From Risk-Averse to Founder: Betting on Myself

Ashley Maguire spent years chasing stability—good benefits, a steady paycheck, and a “safe” career path. But when she looked around, she realized something: The founders building companies weren’t smarter than her. They weren’t more qualified. So why was she sitting on the sidelines?

In this episode, Ashley gets real about breaking free from the employee mindset, stepping into the founder role, and refusing to self-select out of opportunities. If you’re waiting for permission to go after something bigger, consider this your wake-up call.

Follow us on Tik Tok @shesambitiousaf for more content and episode teasers!

Transcript

Angelica Maestas (Host): [00:00:00] Welcome to She's Ambitious AF, the bold and empowering podcast that turns up the volume on female entrepreneurship. Join us as we dive headfirst into the wild world of boss babes, where we spill the tea on all things, ambition, success, and the occasional hilarious disaster. 

Angelica Maestas (Host): Welcome to another episode of She's Ambitious af. Today I'm joined by guest Ashley McGuire. Ashley, why don't you go ahead and introduce yourself.

Ashley Maguire (Guest): I am Ashley McGuire, and I'm the CEO of Helen's Foundry, which is a software company for early stage software companies. We're very meta in that way. yeah, and I've, I've kind of spanned tech my entire career. I started as a software engineer, moved into user experience, and I'm on this CEO path, which was not what I was expecting.

Angelica Maestas (Host): Awesome.

Angelica Maestas (Host): on that note of unexpected [00:01:00] paths, it, it sounds like you did not grow up expecting to be an entrepreneur.

Ashley Maguire (Guest): No, not in any way, shape, or form. I did grow up around computers that, that I will 100% vouch for. My dad was a hardware engineer I'm originally from the Silicon Valley.

Angelica Maestas (Host): Huh.

Ashley Maguire (Guest): San Jose if anybody's interested. But yeah, my dad worked for Apple coming out of the garage. He worked for Atari,

Angelica Maestas (Host): Wow.

Ashley Maguire (Guest): and went on to work for a bunch of like the, the local kind of garage startups We always had a computer in the house, at least one, and I started writing code when I was in middle school and had a, my own website and blog,

Angelica Maestas (Host): Ooh.

Ashley Maguire (Guest): Throughout high school. Moved into that, I, I got an internship my senior year and ended up working for New Mexico State as their baby intern for the web development

Angelica Maestas (Host): Oh,

Ashley Maguire (Guest): and that's, that's where I

Angelica Maestas (Host): Wow. Well, what a cool experience. I didn't know that about your background and where you grew up. Did the [00:02:00] exposure to those garage startups. Make you not want to go down that path of entrepreneurship or, or how did it make you feel?

Ashley Maguire (Guest): I think so my parents are, are very old school in this way and they were very like, you know, good Protestant work ethic and just work really hard and I'm the first person in my family to go to college. So my parents didn't have that opportunity and they were big on like, fine job security.

Ashley Maguire (Guest): So my dad eventually got out of the, the kind of like more startup fund

Angelica Maestas (Host): Oh, okay.

Ashley Maguire (Guest): basically right around the time I came along because he wanted the benefits that went along with like a, a secure corporate job. So even though we were from the valley and exposed to all of that, the messaging that I got from my family was, was very much about being risk

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): So even working for a startup, they were like, that's a bad idea. Don't do that. That like, you're gonna show up one day and there's not gonna be a company anymore. 

Angelica Maestas (Host): I mean, that's valid.

Ashley Maguire (Guest): that, I mean, it's valid. Yeah. And I [00:03:00] think that happened a lot with them. They were both in the, like the semiconductors and, you know, doing like electronics QA and things like that.

Ashley Maguire (Guest): So like that did happen a

Angelica Maestas (Host): Hmm.

Ashley Maguire (Guest): in the late eighties, early nineties in the Valley. And I think they just really wanted that sense of security for me as well. So I. I played it safe for a really long time.

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): the, I'd say the, probably the first half of my career I was like, oh, I got gotta find something with good, good benefits and a 401k, and I mean, kind of

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): being 25 years old and being like, I need a good 401k,

Angelica Maestas (Host): thinking about credit when I was 17. Like I was already, like those things matter to me and I was already thinking about them and how I would establish it. But very similar to you, I just had no desire for this unstable lifestyle and I was a young mom, and so all I thought about was stability.

Angelica Maestas (Host): Steady paycheck, health insurance, [00:04:00] those things, and, you know, eventually went down that rollercoaster. But for you, so you did you worked for corporate it sounds like, and then eventually you worked for, you did work for startups, right? I don't know if you'd consider them startups at the stage. They were.

Angelica Maestas (Host): But they provided some level of stability in terms of they wouldn't be gone overnight. So what was. What was that experience like?

Ashley Maguire (Guest): So I had my first taste of that with, I, I'm gonna put startup in

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): they weren't really like a

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): It was a small agency that did like web design for realtors. And did, you know, like, a lot of paper stuff for, you know, like, here's your business card, here's your flyers, things like that.

Ashley Maguire (Guest): So they were kind of like a mom and pop shop. And I started out there as a receptionist and then moved into being the lead developer over

Angelica Maestas (Host): Wow.

Ashley Maguire (Guest): it was a really interesting experience, number one being once again the only woman in the

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): [00:05:00] And, and number two, just having that experience of kind of.

Ashley Maguire (Guest): Getting my feet under me and, and kind of figuring it out as I went along and I realized like, oh, okay. I can do a lot of stuff here that I might not be able to do at a bigger corporation. Like I have a lot more pull. I have like, my opinion matters and people

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): me, even though they usually talk

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): like, whatever.

Ashley Maguire (Guest): I'm still here. But I shifted not long after I had worked there for about three or four years and the, the pay was lower than I wanted and I went, and I, you know, I worked for the government, so I worked for general Dynamics and they gave me a spot as a software engineer. I worked for the National Reconnaissance Organization, so that's,

Angelica Maestas (Host): Wow.

Ashley Maguire (Guest): three letter acronym. Building software for spy satellites, and. I, somebody keeps calling me. Please stop calling me. I realized after doing that job for, you know, about four years, I was like, oh, [00:06:00] I, I don't really like working in a windowless environment. I don't like working on classified materials. Just really doesn't spark joy for

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): So I, I had a very young family at the time that I left that job, and I moved up to Albuquerque and worked at Sandia. And I started working with the renewable energy department and it was like, ah, what a breath of relief. Like I had, was doing something that I felt like mattered and was making the world a better place.

Ashley Maguire (Guest): I was working with really, really smart people. And I still had kind of a level of autonomy that I had had in a previous startup experience, but it still had that, that security,

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): you've got the benefits package, you've got the 401k, you can pay your mortgage and make sure your kid can go to the

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): And it was, you know, at, at one point during the, the four plus years I worked for San DI ended up getting a master's degree. I, I didn't like coding it. As it turns out, I don't like angry crying into my keyboard. [00:07:00] Like, I'm like being frustrated by

Angelica Maestas (Host): You don't like dreaming about code at night?

Ashley Maguire (Guest): No. And, and that was like the moment where I realized like, number one, I'm never gonna be really good at

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): this is, this isn't my passion. This doesn't spurk you away

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): are some people who like, they

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): and that was not me. And I saw it more as like a means to an end. Like I had an idea of what I wanted in place and it was like, can somebody else

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): Can somebody do it

Angelica Maestas (Host): Yeah. 

Ashley Maguire (Guest): And while I was working at Sandia, I found out that user experience is a whole discipline and I ended up going into a master's program at Iowa State, the human computer interaction degree, which is 10 of 10, highly recommend if anybody wants to go to grad school.

Angelica Maestas (Host): Oh, cool.

Ashley Maguire (Guest): I remember the folks in my life were like, I can't believe you're doing that. Why would you go to grad school? Like lots of negative messaging, right? Like. Nobody's paying for this for you. This isn't your job. What are you doing? You're taking on all this debt. And I was [00:08:00] like, I don't care.

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): I'm gonna do this. I did that fully expecting like, I'm never gonna move into that. I'm gonna stay writing code. I'm gonna stay being miserable. 

Angelica Maestas (Host): Like, this is just life. Yeah.

Ashley Maguire (Guest): yeah. It's like, well, you know, all just suffer in our own

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): ways. and then I ended up getting a job at a startup here in Santa Fe called Descartes Labs.

Ashley Maguire (Guest): Right after I got that degree, and it was my first like official startup, and it was right after they had raised their series B

Angelica Maestas (Host): Okay.

Ashley Maguire (Guest): and it was the largest raise in New Mexico history. And so that was how I even found

Angelica Maestas (Host): Oh, so they had stability? Yeah.

Ashley Maguire (Guest): They had stability, they were also trying to do. things for the world. And it also felt like a counterbalance to my original satellite software engineering

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): So it was kind of like working the red in my ledger off, like trying to balance it. So yeah, I, I talked my way into a job there. They had originally [00:09:00] interviewed me for a developer position, and once I passed the coding test, I was like, I don't really wanna code

Angelica Maestas (Host): You're like,

Ashley Maguire (Guest): but I

Angelica Maestas (Host): actually,

Ashley Maguire (Guest): master's degree. did the bait and switch on 'em. but they were

Angelica Maestas (Host): wow.

Ashley Maguire (Guest): it was right place, right time. So I ended up going in as their, you know, the head of design, which is there's a design team of one. So I, I was a UX designer, worked really closely

Angelica Maestas (Host): That's cool.

Ashley Maguire (Guest): the product

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): and with the tech team, and was a really cool experience.

Ashley Maguire (Guest): That was the first time I saw your typical startup. I

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): the. The money, the office, the, you

Angelica Maestas (Host): The chaos.

Ashley Maguire (Guest): Yeah. The

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): the, the kind of unsure about what we're doing, but we're gonna do it and we're doing cool stuff. And everybody was like super smart. I'd never worked with so many smart people before and it made me feel like, oh, I gotta step my game up. Like, like

Angelica Maestas (Host): Level up. [00:10:00] Yeah.

Ashley Maguire (Guest): I was expecting. Yeah. It was really

Angelica Maestas (Host): Well, I think people associate funded startup with. Something that it really isn't like the chaos doesn't go away. It's, it's just now you have milestones that you have to hit because you've accepted dollars and the pressure is on. And so yes, you, you have some degree of confidence. They're not gonna be, they're not going to disappear overnight, like the fledgling startup who's just starting the raise and you just have no idea when they're gonna be out of runway.

Angelica Maestas (Host): So yeah. So you got to experience. Still part of the chaos, which sounds like maybe gave you a, a taste of what to expect when you, when you went out on your own.

Ashley Maguire (Guest): Yeah, it was, it was really interesting because I, I was like in the first a hundred people at Descartes and I don't even know what they got up to, but I mean, I was, I was not even that early compared to other folks.

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): But being able to see kind of on the [00:11:00] ground, the, the, you know, the nuts and the bolts, like that's, that is the wonderful part about a startup is it's chaotic, but a lot of times you get to see stuff that normally you would never be access

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): understanding what the strategy is.

Ashley Maguire (Guest): Hmm. Like, spoiler alert, there wasn't one. And, and you know, kind of watching things as the

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): scales start to. Start to fall apart because a lot of the stuff was improvised, right? It's chaos, it's move fast, break shit, and don't think about how you're gonna scale that into a profitable

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): You don't think about, you know what, what you have to do to hit those milestones and it's no longer just your leadership teams.

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): pedigree as it were. So I ended up leaving Descartes and I went to another startup and they were further along and they had more people and it was in a different space, and I saw a lot of the same things happening, which I was like, what? thought this was just like a weird [00:12:00] but. I was very attracted to the chaos, and I

Angelica Maestas (Host): yeah.

Ashley Maguire (Guest): out of

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): like, no, we can, we can make scalable, repeatable processes and like we can do this

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): right

Angelica Maestas (Host): And they were like, no.

Ashley Maguire (Guest): I mean, some, to some extent I did make really good impacts at, at my second company, not a, not a descarte.

Ashley Maguire (Guest): I didn't really know what I didn't

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): but I took all those lessons learned and went to my other company and. I mean, from day one it was like, okay, cool, and here's some stuff we could do if you want me to do that. And they were like, oh my gosh, this is, this is amazing. Yeah, do it. So I ended up making a pretty significant impact in that company, and I was employee like two 20, and then they scaled up to 600 and, you know, I,

Angelica Maestas (Host): Wow.

Ashley Maguire (Guest): the tech layoffs come for us all.

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): I ended up separating with that company almost, almost a year ago. So it's, it's been a wild

Angelica Maestas (Host): Oh wow. Okay.

Ashley Maguire (Guest): yeah.

Angelica Maestas (Host): So post [00:13:00] exit from, from that company and being a part of those layoffs did you immediately say, you know what? I'm just going to start my own thing.

Ashley Maguire (Guest): so a couple things going at the same time. I was, frankly, I was getting a little frustrated at that job because I knew, like I had the data. To back up like, these are the decisions we need to be making. This is the direction we need to go in. And honestly, like, here, here's what we should be doing to the leadership team with varying amounts of, of success. And I was getting frustrated because it was like, no, no, no. You know, like that's too mature for our organization. We don't need that yet. I'm going, you, you've been around for six years. I don't think you can call yourself like a startup anymore. I think you have to have this stuff in place. And I'm not talking like over the top things I'm talking about. Having a hiring rubric and job descriptions for every role. And it was just, it was a little bananas. So I was getting

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): and my husband who also came from Descarte lab, so, 

Angelica Maestas (Host): Okay.[00:14:00] 

Ashley Maguire (Guest): I gained a husband out of that and also a co-founder, but I'll get back to

Angelica Maestas (Host): Okay. 

Ashley Maguire (Guest): He was like, you should, you know, you're opting out of opportunities because you don't have the business background.

Ashley Maguire (Guest): You have great technical background, but I never took business classes in my undergrad or in grad school, so I didn't understand how finance worked, how accounting worked, how you know, all of that kind of stuff. That was on the other side of the fence from the engineering and

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): I didn't really understand how that worked, so I started an MBA program. which was intense. and I'm almost done. I've got, I

Angelica Maestas (Host): Woo. Woo.

Ashley Maguire (Guest): last chunk of it. I've got like one more thing to do,

Angelica Maestas (Host): Awesome.

Ashley Maguire (Guest): But doing that and getting exposure to all of that and really understanding, you know, how all of these pieces fit together. When the layoff hit, I had already started kind of thinking about like. would I solve this problem if I had the

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): You know, like how would I fix the issues that I'm seeing and, you know, alignment, just kind of high

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): [00:15:00] And so I'd been kicking around this idea of like, what if we built a platform for software companies and it's like, hey, here's how to build a product.

Ashley Maguire (Guest): You don't have to argue about it anymore. Or you don't have to try to like, you know, reinvent the wheel as, as we all want to do as engineers

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): and. I had the opportunity through my MBA program to do a lot of research around it and to, you know, do all your market analysis, your Porter's five forces, your swat, like all of the, the textbook MBA things and put together a business plan for it. it was literally right as that happened that I got laid off and I was like, well, I feel like this is a sign from the

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): Maybe I should just lean

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): My original plan going into the program was like, I'm gonna be a COO. I'm really good at getting shit done. And you know, like, I'd love to do that. And then I, I realized through the program and through my experiences, you know, reflecting back, like the people who found companies, they're not smarter than me. They're not more [00:16:00] educated than me, they're not better at this than me. Like, why am I self selecting out? This doesn't make any sense. So, I, I sat down and talked with my husband and he was basically like, yeah, you should go build this and we'll, we'll figure out how to make it happen.

Ashley Maguire (Guest): It's like, you should do

Angelica Maestas (Host): that's awesome. And that's also not surprising that you self-selected out because as women we do that if, you know, we've, we've got these assumptions in our head of the qualifications. I, I've, I have yet to meet a really qualified founder. I mean, it's just first time founder. You know, you, you, you earn those credentials just by doing it.

Angelica Maestas (Host): And so if you never take that leap, you'll never have the opportunity to build. That was the feedback from your family. How did, so your husband was very supportive. What about the rest of your family? What did they think? 

Ashley Maguire (Guest): Yeah, not a lot of, shockingly not a lot of support there. It was [00:17:00] like, what are you doing? Even our friends, I think were very like, no, we support you, but like, have you

Angelica Maestas (Host): Yeah. 

Ashley Maguire (Guest): Because I should also mention, so my husband was the product manager at Descartes Labs which is how, how we met was arguing over, you know, NPS scores and things

Angelica Maestas (Host): How romantic.

Ashley Maguire (Guest): Very romantic. Yes. Two strongly opinionated people that have lots of overlap. But he had gone on to work at other startups and got so frustrated that right around the time where we got married, he was like, I can't, can't be in tech anymore. I hate this.

Angelica Maestas (Host): Oh.

Ashley Maguire (Guest): he quit tech and went to go build furniture. Loved it. Right? And, and thought it was great. And he was like, yeah, there's no arguing about like, is it a table or not? Like it's a table. And, and it was just, I think a really good experience for him. But I mean, shockingly the furniture building business doesn't pay quite as well as tech does. So Yeah, a lot of, [00:18:00] a lot of the people in our lives were like, what are you doing?

Ashley Maguire (Guest): Like, you just lost her tech

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): But I, I mean, I, I would say I spent a lot, you know, like I spent the first half of my career being really risk averse. I spent the second half of my career with people to make them successful and, and betting on

Angelica Maestas (Host): Mm.

Ashley Maguire (Guest): as, you know, like, oh yeah, like, you've got a vision.

Ashley Maguire (Guest): You, you've got a strategy, you're gonna get us through this. Like, yay, I'm gonna support you. like, you know what? I'm gonna bet on me. And. I, I know what I'm getting

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): and yeah, basically like our retirement accounts and, and just really went all in on Is scary, but.

Angelica Maestas (Host): that is scary, but that is, that is a big part of the commitment, which a lot of founders, the ones that try to dip their toe in and maintain a job or you know, really aren't in it. It it's, [00:19:00] then you never go all in and, and, and part of that is something that people can see and hear it in your voice that, you know, when you talk.

Angelica Maestas (Host): You're invested. That's a huge sacrifice, a huge degree of risk, but you're doing it for the opportunity for a huge reward. But I would, I would love to hear a little bit about the, the journey in the co-founder selection process. How, how did this person emerge? You said you worked together before.

Angelica Maestas (Host): How did you, 

Ashley Maguire (Guest): did.

Angelica Maestas (Host): this happen? What was the conversation?

Ashley Maguire (Guest): that's a good question. People, people always ask like, oh, is he your husband, your co-founder? And it's like, I love him so

Angelica Maestas (Host): That I would never,

Ashley Maguire (Guest): no. Like we can't work together again. Or at least not in the

Angelica Maestas (Host): yeah.

Ashley Maguire (Guest): before. so there. There was a lot of really smart people at Descarte and there are still a lot of really smart people at Descarte.

Ashley Maguire (Guest): I just, you know, I don't work there anymore, so we had created this like Slack channel for alumni. You know, the people who

Angelica Maestas (Host): Oh yeah.

Ashley Maguire (Guest): can, you can join this alumni Slack [00:20:00] The lead engineer, his name is Justin, and he, he and my husband and I all worked really closely together on the platform at Decart. I remember, you know, saying to my husband, like, oh my gosh, if I could have like two engineers like Justin, I, I wouldn't need 15 engineers to get this bill. Like I could

Angelica Maestas (Host): Oh

Ashley Maguire (Guest): it with two. 'cause he's so

Angelica Maestas (Host): yeah.

Ashley Maguire (Guest): and he's so focused and, he's not, you know, he doesn't develop things at the expense of tech debt later on, or, you know, this is good enough for now or without documentation, which is what

Angelica Maestas (Host): Wow. Oh yeah.

Ashley Maguire (Guest): And you know, no shade, like you gotta get stuff built. I get it. But he was always very methodical and thoughtful about like, you know, future proofing things and making sure things scale over time and what is gonna be the best outcome. And just brilliant guy. And I remember thinking, you know, when I was first putting this together, like. You know, I could build this by myself, but it would be really nice to have a technical

Angelica Maestas (Host): [00:21:00] Yeah.

Ashley Maguire (Guest): And at first, I, I got some feedback that was basically like, Hey, if you are gonna raise VC funding, you need a co-founder. And I was like, but why? Like, I have the business degree, I have the engineering background.

Ashley Maguire (Guest): I, I could build it myself. and also like, oh, by the way, you're a

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): like, you should really get a

Angelica Maestas (Host): Mm.

Ashley Maguire (Guest): I mean, frankly is

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): why do I

Angelica Maestas (Host): Yep.

Ashley Maguire (Guest): Sure it's sharing the load and all of those things. And also like mitigating risk for the investors. I get it like at a cerebral level, but also

Angelica Maestas (Host): Still bullshit. Yeah.

Ashley Maguire (Guest): Yeah. Like that's dumb. That's dumb when you make

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): When I was thinking about, okay, like do I wanna find a co-founder? Do I wanna apply to Y Combinator? Do I want, you know, like, do I wanna do any of these things? all of this is floating around kind of jingling in my head and Justin posts. the Slack channel, the alumni

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): he's like, Hey, kind of bored my job. If you guys see anything cool, let me know. And I was like, oh, it's a

Angelica Maestas (Host): Oh,

Ashley Maguire (Guest): from the [00:22:00] universe.

Angelica Maestas (Host): wasn't he at Google?

Ashley Maguire (Guest): he was, yeah.

Angelica Maestas (Host): Bored at Google. 

Ashley Maguire (Guest): I, yeah, I mean, that was kinda

Angelica Maestas (Host): Yeah,

Ashley Maguire (Guest): just like, bro, how are you bored at

Angelica Maestas (Host): yeah,

Ashley Maguire (Guest): but he's just a super smart guy and likes to tinker with stuff and, you know, likes to, to do new things.

Ashley Maguire (Guest): So I, I don't blame him and. immediately went to Connor and was like

Angelica Maestas (Host): yeah.

Ashley Maguire (Guest): and was like, oh my gosh, Justin's, Justin's bored. Do you think you would do this? And he was like, why don't you ask him?

Angelica Maestas (Host): You're like, oh yeah.

Ashley Maguire (Guest): I was like, oh yeah. Like I, I can use my words. So I reached out and asked, you know, like, Hey, would you be interested in, in doing a startup?

Ashley Maguire (Guest): Like, I, I have this idea and I'd like to get your feedback on it. And I had had a lot of. People in my life, you know, once I explained what we were building and what the point of it was, they were like, oh, okay, I see the value. Like, I get like, I don't know how you're gonna do it, but like, I get, I get what you're

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): I understand the value. And I was like, maybe they're just being nice, you know, maybe this is a really [00:23:00] stupid idea and like it's gonna fail. And then I, I sat down and in my very jumbled way, it was, I felt like the, the, it's always sunny meme with like the. Like the red string. And because I had like Figma files and like doc file, like I had a lot going on.

Ashley Maguire (Guest): It was not organized. And I sat to him and explained it to him the best I could and he was like, oh yeah, I get it. Yeah. Like that's not just a startup problem. Like we have that problem at Google. And I was like, 

Ashley Maguire (Guest): Oh, okay. I've got some social proof here that like, this isn't a dumb

Angelica Maestas (Host): yeah.

Ashley Maguire (Guest): you know, oversimplifying this. is the most brilliant engineer I've ever worked with in my career. And he also thinks this is a good idea. Oh my God. I was like, Hey, well what do you think about being like co-founder or CTO? And he's, he's a very kind, very quiet, like if I'm an introvert, like

Angelica Maestas (Host): Okay.

Ashley Maguire (Guest): don't know what the next level is, but that's, that's Justin. It took him a while to kind of, you know, say like, oh yeah, like I'm on board with [00:24:00] that and.

Angelica Maestas (Host): Probably with a,

Ashley Maguire (Guest): then we just

Angelica Maestas (Host): that level of enthusiasm. Yeah,

Ashley Maguire (Guest): yeah. He's very like, just stoic and I love that because I'm not that

Angelica Maestas (Host): yeah.

Ashley Maguire (Guest): and it's just, it's

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): So yeah, he was on board and we started building almost immediately, and it's. It's been a really fun experience. I tried to stay outta the code as long as possible. I was like, I'll just leave that to him. He's, he can do it

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): And then I was like, maybe I wanna do a little bit. So I, I started tinkering around and, you know, making support requests

Angelica Maestas (Host): nice.

Ashley Maguire (Guest): getting back to my

Angelica Maestas (Host): Yeah. Well, I love that the the co-founder emerged and, and it wasn't something that you had to go enforce, which sometimes, especially female founders in tech feel they have to because of the bullshit reason that you need a dude, but yours just emerged. So I, I love that that happened. I think it's affirming that you're on the [00:25:00] right path.

Angelica Maestas (Host): Can you tell us a little bit about where you are now on the journey and, and even the name? 'cause I don't think, I, I don't think you've told me.

Ashley Maguire (Guest): So the name of the company is Helen's Foundry. And I will get into the, the etymology 'cause everybody's like, who's Helen? You're not Helen. It's like, yeah, I know. It's a marketing ploy. It's not. I just, I really like the

Angelica Maestas (Host): Okay.

Ashley Maguire (Guest): But we're currently building out we went through the Cornell Accelerator this summer for startups which was a really cool

Angelica Maestas (Host): Okay.

Ashley Maguire (Guest): We pitched to New York City. We've done a couple of like pitch type things. We did a friends and family round and we're basically deciding to bootstrap for the most part.

Angelica Maestas (Host): Okay.

Ashley Maguire (Guest): challenging to, to explain the value I'd say of a, a platform like this to investors who haven't been operators. They just don't immediately see the value.

Ashley Maguire (Guest): They don't immediately see the problem.

Angelica Maestas (Host): Fair.

Ashley Maguire (Guest): And when you talk to operators, they're like, oh my gosh, when [00:26:00] can I have it? So we've, we've been building based on our own dog fooding. So we've been using our own stuff and making updates as necessary. And we've got a couple of beta testers, but we, we have a waiting list of folks.

Ashley Maguire (Guest): We don't wanna put out a product that doesn't solve problems for

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): We want an enjoyable product, not a minimum viable one. So that's, that's kind of where we're

Angelica Maestas (Host): Okay. 

Ashley Maguire (Guest): But we are in talks with a couple of angels and, you know, individual investors both here in the US and in Canada. so yeah, it's,

Angelica Maestas (Host): Okay.

Ashley Maguire (Guest): really well.

Ashley Maguire (Guest): There's still a lot of stuff I want to build that we're gonna build. It's just a matter of velocity at this point. You know, how much, how much money kind of dictates how fast we can go.

Angelica Maestas (Host): Okay. Well, I mean there's a lot of value to the bootstrap model and venture isn't. Always for everyone, but I think the benefits of pursuing it when you're ready and have established some degree of traction are, are all a benefit to you and your co-founder because of the equity stakes.

Ashley Maguire (Guest): Oh yeah,

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): [00:27:00] And you know, we, we did see that at. Some of the startups I've been at is once you get on that, that hamster wheel, that treadmill, whatever, you know, an outlet you want to

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): for venture, it's very challenging. And I think especially a lot of the companies that took a ton of funding, when, you know, we had zero interest rates and all those valuations went to the moon, like you're not gonna be able to reach the valuations that you had then.

Angelica Maestas (Host): Right.

Ashley Maguire (Guest): of unicorns lose their unicorn

Angelica Maestas (Host): Yep.

Ashley Maguire (Guest): and. not necessarily through any fault of the organization, but it's mostly like, yeah. And there were some pretty heavy strings attached to some of that cash. So,

Angelica Maestas (Host): Yep.

Ashley Maguire (Guest): you know, we'll see, we'll see who makes it out and who doesn't, but

Angelica Maestas (Host): Right.

Ashley Maguire (Guest): I always am suspicious of, of taking money and it's like, no, no, no, it's just free money.

Ashley Maguire (Guest): And it's like, it's never just free

Angelica Maestas (Host): It's expensive money.

Ashley Maguire (Guest): Yeah. It's very, and, even thinking about fundraising and like, going through all of that, like, it just takes so much

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): And it pulls so much

Angelica Maestas (Host): [00:28:00] Exactly.

Ashley Maguire (Guest): And right now I really just wanna focus on building a product that is useful for people and provides

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): and not, being a cool guy, CEO,

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): know, going to mixers and networking events and rubbing elbows, like, I mean, those are good things and it's good to build out the community and to provide value for people in the community.

Ashley Maguire (Guest): But once again, it's like you gotta

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): actually building

Angelica Maestas (Host): Yeah. Well, I mean, there's only so much of you to go around, and especially if you already have beta users, you've got the ability to establish, well, one is to collect the feedback and really know that you're on the right path and building a great product, but. It would be a huge distraction to go down the, the venture path when you are so focused and already have some traction.

Ashley Maguire (Guest): Yeah, for sure. And so back to the name Foundry, like what does that mean? I got into my Greek mythology phase way later than most girls.

Angelica Maestas (Host): Oh,

Ashley Maguire (Guest): do it as a

Angelica Maestas (Host): oh,

Ashley Maguire (Guest): I, I got into it as an

Angelica Maestas (Host): [00:29:00] oh fun.

Ashley Maguire (Guest): and my husband studied, studied the classics in his undergrad. He went to go get an education and he was like, you should name your startup the Greek word for builder.

Ashley Maguire (Guest): And I looked it up and I was like, I don't know how to say that. Nobody's gonna remember that. Like, that's not, that's not

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): like, okay, but your, your tagline could be. software that launched a thousand startups. And I was like, that's a good

Angelica Maestas (Host): Oh,

Ashley Maguire (Guest): but wouldn't that be Helen? Like, she's the one who launched a thousand ships.

Ashley Maguire (Guest): Like,

Angelica Maestas (Host): oh.

Ashley Maguire (Guest): not? So I, I really liked the idea of using Helen and her imagery and

Angelica Maestas (Host): Oh, I love that.

Ashley Maguire (Guest): you know, Helen is helpless and things are dumb to Helen, and she's just a pond. Like, no, she's, she's our leader now. And that combined with the, the foundry model of. Some entrepreneurship programs in higher education where it's similar to a tech transfer.

Ashley Maguire (Guest): You know, you, you work with folks in higher education and then they help you spin out successful business and commercialize it. And I just thought that was a really cool [00:30:00] idea that the idea of a foundry. And so Forge is the name of our platform 'cause we help

Angelica Maestas (Host): Oh,

Ashley Maguire (Guest): all of the, all of the things you need to build a successful software company.

Angelica Maestas (Host): awesome. I love it. That would've been my second guess to how you got to the name. No, just kidding. I had no idea.

Ashley Maguire (Guest): It's a good talking point, please.

Angelica Maestas (Host): I love it. Yeah. Alright, well thank you for sharing about the journey. I am. I want to now ask you some very serious questions. Dream vacation, destination,

Ashley Maguire (Guest): Costa Rica.

Angelica Maestas (Host): margarita, wine or mocktail.

Ashley Maguire (Guest): Mocktail

Angelica Maestas (Host): Most used app.

Ashley Maguire (Guest): Instagram, I shouldn't say that, see their Instagram or Twitter?

Angelica Maestas (Host): Oh, you gotta be honest.

Ashley Maguire (Guest): Yeah.

Angelica Maestas (Host): your entrepreneurial journey had a theme song, what would it be? 

Ashley Maguire (Guest): That's a good one. You should see [00:31:00] me in a crown by Billy Bish, Eilish,

Angelica Maestas (Host): Oh, okay.

Angelica Maestas (Host): Yeah, A favorite self-care ritual after a long day.

Ashley Maguire (Guest): Taking a

Angelica Maestas (Host): Oh,

Ashley Maguire (Guest): Oh my

Angelica Maestas (Host): me too.

Ashley Maguire (Guest): and my cat, my cat likes to hang out in the

Angelica Maestas (Host): Really?

Ashley Maguire (Guest): Like that's his, yeah, he's very

Ashley Maguire (Guest): Oh, I thought they'd be scared. normal cats are, yeah, 

Angelica Maestas (Host): Oh, and last but not least, what can our listeners do to support you?

Ashley Maguire (Guest): I am just really happy to connect with anybody else in this space who's trying to build something or even just thinking about building something. I think there is a, a, a community out there of people, and especially to other women in tech, other women in entrepreneurship or considering it like. Let's talk, like, I wanna help

Angelica Maestas (Host): Yeah.

Ashley Maguire (Guest): give you support and be your, you know, your sounding

Angelica Maestas (Host): Mm-hmm.

Ashley Maguire (Guest): Me wrong, I, I also like tracks. If anybody is willing to be an angel, that's fantastic, but it's really more about I wanna support and give back to the community [00:32:00] and the way that they've supported me and connect people where I can to, you know, useful and valuable resources.

Ashley Maguire (Guest): And other people.

Angelica Maestas (Host): Great, and should they find you on LinkedIn.

Ashley Maguire (Guest): I'm on LinkedIn. Yes.

Angelica Maestas (Host): Alright, well thank you for being on Ashley. It's been wonderful.

Ashley Maguire (Guest): Thank you. ...

Angelica Maestas (Host): and that's a wrap on another episode of She's Ambitious AF. Remember to dream big, hustle harder, and show the world that when it comes to success, we're not just ambitious, we're Ambitious AF.