches. So I could just practice with a VC.

And that's like where I started to to learn. And I know, you know, that's not always the case for every founder where you have the opportunity to just, you know, practice and and fail um on purpose in front of someone who has the experience and can lead you in the right direction. Um I would say that's a very privileged position that I was in, but I definitely took advantage of of those resources as well. >> No, that's incredible. And uh you know uh being a veteran I I was wondering how actually um the investors took it whether uh it opened doors or was it harder to do because you didn't come from business background it was really the first time that you're um raising capital for a company.

Um so what what was the attitude that they had? >> Very hit or miss. It was either oh wow like this is this is uh veterans make phenomenal founders. You guys have the grit the commitment um or it's you have no idea what what what like what gives you the right to start a company essentially. So it was very very split and there was a lot of um I would say convincing a little bit to a certain extent.

I don't really think that I think that when an investor comes to the table and you sit across from them and you're talking to them about your business, I think you have about like 30 seconds to sell this investor. If they just don't like you, they're like is changing their mind is nearly impossible. I mean, it's there's there's a lot of um you know, they they obviously want to invest in your business, but they're also investing in you no matter what stage of the company is at. So like that if there was an instantaneous like ooh veteran background it just wasn't really going to work. You know there you could try and explain the difference between hard and soft skills and yada yada and how important leadership really actually is in an in a in a company especially an early stage company.

Um but um it was it was very much like 50/50 I I would say. I would honestly though lean maybe not 5050 if I'm thinking about it. I think I would lean more towards like 7030 in favor of us being veterans. Now us [clears throat] being a married couple definitely raised some red flags that um we had to skirt around just because there's um there's liability, right? the, you know, but the the ironic thing is is there's there's liability regardless of whether or not you're a married couple who's co-founding because if if you're just friends that are co-founding or you just met this person and you guys want to co-found a company together, there's there's always going to be tension and liability.

But the the married couple aspect, a lot of investors just exclusively do not invest in married couple co-founding teams because if something were to happen in our personal lives, in our relationship, it drastically affects the company. So I mean, Gabe and I have been together for I mean at this point like 15 years. We've been in the mil. We've been through deployments. We've done really really hard things in our lives and that was that was kind of like the hurdle that they needed to hear that we have already been through to prove that okay we can take this on and plus it was our second company as well different type of company but second the first one was successful we sold it it was great so like we have a little bit a little bit of proof that we can do this together >> no it's uh I guess I can see it uh from both sides, right?

Uh where you know someone really well, but at the same time that aspect of being in a relationship and something breaking down uh might uh really impact the business. So were there any other objections that uh you would hear um and that were repeated by several investors and and what were uh what were those? So, we're building in a really, really hard space and I bet I mean every every founder thinks that, right? Like you're not going to start a company that you think is going to be easy, of course. Um, but our space has been tried a lot of times and there's been a lot there's a lot of companies in the graveyard in in like this how to capture the behavior of a homeowner, how to um like help a homeowner's specific life.

Um, and we had initially started out as kind of like a more of like a marketplace where we knew we needed to have like a a bunch of home service professionals because a huge part of being a homeowner is being able to hire a pro very easily. And so, of course, there's companies like Angie's and Thumbtac. And so, that was that was a one hurdle. Well, what's your differentiator between these big behemoths that are already in the space? Another one is um >> well this this has been tried and tried and tried again.

What makes you think that you're going to be the one to be able to solve this problem? Um, and I love I'm so excited for the I mean, we're still, you know, we're still early stage, but it's it's we're really making some moves in the space and I always like it's such fire and motivation for me when someone tells me I can't do something and I'm like, okay, let's I'll I'll make sure that you that I'll let you know when this works out. [laughter] Um, and so like that was definitely one of them. [snorts] Um, I would say I would say to a certain extent, and I am not the kind of person to just be like, oh, it's because I'm a female, but I do think like women, CEOs who are raising the capital have a little bit of a harder time. Um, I felt like when Gabe was on the calls with me, conversations always seemed to be a little bit easier.

It's different questions that are being asked. There's just this like psyche. Most investors are men. They want, you know, it's just easier for them to communicate with a guy. So I think like that was a little bit of a hurdle as well.

Um and then in just terms of the like overall um like concept and the vision that we were building there there was some some questions around the complications of like cuz how we're building this it really determine it's really based off of like how much data we can get on the home itself. Uh, and it was like how are you going to actually get that data? Because that's what feeds our model. That's what feeds our prediction engine. And that's like the technology that took us two years to build and it's really predicated on how well we can learn about your home.

It's basically like more information in, better information out. Um, and so that was a little bit of a hurdle for early stage investors. uh mostly because it was like really early stages in the AI world like how are you going to actually build this predictive engine you and your co-founder don't even have a technical background. So um there I mean yes hurdle after hurdle [laughter] after hurdle after hurdle is kind of what I'm now thinking like yeah it was tough. Yeah.

No, I I think it's uh I imagine that it's similar to sales where you know you are bound to hear no and several hundreds of times before you hear a yes. Um I would love to know uh how did you once you have raised money what did you have in mind in terms of where to actually allocate those funds because you said you hired the CTO but besides that how did you decide what are the biggest priorities uh at that at that stage? Yeah, it's a it's a really really good question and I think this varies for every company um and for every founding team how you're going to allocate that capital because everyone is strategizing their company a little bit differently. Um we built we were ve we are very data driven and very analytical. Um, we make these decisions within our company based off of like exact patterns and and data analysis of like what truly is going on either inside of the platform or outside in the market space.

Um, and so how we thought about allocating capital was we did not rush into spending the money. We knew we needed a little bit of a team. um we know you know and this I think this comes from our military background surrounding yourselves with people who are experts in their field um is the one of the best things that you could do you know like we needed to hire some AI engineers we needed to hire um some like a a mini product team essentially so that the engineers knew exactly what to build um >> and that's like really where we spent our capital up front was we invested in the in the team and the people. Um we I mean of course you have like your software and yeah all of the Carta and all of like the business side of things that you're spending money on the accountant accountants and whatnot. Um, but it it really was a a slow a slow burn, a very controlled burn because it was 90% of the spend was just on the team itself.

Um and then that initial capital that we raised like we didn't spend anything on marketing because we we really wanted to um nail >> I like we are a we are a um nationwide product anywhere in the United States can use OPY but we were kind of using um Tennessee as our as our test bed um and so it was it was very cheap for us and we were very strategic in that sense um and we didn't spend any any money in marketing um this product. We did everything through organic socials and earned media. So, we didn't spend we didn't put any money towards towards any customer acquisition whatsoever. We actually had a zero cost to acquire a customer for almost two years. We just recently started putting money behind um acquiring users because we we nailed our messaging and we were very very strategic in that.

Um, so really the majority the majority of the funds went to the team and we paid off some legal bills, you know, from the raise itself and I don't know like that was that was pretty much it for for a while and then we just raised um that second um chunk of change and that's when we started to expand our team a little bit um hire hire additionals and um we have just recently started to put some money behind um some marketing H that's been uh that's incredible that you've been able to do that. And when you think about monetization, what is going to be the strategy there? Uh because when you said that uh on the platform you have access to a lot of professionals that can do those um those jobs that are needed to be done. I imagine that you can get referral uh fee. Um but what is is that something that uh you'll be doing and also what are the ways you are thinking about monetizing the the platform?

>> So this is this is another thing that took us a a while to develop. Um we set out to be able to solve homeowners problems. Um and one of the problems that home owners face is hiring home service pros. It's just a frustrating process. It's hard to communicate with them.

It's hard to get them on your calendar. So on and so forth. Um but building a marketplace like uh city by city is a very very slow and challenging thing to do. That was another thing investors just were not for. They wanted something to be able to scale overnight.

So what we were actually able to and we're the first the first company to do this. We actually integrated into the pro CRM. Um, so we got a partnership with a CRM and we built um software inside of their CRM. So every time a homeowner inside of OPPLY requests, say a plumber, that job gets routed directly to that pro CRM. And the pro is not paying for that lead.

The pro is only paying if they invoice that customer. So it's an outcomebased marketing for for the pro. Um, and the percentage it's a it's a it's a small percentage of the job that the pro pays to us after they've invoiced the customer. And the reason that we can do that is because we know exactly when they invoice the customer because we're connected to their CRM. So, it's a very very seamless and integrated process um where we're not sending out invoices, we're not charging per lead.

So that that's like number that's how we've been generating our revenue um for a while now is is through that process. But we are actually um in November towards the end of November on Black Friday we are launching a whole new feature um of Opley [snorts] and part of it will actually be behind a payw wall. Um, and this new feature is we've been working on business development and partnerships with big brands, um, like Home Depot, Wayfair, all of these brands that are very, um, connected to the homeowner and solve a lot of homeowner problems. And it's going to be massive exclusive discounts. So, we're going to tie the current product to what we already have, the maintenance plan, the recommendations, the to-do list.

Basically, anything that you need to do to your home, you'll be able to find a discount or a savings associated with that. Whether that's on a product that you purchase from a store like Wayfair or Home Depot or it's a local pro in your area. That's another like big aspect of all of this is um a lot of the t the time these pros are running deals but nobody goes and checks their website to see what deals they have going on. It could be something like hey 50 bucks off or 25% off if you're a first-time customer and the home ownership is so expensive. Like it is ridiculously expensive.

Everything costs so much money. And we want to not only help homeowners manage their home, but help homeowners save. So, we have aggregated tons of exclusive discounts and exclusive savings and local um discounts from pros who can service those needs. And so, that'll be an additional part of our revenue model um where homeowners will have access to all of these exclusive discounts that they can't find anywhere else. This is not publicly scraped data.

This is partnerships that really want to help homeowners. Uh I love the fact that you are uh taking that fee after the job has been done because uh it's such a strong value proposition for uh for that pro to be able to actually get that lead for for free basically and only pay for it if it converts. Um I think yeah it's it's super smart idea. >> Thank you. >> And um when it comes to uh how you decided on um how the platform uh should look like you mentioned that uh before you launched you spoke with um you you created a waiting list of I think it was 2500 uh people.

How did uh reaching out to them to these homeowners change how you looked at designing the product? Yeah. So, it's so different and it's always changing because we're talking to homeowners on a daily basis. And I think one of the the initial assumptions that we had going into this was homeowners of of course are going to be willing to upload a bunch of documents on their home. Um their inspection report, their insurance policies, any warranties that they have.

Of course they will, right? Like you know if if they upload it and we have access to it, we can then help them more. >> It's just not it's just simply not the case. one because your inspection report if you're an existing homeowner is somewhere buried in your email and you have no idea where it is. >> And so after um the the concept of being able to say like, "Oh, just upload your inspection report and we'll be able to make a maintenance plan off of it.

" Like sounds really great, right? Like weight list, add it to the weight list. Of course, this sounds great. But then actually getting that user to perform that action is a very challenging thing. There there has to be either such a strong incentive behind it.

um it has to be positioned at the right time in the right place inside of the app. Like there's so much psychology that goes on um like behind the scenes to learn and understand like what the behaviors of your user what behaviors do you want your users to actually take so that you know you can provide the most value to them. And so with that initial assumption of yeah they're just going to do this thing of course they will that was very that was very off. So um we needed to completely change that whole experience so that it um well one we started to partner with inspection companies so that the inspector the inspection report would be automatically ingested into the platform so the homeowner wouldn't have to do anything. Um, but then on, you know, other instances where we are not partnered with their specific inspection company or if they're existing homeowners, it's it's all about positioning the the upload in that instance.

Not like right up front. It's not like part of onboarding at all. It's an it's an option. It's if you want to do it. Um, and that what we because what we saw was initially like people weren't doing it and we're like, well, what the heck?

Why aren't why aren't they uploading it? like what this what do you mean they don't want help with X Y and Z or to find you know cheaper things but um it's it's just all about >> where things are positioned in the app what the like psyche of the flow is when you start to go through the platform itself how you're directing users to be able to extract the most value from it I don't there's there is there's a lot of a lot of change that has gone on since V1 that has been launched launched. Um, and a lot of smart people are working behind the scenes to make sure that it's a seamless experience. It's Yeah, it's fascinating to to learn about all of that and and to see the transition over time based off of user feedback. >> No, 100%.

And you know, when it comes to uh the metrics that you look at, what are some of the things that you prioritize? I know uh a lot of people when they're building an app, they focus on day one versus day 30, whether you're able to uh keep that user on the platform uh or is it maybe whether they uh log onto the app every day? What are some of the things that you um uh you are focused on? Yeah. Um a lot of engagement metrics.

So >> we So if you think about maintenance on your home, you're not doing you're not opening up an app to get a notification because you got a notification to change your your HI filter every day. It's just not an everyday type of type of platform. Now, we're holding ourselves internally to a high standard. We want our users inside of Opley at least every other week. So, we track everything on a bi-weekly basis.

Um, and there's a lot of um like retention um like features, whether that's like email campaigns or different types of push notifications or like um different types of actual features inside of the app that are much more routine things that you would be checking that we've started to implement. Um because we're looking at things um like our northstar metric for OPY as it stands right now. Um, we might be adjusting that ever so slightly in the future, but right now it's actions taken inside of OPY. And >> the caveat there is I don't care if a user is opening up Opley and checking a couple of pages. I want that user to take a meaningful action inside of OPY.

And what that means is they're interacting with the chat. They're uploading photos and asking for an analysis. They're hiring a pro. um they're adding their own project, they're you know saying that hey yes I did take that recommendation and I completed that task. Um so those are the things that we're tracking and right now we're seeing on average for our engaged users every um every like bi-weekly they're taking on average around 23 meaningful actions inside of the platform.

Um and so it's it is um you know the the focus that that we have been really aiming towards is getting those users to fall in love with Opley. create a platform that they there's a high high stickiness and high switching costs um so that they feel like I'm not going to go to any other platform because this has been so helpful to me and it already starts to it has already started to know me um and it has already started to you know make my life easier as a homeowner and by being able to track um retention of course um like we we track more like day 60 retention we know all the metrics for you know what is the activation rate like what is our entire funnel of course we want to know from top of funnel all the way down to an activated user what is that percentage at each step um how many people are currently um editing property details how what is the number of um like the the growth month over month of new activated users of course um there's just there's a a whole slew of of metrics that allow us to paint that picture of is this are we hitting product market fit? Um and everything would at this point lead towards yes um because we have strong engagement um on a bi-weekly basis which is the standard that we set for ourselves and um solid retention um at that at least month two the 60 60day mark. Um, and so once you basically like what we're learning is if a user sticks around for two months, they're much more likely to stick around for month three, month four, month five because we've captured them um and we provided enough value at that time. >> Um there it's super interesting.

Um and a lot of platforms they have that idea that oh you have to be using it every day otherwise it's not successful. But like you said, you know, I don't want to think about fixing uh something in my home every day. Uh in fact, it would be a nightmare. Uh so I love the the approach more. [laughter] >> Yeah.

So I love the approach that you've uh taken. And and how do you think about acquiring customers? Because it seems like it's such a big task because when you think about homeowners, there's I mean there's so many people. So how do you think about how are we going to actually market to uh to those uh people? One of the things that we have started or that we started to do early on was because we're a consumerf facing platform, we knew we needed to build a brand around OPPLY um like your home's operations ally.

Like that's, you know, Opley. That's kind of like what it means. >> Um and how do we do that? We do that through organic socials. Um and so what we've learned early on is that um and we have I mean we haven't gotten crazy.

We have like 20,000 followers on our Instagram. So like that's like our strongest platform. We have subscribers on YouTube. We're obviously on Tik Tok. Um and that audience has given us tremendous insights.

Um and then what we do is we can create lookalike audiences. Um and take >> pieces of organic content that have organically succeeded, done well, and put money behind those and run ads off of those. Um, and what we've actually seen over the past even just like the past couple of months is the messaging that resonates the most and it has actually um I mean our cost to acquire a and an install at this point um is $144 because we've nailed >> the message. Yeah, it's like crazy low. Like it's very like because like >> the messaging that we've honed in on is is really resonating and it's and it's all about saving money.

It's all about the cost of home ownership and how expensive it is and where can we go as homeowners to ease the burden of all these expenses that we have sitting um on our shoulders when it comes to taking care of the home. So that message has resonated really really well. Um, and that's what kind of has allowed us to like open up this whole like, hey, this cost savings is such an important aspect of of what we're building and what we're what we're doing and how we're helping homeowners. Um, so the messaging is number one and for the for the cost to acquire. And then we have hired a lead of consumer growth.

I'm not the person that's running like I'm not behind running the ads, but this guy has like he is a a freak of nature when it comes to um putting money behind pieces of our organic content because he's been able to drive our CAC down to I mean below $2, which is which has been incredible. Um >> and it's it's thorough experimenting and it's using organic content that has worked. Um, that's like really our that's like the secret that we're kind of like running after right now is post something, see if it does well. If it doesn't, we're not going to we're not going to waste our time. The messaging isn't there.

And then create lookalike audiences off of the the message that is resonating. And a lot of it is coming down to the cost savings. No, I I love the fact that you're using the content that works because that lowers that cost of acquiring customers uh significantly. And um when it comes to the your the role of your personal brand, I know you post a lot of content from your uh your own channel on on Instagram or other social media channels. How big of a role does that play in uh marketing the product um and acquiring those customers?

So my my social media and my um like strategy there is less about customer acquisition. It's a it's a little bit about like brand building. If you like if you watch my videos and you get past like you know the first 30 seconds I always kind of like throw in OPY into it. I'm like really like my my gist, my strategy behind my content is I take something that I experienced or learned in the military and it's always like a leadership lesson and then I tie it to the business currently. So whether that's, you know, I used to fly attack helicopters for special operations and we um were always every single mission we landed on target plus or minus 30 seconds.

So the root the margin for error was very very slim. And so I would take that concept and I apply it to our business right now and I and I bring that into um my my content and and I always bring up OPI like towards the end. I don't want it to like sound like an ad or to sound gimmicky. So it's it's strategized in that way. But my content is is mostly to it's been driving a lot of like partnership conversations is what I'm what what's been really really nice.

It's less, you know, hey, this video has gotten us >> a thousand downloads. It's way more, hey, this person, this person of importance saw my video, reached out on my LinkedIn, and now we're in partnership conversations. Um those are the the targets I guess for for my social media. And then of course it's like you know I always I always want to be an authentic person. I have a very unique background.

It's very different than most founders you know building in the in the tech space. >> Um and I just I I uh >> I want to you know ensure that our users if they go and they find the founder they can trust they can trust me. you know, as like as cliche as that sounds, it's it's really also just like I just want to portray who I am um as as Lindsay. And you know, I've done some like pretty aggressive, tough, demanding things in my life. And I want our users to know that there's a real person behind the product.

Um you know, there's there's real human beings that genuinely care about solving these problems. Um, and that's like another kind of aspect of of my socials is just building that that trust around the founder, the founding team. Um, and who we are as a company. You know, we are there's >> West Point has where I went to college has this creed essentially. It's a cadet will not lie, steal, cheat, or tolerate those who do.

And it's really just all about integrity. And it that's just such a core core core value of mine and of my husbands who also went to West Point. And being able to try and like just portray that in some way to our audience to for them to know like these are good people like we care. We want to solve real problems. We want to help real people.

Um and that like trust building is is another kind of like aspect. So partnerships and trust building. >> No 100%. And then you like you said you have such a unique story and in general I think there's a big shift uh with consumers where they want to see who is behind that brand uh because that's part of the thing that they want to buy. They want to support not just the brand but the person that built that brand.

So, uh I love the fact that you're sharing it with uh with the audience. Um and when it comes to your background, what are some of the habits from your years in military as a helicopter pilot um that have been fundamental in how you uh are as a business owner? So, one of the one of the things that the military does a really good job at is putting uh service members in very stressful situations. Um, and this and I mean, as one could, you know, pick up on in the military. Um, and what's really it's kind of like two a two-prong thing that I that I like to take into into the business right now.

one, it's how to lead when you're under stress. As a founder, there are so many instances where you feel like the company is about to burn to the ground or a competitor just came out of the weeds and they're absolutely crushing it. Uh an investor, you know, is is barking down your back about your retention, whatever it is. And you as the founder have to be able to absorb all that and all that stress on yourself and then you have to go back to the team and present a solution as opposed to just bringing that you know external pressure to the team. And that's something especially as like as an officer in in the military that's like exactly what we did day in and day out.

It's almost like the shield, right? like you if we were in combat and something's and something's happening, I'm the one on the radio, so I'm the one receiving the information and I, you know, as a helicopter pilot, this is a little less applicable. It's more applicable to Gabe, my husband, who was an infantry officer, but he's receiving information into his earpiece and he has to lead a bunch of soldiers through, you know, a village in Afghanistan when really crazy stuff is going on. and he has to be able to like lead all of those guys and ensure that they have the right amount of information so that they're making the right decisions and that they're doing the right thing um while bad things are happening all around. So, it's a it's a similar type of um type of concept.

Obviously, we're not getting shot at in in our startup, but those that that has has really helped um be able to lead a team, you know, and not bring all of that external noise that's important, but it's noise that could be very distracting to your team so you can keep everybody as focused as possible. Um, another thing is um really just like for me it's like the grit of of it all. >> Like being like this is starting a company is >> like you have to be in it for the long haul. Like this is not something that you're just like at least most companies you know some people get lucky and you know massive scale and then acquisition a couple years down the line but like we're in this for the long haul. We've signed up for 10 plus years of a grind and that takes a certain kind of of of crazy.

Like it takes a certain kind of individual who, you know, actually enjoys the journey of it all as opposed to just this like this outcome that seems so far away. Because if you're just so hyperfocused on this one outcome, that whole 10 plus years is not going to it's going to be basically >> miserable. Yeah. [laughter] >> Yeah. And it's just going to it's never you're never going to like be able to make the right decisions because you're going to be thinking about just like that last little piece there.

And so that is like something that the military has has taught me is to enjoy the journey of this very very long long road that we're on. Um, and just being able to like put your head down and work day in and day out. That like that grind and that grit. Don't get distracted by shiny objects because there's a lot of shiny objects out there. [laughter] No, it's so interesting.

And I think the aspect that you said about uh kind of protecting your team and making sure that they're focused on what is most important is so so crucial. uh because uh there's so much noise and especially if you bring on investors, you know, they put money in and they expect results. So, um that brings another layer of um of stress, I imagine. What I would love to know is what are some of the things that you had to actually unlearn from military that were not working for you as a startup founder? I think that also comes down to leadership if you can believe it or not.

So it's it's kind of it's kind of like paradoxical because in the military you are bound legally to follow your superior, right? Um so whether or not you like them, you still have to do what they say. In the the real world, that's not the case. If somebody doesn't like your leadership style or they don't like how you're running the company or they think, you know, you have the wrong intentions, they can just quit. They can walk away the next day.

Um, and so >> understand it wasn't necessarily like something that I needed to change. I think what it was was um learning how civilians is like kind of like what we would call them. Um, like how civilians work and how they're motivated. And it's and it's different than what we did in the military. Um, other things I used to curse a whole lot more.

I'm trying to tone my language down a little bit. That is just like part of the world. Um, other things in the military. I we were especially when I flew for special operations, we were all very very type A and everything was planned. um and executed to near perfection like and if it wasn't like exactly how we had planned it, there was a massive debrief on that one little thing.

For example, >> in the in the startup world, it's much more fluid. You have to be able to like adjust on the fly. I mean, we would we could adjust on the fly. Um but it was but it was like a planned adjustment on the fly, if that makes sense. Yeah, >> in the in the startup world, it's like it's kind of almost like we're like we have to be like type B.

You can't make sure that like every email is written to perfection. Like you just got to send the email. You can't make sure that like every little thing is is perfect because it takes too much time. Like we we we got to get stuff done. And so that's definitely like one thing that I'm still learning like cuz I'm a very typ structured person who proofreads my emails 10 times to make sure there's not a a spelling mistake or I'm not missing a punctuation or something like that.

And um Gabe is much more like just send the damn email. [laughter] And so that even just like little things like that. I don't know. It's just I just got to just care a little bit less about some of the particulars so that we can keep going with the things that matter the most. >> Yeah.

It's it's like they say that, you know, being 80% there is better than not going through with something at all. Um and having to keep reminding yourself that is uh is challenging. [snorts] um when it comes to um women building uh AI companies, what um what do you think are some of the biggest challenges and also how do we how do you think we uh change the narrative so that there are going to be more women building building companies and not just being users or employees within those AI companies. Yeah, I think some of the biggest challenges that women face um are around fundraising um and around hiring. Uh what I I mean I come from a like we've mentioned a ton of times like a very like maledominated background.

I mean, I was the only female ever in US Army history to fly the the helicopter that I flew for special ops. So, like it was all guys and me. So, one of the things that um I I I resonate with guys a lot. I can have the conversations, but that's not all that's not the case for all women. So, I think that that when it comes to fundraising and when it comes to hiring that those two things are are very challenging um >> if you're trying to hire like more of like a like a male um dominated kind of company like we have like actually we don't have any women employees at this point.

Um and and another thing um I think that women how to change this narrative is all it's going to sound cliche but it's all about confidence. No matter who you are what people want to follow is a confident person who has competence. Like if you you know you belong in that room, you know that you have the experience that you are the right person to solve that problem that if you don't build it like it it might not ever get built like that. You have to walk the walk and talk the talk and be confident in who you are in what you know and how you're going to solve that problem. Um I just find that like I I do a decent amount of um like public speaking um at like leadership conferences, women in tech conferences and a lot of the the questions always revolve at the end around like well I have such imposter syndrome because and if we as like women in the industry could could come together and understand that imposter syndrome is actually a good thing.

What that means is that you have earned that role and that you deserve to be in that position. Whether that's the CEO of the company that you founded or um maybe a promotion that you just had like whatever it is like it's okay that you feel imposter syndrome but you have to put that behind you so that you can make the right decisions when the time comes because um that imposter syndrome like fear is debilitating. It can it can really really it can really hurt you. For me personally, one thing that that I've struggled with over the years is I always lack confidence when I first start something. I always think to myself, well, I need experience in this before I understand anything.

Um, or that I can succeed. I have to like I have to sit back and take a like secondary role before I feel like I can step up and and be in the position of of leadership or making decisions or influencing of any kind. >> And as I've gotten older and as I've put myself in more like challenging situations, what I've learned is I shouldn't ever feel like that because everybody feels like that. Regardless of gender, no matter who it is, everyone is feeling that. So if you're the kind of person that's that's that's able to step up to the plate like from the start, you are just going to shine in a room full of people who are scared to step up to the plate.

So just do that thing. Um it's it's a really tough thing to do and you got to be able to trust your judgment. We got to be able to, you know, make mistakes along the way. But man, it's just let's just get rid of that fear of feeling like we don't belong because it's just simply not true. That is such a good advice and I really uh you know resonate with that um with that as well.

Uh and especially as a business founder, most of the things you're doing, you're doing them for the first time. So for someone who is uh very much type A, it's it's so challenging to uh to to do those those things that you're doing for the first time. Um, if you could send one message to um to the audience and those in the audience who want to build their own business and who want to launch an app, what would be that message? What is something that you have learned through the experience that you have had uh and as you're on that journey? Well, if there's someone that's out there that wants to do something, they have to commit to it.

That would be like my biggest piece of advice. Without commitment, there's no there's no magic that happens. If you are half in something, half out of it, weighing all of your options, like creating a bunch of optionality for yourself, then that that success that you want, you know, that company that you want to build, it's it's never going to get built. So commit to it and and just do the thing. Like you are going to make mistakes, but guess what?

Those mistakes are learnings. And you are you're going to be on a journey that you're going to experience constant learning and that's going to make you such a stronger person in the long run. Like just commit to doing what you want to do and stay committed to it. Don't start it and then stop it. Stick with it.

>> [snorts] >> There's uh there's a incredible message and um definitely this is uh you know being kind of one foot in the door and the other one sticking out it definitely doesn't work when you're starting a business >> and when you're starting to go fund raise. If you have a full-time job and you're like talking to investors and they know that you haven't like there's they're not going to invest like you have you have to commit to to the thing that you're doing because it's it's not going to work if you're not in it full like 24/7 basically. >> Yeah. I uh I love this conversation. So, um, uh, I feel like I could speak with you for another two hours, but, um, let's do a a quick, uh, a fast round if you're okay with that.

>> Sure. >> Um, so what is an an AI use case that has really surprised you um, within within Opley? Um, I would say an AI use case inside of Opley. Um, I would say our our prediction engine, um, and how it makes recommendations for our users based off of their homes has absolutely blown my mind. Um, because of how because of how good and how accurate it is.

Um, and the recommendations are are timely and they're pertinent. And we've had so many users come back and say, you know, I I really did need to do that thing. I was thinking about doing that thing. How did it know before I even, you know, was was going to actually do that thing? So, the recommendation engine, I would say, is has really um been a winner for us.

>> No. Um 100 that's uh that's a great uh feature. Um what is the thing that people get uh wrong most often when it comes to building a uh an app? I think the thing that people get most wrong is that if you market, everyone knows we exist. Um like if if we're running ads, everyone knows we exist.

Our neighbors don't even know that Opley exists. You know what I mean? Like it is Alex Hermoszi actually um said this. So, >> he was like walk he's from Las Vegas and he had this huge book launch and he has been spending millions of dollars on on advertising everything that he had going on and he was walking down the streets in um Las Vegas and was ran into a fan and the fan didn't even know that the that the book launch was happening and it's just like even in his own city and as famous as he is that person didn't know that they existed. I had, for example, I have um my my sister-in-law like chat GBT had come out and everyone's using it.

I'm thinking to my like I was at HBS at the time and I'm like, "Oh, wow. Everybody in the world knows about chat." And she had no idea. She was like, "What is chat? Gp what?

" Like, and I was like, "Wait, wait a second." So like as a founder and you're starting your marketing journey and getting people aware of your product, you cannot assume that someone knows about it or has heard of you. So like you have just got to stay relentless in like you can keep telling the same story over and over and over and over and over again because I bet you like nobody has heard it. So just keep saying it. Just keep keep getting your message out there.

>> Yeah. I think uh you get into this silo where you have heard uh you know you have heard yourself saying that story so many times that you know everyone knows about it but >> that's so not true. [laughter] >> That's so not true. Um and finally what is something that you miss about uh flying? >> Oo so much about it.

Um, one, I miss the people the most from from like my old units. Uh, some of my best friends. Like these guys were just like the the best human beings that I've ever met. Um, and then in terms of like flying, I I kind of in a so I flew attack helicopters. Um, so we had a ton of weapons on like I flew the Apache, we had Hellfire missiles and rockets and a 30 mm and then I had miniguns and 50 cals on the other.

Um, so it was like very aggressive. I like weirdly missed like the smell of like after a round like that. Like it just like always like was like okay. It got me like pumped up. So I I missed that.

Um and like shooting a helicopter is a very fun thing to do. Like it is definitely like if you got to the range and you're and you're like aiming a helicopter at a target, it's it's a it's a good time. >> Oh wow. Um, thank you so much for for sharing all of this and I, you know, I think I will have to listen to this conversation again because there was just so much incredible advice. So, uh, thank you so much, uh, for for sharing all of that and, um, and sharing with the audience the all of the lessons that you learned.

>> Thank you so much for having me. I hope Yeah, I hope there's just one tidbit of of advice that that someone can can pull from this. So, I appreciate the opportunity to share. [music] This conversation with Lindsay was absolutely incredible and I've learned so much about starting a business, how to handle investor relationships, and so much more. So, if you enjoyed this podcast episode, please follow the podcast and share it with a friend.

It really helps the podcast grow. Thanks, and I'll see you in the next one.