946 Lindsey Mignano:

Wings of Inspired Business Podcast EP946 – Host Melinda Wittstock Interviews Lindsey Mignano

Melinda Wittstock:

Coming up on Wings of Inspired Business:

Lindsey Mignano:

It still is a very male dominated space. And I think female founders have a hard time breaking into that based on the dynamics between female founders who are looking for money and male GPs who have check writing power and socializing outside of work hours, which no one talks about. There is a dynamic there, a heterosexual dynamic and a power dynamic that is, that is not to be ignored. We are dealing with maybe a 20 something or 30 something woman asking for money from a man who is married in 55 or something like that. And our female founders talk with us about it, you know, off the record, as uncomfortable. My husband used to be a partner in a venture capital firm. It was uncomfortable for him.

Melinda Wittstock:

Raising money for an early-stage tech startup is hard for anyone, especially if they didn’t go to Stanford, MIT or Harvard, drop out of any of those schools, or have existing relationships with Silicon Valley VCs. It’s all the harder for women, not least because of the “is he meeting me because he wants to date me, or because he wants to fund my company” dynamic Silicon Valley lawyer Lindsey Mignano is describing. Lindsey is the founder of the female-owned law firm SSM Legal where she represents a lot of early-stage female founders – from company set up through fundraising and M&A. Today she shares all the challenges, trends and opportunities for women entrepreneurs in tech.

Melinda Wittstock:

Hi, I’m Melinda Wittstock and welcome to Wings of Inspired Business, where we share the inspiring entrepreneurial journeys, epiphanies, and practical advice from successful female founders … so you have everything you need at your fingertips to build the business and life of your dreams. I’m all about paying it forward as a five-time serial entrepreneur, so I started this podcast to catalyze an ecosystem where women entrepreneurs mentor, promote, buy from, and invest in each other. Because together we’re stronger, and we all soar higher when we fly together and lift as we climb.

Melinda Wittstock:

Today we meet an inspiring entrepreneur who has been recognized as a “Rising Star” by Super Lawyers every year from 2016 to 2024, an honor awarded to only 2.5% of attorneys under age 40. Lindsey Mignano, the founder of SSM Legal in San Francisco, is the unstoppable dynamo helping women entrepreneurs in tech navigate the complexities and challenges of raising money. Lindsey is a keen and connected observer on the early-stage Silicon Valley startup scene, and today she shares some sobering new data about just how hard it is to raise money.

Melinda Wittstock:

Bottom line, there’s been a significant downturn in early-stage funding, with seed investment down 31% and Series A deals down 21%, and the check sizes noticeably smaller. It was already hard for women to raise VC money, less than 2% of us succeeding, so how best to navigate these evolving market realities?

Melinda Wittstock:

Lindsey will be here in a moment, and first:

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Melinda Wittstock:

Ever since post-pandemic inflation and high interest rates made money more expensive, investors have gotten very picky about the startups they fund. It was never easy before, and now it’s harder than ever to raise money for an early-stage tech company. Despite headlines that would convince you that investors in AI are spending like drunken sailors, even those investments are few and far between. 

Melinda Wittstock:

Today Lindsey Mignano brings her legal expertise to the table, sharing candid stories and hard stats around the gender gap in funding, how biases play out in VC decisions, and the unseen hurdles that innovative women face in an ecosystem still dominated by the “usual suspects.” Lindsey also offers strategic advice for female founders on how to build relationships, target the right investors, and structure their companies for success—even when the cards seem stacked against them. We also get into practical realities on everything from team formation and founder equity splits to California’s tricky employment laws and the complicated dynamics of building diverse, high-growth tech teams.

Melinda Wittstock:

Let’s put on our wings with the inspiring Lindsey Mignano.

[INTERVIEW]

Melinda Wittstock:

Lindsay, welcome to Wings.

Lindsey Mignano:

Hi. Thank you for having me. I appreciate it. Nice to meet you.

Melinda Wittstock:

Well, I’m fascinated with your background in the law, but I just want to jump straight into the guts here of what’s going on in AI venture funding because we see so many companies right at the top end just taken down huge loads of money, but then we see other companies really struggling to raise money. So, what are the top line trends here that we need to be aware of?

Lindsey Mignano:

Absolutely. Number one, we have to understand the broader ecosystem.

Melinda Wittstock:

Right.

Lindsey Mignano:

So right now, as of let’s say quarter one is 2025, if you look at the data from Carta or NVCA or CB Insights or any of the accessible data, you’re going to see that early-stage companies across the board. So, Seed and Series A investments in terms of deal count and deal value are down. I think the quarter one number from Carta was something like Seed was down 31% in deal count. Series A at 21% in deal count as compared to 2023. So, like comparing 2025 to 2023 and then just the number of dollars deployed in that round is down 40% for Seed and, and 19% for Series A as compared to 2023.

Melinda Wittstock:

That’s crazy. What, what is driving that?

Lindsey Mignano:

I think it’s investor pickiness. What we’re seeing at least anecdotally because we are a firm that serves a lot of early-stage companies. And I would, I define early stage a little bit more broadly in light of the amount of monies going to them. Like I would say it would go from Pre Seed, Seed, Series A, occasionally Series B. Because not every Series B is a behemoth of a Series B. That really takes them out of early stage from a pure dollar count…

Melinda Wittstock:

Right.

Lindsey Mignano:

…Deal value count. But we’re seeing them raise less and it has been consistent less dollars and less frequently in the past since 2021. Probably more markedly in the past two years, we’ve seen deal count go down as well as deal amount go down. And we’ve seen that the ones that are actually getting the money are getting bigger money. So, we just had a client, for example, that is enterprise AI in deep tech that closed a 4.4 pre seed round. That’s 4.4 million in a pre-seed first safe note round. Okay. So that is the more of the common like what we’re seeing today rather than for example that 4.4 million being spread across 10 different companies.

Lindsey Mignano:

We feel as though, and I think the data does back this up that the, the vibe in the room is that not all the early-stage companies are getting funded, but the ones who are getting funded are hitting the jackpot. Like they are getting more money than they would have because the investors have more money to deploy to them. They’re the lucky few.

Melinda Wittstock:

Right?

Lindsey Mignano:

So, more dollars to less companies, is what we’re seeing anecdotally. And then at, of course, if you look statistically, late-stage deals, so like C D all the way up the chain, they’re up, right? Like those are good, those people are, people are investing in those companies. But early stage is really suffering. The bright spot is AI. So, if you look at the hot verticals, you know, anywhere, statistically or even anecdotally, I would say AI, enterprise software, SaaS or pass AI, some consumer software, especially if it’s in fintech, AI, in deep tech, they’re getting funded more often than our other companies, right? So, they’re, you know, they’re the hot, you know, vertical right now. But even within that vertical, it’s not just everyone’s getting funded like 2021, we’re really seeing our VCs be pickier. They’re asking for like demonstrated traction or stickiness which is, you know, really hard to prove as an early-stage company going for your A round, right? Like you have to show some sort of like beta or pilot that’s converting into paid. Some of the VCs at the early stage are requesting ARR and I’ve seen everything from, let’s say for a seed round of 3 million, on a safe note, 500,000 to 1 million in ARR from other enterprises.

Lindsey Mignano:

So those are companies that are targeting other enterprises, and they’ve issued out maybe a three-month beta that’s converting into a paid annual subscription, ideally with the payment and the contract being drafted to be delivered, delivered annually for that one year so that it’s money off the streets, right. At series A, it used to be 1 to 4 million for let’s say a 10 million Series A that VCs would look for the ARR. But now we’re seeing like a real sweet spot at 2 or 3 and 3 being more than 2, you know, the preferred number of ARR that you have with other enterprise companies in paid subscriptions that are both in the legal documents and on the books of the company.

Melinda Wittstock:

Right.

Lindsey Mignano:

So, I, I love this conversation with VCs at the early stage because some people are very, if, when I sit on panels with them, they’re very adamant, like the company has to have some sort of traction, some sort of ARR, right at, @ an earlier stage than would be. And then other VCs especially the ones that are investing at Pre Seed, you know, will say I don’t require error at all. If I’m requiring ARR, that means I’ve got to them too late, I should have gotten to them earlier.

Melinda Wittstock:

Right.

Lindsey Mignano:

So, it’s, it’s a mixed bag but I would say it’s half, half A lot of our clients who are not getting the money are not getting the money because they don’t have, you know, paid customer engagements.

Melinda Wittstock:

So, so tricky because you set up this chicken and egg scenario where it’s hard to get there. Like you need the money to get there, right?

Lindsey Mignano:

Oh I know, but you know, for you know, and it’s like which one comes first? And I think you know, VCs are expecting companies to at the earlier stage to be really scrappy about it like to do that kind of founder led sales and getting those paid contracts as like maybe say a two-person team is a lot of work. It’s a lot of work. So, you know, that has been something that a lot of our founders are having a hard time with. Well, it’s really hard.

Melinda Wittstock:

I mean I know with, with several startups now where I’ve done kind of enterprise sales at the stage and I can’t count the number of times where the company loves technology, wants to do it, but they’re not sure you’re going to be around unless you’ve been funded. So, like being asked questions like so are you venture backed? And so, if you’re not, if you haven’t closed that round yet, it’s actually harder to close those deals.

Lindsey Mignano:

Oh absolutely. And sometimes you need the money to come in from venture to make yourself sock to compliant so that you can go get those big, those bigger customers that will, you know, really just embrace you wholeheartedly.

Melinda Wittstock:

Right?

Lindsey Mignano:

It’s a chicken.

Melinda Wittstock:

And that’s not cheap to do.

Lindsey Mignano:

No, that’s not cheap especially and even for the ones that are like health tech AI, HIPAA compliance is not cheap. Paying a consulting firm on the back end to make sure that your, your software as a service or platform as a service actually does what your privacy policy says it can do and be and is HIPAA compliant requires some level of funding. It’s just not in an inexpensive lift. So, it’s a chicken or egg situation. But for AI companies they are still getting more of it. So, when you see the stats from CB Insights from Quarter 2, 2025, if you look at the amount, the dollars in the raise, AI companies at the early stage and across the board have a median deal size of 4.6 as compared to 3.5 for other broader market companies. And then when you look at, you know, even, even with 72% happening in early stage globally, because CB insight tends to measure things globally, you know they’re getting a lot of the deals. It’s, it’s, you know, it’s, it’s 47.3 billion were deployed and, and a lot of the AI companies are the ones that are getting it right.

Lindsey Mignano:

So, there’s, there’s still a lot of interest in it. I just haven’t seen, I guess on my docket of clients the standards being relaxed from early-stage ventures. I haven’t, I haven’t seen that as much. What I’m seeing is it’s the usual suspects who are getting funded big money from early stage vc. And these are repeat founders. So, founders who have already raised something from the existing VCs and then exited it and then just tapped them again for the next venture. So that’s there and that’s always been there. It’s of course founders with great ideas but also great resumes.

Lindsey Mignano:

So, you’re going to see like founders who have like direct deep tech knowledge from being institutionally organized and working in that type of industry for like years and years and years.

Melinda Wittstock:

Right.

Lindsey Mignano:

And, and that’s never been like that. Those are certainly not the only considerations. But it is one of those things where when you look at the clients who we are seeing get funded, it’s all the usual suspects and generally they are all male teams, especially if they’re in really heavy deep tech AI or life sciences that has an AI component. Really technical startups, we’ve seen less mixed gender teams on that too. 

Melinda Wittstock:

So, this is a really, this is difficult for women because women just have just, just the historical nature of this. Women have less exits. Right. Because we’re relatively new to this. But women, tremendous domain, tend to have tremendous domain expertise. And what I’m seeing in the AI side is women are being very innovative about the application of AI, like not only advancing the AI, I mean they’re not behind the big, you know, like the big battle between, you know, Anthropic and OpenAI and Google and Microsoft and all of that, but really innovative market tested applications of the AI that people will actually pay for. But I see a lot of those women really struggling to raise money.

Lindsey Mignano:

Oh yeah, absolutely. When you look at like if you look at the stats from NBCA from like 2021, when I really think we had the height of, of, of like attention to diversity issues in this industry in terms of the, the deal count and the, the dollars being deployed, it’s, it’s gone down every single year since 2021 and steeply so. You know, in 2025, right now if you exclude OpenAI, which is partially female founded, but let’s exclude it because those dollars are so big and not representative of the whole startup ecosystem. But if you exclude OpenAI, you know, only 21.3% of all deals in 2025 have gone to female founded companies. And that could be for a mixed gender team. When it’s an all-female team or a solo female founder, that number goes down to 354deals or 5.3% of all deals. When you look at dollars like it’s, it’s even more terrible where if you are an all-female team or a female founded company and you’re a solo female founder, you took home 0.8% of all venture dollars deployed in 2025. So far.

Lindsey Mignano:

If you add a man to the room, that goes up to 48.5%. So, I think women founders are in such a terrible position at an early stage to be in. And you know, I have some female founders who are like, I’m going to stay female founded this whole time. Like I’m going to build out a female founded team. Like, I love this and I’m, I’m really passionate about it and I don’t need a guy CTO, which is usually what, what they, you know, they’re told to go get, right? And, and I’m like, yeah, do it. And then we have other female founders who are like, okay, yeah, I know I’m going to need a male CTO because I can’t find a female CTO with the qualifications that I need. And all the people who are applying or I’m meeting are male who are CTOs.

Melinda Wittstock:

Yeah, that’s my experience. I’ve like, I don’t think I’ve in my wildest dreams. I would love a female CTO.

Lindsey Mignano:

I have, you know, looked for them women technical founders with the CTO level experience for other clients, like clients asking me for other clients who might be like winding down but having the experience. And all of the CTOs, unfortunately on our client docket are all male. So, when that decision is, or when that female founder is being told usually by an angel investor or a VC, that she needs a technical co-founder in order to get Funding, she is looking at a predominantly male choice. And then we see the equity battles here, which is really interesting because we have, you know, normally seen 55, 45 as a split. 55% to the first co-founder, the president, CEO, the woman with the idea, 45% to the second co-founder who comes in a year later or something like that, right. To just to do the technical. And we see them get hustled for like, oh no, I want to be 51% since I’m the technical co-founder. You take 49, this is the company that you started and it’s really hard.

Lindsey Mignano:

They’re up against a rock and a hard place and there’s no right answer. There’s like, you can’t, you can take a very principled approach and say, screw it, I’m not going to bring on this CTO and then never get funded.

Melinda Wittstock:

Never get funded. Or you can go that route. And you know, I’ve seen so many female founders lose their companies.

Lindsey Mignano:

Yes. And then essentially it’s a sacrifice. It’s like, well, okay, so I guess I’m now what, 49% and he’s 51%. Because the worst mistake you can make is do 50-50 in a two-founder team. You can’t get anything done. Like you could, you could agree to be 50-50 and both be on the board of directors and have an equal vote as shareholder and equal voters directors. But if you guys ever get in a conflict, like nothing is, nothing happens.

Melinda Wittstock:

Right.

Lindsey Mignano:

So, like that’s a disaster.

Melinda Wittstock:

Like I don’t think I’d ever invest in a company that was 50-50.

Lindsey Mignano:

I’ve, we’ve had a couple of founder fallouts where it was 50-50. And it’s always interesting. It’s never the mixed gender teams where that happens. It’s always like, you know, a female founded, they’ve been best friends since college and then all of a sudden something happens and you’re like, no. Your Co-Presidents & Co-CEOs & Co-Treasurers, this, this egalitarian, like I want to be equal partners with you has caused a legal conflict that we now don’t know how to like to massage out of this company.

Melinda Wittstock:

Right.

Lindsey Mignano:

So, we’ve had it happen twice where we had to like, you know, deal with business divorces at 50 50. And we would never advise it. But what happens then, of course, is that female founder, when she takes on a male co-founder, knows it has to be at least 51-49. Someone’s got to have the majority. And from a practical perspective, and Then it becomes a matter of, okay, is she going to give up her one year of work and just take a demotion essentially. So, she can have a male CTO or a CTO who happens to be male, and then get venture funding because that’s the feedback she’s getting. Right. It’s a hard position.

Melinda Wittstock:

So, another big challenge and a headwind of sorts. Back in the day, it used to be in the, in the, in the scrappy startup world that your first team members were basically unpaid or they were, like, earning equity or they were working for equity or some sort of deferred compensation. Now that’s actually a felony wage theft in California. Like, you can’t do that anymore. And it’s actually like the only companies that can really compete not only for talent, but just on the legal side of things are folks who can pay their employees as W2s.

Melinda Wittstock:

Right.

Lindsey Mignano:

And California is very specific about that. Officers and directors can be individually personally liable for failure to pay wage an hour to their California staff. That’s within the past 10 years.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like, to have that individual liability. So, like founders who are not paying their staff or even their co-founders, like, if there is a dispute, it’s not just like, oh, well, everyone knows you work for sweat equity. You don’t get paid minimum wage an hour if you haven’t been running payroll. Minimum wage an hour, and paying someone at least hourly. You know, in the state of California, where they live, they could hire a fantastic employment lawyer, hit you for all the penalties if they don’t like what you’re doing with their equity.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like, it’s, it’s quite a risk. And so, you do require funding to build teams from a legal perspective.

Melinda Wittstock:

So, under those rules, there never would have been a Google, an Apple, like, you know, Facebook.

Lindsey Mignano:

There could be, but then it’s a, it’s. I mean, there are tons of our clients who we tell, hey, listen, I know you’re going to not do this, but in theory, you are supposed to be paying your dev team and your, you know, your unofficial co-founder, like, in accordance with California wage and hour, because that’s where they live. That’s where you’re headquartered. That’s where you live or you could be individually liable. And there are a lot of people who are like so what are they going to do? Sue me? And you’re like yeah, they actually, you know, can sue you and they can sue you personally, they can sue the company, but they’re like well then I’ll just take the risk. Like there are people who will take the risk on that purposefully because they know there’s no other way.

Melinda Wittstock:

Right.

Lindsey Mignano:

And the minute that they get the funding that they have, let’s say they get that 4.4, you know, pre seed, that’s way more than you would need to pay someone minimum hour in wage. But like the first usually precede and I would call precede anything from like 500 to a million.

Melinda Wittstock:

Right.

Lindsey Mignano:

So, they, they, they do everything right. Like they start running payroll, they start doing things in the right way, but they’re doing it in the right way at an earlier stage than you, you would think.

Melinda Wittstock:

Yeah, because all it takes is one employee who maybe just is not performing very well or just decides they’re going to be awkward and like your whole thing can fall apart. I think this is really terrible. Now I understand California say for instance wants to prevent wage theft is a real thing. There are major companies that don’t pay people. Right. Or stiff their employees. So, I can understand why the law needs something to protect employees. That makes perfect sense to me.

Melinda Wittstock:

But for startups surely shouldn’t there be a different rule?

Lindsey Mignano:

And, and that’s the, that’s the issue is the code. As with many things in the law, sometimes the law doesn’t catch up to the practical realities of the day. And it doesn’t differentiate between companies that are five person companies versus companies that are like okay, actually revenue positive and can pay people or investment, you know, has come in. It’s just a blanket rule.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like it’s just, there’s no differentiation in that code. So, the same law applies to you if you’re a founder of a five-person company and you have two co-founders who are also not paid and you have three devs as, as would apply to Google. Like and that’s a very different economic situation.

Melinda Wittstock:

Right.

Lindsey Mignano:

And so, what, what does that mean from a practical perspective? It means you have to get funding earlier and, and bigger than you would think if you want to comply, if you are risk averse and you don’t want to take the risk. And again, a lot of our companies just take the risk of noncompliance and say we’ll punt it to another day. That’s fine. But if you do not want to take the risk because let’s say you’re worth something because you have a house and you have, you know, a savings account, you have, you have a family that you’d like to provide for in some way, then no, like you may not want that risk. Especially if you’re a wealthy individual who does have deep pockets enough to pay out, you know, employees, including co-founders who have not been paid in accordance to wage an hour. And that is one of the biggest things that we see in founder fallouts. Like a lot of our work is also navigating business divorce. And all it takes is one founder and the other founder to not get along.

Lindsey Mignano:

And the one that lives in California, let’s say they’re a multi coast team, New York and California, but they’re headquartered in both places because the founders live in both places. All she has to do is hire a great employment lawyer and say, hey, you haven’t been paying me in accordance with California wage an hour co-founder, neither have you been paid.

Melinda Wittstock:

Right.

Lindsey Mignano:

But I can sue you individually and the company. And now that we have some angel funding and we’re not getting along like we could easily, you know, just with the penalties, the waiting time penalties that are involved gut whatever we just raised. And so, it’s quite a lot of leverage to have as well.

Melinda Wittstock:

That’s crazy. So that, that’s such a bind because like, okay, so all these, all these VCs want to see proof of traction and all this sort of stuff. You’re competing like, so for AI researchers and for AI engineers, you’re competing for really top talent. And you can’t really compete, you can’t really pay them because you’re up against, you know, I don’t know what Zuckerberg paying people now it’s like.

Lindsey Mignano:

Right. And you need their expertise.

Melinda Wittstock:

Yeah. And meanwhile you’ve got this other thing. But you’ve got to show these things. It becomes almost impossible.

Lindsey Mignano:

Yeah. Especially for, think about like AI companies that are in like hard tech. Like, and I consider that some, yes, it could be like robotics or defense and hardware focus, of course. But I also kind of consider anything hard tech where it’s like that plus really capital intensive. Like you need so much money to scale that.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like to build that, to make it sticky and to make it, you know, adopted by the entire enterprise or government unit that you’re targeting.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like that’s a lot of money. And now you have to also worry about making sure that you’re paying people at Least in accordance with wage and hour. Or taking, you know, as a founder, taking a haircut on your equity, bringing yourself down and giving them more equity to make it at least emotionally fulfilling enough for them to stay around.

Melinda Wittstock:

Right.

Lindsey Mignano:

And you still do have.

Melinda Wittstock:

Yeah. So, this trend has a really chilling effect on innovation.

Lindsey Mignano:

It can. It can if the founder is risk averse. But again, most of our clients are completely fine taking that risk. They can know the law, but they might say that from a practical reality, you can’t squeeze water from a rock. We don’t have the funding for it.

Melinda Wittstock:

Right.

Lindsey Mignano:

So, they could just decide, I’m going to take the risk. And that’s not a wrong decision. I mean, legally it is wrong to not pay people from a code position. But from a business decision perspective, there’s a lot of reasons why companies do things that are not in accordance with what compliance would say you have to do.

Melinda Wittstock:

Yeah, but you just think, don’t found your company in California. But then you need that ecosystem and your investors are like, I’m only going to fund you if I’m. If you’re there.

Lindsey Mignano:

Yeah. You can’t not fund it in California. In California, like even the latest stats from NVCA came out with 35 billion deployed. The next up was LA with 6.5 and New York with 6.5point. That is a huge jump in terms of like the dollars deployed. Like you want to be in the SF Bay Area because of the pure number of like amount of money that’s circulating in this economy and the amount of deals that’s going out. Like, there’s just no other way that you can be competitive if you’re looking for financing.

Melinda Wittstock:

Yeah, it’s crazy. I mean, are there any trends towards Silicon Valley investors looking at companies that are not based there? Or is it still very like, you got to be here?

Lindsey Mignano:

You know, this is, and this is what’s so frustrating for me too, because we have clients across the continent and some of them who are European.

Melinda Wittstock:

Right.

Lindsey Mignano:

Who have come here to raise a Series A, but they raise, let’s say, 5 million in the UK or something. During the pandemic, when we were all remote and VCS were remote as well, there was no geographical, like, preference. There was nothing where they were like, I kind of prefer to like deploy dollars locally here.

Melinda Wittstock:

Right.

Lindsey Mignano:

That way I can go to coffee with this guy or call him into my office if I want to talk to him about what he’s doing. There was nothing like that. And people were, I think, getting. You were seeing deployment A lot, you know, across state lines and, and it wasn’t a thing. And I really thought, oh gosh, I hope this stays that way because that’s going to democratize access for people who don’t live in the expensive place called San Francisco, right, who have great technology, but maybe they live in Salt Lake City, Utah or Atlanta, Georgia. But they’re great founders.

Melinda Wittstock:

Right?

Lindsey Mignano:

Look, this is going to be great. And then in the recent years, we’ve seen less and less of that. We’ve seen more of a return to deployment to local companies for all the traditional reasons that have always been cited, right, which is Stanford GSB is here, Haas Business School is here. We have all these great academic and research institutions right at our fingertips in the Bay Area. And they’re picking pedigreed, you know, founders. Like, that’s never been not a reason for a Bay Area deployment. And we’re seeing more of a locality matters or location matters perspective now. So much so that some of the founders, you know, who are like foreign, like they live in Germany or Switzerland or the UK when they’re thinking of where to set up their company, their subsidiary before a flip for a financing event, let’s say they’re just here, you know, six months to investigate the market, but they’re not raising right away.

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Melinda Wittstock:

And we’re back with Lindsey Mignano, Silicon Valley corporate lawyer and founder of SSM Legal.

[INTERVIEW CONTINUES]

Lindsey Mignano:

They’ll set their company up in California because they know that if they want to flip and raise later on, you know, they’re already dealing with some prejudice being a foreign founder. They don’t want to; they don’t want to not be in the right location.

Melinda Wittstock:

Right?

Lindsey Mignano:

So, if they’re an enterprise AI company or enterprise pass or SaaS in some way, even consumer, they, they will be, you know, NSF Bay Area. It’s usually the ones that are kind of more sector specific. Like if you were like life sciences or pharma tech or med tech or medical device that you, maybe you would go to Boston or if you’re heavy fintech and maybe you want to be in New York for that. Like we would see that. But for the most part a lot of them are migrating here for the, to be in the ecosystem where the monies are deployed.

Melinda Wittstock:

So how is all this crackdown on immigration affecting this?

Lindsey Mignano:

So, yeah, so one of my very good referral sources and friend is a woman named Sophie Alcorn of Alcor Immigration Law. And she and I have, were sorority sisters at Stanford. We go back, way, way back. And we share a lot of clients, you know, because we started our firms around the same time. So, we you know, we Both started around 20. I think she was 2015, and I was like, 2016 or something like that. So, we’ve seen it kind of together along the way. And I used to see more founders coming from her office who were foreign and who were looking for the appropriate visas.

Lindsey Mignano:

And they were going to use the startup company they founded to get their O1, their L1, their H1B, their STEM or whatever it was. They were going to basically use that vehicle, that startup vehicle, and they were going to live here. They were going to physically live in California. And I’ve seen less of that now. I’ve seen founders who are foreign who maybe got laid off from their big tech job, and they have no visa now, and they’re considering whether they go home, or they take the risk on the visa not being approved, the transfer to the new company, or just even reconsidering whether they want us to hear from, like, a cultural perspective. Because where the US is right now is not where the US used to be in 2020.

Melinda Wittstock:

Right.

Lindsey Mignano:

So culturally, do they want. Do they agree with what’s going on here? Do they want to stay here? And I’ve seen less foreign founders knock on our door as a result. I think it could be many factors, but I think it’s not just immigrant. I think it’s not just, can they get a visa? I think it’s also, do I really want to live here? In what. In terms of what’s going on in the United States today and where the culture is shifting and what I believe in. And so, I think it is different now.

Melinda Wittstock:

All right, so there’s all these headwinds. What’s your best advice? Okay, so say there’s a sole female founder or female founder team. They have some really cracking AI.

Melinda Wittstock:

They have a market that they have deep domain expertise in. They’ve, like, bootstrapped. They’ve done everything. They’ve, like, not paid themselves. They’re like. They’re out there doing it, but struggling to raise money. Like, what’s your best advice? What should they be doing given all of this?

Lindsey Mignano:

Yeah, and this is, like, right up my alley. I was a feminist studies major in college, so, like, I don’t practice feminist studies as like a profession. But I absolutely use it in the context of my women owned corporate law firm.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like it comes up all the time. So, like my best advice is that they need to understand because there are all kinds of reasons that we’ve all heard about as to why women are not getting funding.

Melinda Wittstock:

Right.

Lindsey Mignano:

It could be structural, it could be relational, it could be bias, it could be capital reasons. It could be the verticals that they’re, they’re, you know, that they’re in. Men who are the Czech writers in the VC firm don’t understand.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like they just don’t understand Femtech as well and the huge market that is. I don’t, I think one of the things that is often not talked about is strategy in choosing your first pre seed or seed VC. And here’s why. If you look at the, the funds that for that fund a lot of precede checks. So, I’m thinking like 150, you know, something in, in the 600000 round but it’s a, it’s a smaller check, right? 80 to 150 or something like that. A lot of these are emerging venture managers who are women and they are, some of them are even you know, vertical focused on FemTech or something that is a vertical that a lot of women entrepreneurs go into or they are like the purpose of the fund is to only invest in female founders, right? So, there are tons of funds like this. I think that there are, these are great, these are awesome. I think they should hit up those funds as a matter of like doing business.

Lindsey Mignano:

Because I think that you know, women GPs tend to understand especially the, the bias in the industry towards very technical hard tech that maybe women may not be in, but they will understand things like FemTech and the market for that.

Melinda Wittstock:

Right?

Lindsey Mignano:

And here’s the rub. While I say that, I also say this can be something that we approach with caution because what we have seen some of our female founders do is approach those women get funded by those women and you know, it’s a female owned venture fund funding a female owned startup. And at the next round the VC comes in and says oh well she just invested in you because you’re a woman and she’s a woman and something about ology, it’s terrible. So, while I say yes, you have to be in the room with people who cut checks and guess what? Women GPs are going to be more likely to cut you checks. I also say but caution because sometimes your later investors see this as a pigeonhole. They see this as she just invested in you because you’re a woman just like her, as opposed to. No, she invested in you because you’re a great founder and your technology is proprietary and defensible, and everything is there. But I think it’s the, in terms of like the, the women founders to women funders, I think there’s, I think there’s enough reasons, aside from that guy saying it later on series A, there’s enough reasons to go and target those, those funders.

Lindsey Mignano:

I think it is more successful on average than it is unsuccessful.

Melinda Wittstock:

You know what I found though, as a tech founder, talking to those, like at the early stages of my companies with, I found that a lot of those female venture funds tend to focus on stuff that they know or perhaps that they would be consumers of. And some of the big tech plays get ruled out often because they have smaller funds, therefore smaller check sizes. So, their money isn’t really going to be enough.

Lindsey Mignano:

Yeah, you have to raise another round.

Melinda Wittstock:

Right.

Melinda Wittstock:

And for the, for the, especially for the women who are going for her playing big. Right. Or going for big ecosystem plays or have really like I, I remember of, oh, gosh, this was a couple of years ago, but talking to a female venture fund, she’ll remain unnamed. Who they said to me, well, look, we, we love what you’re doing. It’s really great. But like, we’re not experts in AI, so we can’t really invest in you. And I was thinking to myself, gosh, well, like when you go to the doctor and, and the doctor says you really need to do this or have this kind of treatment, I mean, do you say, look, I have to go get my medical degree to understand the treatment before I can evaluate your… right?

Melinda Wittstock:

So almost like there was this barrier because the, the. And I think it’s changing, but I don’t know it, it was kind of interesting. Like, I’ve been more successful raising money from men than I have from women.

Lindsey Mignano:

And I think it depends, you know, who, what woman GP is on the other side of that call. Because we have seen, you know, even if it’s not in their vertical, them say, well, hey, guess you know what? It’s not me. I don’t know this area, but I know so and so at this fund and they invest in it. And let me make a warm introduction for you, right? Like that is an extra step for free that does her no benefit because she’s passing on your deal, but she’s taking the time to make a thoughtful recommendation to someone who does. And ideally that happens everywhere. In the.

Melinda Wittstock:

Not everybody, but what about that fund? Just saying, hey, look, you know, we’re just going to call in an expert who is really, you know, who can evaluate your tech. Like, why don’t they do that?

Lindsey Mignano:

You know, I mean, they absolutely could, right? They could bring in a partner who’s maybe not the one who’s bringing on all the deals, but is, is getting deal by deal carry and literally just getting the, the carry for this one deal.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like there are structures and venture funds where you can do that.

Melinda Wittstock:

Right.

Lindsey Mignano:

Where you can bring in someone to only evaluate enterprise AI deals. If you’re a micro venture fund that’s focused in, you know, FemTech.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like you could, you could do that. That’s possible. And I just don’t know, you know, everyone has their little like focus area and everyone is so sectored these days so that no one’s really a generalist anymore. And I, and I have strong feelings about why generalists are important in some ways.

Melinda Wittstock:

Right.

Lindsey Mignano:

So, I don’t know. I haven’t seen that done as often. I hear what you’re saying. I’ve more so seen the past to another fund that actually does do that work. But I think you’re spot on with regard to the vertical issue, which is both on a startup side and on a fund side that female founders and female GPs tend to focus on verticals like Femtech or fashion, beauty, wellness, retail, tech, like those sorts of things. And later on, subsequent real big money investors, maybe they don’t see this because they’re unfamiliar with the scope of the industry. They don’t see this as like a profitable endeavor for them in light of the hard tech AI that they invest in.

Melinda Wittstock:

Right.

Lindsey Mignano:

But that’s just because they don’t have any familiarity with like beauty, like, like beauty acquisitions or Haley Bieber’s company. Like you would have been a fool not to invest in Haley Bieber’s company.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like, so it’s just a matter of unfamiliarity at the later, bigger check sizes, I think. Yeah, I mean women get.

Melinda Wittstock:

I remember doing a investor pitch to a female fund for my previous company and they, they literally the pushback was, well, I wouldn’t use this. And I was like, well, I know you’re not my target customer. Yeah, like this is my target customer and we have product market fit and like people are paying us like we have ARR. But like you, you still couldn’t. I was just like crazy.

Lindsey Mignano:

I think that’s the investor problem generally though, you know what I mean? It’s like I remember. So, backstory. My husband’s not a partner at a venture capital firm anymore. He’s retired. But he used to be when I met him. And I had been jobless then, so I was just studying for the bar. I just had passed the bar was one of those. And I was like, you know, par value.0001 my career.

Lindsey Mignano:

And he was this venture partner who I met. And I remember he had asked me for, like, for feedback on certain things like stitch fix or. Or, you know, could I try it? Because he doesn’t even know. Like, he didn’t even know whether or not there was a market for it where you’re like, what? You’re like, no, no, no. It’s probably in the deck. The deck probably explains, like, whether there’s a market for it. You should probably just go, but like, do I have to personally subscribe and do this vetting for you? Because you don’t. Or I think if you look at.

Lindsey Mignano:

There was another female tech platform that did, like, beauty services. I think her name was Melody, who did it. And she was talking about how when she went to VCs, they would say, well, I don’t think my wife would, you know, use that.

Melinda Wittstock:

I’ve had that too. I’ve had that. I even had a guy say that to me about the AI in. In. In. You know, our AI underpins a whole podcast platform, like, with 6 million podcasts. Say, like, yeah, I’ll talk to my wife. Like, is your wife like, in AI? I mean, is she in.

Melinda Wittstock:

Yeah, I mean, she. And does she. Does she have any background in like, you know, ad tech?

Lindsey Mignano:

There’s no reason to like to involve anybody else. If you just look at the hard numbers, right, that the founder and really double check the numbers in theory of like, the scope of how much you think you’re going to acquire of that market and what are the next milestones to get there?

Melinda Wittstock:

Right.

Lindsey Mignano:

Like that’s. In theory, all of that is still kind of up in the air at the seed stage anyway. But, like, there is diligence you can do. I think what you’re finding though is like that female investor unfamiliarity problem or hesitance is the same as the same as the male investor unfamiliarity, hesitance. And people don’t like to take risks. Sometimes on verticals they don’t know, or they can’t tell their LPs they’re deeply familiar with.

Melinda Wittstock:

Right.

Lindsey Mignano:

And as an LP in a venture fund, you would want to have your money deployed by the GPS in that fund because The GPS can vet those companies really well because they did that before.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like from an investor perspective, as an lp, you kind of do want that. They do have a fiduciary duty to their LPs, and you want that experience. If I invested in an enterprise AI fund that suddenly started deploying money into wellness AI tech, while I would love this as a consumer, I would also question whether or not they had the ability just between them to really vet those deals. Do they have market understanding? And they may not. And then your suggestion comes into play. It’s like, well then did they hire a principal or a partner on a deal by deal carry scenario where they could, could just go in and vet this deal properly? Hopefully maybe they did, but I think that’s what they’re pushing up against.

Melinda Wittstock:

Yeah. So, like just with zero limits capital or it’s a, is a new fund, we’re really focused on, you know, female founders and just our whole diligence process is very deep. And having done a lot of diligence in a lot of our deals, I mean I literally will just call people I know in my networks. Do you know what I mean? Like, but also there’s a way to do the research and test it out. So, like we go really deep in the diligence. It’s, it’s, you know, it’s quite a process. But that’s also because of the, you know, the background and valuation growth, you know, for like 470 companies and just really understanding that. So, like there is a way to do it, but it does require work.

Melinda Wittstock:

Like you actually have effort and it’s.

Lindsey Mignano:

Sometimes it’s just. And this is why I think there are some, there is some bias to these verticals. It does require work. It does require double checking someone’s numbers. It does require getting caught up to speed on a new vertical that you don’t invest in generally and that some people don’t want to do that. Like, some people are just like, nah, why would I stretch and do wellness AI when I could just do hard tech AI, which I’ve known for decades.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like that comes down to that.

Melinda Wittstock:

It comes down to that preference.

Lindsey Mignano:

Yeah.

Melinda Wittstock:

Also, just that holds, I think women back in particular in raising money is, it’s such a relationship game. And if you didn’t go, go to Stanford, Harvard, MIT, if you don’t know personally a bunch of VCs, if you’re not kind of in that club, it can be really hard to even break into that club and like develop those relationships before you need the money. Right. So, talk to me a little bit about that. Like what’s the best strategy there? If you’re, if you’re not in the club but you have something that could be a billion-dollar business, you know, it’s, you’ve ticked all the boxes, but you don’t have the relationships.

Lindsey Mignano:

And this is what’s so hard, both for female founders, but also for black founders, for Latino founders, from founders who live abroad, is those relationships do matter at the end of the day. And the understanding of who is the guy. It’s usually a guy at this firm who cuts the checks, like who actually has a decision-making power here. Am I in the room with that guy or am I in just a room with some principal or associate at the firm who’s going to present this on a Friday, be steamrolled and tell me later on that her boss said, no, we’re not going to invest in you.

Melinda Wittstock:

Right.

Lindsey Mignano:

So, there’s two things, it’s like, are the, do they understand who they’re talking to at the venture fund?

Melinda Wittstock:

Yeah.

Lindsey Mignano:

And then. And where that person sits on the.

Melinda Wittstock:

Totem pole, you get a lot of like associates and all that stuff. And the other thing too is God has, I can’t tell you how many funds that I’ve pitched to over my five startups where the fund wasn’t even funded.

Lindsey Mignano:

Yeah. And that’s, it’s a waste of everyone’s time. So, there’s that.

Melinda Wittstock:

Right.

Lindsey Mignano:

And then how can they get in the room with the people who actually do have the check writing power?

Melinda Wittstock:

Right.

Lindsey Mignano:

Like how do they do that? And that’s been hard for again, foreign founders, people of color who are founders, women founders. Because when you look at those rooms, especially in 2025, when the attention to diversity issues is less, generally speaking, and you see who’s at those dinners, generally speaking, it is white and South Asian male. And that is who you know are socializing with each other over a dinner that the venture firm is hosting. And there are less female founders in there, which some, maybe they would argue. The firm would argue. Well, that’s a structural problem. There’s not enough women in STEM to even invite to this dinner.

Melinda Wittstock:

Right.

Lindsey Mignano:

But that aside, it still is a very male dominated space. And I think female founders have a hard time breaking into that based on a number of reasons. Yes, Ivy League and yes, location matters, but also the dynamics between female founders who are looking for money and male GPs who have check writing power and socializing outside of work hours, which no one talks about, as you know. Could this be problematic?

Melinda Wittstock:

While it was in Silicon Valley’s history, there’s a lot of, is he gonna…

Lindsey Mignano:

…Try to date her when all she really wants to do is get his financing? Like there are, you know, there are, there is a dynamic there, a heterosexual dynamic and a power dynamic that is, that is not to be ignored. Like, you can’t ignore the fact that we are dealing with maybe a 20 something or 30 something woman asking money from a man who is only, he’s the only person at the firm who can green light this, who is married in 55 or something like that. Like there is a dynamic there that makes it more uncomfortable for that female founder and more uncomfortable for, let’s say he’s an upstanding, happily married man. For that man, you know, like it is still there. And our female founders talk with us about it, you know, off the record, as uncomfortable. I have, you know, my husband used to be a partner in a venture capital firm. It was uncomfortable for him.

Melinda Wittstock:

Right.

Lindsey Mignano:

Like, you know, you want to be more careful with how you socialize with those possible female founders so that you’re not perceived as sexually harassing them or, you know, as a, as a male partner at a, at a VC firm. Because the power dynamic is still a problem. And I think there’s been some law, employment wise, I’ll have to look it up, but I think there’s been some employment laws that have covered that dynamic where, because there has been sexual harassment of these female founders seeking money in from their non employers, but From Venture Fund GPs who are male and older, there have been employment laws to address that situation. It’s not quite an employer employee situation, but all the right mix of what could go wrong is still there. Do you see?

Melinda Wittstock:

Right. So, Lindsay, as we start to wrap up, I, I wanted to tell me a little bit more about the type of clients that are your ideal clients and who you work with and like, what kind of, what are you looking for in a client? For anyone listening to this, a lot of entrepreneurs, a lot of female founders who are like, oh God, I just need the trick. I need the right people; I need the right relationships and whatnot. Who do you engage with and what’s the best way? If someone says, oh man, I need Lindsay’s help, I need her in my corner.

Lindsey Mignano:

Yeah. So, here’s the thing about being lower priced. We come in at one third, you know, the cost of a big law firm in terms of like hourly rates. So, if they come in at 900 to $1800 for associates versus partner time, and we come at 550 or 650 an hour, we’re naturally going to be lower cost. Like that’s what that means, is that we can, we at SSM can be pickier about our clients, right? We can say, because we know we’re going to win the deal economically on that basis almost every day of the week. And that’s purposely a part of our business plan to be lower cost than Big Law. Because of that, we can be pickier about who we work with. And we really like people who of course are great entrepreneurs, serious about their business, have integrity, but we, we really like founders who are good people.

Lindsey Mignano:

And I know that’s really hard to quantify.

Melinda Wittstock:

No, I know, I know exactly what you’re saying. I mean, that’s very much the ethos of zero limits capital as well. Like, it’s kind of like people first, right? Because you’re really ultimately investing in the.

Lindsey Mignano:

People when things get hard. And it will get hard with your lawyer or your CPA if you have a tax problem or if you have a co-founder exit problem or you have a situation that’s hairy and thorny and hard to understand, we as lawyers want clients who are like gonna give us that extra attention of like, let me understand what you’re saying because it’s important, but let me ask you the right questions because I also don’t understand it, right? Like, we want that back and forth and that is relational. We want clients who are going to, you know, take the time to get into the nitty gritty with us about why something is actually really a big problem, right? And not every client is like that. We have tons of clients, you know, who maybe are former clients who were like, whatever. We’re not going to tie out that cap table before the raise where we’re like, nope, can’t represent you now. Just stuff like that where we’re like, we just don’t, you know, we don’t, we don’t do business like that. So, we have a preference for founders who are like just people who are really trying their best. Because when we find that they really, really are, are very invested in their companies and they’re trying their damnedest and they’re really nice people, we do really good work with them.

Lindsey Mignano:

The, the form of communication is collaborative, collegial, it is kind. It understands that everyone’s a human, right? We tend to dislike, and we will fire clients who are rude to my staff who constantly double check us because maybe they didn’t really want a female lawyer to begin with. And you know, who are only hiring us for cost, but really don’t believe in the mission of the firm or the expertise of my staff. And my staff is predominantly female and people of color. So, we take that really sensitively. Like we’re aware of the prove it again bias that happens to people of color and women in leadership positions. And if we find that our clients don’t really respect our opinion or don’t take our advice seriously, then we’re probably not the right fit for them either. But it’s.

Lindsey Mignano:

It’s hard to quantify. I’ve run that past my husband a couple of times when I’ve. When I’ve had to unfortunately let clients go as to, like, the reason why. And he’s always been like, but they pay you. And I’m like, yeah, but it just doesn’t feel like good money at the end of the day because you can work for so many clients. Why not work with the ones that you love?

Melinda Wittstock:

Yeah, 100%. I mean, I completely hear you on that. So, I’m just going to make sure that I have everything in the show notes for anyone who’s listening to this that’s looking for their kind of corporate lawyer to get in touch with you. Lindsay, I just want to thank you so much. What an illuminating conversation. Thanks for putting on your wings and flying with us today.

Lindsey Mignano:

Absolutely. Thanks for having me. And if anyone wants to reach out, I’m. I’m on LinkedIn or they can find me on social media or email is fine.

[INTERVIEW ENDS]

Melinda Wittstock:

Lindsey Mignano is the founder of SSM Legal and the founder of Venture Betches and Syndicate Betches, a venture fund of fund and real estate syndicate fund of fund dedicated to women and BIPOC investors.

Melinda Wittstock:

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Melinda Wittstock:

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