S1EP03 - Listening to Your Gut with Lisa Hillyard

This is The Capital Flex. I'm Naseem Sayani. This show codifies the capital playbook because no founder should have to learn the hard way. We talk about what really happens behind closed doors, the bias, the breakthroughs, and the things no one says out loud. If you've ever walked into a room and felt the system wasn't built for you, you're in the right place. Hello and welcome to this episode of The Capital Flex. Today, my guest is Lisa Hilliard. She is the co-founder and CEO of Milo Human Care, a company pioneering regenerative economics in skincare. Uh, it's fabulous. I've known Lisa for a little while and I've seen what she's trying to do to really reimagine the category of CPG. Her background comes from advertising technology and executive leadership, and she has built Milo to prove that profit and social and ecological change can coexist. When companies take responsibility for doing so. And I'm a strong believer in the same thing, is that we don't have to choose one or the other. So that's why we're good friends. Thank you for being here, Lisa. I really appreciate it.

Yeah, happy to be here. Thank you so much for having me.

For everyone listening, please introduce yourselves just a little bit more and tell us a little bit about your company.

I am the co-founder and CEO of Milo Human Care. We are working to rebuild the CPG industry through regenerative values. We see the beauty industry and then more broadly the CPG industry as one of the most problematic when it comes to the issue of overconsumption. And in our perspective, overconsumption itself is one of the biggest issues that we have in society today. That's kind of leading us to this hellish landscape of late-stage capitalism that we find ourselves in today. And actually, I'll add, I am— one thing to add to the bio is that I am a newly published author. We just released a book on corporate dynamics called On Behalf Of, kind of through the lens of the executive assistant role, really exploring how we choose our leaders, why we choose our leaders, and looking into whether we should maybe flip it and start to, to look at different qualities for leaders to get to better outcomes that are more equitable.

Oh, that's incredible. Congratulations. That's exciting. So as you know, the, the foundation of the podcast and the reason I wanted to do it is that I hear all kinds of fundraising stories, uh, from the women in the venture space. And some of them are great cuz they secured the check. Check, but the vast majority of them, uh, have some kind of, uh, unfortunate adventure and it's, it's bias, it's bad behavior, it's all the different things. And what I want to do is really start to talk about all of that out loud and codify the stories, talk about the learnings, and really help this be a series where any other founder who listens to the episode starts to have a bit of a toolkit and a set of learnings before she walks into her fundraise. Uh, and so before we jump into your stories, because I know you have a few, how would you, how would you characterize your fundraising experience overall? If you had to pick 2 or 3 words.

Disheartening, I would say illuminating and ultimately empowering.

Okay. Well, that's good.

Ultimately.

Ultimately. Right. Okay. Well, that's good. Tell us a little bit more about those 3 words.

Yeah, for sure. So, I mean, I think coming from an executive role, coming from Being, it was service, it was a service business, it was an agency, but serving CPG brands, the ones that we're like competing against now, really being pretty deeply entrenched in that like space globally. I thought it was gonna be way easier for me. Way easier. Way easier. Like half of that was probably naivete and the other half, I still don't really know what to say. I mean, I'm not, I'm not. Pitching a duplicate of what I know before. It's, it's like a, it's a different thing that we've, we've put together. But I think that was like, so first of all, like big shocker. Okay. Like the, the capital you had has no value here. Even though there was like VC involvement in my past work, it is what it is. It was more tech. So, you know, once the vertical changes, everything kind of changes. And then over time, just like having conversation after conversation where I think a lot of founders go in. Feeling the hierarchy, feeling like there is somebody to present to, somebody to pitch, somebody to impress.

Yeah, there's a power dynamic, right? Right out of the gate.

100%. 100%. And if you haven't done a certain kind of like mental work, you might mistake their criticisms for you being wrong. Right? And it took some time. It, it took some time for me to navigate like, okay, that's fair criticism. I think I should. Consider that in our case versus, oh, they just don't get it and they just have a different perspective. And that's okay because they've got their investment thesis, which they're entitled to. They've got their LPs to serve, which is, we know that's how it is. Nevertheless, we're building what we're building and we're going to do it anyway. And I think that that's sort of like the illuminating part of unpacking the hierarchy, unpacking what it was in me and in my co-founder Katrina that was making us feel like, oh, like are we doing the right thing? When it comes to like empowering that third word, I like the way you frame it with the different, like different words that I can kind of like explain that as the final phase of recognizing that in our particular instance, and I don't think that this applies necessarily to like every woman-led startup, we're doing something really specific within like the regenerative space. We're essentially trying to build our own regenerative economy with Milo Human Care. Like we're launching with a, a singular brand, but the, the plan is a venture builder and then to become What L'Oréal is today, that's who we plan to be maybe in like the next 10 years. And in the next 20, we want to start eating their lunch. That's kind of like how we, how we—

big vision. Absolutely.

Yeah, exactly. And, and so that's a big vision to sell. And what I came to realize is that the way the conversation that like CPG VCs wanna have is one of unit economics. And if you, and, and we actually do have good unit economics, but that's not the business. That's not what we're interested in. That's not what gets us excited. And so what we're raising and what we're planning to use it for, it looks different than what a typical like beauty brand, skincare brand pitch would be. And that out of the gate was just almost like a nonstarter. Somebody early on, like really early on in like the advising stage of fundraising, you know, when you're asking everybody that you know for any advice, The advice he gave me, and he's been really successful, he's raised like multiple, like double, double-digit million, like rounds for his startup. He said, VCs are herd animals, present company excluded, for sure.

Appreciate that.

But I've, I've come to realize that that's actually mostly true. The, what's like the current bubble.

Yeah.

Well, right now it's AI, it's generative AI, like, okay, well, let's. Put all the money into like as many of those as we can. Like, what are the models we're familiar with that have succeeded in the past?

Yeah.

Especially right now. Like, I mean, we, we started sort of informally fundraising right around like 2022, I would say, 2023. And the economy was just so tough at that time. Like, we're essentially asking in our model for like a patron of the arts. As far as like a VC is concerned. And so recognizing that and just wanting to say, okay, we're going to just figure out a way to do it ourselves. That was the empowering part. Sorry, I took a long path there.

No, it's great. It's great. It's really interesting because I think there's that last part, right? There's something very— the difference between the VCs, because I've seen this also, right? The VCs who— simplifying it— the party rounds where you've— someone finds a great company and everybody runs after that company and you You know, they, they follow signal from other people and that's how they invest. And then there's VCs who build true individual conviction and they have a point of view on the future and they see where it's going and they want to back companies that are part of that future. And those are very different VC profiles and I've seen both. Uh, and it's really interesting to see their investment behaviors. I personally like to believe I'm in the second camp. And I build conviction and I know why I want to invest and I know where these companies fit in the future. And then that's why I write the checks I write. And, but there, I've seen the ones that do the other thing. It's also why B2B SaaS is such a big driver of so much money and it's why people running after lots of AI and they're running after crypto and they're like, it's, it's driving so much capital one direction. Where yes, sure, there's, there's alpha there, right? But there's all these other categories that are transformational that also have alpha, but it, it's taking longer for the money to get there. And it's how do we drive the conviction in those places unless we put more people have a point of view and say, no, it's over there. Let's go put money over there.

Yeah. Somebody to say, no, we like, the world doesn't need another 10 SaaS startups, right? Because it's what the, the issue that I find in like going into, you know, the, this idea that, or that this statistic actually, it's not an idea, that women get 2% of all funding that's available. If the paradigm changed and we stopped this whole like, gotta invest in 10 for 1 to win thing, then maybe we would stop investing in so many useless, like copies of a copy, like AI agent startups or whatever. You know what I mean? Like it, it boggles the mind.

Yeah. Oh, absolutely.

My mind. At least. I don't, I don't understand it. I really don't get it.

It's like a small sidetrack, but we're having constantly having conversations in the women's health world that I live in about like really getting more capital behind the companies that are laying new, like reimagining women's health, right? Healthcare for women, if we have to say it differently. And the prop— some of the reason why we don't have enough of the bigger funds putting capital here and we're still having trouble getting the Series A, B, C rounds funded for these companies is because there aren't any exits yet. We don't know if it's gonna work. We, we don't have the data points. And you kind of look at them and you go like, that doesn't make any sense, right? Because you're running after crypto. We don't have major crypto exits. We've also seen major failures, major SBF, major failures.

And yeah, like huge, huge.

And yet the money is still going there. So this is, it's a false start to say that that's not a real answer to say that we don't have the exits in women's health. And so that's why we're not putting the money there. Like that's, that is not the reason. There's some other reason that the money's not moving.

Oh, I wonder.

No, I know that's a whole different podcast, but like it's these, but isn't it, it's frustrating when you realize that's fundamentally the answer, right? Right. Yeah, absolutely. This episode is brought to you by Care Beauty. The first pro-aging skincare line designed for women over 40 by women over 40. Founded by two beauty industry veterans, one of whom worked with icons like Elizabeth Taylor and Halle Berry, Care is the only skincare brand using patented science to counter the skin changes caused by hormone decline. So if your skin feels drier, duller, or less firm than it used to, it's not just aging, it's biology, and Care is the solution. Visit carebeauty.com to learn more. That's C-A-I-R-E beauty.com. Because it's not anti-aging, it's pro-you. So I know you've had some really interesting things happen in your fundraising story and journey. So take us, take us through the, the one that I know you talked about on LinkedIn. Take us through that story and then we'll go to one of your others.

For sure. So, it was a, like somebody kind of put my deck in front of a few people. One reached out directly to me basically right away, and I was so excited because it was a guy who leads the, what they claim is the first ever gender lens investing firm.

Okay.

So I'm like, oh my God, that's totally us.

Yeah. Sounds perfect.

Perfect. If you, if you're, if you're literally just investing in women and that's your premise first and foremost. Like, let's talk for sure. So we have a meeting. Great. We like, it, it all seems fine. I do some research. There's some like weird, like past PR flags and stuff. And I'm like, ah, you know, it's 20 years. Like people can change. Right. So I go to dinner with him. That was our first in-person meeting. The first call we had was myself and my co-founder Katrina and him. And then we like hit it off. It was good enough. And then I had dinner with him here in Toronto. Where I, where I live. Nice restaurant, really nice restaurant. And it's so, any, any, anyone who's been in like corporate and has worked in male-dominated environments, like any woman, I would say, has some experience with letting things just sort of like roll off your back.

Mm-hmm.

You know, like if you're, if you're encountering, if you're encountering a man of a certain age.

Mm-hmm.

And of like a certain singular, often. Cultural background, you're gonna, you're gonna come to expect, like, you, you just start to give them a discount if you want to survive in, like, the corporate world, right? And I, I got very used to giving that discount in the work that I was doing. Like, sure, I said, I said CPG and beauty, but also automotive. Like, automotive is grossly male-dominated and, like, very misogynistic in the thinking, such that it's, like, just baseline. It's like normal. And so when I, when I go to dinner and, you know, the, the waiter is making comments about me to him and he is playing off of it about like, oh, what a nice dinner companion and blah, blah, blah, blah, blah, like, oh my goodness, right? And when you tell other people that story, you're like, you're already like, wait a minute, there's a lifetime, Naseem Sayani, a lifetime of conditioning inside of me that has, has adapted to freeze and/or fawn in those situations. And so throughout the course of the dinner also, I mean, I, I mentioned this to you before, I lost my partner about almost 2 years ago. And when we met, it was like almost a year ago. So it was like quite fresh. I was still, we also worked together, so there was just like a lot of vulnerability around the whole thing. And it almost just felt nice to be going out to a business dinner. For the first time in a super long time, it just felt like getting back to normal.

Yeah.

And so I embraced that with open arms and I was honest about like my last experiences. And I don't know if he took that as a sort of like, maybe, maybe there's like some, some questionable, like, I don't know what, but he felt empowered or he felt allowed to just be inappropriate, to, to say things that were offside. I mean, I, it's hard to remember like all the little things, but just that like dynamic with the server. That was like when I sat down, like when he sat down, I was there first, like when he sat down and when he arrived and it didn't stop for the whole night. Right. And it's like, well, am I a dinner companion or am I, am I like a founder and you're a VC? Like, are we having a dinner? Like, are we having a business meeting? He insisted on walking me home, which was like another thing that was like, not, not my favorite idea, but again, like, I don't really know how to like get out of that. Like I'd already disclosed where I lived. And so, which was like, it was super close. Right. Like, oh, like I walked, it was super close.

Was it in the context of safety?

No.

No. Okay.

Also, sorry, but if it was in the context of safety, like, I'll let you know when I feel unsafe.

No, right. Of course.

You know what I mean? Like, even if, yeah, no, there was no, it was, he just wanted to and he was walking downtown anyway. So he is like, oh, or like, I, I'm gonna walk, I'll walk from your place and then I'll call an Uber or something. And it's like, well, this isn't a date. Like, that's literally what guys do when they take me on a date. Right.

Like, right. Then they'll walk you home.

Literally, if I want them to, but it was a business meeting. So like that on its own was just like weird, but we did have good conversation in between those moments about how women need to be empowered, how he, you know, his mother was very strong and he really believes in women and he's seen like, whatever, whatever. To be saying those things in the same meeting where you're behaving that way is, is really like confusing and jarring. And at that time, like those really early stages of just starting to fundraise more formally. And so it's like, okay, well, I mean, if this is the game I'm entering, this is the game I'm entering. Let's see. So I agreed to have a follow-up meeting, like maybe a week and a half later for, for lunch. Maybe to the outside observer, I should have just not participated in anything further, but. I, it wasn't like I wasn't there yet. And then, so, so he asked me to lunch. We had lunch again, nice place, Four Seasons. And over that lunch, he was just like way more explicit. So I guess I, I'd mentioned that I lived in Berlin and, and worked there, and he chose to make that a conversation about how like European women are a lot less I guess like prudish is a word that he would've used, not a word I would use, but a word he would use when it comes to what they do. Like, you know, from 5 to 7, like 5 to 7 style. So, and, and, and chose to tell me that when he goes there, cuz he's traveling all the time cuz he's an international businessman of, of some renown, right? The, the, the founders there that he meets with just proposition him like out of nowhere.

That the founders proposition him. No kidding. Really?

Yeah. Even the married ones.

Really?

And this is what, and I'm not like, I'm not, I'm not reporting facts. I'm telling you what he said.

Yeah. Yeah. Yeah. So, and this is still in the context of him potentially investing in your business.

Yeah. Yeah. Yeah. Yeah. Like, yeah, we're still like, I mean, I'm not, I'm not a great linear storyteller. Right.

So like imagine this conversation, the umbrella we're under is still the context of investment.

The umbrella is 100%. There was never at any point, any indication whatsoever from my side, verbal or nonverbal, that I was in any way interested in this man. So imagine the conversation as like bouncing between life stuff, business stuff, inappropriate remarks, and then back around again, right? Like it's just that kind of, and that's who I am in business, right? Like I'm just a person and we're gonna talk. So also some of it feels somewhat normal in terms of like how I relate to another person, but the The things that he's saying are deeply inappropriate. And so the, the kind of like crescendo of it all was when he literally said to me, if there's ever anything that you wanna talk about, like, I won't, like, I don't have to tell my wife who he works with, by the way. Like, she's, she's like inside. Oh, they work together. Okay. Fund. Yeah, yeah, yeah. So many questions, right? Like, okay, first of all, what, what dynamic do you think that we have that we need to have a secret from your wife?

What am I going to tell you?

Or anybody?

Or what are we going to do that you're not going to tell your wife?

Yeah, right? Like, like, what are you talking about?

Oh my God.

So, and, and that, this is, again, like, this is not even like my 10th story in business like this to some degree, one way or another, right? Like, this is just, this is the way.

When did you kind of stop it all? When did it get to a halt?

So the lunch finished and we agreed to next steps. Oh, oh, okay. I feel this is important to mention because to me, cuz then it's like, is this whole thing just a shell game? So he like had gone through some stuff allegedly and was like rebuilding allegedly. And part of the, and that's what this new fund was meant to be allegedly. So it was an interesting structure of he takes board seats that he gets paid for, or like advisory seats that he gets paid for, or I think he makes money also, like if he finds other investors. The idea is he writes, or actually he doesn't even write a check. He writes an LOI for $50 grand, cuz that's his ticket size for all of this like grandiose, like supporting women thing. $50 grand is the ticket size. What he really wants to do is give an LOI that he's the lead investor to get other investors.

Okay. But he hasn't moved any money yet?

No.

Okay.

And, and, and said to me like, but you're okay if you get the money a little later, right? And then that's automatically, it's like, okay, you can be a dirtbag, but if you think that I'm that dumb, then I'm going all the way for the jugular. All the way. Like, how dumb do you think I am?

The money will never come.

Even beyond that, the, the idea that worthwhile other investors are gonna take seriously this guy who can't even write a $50,000 check and he's like the lead investor. Right.

It's not a big enough lead check. That's not a lead check.

No, that's my point. That's my point. It's not a lead check.

Yeah.

And I don't get the sense that he would pass like whatever checks it would take to like verify that, you know, he would eventually disburse the funds. So it's, it's, it appeared to me to be a little bit of a shell game of getting entrenched in these companies, having backend deals either with like, like because of advisory, like stipends or because of whatever kickbacks on, or commissions or whatever you wanna call it, on finding investment and using that to finance the, like the checks that he would eventually write.

Oh my gosh.

Yeah. So like, that's what I say, like it's literally a shell game. Like tell me that's not a shell game.

Yeah. No, that's crazy. I help you find other investors. Yeah. I get a fee on what they invest and then I pull that money and that's how I fund the $50K that I eventually give you.

That was my understanding. And I'll admit it's been, it's been a year, but I'm a nerd for like the mechanics of the deal.

Sure. Of course. No, it has to make sense. And if it doesn't, it doesn't.

Right. And so like when you, when you tell me something like that, like I'm gonna remember at least the core points of it. So like, okay. If somebody identifies themselves through what I'm saying and feels that that's wrong and I'm incorrect, maybe, but that was my takeaway. So then there's like another super like insulting aspect of it. Which is that then he has this like stable, and I'm using that word very intentionally, of women founders that he calls his like advisory council or something like that. And then he's giving you this kind of like fake PR prestige of being on this venture fund's like advisory council where you can then advise some of his start— like other startups that he's like investing in. And at a certain point, some of those like things could be like regeneration, that those could be like regenerative values coming to life. But if the essence of it is preying on like the, the most disenfranchised individuals in the fundraising space and not even writing the check fast.

Oh geez. What in the world is going on?

And be like sexually harassing people in the meetings. Like, what are you for? Like, at least, at least if I go and do a tour in Silicon Valley, I'm gonna, I'm gonna hear a lot of shit, but they are, like, ultimately a meet, a real meeting will take place, and like, some text will be written or not based on, like, real things, I think. This is just, like, insulting all the way around is how I would describe it.

Oh my goodness. You think that these things don't happen, but they absolutely do. They absolutely do.

Also, who thinks that they don't happen? I've never thought that they didn't happen. I've only ever experienced that they do happen.

No, I know. We hear these things all the time, which is the purpose of the podcast is to talk about these things out loud and, and 100%, which is so appreciated. Yeah. So then what, where did you get to the point of needing to put a stop to the whole conversation? And then the LinkedIn post and the story you talked about on the, like, take us through where it ended. Yeah. And ultimately you called him out. So what happened?

So I left that lunch being like, am I in the fucking Twilight Zone? Like, what is going on? Like, I don't, like, I don't know. Like, I feel weird and like, I don't know what to do. So I call Katrina. I think he's bullshit from a business perspective, first and foremost. Like, he's bullshit from a business perspective. He doesn't have anything that can help us. And so, like, off the table. Separately, that whole dynamic of, like, how I felt about some of the things he said. I think I did tell Katrina, like, as, like, right when it happened, what he said, maybe. But it took me some time to really internalize that over the course of dinner and lunch so much inappropriateness had gone on that there was no way I couldn't say something about it. Yeah, there was no way. And so I felt, and I think this is part of the cycle of these types of experiences too, is that like the shame part where you're like, fuck, like, what did I do? If my friend told me this story, I would tell her like to walk out of the, the dinner, let alone making it to another lunch. And, you know, and what did I invite in that discussion?

We're conditioned for that, right? We're conditioned to take the burden as us.

100%. 100%. Yeah. I hate to say this because it like feeds into a narrative, but that I reject. But also like, was I dressed too much like it was a date? Like, was it, you know, whatever. When, when actually like I have one look and it goes with me everywhere and I don't change the way that I look for the settings that I'm in because I don't— that's not how I show up authentically. So like if somebody has a problem with how I'm dressed or chooses to perceive something about me from that, that's gonna have to be their problem. Like I'm not gonna change it. But the question did come up, like, was I, like, should I have put less effort in? Should I, like, you know what I mean?

Like we start to question everything.

Yeah, exactly. And then, and then it's like, well, should I have told him not to say that? Should I have gotten up and left? Like, what are all the things that I didn't do? And in the post on LinkedIn, I did actually. Say that, like, I have to acknowledge that like things happen that I intellectually knew were not okay, but I just didn't have it in me to like deal with it. And fight or flight is what everybody talks about, right? But there's two more known as freeze and fawn that are really, really common in situations like this. That where, where freeze is like, you're, you're like dissociated basically. You're just like, you're, you're, it's like that thing where you're like looking at your body, like interacting and you're just like, I, I just have to do what it takes to like stay here and like keep this normal. Like keep it, I guess, from escalating. Like just keep it how it is. Or you fawn, which is like, okay, well if I'm nicer, if I'm like, if I feed into this, then they're not going to turn on me.

It doesn't get worse.

Yeah, exactly. And, and those are, those are dynamics that people don't talk about enough and in much larger kind of like survivor narratives, there's this constant discussion about like, well, that's not how somebody would act if they were abused. That's not how somebody would act if the, the person was really inappropriate in the moment. Like, that's not what they would do. And you find out yourself that even across different situations with different people, you, your, your survival instincts are accessing different elements of that.

Yeah. No, absolutely. Yeah.

So I, I, I think that that's like important to, to acknowledge, but anyway, so it took me a few days. Katrina and I kind of went back and forth also as to like, what is it to be a women-led business fundraising who also insists on standing up for what's right while also knowing that like alienating people in the business world is maybe dangerous. And fundamentally, I, I, I just ultimately decided I had to first of all confront him. Secondly, speak publicly about it because I was recommended to him by somebody that like I know and trust and who's a good business person, right? You don't know about it till it happens directly to you because people don't talk about it. So that's why I chose to, to be vocal. What I did, so it, it took a couple of days. I got the like questionnaire that his like fund sends out to all the, like, whatever, like normal. So I received it and the idea was like, I would fit, I would fill that out and send it back and then we would go down the road kind of thing. So I called him and I said, listen, like, I'm not going to fill out the survey. We're not going to move forward because you were really inappropriate with me. He was on the phone in the car with his wife and for reasons I don't understand, he chose to— everything I said to him from you were inappropriate, he started to repeat out loud so she could hear it. Like, I was inappropriate? You thought that I did this at lunch and dinner? Like, blah, blah, blah. And then she's talking too. And I said, listen. I called to tell you why we're not going to work with you. You could tell her whatever you want later. And then he was like, have a nice day. And he hung up, immediately blocked me on WhatsApp, blocked me on LinkedIn.

Oh my gosh.

And then that was, that was the end of the interaction with him. And then I made that post on LinkedIn and I, it actually got like, people reached out to me like on the side, but it didn't really like, I think the nature of the post was one that like people don't, weren't interested in engaging in cuz I didn't put a positive spin on it. Like I didn't, I didn't LinkedInify it and make it about like making it through like whatever. Like, I don't know. I really just wanted to call out a bullshit man and I, and I, and I did and I feel good about that and I wasn't actually doing it for engagement. I really just wanted to like say what I had to say in public.

Yeah.

But that's, yeah, that's ultimately, that's what I did. That's how it went. And I. At least felt like my conscience was clear. Right. That's what I would say. Yeah.

No, and I think that's, gosh, that's a hard, God, I'm sorry that that all happened. It's awful and terrible. And I appreciate you sharing. These things are crazy.

Can I ask you a question?

Yeah, please. Yeah.

Is it really that bad? The story that I've told you?

It is in the sense that there was, I mean, I've heard there's a couple of stories like that in the series, right? There's a there's a few. It is that bad because of kind of the, the embedded narcissism in there, uh, of just assuming that it was going to be okay to behave that way and to do it over multiple interactions and to think that, you know, they— this isn't embedded narcissism, but to think that they can just get away with it, right? And to never really, really fully talk about the investment from what you told at any real point in time. And, and that this might be a pattern of behavior is kind of the part that is still sitting in my head. And that's the part that becomes really problematic because when you start to hear stories like this, right, and as I've heard versions of other stories that are similar in the ecosystem, it's not a one-time thing. This is a pattern. And, and that's, that's the part that's the, the overarching problem is that it's, these are the things we have to stop is the patterns of behavior because it, unless We are sharing these stories and there's some way, and what this, the question I want you to answer next is how do you, how do you flag that early? Like what for you would have been the earliest point at which you could have otherwise called this and stopped the interaction earlier looking back and said, you know what, it's not the right fit, I'm moving on and not have even ended up as far down the interaction as you did so that anyone else who might meet him can, the red flag goes up sooner.

Well, the reason I asked you that question was because it's like, as, cuz looking at your face, it's still in my head. I'm like, this shit happens every day. Like it's normal. You know what I mean? Even though it's fucked up.

Yeah.

But that, so I guess what I would, I don't, I almost like don't even really wanna give advice about like, here's like what to notice as far as them being predatory. Like we all know.

Yeah.

The answer is that first moment where you're like, then.

Yeah. That's when it's, and it's, it's trusting.

And like I had that in our first call.

Yeah.

I had that on our very first call.

Yeah. It's trusting our instincts, right? Cuz we know, we, we know and we have, and we're not trusting our instincts when we should.

No, exactly. That's, that's what I would say is the advice. Like it's not about like, oh, there's this predatory red flag or that pred— it, it never feels predatory, which is how they get away with it.

Yeah, well, it feels predatory, but we're not stopping it when we should.

It didn't feel predatory in the moment. It didn't. It felt normal.

It felt like me schmoozing at a business dinner because, because these things happen all the time because we're surrounded by it.

Right. Yeah, exactly.

Yeah.

And probably because of my own internalized misogyny somewhere down the road. You know what I mean?

Yeah. Yeah. Well, cause we'd grown up and I've had, I mean, I've grown up in corporate and grown up in rooms where this behavior is rampant. And so we have layers of, I like to say layers of calluses where you're just like, it just rolls off because you've seen it so often. Uh, and so we don't always stop it when we otherwise could or should.

Do you know what it's like to walk into a room, like a boardroom of Italian automotive executives and you're the only woman?

Yeah. Yeah. Goodness. Okay.

So yeah.

All right. So thinking about the, on the other side of that. Have you seen, have you seen things get better in any part of the venture ecosystem? Are you starting to think, see things change in terms of relationships, behavior, experiences for women that make you feel good?

I mean, I, I think that we've had, we've been really lucky to benefit from knowing certain women in like the VC space, yourself included, Naseem Sayani, who have been really generous with time and knowledge and helping us navigate like at least the bare minimum. Like it's fine to be different, but what's the bare minimum of like meeting the standard so that we can at least kind of like get in the room? There were some really wonderful people that we talked to where like, I don't know, it just wasn't the right stage or it wasn't exactly the right fit or whatever. Have I been floored by something so heartening that I have confidence in the VC landscape today? No, I have not.

Yeah. Okay. If you had like two big ahas or must-knows for other female founders, what would they be?

I think the, the biggest one is before you take your first VC meeting, know inside and out with every fiber of your being that nobody knows your business better than you, and that you're right about what you're choosing to bring into this world until actual metrics tell you otherwise. Actual metrics that you set, not some guy that you just got on a Zoom call with who's never met you. That is what I would say first. And that the, the flip side of that is it requires like a really serious amount of self-awareness. It's not about assuming you're always right. It's about keeping enough people around you that you trust to tell you the truth. It's about telling yourself the truth. It's about doing the work and putting in the research. So that when you go into a meeting and a man chooses to tell you, like a VC I'm talking about, chooses to tell you that your model is wrong or that you are thinking about it incorrectly, you can just tell them to jump in the lake because they don't understand what you're building.

Right. A lot of that, right? I mean, we've talked about this, comes back to like centering in ourselves and in our own confidence. Yeah. And, and yeah.

And in our authenticity.

In our authenticity. And. Owning the room the way we should be owning the room and, and not forgetting that we are actually better than we think we are 100% of the time.

And when we forget 100% of the time, I've worked through like a lot of like perfectionist stuff, whatever, like in the past, doesn't like matter, but I've worked through that stuff and like also like corporate burnout and really trying to mold yourself into that box so that you can succeed. And I did, and I did. So like. Whatever, but it was exhausting and it like could have killed me. Something my therapist said to me while I was doing that, he said, your 70% is somebody's 100%, a normal person's 100%. And I think that that is true of like every woman that I've ever met in business. Honestly, every single one, like every level in every job, in every industry, the world over. Like literally, I'm not exaggerating. I've never met, you know, you know, those guys that you meet who like, I don't know, they just keep getting promoted and like they, they walk into the room and everyone's like, let's listen to him.

Right.

And the question I always like to ask is like, is he, is he really that good or is he just tall?

Yeah. Right.

I think, I think it's the opposite for women where like she's killing herself to be good enough and she on her worst day is 10 times better than that tall guy. So I think that recognizing that that's probably true of you because you know it's true of your friends, and then owning that and living in that instead. Because for us specifically, and I, again, I don't think that this is like the advice for everybody, but where we landed in the end was like, VC's not for us. We're not gonna, we're not gonna be able to create and bring into the world what we want to if we take somebody else's money in the like setup of VC today. Like, it's just not, it's not going to work. It doesn't fit in to see, like, we don't have to, you know, bore the listeners, but you've, you've seen our, our business model intimately. So, you know, that there's a lot of mechanisms in there that have, that offer a lot of promise for the future in different ways, but also are very counter to what a VC needs to give to its LPs.

Yeah, no, it doesn't, it doesn't fit a 10-year structure or a returns model neatly. Right. And that's—

no.

Yeah.

No. Yeah. And I mean, we built in a, a different type of return model and all of that, but it was still too different. And I think over the course of like taking these meetings, adapting a certain amount based on like the feedback we did find relevant and then still not finding success, which led me to like the, you know, the, the very last VC meeting that I, that I took where I was like, forget about it, I'm done. Because there was a guy just sort of telling me. Our math is wrong, our model is wrong, it's set up wrong, the Excel is wrong, everything is wrong. When actually, like the advice that he was giving me, he was telling us that we're doing it wrong and that we need to flip the inventory that we have, use that cash, all of it, to buy more inventory and then flip it and then basically get ourselves into like a cash crunch that has no hope of really ever ending where ultimately the bigger we get, the more we're going to have to borrow. Which keeps us entrenched in the system that we're trying to change.

And as soon as I realized that, I was like, okay, well, yeah, that's not gonna work. That's not what we're trying to do.

It's not gonna work.

Right.

No. And, and so then I just, I, I said, okay, like, thanks, but no thanks. Like, we're just gonna move on. And then he continued to follow up with me over email to see if I made changes to my model and stuff. And I was like, no, like it's counter to what we're trying to do. So we didn't.

Yeah.

And then the last email was like, do you want, you know, like I bought this great CFO, he's amazing. Like, do you. I, I should put you guys in touch. Like, do you need help? And it's like, actually, I have a really amazing woman locally who's gonna be our CFO, so.

Yeah. So I'm good. Thank you.

What are you for? Like, it's like you don't believe in me enough to write me a check, but you think I'm smart enough. You think I'm smart enough that you might be able to make money on a backend deal. And it's like, fuck you so much.

No, totally.

Excuse my language.

No, it's okay.

But like, I don't, have other words for it.

Yeah. Yeah.

Fuck you. You think that I'm good enough to make money off of.

Yeah. But not good enough to invest in.

But not good enough to invest it.

Yeah.

Yeah.

No, that drives me crazy.

Yeah.

You're like, nope, thank you. Click. See you later. Yeah.

Yeah. Like we're good.

We're good.

Yeah. And it's so boring and it's just like, you know, I have all, what I'll say is like, I have a lot of hope for like future generations. I have a lot of hope for, you know, the more like millennials that get into executive office and like executive offices. No, sorry, not like the presidency. That's not what I meant. Uh, but also maybe that, that things will start to change because certain things that are somehow not obvious even to a lot of Gen X is fundamentally obvious to a lot of Millennials and even more like viscerally obvious to Gen Z. Like, they're like, what is this? So I have hope that it's going to change, but I honestly like Naseem, aside from you and people like you doing the work that you're doing in that other camp, I don't have a lot of confidence for the, the current VC landscape, like doing anything good. I really don't.

Yeah, it's, it's, uh, there's a lot that has to move and shift and thinking that has to move. So there's a lot of work to do. Last question before we wrap up. What can everyone listening do to help Milo and the business and what you're building?

Well, we've got a lot of really exciting stuff coming up actually. We're in a bit of like a lull. We're just about to do, like launch a really exciting rebrand and like local campaign here in Toronto, a community-based campaign. So we're really excited about that. I think the best thing people could do for now is maybe just follow me on Instagram cuz then you go, you'll see everything. There's books up there. There's, you'll get, you'll be able to stay up to date on Milo. And that's just Lisa S. Hilliard on Instagram and on TikTok.

We'll put it, we'll put a lot of things in the show notes so people can find it there for sure. So, okay.

Yeah, perfect.

Amazing. Well, thank you so much for being on the podcast and for telling your story and sharing it.

Yeah, my pleasure.

So candid and open. I think it's tremendous and it's gonna be so helpful for so many folks that listen. So thank you.

Oh, it's my pleasure. Thank you so much for having me. Thank you for also creating a space where we can tell these stories to each other and for each other. It's unique. Yeah.

Absolutely. I appreciate it. Yeah, I wanted to make it happen. So here we are, season 1, and we'll see how far we get. So thank you. Love it.

Okay. Thanks, Naseem Sayani.

Thank you. Thanks for listening to The Capital Flex. If today's episode hit home, share it with the founder you love and follow me on LinkedIn for more.