1000 Naseem Sayani, Clare Baukham, Deborah Sass, Lindsey Mignano, Rajia Abdelaziz, Trixi Castro, Ungenita Prevost:

Melinda Wittstock:

Coming up on Wings of Inspired Business:

Rajia Abdelaziz:

I’m going to be as selective about you as you are about me, because I’m going to end up making you millions of dollars. And that’s going to change your life and your fund as well. So, I want to make sure that you’re a good person and your mission and your morals are aligned. It’s not just you looking at, hey, do I want to invest in her company? I’m like, do I want to do business with you? Do I want to make your fund a lot of money? And that changes the power dynamic. 

Melinda Wittstock:

Almost a decade ago, I started this podcast because I wanted to change that exact power dynamic to accelerate the inspiring innovations of female founders, who still to this day receive less than 2% of all venture capital investment. Rajia Abdelaziz is the founder of invisaWear and one of seven extraordinary entrepreneurs and investors joining me today to celebrate episode 1000 of Wings of Inspired Business. Why did I call it Wings? As founders, we must transform like the butterfly. See through the dark like the owl. Fly backward when we must, and love the flight, like the hummingbird. Soar like the eagle. Every female founder I’ve met has needed inspiration from all four, usually in the same week. And “inspired”? It literally means breathed into. The best entrepreneurs don’t wait for an idea to arrive fully formed. They stay open enough to catch one mid-air, and brave enough to build it. So today we take flight to see how far we as women have come in the past decade and where we’ll be ten years from now.

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 believe in paying it forward, so as a five-time serial entrepreneur, I started this podcast almost 10 years ago 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. Please take a moment, hit subscribe so you never miss an episode, tell your friends and colleagues, and we appreciate it when you help this wisdom get discovered with a 5-star rating and review. 

Melinda Wittstock:

So, here we are, 1,000 episodes in, and what has changed? A lot, and not much. Gender disparities persist in access to capital, networks and opportunity, yet the successes of women entrepreneurs are now getting impossible to ignore. When I started this show, it felt like women were succeeding in silence. So, let’s yell some of these numbers from the rooftops: Women founders on average deliver 2.5 times better returns than male-founded startups, despite the fact that women’s share of venture capital dropped below 2% this year.  And according to Boston Consulting Group research, women-founded companies generate 78 cents of revenue per dollar invested compared to 31 cents for male-founded companies, a funding gap representing a missed economic opportunity estimated at over $5 trillion globally. Meantime research from PitchBook and Harvard’s Kennedy School variously show that women drive 10% higher cumulative revenue over 5-year periods, exit 6 months faster than men, and in 2024 comprised 24.3% of the total US venture exit count. Not surprisingly we also do more with less, burning 15% less capital than men. And some 13 female founded companies achieved billion-dollar Unicorn status in 2024. 

Melinda Wittstock:

So, bottom line, we’re good at this. But we’ve still got a long way to go.  Imagine for a moment what sort of investor returns all those VCs would be getting if women had 50% of the money? The innovations that get funded are shaping our future, so that means women need a much bigger share of the money, but also a much louder voice on where that money goes. Today we talk about the systemic changes needed to transform the entrepreneurial landscape for women, inspire more women to invest in other women, overcome societal biases and mindset issues that can keep us playing too small a game, and along the way create a more equitable, inclusive, and high-performing business ecosystem.

Melinda Wittstock:

So, who better to join me today than six inspiring women you may have gotten to know on some of my favorite Wings episodes. Clare Baukham is a Global Wealth Architect, alternative investment curator, serial entrepreneur, executive producer of multiple TV series, and creator of The Billionaire Woman platform. Ungenita Prevost is on a mission to help 10,000,000 women build social capital and monetize their networks as the leader of a global feminine leadership network also busy building her new beauty brand Ungenita Beauty. Deborah Sass is a serial entrepreneur and the CEO & Founder of SpaceVrse, a global space ecosystem connecting industry leaders, innovators, creators, and next-generation talent across more than150+ countries. Her work focuses on shaping how space is communicated, commercialized, and culturally understood — beyond borders, sectors, and silos. Trixy Castro is a visionary entrepreneur in real estate and mortgage finance having founded, scaled and sold multiple businesses, including private lending company Genesis Capital, bought by Goldman Sachs in 2018. Passionate about empowering women to excel in business, Trixy has founded and invested in over 50 companies across diverse industries and is now the CEO and Founder of TRX Capital. Lindsey S. Mignano is the founder of Mignano Law Group, an entrepreneurial Silicon Valley corporate lawyer representing emerging technology companies and industry-adjacent firms and small businesses.  Her practice spans technology company business formation and expansion into US markets, M&A (flips, entity or asset sales), commercial and technology transactions, and venture financing. And Rajia Abdelaziz is the CEO and co-founder of invisaWear, a company at the forefront of smart jewelry and life-saving technology. An advocate for women’s and children’s safety, Rajia scaled invisaWear to reach over 100,000 customers, successfully raised millions of dollars, and earned coveted recognition including Forbes’ 30 Under 30 North America, Boston Globe’s Tech Power Players, BostInno’s 25 Under 25, and the New England Innovations Award.

Melinda Wittstock: 

We’ll put our Wings on to fly with these inspiring women in just a moment, but first we hear from a female venture capitalist, Naseem Sayani. Naseem is founder and CEO of GCWC and GCWC Capital, a media platform and investment fund focused on tech and AI-anchored innovations across HealthTech and FinTech. Naseem shares my mission to get more women writing checks. She’s a dedicated ecosystem builder, who also leads the Innovator’s Circle at WHAM, is an Advisor at Tower Capital, and hosts The Capital Flex, a podcast focused on the fundraising experiences of female founders. 

[INTERVIEW A – NASEEM SAYANI]

Melinda Wittstock:

Hey, Naseem. Welcome to Wings.

Naseem Sayani:

Thank you for having me. This is great.

Melinda Wittstock:

So excited to talk to you because we met, oh god, I don’t know, a couple years ago.

Naseem Sayani:

A couple years ago.

Melinda Wittstock:

And we shared this mission of how can we change the game for female founders, but also get more women involved in investing. And this was the mission of this podcast, like, over the past 999 episodes? And why I started this was to catalyze this ecosystem. What was the spark or the genesis that made you want to really change the game for women? VCs, women investing, supporting female founders.

Naseem Sayani:

Yeah. It came out of my life, at the consulting firm where we then built a product studio, which then grew up into a venture incubator. I was doing all digital strategy innovation work, and this was early 2000s. Silicon Valley was moving kind of in parallel to what we were doing. And we started to find that our clients couldn’t build product. They didn’t know what UX, UI, tech, etcetera, didn’t mean anything at the time. So, we launched a product studio to help actually build experiences, and then those products ended up needing different governance, different KPIs, different leadership.

Naseem Sayani:

So, it grew up into a full venture incubator, and the proposition became instead of just building product or building a startup, we’re actually going to build a startup that would otherwise put you out of business. And that’s what we were talking to our clients about, which was tremendous. This is 2012, 2013. Right? So, we’re still kind of Uber hasn’t landed in New York City yet when we’re doing these things. And so, it’s wild west.

Naseem Sayani:

And what I saw most two things happened once we were now building startups was one, there were not enough women in the room. And so, when you’re starting to do observational research and insights and pulling data together on what features something needs, if you don’t have a variety of voices in the room and a variety of lived experience, you miss entire categories of opportunity and growth. You’re just not building for it because you don’t know because it’s not the lived experience of the people in the room.

Naseem Sayani:

So, I went looking for them, spending my extracurricular time trying to meet female founders and trying to convince them to say, hey, I’ve got this CEO job at this great startup. Why don’t you apply? You’d be perfect for this. None of them wanted anything to do with it.

Naseem Sayani:

They’re building their own companies. They’re very happy being independent and building what they want to build. And it is in that dynamic that I also I realized or saw more acutely the huge differences in funding, in resources, in ecosystem, in networks that sit around female founders in contrast to what sits around our male counterparts. And that just became too hard to live with. It was it was such a stark contrast when you have incredibly talented people over here also building, also hustling, but cannot access the same things that simply by being a male founder, you have all of these organic things around you. So, I decided that I needed to redirect my energy and my expertise and my knowledge of building towards the female founder half of the ecosystem. And while I could do all the things in the stack, the last big piece was moving capital.

Melinda Wittstock:

Right.

Naseem Sayani:

And if I can be part of moving capital well beyond angel checks, I was writing angel checks. I love that, but it’s not system changing, and I wanted to be system changing. And so that’s why the stack had to include moving capital as well. And that was the leap into venture.

Melinda Wittstock:

All the male VCs talk about pattern recognition. And I have all this pattern recognition, funnily enough, from interviewing all these female founders. Yeah. All the things that we have to overcome.

Naseem Sayani:

We’re now building the communities we need in this ecosystem, and female founders are building networks of other founders around them so they can share notes and look at term sheets together and make sure that, you know, they can find predatory things before it happens to them. They’re we’re now doing more events that have more women in the room and trying to cross the gender divide. And we can spend a lot of time in rooms of just women, which is wonderful and fun and magical. But if we don’t cross the gender divides, we’re not optimizing the relationships. And two, we need that social capital to move so we can access the capital that’s sitting on the other half of the ecosystem. The big funds with lots of money are still led by our male counterparts, and we have to be able to build those relationships.

Melinda Wittstock:

And they do what feels comfortable to them.

Melinda Wittstock:

Like, a white dude in a hoodie; he must know what he’s doing. He’s dropped out of the right school, so, my money’s probably safer. And yet the stats completely belie that. Like, women are returning 78 on a dollar per invested, men off male teams, 31¢. Right. Women are getting access faster. They’re utilizing capital better.

Melinda Wittstock:

Actually, a fantastic stat is something like 33% plus of women led startups are exiting Yeah. Even though we’re getting less than 2% of the capital. Yeah.

Naseem Sayani:

Well, it’s such an interesting stat, that one in particular, because despite lower investment, those founders those female founders are still exiting more quickly and with more cost-efficient cash flows and balance sheets and run rates. And so, the one response I’ve heard is, oh, okay. Great. So even with not enough money, they’re still getting there. And you go, well, that’s not the takeaway. Could you imagine how much faster and how much bigger this business could be if she had funding? And if there’s more like her, just consider how much more, liquidity there could be on the other side if we were actually refunding more people like her. Right? That that should be the takeaway.

Naseem Sayani:

The first order business is getting women more connected to each other.

Melinda Wittstock:

Yeah.

Naseem Sayani:

Getting us back to a place where we’re in community and we know each other and we’re sharing and we’re in abundance and we realize again how much power there is in that. That’s baseline. Right? We’re doing that more and more with having communities of women do things together or have events together or actually spend time talking to each other for goodness’ sake. Without the guards up. Right? And we start there. I think that’s probably the most important starting point to make sure we can get after.

[INTERVIEW A ENDS]

Melinda Wittstock:

More from Naseem coming up later in the episode, and you can hear the whole interview with Naseem on a special Bonus Episode for our Wings 1000 celebrations out later this week. Make sure you also catch Naseem on the Capital Flex podcast, wherever you listen.

Melinda Wittstock:

Now let’s turn to our inspiring panel – Clare Baukham, Rajia Abdelaziz, Deborah Sass, Lindsey Mignano, Ungenita Prevost, and Trixy Castro.

[PANEL DISCUSSION]

Melinda Wittstock:

All right, ladies, you are all here because you are visionary entrepreneurs and investors, and like me, on a mission to really change the game for female founders. And by the way, over the last 999 episodes of Wings of Inspired Business over the past decade, you have all provided some of my most enjoyable and insightful and inspirational interviews. So, I want to just start by thanking you all. It’s great to have you.

Lindsey Mignano:

Thanks for having us.

Rajia Abdelaziz:

Thank you. Yay.

Melinda Wittstock:

Let’s start with a lightning round. I want you all to just introduce yourself, your business, your mission, and what’s inspiring you right now. Deborah, why don’t you go first?

Deborah Sass:

Thank you, Melinda, and congratulations on 1,000 episodes. That’s like a badass boss bitch. I love it. And a hand up to you for consistency.

Melinda Wittstock:

You know what? It’s fun and it’s easy because I get to talk to all of you.

Deborah Sass:

So, my name is Deborah Sass. Thank you very much for having me. I am the founder and CEO of a very unusual community because I am not a space person. I didn’t want to be an astronaut. I didn’t want to watch sci-fi. In fact, I have very little interest in the space industry. But I actually started 10 years ago as a female of color raising money. 

Deborah Sass:

But Spaceverse is a community online on all the platforms that has one job: to make the space industry more interesting and relatable to non-space people. We started 2 years ago with zero subscribers, and we are now about 17.5 million. So, there’s a lot of people out there all around the world that want to actually know about space. So, we gave them a place. That’s it. That’s me. I’ve done many other things. 

Deborah Sass:

What’s lighting me up right now is where we are going to be in the next 10 years for female founders. As I know, we’re going to go into this in detail. It’s not actually about the money. Almost $500 billion was invested in 2025 into startups. Less than 1% went to women. We’re going to talk about that in detail. It’s not about the money. It’s about the access.

Deborah Sass:

And I know that’s going to change. And we are a very small microcosm of how that’s going to change right here, right now.

Melinda Wittstock:

Amazing. OK, let’s see, Trixy.

Trixy Castro:

Thank you so much for having me, Melinda. And like Deborah said, congratulations, because what you have done with these 1,000 episodes and what you have— I mean, it’s a game changer. And I wish I had had you coming up in business, right? Because you become this role model for women and kind of this beacon of light of like, hey, I’m not alone. I’m not alone in this journey. There are moments when it’s hard, all of the things that we encounter as females in business. And so, thank you for doing that on behalf of all of us. Thank you. My name is Trixy Castro.

Trixy Castro:

I’m a serial entrepreneur. I started my first companies at 14 years old, and that was my ‘yes, you can’ moment, right? I realized, wow, there’s so much opportunity here. And really dedicated my life to trying to really provide real estate access, real estate investment opportunities to people, regional jobs, and founded some companies, had the great— with a phone and a desk, like complete entrepreneur. I had nothing going on. My first employee was a 14-year-old girl working for a prom dress. Then she gets the lead of the high school play.

Trixy Castro:

So, I hire her best friend.

Trixy Castro:

And I was like, what? Are you kidding me? Now, my phones aren’t even being answered. And my nephew, who I paid in gas money, took that little company, sold it to Goldman Sachs years later, have all the battle wounds, all the things, right? So, really dedicated my life to what I’m doing now, which is really encouraging other people as they’re in their journey and meeting them where they are. It’s a platform called Success Unlocked, and it’s all the things that little Trixy didn’t have coming up in business.

Deborah Sass:

Yeah.

Trixy Castro:

access, exposure, education, ladies like you guys, and just being able to say, hey, I’m your thought partner. I’ve been there. I get it. I understand. Be careful, pothole here. Heads up, maybe you can leapfrog here. And so, I think it’s just— it’s been so incredibly rewarding. Like you guys, I do lots of different things, but that is my core passion and being able to just grab other people’s stories and showing the audience, hey, look, here’s a yes, you can moment.

Trixy Castro:

And here is how they did it. And here is how we can do it together. So, it’s been a lot of fun.

Melinda Wittstock:

Beautiful. I love it. I’m going to hop over to Lindsey.

Lindsey Mignano:

Hi, everyone.

Lindsey Mignano:

I’m Lindsey Mignano. I’m the founder of Mignano Law Group. We’re a corporate law firm. I’m the owner, about 10 lawyers. We’re small and mighty. We generally serve series— C through Series B technology companies, a lot in California and New York, and mainly in the enterprise SaaS or PaaS AI space at this time. Happy to be here. Congratulations, Melinda.

Lindsey Mignano:

And I guess if there’s one thing that I’m really looking forward to, or that I really actually have been noticing in the past, say, decade or so, I now have men that work for me. I never used to. And it’s really great because, you know, in 2007, when I graduated from Stanford as a feminist studies major, there were 7 of us who graduated with that major. And we were all women. And women’s issues in 2007 was still considered a women’s problem. And I am so excited about how many men are leaning into these sorts of issues and discussing things that they would have never had before publicly, openly, and being really good, not only just mentors, but sponsors of people, especially in my industry where, you know, we’re still dealing with a predominantly white, predominantly male set of clients, set of investors who fund those clients, set of opposing counsel who do the deals with us. So, it’s really great to see that we’re getting a little bit better and making some progress.

Melinda Wittstock:

Fantastic. When you were on the show, Lindsey, you had so many stats about what was going on in venture so yeah, we’re going to tap you on all of that a little bit later in the conversation. I want to move to Rajia right now because, Rajia, you’re in an active raise, for InvisaWear. So, tell us a little bit about what you’re doing.

Rajia Abdelaziz:

Thank you so much for having me here today, Melinda. It’s so exciting to be among so many incredible women. I feel the energy is so exciting hearing everyone’s story. My name is Rajia Abdulaziz. I started my company 10 years ago by complete accident while studying engineering in college. I was at a networking event, and I decided to leave a little bit early. At first, I thought to myself, maybe I should ask someone to walk with me back to my car, but I really didn’t want to inconvenience any of my friends and it was parked less than a block away. So, I said, I’m being paranoid.

Rajia Abdelaziz:

I need to stop watching so many news stories and listening to all this true crime. I ignored my gut instinct and started walking back to the car. As I was halfway between where the event is and where my car was parked, An SUV full of 4 men drove by. They rolled down the window, started yelling inappropriate comments. The car stopped, and one of the 4 men started to get out. I had my phone on me, but what can you do in a situation like that? You can’t really say, hey, don’t hurt me. I’m just gonna grab my phone, unlock it, dial 911, tell them where I am, what the emergency is. Obviously, that’s very unrealistic.

Rajia Abdelaziz:

They’re going to take your phone and slam it to the ground. I ran as fast as I could, and thankfully I wasn’t hurt. But for hours later, I was shaking uncontrollably because all you see on the news is really horrible things that have happened to women, and I was so lucky that I didn’t become that next morning’s news channel. As I was looking for safety devices to protect myself and my loved ones, all I could find were big, ugly panic buttons that even my 80-year-old grandmother refuses to wear. She says she’d rather fall and not be able to get up than to be seen wearing a big, ugly panic button. I don’t blame her. I did what any other true entrepreneur would do. I declined the 6-figure job opportunity with Google to start working on invisaWear full-time.

Rajia Abdelaziz:

I ended up raising $3 million to develop the technology. Everyone told me less than 2% of venture capital goes to women. And I looked at them and said, so what makes you think I’m not part of that 2%? And what makes you think that when I become a part of that 2%, I’m not going to make it my personal mission to change that narrative? We since bootstrapped to becoming one of the fastest growing startups in America. We’ve done over $30 million in revenue, which is a really exciting milestone. Had the great honor of being on the COVID of Forbes 30 Under 30 a couple years ago, and I’m so excited to have this very important conversation with Melinda and you ladies. Thank you so much for having me.

Melinda Wittstock:

I’m so inspired by your story, Rajia. If you haven’t figured this out, she’s unstoppable.

Rajia Abdelaziz:

You’re so kind.

Melinda Wittstock:

Okay, Ungenita, over to you. We talked ages ago about starting a fund together, just a little, you know.

Ungenita Prevost:

Oh my gosh.

Ungenita Prevost:

I have to say this. I’m Ungenita Prevost, and I met Melinda in person. So, I don’t know how many of you met her in person, but she is the same amazing, generous person in person as she is in public. So, it was just so amazing. We had lunch together when I was in Los Angeles. I no longer live in Los Angeles. I live in London, and I’m so grateful that you invited me to this event. 

Ungenita Prevost:

I am a former foster child. I was aged out of the foster care system at 18. I went on to work in beauty and fashion, and then I segued into the entertainment business as a dancer, actress, most noted for being a very famous body double. And then when I went into the entrepreneurial space, I created brands such as Selling in Stilettos, Networking in Stilettos. When I was on Melinda’s podcast, I had a community of 24,000 women, and the goal at that time was to help women build social capital. I met so many women who were raising money, and one of the defects that I saw, and I wrote a book about this, Networking in Stilettos. I have a podcast that’s still out there, but I’m actually launching a new one. But most women don’t focus on social capital. They want the financial capital, but they forget about building the relationships.

Ungenita Prevost:

And so, I was in the entertainment business. And so being in the entertainment business, you know, it’s all about relationships. It’s who you know, right? You know, how did I get to be a body double? Because I met the number one casting director in Hollywood. I went on a dance audition, and he said, you know what, I’m gonna make you her double. I won’t tell you who it was, but it was someone very famous. You can message me and I’ll tell you. But I thought, okay, that is what I’m here to do. I’m here to teach women how to build social capital.

Ungenita Prevost:

I’m here to show women what I did. I didn’t have a mother. I didn’t have a father. I was aged out of the system, and I’ve literally made the impossible possible. Well, this is what I noticed. Women weren’t interested in that. A lot of women weren’t serious about it. And I thought; you know what, perhaps this is my gift, but maybe it’s not a gift that I am supposed to teach women how to do.

Ungenita Prevost:

And I went back to my true love, which is beauty and fashion. I relaunched Ungenita Beauty. My focus now is ‘face the ugly’. And no, it’s not about how you look. It’s about life cycles that women find themselves in, those ugly life cycles— money, relationships, life, home, identity, body. That’s my mission right now, is to help women, because I’ve been through every ugly life cycle you can imagine. And then I have Ungenita Beauty, which is makeup, skincare, mindset, and presence.

Ungenita Prevost:

And that’s the sort of outside aspect of the brand. But it’s rooted in substance. It’s rooted in really being highly visible, but also owning your skills, talents, and credentials. And that’s me. And I’d love to connect with all of you. Like I said, I’m all about social capital, so please connect with me. I just— that’s just no longer my day job.

Melinda Wittstock:

Yeah, I love that though, because that’s one of the things that women I think we get spread too thin and we try and do too many things for too many people. And the thing that gets sacrificed is that relationship building. And that very much ties into the whole fundraising picture as well. But before we dive into all of that, last but not least, Clare. Tell me what you’re working on right now, but also your entrepreneurial background is astonishing as well.

Clare Baukman:

Thank you for having me. Hello, everyone. Nice to meet you all. Thank you for that. Yeah, because, you’ve all done so much stuff, but you’re probably high performers at heart. So, you’re like, yeah, but what else can I do? Right? So, you’re just like, push, push, push.

Deborah Sass:

Effort, passion.

Melinda Wittstock:

I see it in all of you, and I love it.

Clare Baukman:

But so, I have an extensive, interesting background of entrepreneurship and acting, and I owned a flower store and all of the things, options trading on the US markets and so on and so forth. I have multiple businesses like most of you. Um, I used to be a traditional financial advisor, but my heart wasn’t in that fully anymore. My heart was in, yeah, but how do the elite make the money? Because everyone else who’s working with a financial advisor is not making money the way the elite are. So, I basically was mentored by centimillionaires and billionaires, and I took their blueprint and started putting it over top of what I would love. And now I own multiple businesses. So, I have Clear Wealth Group, which is more of a traditional financial advisory practice in a way. We’ve kind of changed our model.

Clare Baukman:

I work with high performance and like CEOs and athletes. That’s just something that’s in my heart from a very long time, from basically when I was a child. But I think what Melinda’s alluding to is my business Clear Art Reserve, which is what we discussed when I was chatting with you last time. So Clear Art Reserve, basically, you guys all know Andy Warhol, the painter, the artist. So, Andy Warhol, for example, there’s a $2.5 million Andy Warhol painting. We’ll basically— whenever I say that to someone, they’re like, well, I can’t put a $2.5 million painting in my portfolio. That’s ludicrous. And I’m like, yeah, but 5 years later, that Andy Warhol sold for $28 million.

Clare Baukman:

So basically, what we do is we buy the Warhol and we sell shares to everyone. So that’s what Clear Art Reserve does on one side. And then on the other side, just naturally, we got into doing high-end portfolios for family offices. And a lot of people, like a lot of you who have done an exit and you’re like, you know what, I need art in my portfolio, but I don’t have a proper management and stewardship company. It’s just that, you know, when the things just kind of come to you and you’re like, yes, this is a yes for me, then. So, we just started to do that. Um, what’s, what’s really calling me these days is identity, the ability to basically shape-shift. I think especially women, we have this ability to say, you know, that’s not me anymore.

Clare Baukman:

We’re moms or wives or girlfriends or whatever, and that’s not me anymore. And we have this ability to kind of cocoon in ourselves and become this whole new butterfly.

Rajia Abdelaziz:

Mm-hmm.

Clare Baukman:

So, there’s this, this beautiful ability in all of us. And I think that I’ve just seen so much in myself and in my clients that anything is truly possible. And you are all— you’ve all seen that. You’ve all done it. So, I don’t have to tell you.

Clare Baukman:

I’m already inspired just listening to all of you. I’m very happy to be here.

Melinda Wittstock:

Yeah. Oh, wonderful. We’ll get into entrepreneurial origin stories. When I think back to when I first had this inclination to go and sell something, I was— I hadn’t even turned 6 yet. And I went door to door demanding prepayment for my show. 

Melinda Wittstock:

So, my show, it had like costume changes and like spotlights and like my Barbies with sprinklers, like all this stuff, right? But it, it never occurred to me that people wouldn’t come. I don’t know where I got the idea of prepayment from, right? And there was just that thing in inside me. And over the years, at different times, there was so much effort of society or whatever, and sometimes I got brainwashed by it to get rid of that impulse, right, in the little girl who couldn’t be stopped, where you, you kind of psych yourself out or, or whatever. This to me is a really big part of what can hold us back. It’s that kind of inner game where we get kind of brainwashed by what we’re supposed to do or what we should do or what we think we deserve. And looking around at society at the moment, when women are suffering from imposter syndrome, I think we should throw that right out because we can just look at the US Congress or we can look at any of these people. There’s just no excuse, no excuse for imposter syndrome anymore. So, tell me, in your life, if you could pick any moment of your entrepreneurial journey, was that there, that moment where you thought, wait a minute, I’m psyching myself out? Like, who is this? What’s my inner pilot light like to find myself again and just like be— not let anything get in the way, I guess? Who wants to take that on?

Ungenita Prevost:

I can. 

Clare Baukman:

Yeah, I think I’ve had so many. I was about to buy an advisor’s book way back for like $200 million. He was managing $200 million and I had just had my boy and he looks me up and down and I said, well, let’s get going. Let’s get the deal done. And he looks me up and down and he says, why? You’re not pregnant again, are you?

Clare Baukman:

Like, there’s been so many. And this isn’t like a male-female thing for me. It doesn’t matter if it was a male or female. It just, there’s been so many little pinch points for me along the way. But I think that those pinch points have, because you, when you’re open to receiving those, you, you let them guide you, right? And that’s how I think I love that story of when you were a child. When I was like 4, you know, they say rock stars, the rock stars like, oh, I’ve been playing guitar since I was 4 or 5 years old. Mine was watching people and their behavior. And that’s 100% from my childhood of growing up in a household that had some turmoil with an older brother who was different.

Clare Baukman:

And I think for me, it’s always been along the way, but there are some definite massive pinch points, or I would say inspirational points that pushed me further.

Melinda Wittstock:

Right. One of the reasons I started this show to begin with was to destigmatize those moments of failure or those moments of isolation where you feel like you’re the only person who doesn’t know, or like, you know, these are all real for everybody and like people don’t talk about them because we’re all supposed to be, you know, outward basics, you know, have the perfect Instagram reel, have the perfect story and all of that. But like, entrepreneurship is about failure, like all the time, right? Like, and, and it took me a long time to understand that because I thought, oh my God, I’m the only one that hasn’t been funded, or I’m the only one who has, right? All of that. So psychologically, I mean, if you’re— any of you are willing to share, like, what’s a dark moment, I guess, in that journey? Where maybe it was the dark moment that actually made you?

Ungenita Prevost:

Oh, I would love to. Face the ugly. I think my dark moment was when I was down to $52.27. And I was moving out of my apartment in Marina del Rey. And I was moving in with my girlfriend. And I barely had the money to pay the movers. to move me from Marina del Rey to Woodland Hills. And I still have the bank slip, $52.27.

Ungenita Prevost:

And I remember in that moment, I mean, I was ashamed, I was scared. You know, I was aged out of the foster care system at 18. So, you know, I couldn’t, like, run home. You know, I didn’t have the family support. And in that moment, something said, save this bank statement. You’re going to get over this, and this is going to be a big story.

Clare Baukman:

Mm-hmm.

Ungenita Prevost:

And within, I guess, maybe 6 months, I got my house back. You know, I was making, you know, over 6 figures. I mean, it was just crazy. But at that time, I needed to fall to build myself back up because I was coming out of a marriage. And, you know, he did some things financially that were not in my favor. So, I needed to fall. And one of the things I want to really highlight, because I noticed this in the entrepreneurial space, when a woman is failing in public, women have a tendency to sort of, you know, sort of give her the side eye like, ooh, you’re making a mistake.

Rajia Abdelaziz:

Mm-hmm.

Ungenita Prevost:

You’re not that great. Oh my God, how did— oh my God, the gossip. Oh wow, you know, oh my God, your launch failed. Oh my God, your business failed. Oh my God, you didn’t— and it’s really sad because the women that step up to the plate are the women who change lives. You know how many lives I’ve changed?

Deborah Sass:

Yeah.

Ungenita Prevost:

Because $52.27, 24,000 probably more, but 24,000 is documented on LinkedIn. And so, for me, it’s about dealing with the shame and the embarrassment because a lot of women, they will not go any further because they, they can’t face it. And so, for me, in that moment, that’s when I realized what I was made of.

Trixy Castro:

Right.

Ungenita Prevost:

It was the $52.27 because you can’t mess with me because guess what? I’ve made so much money since that day. I’ve done so much more with my life since that day. There’s nothing, there’s nothing you can, you, you can say no, you can reject me, but I have the power because I know how to overcome. And I think that’s the skillset, especially when raising capital. You have to have the skill to take the rejection, take the embarrassment, and overcome it. Because on the other side, that’s the victory, and no one can take that away from you.

Melinda Wittstock:

100%.

Deborah Sass:

And it’s all about resilience, isn’t it? You know, when you have that resilience— I actually gave my first TEDx talk about resilience, and it was a really interesting subject because, I mean, I don’t really have that story of rags to riches. I grew up on a council estate. That’s like the projects in America. But I had a great family. We were poor, but it didn’t— you know, you don’t know this when you’re a kid. You don’t know you’re poor. You don’t know you’re a different color. You don’t know that you’re different.

Deborah Sass:

You just keep moving forward, right? And I think my aha moment was— I mean, it’s actually a funny story, but it, it was so poignant. When I first moved to America 20 years ago. I go to a very fancy party, and somebody looked at me and went— very good-looking guy— went, so where did you go to school? And I said, oh, I went to school in Australia. And I swear to God, this American guy looks me up and down and he goes, you’re the first Aboriginal I’ve ever met.

Deborah Sass:

Like, and in my mind I’ve gone, wow, you’re American, you know the word Aboriginal, that’s incredible. But that, that’s not really the full story, but it was just funny. But Madeleine Albright said something that we all know because we’ve all lived it, for whether we’re in our 30s, our 40s, our 50s, or even our 60s. There is a special place in hell for women that don’t support other women in business. And that, I mean, it gives me goosebumps just talking about it. I’m a serial entrepreneur. I’ve been hustling for 30 freaking years. And you know what? I will always, always support other women in any freaking way I can.

Deborah Sass:

They’ve supported me in the past, they’ll support me in the future. And that, like— and I know it’s that thing about women and men, but we are still having these podcasts, we are still having these conversations because that shit ain’t equal. And it doesn’t matter what color your skin is, it doesn’t matter where you were brought up, it’s still not equal.

Melinda Wittstock:

100%.

Deborah Sass:

Sorry, sorry for that passion.

Rajia Abdelaziz:

No, I love that.

Trixy Castro:

I think we can all relate to it. I mean, I can share. For me, there was— I don’t know how it was for you ladies, but for me, there were so many awful moments. There were so many down moments. There were so many, like, and we could go on for 5 hours and I can just tell you, like, year one, you know what I mean? Um, but I think what for me was Something that stood out to me always was being able to go back to a decision I made in New York, interestingly enough. I mean, look, I started the companies with nothing. I grew up in a guest house. My parents came from Cuba.

Trixy Castro:

My mom answered an ad in a newspaper job for a live-in housekeeper. So that tells you how bad things were that she moved me, my dad, and her— I’m 2— into complete randoms’ guest house. To your point, Deborah, I thought, well, I don’t— look at what they have, we must be rich, this is amazing.

Deborah Sass:

I saw—

Trixy Castro:

Wow, look what’s possible, right? They’re an Italian immigrant family too. And then I started to realize, wait a second, my parents work and that doesn’t translate into dollars, and they work really, really hard. And right, so it had that exposure moment. But for me, I remember having the company, got getting through all these different things, and I was like, you know, the mom, if you will. I was responsible for my little team that I told you guys about, and I had to go raise money, and I was private money lending, okay? And the demand was like $100 million, unheard of at the time, just with me. And I think I had a bag of like $10 million, right? So, you can only recycle the money so much.

Trixy Castro:

I saw the opportunity, but I saw what was possible. I had gotten this idea from being a teller at Wells Fargo, counting other people’s money and realizing, huh, these groups are making it in real estate, but they don’t understand the math, i.e., the leverage. What if we could scale their business. Long story short, go open up myself. I come to this moment where I’ve got all this demand, I have a real decision to make. Either I go raise this money quickly, which again, I can’t just make it little tiny bits of pieces, and I know we’re going to get into the capital raise, or basically I just call it a day and pack up my bags. And I flew to New York. I’d never been there ever, okay? This was not a very well thought out strategy.

Trixy Castro:

I had zero meetings, zero anything. I get in the cab, And he goes, where to? And I’m like, to Wall Street.

Ungenita Prevost:

Where?

Trixy Castro:

Uh, where the bull is.

Ungenita Prevost:

Honest to God.

Trixy Castro:

So here I am rolling my suitcase, okay? And I get to— and at the time there was this fearless girl.

Clare Baukman:

I have her here.

Trixy Castro:

So here, I’ll show you. Ah, they, they had her by the bull. I don’t know if you guys can see that. Oh my God. She was in front of the bull. Now she’s in front of the New York Stock Exchange, I think. And I remember having this moment Because we’re all taught you can’t cry, you can’t show emotion, you have to be strong, knuckle through, right?

Melinda Wittstock:

Right.

Trixy Castro:

Bawling in front of her, and it makes me cry now, and like vowing to myself, I am going to be that fearless girl for everyone behind me so that I can create access and exposure to them so that they can have a seat at the table. So, I’m willing to go take the tough hits so they don’t have to. And that’s how I mentally got myself through it. I will tell you, then it was like, okay, Trix, how are you gonna do this? You know that inner talk? I had to change it right there. That moment changed everything for me because it was like, am I gonna let that inner talk, the fear, all the things that were real— I legitimately was terrified, right? Or am I gonna be that fearless girl and say, hey, I’m gonna show the path to the next person? And truly, that is exactly how I started raising money, ended up raising $30 million on that trip, then got Oaktree for $250 million, and on and on and on. My point was who I became in that moment, it got me through the dark times. It’s what got me through the really bad trials when people steal from you, when they hurt you, when they viciously come for you and you’re like, but don’t you understand what I’ve been through? I just want to help, right? No, they don’t.

Clare Baukman:

They don’t care.

Melinda Wittstock:

They don’t understand.

Clare Baukman:

No, they really don’t.

Trixy Castro:

But it was like, that’s a ‘them’ issue. I want to be that fearless girl. I’ve got to start up here. And, I have to tell you, it changed my life because the tough times, became more learning moments rather than defeated moments, if that makes sense.

Melinda Wittstock:

Oh, it makes total sense. I was just going to say that certainly through my entrepreneurial career and so many of the women that I’ve interviewed and mentored and whatnot over the years, these challenges are sort of cyclical. I mean, earlier in my life, I thought, okay, I’ve figured everything out. And the minute you say, oh, everything’s figured out, that’s when you’re going to get some other lesson. I see them as lessons or learning opportunities. It doesn’t make them pleasant at the time, but trying to find some peace or self-forgiveness in those moments and not to fall into all the kind of shame or, you know, we’re all— I’m just gonna just wager that we’re all sort of Type A personalities here, right? Like we’re pretty ambitious.

Rajia Abdelaziz:

Yeah.

Melinda Wittstock:

We have big goals, huge visions. you know, all of this. So, it’s hard for that kind of personality to, I mean, it feels like it’s kind of a constant struggle. Rajia, I’m interested in your perspective because, you know, you’re much younger than all of us and you have so much of this ahead of you as well. Like, so how do you deal when things are going awry? Like, there’s a moment you can’t make payroll, or there’s a moment that something, something happens out of the blue, something you can’t control. What’s your mindset around all of that? How, how do you see it? 

Rajia Abdelaziz:

Like, how do you deal with it? I love this question. And honestly, one of the things that determines whether or not an entrepreneur is going to be successful is really their mental discipline and how they look at things. I know people like to say, is the cup half full or is it half empty? And that tells you a lot about how someone looks at the cup. The way I look at a cup is, is there a drop of water? Yes, there is a drop of water inside this cup. That’s a sign that whole cup can be full. Where do we get more water and where do we make a plan? And I think ultimately that’s one of the reasons I’ve been so fortunate to have a lot of success, like exactly What I was telling you earlier, everyone kept telling me the horrible thing. 2% of venture capital goes to women. You will never be able to raise funding to develop this technology.

Rajia Abdelaziz:

Why am I not a part? Why are you assuming I’m not a part of that 2 out of 100? Okay, that one of them and I’m going to help the next person be the 2. Then we’re going to come back and we’re going to change that to be 99. Then when I raised the capital, Melinda, everyone told me, you’ll never be able to make the product small enough where women would actually want to wear it. And then when 200,000 women started wearing my product, I was like, this is amazing. We’re getting so much traction. I’m going to reach out to ADT. They’re the number one name in home security. And everyone, Melinda said, you’re a tiny, tiny startup.

Rajia Abdelaziz:

You’re going to reach out to the number one name in home security. You think they’re going to respond to your email? Are you crazy? And within 3 hours, I had a response to my email. And within 3 months, we had a massive strategic partnership. Signed with them that exponentially grew our company. So, a lot of it comes back to your mindset and how resilient you are, which is the recurring theme that keeps coming up. I love this quote in particular. It says: businesses don’t fail, people quit. It’s how you look at the challenges and these terrible things that happen.

Rajia Abdelaziz:

When I was 21 years old and I was raising venture capital, people assume now that we raised millions of dollars and it was so easy and everyone was taking out their checkbook and saying, Rajia, here’s the money. What they didn’t see was the first 99 investors that looked at me like a child. And honestly, I was so young. So now a decade later, I’m like, wow, I really was a child raising funding. But essentially every single no, I didn’t go home and cry and say, this is horrible. No money goes to women. I said, okay, what can I learn from this experience? What tangible data can I use to improve to get one closer to a yes? But it could have been so easy for me to go back on the 98th no and say, we’re done, we can’t raise money. And I tried to be resilient.

Rajia Abdelaziz:

I tried to keep going in terms of business challenges. And sometimes the worst things that happen in your life end up being the best things that happen in hindsight. And you need to really remind yourself that when you’re in rock bottom, and you need to look at what good can come out of this and how can I use it to transform my life. I got chills when you were saying the $58 story. Most people would’ve looked at it with devastation, and you looked at it as, I’m gonna turn around my life and I’m gonna remember this moment.

Trixy Castro:

Right.

Rajia Abdelaziz:

I had same exact feeling years ago. I worked really hard to close a B2B order with a very large company. They ordered $2 million worth of product. We bought it all from the supplier. We’re about to ship them the order and one of the C-level execs calls me, says, we’re not gonna pay unless you give us a 50 or 60% discount. I’m like, what do you mean you’re not gonna pay unless I give you— we have a legally binding purchase order. I could sue you for this capital. What do you mean you’re not gonna pay me $2 million? And he said, well, you’re a really small company.

Rajia Abdelaziz:

It would take years by the time you sue me. I have the bigger— I could not believe something like that could happen. And frankly, that could have bankrupted our company because we would have owed all of the suppliers, the upright cogs. I remember thinking that was one of the lowest moments of my life, and I truly thought the company was gonna go bankrupt because of this this deal gone sideways. And I looked at that moment and I said, I will do everything in my power to fight and make sure this does not end my company. I’ve started brainstorming different strategies to come up with revenue. I completely redid the business model. I was aggressive about going after deals.

Rajia Abdelaziz:

And you know what, that one guy screwing us over is what led to the company becoming as successful as it And one of the things I wanted to also mention is I went back to a lot of our investors, which unfortunately the landscape with the current venture capital, a lot of our investors are males, which I want to point out that there are a lot of good men out there who do care about transforming this landscape. And I’m very thankful that a lot of our existing investors really are trying to give more capital to women. So, there are good men out there that are working for change.

Ungenita Prevost:

Yeah, I agree.

Rajia Abdelaziz:

But all of them at the time were saying, take the terrible deal, take the 50% of the money. And I was like, no, I will fight.

Rajia Abdelaziz:

If I have to take them to court for 2 years, I will get every penny we are deserved. And you know what? Did you? We were deserved. We got every single cent of that $2 million order.

Melinda Wittstock:

Ah, that’s inspiring. Lindsey, it’s a nice segue to legal. Because so many of the challenges that any business has, whether it’s male-founded, female-founded, is legal things that come out of the blue. Whether it’s like employment law, it’s just like, I don’t know, there’s just so many things that from startup, from idea stage to growth, that most entrepreneurs have no idea of, or they can’t necessarily afford good legal representation, or they just don’t know things about fundraising. So, from your perspective, of helping so many companies at various stages of growth what are some of the things that you see women doing right, wrong, like, like, you know, around this adversity kind of issue?

Lindsey Mignano:

What’s surprising is that I own a women-owned firm, and yet most of our clients are men. And that’s probably because of the sector that we serve, which is enterprise SaaS, PaaS, usually AI. And so, you’re going to get a harder technical space. That being said, one thing I think that female founders are more aware of is the stat that Rajia mentioned earlier, right?

Melinda Wittstock:

Right.

Lindsey Mignano:

They understand that when they have to go to a pitch, they’re going to be, you know, be asked more prevention rather than promotion-oriented questions. They understand that perhaps if it’s a product that affects only the health or the well-being of women, that male GPs, the people who actually have the controlling check-writing power in this fund and not their associate, you know, may not understand it or may not understand what the market, the real size of the market is, who would buy this, whether it’s a good fit for venture or not. I remember, so my husband is a retired VC. I’m a venture capital lawyer. It’s a great, interesting house to live in. And when I was first dating him, I remember he had asked me about a company called Stitch Fix.

Ungenita Prevost:

Oh, right.

Melinda Wittstock:

Yeah, I remember that. Yeah.

Lindsey Mignano:

Yeah. We’re both Stanford grads. So, it’s one of those things. She was also a Stanford grad a year above me. And it was circulating within our Stanford community. And would women actually pay for this? It was a very interesting conversation because it just showed the dichotomy of like what men think women would need or what they would buy and the purchasing power of that group. So, a lot of our female founders are incredibly aware of this. They’re not founders who don’t know what they’re up against.

Lindsey Mignano:

And I do think, you know, today we’re even seeing more bifurcation in terms of who’s getting funding and who’s not, right? Everyone knows the biggest tickets, the biggest dollars that came out of the SF Bay Area all went to big tech, big AI companies. little guys.

Rajia Abdelaziz:

Yeah.

Lindsey Mignano:

Of the little guys who got maybe 20 cents on the dollar, because that’s the ratio, most of that went to male or mixed-gender teams rather than all-female-founded teams. And of that proportion, a lot went to AI. And most of the founders, unfortunately, who are in the AI space are on all-male teams. It is very rare that we would see a female founder in a meaningful position of power, not just someone who, you know, is on the cap table and is added, for a university affiliation or, you know, some sort of perk, right? But somebody who has actually meaningful equity and a director role and a meaningful C-level role, that is less common than you think, even today.

Melinda Wittstock:

I’m gonna raise my hand because, like, I’m definitely in that. I’ve been innovating in AI since 2011. Back then, AI was, you know, natural language processing, unsupervised machine learning, a lot of pattern recognition, probabilistic modeling, all that kind of stuff fused together. And you know, across a series of startups, one of the biggest challenges for women like me is when you go to raise money from, like, so you’re competing against these big frontier kind of companies, right? Like, it’s very difficult to raise. It’s very difficult in that sense.

Lindsey Mignano:

Yeah.

Melinda Wittstock:

So, but people will say, well, go talk to the female VCs.

Ungenita Prevost:

Yeah.

Melinda Wittstock:

And you’re like, okay, that’s cool. But the female VCs don’t raise as much money as the male VCs, first off. So, their check sizes have to be, by definition, much smaller, which rules out a game-changing AI company, even if it’s like a verticalized, you know, verticalized AI or an application of AI or like just some sort of innovation, right, within an industry, transforming an industry with AI, say, for instance, whatever that is. They can’t take that on because they’re not gonna have the follow-on funds. So, there’s a lot of women with these sort of moonshots particularly AI, quantum, like, like really serious tech, really deep tech, who get kind of caught between these 2 things. And where do you go?

Lindsey Mignano:

And there’s still a bias with regard from taking capital as a female entrepreneur from a female venture fund, female-led venture fund. That is something that we don’t talk enough about. But truly, you know, we have had female founders take from women-owned VCs only for their next round for those VCs. And they are usually male GPs to be like, oh, Yeah, of course, she’s a woman, they’re a woman. And it discredits the entire purpose of that capital. It discredits the female VC who launched that micro fund to fund at the pre-seed stage or the seed stage. It discredits the female founder who got that. There’s an assumption that because you’re a female founder taking money from a female VC, it’s because you’re women, as opposed to it’s because her fund’s great and you’re great.

Melinda Wittstock:

The reason that I laughed so hard was it reminded me of a story. I remember doing a whole pitch. It was several companies ago for me. Okay. And seriously, this male VC said— and I was describing our AI and how it was working and whatnot in the context of my company NewsiT way back in the day. So, this crowdsourced news platform that had figured out how to rate the probability that crowdsourced content was accurate. So, a really difficult thing to do even now, right? And we were doing it. We had 500,000 users.

Melinda Wittstock:

And I swear to God, this guy said to me, ‘let me talk to my wife about that’. And like, innocently, I say, oh, is your wife in like AI? It’s just like, no, she’s like a housewife. Like, what? And like that kind of— excuse me.

Lindsey Mignano:

We’ve heard that story multiple times from female founders. That’s right spot on, especially if they’re doing something in FemTech or beauty or cosmetics or something where a man may never touch it. They’re just like, Stitch Fix, you heard of that? business, but you actually paid for it. You know, that’s part of the bias.

Rajia Abdelaziz:

Yeah, it’s really interesting you say that, Lindsey. And one of the things you mentioned is female entrepreneurs know that very well. Again, back to the story of when I was 21 years old with the first 99 investors that said no. One of the things I learned was it was how I was pitching the product. I was pitching women worry about their safety. 1 in 4 women are sexually assaulted. 1 out of every 6 women experience an attempted or completed And I kid you not, a lot of the feedback I was getting was people saying, women worry about your safety. I had one guy tell me his wife had never worried about her safety.

Rajia Abdelaziz:

And I’m like, did you ask her? And I kid you not, it took a lot of thought process on how do we tweak the pitch to get people who’ve never worried about their safety personally to understand the magnitude of the problem. And as soon as I learned how to switch the messaging and make it that person-specific problem, which I’ll explain in a second, every single investor was taking out their checkbook because now they understood it. So rather than saying all of these statistics and women worry about their safety, I switched the narrative. I said, one night I was walking back to my car after college and I was almost kidnapped. That could be your daughter, your granddaughter, or your wife.

Melinda Wittstock:

Self-interest. 

Rajia Abdelaziz:

Immediately, yeah, everyone is in silence. Take my money, Rajia. I need to be a hero. I need to protect my daughter. I need to protect my wife. You’re right. My daughter walks alone from college. 

Rajia Abdelaziz:

So, a lot of it, I try and encourage the young female entrepreneurs that I mentor is how can you make the story relatable? Or can you joke and say, go talk to 10 women and I guarantee you 9 of them will say XYZ? 100%.

Melinda Wittstock:

Well, it’s just like understanding the market. Like, so many men— I think this still happens— where they think half the population is somehow like niche, you know, like tiny. Or there’s, there’s a certain, like, I don’t know, you guys have heard of Dunning-Kruger syndrome, right? You can be really good at one thing, so you think you’re smart at all things. And I think there’s a lot of that in the venture community. I remember like the board chairman of several of my companies saying to me, Melinda, you’re making a mistake here. You’re assuming the venture people are smart, like, or that they’re educated or they know anything. Like, they don’t make the mistake of thinking that they’re smart or they should be in any way in judgment of you.

Melinda Wittstock:

And it was interesting that coming from a very accomplished male who’d built 6 of his own companies to high 9-figure exits and such, and invested in many. And it was a kind of a game changer for me because I think in the early days of my entrepreneurial career, I had this assumption that, oh, these investors must be so smart. They must know so many things. And so, when they said something to me or some feedback, I would take it seriously. And I would encourage people not to just take it seriously. 

Lindsey Mignano:

I think you’re right on, definitely on that. And I think that the problem is the power dynamic. Everything at the end of the day can come down to power. And the fact of the matter is, is that these men and these venture funds, even ones owned by women, are powerful in the Silicon Valley ecosystem. They are the giver of money. They are the holders of the pocketbook. They pull the strings.

Lindsey Mignano:

They say who gets minted with money and who doesn’t, right? And so, there is a natural inclination to want to believe that they are the be-all end-all of all capital when there are tons of alternative forms of capital out there, which we can get into, as well as that they are authority of your company, right? And it’s the power dynamic. And, you know, that saying, whoever holds the purse strings, it’s really that. And in economies, by the way, where it is not dependent on venture, my family was a poultry business from Waianae, Oahu. We are not dependent on venture ever.

Melinda Wittstock:

Isn’t that a lovely feeling to not be dependent on venture?

Lindsey Mignano:

No one understood, like, why this reverence for these people who don’t even do this type of work. They just manage money. and helping you grow it as an LP? Like, why is he now the expert on my AI startup or my life sciences startup or whatever, right? And that’s not to shade people in VC. I think there are tons of really smart people in VC who really know their particular sector and who do a great job coaching startups. And we know a number of them, and we try to send people to them as much as we can. That being said, you know, I do think that there’s a dichotomy as far as like the power and why their voice is so loud in this industry.

Melinda Wittstock:

100%.

Deborah Sass:

I’d love to actually ask the, the group a question because numbers don’t lie, you know, with the $400 million plus. And of course, they say that 28% of that money went to female, not female only, but female in the founding team, right? Whereas only 1% went to female, all female ML teams. But how do we actually— we, we all have a— we all have social capital here. We all have massive organizations that look to us. We advise. We have community. How do we actually change the narrative? Because we can all tell horror stories, but now let’s look 10 years forward. How, how do we make a difference? Like, how do we really truly make a difference?

Melinda Wittstock:

Well, Deborah, your question comes at the exact the right time because here’s where I was going to pivot the conversation to, like, the next 10 years and what has to happen. So, like, we’ve touched on some of the structural problems here, both within us and just how we’re socialized and the mindset, but also just the structural issue of the history and the tendency of VCs to invest based on pattern recognition. In other words, a guy, a white guy in a hoodie who’s dropped out of Stanford, MIT, Harvard, right? That’s their, that’s their thesis pretty much, right? So, there’s a couple things here, and I want to ask everybody about this, because when you actually look at the statistics, women do— women are a better investment. And like, I really mean this, and I’m just going to read this right now: delivering on average 2.5 times better returns than male-founded startups, women companies generate $0.78 of revenue per dollar invested compared to men down at around like 30 cents, right? We are more likely to get to— yeah, male founders, 31 cents per dollar invested. Female founders, more operational efficiency. We burn 15% less capital consistently. Our median burn rate tends to be lower for better results. We have 10% higher cumulative revenue over 5-year periods.

Melinda Wittstock:

Exit timing, 6 months faster to exit on average. Exit success rate, 24.3% of total US VC exit count, right? A record high compared to— I mean, that’s 2% of the venture company, but 24.3% of the exits. Hello. These are sobering numbers. So, for all these VCs out there who are like, want a return on their investment, why are they ignoring those stats? Because they’re just there, they’re real. Like, how to get them to understand that? Is there something that we’re missing? I mean, Rajia, it was really interesting about what you were saying about changing the narrative of how you were getting the investors to empathize or understand, right? So, when you’re looking at these hard, cold numbers that really are in our favor, how does that pitch go? And not only for the female startup, but also for the female VC fund trying to raise from LPs.

[PROMO CREDIT]

Wings of Inspired Business is brought to you by the podcast, Zero Limits Business Growth Secrets where Steve Little – serial entrepreneur, investor and mergers & acquisitions maestro – shares the little-known 24 value drivers that spell the difference between a $5m business, and a $50mm even $500 mm business. It always pays to understand what’s driving the underlying enterprise value of your business. So, check out Zero Limits Business Growth Secrets at zerolimitsradio.com – that’s zerolimitsradio.com and available wherever you get your podcasts. More information about valuation growth at Zero Limits Ventures.com

Melinda Wittstock:

And we’re back with Trixy, Ungenita, Clare, Deborah, Lindsey and Rajia.

[PANEL CONTINUES]

Rajia Abdelaziz:

I think I think one of the biggest problems is the connections. A lot of the venture capital world comes from a warm introduction. You just read some incredible statistics surrounding the amazing results that female founders are able to achieve, and it’s because they’re working really hard and they’re very resourceful. Not all of them are out going to networking events or golfing with the right people that are going to introduce them to the venture capital.

Melinda Wittstock:

Yeah, I’m on this.

Ungenita Prevost:

Are you in too?

Melinda Wittstock:

Right.

Rajia Abdelaziz:

I think part of the biggest piece that we need to solve is how do we connect venture capitalists to the right women entrepreneurs? I was actually just having this conversation with one of our investors. He was part of a big fund in San Francisco, and we were talking about the statistics, and he was telling me from his point of view, one of the biggest problems is he’s not getting access to these female founders.

Trixy Castro:

Interesting.

Rajia Abdelaziz:

Where are they?

Melinda Wittstock:

Where are they? Oh my God, my head’s exploding.

Rajia Abdelaziz:

I’m not even kidding you. It’s because a lot of us are not on the golf course. And all the female founders message me after, I’ll connect you to him. But essentially what he was saying is, in his opinion, they’re seeing like 10 times as many companies that are led by men. And part of it is when we were raising funding, for example, Melinda, It was a lot of the connections I had personally did not have connections to all the VCs where a lot of the male founders that I’m friends with are like, oh, well, I met this guy at this guy because he’s friends with this person who’s friends with that person. So, I think we really need to focus on helping facilitate the right connections and also providing the mentorship. One thing is even if a person does not personally understand the problem, If your company has so much traction, if you were on Good Morning America and you sold a quarter of a million dollars in 2 minutes, it doesn’t matter if your wife doesn’t worry about her safety. That is showing you this is a market that is massive that needs to be invested in.

Rajia Abdelaziz:

I think it really comes down to also teaching women entrepreneurs a lot of the resources that a lot of us have learned the hard way, joining founders communities and so on. I wish someone had introduced me to more founder communities when I was younger. I think I could have skipped the first 3 years of mistakes that I made in my little office with my 5 team members. But I really am optimistic about the future. I’ve been a part of a lot of incredible female-founded communities, and it seems like every single entrepreneur, every single female entrepreneur shares this passion of changing the narrative. And you give us 3 to 5 years, when we exit, we’re all going to become LPs and we’re going to mentor the young entrepreneurs. That’s what has to happen.

Melinda Wittstock:

That’s absolutely right. You’re on point. That’s what has to happen as we exit. And I mean, here’s another interesting stat. It’s something like women are expected to control roughly $30 trillion, $30 to $34 trillion in financial assets in the United States by 2030.

Deborah Sass:

Okay.

Melinda Wittstock:

It’s 4 years, less than 4 years away. And this is this big generational wealth transfer. That is enough capital to change the game because when we invest in startups, we’re really picking the future. So, what kind of future do we want? What kind of country do we want to live in? What kind of world do we want to live in? There are all these big pernicious problems that need to be changed. Climate, food, there’s so many different things. And women tend to create in my experience anyway, from what I’ve seen, really mission-driven companies that really do want to change the game, they usually, usually have some sort of social impact dynamic to them, more likely than, than, than a lot of men. So how do we get women, and not just entrepreneurs, but women of wealth, to really get educated and savvy about investing, not just in philanthropy, But female startups, female funds, what does it take? Because my sense is we have this kind of Balkanized system in a way, right? Like, you have all these different— a flourishing of female VCs, but they’re all very small. So, they can’t really compete in the same way that the big— the a16zs and Sequoias and whatnot, right? So, how can we bring a lot of this, pool some of this money together? How can we connect the right people to the right opportunities? How can we be more abundance-minded in, like, pooling together, like, sharing opportunities? And how can we— I think a lot of it maybe is education as well.

Lindsey Mignano:

Mm-hmm.

Melinda Wittstock:

So, Clare, I’d like you to kind of start in on this because I know this is close to your heart as well. and Trixy, you too. Ungenita, we’ve talked about this, like, ad nauseam. Like, what does it take? 

Clare Baukman:

When I was in LA, um, I had a producer approach me and wanted me to do some kind of like stock talk thing in the morning? And I’m like, no, no, I’m, I’m not doing that. But he and I actually created something called Found Her, the show called Found Her. It was for female founders, and this was exactly it. So, what I found from a little bit more on the helping guide people how to invest in alternatives, in art, in VC, is a lot of the women who are on the VC who are trying to do the cap raise, and then a lot of the women who are investing, the education and the awareness is not there.

Clare Baukman:

And a lot of times, as you know, the male in the household will take over. And I’m finding now more and more that women will start to take over. And I actually have a lot of boss ladies who I look after as well, and they are making the decisions, and the husband has no idea. And that’s great. I think it should be an equal. We’re an equal in our house. So, um, but one of the things I found with the— these, these wonderful businesses who wanted to come and pitch on the— it was kind of going to be like a Shark Tank or Dragon’s Den kind of thing, but just a little bit different. Not your average pitch show.

Clare Baukman:

We didn’t end up going forward. But one of the things was all of these women, they had no idea how to pitch. What— like, they had this great business. And see, those of you who, like Rajia and I think Trixy, you guys went and you raised the capital. I can’t remember who else said they have. You maybe intrinsically just had it in you, and you were like, I’m going. But a lot of these women don’t, and they have these wonderful ideas.

Clare Baukman:

They just have no idea where to put them. So, if there’s some kind of— see, there’s all these angel platforms, and a lot of them are garbage, and they’re not really doing anything right. And then on the VC side, uh, a few of you said this, that the education is just— it’s not there. And if it’s not speaking in terms of their interests and it’s not applying to their fear or their greed, they’re like, nope, don’t care, don’t understand it, next, right? I think, Rajia, it was you who said you changed the way you explained it and then bam, they were starting to write checks, right? So, I really feel deeply that it’s an education and an awareness And I always think more eyeballs on you is always better, and we have it in the palm of our hands right now, right?

Lindsey Mignano:

Yeah.

Deborah Sass:

Yeah.

Rajia Abdelaziz:

I’m so glad you said that, Clare, because one of the things I didn’t say is really there’s an unspoken playbook on how to raise venture capital properly and how you communicate to investors and how you present yourself. is honestly half the picture. Like you mentioned, with just changing the story, changing the wording. We had a really incredible advisor. Her name is Christina Apple. She actually was a venture partner at 776 Ventures, Alexis Ohanian’s fund, who gave me a lot of incredible mentoring and coaching on how to approach all of these conversations and leading from a position of power. I think a lot of times too, People feel so desperate to get the capital. And for me, I was, I was like, I want the right person.

Rajia Abdelaziz:

I’m going to be as selective about you as you are about me, because I’m going to end up making you millions of dollars. And that’s going to change your life and your fund as well. So, I want to make sure that you’re a good person and your mission and your morals are aligned. It’s not just you looking at, hey, do I want to invest in her company? I’m like, do I want to do business with you? Do I want to make your fund a lot of money? And that changes the power dynamic that we were talking about earlier. You can’t be looking at these people as, oh, they’re the most incredible thing. Like Melinda mentioned, a lot of investors are actually, they’ve never ran a successful company, which nothing wrong with that by any means.

Melinda Wittstock:

But it’s hard for them to evaluate.

Trixy Castro:

Like they, they—

Rajia Abdelaziz:

Exactly. You have to keep that in mind. After we had raised millions and one of the investors He said to me, you know what, flat out, I’m not even joking with you guys. He said: this is a really incredible company and what you’ve— the amount you’ve raised so far is amazing, but respectfully, you’re only 21 years old. And for that reason, I am going to pass on this investment because I don’t think you’re qualified to be the CEO of the company. He said that flat to me, no sugarcoating anything. I called one of our investors, Michelle, who started one of the fastest growing cosmetic companies in the country. I said, can you believe he said that? She said, Rajia, why didn’t you tell him, hey, by the way, I’m curious, did you raise millions of dollars by the time you were 22 years old? Clearly not.

Rajia Abdelaziz:

So, I don’t think you’re qualified for me to even consider taking your money. Second of all, with all due respect, that tells me you would not have invested in Mark Zuckerberg’s company.

Ungenita Prevost:

100%.

Rajia Abdelaziz:

Or Bill Gates’ company. So, it sounds like your fund is going downhill, buddy.

Melinda Wittstock:

Yeah.

Rajia Abdelaziz:

And I remember being shocked by Michelle’s reaction, but she is so correct. It really like was exactly what you were saying, Melinda, of there’s no reason for there to be a power dynamic. It needs to be a partnership, and you need to be equally as excited. So, you need to be like, if you’re a woman listening to this podcast, you need to be coming at it from you’re not desperate for the money. Look at it from an abundance mindset. That the first 99 guys say no, that’s okay. Keep going. Do not give up.

Rajia Abdelaziz:

Find the right mentors. Go reach out to Christina. Reach out to any of the incredible women on the call. We’ll all gladly share some advice and help you get there.

Clare Baukman:

You’re absolutely right. Don’t put them on a pedestal. And that is huge for your mindset going into this, right? Because they probably don’t understand the business anyway. And something I’ve said quite a bit in my career is that’s okay. It’s not for everyone. And the second I say that they’re like, well, why? What do you mean it’s not for me?

Lindsey Mignano:

What if it is?

Clare Baukman:

And they start changing.

Clare Baukman:

We’re done.

Deborah Sass:

Yeah.

Melinda Wittstock:

I found that that really works. This is weird reverse psychology. People like to be empowered to say no. I learned this in like enterprise tech sales. I’d ask a question in the sale. So, can you see any reason why you wouldn’t want to do this? And they would say no, which was awesome. That was good for me because they got the dopamine hit of saying no and feeling in control. But meanwhile, they sort of said yes, right? And like, just little things like that that are kind of very simple but very—

Trixy Castro:

That’s so true. I have to just interject on this one because, I mean, look, I told you guys how I started in business. And then to go on and raise billions of dollars and deploy them successfully, right? And have 2 exits of 2 massive companies within 6 months of each other. Not like mom-and-pop kettle, Fidelity National Title and Goldman Sachs. So, 2 heavy hitters, right?

Ungenita Prevost:

Yeah.

Trixy Castro:

Where I was told a million times, and we can go through it, you don’t belong here. Who are you? All the things, right? I learned to train myself to use that as fuel and energy. But this is such a big problem that I see in women’s businesses in general. It’s everything we’ve been talking about— access, exposure, knowing how to present yourself. A man walks in the room, right or wrong, and they’re going to beat their chest and tell you about all the deals they’ve done, how great they are, and every idea was theirs, okay? Every single idea. We are like taught to like, oh no, I’m going to give someone else the credit, I’m going to give someone else the credit. And when you’re raising money, you can’t. You have to be able to articulate your business.

Trixy Castro:

But let me tell you something, and my view is probably very unpopular. It’s one thing to manage people’s money, okay? You have to be really good at choosing the winners, okay? Put me on a call with you ladies. I already know everyone here is a winner. Job done. Very different than starting something from nothing, okay? So, there was one time where I was told, oh, Oh, can you get me the water? Sure, I’ll get you the water, the tea, the coffee, whatever. This was a real meeting, right? But I’m your meeting. Impossible. You’re not the meeting.

Trixy Castro:

So, one of my employees that worked for me, a man, he kept looking at him. He had to redirect this person 8 times to talk to me. And I’m like, okay, no problem. But that goes to show you that’s a ‘them’ issue.

Rajia Abdelaziz:

Yeah. Didn’t matter.

Trixy Castro:

That’s a ‘them’ issue. That’s the way they’ve been conditioned to think about the world. there’s a million of them, one of me. So, to Rajia’s point and to all of your points earlier, you built something out of nothing and you’re building it and making it great. That’s yours to protect. So, when you’re taking someone’s money, it’s the same thing as if you just have to minimize the big scary out of it, right? Because it’s, are they going to be the right partner to scale me? But you have to know your vision. So, if I want to exit or I want to do this, are they aligned with that or are they going to rip it apart and make it something else?

Trixy Castro:

And that’s a decision that only you can make. They can’t make it for you. But it’s such a big issue that even inside, which is why I built Success Unlocked to create access exposure. I have a full-time woman who is amazing just teaching people how to make their pitch, how to be able to make it on Zoom, make it in person, make it in an elevator. Because to our point earlier, a lot of us, I never got the golf invitations. I never got the like, okay, we’re going to the cigar club invitation. I got that. Wait, aren’t you Cuban, Trixy? Can’t you roll me a cigar?

Ungenita Prevost:

Sure.

Trixy Castro:

I mean, right? And so, as a matter of fact, I can.

Rajia Abdelaziz:

Don’t want to, but you know what I mean?

Trixy Castro:

So, it was just one of these things. We already know it’s, it’s not equal all the time, but what we can do is take our power back and reframe it, because the truth of the matter is you’re— we’re the ones building it.

Melinda Wittstock:

Uh-huh.

Lindsey Mignano:

Along with I was just going to add, you know, along the lines of taking power back, you know, it’s— I do think that at least in Silicon Valley, there’s an emphasis towards pushing people towards venture capital. Culturally, it’s very the norm.

Clare Baukman:

It’s a badge of honor.

Rajia Abdelaziz:

Yeah.

Lindsey Mignano:

But I think the way that you can take your power back is understanding how to finance and build a business without venture capital. And I think more women are looking into that in light of the statistics. I think it’s great. I don’t think that we as corporate lawyers or venture lawyers talk about it enough. But, you know, we’ve had a number of clients go through successful crowdfunding campaigns, SBA loans, non-dilutive lines of credit. There’s a company out of Seattle that does revenue-based financing, Lighter Capital, for companies that are software companies. There’s a lot of other ways to do this type of work that are not venture capital. And I think part of reclaiming your power while still having money to build your business, because at the end of the day, you have to have the cash, is really understanding the alternative lines of capital that are non-dilutive, right?

Melinda Wittstock:

100%.

Lindsey Mignano:

Because venture capital and venture debt are very expensive types of capital. And I actually love the VCs who will tell you, I may not be the right fit for your business, because maybe you’re not the kind of company that’s going to IPO. And I need to have a certain number of companies in my portfolio that IPO because I got to give my LPs the 3 to 5 5x that I told them I would, right? But if you’re not that kind of company, that’s no shade on you. You might be an incredibly great small business, incredibly lucrative, incredibly high profit, but maybe it’s not right for VC. And we don’t have that conversation enough in Silicon Valley.

Melinda Wittstock:

And by the way, you might want to hang on to control of your company.

Ungenita Prevost:

Yeah.

Melinda Wittstock:

I mean, you know, a bigger— keep or retain a bigger share of your company. Because I think sometimes founders don’t understand that with each VC investment, they’re selling They’re depending on— and Lindsey, I know you help people with this, but this, you know, the term sheet can be a founder’s enemy, especially if you’re raising and you’re desperate and you need that money and you, you kind of get married to the wrong, you know, the wrong dudes, right? Usually dudes.

Trixy Castro:

Good analogy.

Melinda Wittstock:

Right?

Lindsey Mignano:

We see founders get haircuts of like 20% at seed, maybe 16%, 17% at A, maybe 16% at B, right? At each round you go, It’s not free money. But even more so, even outside from the dilution at the founder common stock level, when we see our startups get in disputes with their investors, a lot of it is like relationship oriented.

Rajia Abdelaziz:

Yeah.

Ungenita Prevost:

Right.

Lindsey Mignano:

It’s still like a marriage, right?

Rajia Abdelaziz:

It’s the people part.

Lindsey Mignano:

It’s the, he doesn’t really support the direction I want to go in. And he’s on my board. And I thought he was, he had my back. And we’ve been like, guy, opposite ends of the table. This is an address to a real party. It’s all collaborative until it’s not, right? So, understanding what rights you’re giving away at each round, with each side letter, if you’re a SAFE note round, or if you’re, you know, in your term sheet, if you’re a venture-priced round, is really important. And it’s hard for us as lawyers when we’re in the room talking with a startup client because startup client just met the VC. They think they’re gonna be best friends forever, forever and ever and ever.

Lindsey Mignano:

We’re gonna go and like, our kids are gonna get married one day. We love each other. And then And then 3 years later, you don’t love each other. And yeah, it’s the worst thing for me to be like, told you.

Clare Baukman:

Right.

Lindsey Mignano:

But it happens. And so, we’re trying to be as protective as possible in a scenario where we’re planning for the worst, but the environment at the marriage seems very collegial and collaborative and great. But fast forward, and we’ve all been in this business for a number of years at my firm. Like, most of us have over 10 years, 15 years of practice. Like, we’ve seen how things give it a bit. when things go south, how people show their real colors, and maybe then the relationship is not so good. So, it is a long-term marriage, and I really commend the VCs whose founders really love them. We try to find those VCs that our founders love and put our other founders with them because we want people who work well and play nice in the sandbox.

Melinda Wittstock:

That’s great. And I mean, that’s the kind of diligence that every founder should be doing. Like, Raj, I think you were mentioning this too. You’ve got to qualify the investor as much as the investor is qualifying you. And one of the best ways to do that also in the warm introductions is figure out who’s been funded.

Ungenita Prevost:

Mm-hmm.

Melinda Wittstock:

Like, because, you know, who’s been funded and what’s their relationship? If you can get founders to talk, you know, it has to be off the record or whatever, but as much as you can, as much as you can do that, that’s really critical. So, as we wrap up, I have a question. I have a couple more questions for you. One of them is a particular— when I look at women like Mackenzie Scott and Melinda Gates, who have tremendous amount of money and they’re doing great things in philanthropy, but I have yet to read about them investing in any startup, and particularly any women-founded startup that may well be and is likely to be addressing a lot of the same issues perhaps as a charity. What is it going to take to persuade women like that to actually blaze a trail? Do we need some sort of trailblazer first of all, or is this change getting women to invest in other women just going to be— just go at a very slow pace, or do we need to persuade Melinda and Mackenzie to, you know, get on with that and how do we do it?

Lindsey Mignano:

And for all we know, maybe they have family offices under different names where we don’t know if they are investing privately, right? A lot of wealthy families have family enterprises, family offices that invest in companies on the side and very quietly. And they also invest in other funds, right? So, there are family offices owned by wealthy women where you may never hear, like, their name.

Melinda Wittstock:

Right. That’s encouraging.

Rajia Abdelaziz:

I’ll believe you.

Lindsey Mignano:

I’m not saying those particular women, but I do want to point out, because we do represent a number of family offices, that it’s not necessarily that they put the family’s name on it for privacy reasons, right? They don’t want to get hit up for an investment every time their kid’s friend comes home from college and is starting a startup. So, there is some anonymity there, and that’s purposeful.

Melinda Wittstock:

Yeah, okay.

Deborah Sass:

I, I’ve got a solution that we all, every one of us, need to be that change. And maybe we need to start an alternative funding for— I mean, women are not minorities. It’s just so fascinating. I know, we’re 52% of the population. But maybe there’s a way that women like us with that Type A overachiever personality can actually talk about how we really truly do something. What is the takeaway? I mean, all these horror stories are interesting to an audience member who’s had those same experiences, but what do they need to hear? They need to know how they get the money. Do they talk to VCs? Is it about what you call pattern recognition, right? Is it about the same people who went to the same school and I mean, there’s a big world out there.

Melinda Wittstock:

Yeah, we gotta break that pattern. Those patterns aren’t really serving us because if it’s always based on what came before, well, we know what came before, right? I think the answer is somewhere in abundance. I like the idea of women, like women who are running VCs, women who are running angel networks, women who have podcasts such as this one, or women who are mentoring, you know, of all somehow pooling together rather than compete. Because there’s a sort of a competition, or there’s sort of like a little bit of scarcity, like I’m doing my thing over here and you’re doing your thing over there. But until we get sort of the scale — to pool resources somehow, and that’s a lot, that’s looking like a herding cats task maybe, I don’t know. But I’d like to see that happen.

Deborah Sass:

I mean, sign me up. Sign me up, Melinda.

Rajia Abdelaziz:

I’m in.

Ungenita Prevost:

Actually, brings up the fun. I mean, this is what we talked about.

Melinda Wittstock:

Exactly.

Ungenita Prevost:

Because I thought, okay, I could raise money and then we would bring on other women who wanted to raise money and have this fund.

Melinda Wittstock:

Yeah.

Ungenita Prevost:

And everyone would get funded. And the interesting part is fund, or investment funds now are very chic. You hear about Jennifer Lopez; you hear about Serena Williams.

Rajia Abdelaziz:

Yeah.

Ungenita Prevost:

Well, obviously they have, you know, 9 figures, right? I’m not saying they can— it’s their funds, but perhaps they were able to bring in investors to put that 9 figures into the fund. But that’s what we originally talked about. was to start a fund. So, I would love, you know, to hear from you ladies about that aspect, because would that be a way for us who are in at a stage where we are, are raising capital to bring women together who are also raising capital, but they’re— they aren’t at an exit level?

Rajia Abdelaziz:

Yeah.

Ungenita Prevost:

Any, any takers?

Rajia Abdelaziz:

Yeah, I’m curious, Melinda. I guess starting a fund is not easy.

Melinda Wittstock:

Starting a fund is not easy, especially if you have no fund management experience. 

Lindsey Mignano:

I started a fund with no management experience.

Melinda Wittstock:

I’m all ears. Go, go.

Lindsey Mignano:

Very easy to do. I have some legal experience, but I started a fund of funds that invested in Turing Capital, which is like a $300-something million fund that deploys enterprise AI. I gathered 30 of my accredited investor girlfriends, and we all put our money together in this fund of funds, right? We did a similar thing for a real estate syndicate, which has like 7 or 8 different self-storage and self-wine storage facilities. Like, I don’t know if that was the best investment, but we’re waiting it out. It is actually quite easy to do it. I’m not saying this because I’m a lawyer. I’m saying because there’s so many online options out there. We used Carta, for what it’s worth.

Lindsey Mignano:

Carta has a fund formation option. It requires 506 accreditation, which means, you know, there are numbers that you have to hit as an individual or a couple in order to be considered an accredited investor for both the real estate syndicate fund-to-fund and the venture fund-to-fund. You can also, like, you know, then invest directly in startups. We don’t. We prefer to put our money in other funds and have it then diversified over a course of different startups and different real estate properties. That hedges the bet. It means that we’re not all invested in this one thing, right? But that is more and more accessible than ever. You can form it on AngelList.

Lindsey Mignano:

You can form it on Carta. You don’t have to be a fund manager, especially like for me, it’s a love of the game. I never took any management fees or carry. So, there’s no registration issues. 

Melinda Wittstock:

Yeah. So, that’s the difference. So, you were pooling people that were already kind of high net worth, like, as you mentioned, your girlfriends, right? You get a whole bunch of people together and say, okay, we’re gonna put our money here, as opposed to a traditional VC fund, like, with all the money and the, you know, the VC fund.

Lindsey Mignano:

We were able to get in because I’m friends with the female GP on their family and friends vehicle, which was a very kind thing, because also then I don’t have to pay her management fees.

Rajia Abdelaziz:

Right.

Lindsey Mignano:

This becomes a girlfriend thing. But that was a very lucky, lucky thing for us to get involved in. Most VCs who are micro-VCs who approach us will absolutely take the 2 and 20 from us. Thank you very much. And then it becomes a matter of whether or not the amount that we pay in expenses for the fund administration, the taxes, all the relevant things, even if I’m comping legal, and no one’s really doing a management fee or carry on my end, makes sense in light of the 3 to 5x return that we’re hoping to get. And I’m gonna put this in quotes, because I do think that while venture investment is great, and we always have seen sometimes really banger funds where they’re like 10x, for every one of those, there’s a 2x fund, which in that case, you have to wonder whether your money’s better sitting in the market, right, in some ways, and it being immediately liquid. So, I do it in a variety of different ways. I’ve also invested in blue blue-chip art.

Lindsey Mignano:

That’s something that I probably don’t have enough education to, but I have done it. You can invest in funds for blue-chip art. Masterworks does it. Clare’s company does it. So, I think there are ways to get your money out there and to pool money with your friends, provided you’re not taking any fees or anything that require any kind of registration. But it is not inaccessible anymore. These are online options. They’re made for emerging managers.

Lindsey Mignano:

And there are tons of emerging managers that we meet every day who are doing women-owned venture funds, and they’re first-time managers. They maybe they were in tech, or they were a founder before, and maybe it’s like a small, like $50 to $70 million fund, but they’re doing it online, and they’re doing it themselves.

Trixy Castro:

I agree with you. I’ve done so many funds as well, and if you guys want to do this, I am in. I will help manage it. We have, we have a Reg A fund right now, which is like, okay, no accreditation. Anyone with $100 or more truly can go in and invest in real estate. SEC gold star, all the things. People have made no less than 12% annualized, honest to God.

Ungenita Prevost:

Wow.

Trixy Castro:

We have 30,000+ investors on that platform. So that’s already in existence today to get the cash flows up. But if you guys want to do this, there’s a million different ways. Lindsey, I’m sure, can guide us. I will totally volunteer to do this because investing in women, you to your point earlier, Deborah and Melinda and all of us, that’s how we change it. I really believe that Deborah’s challenge of us getting together is a reason, Melinda, that you brought us all together, is a reason that we all hear a business or hear about it and we’re like, oh, I want to fix it, I know how to do that, here, let me help you.

Melinda Wittstock:

Exactly.

Trixy Castro:

We can’t turn that off, right? Like, I think all of us like are like, I wish I could, but I can’t. So, if you guys want to do it, I’m in.

Melinda Wittstock:

Because I’m thinking about like the next 10 years. I started this podcast, I’d exited a business, and I was like, what am I gonna do? And I was like; this has been a hard journey. I want to kind of give back. Like, when I started as an entrepreneur, I didn’t even know what the word entrepreneur meant. I was the only woman in the room, you know, all the things, right? I started because I think this is the show that I wish I’d had.

Ungenita Prevost:

Yeah.

Melinda Wittstock:

Because I didn’t have the relationships, I didn’t have the resources. It’s so much easier now. I set out with this intention that I really want to drive a minimum of $10 million to female-founded startups. And I had this idea in my mind that that would be like investment, right? Like I’d exit my next and I, you know, but it turns out that conservatively this podcast has driven more than $10 million of revenue to the women who’ve been on the show.

Trixy Castro:

Wow.

Melinda Wittstock:

Right? Which is really cool. And so now I think, okay, well, I’ll keep going with that. But now I want to put it on a different— like, what’s the next 10 years?

Rajia Abdelaziz:

Yeah.

Melinda Wittstock:

Because this has always been a mission so close to my heart. I’ll tell you a story about my Aunt Bea. So, Aunt Bea was Canada’s first female stockbroker. There she is in Toronto. She gets going in her late 40s. She can’t get any clients. So, she figures out she’s got to make her own market.

Clare Baukman:

Absolutely.

Melinda Wittstock:

She decides she’s going to go out and talk to all the women who are divorced and women who are widowed or whatever. And she becomes the biggest producer of her firm, like, in the 1970s and ’80s. And she works until she’s 86, until they bust her for her age. Like, she was supposed to retire at 65, but she just, like, lied about her age. It’s like, back in the day, you could, like, change your age on your driver’s license. I don’t know how she did it. I was like, really? She was like a badass. And so— and I remember watching her as a kid thinking, wow, okay.

Melinda Wittstock:

I like her example of just going out and doing it. So, how can we— there’s a number of different things here. So, there’s the education, there’s like the pooling of resources, education not only as like, what does it take to invest or why should you invest in either startups or whatever, how to become a good investor, how to become discerning, how to find opportunities, all that kind of stuff, how to be less fearful about investing, and how women can get better at pitching. All of this is of peace, right? And maybe you’re right, this conversation is, okay, so what’s the next step? How can we get together? What kind of groundwork can we lay? And I just sort of say, I’m all in. I feel at this stage of my career, the best and most wonderful thing is helping to be a sun that lights other suns, that can light other suns. I mean, like suns, like as in that solar system, right? Um, so that we can really spark that. So, this is the first conversation. 

Melinda Wittstock:

So, what’s the first thing we should do? And anyone listening to this who wants to be part of this group.

Ungenita Prevost:

I’d love to have an event. We can do this online, a networking event where we bring female founders, female investors together, you know, and, and have those conversations, do breakout rooms where people share their generosity in terms of their information. They’re also open to make introductions. I mean, obviously that’s what I used to do, so that’s easy for me, but I also know it’s effective. And I just want to say this regarding the introductions, because this is something I used to teach women, is how to do the million-dollar introduction. Because women would come to me, they’d come into my community, and they did not have the introduction. And so, part of what I used to do was I used to give women the mic and help them get comfortable making the introduction, making the pitch so that it didn’t matter. I was on a Zoom, I’ll never forget.

Ungenita Prevost:

And I ended up meeting this guy, a VC in, in Palo Alto. And it was literally on a Zoom, 5 minutes. I connected with this guy. The next thing you know, I introduced him to another female founder. But it was because, again, I have those skills and I know how to connect with people. And I think that that’s the core piece because once you meet the person, you really, you don’t get a lot of time, and you have to really utilize that time. So that’s my, you know, sort of idea is to have an event. We can do it online and bring women together, investors, and especially women who’ve raised hundreds and hundreds of millions of dollars.

Ungenita Prevost:

Um, to show, you know, how they did it.

Melinda Wittstock:

Well, look, I’m up for anything. I think it’s a great idea. I love the idea of really being of service, of any way that you can show up. Entrepreneurship, ultimately, it’s who you’re being, not just what you’re doing. It’s like, like who you are and the energy that you bring. And, and are you uplifting people? Are you in abundance? Or are you in scarcity? Are you coming from a place of love or are you coming from a place of fear? And so much of it on that kind of energetic level. Like, I think there’s so many different sort of levels or planes to this, but I would like to us be sitting here 10 years from now saying, oh my God, like, do you remember that conversation we had in the fall of 2026?

Clare Baukman:

Yeah.

Melinda Wittstock:

We were getting less than 2% and like, look at us now. I would just set that intention.

Deborah Sass:

I love that. I would like to go and ask every single venture capital fund person that just in my tiny little network, if we look at every single person on this call and if we talked and got a million bucks from every single VC, family office, PE, whatever it was, we would have the biggest fund in the world. That’s how you change it. That’s how you change it. That’s how you change the narrative. And by the way, if I can ask 300 people, which I’ve done raising money many times, and 299 said no, this is a real game changer that every venture capital fund wants to be part of because this is about changing the narrative.

Melinda Wittstock:

100%.

Ungenita Prevost:

Wow.

Melinda Wittstock:

Okay, so 10 years from now, any— anyone willing to make, as we wrap willing to make kind of a prediction or maybe set an intention for where we’ll be 10 years from now?

Clare Baukman:

I feel like this is “BlackRock meets Chanel”.

Trixy Castro:

I mean—

Melinda Wittstock:

Oh, I love that.

Clare Baukman:

It’s like, it’s just, I love it. It’s there.

Melinda Wittstock:

Oh yeah, that’s fantastic.

Clare Baukman:

You heard it here, folks.

Melinda Wittstock:

Okay, that might be, that might be the title of the podcast. Maybe we’ll have to incorporate that one into the show notes.

Rajia Abdelaziz:

I love it. I think, Melinda, the narrative will be completely different. I hope that this is a story I share with my kids, that back in the day it was 2% and now it’s an equal amount. And all of these super successful women entrepreneurs band together to become limited partners or to start new funds. I really hope that my future children have no idea and they’re like, what do you mean you lived in a world where 2% of venture capital went to women? But that’s what’s going to happen. I also want to stress too, for anyone listening to this, I can’t remember who mentioned it. I think it was Lindsey that we tend to give entrepreneurs this big gold star that they raised funding. And really we need to be giving the gold star on profitability and revenue.

Rajia Abdelaziz:

That’s where we need to be giving people the gold star. It’s not about how much funding you raise. It’s how creative are you to get your company to the next level to be that massive success? Any young woman entrepreneur listening to this, go research a company called Comfort Clothing. The founder  was in his early 20s. Within 4 years, he bootstrapped it to a billion dollars by learning how to do affiliates and TikTok Shop. If he could do that, every single young woman entrepreneur can see similar traction. And she invests the same amount of time researching all of these strategies. So, I just encourage everyone listening to this conversation to also look for alternate ways of capital, not just focus on the VC landscape. But we will, we will, will definitely change those horrible statistics and make it equal.

Rajia Abdelaziz:

That is my goal, Melinda. In any way I can support you and the other women on the call, more than happy to.

Melinda Wittstock:

And, and likewise. I want to take a moment and just because I’ve taken so much of your time, we could talk for hours more. But my profound thanks to all of you, like not only for your initial interviews on Wings, but just the privilege of knowing you and just all the amazing things that you’re doing in the world. I just feel so grateful that you took the time to celebrate 1,000 episodes with me. So, thank you so much. Thank you.

Rajia Abdelaziz:

Thank you so much for having us and for this wonderful conversation.

[PANEL DISCUSSION ENDS]

Melinda Wittstock:

So, watch this space because together with these unstoppable female founders and investors, we’re going to change the game in the next decade. Thanks to invisaWear founder Rajia Abdelaziz, Ungenita Beauty founder Ungenita Prevost, SpaceVrse’s unstoppable Deborah Sass, Silicon Valley legal maven Lindsey Mignano, Wealth architect Clare Baukham, and TRX Capital’s Trixy Castro.

Melinda Wittstock:

Now, as promised we’re going to end the episode with venture investor Naseem Sayani.

[INTERVIEW B STARTS]

Melinda Wittstock:

Yeah. So, let’s get back to, like, what needs to be done. We’ve got this massive wealth transfer to women. Yeah. We have this lack of education. So, what’s this community of getting together, comparing notes? I’ve talked to female investors who say, look, I’m, I’m trying to find opportunities.

Melinda Wittstock:

I don’t know where to find them. And then obviously the startups are trying to find investors. So, there’s like a big disconnect there. Resources, education. Yeah. What has to happen to get more women investing? Because I know this is a big mission or something I share. What are all the things that have to happen to get them writing bigger checks?

Naseem Sayani:

So financial fluency is a big one. It’s just a, you know, getting involved in understanding the terms, the language, the opportunities because a lot of women really only think about checking accounts and savings accounts.

Naseem Sayani:

And, and that’s not wealth building. We’re not building generational wealth on checking accounts and savings accounts.

Melinda Wittstock:

Understanding leverage. Understanding leverage. Right? Leverage is a big gap, I think. Yeah.

Naseem Sayani:

Understanding how to use debt to your advantage. We are all completely brainwashed into thinking debt is a bad thing.

Naseem Sayani:

Very wealthy men use their stock assets as the collateral to get huge loans, and they live their life using the money from the loans. And because it’s a loan, it’s not counted as income. So, they also don’t have any income taxes. Yeah. But their stock is sitting there just fine. Yeah. Right? And so, it’s just there’s a model by which men have accumulated wealth that just hasn’t been in how women are thinking about wealth building. And married women; the dynamic is even more complicated because a lot of times they’re deferring all of those decisions to their partners.

Naseem Sayani:

And so, one, I want women who are in partnered relationships where they want to have more of a voice in the financials and the wealth generation of their households. And Sally Krawcheck said this, I’m totally borrowing it. You have to move from being the treasurer to being a co-CFO.

Naseem Sayani:

You say, well, can I put $25k here? Oh, can I you know, what if we did this? Instead, what I’ve heard some women do, which I think is actually much more thoughtful and strategic, is when you’re making your financial plans for the next year, you say, you know what? I would love to have $150,000. That’s my allocation.

Naseem Sayani:

To decide where I want to invest it over the next twelve months. Right. In that way, you’ve already pulled your capital. And within that, it’s your decisions to make, but you’re not going back for the ask each time to that household bank.

Naseem Sayani:

Oh, yeah. Oh, absolutely. Because we’re not the muscle’s not built, right, to write a $250k check over a weekend. And so, starting small feels better, smarter, less risky. Right. And that for me is where, again, going back to community where volume can make a huge difference. And I’ve said in a few places that if women wanted to put billions of dollars into venture capital today, we could do it.

Melinda Wittstock:

We could do it. Like, look, seriously, if you had, like, a whole bunch of having done a whole bunch of innovations in the realm of crowdsourcing. Right?

Melinda Wittstock:

I mean, just if every woman put a couple thousand bucks into a fund and …

Naseem Sayani:

I was backing into some math, like, if you know, how many women were older than 35 years old in, you know, let’s say, 2024, it’s about a 100,000,000. Yeah. And if you take 1% of that and you assume they’re accredited, which is the SEC qualification to start investing 1% of that is a 100,000 women. A 100,000? Yeah. If they each put 50 k into venture, we’re talking about $55,000,000,000.

Naseem Sayani:

It’s a volume play.

Melinda Wittstock:

So that has to happen.

Naseem Sayani:

We can get we can get there. It’s like a stadium. It’s a sports stadium of people.

Naseem Sayani:

I want my shot at the big bucket. Right? Like, I don’t need the diversity sleeve. Just treat us like everybody else, and let’s do it because I promise you a lot of those first-time male fund managers don’t have any better track record than I do. But because of all the societal reasons like the pattern recognition; they get perceived differently.

Naseem Sayani:

But if we could otherwise, you know, the hundred thousand women doing the $50k each into some big fund of funds, and then we start to deploy the money out to the funds that are run by women. Or to your point, the consolidation question has come up a lot because we have a lot of Fund One’s that raised $580,000,000.

Naseem Sayani:

Like, let’s just put all that there. Everyone’s touching different parts of similar thesis areas. Let’s collapse it and get to one much bigger fund, and then I’ll raise the next fund together. Yeah. Because it’s right now, we’re walking in as exceptions into every room. Like, oh, the female fund manager’s here. If we all walked in together, we’re no longer an exception. 

Naseem Sayani:

And then let’s do that. Right? And let’s find a way to show up en masse, and then you can’t argue the proposition anymore. 

Melinda Wittstock:

Where do you think we can realistically be in ten years?

Naseem Sayani:

So, the wealth transfer is significant. It’s a combination of wealth going to younger generations, going to wives because their husbands died or coming from boomer parents, you know, to whatever levels of family. And so that leaning into that as a mobilizing mechanism for how we move more capital for me is very important. And the most interesting part of that is the younger generations because we’re despite the chaos and what we’re seeing is all the political strife, we are seeing these points of light emerge. Right? We saw what happened in New York. We saw what happened in Michigan with these different elections. It is the young people showing up and saying, I am done with this.

Naseem Sayani:

Also, they are they have a different mentality around impact. They have a different mentality around how they want to commit their time, and that’s gonna translate into how they want to commit their funding. I want more of these points of light voting behaviors show up in how money moves and how we’re preserving things around inclusion and preserving things around different populations and what they need and what their needs states are as far as economics and health care and lived experience.

Melinda Wittstock:

I think that’s a 100% true, and I’ve also seen it even with purchasing behavior. What just happened between Target and Costco last year. Target gets rid of DEI, they’re, you know, fall off a cliff. What’s happening with the ascent of MapQuest, right? 

Naseem Sayani:

What has been wrapped around DEI for so long has been it’s the nice thing to do. It’s the right thing to do. 

Naseem Sayani:

This is business performance, and we will not compromise business performance for the sake of some person’s mentality around these things, but this delivers outcomes. And if everybody started talking about it that way and said it’s this is I’m not investing in female founders Yeah. Because it’s not charity. We’re the churning more than every dollar. I’m here to make money. 

Naseem Sayani:

Do a lot of good at the same time, that’s what I want also. But I’m not here to not make money. Let’s not misunderstand. And I want that language to get into how we talk about these things that it’s not like, oh, I’m investing women, but you go, no. I’m investing in women because that’s actually how my portfolio is going to perform. Yeah. And I can’t just have dudes in the portfolio because diversity always pays off, and I’m leaning into that payoff.

Naseem Sayani:

And shouting the winds from the rooftops. Right? And just, like, amplifying each other every single day of the week.

Melinda Wittstock:

Amazing. Naseem, thank you so much for everything you’re doing in the world, and thank you for putting on your wings and flying with us celebrating episode 1,000.

[INTERVIEW B ENDS]

Melinda Wittstock:

Naseem Sayani is a venture investor and founder and CEO of GCWC and GCWC Capital, a media platform and investment fund focused on tech and AI-anchored innovations across HealthTech and FinTech. She also hosts the Capital Flex podcast.

Melinda Wittstock:

Thanks for listening to episode 1000 – longer than usual, but there was a lot to say! Please make sure you subscribe to the show so you never miss an episode – and tell your friends and colleagues. You can also help us get this wisdom out to more people by giving us a 5-star rating and sharing your reviews on Apple and Spotify—it helps more entrepreneurs like you find the secret sauce to support and grow their businesses.

Melinda Wittstock:

That’s it for today’s episode. Head on over to WingsPodcast.com – and subscribe to the show. When you subscribe, you’ll instantly get my special gift, the WINGS Success Formula. Women … Innovating … Networking … Growing …Scaling … IS the WINGS of Inspired Business Formula …for daily success in your business and life. Miss a Wings episode? We’ve got hundreds in the vault, all with actionable advice and epiphanies. Check them out at MelindaWittstock.com or wingspodcast.com. You can also catch me on LinkedIn or Instagram @MelindaAnneWittstock. We also love it when you share your feedback with a 5-star rating and review on Apple, Spotify or wherever else you listen, including Podopolo where you can interact with me and share your favorite clips.