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How to Get the Yes: The Art of Persuasion

Watch a conversation with leading women founders and funders as they discuss challenges, insights and best practices for successfully achieving that “Yes!” You will hear from a panel of inspiring women who will offer engaging perspectives on what has — and hasn’t — worked in convincing others and on lessons learned.


  • Erika Cramer, Managing Member and GP, How Women Invest
  • Bianca Caban, Principal, Heartland, and former CEO, Sheworx
  • Brittney Riley, Co-Founder, Female Founder School

Nathalie Miller, Relationship Manager, First Republic Bank (moderator)

Read below for a full transcript of the conversation.

Nathalie Miller - Hi, welcome. My name is Nathalie Miller and I'm a Director on the Palo Alto Tech Banking Team here at First Republic. Thank you all for joining us today for the webinar that we're hosting, How To Get The Yes: The Art of Persuasion. There are so many instances in VC and in tech when it's critical to know how to persuade. But how do you do it? How do you convince others that you're right? And do tactics differ when you're talking about different topics? From go-to-market strategy to pitching a deck, to growth, to product, to hiring the right person. We're very excited because we've partnered with All Raise Female Founder School, How Women Invest and Kranz to bring together a group of inspiring women for this conversation. Today, we have Erika Cramer, The Managing Member and GP of How Women Invest, Bianca Caban, Principal at Heartland and former CEO of Sheworx. And Brittney Riley, co-founder of the Female Founder School. Today's format will be informal, each speaker will give background share stories about persuasion and challenges specific to women. The ultimate goal is to share tactics so that you can walk away with concrete examples of how to get the yes. And quick housekeeping before we begin the discussion, we'll be monitoring the Q&A, so feel free to submit your questions using the Q&A chat below and we'll be answering these during the discussion. And without further ado to kick things off, I'd love for everyone on the panel to quickly introduce yourselves and give some background as to why you're a part of this conversation today about the art of persuasion. Bianca, let's start with you.

Bianca Caban - Great, thanks so much, Nathalie, thank you for having me. Hi everyone, thanks so much for joining us today. My name is Bianca Caban, and I'm a Principal at Heartland Ventures. We're a Seed and Series A fund based in the Midwest. I'm actually based in the Bay Area and I focus on deal sourcing and co investor relationships out here. And we focus on construction tech, manufacturing tech, logistics tech and a bit of real estate tech as well. Prior to that, I was on the operating side of things in tech, working at Republic, which is an equity crowdfunding platform that's spun out of angel list in 2016. And so happy to share some perspective on equity crowdfunding, which I think is a new asset class that women are actually outperforming in, which is really exciting. And at Republic, I led our acquisition of Sheworx, which is a global female founder community and built a curriculum and content program for female founders. So this event really speaks near and dear to my heart. And then prior to that kind of had a career in financial services back in New York city. So really excited to be here, thank you so much again for having me.

Nathalie - Erika.

Erika Cramer - Thank you, Nathalie, and thank you to First Republic for sponsoring this event and Kranz for bringing us together. So I'm Erika Cramer, I'm 25 year-veteran investment banker turned venture capitalist within the last few years. I'm a part of a family office. I spent 25 years in investment banking, M&A advisory in the financial services sector. And I am the co GP and Managing Member for How Women Invest which is the sister entity to a nonprofit organization called How Women Lead. And How Women Lead is a 15,000 member network of accomplished women like the women on this panel. And it is all about elevating women in leadership, whether it be in corporate boardrooms, in C-suites, in whatever circumstance. We were birthed out of pandemic in 2020, as the sister entity to How Women Lead, and launched our first fund in August of last year. We are intentionally designed as a $10 billion venture fund, because what was revised under the 99 investor rule now allows for up to 249 limited partners in a fund, as long as the size is $10 million or smaller. So that allowed us to provide access to many first time female accredited investors of which we have 211 LPs, predominantly comprised of the members of the How Women Lead network.

Nathalie - And last but not least, Brittney

Brittney Riley - Hi all, great to be here today. My name's Brittney, I'm a co founder at Female Founder School, a community that provides targeted and tactical advice for women founders, starting at the earliest stage of their journey, often before they raise capital or fully built out their initial product. I also am an angel investor, so I can kind of speak from that lens within persuasion. And then for my day job, I work for a firm called Pivotal Ventures, which is the executive office of Melinda French Gates. In that work, I worked primarily as an LP investing in venture funds. So hopefully I can bring the kind of perspective from the full ecosystem and persuasion that's required kind of across the board.

Nathalie - Great, and so we want to get to the broader conversations and tactics, but first would love to hear a little bit of the personal side, so we'd love if you could each talk about a time when you personally had to persuade others but failed, or maybe persuaded others and succeeded. I'm curious in particular about what key differences or variables you can think of that contributed to either your success in convincing someone or not. Let's start with Erika this time.

Erika - Sure, so I spent most of my career as an investment banker and it's all about persuading a buyer of a company or a seller of a company. And I would say that, you know... And this is very much in a male dominated environment that I had spent most of my career. So I had many failures that I could probably talk about. One that comes to mind though, is I was representing a firm that was acquiring other money management firms. And we had approached a company that met all the buyer's criteria for an acquisition. And it was actually a female founder. And I thought, you know, I had made this really unique connection, there weren't any women that were leading successful asset management firms. And I spent a fair amount of time trying to address and convince her why selling a portion of her business to this acquirer made a whole lot of strategic sense. Why it was going to be a fabulous dream come true in terms of economics, in terms of the things that they could do together, in terms of the synergies that were to go into effect. And I had approached that transaction twice actually, so I hadn't given up, I thought... You know, I said I'm an athlete on the side and a marathoner and I wasn't going to give up, I thought this was a perfect marriage that should occur. And it ultimately didn't. And I realized that I had done a lot of, sort of post-mortem review of that deal. And what I recognized is that, she was just never going to sell her baby. This was her business, this wasn't... And she was going to give up a part of her identity and what she had accomplished in that transaction. And that was something I was just never going to be able to convince or change or persuade in that discussion, as attractive as the elements were going to be. She wasn't necessarily driven by the economics, not driven by money. And so being able to recognize that what really drives a decision, it takes some work, it takes some empathy, it takes some understanding and conversation for all.

Nathalie - Brittney, same question, do you have a personal anecdote around trying to convince someone of something, whether you failed or succeeded?

Brittney - Yeah. Like Erika, I have many failures, like probably all of us. But I was thinking about this question and I think, you know, there's... I had a funder that I was trying to pitch. This was that when I was at my previous firm called Village Capital, really a big deal that would have been kind of game-changing for our organization. Worked on it for about a year. And I think, you know, ultimately it didn't work out because I think our strategies didn't line up, what they were trying to accomplish wasn't exactly what we were trying to accomplish. And because we liked each other and, you know, kind of believed in what each other were doing, we were trying to fit that, you know, square peg in a round hole. And when I compare that with other relationships that are... You know, other partnerships that have gone through, I think... And gone through like fairly quickly or successfully with a lot of alignment, I think the difference is really that, one, I wasn't listening carefully enough for what they really needed. And then also, I, wasn't kind of focused on of building that relationship first, if there isn't clear alignment, and just focusing on that part of it and kind of waiting for, or looking for when, you know, there was a clear match. As I think part of persuasion is also knowing when to cut your losses and stop, you know, spending a lot of time trying to kind of convince someone. And instead you can just form a great relationship and keep in touch and I've seen that happen. And when the timing is right, it can really work out and work out very quickly.

Nathalie - Bianca, same question.

Bianca - Yeah, I was trying to think of a really good example, but I feel like, you know, Brittney and Erika shared really good ones. And I think just something that I want to build on in terms of what Britney just said is what's interesting is I think over time, what I've learned is that in terms of persuasion, basically, it's sort of an negotiation more or less. And in thinking through, you know, negotiations and just in general, I feel like a lot of times, you know, throughout everything we're doing it's sort of like little micro negotiations, whether it's, you know, trying to convince someone we work with to... You know, influence someone we work with to consider a deal that we brought to the table, or whether it's trying to convince on the female founder side of things, someone to invest in your company. I think in terms of what Brittney just said around thinking through what is the other party what are really their interests, and kind of where is there a potential middle ground in terms of what outcome you want, and what you think that they want, and how can you kind of get there. And I think really understanding that every single interaction is sort of a little negotiation in some ways, and really trying to understand what that counterparty cares about and what their interests are, and doing a lot of listening and asking questions, so that you can figure out what that middle ground is, I think, is a skill that I constantly am trying to hone all the time. But it's something that I've seen play out in little interactions, in larger interactions throughout my career.

Nathalie - And honestly sort of sounds like everybody on the panel is talking about user centered-design in some way, except for instead of customers we're talking about, you know, partners or investors. Would love to hear personal stories about advice that you've gotten along the way, whether good or bad. Bianca, let's start with you this time.

Bianca - So I'm trying to think, I think to me, when I think about advice that I've gotten along the way, it's really about, you know, if you think about persuading someone about an investment opportunities, something that's kind of top of mind for me now. I think at the end of the day no matter what you're trying to persuade someone of, it's important to sketch out, I think the opportunity using metrics and real compelling stories. I think that's something that I think goes a long way when it comes to trying to influence or persuade someone to believe in your vision or to back you or to take an action that benefits you ultimately. I think it's really about telling a compelling story and backing up that story with real metrics, whether it's data, you know, market trends, whether it's talking about, why you're building a solution that you're building based on an experience that you had that was really impactful to you and showcasing that this is why the solution you're building is so necessary. I talk to female founders and founders in general all the time now and what I'm really trying to understand from them is what is... Why is the solution they're building solving like a key customer pain? I mean, kind of going back to that user-centric or customer-centric view. And really trying to understand the ROI to that customer if their solution is deployed, whether that's in time saved, revenue increased, costs reduced. So I think for me, tips and tricks that I've learned along the way is when you're trying to articulate an opportunity or persuade someone or influence someone to see your perspective or take an action, it's really going back to really articulating the story in a compelling way, and then the metrics to back that up, whatever those might be. So I think those two things are something that actually female founders are actually really good at. And hence, we can talk more about this but hence why they do really well in equity crowdfunding, for example, it's because they're very compelling storytellers.

Nathalie - Erika, same question on advice, either good or bad that you've gotten around convincing others or trying to persuade them.

Erika - Yeah, I mean, having... The fact that I grew up in sort of a male dominated environment, I think I was forced to sort of think and act and talk even more like a man in a persuasive discussion. I think one of the nicest things I heard was actually representing my father-in-law's company. The hardest client I ever had was my father-in-law, right? Show up for Sunday night dinners and want to talk about business, I never got a chance to decompress from that deal. But one of the nicest things he said was I negotiated like a woman, I negotiated with grace. And I think... And I'm using a lot of female terms in this discussion. I'm talking about empathy, I'm talking about grace, I'm talking about really what it means to be persuasive is to be authentic. So if you're super passionate and you have the storytelling like Bianca just refers to, you have a vision, being your authentic self is super important. And your passion comes through, that's the number one thing we seek in female founders, and any founder that we invest in is do they have the passion? Because starting a business is very, very challenging, it's not easy. You're not only serving your customers and your clients and building, you're building a firm, you're running a business. And so having that vision and being able to combine that with grace and doing your research and coming prepared, knowing who your audience is, knowing what they seek, knowing what they want to gain out of this relationship, is I think some of the best forms of advice for being persuasive.

Nathalie - Brittney any... Go ahead.

Bianca - Yeah I just wanted to reiterate, it's funny, as I was prepping for this, I literally bolded make sure that what you're doing is authentic and aligns to you. So I just want to reiterate what Erika said. And one example that came through recently for me is I met with a female founder actually is totally coincidence that she was a female founder, and she's building a solution for subcontractors in the construction space. And I think one of the things that came out in kind of the story she was telling about why she was focused on this was she actually grew up with her father being a subcontractor, you know? And so she grew up in that, you know, small family business. And so while her career had nothing to do with construction whatsoever, she was actually a killer product and tech person. That small anecdote of how her father had a subcontractor business made me so excited about this, because I just knew she was so passionate about this solution and what she was building under the surface, because she had that personal connection. And it was just... You can't get much more authentic than that.

Erika - I love it, I know that founder and I love her.

Bianca - Well, yeah, exactly. So I just want it to just really reiterate that, you know, I think authenticity can come in so many ways and to find sort of personal connections into in things and communicating that is so powerful.

Nathalie - Brittney.

Brittney - For sure. Just two things I'll add to points that Nathalie and then what Erika made at the beginning, Natalie you mentioned kind of, it sounds like, you know, like a customer discovery process. One piece of advice I got was on the fundraising side was when you're fundraising you should also have an investor discovery process, and you should approach it the same way. And you know, maybe we'll get more into that. But I think, think about it just like your customer discovery you should be asking questions about every investor, you should be listening to them and you should be looking for alignment. And then the second piece of advice I got that kind of goes into this like doing your research a little bit was just... And it's more on the operating side whether it's like running a board meeting or if you don't convince your team internally, or, you know, doing a big sales pitch is just pretty much everyone in the meeting, you should already know what their stance is on what you're trying to persuade them of before you walk in. And ideally you only have one person to convince, especially if it's a group, otherwise. And so really the work happens beforehand and convincing people one-on-one. And when you bring people together, you should have only probably like one person to get over that hurdle, otherwise you're walking into a situation that you're not going to be able to control.

Nathalie - And that's super helpful. I like the directions, these different comments are going into, and it's kind of leading into a question that I'm very curious to hear your thoughts about, as we talk about things like speaking like a man or negotiating like a woman, and what does that all mean? Because research shows that women are pretty systematically judged based on their experience, whereas men are judged based on their potential. And for sectors like tech, and when you're dealing with VCs, et cetera, that's actually a lot to be up against, right? Because you're creating products, you're creating businesses, you're creating solutions for the first time in a lot of cases. So I'm wondering your thoughts on how women can overcome these types of biases. I don't know who wants to start with this, I'm sure everyone has an opinion. I'll go with-

Brittney - I can start, I can share my very quick thoughts. So, you know, I think first is just understand it's something you're going to go up against, and you're not going to solve all in one conversation, so it's not all on you. And I think we'll talk about that afterwards but, you know, I think there... I can provide some like specific advice, like try to attempt to flip the conversation, you know, make sure you're not all on the defensive saying things like, "I'd love to make sure we have time for the roadmap or the opportunity." But I think ultimately like any... You know, when you're fundraising, you're looking for people who align and believe in what you're doing. And so also knowing, you know, if you have to, you know, spend all of your time with folks that don't believe in what you're doing, they're not the right people to invest in your company. And I truly believe that there are investors out there now who are spotting or interested in opportunities that might be less popular or less let us interesting. And so if you're just banging your head against the wall like again, with that investor discovery, like maybe think about a different type of investor or take the feedback because I think... Yeah, that's-

Erika - I would agree. Yeah and I think, you know, we're a gender lens fund, but that should not be confused with being an impact fund which has different risk return profiles. We have traditional risk return objectives, right? We seek a 10 times return objective. So we test our female founders to come to the conversation with being able to demonstrate how they're going to make 10 times return on the money that we invest. Which means that they have to have a big enough vision. And inevitably we found many female founders who come to us with a great solution or service and has a huge enough TAM, So they've met her initial criteria in terms of TAM size. But what we have found is that often our female founders don't come asking for enough money, right? And that sometimes signals that they're not thinking about growing the business large enough. So we try to be hugely entrepreneurial centric. We're trying to... Because we're part of a a sister entity nonprofit organization that is all about closing equity gaps, we want this to be an experience for our female founders. So we've put a lot of work into our processes and the tools that we give to our entrepreneurs. So we ask them to fill out a jot form with very specific questions so that we're not wasting anyone's time, that we've clearly identified that there's a match at least on the surface in terms of what our criteria is, and what their product or service or solution is. So we seek an initial match before we even engage in discussion. Time is money and that's our... You know, it's a tough resource to come by especially in these days is we're adding commuting times to the discussions. But we give our female founders that checklist of the items that we want to see in a data room. We want them to be organized, but we're very, very clear upfront that this is our return objective. And we hope that you have a financial model that basically maps it out. It doesn't mean that we expect you to live by that financial model and hit each year's return objective, we know that no one can predict more than a year out of what their business will do, but it is very telling about how they think about growing their business, about how they see what the opportunities are how they think about hiring, how they think about building, how they think about raising capital in the future.

Nathalie - Bianca, did you have any thoughts on that question?

Bianca - I mean, I guess I would just add that it's something that Erika mentioned kind of in the very beginning around some of the assets that come with being a woman in business around, you know, being able to negotiate with grace or having a certain discipline. I mean, some of the things that I've noticed is a lot of times the female founders that I encounter have been able to do more with a lot less, have actually raised less money and, you know, there's longer timeframe between rounds because they've just been able to, you know, be incredibly disciplined both with their time, with how they're growing their team, with how they're spending money and just more capital efficient, which is great, it's an asset. So I think to extent that, you know, thinking through what are the unique assets that women bring to business and how can you use that as strengths and emphasize those strengths over maybe some of the other, you know, inherent biases that you're up against? because I think it's real. I mean, data shows, you know, I think first round came out with an analysis of their portfolio performance and their portfolio companies that were co-ed and had at least one female founder just outperformed the rest of them. So, I mean, in some ways, just again, leaning into the facts and the metrics and the data of the asset, that it is to have a female co-founder on the team and what she brings to the table

Nathalie - I want to also talk a little bit about the other part of this conversation, because of course there's the one side where we're trying to figure out how women in tech can figure out how to navigate the system. But then on the other hand we also have to think about what impetus there is on the system itself. So not just on individuals navigating, but how much responsibility should we be putting on decision makers so that they can check their biases and not overlook talented women who they might unintentionally sideline. I see nods. It's a big question, we probably can't solve it in this one go. Erika, do you have any thoughts on that?

Erika - Yeah, I mean, it's certainly part of the reason why we exist, right? We know that only 11% of the decision makers in venture are female. So that's part of the problem. Women invest in more women, women hire more women, women pay more equitably to Bianca's point. They are more capital efficient they return more money to their investors. We see this as a huge arbitrage opportunity, right? It's a huge investment opportunity that here we are, we're women with capital and we can invest in female founders that we know will they will persevere and they will achieve, and they will return our investment objective. Half of my week is probably spent talking to female founders, the other half is talking to other VCs in private equity and doing these kinds of events, frankly, because it's a mission. And maybe it's because of the fact that we're a sister organization to How Women Lead. And part of it is movement building and awareness and training and creating safe community for discussion. But whenever I have a conversation with an all male team VC, and I talk about what our investment thesis is, and they talk about what theirs is, they sometimes scratch their heads and say, "You know what, wow that you talk about it, I think 30% of my portfolio are female founded companies and they tend to be... They actually are my best performers." So I mean, you know, we need to create that systematic change. I think what's challenging for us is some of the constraints. We know from an institutional investor perspective, it's hard to allocate capital unless you check all the boxes in terms of assets under management size, you know, track record, infrastructure, compliance, all of the things that make it very challenging for an emerging manager to make an impact. And I think we need to change some of those systems just like my partner did with changing California State Law mandating corporate board diversity, and now you see it all over the place, right? Now you see NASDAQ and it's become a mandate. I think we'll need to have some of that systematic change, whether it be... I don't know why they couldn't have a $100 million fund with 249 LPs versus a $10 million fund. I don't understand the rationale behind that decision. So I do think they need to work with regulators and advocacy groups, to see some of the systematic change take place.

Brittney - Yeah, I couldn't agree with Erika more. And I think, you know, this way I can put on my hat as a LP who invests in venture funds. You know, I think ultimately like a key skillset of an investor is to have decision-making skills and decision-making frameworks for making the best judgment calls. And if they're not incorporating... If women or people of color are not, you know, if they're not investing in them, like how many studies do we need to show that that means that they're going to have less returns or less promising returns. So we should expect it as part of, you know, part of just making good decisions and making good investment decisions. So on the LP side, you know, we think it's crazy to... But most LPs don't ask or expect or track, you know, funds to invest like, you know to report out what type of... Where their capital is going or what type of founders they're investing in. And so as that starts to happen more and more, which it is, I think investors will also be finally kind of forced or incentivized to kind of put their money where their mouth is, you know, instead of just maybe opening up some mentor office hours, actually having to report on where their capital is going, and how they're making those investment decisions, I really believe will help them change the ways that they are making investment decisions or developing those relationships. Because obviously that there's kind of breakdowns throughout their whole process, along with all of the structural challenges that Erika mentioned as well.

Nathalie - Bianca do you... I saw you took yourself off mute, did you have something-

Bianca - Yes, I think just I think what was said really resonated with me. I think it's in terms of the ecosystem, it's not just about, you know, how do you diversify and invest in more female founders, it does require diversity among all the stakeholders in that ecosystem at the investor level, at the board level, even at the LP level. So I think that there's a lot of work to be done. And I think, you know, the steps that were taken in terms of mandating, you know, a certain percentage of women on boards, that's really important because we see that, you know, the results show that it does have an impact in terms of female CEOs, because you know the boards hire you know CEOs of companies. And so if there are more diverse decision makers at that level, it will kind of trickle down. And I think it's really important. It's something I think a lot about just on the personal level, in terms of thinking about our funding, in the diversity of our LPs of our, of our portfolio companies, et cetera. And then also just, you know, a good friend of mine basically carved out a portion of his company to diverse investors and it's called the diversity rider. And I think more and more founders are going to be doing this. And as founders have more and more power, which they do increasingly kind of, you know, forcing the issue a little bit to say I'm going to carve out a portion of my round for diverse investors I think is another amazing and really important step. So I see this happening more and more, which is which is exciting, but there's a lot of work to do throughout the whole ecosystem for sure.

Nathalie - I can see that this is sparking interest, the audience is typing in questions. We can answer them towards the end, but definitely feel free to keep adding in your questions to the Q&A because we'll get to as many of them as we can. Taking a quick step back, do you have thoughts on women sponsoring or uplifting other women. We've observed that sometimes women in our ecosystem can be great advocates for others, but other times women who've made it through the glass ceiling, end up recreating the glass ceiling for others. For example, women, VCs who actively actually avoid investing in other women-run companies for fear of being seen as favoring women. We'd love to hear some thoughts on that phenomenon and whether or not you think it's changing.

Erika - I think it's changing for sure. The more movement building awareness and discussion around this, I think creates a safer environment for women as investors to recognize their own inherent biases. We're also.... So obviously we're a gender lens fund, so we are on... And we're purists with it, right? We don't invest in male-female teams, we're investing purely in female founded businesses. And that's not meant to penalize women who have had to bring in a male CTO or a male CEO as a co-founder, it's just that we want to create that container where women don't feel like they have to do that in order to get access to capital. And we're built by community, and we have an amazing network of accomplished women who want to support and advise other women. We have a credo and it sounds a little corny, you know, in the beginning, whenever we start off a meeting and we talk about our credo, which is is basically to support her and reinforce her voice. But once that credo is stated out loud in a room full of women, it's amazing what comes out in a very safe discussion. And inevitably, you know, we've had female founders literally cry in our zoom meetings, like, "I can't believe I'm presenting to a group full of women." And that's what makes me so excited about what we're doing right now.

Nathalie - Bianca, Brittney, do you have any thoughts on that, the role that women play in sponsoring or uplifting other women, especially in this conversation about trying to persuade others?

Brittney - Bianca you can go ahead if you want.

Bianca - No, I mean, I think that something that happens a little bit naturally kind of in my experiences,. You know, part of my job is just building relationships with investors period. And of course it's given my background and my identity and affinity bias, I guess, I tend to have... Most of my meetings are with other female investors just organically. And I think that, you know, in some ways you can use the biases that we have and again, in a positive way to say that... You know, am I experience, I haven't seen where other investors that I speak to have a negative bias for female founders. In fact, it's the opposite. I think we kind of give each other a high five, like, "I'm really excited about this female founder, you know, I'll connect you to her." And I think it's something that we find joy in throughout our day to day. So that's been my experience, but I think I would just say that, you know, obviously we all have biases and it's just human nature. But to the extent that we can use those biases as a positive thing to say, you know, for example, at my firm, most of my meetings take place with female investors just by virtue of my network and who I am. And maybe some of my male partners it's the opposite, but that's okay because we can kind of, you know, bring our... It can be an additive network in that sense and synergistic and really an exciting opportunity. So I think biases can actually, you know, be positive in some ways, and we can use them to make a difference.

Brittney - Yeah, for sure. The only thing I'll add is just that, you know, I think that scarcity mindset of, you know, I can't like invite anyone else in once I got in kind of comes from feeling alone. And so like, I'm very like, you know, hopeful that that's changing and watching it change as there's more communities for women to connect, more ways for women to connect and ultimately more at the table, I think that scarcity mindset kind of falls aside. I also just want to say on the flip side like I think the burden shouldn't be entirely on women, I think like studies show and, you know women spend more time on administrative tasks at work, women spend more time with caregiving at home, you know, the burden shouldn't be on entirely on women to uplift every other woman. And I think, you know, we should rely on everyone to do that. And look to everyone to do that. And I know in my career, both men and women have been incredibly helpful and sometimes honestly the men have more free time and more social capital to waste to make lots of introductions for me. And I've been very useful in that way. Whereas women I've been able to like either brainstorm with or commiserate with, or like, you know, be uplifted in other ways. So just want to plug like, you know, maybe we don't need to put all the burden on women because there's often a lot of structural or reasons why it's difficult to, you know, uplift every single person.

Nathalie - Very fair and important point. We'd love to... We talked a little bit about tactics initially, we'd love to expand more on tactical advice, things that people can walk away with. You know, we listed, you know, listening empathizing, building relationships, user centered metrics, storytelling, making sure you're authentic, et cetera. But I'm wondering if you have any thoughts on this particular context versus the wider universe of when you're trying to shift someone's opinion. So because contexts are changing all the time, people's opinions change, geography changes, sectors are always changing, do you think that there are specific tactics that are universally true no matter what world you're operating in when you're trying to convince others? Erika, we're going to go with you because you're nodding.

Erika - You know, I'll share something very personal. So my husband and I went through a communication retreat. We're married 28 years this year, and still learning how to communicate. And I think that some of the things that we've learned you know, when you're able to listen, repeat what you heard the other person say, and then you're able to engage in that discussion. So coming to a conversation really prepared, and really listening and then acknowledging what you heard so that the other person really knows that you've listened to what they said, you're more likely to develop trust in relationship over time. And I think that's a unique characteristic for women, my sense is that we built trust more easily, because we can share things more personally we're more open. In personal context, I know that as an investment banker that was certainly true, I didn't have a problem talking about like some of the issues that I was having at home with kids and, you know, work and balancing life, but you build trust with the other person. And therefore, when you asking for something to persuade it's a little bit easier.

Brittney - I'll just add, like, I think I was going to say the same thing, like listening, and it's all about listening and communication, I think regardless of what area of persuasion and I think my least favorite times being pitched by someone are when it feels like I'm being pitched, and I don't get a word in and I just, you know, maybe that founder walks away and it just feels like I hit every single point that I wanted to hit. And I talked, you know, I said it all perfectly and I walk away kind of drained and exhausted from the conversation. Ultimately like everyone's... You know, it's just about having a conversation and listening and developing a connection with people, versus, you know, having a perfect kind of pitch or saying the exact right words. And so I just encourage everyone to kind of think about from the beginning how can they make sure to incorporate more listening and more communication and less like, you know, emphasis on the same, the perfect, you know, having the perfect slide or the perfect word.

Bianca - The other thing I would add is it's kind of a version of passion, which I think we talked about but it's kind of like conviction. And I think one thing as women that we tend to do is we're very kind of balanced and focus on the facts, which is why maybe we, you know, female founders tend to not want to raise as much capital because they're like, "Well I don't need that much capital." But to Erika's point earlier, perhaps, you know, some sort of indications for VCs might show you ambition when you're really just trying to be practical. And I think having like that balanced perspective of something that's kind of a bit more natural to us, but if you know something that's helped me as I'm bringing deals to the table, and trying to convince others that these deals are compelling, is even if I internally don't have a ton of conviction because I see the various potential flaws, or I'm looking at but what about this or that, I'm looking holistically at the big picture, I kind of put myself in the mindset of I'm just going to have a tremendous amount of conviction in this. And so what would my argument be then. If I just had a tremendous amount of conviction, what would it be? And so sometimes that conviction already exists as a female founder, those that are on the call I'm sure you have a ton of conviction in what you're building. So just make sure that shines through and no matter what, there's so many reasons in early stage investing to say no but what is it that would get that other, you know, the investor to yes, and just focus on that. Don't worry about all the potential things that could go wrong. And don't worry about the balance perspective for a second, throw that balance perspective out the window and just focus on conviction and then building an argument around that.

Erika - I would just add, you know, venture investing, there's very much an art and a science to it just like with many things. And just to make the, you know bring it full circle and what Bianca just said, the conviction in your investment in a company comes very much from being able to trust that founder. And so building that trust because inevitably you're absolutely right, building a small... You know, starting a company, you're going to have many moments of anxiety and loss and not meeting objectives, the first board meeting that we go to I know there'll be an, "Oh, crap, didn't know about that in the business." There'll be some surprise, but as long as you have trust and conviction in the founder that's ultimately what you have to bank on.

Nathalie - So we're going to shift gears and open up to questions from the audience. I see that a lot have come in, my colleague, Kelly Caviglia, who also works on West Coast Tech Banking at First Republic Bank will be... She's been monitoring them, and she'll be introducing some of those questions so that we can bring them to light. I think there's a lot of interesting stuff about intersectionality, a lot of interesting directions that we can go in. Kelly, do you want to ask the first question that's come in?

Kelly Caviglia - Yeah, sure, thanks, Nathalie. Great discussion so far, everyone, I think has been really helpful and really insightful or both the male and female audience members. We do have a few questions. I know we've been talking a lot about what it means to be a female founder and some of the challenges that they're facing, but just to drill that down a little bit, we've had some questions on specific age groups. And so one particularly is, you know, advice for female founders over the age of 50. Really, you know, spotlighting most about when we think about tech, and we think about founders we always think about, you know, again that male in their hoodie sweatshirt walking into pitch, right? So what does that look... What does that turn out to be when that is the opposite of what walks through the door?

Erika - Well maybe since I think I'm the only one that is over fifty, I can start, and then I'd love to hear Bianca's and Brittney's perspective as well. The first two investments that we've made are investments in companies founded by not your traditional venture backed founder, right? These are mature women and we're not allowed to ask their age. But I think what attracted us to... First of all, it ventured very much about the community that you're in and your network, right? It's all about network. And so both of these female founders came through our network. And so it wouldn't be a surprise to you to hear that of the 15,000 accomplished women, most are probably within my age group, because we've made successes and can now be accredited investors and investing in other companies. But what we find most appealing about female founders that have a maturity and experience they're potentially a second time founder, so they've already gone through their startup experience and tried it out on somebody else before we invest in them. They've seen... They know what it means to have an institutionalized or an institutional quality company that they're building. So some of those aspects we find really appealing for later or more, not mature, more experienced female founders.

Brittney - Yeah, the only thing I'll add is just that, you know, the average age of a successful startup founder is 45. So I think like also dispelling that myth that it's a college kid in a hoodie, you know, that's like probably with the media gloves on too, but that's not actually who is raising substantial amounts of capital and knowing companies. So kind of owning, you know, your own experience and where you are and knowing that isn't always seen as, you know, like it's mostly not seen as a position of a weakness or, you know, in the eyes of an investor. They might get, you know, excited about some young new talent, but ultimately where the capital is going is into experienced talent, who knows how to build teams and build companies. And so the only thing I can say is just, you know, I think whether you're 22 or 50, it's owning... Or 70. You know, I've talked to founders who are 75 and incredibly impressive, and have lots of... You know, have had so much more time than I do to commit to building a startup-

Erika - Minus the valuable resource that many... You don't get much of when you're starting a company.

Brittney - Yeah, yeah, exactly. As Bianca said earlier, be authentic to who you are and what strengths that you bring, you know, because of that experience.

Kelly - Yeah and you guys have both touched on this already a little bit, but on the other end of the spectrum, you know, we have a question on, you know women of color, especially under 30, when you're looked at as inexperienced in life and work and the challenges that you faced there and kind of approaching the male dominated industry from that end of the spectrum.

Erika - I think for... Go ahead, Bianca.

Bianca - No, I was just going to say that, I actually recently spoke to a woman of color founder who I didn't know at the time, but I think she was like 23 or 24. I didn't actually know her age when I talked to her. But all that really came across to me was an incredibly smart, you know, ingenious person that had discovered, you know, a technology and was building a team around it and working really hard and moved her entire business in her life to Bentonville, to focus on a key customer there. And you know, it seemed like she was younger just because physically, she looked younger, but I didn't... When I found out her actual age, I was totally blown away because it didn't... I mean just the way she carries herself, and the way she answered questions and the way she just was... She had a very warm energy about her, so I think she totally embraced that. And it wasn't that she was trying to sort of act a certain way, she just seemed super authentic, but then was just focusing on the business and what she was doing. And didn't even, didn't even occur to me how young she was until I found out later on. I don't know if that's an advice, but I think it's just focus on what you're doing and what you're building. And if you have conviction and it's a compelling solution it shouldn't really matter what age you are.

Erika - And I would just add irrespective of age, we want to know that our female founders are willing to listen to advice. You know, we're outsiders looking in and sometimes when you're running and building a business you don't really get to see the full competitive landscape or the full picture we know we want to know... And sometimes it might be harder for an older founder to think about changing their systems or ways, but being able to take advice and use it as an opportunity, I think that matters at any age.

Brittney - Yeah, for sure. And I think like age is just one metric of experience. So I just said, I think the question states, like, you know, despite your work around your experience so ultimately it's kind of a lazy investor if they're just only looking at age as a metric of experience. But I do think, you know, just on the advice side I think every single founder should think about where are my strengths and where are my weaknesses and how can I build a team around that? And if the weakness is on experience like within a sector that you're working in or within you are younger and you just haven't had time to build a company yet, how can you build a team of advisors? How can you build a team of mentors? How can you, you know, build around you to highlight the... Or to kind of offset those weaknesses. Every single founder is going to have them. So I think, you know, a good investor is not going to just look at their deficits, but look like how they're building around them.

Bianca - Sorry, I was going to say, I think that's a great really tactical point on advisory boards. I just wanted to, you know, agree on that strongly. And now that I think about it, this particular female founder that I spoke to highlighted her advisory board and said, "You know, I've got this, you know the former CEO of X e-commerce business that's an advisor to me" And I didn't really notice it at the time, but now that you say it, Brittney, I think that's a great strategy for sure.

Kelly - Awesome. All right, we're going to have one more question and then we'll go ahead and wrap it up. I think we know the answer to this one, we've talked a lot about being your authentic self, you know, when you're talking to investors and pitching your ideas, but there is the idea of having a male beard. What I mean by that is really, you know, you're coming up with the solutions and the strategies, but having a man on your team, pitch the idea, be the sales person for it, kind of the face of your ideas. And what are your thoughts on that, have you seen that happen before, is it something that you've considered?

Erika - I unfortunately have seen it. I've seen... So as I mentioned, we're purists in who we invest, but sadly we've seen female founders have been told you need to have a male CEO because you'll raise capital faster that way. And they were advised by their advisory board or their LPs to make that happen. And so we're trying to change that. We're trying to change that kind of thinking and rationale and create this space and opportunity for women to come and hire the best people irrespective of what their gender is or what their race is. And we're tracking that too, as an investor, we want to make sure that they continue to hire with diversity in mind.

Brittney - Yeah, I mean, I understand the train of thought I guess, but I think ultimately it's kind of a short-term mindset and the in authenticity is always going to shine through that, you know? And so I don't think it's a strong long-term strategy at all. It might get you a one or two wins, but again on that investor discovery and process, like is that who you really want, to work with at the end of the day? So I don't know, hire the best people. Or find the best people to run your company with, it's going to be a long journey.

Kelly - Sure, all right. Well, I think, you know, after that the best advice we've gotten today is be your authentic self and really that will shine through at the end. So I want to thank you ladies for joining us today, the conversation has been extremely thought provoking. For everybody that joined us, thank you for joining us today, we appreciate you being here with us. We'll follow up with an email that includes all the details and a replay of today's webinar. We hope you enjoyed the webinars series on women in tech and venture. And thank you again for spending your time with us today, and we'll see what the next one. Thank you.

Bianca - Thank you.

Brittney - Thank you.

Nathalie - Thanks all.

Erika - All right, thank you, it was fun.

The guest speaker(s) is neither an employee nor affiliated with First Republic. Opinions expressed by the guest speaker(s) are solely their own and do not necessarily reflect those of First Republic. This information is governed by our Terms and Conditions of Use.

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