Cindi Englefield: How to Attract Smart Money and Transform Investor Relations

As women, we tend to be great with philanthropic dollars, right? We give money away. We carve out a piece of our disposable income and give money every year to great charities. I never want to take away from that. But think of your investment portfolio and your investment portfolio. You could carve out 5% of that and put it into impactful women owned companies or early stage companies that are innovative and they're making changes that are going to make the world a better place.

Hey, I'm Kwame Christian, and you are about to step into the world of Negotiate Anything, the number one negotiation podcast in the world, where we teach you how to make difficult conversations easier while getting more of what you want in the process. Each episode is packed with practical tips and strategies from the experts. We delve into negotiation, conflict resolution, and leadership skills that are crucial in both business and and in life. Whether you're closing a deal, managing a team, or navigating personal relationships, Negotiate Anything provides you with the tools you need to succeed. Our conversations are real, relatable, and most importantly, rooted in practicality. So if you're ready to transform your conversations and elevate your negotiation skills, join me on Negotiate Anything. Subscribe and listen on Apple Podcasts, Spotify, or wherever you love to listen. Let's make every conversation a winning negotiation. Cindy, thanks for joining us today.

Thank you. Thank you for having me.

It is our pleasure, my friend. So how would you get us started? By telling us a little bit about yourself and what you do.

Yes, My name's Cindy Englefield. I'm a serial entrepreneur, angel investor, business coach. Just really been focused in the last, oh, 20 plus years on helping female entrepreneurs. But most recently I heard that less than 2% of capital goes into the hands of female founders, venture capital dollars, investments. And it really sparked something in me. I had been an angel investor for 12 years or more and I just felt like, yes, there's a lot of reasons why women aren't getting these capital dollars as capital investments, but I really felt like angel investors were really the key to helping women like bridge that gap between friends and family money and when they're trying to get themselves up and ready for venture bigger dollars at venture capital level dollars. So I really felt like I needed to do something. So Mary McCarthy and I are my partner. We started accelerating angels and we are raising a $3 million fund to put $100,000 checks into the hands of 20 or more female founders with our first fund and building an angel network around that so that we can get a community of Women and men writing checks to help female entrepreneurs. We really feel it's, it's a nice, a white space where if women aren't getting the venture capital dollars, then it's an opportunity for us to get on in on an early stage investment and help get these women to hit their milestones and get traction and scale their businesses so they eventually become venture backable companies.

Incredible. This is such an important piece of work that you all are doing, you and Mary coming together to create these opportunities for more women. And really we have a win, win, win at least, right? Because we have the women who are entrepreneurs who have these great opportunities, these great companies. Now they get the funding they need to go to the next level. Investors now are going to be privy to new investment opportunities. And then I know both you and Mary care deeply about this. And so yes, it's good to have another successful business, but there's also that emotional connection you have to the work. So the fact that you all exist puts everybody in a position to accomplish their goals and keep on moving forward.

Kwame, if you think about it, women really traditionally, socially, you know, our society has put us not in a business world for the longest time. In 1974 we were actually the Credit Opportunity act was enacted so that we did not have to have a male co signer for our loan. In 1988 we had another. The Women Business Owner act helped us get business loans without a male signature on the loan application. So it wasn't that long ago that we really started making headway in business. So it's no surprise really that we are not equal as far as opportunities for investments. Many times women are perceived to be creating candle companies a little bit less lucrative, scalable businesses. Not to downplay the role of candles in our world. They're not tech companies, they're not high growth companies that a venture capital company or a private equity company would invest in. But that's changing. Women are in technology and there's so many more women creating very scalable, high growth, very important companies that typically women look to change, make big changes in the world. They see social, economic, environmental problems and they want to solve those problems and they create businesses to do that. So it's a win, win. You're right. Win, win, win.

Oh, this is great. This is great. And one of the things you touched on is the reality of inappropriate biases or assumptions that are holding people back when it comes to feeling comfortable making those investments. And the entre entrepreneurs then find themselves on the wrong side of psychology, sometimes trying to swim Upstream in these situations. And a lot of times the rhetoric around bias structures in place that are holding people back and those types of very real considerations can feel very disempowering to individuals who find themselves in those circumstances. So really, as we start to shift into the more tactical and strategic part of the conversation, I think it would be great to first start with the mindset that you bring into these conversations. Because a lot of times when we focus too heavily on the, the biases and the structures that are working against us, it almost turns into self fulfilling prophecies during the conversation. So when you find yourself in these tough negotiations, what is it that gives you the empowering mindset to aspire for more and negotiate effectively?

Well, you know, despite all of the biases and the lack of opportunities for women, they actually outperform male owned companies by 35%, giving their investors 35% higher returns and they exit faster. So for as far as investing, they're definitely going to give it an ROI that's higher than men. They also are very focused on profitability. I really feel like the negative is there. Yes, the barriers are there, but on the upside, there is a lot of ways to overcome it. Women sometimes feel like even men. A lot of times when you're in business, you have the fear of failure. Right. And what we, Mary and I have done is we created a foundation that will help sustain this organization and empower women to, through programs and education and equipping them with the knowledge that it takes to get their companies in the right position, to get backed by investors, to practice their pitch, to get their documents in order that investors want to look at, to get their product roadmap mapped out so that they have a solid plan in place and that they have an exit plan for investors to take a look at. So yeah, there are barriers that we're overcoming every day, but there's opportunities within our organization and other organizations, accelerators, a lot of business accelerators out there that will help. I think knowledge is power. Right. The more you know about what it takes to get an investor to feel like your company is worthy of an investment, the better and the more confident you'll be when you actually pitch for an investment. So yeah, I highly recommend accelerators. And also, you know, we're here to help too. We not only are we're going to invest or invest this time into helping founders get ready to ask for funding, but we're also investing in them.

This is great. And Cindy, I'm going to recap this and then I want you to tell me what you think of the recap because I'm going to extend a little bit beyond your words. So when it comes to your approach, first we have the belief in the entrepreneurs. You believe that the entrepreneurs that you are putting in front of these investors can deliver. And you know that because not only are they exceptional, they came to you at a high level, but also you are investing more into them by again, knowledge is power, making sure that you have programs that can help to make sure that they have the skills necessary to take the business to the next level. And they can also communicate that in a way that is, that resonates with the investors so they are more investable in the eyes of the investors. So the belief that you have in the entrepreneurs gives you confidence in the negotiation. And then you also at the beginning talked about the success rate of the women led startups. So you have data also to substantiate that your belief. And so really, again, you have that belief that we are worthy of this investment. And I know once you give that investment, they're going to deliver. Now, when it comes to this other element, and this is where I want you to expand on a little bit because you have this data, you believe this. And now in these conversations, we need to kind of transport that belief into investors who might be skeptical. And so now when we shift into the more strategic or tactical part of this, how do you communicate that confidence to the investors so they too share that confidence and then they take the next step in actually parting with that money?

Well, what I usually do is talk about the companies we've invested in and the caliber of companies because, you know, until you actually see, see the caliber of companies that are coming, you know, to us for investment and the ones that we invest in, I mean, we really look for companies to have over 100,000 annual recurring revenue. We want them to have a large market size. We want to be able to see a 10x return or more. And so I'll give you an example. There's a Dossey Simulations has a software simulation that we've invested in their company that will save lives. I mean, whether you can get a valve replacement or not to save your life or not is on the line there. And their software simulation is showing doctors that it can be done and they're going ahead and doing procedures and saving lives. I mean, very impactful type of things like that. And you know, there's another company that create, you know, the Flint, Michigan water bottle. They have to drink bottled waters because of all the pollution and the contamination. There's a company that goes to Flint, Michigan and grabs up all the water bottles and turns that water bottle breaks, shreds it, breaks it down into beads. Makes the beads into thread, the thread into fabric, and the fabric into clothing. I mean, women business owners are. They're smart, they're engineers, they're technology tech savvy, and they're creating great companies. They're worthy of our investments. What's different is the challenge of convincing people to actually write a check, you know, for this cause. It's early stage. It's risky, but I like to compare it to especially women. I'll talk about women because a lot of my investors are women, but not all of them. As women, we tend to be great with philanthropic dollars, right? We give money away. We carve out a piece of our disposable income and give money every year to great charities. I never want to take away from that. But think of your investment portfolio and your investment portfolio. You could carve out 5% of that and put it into impactful women owned companies or early stage companies that are innovative and they're making changes that are going to make the world a better place. So that's what I'm suggesting to investors, to think about it as an alternative investment, that it can make a return. And typically angel returns perform better than the public market. So it's high risk, high reward. Our company uses the best practices that are out there for developing portfolio that's going to be successful. And so that's what I tell my investors. But activating some investors into this, I mean, you know, Shark Tank, right? We're not all Shark Tank rich, right? Rich and famous. But you know, an angel investor has to be accredited, which is a million dollars worth of net worth or making $200,000 a year in general. That's the guidelines. And that could be somebody that's living right next door to you. You don't know, right? And this is really a mindset, you know, is this right for you? Are you willing to take a chance to help make changes, big changes in the world? And we feel like women founders are also. We kind of de risk our portfolio because of their performance.

Hey, everyone, it's Kwame Christian, host of Negotiate Anything, asking you to please do not skip forward because this is not a commercial.

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Well, I mean, you make an investment to make money, right? You want a return on your investment, so that has to be top priority when you're raising a fund or working as an angel investor all on your own. You want to make money, but where you put your money is if you put it into companies that are making a difference and making an impact and the way. And changing the world and the way you want to see it changed, then it's twofold. I really feel that most women, you know, when they invest, they want to see an impact as well as a return. And women, I say we've de risked as much as we can, but typically, you know, besides 35% higher returns and exiting faster, which means we get our returns and our exit our money back faster. And women create great business cultures. They're known to be relationship driven in sales. When times are tough like the pandemic, they can make money, they watch cash flow, they can make our investment dollars last longer. That is one of the main reasons I think that this is. We've kind of de risked. You know, you can't de risk at all, as you said. But yeah, we've done our best and we all want to make money. I want to make money on my investment, and I invested in our fund too.

Incredible. And I'm glad that we were able to touch on this too, because one of the things that gives and takes their blessings and curses is the reality of passion in business. If you're passionate about your business and you're passionate about the impact that you want to create, that can be really good because it allows you to tap into almost an infinite wealth of energy for when times get tough. And that's often the fuel for the resilience we need to be successful. And then it can also make us more persuasive. Because if you think about the. The Greek approach to persuasion, if we go back to Aristotle, here we have logos, ethos and pathos, so logic, ethics, and then also passion, we recognize that can be persuasive. But sometimes if we have too much of that passion, then it makes it difficult for us to connect with other people. And sometimes the more passionate we are, the more uncomfortable we feel talking to the practical side of what it is that we can deliver. So you find people who might be very. They have a business based on the environment, for example, they care about the environment and they lead really heavily with that. But they're trying to pitch to investors who care more about money than the environment. And so you miss the mark. So I think what I want to make sure that the listeners are understanding is that you're very intentional about the way that you're persuading. You have to understand your audience and then craft a message that actually resonates with them.

Absolutely, yeah. And finding the right founders that have that equal balance of passion and logic is also very important. When we do our due diligence to looking for the right companies to invest in. We put a lot of trust in the right founder. More, sometimes not instead of the business model, but it's probably more important than the business model. Like if that founder and the founders, the co founders. Because we only require Women to own 30% of the company, we want them to have diverse teams because we want the right people in the right seats in their company. And we, and one person cannot make a company successful. So that's really, our approach is, is. Is to really make sure we got the right founders before we invest.

Oh, that makes a lot of sense. A lot of sense. And Cindy, one of the things that we talked about too is how challenging it can be to get investors interested in making these investments. Not just in your fund, but in general. It's very competitive and you might perhaps find yourself in a situation where other people are trying to get the same investors to invest in different things. So I want to touch base with you on your relationship building strategy. So when you are trying to let people know about the opportunities that you have available and you start to create those relationships, what does that process typically look like for you?

Well, first of all, angel investing is not for everyone. But I really look for like minded people that understand. My first check was from a man. This is not a women's angel investment group. To people that are like minded and see a missed opportunity of that venture capital is missing. On focusing on women. There's a lot of reasons women are not maybe getting their companies to the scale that is attractive. Not enough women in that pool, you know. So I feel like that's one of our roles. But you know, like minded investors come in an investor but also see how what the opportunity is to invest in women that they're creating great companies. I do a lot of coffees if you want to get tactical about it. I do a lot of coffees, a lot of lunches and a lot of, you know, hosting, you know, happy hours and breakfast to introduce angel investing to as many people as I can. Because central Ohio is becoming a very great good startup hub. The universities and all the incubators, you know, the, all the different startup business sources, you know, and Labs and Rev1's. One of them in Ohio State is a great source for commercialization of technology and software and bio and life sciences. So, you know, I just feel like building this angel community that just happens to focus on females because I feel like it's A better risk and a needed opportunity for women. That's how I build the relationship. It's like minded. It's not for everybody, but you know, there's enough people out there that see the value of that and they can invest in other things. I mean, I'm invested in multiple things. It's not the only thing I do. I don't just invest in women owned companies and just invest as an angel investor. I invest all along the line as much as I can and I can afford to do. I try to diversify stuff. So this is just another way to diversify your portfolio, really.

Agreed. And I love the fact that you focused on like minded investors too. What I'm assuming this means is that you are finding people who resonate with the mission and resonate with the opportunity. And so it's almost like a bit of a vibe check. Is this something that you're interested in? And if there is the interest, you can feel that warmth, then we can kind of proceed. And it sounds like the opposite side of this approach would be recognizing, hey, if somebody doesn't really get it initially, they might not be that like minded investor that I'm looking for. So we might say, all right, I understand this might not be for you and move on. Rather than focusing on trying to persuade them to see things your way, you're recognizing there might be a little bit less friction and more opportunity to just do a quick vibe check and then keep on trying to get a greater number of these investors lined up for potential meetings to see once a quarter.

I do an Angel Investing 101 and I try to invite people into my workshop. Sometimes it's online, sometimes it's in person just to introduce it because one of my. Besides what the important job of investing in female entrepreneurs and making sure that women have more access to capital and those opportunities. The other side of it is educating investors to see the opportunity to diversify their portfolio. A diversified portfolio. Alternative assets can be wine collections, art collections. This is just as risky as having, you know, investing in Bitcoin and NFTs. You know, it's just this is just another one of those alternative assets that if it's the right one for you, then you know, just if you don't like wine, you're not going to collect wine, right? If you like business and you like supporting entrepreneur and innovation and investing in impactful companies, then this might be something for you. So I think activate, I say educate and activate is one of my missions as a founder of this organization. And I really want to Create this so that it's sustainable into the future. It's is a lasting organization that women can always have a place to come to for, to pitch for capital long term.

Absolutely. And you and Mary have done a great job of creating that platform not only for the women entrepreneurs looking for the opportunities, but those investors who are looking for that connection. And there has to be a lot of trust between you and the investors in order for them to feel comfortable making the investment. And so when you're having these networking meetings, how do you navigate the conversation in a way that builds trust in both you and Mary as the leaders of the organization, but also the actual investment opportunities with the founders?

Well, one of the things I think women do well is they are great collaborators. And so when I designed this, Mary and I designed this, we decided instead of using a lot of angel groups that we interviewed, had trouble getting investors to volunteer to do due diligence and do some of the work behind the scenes, to dig deep into the companies and because it takes some time. And the statistics show that the longer you do due diligence, the more time you put into it, the more you dep in depth, you dig into their businesses to look at the red flags and green flags of an investment, the better your it probably will perform for you, your portfolio overall. So I kind of handpicked about 15 or up to 15 advisors. And those advisors are on my advisory committee. They are on our investment committee. And they have diverse industry experience. So when you're talking, when I introduce people to angel investing, it's not come invest. I know everything. I know every industry. It's not about me and all my knowledge. It's our collective knowledge and our collective experiences and our collective knowledge of the different industries within the different industries is what makes Accelerating Angels a strong organization. Excellent. Coming together in that collaborative way to make. Tap into everybody's expertise to make the very best investment decisions. And I think that is going to make us. That's de risking it a little bit. Every teeny step I take, I try to find a way to de risk our angel investing. And I think that's one of the big ones that has really been beneficial for us to making investment decisions. So I guess I tell people what we're doing and they believe in what we're doing. And trust is something that you just. I mean, it doesn't happen overnight. But I think between my experience, Mary's experience, the experts that we've brought together to help us be successful, I think that must resound to some people because We've got over 22 investors in our fund so far and, and getting going to get to 50 here pretty soon.

So congratulations. Yeah, this is, it's significant. It is significant because you're creating these incredible opportunities. And like we said at the beginning, it's a win, win, win, which is one of those rarities, but it does it exist here. And you're creating this trust through transparency by being open about what your goals are, who your audience is, what the data is.

That's the only way I do it.

That's good, smart. It takes time, but I think a lot of times people overthink it and they also try to shortcut it as well. But like you said, if you keep on having these conversations, you give people the opportunity to engage in due diligence so they familiarize themselves with your fund and the entrepreneurs. Again, you're. You cannot perfectly de risk it, but you can make it feel less risky because of the reality of trust.

Well, and I think if investing is new or investing outside of your, what you know, your regular standard investment with your financial plan or whatever, if this is new to you, this is a safe place to do it. I think investing in a fund where, you know, you're pooling your money together and you're collectively making decisions on investments is a really good place to start. If you invest in one company, you have a 50, 50 chance of, of having that company give you back your money or more. We have diverse industries within a fund and our fund and diverse types of founders that are coming to us and with different experiences. And investing in 20 or more statistically says, you know, if you invest in 20, your portfolio is 20 or more, you're more likely to have a positive outcome than if you invested in only 10. That's why we have the 20 companies, $100,000 average check size, so that we can have that win, because we really want to have this first fund be successful so that we can, you know, raise a bigger fund and put $250,000 checks in the hands of women founders. So very motivated with this first fund, especially getting started and doing our best to use best practices and methods for de risking our investment. So I hope that's transparent enough to evoke some trust. Right?

Definitely. This makes me wonder too, Cindy, because I know the work that you all are doing is with the fund, but in your past life, you've had to. You've been the beneficiary of some investment along the way. And for some entrepreneurs, they might not have the opportunity to work with A fund like yours, or maybe because of different circumstances, it makes it more difficult for them to get the credit that they need to get the business launched. So if there's an entrepreneur who's out there who's saying, I need to do a friends and family round to get things started, and a lot of the people who are in their friends and family rounds are not savvy investors who have made a lot of investments and might have been their first one. How do they make that pitch to those friends and family members in a way that makes the friend or family member feel secure or safer in that decision?

Well, I think you have to present a really strong and honest not. You know, there's a lot of companies that come with the hockey stick. You know, they say, here's our sales, and then all of a sudden they're just going to bounce up there to millions and millions of dollars. So if you're going to do that, you have to know what those numbers mean. Right? And it has to be authentic. You have to be authentic, especially and honest with your family that this is risky. You know, my first checks may be my first check. Writers may not get their money back, but, you know, if you, you know, have a solid plan and you have the numbers that back it up, you have done your homework, so to speak, you ought to be able to evoke enough confidence to get friends and family to write. My father wrote my first check so for my publishing business. So, yes, it can be done. Takes up families, trust. Right. Then the next stage is, is even harder. You know, how do you get a complete stranger to believe in your. Which would be our angel investors. How do you get us to invest in you? Well, that's a little bit more challenging. Right. But then again, it's all about showing your product is a viable product. It's going to sell in the market. Somebody wants to buy it and needs it and wants to buy it and pay for it for the price that you're charging. That's proof of concept and that has to be done before anybody's going to buy in. So. And then trap with us. We'd like to see some revenue and traction because we're, you know, it's our first fund and we want to make sure that we have our processes down in this one and we're very successful. And so we can move on to the next one and maybe have some earlier stage companies and some companies that don't have FDA clearance yet that we can just take a chance on in a bigger portfolio. So, yeah, entrepreneurs just get out, get. Make sure you got everything lined up and you know your numbers and you know your potential for your products.

This is great, Cindy. And the thing that I like the most is going back to that transparency. We have to recognize that being transparent doesn't always mean that it's going to be unicorns and rainbows, because we have to be transparent not only of the potential upside, but also with the potential downside. And we're often so focused on getting to yes that we forget to recognize that as we are persuading and having these conversations, we need to make sure that we're giving people enough information to make the best decision for them, which might actually be a no. And if we are intentionally holding back some very important information that they need to make a good decision and they say yes to us because they didn't have that information, then that turns. That comes dangerously close to manipulation there too. So I really like the fact that you said, hey, as we're giving our family and our early stage investors information about the organization, we have to be honest about, yes, this is what we believe the upside could be. And we also recognize that it might not be that, but communicating that in a way that is honest and transparent, but not unnecessarily detrimental to our goal too.

The other thing is that entrepreneurs need to be careful who they're taking investment from. Not all invest investments are good investments really need to know who you're getting your money from, whether it's a good partner, because they're going to be with you for a long time until you exit. And so they call it smart money, right? You want people that are going to help you get there, open doors for you, help you succeed, and be good advisors and mentors, not just write you a check. Sometimes just writing a check comes with attachments that you don't want too much control, not a nice person, whatever it might be. Just, you know, make sure you like the people that you're taking the money from.

Cindy, this is a very important point. Very, very important point, because again, we can get as an entrepreneur and you, both of us have been in this stage entrepreneurship where we're like, I wonder how I'm going to eat today. You know, where it's. When it's the really a really tough point in our careers. And then we might say, all right, I don't have a lot of leverage now, but I need some more investment, I need some more money. And so that puts us in a position where we go into the negotiation feeling disempowered and Feeling as though we have to take whatever is given to us and we have to work with whoever is willing to give us money. But sometimes the worst thing that could happen is a deal that should have never been made with a partner you should never have gone into partnership with. So for those entrepreneurs who find themselves in a situation where they have a financial need and they are vetting investors, what are some things that they should look for as potential red flags? Saying hey, as I negotiate, this is a red flag that might tell me this is not the right deal for me.

Well, I know one entrepreneur that turned down a million dollars because the investor wanted too much control and wanted would have deluded the other investors and they turned it down. So it has to be the right deal at the right time and people you like. That's really all I can say about that. So I mean I've turned down investors. I mean not turn down. I have not pursued certain investors. And when I've gotten a bad feel for that this person may not the right person for a fund just because their attitude about the things I thought they could be troublemakers. And you don't want troublemakers. You want people you like and that aren't going to cause trouble. Like questioning every single thing that you do. Right. There's got to be some trust in there. And if someone doesn't feel as a feeling the trust, I'd rather them go invest somewhere else.

Right.

Rather than being second guessed all the time. You know, so it's in all life situations. Right. You want to work with the people that you like and you have a, you feel comfortable with.

Yeah. This is a great way to circle back to one of the things you said at the beginning. You are looking for like minded investors. And I know for me in my, in my personal life and sometimes in business, I have felt very confident in my negotiation skills, which is a good thing. But sometimes not that those negotiation skills may have led me in a wrong direction and put me in a position where I made a bad decision. Because in my mind I say, all right, cool. There might be a gap between where I am right now and where this person is. And I believe that I have the skills to bridge that gap. But could is different from should could you make this deal happen? Yeah, you could. You could make it happen. Should you? Probably not. If it's not the kind of like minded investor who is going to go along with you in that collaborative way moving in the same direction. So Cindy, I'm really glad that you, you pointed that out because not all Money is good money. So we need to make sure that we're not only negotiating to get better deals, but also making sure we're negotiating to get the right deal too.

Absolutely.

This is great. Cindy. I know time is running out for us on this interview, but before you go, I know there's some people out there who might be entrepreneurs who want to connect with you or might be potential investors who want to work with you as well. So for people who want to get in touch and learn more about your work, what's the best way to get in touch?

Well, our website is acceleratingangels.com and there's a link there for entrepreneurs and investors so you can learn more about us. Not only do we have an opportunity for accredited investors, but non accredited investors. We also have a membership level for both accredited and non accredited investors that don't want to invest in the fund but would like to come in and learn and join our group. So there's opportunity for and those non accredited investors can be founders if they want to come in and kind of pick the brain of investors and kind of join us on a due diligence team and see what we look for. I mean we feel like the founders that we help, whether they're members or we invest in them, that they're going to be our future angel investors and they're going to pay it forward and invest in the next group of women led companies that are coming through. So that's kind of completes our mission. Full circle.

Incredible. Cindy, thank you so much for joining us today. Really appreciate it.

You're welcome.

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