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Welcome to this masterclass edition of Negotiate Anything.
With over 1700 episodes featuring some of the world's brightest minds, we've carefully curated a couple of powerful conversations for you.
What makes this so special is that you'll hear how different experts from different industries approach the same challenge in their own unique ways.
Our goal is to give you multiple perspectives so you can build your own unique style.
Success doesn't look the same for everyone.
And in this masterclass, you'll see exactly why.
Let's dive in.
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 is Cindy Anglefield.
I'm a serial entrepreneur, angel investor, business coach, just really been focused on helping female entrepreneurs, but 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 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, 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 100000 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 a nice white space where, if women aren't getting the venture capital dollars, then it's an opportunity for us to get in on an early stage investment and help these women to hit their milestones and get traction and scale their businesses so that 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 in.
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 where actually the Credit Opportunity Act was enacted so that we did not have to have a male co-signer for our loan.
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 and 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.
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 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 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 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, despite all of the biases and the lack of opportunities for women, they actually outperform male-owned companies by giving their investors 35 higher returns and they exit faster.
So as far as investing, they're definitely going to give 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 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 and orders 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 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're 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 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, 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 the caliber of companies that are coming 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 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, 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, brings it down into beads, makes the beads into thread, the thread into fabric and the fabric into clothing.
I mean women business owners.
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 for this, because 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 five percent of that and put it into impactful women owned companies or early stage companies that are innovative and they're making changes.
They're 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 200000 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.
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.
Okay, Cindy, so you just dropped a lot on us here.
It's like I'm a kid in a candy store.
I'm not even sure where to start, because one of the things that we talked about is the fact that you have de-risked this investment opportunity as much as we can.
We understand there's going to be risk involved in any investment, but just given the track record of success for women entrepreneurs in general, but also the people that you've worked with, you've done your best to de-risk it.
And one of the things that I find really interesting about this approach to persuading the investors, because it sounds like you are leading with the what's in it for you type of considerations.
You're making a business case for this investment rather than coming at it through a lens of equity or a lens of altruism or something like that.
What is it that led you to take the strategic approach, to focus more on the money than perhaps some of the other social concerns that are valid but might not be as persuasive?
Well, I mean, you make an investment to make money, right?
You want to 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 changing the world in 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.
Women create great business cultures.
They're known to be relationship driven in sales.
When times are tough, 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.
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 old 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...
Our 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.
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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 first, 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 one person cannot make a company successful.
So that's Really, our approach 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 investment 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 sit 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.
So I feel like that's one of our roles.
But like-minded investors come and invest but also see how 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, all the different startup businesses.
Sources that you know.
Labs and Rev One'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 investing in Bitcoin and NFTs.
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.
It's 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 in-depth you dig into their businesses to look at the red flags and green flags of an investment, the better 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, 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.
It's coming together in that collaborative way to 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 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 I'm going to get to 50 here pretty soon.
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 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 knew 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 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 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'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 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 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, 100000 average check size, so that we can have that win, because we really want to have the this first fund be successful, so that we can raise a bigger fund and put 250000 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 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've 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 just 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.
You have to be authentic especially, and honest with your family that this is risky.
You know, my first checks, maybe 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 for my publishing business.
So yes, it can be done.
It takes up family's trust, right?
Then the next stage is even harder.
How do you get a complete stranger to believe in you, 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.
And then with us, we'd like to see some revenue and traction because 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.
Yeah.
Entrepreneurs, just make sure you've 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 liked 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 you.
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 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.
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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 of entrepreneurship where we're like I wonder how I'm going to eat today.
You know, it's the really, 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's.
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 partnership.
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 would have diluted 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 turned 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 things, i thought they could be troublemakers.
And you don't want trouble.
You want people you like and that are 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, or isn't feeling, the trust, i'd rather them go invest somewhere else, right?
Rather than being second guest 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 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 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 do that.
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 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.
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 acceleratingangelscom 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.
Welcome.
That was the first part of today's masterclass.
Up.
Next we'll hear from another expert with a different approach, giving you even more strategies to add to your toolkit.
Let's keep it rolling.
Chris, thanks for joining us today.
Yeah, thanks for having me.
Excited to be here.
Yeah, I'm excited to return the favor.
So how would you get us started by telling us a little bit about yourself and what you do?
Yeah.
So I probably have one of those jack of all trades, master of none backgrounds where I've kind of been in investment banking.
I've been a founder twice, sold two companies, raised money at both of them.
I've been on the venture capital side.
Right now, I build products to help people invest to build their wealth at Wealthfront.
And I host a podcast that you graciously joined me on, called All the Hacks, where we explore how to upgrade life money travel, all while spending less and saving more.
I love it.
And listeners, make sure to check out that show.
It is phenomenal.
Incredibly successful in a short period of time.
So kudos to you, my friend.
Thank you.
So listeners, on this episode we're going to talk about the keys to negotiating in the investment world.
And I know some of you are saying, but I am not in the investment world in that way.
Listen, don't worry about it.
We are going to pull out some of those general principles that will apply in all types of situations.
And so Chris is the perfect person to talk about this, and so we're going to approach this kind of like from a narrative form.
And so you're, we're going to play the role of the entrepreneur who's trying to court investors and negotiate effectively, and chris is going to walk us through how they can do so and what strategies and tactics they can use along the way.
And so chris, let's say, if we are that entrepreneur and we want to get an investor, how does that process even begin?
Yeah,
And to your point about this being for anyone, it turns out that a big piece of raising capital for a company is just about storytelling and selling yourself.
So the lessons here apply to basically anything, whether you're looking for a new job, whether you're a manager trying to hire someone, it's really you know.
It all comes down to storytelling.
And, you know, just being a likable person is a really important part of that.
So know, i've started two companies where we've raised, i think in the first one, two or three million dollars and the second one ten million dollars.
The process always starts with deciding what kind of process you want.
Are you just looking for some friends and family that might write small checks?
Are you trying to seek out investors?
So, if you're seeking out real kind of venture capital or institutional investors uh, i think that you kind of think of the whole process as a race where you want to have everyone lined up so that you have a really, really exciting finish.
So if you were watching a horse race and there's one horse that's just clearly far and above going to win, that's great for the person to bet on that horse.
But there's not a lot going on.
There's just one thing happening, and that's all that anyone's watching.
You want to create a dynamic where people are excited by you and have so much fear that someone else might win this deal that they have to move fast.
Because in fundraising a fast moving deal is kind of the best.
Because people are willing to be more forgiving and negotiate in your favor, because they want to make sure they win.
That makes a lot of sense.
And so it sounds like we are kind of triggering a little bit of scarcity and competition through this process, right?
Yeah, I think every founder and entrepreneur that I've talked to that's had a successful fundraise.
And by the way, I've been on the other side of the table.
So as an investor, trying to get into deals that are hot is like the whole game, right?
If people will talk to within an investment firm, they'll say you know who else was up for winning this deal.
It's like almost like a badge of honor that you won the hot deal.
And so, Creating that hotness is so important.
And so I always say make a big list of everyone you want to talk to before you're even ready to fundraise.
Kind of like make sure you've built enough of a relationship that you could get an introduction.
You've got an email address.
And then try to kick everything off at the same time and block everything off.
Say, you know, this is my three weeks for this project.
I'm going to go all in so that I can get the most out of the experience.
What's really interesting about this is that yes, at the beginning you talked about the importance of storytelling and selling not just the business, but also yourself.
But we've spent the majority of our time, the short time we've spent together here, focusing on creating this dynamic, this atmosphere of competition, of scarcity and fear of missing out.
And it's almost like the emotional contagion that can occur within a pool of investors is more persuasive than the nuances of the business itself.
Tell me if I'm hot or cold on that one.
Yeah, so at least in the early days, right when we first raised money at both the companies I was a co-founder at, we didn't have a product yet right.
So they were betting on the people.
So I always said, when I was talking to other investors, as an investor I said look, we were looking for a company that either had traction, we were looking for a team that we wildly believed in, we were looking for people that were really passionate for the product and we were looking for a big market opportunity.
And so some of those things aren't there.
Like you're great if you get two out of three or three out of three, but you're okay with one out of three.
And so, at the end of the day, there's very limited information because there's not a product yet, often in the early stages.
This all changes if you're five years into a company and you have metrics and you have revenue.
But in the early days, the signals are, how hot is this deal?
What does someone know that I don't know about the people, about the space, about the competition that could come up?
And so that's about creating this race dynamic.
And then there's the person.
Do I want to bet on this person?
And so I think the two things that you could do to be more successful is it all revolves around a pitch in this world which is you know, you have, and you, if you equate it to interviewing for a job, it all revolves around that interview.
How do you make the most out of the small period of time that you're in front of the person you're trying to negotiate with?
And then how do you make the most of the entire dynamic that will shape the process?
So I think you're warm in that it is really important to run an efficient process and create the kind of dynamics you need to be successful in your negotiation.
But it is also important when you're in the room to really wow someone.
And that's all about storytelling.
It's all about likability.
And, you know, obviously you need to have a good product, right?
You can't be selling.
If I go, have the most amazing job process and I have the most likable story but I'm applying to be a surgeon like I'm not getting that job.
I have no practical, you know, training to do that.
So, you know, you have to have a good, good product, which in many cases is yourself.
But the process is also so important.
Yeah, I think that's a really great point because again, we are the product in not just in the investing world, but also in general.
People are going to bet on us.
And so, when it comes to those key triggers that people are going to look for, when they say hey, you know Chris Hutchins, I'm going to bet on him.
All right.
So what do you think those key elements that people are looking for are in this part of the process?
I think it's about passion and likability and competence.
So what I was looking for... So starting a company is really hard, right?
Every day, it's another problem, another fire to fight, another issue.
And so it gets harder than it is when you first start.
There's nothing easier than the first day when you're like, all excited.
This is going to be amazing.
I haven't had to fight the fires.
And so investors are looking for entrepreneurs who are really passionate not just passionate today, but something about their personality, their experience, their history has made them passionate about this space, such that they are going to be able to fight through all the hard times.
So I always tell people look, if you aren't so excited about this company that you can convince someone that you are you were put on this earth to build this business then you're going to struggle because they're going to see right through that.
So if you say, look, I know that NFTs are really hot in the crypto world right now.
I'm going to start an NFT company.
But you can't convince someone that that's something that you stay up late researching and you spend time on the weekends doing.
They're going to see through the fact that you're just trying to capitalize on an opportunity.
And unless you have a resume that shows your consistent ability to do that, I as an investor was kind of very weary.
But if you're three people who've worked in education and technology and you found this opportunity to make the workplace or the educational space much more efficient.
A company I invested in called Clever was that team?
And I was like I don't know anything about educational software, but you guys are so fired up about this.
And you have an idea that best I can tell seems reasonable.
And you have the capabilities to build a company.
I was in.
I invested.
And I didn't know much about the space.
It wasn't about whether the software was good.
It was about that these three guys were so passionate about what they were doing that I knew that they could fight through any of the problems they faced.
Yep.
It makes sense because, as the owner of a company too, there are going to be those days where the only thing that gets you through is your passion drive, determination.
And you're not going to have that if you don't have a clear sense of purpose.
So it's important to convey that.
Now for people who are not high energy.
Right, because when we think about passion, we think about a lot of energy effervescent personalities, those type of things.
But not everybody has that personality type.
If you're somebody who is a little bit more low key, a little bit more reserved, how do you display that passion while still being authentic to who you are?
Yeah, I mean, I think there's various different ways to kind of, quote unquote, own the room.
And you can do that through competence, right?
You don't have to do that through energy.
You can come in and say...
Here's what I've learned about this space.
Here's why I'm so excited about this space.
You could do it in a calm, cool, collected manner that is not, you know, gregarious and outgoing.
And I've invested in those companies also.
There's lots of engineers who are not kind of own the room kind of people with their personality, but they are own the room with their ideas and their intellect and their ability to listen effectively.
We talked in my podcast about listening being a really important part of negotiating.
Understanding the questions people are asking and being able to answer them, I think, is a really, really important part of fundraising as a company and being able to sell yourself in general, showing people that you've thought through the things that they have questions about.
Because look, if you're starting this business and someone who's hearing about it for the first time has questions and you haven't thought about those questions, like that's concerning
So I spent so much time before pitching investors, going through every single question I thought they could answer.
And I actually went and made a deck like a PowerPoint style deck with Google Slides.
And I had a slide for every question anyone could ask.
And I actually like committed to memory what numbers they were.
So instead of being able to sell as a narrative the answer to a question you know and make it up on the fly, I was prepared.
So someone would say, you know, we raised money for a company in the financial advice space.
And they're like, how do financial advisors spend their time?
And instead of saying, well, you know, this is kind of how I just jumped to slide 73.
And I'm like, this is exactly how they spend their time now.
I've already thought about that question.
And kind of conveyed the fact that I'm prepared and you can be prepared without being having a boisterous personality.
And and you can convey passion by talking at length about things.
We probably all have a friend who's kind of super nerdy about something.
And maybe she, you know, isn't crazy excited every time, but she could just go deep for hours and you can convey that with any personality.
That's great.
I love that point.
One of the things that we talked about beforehand was the importance of negotiating the terms, negotiating the right terms, and also how timing plays into how and what you negotiate.
Can you tell the listeners about that too?
Yeah.
So, you know, first, I'll jump back quick to this race dynamic.
Whenever you're trying to get something done, it's let's have everyone at the same place.
So you don't want to be negotiating your terms with one investor while you're just meeting the other investor.
And so I would always try to run things where, you know, it's like three weeks.
The first week, it's an intro meeting.
The second week, it's a follow up meeting.
And the third week, we're going to kind of pitch the entire investing team.
Usually there's a partnership.
And if someone came in late to the process, I tried to say, look, we're already a step ahead.
So if we could try to get these first two meetings done this week, that would be great.
And if someone was pushing and said hey, let's have that second meeting tomorrow, I'd say actually, could we do that second meeting next week?
So once you've got everyone on this cadence, you got to figure out how the deal is going to get done.
How is the person on the other side of the table going to make a decision?
And in a lot of cases, this is true for hiring.
This is true for investing.
There's a team.
And so understanding whether the person you're talking to could even make the decision on their own.
And if not, what aspects of the decision get made by a committee or a group of people?
And so with investing, I learned that, you know, ultimately the partnership is going to have a conversation and decide whether this deal gets done.
But they're not going to decide on every single term.
They're going to leave the person, the point person up to some of it.
So I focused on let's make sure we're only talking about the things that are going to matter for that conversation.
So there are a handful of subtle, subtle decisions that don't matter.
And in investing, it might be how much equity is each individual person on the team going to get, or the exact dollar amount of people that you're going to raise money from?
Those things I punted and said, well, we can talk about those later.
Let's talk about what the value of my business is, how much you are going to be investing.
And let's let's get through that first.
It's interesting, Chris.
So it sounds like what we're doing is we're figuring out the most important things to address.
And we're addressing those things first and recognizing that some of the smaller details don't need to be addressed and fully articulated at this time.
Is that right?
Yeah, it's trying to exactly correct, right?
I bought a car once and I remember negotiating and the price of the car was something that the sales guy had to keep going back into the room in the back and come back with.
And then at the end, I said, oh...
OK, we got the price.
I'll do this if you throw in like the floor mats.
And he was like, sure, we'll do that.
So clearly he didn't need to go into that back room to talk about floor mats.
So it was a waste of time if I had brought them up earlier, because I don't need the guy in the back thinking that I'm just trying to get more and more from this deal.
So it's like, let's only talk about what needs to be discussed now.
And let's do that up until we've decided on those decisions.
And then we can talk about the next ones.
And you can kind of move through the process of negotiation which, at least when you're raising money for a company, can be very, very multi-step.
So who's going to be who else is investing?
You know, how how are we going to structure this round?
How are we going to announce it to the public and all those things?
But you don't need to figure it all out up front.
You need to figure out just what you need.
Yep.
And another thing that you mentioned was timing.
So recognizing that some things are easier to negotiate at different times in the process.
Can you give an example of what that would look like?
Yeah.
So I think at the beginning it's interesting when you're trying to raise money or interview for a job, or there's probably so many applications, right?
The first conversation is not about trying to get hired.
It's about trying to get to the second meeting.
It's not about trying to get someone to commit to investing in your company in the first meeting.
It's trying to get them to commit to introducing you to another partner.
So in the first meeting, I would sometimes only show... a teaser of the company.
I wouldn't go into all the details because I wanted to leave someone asking more and they'd say oh, can we dive into some of the metrics of how you think this business will work?
I say, that's a great topic.
I have some slides that let's bring that up if it makes sense to have another meeting.
So you could kind of delay some of these things for that next meeting.
So I was just trying to negotiate in the first meeting.
I was negotiating for a second meeting, not for an investment.
And when you get to the final meeting, now you're negotiating for an investment.
So now all the stakes are on the table and you're trying to get the deal closed.
But you're still not negotiating for all the terms.
You're trying to get people to say, I want to invest in this company.
And that's where some of the competitive dynamic comes in.
It was really important I think, at least in startup fundraising for people to get a sense that this was going to be a hot deal.
Because as an investor, you always want the option value.
If you have the ability to invest in this company now or in a year, I'd rather do it in a year.
I'll have more information.
So why would I do it now if I could do it in a year?
Well, one...
The company might run out of money.
But if that's the case, that's a bad situation.
I might not want to invest in that company.
But I want to do it now because I don't want someone else to do it.
If I'm hiring, I don't want someone else to hire this employee.
And so if they're passively looking, you might drag them along.
The moment they say, hey, I have another offer, you're scrambling.
So my goal was to make the timing work, get everyone who wasn't serious out of the process.
Because so many people are sitting around waiting just to see what happens.
So after two days I sent all the investors.
I met with an email that said hey, things are moving quickly.
If you're not interested, no worries.
If so, let's set up an X meeting.
And I made it seem which was, you know, it can be risky, but I made it seem like I didn't need them because, at the end of the day, if that email is all they needed to say no, they weren't interested anyways.
So you might think, oh, if I say that, they might walk away.
The reality is they were going to walk away anyways.
So accepting that the goal is to only have people in your sales funnel that are serious, because you can spend time with those people and determine whether you need to add more people.
So it's this constant, let's go pitch 10 people.
Let's quickly follow up to see if they're serious.
If they're not, now there's two people left.
Let's go pitch another 10 people.
Now we've got four really serious partners out of that.
Let's go do a follow on.
Make sure they're there.
Now try to get it.
My goal is to get the number down as much as possible.
Obviously I'd rather have 10 people interested, but I want to get all the no's out as fast as I can, so I'm not wasting time, because this can be a time suck right.
Any process.
We've all looked for jobs.
What a time suck.
Doing interviews, writing cover letters, sending out resumes.
It's like, how quickly can you figure out if this company is interested?
And if not, let's stop trying to scour LinkedIn for a friend, of a friend who can put in a good word, because the company is not even interested.
And so the faster you can figure that out, the better.
So you can focus on the people that are real opportunities.
Makes sense.
And and it will make logical sense to everybody listening.
At least it should now. whether or not it makes emotional sense is a different thing, right?
Because, especially if you're starting up a business and you want investors, you understand that in a lot of cases, the investment money is the lifeblood of the business.
If you don't get that investment money, you can't just go into the bank account, pull out 13 cents and hope for the best.
Probably won't work out that well.
Right.
And so you need the investment money.
But at the same time, you cannot seem needy in the process.
And so where do you get the confidence to to still be able to be willing to let people go?
And make it almost seem as though they're not as important as they really are.
To create that dynamic.
How do you convey that confidently without that emotional pressure coming and pulling you down?
I try to do it in writing because it would be really hard for me to look you in the eyes and be like I don't need your money.
But I could write that because it's not true.
I do need your money.
This business will not work if I don't have your money.
But in an email, it's really easy for me to write that and keep it really short.
I try to put myself in the mind of what would I be doing right now if someone told me if I had 10 investors.
Tell me, we want you to come in next week so that we can give you money.
Well, I would email all the other people and say, hey, things are moving so quickly.
If I had even more audacity, I would say, hey, we don't actually, we should just cancel these meetings.
We've got stuff moving so quickly.
I didn't have enough courage to write that email, but I did have enough courage to write the email that said look, things are moving really quickly.
If you're not interested, that's fine.
You know, like we have other options.
I don't know where it comes from other than having been on the other side of the table and just understanding how the decisions are getting made right.
It would be interesting if you were looking for a job and a career in a space.
Go talk to the hiring manager at four companies that you don't care about and understand how they make decisions.
And uh, i i can assure you, having been on the other side of the table, that when candidates are email you and say hey, i have another offer, Could we move this interview up?
People are like, oh my gosh, someone wants to hire this person.
They must be amazing.
We've got to move this up.
People trust other people's input, even if they don't know them.
So, you know, when you go to here's a great example.
If you've ever been to like a grocery store and you looked and there's like seven salsas.
But this one salsa seems to have two two jars left and all the other ones are fully stocked.
People must really like this one.
I'm going to get that one.
It's like you walk by restaurants.
You want to go to the restaurant that other people are eating at.
You walk in the door and there's one person in the whole restaurant.
You're like, I think this is a mistake.
We shouldn't eat here.
And so that scarcity mindset of if other people want this, it must be good.
You need to create that in other people's minds when you're trying to negotiate with them for anything.
Make them think that you have options because that's how it works, right?
You're negotiating leverages that you have a better option.
You can create a...
Allusions may be the wrong word, because because hopefully it's like somewhat true, but you can create the sense that there are more options and make it clear that, even if they're not done right,
If I had another investor saying here is an investment, I would have said hey, things are moving quickly.
We have a term sheet from another investor.
So totally fine to turn this off.
But that community is small enough that the last thing you want is for someone to find out that you were lying.
And so I'm sure there are investors out there who do this, right?
There are movies that get made about entrepreneurs that take bold moves.
I never felt like it was worth taking that risk.
But I was like, how do I write something that is as close to that as possible that is not a lie?
So, you know, we have I would say we're starting to meet with partnership.
We're taking partnership meetings next week.
So if you're interested, we need to move quickly.
If not, it's fine.
That was true.
We were taking meetings with partners, but I didn't say we have three term sheets.
Right.
I didn't say we're at that stage.
I could say we're expecting to have some term sheets next week.
Like we're at the point that investors are offering us term sheets, but I didn't get that far.
Yeah.
Oh, man, Chris, this is great.
This is really helpful.
And for the people out here who are negotiating, let's say whether it's in the fundraising kind of space or just in general, when it comes down to all of the wisdom that you've gleaned as you've collected all of the hacks, shout out to your podcast All of the Hacks.
As you've collected all of these great negotiation hacks, what would you say, is the one thing that is the most important thing that people do when they're negotiating effectively.
Well, this feels like a trick question, because I feel like I asked you this question and you told me I have to listen more.
And so now I feel like how could I answer it without that?
But assuming you've been listening to this podcast and you've learned to negotiate anything for dozens of episodes, you already know you should be listening.
So I would say the most important thing for people to take away when it comes to negotiating, from my perspective, is to understand the process that's happening and try to play to that process.
So if you know that people are trying to get things done quickly and don't want to miss out, well then try to get as many options on the table as possible in as short a period of time so that you can play to that dynamic.
If you're working with a company that you know really wants to take their time, That won't work.
But if you figure out how the game is played when it comes to deals getting done and in fundraising, the game is not losing.
There are investors out there who have a mandate internally at their firms to say only invest in companies that have another term sheet on the table.
Like, great, you don't even have to do diligence.
It's like if one of these seven investors is willing to invest, we'll do the deal.
And so your job is actually just getting the founder to say yes versus.
There are other funds that are like we only invest if we're the first check.
So you got to figure out who you're trying to get, you know, to say yes and play that game.
Don't play the game that you think will work.
Play the game after you do the research that you know will work.
Thank you so much for joining us, my friend.
Really appreciate it.
And before you go, can you let the listeners know how they can get in touch with you and how they can learn more about what it is that you do?
Yeah.
I mean, if you're listening to this podcast, you're already in a podcast app, so you can just search for all the hacks.
That's our show.
Or if you're online, it's allthehacks.com.
There's tons of episodes on everything from negotiating, which you guys know, but also travel hacks and getting a deal on a car productivity, family side hustles, all kinds of good stuff, investing and more.
So check it out.
And if you want to reach out to me and let me know what you think, definitely.
I'm at Hutchins on Twitter.
Chris at allthehacks.com.
Would love to hear from you.
Awesome.
Thanks Chris.
Really appreciate it.
Yeah.
Thanks for having me.
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