BONUS - EP1: Women Have Learned How to Speak Men

For every two women who write a venture check, ninety-eight men do. That’s not a pipeline problem, it’s math, and it’s the pattern I’ve watched play out on repeat across two full seasons of The Capital Flex.

In this solo wrap-up, I step out from behind the interview chair to name what I’ve heard across dozens of founder conversations: underestimation, dressed up as due diligence. I revisit three stories that still sit with me and trace them back to the same root causes: network failures, semantics, and a system still built to treat women as the exception in the room.

I also share two stories I’ve never told on the podcast before: an LP check derailed by an investor’s husband on a Zoom call, and a client dinner where staying quiet made me, by way of stunned silence, part of the problem.

Key Takeaways:

• Why the quick no is worth more to a founder than a warm maybe, and why so few investors are willing to give it.
• How three stories from across two seasons all trace back to the same root cause.
• How a senior wealth manager’s husband was able to block her LP check,, and what it revealed about who actually holds the checkbook.
• Why staying composed and quietly stunned at a client dinner made me part of the problem instead of above it, and what I’d do differently now.

This Week’s Challenge:

1. Think of the last deal, hire, or relationship where you got a slow maybe instead of a fast no. What would you do differently next time?
2. Write down one moment you stayed quiet when something felt off. What caused that silence? What happens differently next time?
3. If you’re already making investments, ask the founders if anything has gotten weird and how they handled it; also ask the fund managers you have invested with, how they handle it internally when something surfaces.

Capital is not just money. It’s a long-term relationship. Choose wisely.

Links and Resources:
Listen to Somer’s episode

Listen to Annie’s episode

Listen to Dr. Somi’s episode

If you enjoyed this conversation, follow The Capital Flex, leave a rating, and share this episode with a founder who needs it.

And if you’re looking for a more candid space to talk fundraising, power, and building inside systems not designed for you, stay close. The conversation continues.

Production and Administration work completed by Smart Podcast Solutions and Elevate Business Solutions. 

Transcript

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SPEAKER_00 0:00

That's a wrap on season two of the Capital Flex. I'm Mistine Sani. 12 conversations in, a few themes became impossible to ignore. What founders are navigating, the strategies they're using to build resilient capital systems, and the early signals of how the innovation ecosystem itself is beginning to evolve. These recap episodes are a chance to step back, connect the dots, and ask what those patterns might tell us about where a venture goes next. Because as far as I'm concerned, when enough founders independently build the same workarounds, they're no longer just adapting to a system. They're revealing where that same system itself is ready to evolve. Stay closed, the conversations continue. I've heard so many stories from founders to date, both on the Capital Flex podcast and leading up to it. And there's two, maybe three stories that stick with me, kind of sit in my head, rent-free, as they say. And started to call out her ability as a leader, said that she was not, you know, properly following her fiduciary. And it just exemplifies such a combination of both of just bravado and a lack of awareness of what her other relationships might be. And I just imagine the opposite scenario. If her board hadn't supported her in that moment, what would have happened next? And that kind of behavior, it's such a clean example of that kind of behavior. It sits with me. The other one is uh Annie and her conversation and having to scrub the deck of anything related to diversity or LGBTQ or anything else that was actually core to her value proposition. And in order for that fund to talk about her company with their LPs, they asked her to scrub the language out of her deck so that it was more palatable. And I just it it makes me mad because you go, but this is the crux of what I'm building, is solving a significant problem. And the words I'm using to describe that, I actually have to take out of the deck so that your LPs are okay with it. What in the world is going on with your LPs? That's not my problem, that's your problem. And she handled it really well, but that's another one that sits with me. And then the third is uh Dr. Sony, and when she was initially pitching uh her MD, and the one investor flat said, menopause isn't a thing, and women's libido is not a problem to be solved. And you just sit there and you she goes, I've been a practicing clinician for 20 years. I know exactly what this is, and uh, and this man across the table is going to tell me it's not real. That's great. Love that. So many of the stories had a similar dismissal in them, whether it was a breast cancer story or a you know, is that still a thing that came up in Marissa's conversation? For me, the reason we hear that so often is a combination of lack of awareness and just deeply embedded stigma. And what the world has done quite well is wrap a lot of a woman's lived experience in some version of shame. And so we're we're not a we're not supposed to have profit because it's dirty. You know, our our bodies do weird things that we can only whisper about. We have to keep our ambition tempered so that he's not offended or doesn't feel outperformed. Or my favorite one, like we're bad with money. And these are just these tropes live out in the world, whether it's commercials, TV shows, movie scripts, like it is literally everywhere. And once you look for it, you can't not see it anymore. You will find it across everything you watch and everything you listen to. And so we have embedded these notions and these uh like social almost norms from when kids are young, they're seeing it on TV and they're hearing it out in the wild and in the world, and we we attach weakness to femininity and strength to masculinity, and we do that over and over and over again. And we consciously have to shift those those juxtapositions in a way where that's not true anymore. And and that's why I think it comes up all the time. For me, the fixes for that are one, we again need more women making content. And Reese with her spoon is a great example of doing that. And and she has a great uh, you can find it on YouTube, but she one of her acceptance speeches, she she said her the reason she wanted to make movies is because every single movie she scripts, she saw there would be some point where the lead female said, Well, what do we do now? What do we do now? What do we do now? And she said, How how often in a crisis does a woman not know what to do? It's impossible. She always knows what to do. So I had to write stories that made that true. And that shift has to happen. And then the other thing, and Meryl Streep said this really well in a panel a couple of months ago, just said, Women have learned how to speak men. Men haven't learned how to speak women. It is the best mic drop I've heard in a while. And that that is a language and semantics conversation where instead of not talking about our periods and our menstrual pain out loud, we should talk about our periods and our menstrual pain out loud. We should say, look, like I've really got some cramps today. I'm gonna have to go a little slower. Can you help me out with these two things? Because I just need some extra support and asking for it and getting the support or saying vagina on a panel and be like, it's okay. If you can say elbow, you can say vagina. These are body parts, and making it more commonplace to use all the words that relate to our lives so that it doesn't get chuckled at or giggled at or snickered at. And then the more that happens, the less often these weird dismissive statements will happen because it won't be weird and it won't be that thing over there that I don't have to think about. It's actually something the men also know about. You know, so much of this goes back to a mismatch of values. And for a lot of founders, for me, the real need is to sniff that out early and to find a way to not get three rounds into diligence and then find out you have to scrub a deck of major language. And I believe founders can do that one by asking really good questions up front and understanding what their values are, understanding what other investments they might have made that are similar or in the same space that they are in, talking to other founders in that fund's portfolio and saying, how are they? Who are they? How do they work? Have their LPs been involved? Do you see any awkward behavior that I should know about? And a lot of this is it's in the it's in the dirty details of how a fund makes decisions because something like that is it's a vice clause that's sitting down in some term sheet when they took that money that said they can't invest in X, Y, or Z. And they still took that money. And so asking about those limitations up front instead of it being the last line in the sand when you're fundraising is really important. And that that comes back to founders standing in their confidence, knowing their shit truly, and then living in some level of abundance rather than scarcity. Because I talked to Annie about this on that episode, is the reason you get that far is because you might believe that that's the only check you're going to get. And it's been so hard and you've been fundraising for so long. You go, oh my God, if I don't get this check or done. And we have to pull ourselves back from that and keep a lot of conversations live and be able to navigate with some fluidity and know that there's another check somewhere else. Because so much of this is embedded in the power dynamic. And if we don't allow the power dynamic to take over the conversation, we we often have more options than we think we have. So it's interesting the question of whether there's some deliberate manipulation in how the power dynamic works in this ecosystem. Uh I've seen versions of that where the investor leverages the pain dynamic or the emotional dynamic, or the what is maybe not spoken as the scarcity dynamic to lead a founder along, to make it sound like they're interested and they're not interested. Uh, I don't think it's uniformly across the board something that is real. And if it is, it's more unconscious than conscious. So it's not something that's happening like I'm going to string this founder along for a long time because ha ha ha ha, I'm a terrible person. It is just a you don't want to be rude, you don't understand the business, you think there might be something there, or you're just responding to emails and follow-up and not saying no. And that is more of what I see is that the continued interaction and interaction and interaction when the investor has no intention of investing, but simply hasn't said no. And it just the quick no is more valuable than anything else in this space. If you're not interested, say so. So that founder can move on and everybody saves time. But a lot of investors don't do the quick no, they do a very, very long no. And much of that time was actually not even interested in the first place. It's interesting because as I'm fundraising as well, uh, I'm seeing some really interesting dynamics happen. Uh, and one category is there's a whole set of founders uh who are not of the female persuasion who are constantly peeing me on LinkedIn, uh seeking to talk, wanting to pitch their business, etc. And a good handful are in healthcare and and in women's health in particular. So that's not completely unreasonable. But if you look at my profile, you it screams women up and down. Uh, and so the likelihood that I'm going to get into a second or third round of diligence with a male founder who doesn't absolutely have senior women on his team or a female CEO is is half unlikely at the very least. Uh, but I will still get those those inbound requests. And so what I've started to do with that set is really great to meet you. I'm not deploying right now, but let's stay in touch. And if I can help with introductions, let me know and leave it at that and not get any further into the conversation. The other half is the really fantastic women who reach out who are within one, they have to be within thesis. And I do think most women do a reasonable job of investigating that. I still have probably 25% who don't fit or they're they're doing something that's way out in a different category, and I have to nicely say they're not in thesis. Uh and then, you know, the one most of the problem or most of the hurdle or feedback I provide is often on the storytelling, and it's on how they're positioning what the business is about. And I don't know if this is a combination of how we've coached women in the sector or in the ecosystem and our inherent storytelling nature of how women share stories and how we lean, but there's a lot of empathy leading a lot of these stories. It's a lot of pain, is my personal experiences. I went through this myself or my family, et cetera. And that's the reason I'm building this business. And it takes until page five or six to actually get to the size of the market and the revenue model and how it's going to grow and how big this can be. And that it's fundamentally too long. It has that value story has to happen up front. And that's probably the biggest point of feedback I give founders over and over again is it's taking too long to get to the money. And if you're, I would love for you to go back and try on whatever evening you want, with you know your beverage of choice to rewrite the story and not mention the pain. Try it without the pain in there at all and see what it sounds like and how that feels as you talk about it. Because then you're leading with data and money and metrics and other things about what the business is about rather than the pain that might sit underneath it or even the pain that it's addressing. Because while I appreciate all of that and it's real and important, it actually doesn't matter at the end of the day because you have to deliver on sales and growth and value against that use case, but that can't be the reason I write the check. The reason I write the check has to be about you making money and me making money so that there's an exit in the future. The leading with our personal story also puts us in a corner on how personal the feedback feels. And that's the other reason that I will provide the feedback is that the problems happening in this system are not personal. Some of the, if you listen to both seasons, so many of the themes are so consistent. So many of the behaviors you hear over and over and over again that it's not personal. It is not me and something I'm doing. It is how the system is designed and it's how it'd been working for a long time. And so this very unfortunate blend between personal life and professional life ends up showing up in a lot of different ways. It's why the bad behavior happens, it's why the propositions happen, it's why people feel like they can invite you to dinner to talk about investing and then actually treat you like a dinner date. And you, I should have never accepted that dinner invitation because our mindsets weren't in the same place. And there's at least one or two stories where the waiters come by and say something to the effect of, oh, who's who's your dinner companion today? You go, and the investor doesn't say anything to correct that. You go, I'm not a dinner companion. This is a business meeting, but that doesn't get corrected. And so how how we respond and navigate the system means separating ourselves from the personal dynamic and saying, no, these things are real and they happen, but it's not personal. And I have to have my strategy set up to respond to it and to not go to the dinner meeting and say, hey, you know what it'd be better if we could do lunch because I'm otherwise occupied in the evening. And if that's a deal breaker for the money, maybe that's something we should know up front before we get there. And and listening to our gut on that is really important because if we got heebie jeebies from a guy we might be dating, and we're like, oh, I'm not going to dinner with him, maybe I'll have coffee. And if he declines, then you go, well, fine, I'm out. I'm not gonna put myself in that situation. That same, those same spidey senses have to apply. The single most common thread running underneath so many of these conversations for me is underestimation. For a whole host of media-driven and society-based reasons, women are systematically underestimated in almost every sector that we're in and that we operate in. And in venture capital, it's almost egregious. It is just this question of, oh, can she run a business? And then my God, she has kids. Can she run a business? How will that work? Oh, what if she decides to have kids? Oh gosh, what's gonna happen? And you come back to of course we can run a business. Do you know how much multitasking any woman does on a given day? And then you add children to the next. There's all there is a saying out in the world, if you need to get something done, you give it to a mom because she'll get that done. Because that's how her world works, right? And she also has a career and is doing all those things. But those notions of effectiveness don't run in this ecosystem the way they should. The other two parallel problems are network failures and semantics. Network failures meaning we have a lot of people who hold the money, and then we have founders looking for money, but the crossover of social capital has not moved as fast as we need it to. So investors continue to write checks to people that look like them. And until that modeling starts to shift and there's more profiles getting into their purview, we're not gonna move capital as fast as we want it to. We're just not gonna see it shift in the way that we want it to. And that's a matter of relationship building and networks and being open to having people that aren't like you in your inner circle or sitting next to you in an investigating meeting or being part of the team that makes decisions and/or who you're meeting, who walks in the door to pitch their company and hearing their whole story, regardless of what they look like. And then the semantics, this is again back to my storytelling point, is uh telling stories that lead with value rather than those that lead with pain. And then we're here to prove opportunity and not secure belief. And we need pain, as you mentioned, with with marketing, uh, it always anchors on some level of emotion. It's just getting there in a page or two and not in five. So that you can show how big the potential is, how much more expansion there can be. And that's what's going to get an investor to lean in. And that's what I need more of the ecosystem to be doing. How we really shift the ecosystem and change these dynamics, near-term and long term, for me is maybe two or three things, but the biggest one is more women involved as check writers at the general partner level and as limited partners in those funds and as angel investors. And that's the part we're missing right now. I believe right now, as established funds, you know, including fund ones, fund twos, through, we're probably a 15% of the check writers are female, which is which is low. It's not great. And it it means, and even then, I've met a number of them who still struggle to put anything about the health of women in front of their investment committee. And they are continue trying to figure out how to position it, how to talk about it if we stick with women's health, on how to get that past the line in their ICs. So that we have to fix that problem. And that's both a matter of open-mindedness in those investment teams and really being broader and also more specific about their investment strategies, because just because we call it women's health doesn't mean it's not a viable opportunity. It's also not niche. There's, you know, there's a lot of different ways to talk about it to drive capital to it. And then the other is the demographic change in who's coming into venture as young people, writing checks, launching funds. If we count, I just had a dinner last night and we were talking about this. If we count all of the college grads and MBA grads who are now pursuing venture capital as a career, that 15% goes up to almost 25% in terms of representation. It's significant. And it's not just more women joining existing funds, it's actually young women coming out of MBA, their business school programs, and launching their own funds and pursuing their own fund one because they can probably pull 10 million together across their networks and start to write some checks. And they've been doing this in their their MBA program through student-led funds. They've already learned how to do it. They've built the mechanics, they understand how it works, and they can bring those same people out, same people along and reach into the rest of their network. And, you know, 10 million is great for a fund one. And now you start to have traction and growth, and now we have more representation in the system. And that's that's one of the biggest levers that has to change is who is leading the funds and what kind of checks are they writing and where. And then the second is getting more women involved as limited partners in those funds. And with the wealth transfer that's underway and with the amount of capital that's going to land in women's hands, it's a huge number. We're in $80 trillion now, is the number floating around most recently. The hurdle is that financial fluency is not consistent across the women that this money is going to. It's maybe 50-50, and I might be generous, but they don't know. We don't know what's going to happen to that money once it lands. It may sit in savings accounts and sit as cash, which is probably the worst possible situation. It may end up in philanthropy, which is wonderful, but not as effective as we might want it to be. Or it's going to end up in mutual funds and public markets, which also has its hurdles, right? Which may actually be getting a little bit worse given some of the more recent dynamics with IPOs that have happened. So we just have to get more financial fluency in front of all of these women who are going to have capital in their hands and have them meeting fund managers, thinking about alternatives, understanding what it means to diversify, taking high risk because they might get high reward, and placing those bets and building the muscle to do it. Because the reason male investors make decisions over a weekend, which they do, is because the muscle is built and they've been doing it for a long time. Women have not. So it takes five, six months to make a decision on an investment when we have to be moving a lot faster than that. And the the two examples I'll pair with that is if we were going to lose NPR because the government had pooled their public funding, and Connie Ballmer stepped in and gave them one of their largest philanthropic gifts that they've ever had. And that is a woman making her capital work for her against something she cares about. And it was her. She led that decision. And she decided this mattered to me because she wants journalism to live. She wants high quality journalism to live. And she made that decision. If more women made those kinds of decisions and activated their capital that way, just consider what the world would look like. The things we could change and the levers we could move. We could fund everything that the NAH has driving. Off a cliff, if more women were moving their private capital. We could stand on pedestals and do the things that a lot of unfortunate men are doing right now if we had troves of private capital. Let's do that. And then we change a lot of things. The viability of venture as a career path coming out of business school is a big shift from when we were in school, which might age us, which is fine. Everyone knows how old I am. I'd I believe a couple of things have changed. One, uh career, how we perceive careers and the flexibility of our lives within those careers has changed a lot. And so when I graduated from undergrad, and then when I graduated from business school, I was in consulting. And consulting comes with the dynamics, right? You're on the road all the time, you work all the crazy hours, you're you're listening to part reading part or emails at 10 p.m. on a Sunday, and you got to get it done before the next morning. There is no question about getting the work done. And you trade off the rest of your life to do that for whatever number of years you want to do that. That mentality simply doesn't exist anymore. And so, as much as there are more women going into entrepreneurship because they want to be their own boss and they want to lead their lives and still have the flexibility for the other things they want to do, venture is becoming another way to do that. And a place where I can have impact, I can do good, I can make money, and I can be part of building something bigger than me in a way that is informed by my belief system and my values and the role I want to play in the world. The other layer in that is that corporate constructs and the hits on diversity, the problems with promotions, the continued problems around behavior that even exist in corporate, while we were growing up and willing to ignore and or tolerate so many insane things, and we would just turn around and keep working, this generation simply won't. It's completely unacceptable. And so if they see bad behavior or someone says something off-color to them, they're going straight to HR. And if HR doesn't act, they're out, they leave, forget it. I can't work in this environment, and I simply won't. And so knowing that those dynamics existed for their elder siblings or their parents, and knowing that that's the option that's always been there and it didn't work, hasn't worked, and I saw my mom go through it, or I saw my sister go through it, I'm not going to. I'll build my own. So I've had a lot of weird things happen in my experience as well. Uh, the two stories that I haven't people know, but I haven't talked about on the pod. One is while I was fundraising and for my last fund, and there was a very senior executive woman, SCP of wealth management at firm not to be named, and she was ready to go, gung-ho, wanted to write a check, loved everything about what we were doing. And she said, I I just I want you to meet my husband so he knows what this is about. And so, can we just do one more call so I can get him in the loop? Great, let's do that. So, myself, one of my business partners, and her and her husband got on a Zoom call and he met us, he said hello, he was very kind, and then he started to ask about our thesis. Now, our investment thesis at my last fund was female founders building in health, wealth, and sustainability, specifically solutions that support women in their daily life. But this was a couple of criteria had to get checked for us to go down the path of writing a check. And no matter what we said or how I described why, he could not get away from the fact that we were not writing checks to male founders. It was just a hurdle he could not get past. So he asked me three different ways. So if a male founder had a cure for breast cancer, you wouldn't write them a check. And I said, Well, no, that's not in thesis. There's a lot of female founders also working in breast cancer, and I'm spending time with them because one of them may have a cure as well. And I'll remind you, we're trying to expand the 2% of the population that doesn't get funded because all of the because there are 90 for every two of us writing checks to women, there's 98 writing checks to men. So I'm very sure he's going to get funded, but I'm not sure that she will. And I want to make sure this innovation grows as well. And he said, But you're you're just leaving money on the table. And you're compromising returns. I said, Well, no, absolutely not. I'm not compromising returns. I'm not. I believe very strongly that those funds are compromising returns because they've been leaving this audience out of their thesis for years. So I'm gonna go make money where nobody else has. This is my arbitrage, is to go after this audience that nobody has funded and make money there. And no matter how many ways we said this, he could not get his head around it. And we ended up wrapping up in 35 minutes at and she didn't write a check. It was wild. It was wild. And so that and it's it has sat with me because you go, there's so many embedded questions in that. Like one, she's a wealth manager, she couldn't make her own decision. Two, he has that much influence over her decision making. And three, and this is maybe like the most unfortunate conclusion I came to is God, I hope the rest of their marriage is okay. Because the dynamic I saw on that Zoom call was I was like, oh geez. Homegirl, if you blink twice if you need help, because I don't know what's going on here. Oh God. And then the the other one, which is from my consulting life, uh, this was was a really they were a great client. We did great work with them. They had a very senior client on the team who was a very, very like frat boy-like, just you know, very senior, but had been there a long time and could kind of like move around the room and do whatever he wanted. And we had had a big meeting, and then we had gone to dinner, and now we were at he owned a like a bar that we all went to afterwards, and so we were all hanging out there, and the whole team was sitting at this long table, a senior partner, the next senior partner, and then me, and then the team. And the senior client guy sits down and he says, So talking to, I'm gonna call him Gary, talking to the senior partner, I go, So, Gary, how many women have you fucked? Oh, and then just sat down with his drink, and everybody at the table leaned back, and we were like, Did we all just hear what he just said? And he and he just kept talking as if it was no big deal. And uh, our senior partner engaged in so much that he didn't like check down the question and walk away in a huff, but he kept it cordial. And then little by little, we all just got up and left the table. And the partner next to me was just laughing. He's like, I cannot believe he just said that. I was like, No, I can't believe that either. What did we hear that? Wild. And then what happened after that, because this is a combination of you know what's happened to us as people growing up, you know, 20 years ago in these environments, to what the generation now is willing to tolerate, is there were a lot of conversations over the next couple of days about why me and the other partners sitting next to me hadn't like fist on the table, that's inappropriate, you can't say that, and we're leaving. That's what the junior team expected us to do. We didn't do that because we have calluses for these things. And we were just like, also, it also happened to me, and so we're all gonna get up and leave. And and everybody was kind of stunned, but the junior teams took such an issue with it that one of the young women, she just raised her hand the next day and said, I want to roll off, I can't work on this anymore. And then the other one did the same thing two days later. And then because the two of us hadn't said anything, we became complicit with the bad behavior. I became part of the problem. The generational difference for me was so stark in that moment because I was like, It, I don't, I don't, I had to react also, it also happened to me, but that didn't it didn't matter because I hadn't stood up for the team in that moment. So I was part of the problem. I tried to understand it and I get there to a point, and then I still come back to it happened to all of us, and he shouldn't have said it 100%. But to feel to have the narcissism to sit down at a table and say something like that to the other male partner on our side while the whole team is sitting there, that is potentially one of the most egregious things I've ever had happen. There's something I will say to founders fairly often that we can't play the game that we want, we have to play the game that we're in. And that takes navigating and understanding what's going on and navigating it accordingly. And there are founders who I'm dear friends with who, when they were getting close to their Series A rays, they very deliberately went out and hired a very smart young white man to be their CFO because they knew that their fundraise would go fundamentally different if he was there versus not there. And one version of that of a reaction could be, oh, that's like selling that's selling out, that we're caving to the system. And then the other version is like, no, you're just being strategic and you're getting the outcome you need, working the system as it's designed. But there's like there's a notion in here where like where's the line in some industries on on how far people will go? Uh, that there are versions of that in VC where you're, you know, just hire hire the really smart guy to be your CFO and get the raise done, right? And not have to kind of fight the battle over all women all at once. Thanks for listening to the Capital Flex. If today's episode hit home, share it with the founder you love and follow me on LinkedIn for more.