Carol Fishman Cohen: [00:00:00] Welcome to 3,2,1 iRelaunch, the podcast where we discuss strategies, advice, and success stories about returning to work after a career break. I'm Carol Fishman Cohen, CEO, and co-founder of iRelaunch and your host today. We welcome Nicole Cuellar-Lopez. Nicole is an angel investor with Pipeline Angel and is Peloton Interactive's Senior Manager for Diversity, Equity and Inclusion.

She invests in early stage startups, which have a positive social impact and are led by women and femmes. An Uber alum, where she started in the early years, 2013, and worked there until 2019, Nicole held roles in writer marketing, operations and logistics and DNI. Prior to that, she worked at an international education nonprofit. Nicole is going to help us demystify angel investing and also give advice to those of us relaunching at startups, on how to evaluate a job offer when equity is on the table. We'll also talk about the role of sponsorship in all of this. Nicole, welcome to 3,2,1 iRelaunch.

Nicole Cuellar-Lopez: [00:01:19] Thanks so much for having me, Carol, pleasure to be here.

Carol Fishman Cohen: [00:01:22] Well, I'm really excited about this conversation. We've never talked about angel investing on our podcast before. So before we get into all those details, can you please walk us through your career path so far and how you became an angel investor?

Nicole Cuellar-Lopez: [00:01:39] Sure, absolutely. So I got involved in tech. And as you mentioned in the introduction, around 2013, and I was coming from a career that had started in the nonprofit world.

So everything was really new to me as far as investing, startups, how they're funded, what it means to own a little bit of them and who gets involved in that process. My parents work as nurses, so I didn't really have anyone in my family or close friend group who was in finance or could really have led me there.

And the aha moment for me came when I was at an event for work and we had present some of Uber's angel investors. And in talking with them, it became really clear to me that these are just regular folks. They didn't necessarily have, there's no degree, right, in angel investing per se, they came from different career paths and just happened to have made the savvy decision to put a little bit of an investment into an early stage company.

And it really, really paid off. So it got my mind thinking. And as I work in diversity, equity and inclusion, I did notice that the folks I was talking to, they were a hundred percent male, happened to be a certain age group, a certain background. And I said, wow. I really think that there's a need for people from other backgrounds to be involved in this kind of investing.

Why not me? So I started to Google around to speak with some friends and one of my friends mentioned Pipeline Angels. She said, this is this group of women who invest in startups together and they learn through doing, so there's a little bit of a seminar first, and then you make your first angel investment together investing in women and femme owned companies. And I was able to do this only after Uber went public and I had the money available to me to do so. But that's where I made my first angel investment with a group of people in a similar situation.

Carol Fishman Cohen: [00:03:43] That's excellent. Thank you for that background.

And I'm remembering, I would like to mention that Natalia Oberti Noguera, who is the founder of Pipeline Angels, is on the advisory board of iRelaunch. So I just wanted to make sure that people were aware of that connection too. Nicole, can you define for us what angel investing is? There's going to be some people listening who don't know about the term or if they've heard it, they don't really know what it means.

Nicole Cuellar-Lopez: [00:04:12] Yeah, absolutely. So when a company is really young and looking to fund itself, there are a couple of different ways. A company might be “bootstrapped,” which means that the founder is using whatever they have available to put money into their business. They might go a more traditional route of going to banks and using business loans, or different credit angles, or they might seek investors. And there are really two kinds of investors. There are venture capital investors and they're angel investors. Venture capital investors raise money from institutions, wealthy individuals, and those investors make decisions to invest on behalf of their funders called limited partners or LPs.

Angel investing is when an individual is using their own money to invest in a startup and there aren't any other parties involved really besides the investor themselves and the starter.

Carol Fishman Cohen: [00:05:09] Hmm. Excellent explanation. Very clear. One follow-up question I have on that though, is in terms of the size of the investment.

Is there a line between angel investing, being the early, early stage and then venture capitalists taking over at a later stage, or does it have to do with the amount of dollars involved? What's the difference? I mean, sorry, what's the difference beyond what you already explained about VCs representing other investors versus angels representing themselves?

Nicole Cuellar-Lopez: [00:05:43] It often is the case that venture investors or venture investments come on at a later stage in the company's life cycle. And that those investments tend to be larger than what angels make. However, there's a really large range of the amount of money that angel investors put into a company. At Pipeline Angels, our typical individual check is $5,000 per person.

But we invest as a group. So if there are 10 of us making an investment together, that's $50,000 for an early stage founder, which can be really meaningful. So some angels invest as little as $5,000 at a time and some invest $100,000 and beyond, it really just depends on the individuals', the depth of their pockets, I guess you could say, and their comfort level.

Carol Fishman Cohen: [00:06:30] And when you're saying you invest as a group, so companies pitch before your group and everyone is sitting around the table, maybe the virtual table, but they're sitting around a table. And then you get together as a group and go back and forth, then discuss whether or not, and then vote whether you're going to invest or not, what is that like?

Nicole Cuellar-Lopez: [00:06:57] Yeah. And you know, the most accessible, I think, comparison is the TV show Shark Tank, where you've got three or four individuals sitting in a room and an entrepreneur is pitching their company. At Pipeline Angels we do a lot of work to think about what about that model we might like to change. So for instance, we talk about the role of unconscious bias in investment decisions. And we do an unconscious bias training before we evaluate startups to make sure we're asking ourselves some tough questions. Am I attracted to this company because the founder is like me in one way or another? Are there any other biases that maybe are at play while I'm making this decision? So that's an important part of how we think about making angel investments. The format of it is similar to what you say. We've been meeting for a few days to think about what matters to us as far as what we're looking for in investment.

And, then Natalia Oberti Noguera puts together this really wonderful slate of entrepreneurs who make five or ten minute pitches to the group. And we'll see about ten of them over the course of a day, and then huddle up as a group and say, " I wrote down that I really liked this one," and someone else will say, "I really liked that one."

And we'll say, "What did you like? What were any challenges or drawbacks do you see?" And we talk it out and we see which founders, which companies are emerging as the ones who we are most interested investing in. And if everyone is in agreement, then we maybe interview the founder one more time and then move to a "due diligence phase" where we look under the hood of the company. What are their marketing plans? What are their financial metrics, and background in place before making a final decision. And typically that process takes three to four weeks.

Carol Fishman Cohen: [00:08:53] And then the company goes about their strategy and you are silent partners or do you go on the board or do you have some sort of voice in what they're doing, and what is the timeline in which you're connected with the company on the investment side?

Nicole Cuellar-Lopez: [00:09:17] So we, when we invest as a group, we select one person among us to be the point of contact for the founder. And that person might have an observer seat on the board. They might join their board, or they might just be the point of contact for that company. It really depends. It's a negotiation between what the company is looking for and what we can offer.

So if there's great alignment in, "Oh, my professional background happens to be something that I can offer a lot of insight to the founder. I want to lead this investment and I want to be in contact with the founder on behalf of the investing group". I might be that person and I might stay in touch, pretty close touch with the founder.

We try really hard to be founder friendly, which means not getting in the founder's way, giving them what they need, if they need help with recruiting or introductions, those are different ways that we can be helpful as investors. And we try to be in it for as long as the company needs that support.

So investors may or may not have contractual terms that allow them to invest in a later round, and those are known as pro-rata rights. We try to make an investment and in our contracts say, yes, we want pro-rata rights so that we can grow along with the company as it grows. So, we might be investing at the earliest stage, but if the company is doing well and gets to raise a seed round or a Series A or B, which is what you call these later rounds, we want to have the ability to invest in that round.

So you always want to save a little money for follow on rounds if you're investing in an early stage startup.

Carol Fishman Cohen: [00:10:54] I see. And one more follow-up question on this. When you're making the decision to let's say, go ahead with an investment, the Pipeline Angels group, how do you figure out what percentage of equity that your investment is going to represent in the company? Is that a negotiation? Is it some sort of a formula that you use with what's the thought process there?

Nicole Cuellar-Lopez: [00:11:21] Yeah. You could talk all day, I think, about how to evaluate the valuation of an early stage company. Our mission at Pipeline Angels is to change the face of angel investing for women and femmes.

And that usually means that in the big picture of how companies get funded women and femmes entrepreneurs get less than 2% of capital. So we make a really concerted effort to fund these companies at the very earliest stages. And, if you've ever launched a business of your own or worked for a startup, you might be familiar with, it's really hard to tell what a company might be worth. So a founder will come to us and say, "Hey, I think my business is worth a million dollars, and if you're going to give me X amount of money that translates to Y percent of the company, and I'll give you that amount of shares." We try not to get too hung up on valuations when the company might only be months old or a couple of years old and not have a really big track record or a lot of data around it.

But yeah, it definitely is a negotiation between the investors and the company itself.

Carol Fishman Cohen: Thank you for that very clear explanation. Can you talk a little bit now about how you become even eligible to be part of an angel group or an angel investor on your own? I know there's this concept of being an accredited investor, and can you help us understand what that means?

Nicole Cuellar-Lopez:[00:12:59] So in order to invest in startups, you must be an accredited investor. And the definition in the United States of being an accredited investor means one must have a net worth of at least $1 million, or have an income of at least $200,000 for the last two years, or if you're married, $300,000.

And the spirit of this financial regulation is really that angel investments, investing in startups, is a really risky endeavor. And if you don't necessarily have the financial means to weather a loss, the spirit of requiring an accreditation for investing in startups, is that these are really high risk investments and the supposition is that if you do have a high net worth, you might be able to sustain whether the company goes bankrupt or, there is a loss of those funds.

But, there are ways to invest in startups if you don't meet those requirements. Today, there are crowdfunding platforms like Republic, Startup Engine and others,similar to a Kickstarter model, where a founder can make a website saying, "This is my company, I'm raising money." And you can put in really as much as you want, sometimes $50, $100 dollars. And in exchange for a little part of a company and participate that way. So there are really two different avenues for investing in startups. If you're accredited, you'll want to go the traditional route. But if you're not accredited, there are definitely opportunities now.

Carol Fishman Cohen: [00:14:34] Got it. And is there a scenario where you start out as an accredited investor and then some financial situation hits you and your net worth is less than it was, or you lose your job and then you lose your accreditation or is it only at the moment of investment?

Nicole Cuellar-Lopez: [00:14:54] At the moment of an investment, you should be an accredited investor and it's incumbent upon the startup to confirm your status. Now, if you want to continue to make angel investments over the years, and it so happens that you drop below the minimum requirements, then, according to regulations, you should not be making investments at that time in startups through angel investment, but there isn't really a governing body.

It's a little bit of an honor system. And really up to, it's at the risk of the founder, I think for them to run afoul of SEC regulations or other things for them to vet their investors.

Carol Fishman Cohen: [00:15:38] Got it. Let's talk a little bit about Pipeline Angels. Like you said, you did some research and met Natalia, and you got introduced to Pipeline, but how do people become members? Do you have to apply and be accepted?

And do you have to agree to devote a certain amount of time or be present for a certain amount of investment pitches? How does that part work?

Nicole Cuellar-Lopez: [00:16:06] Yeah. So Pipeline Angels is a group that you apply to and you fill out an online form and then have an interview with the team before coming on board. But in every city and now virtually anywhere there are operating angel groups.

So some people's university might have an angel club. I live in New York city. There's a New York city angels group. There are meetups for angels. If you do a little bit of research into what's available in your area or within your social network you might find different groups, but for Pipeline Angels, it's an application, it's an interview, and then committing to go through the seminar on how to invest, and then actually making the investment.

And then once you're in the group, there's deal flow that comes through that. So every couple of weeks we might get an email or we might get together on a zoom call and hear about the latest opportunities to invest.

Carol Fishman Cohen: [00:17:02] And that was my next question. You come into this, not really knowing how to be an angel investor. And you said there is some sort of training. And is that how you learned to evaluate the companies, or is it part the training and part sitting around the table with the people who have been part of Pipeline longer?

How did you get to the point where you felt like you really knew how to evaluate a company as an angel investor?

Nicole Cuellar-Lopez: [00:17:34] I don't know, Carol, I think there's a big element of beginner's mindset. It's really necessary to be good at this. I think you've got to be open-minded to different opportunities and along the way, you gain confidence one step at a time. I really love hearing from experts and by experts, I just think people with experience. So during the seminar, Natalia set up these wonderful panels and round tables with folks who've been doing this for decades. The Kaufman Center has a lot of different data on the basics of angel investing.

There's a lot to learn about, what is the average size? How long does a company typically stay in business? What is the likelihood of success? How do I evaluate the valuation? And you can go through those exercises with the advice of folks who've done it before, but at the same time, Most startups actually fail.

And if there's an investor who says to you, "I know what I'm doing, I trust my gut, I always bet on the winning horse," I would be a little bit skeptical. This is just as much an art as it is a science, I would say. And I gained confidence by not doing it alone. And by listening to folks, who've done it before, but at the same time keeping true to what I want to do, which is to provide early stage capital to women and femmes who have typically been shut out of these opportunities.

Carol Fishman Cohen: [00:19:05] And this is making me think about the reality of angel investing and the mindset that you have to have where you think that, you know what, as you're saying, most of these startups fail. So you have to have the stomach for investing over and over again for companies that might not succeed in the hopes that there's going to be one or two, a handful that do. I've heard about venture capital firms with that kind of philosophy. So how do you weather that personally?

Nicole Cuellar-Lopez: [00:19:42] If you listen to a financial advisor, they'll typically tell you that you've got certain priorities, right? To pay down your debt, any high interest loans you have, to make sure you have an emergency fund, to make sure if you're home ownership is important that you do that, and any other savings goals are prioritized. For me any money that I have to dedicate to angel investing comes after all of those priorities are met. So let's say I have a $100,000 hypothetically that I think that I can put towards angel investing. That's what I can afford to do after my needs are met.

So then I'll boil down and say, "Hey, $100,000 at that rate, I could do ten investments of $10,000 each or twenty at $5,000 each. You can't just do one or two angel investments and hope that it's going to pay off. You really need ten or twenty investments because most of them are going to fail, one or two of them might provide a 10X or more return.

So it is a little bit of a numbers game and you have to at the outset do a little bit of that arithmetic to make sure you have a strategy that works for you.

Carol Fishman Cohen: [00:20:56] And just to clarify for our listeners who might be less familiar with this when Nicole is saying 10X, that means ten times, the return is ten times what your original investment is. I just want to clarify that. Can you give us an example of a company that you have evaluated and invested in, or as, I know all of this is private, but is there anything in the public domain that you can tell us about?

Nicole Cuellar-Lopez: [00:21:21] I love to share about the companies that I've invested in. The very first one that I did was one that I love to talk about, and the company's called Time Study LLC, and the entrepreneur's name is Kesha Rogers, and she's a computer scientist, a programmer with decades of experience who was building software solutions for healthcare systems.

And her clients started to say to her, "We really need a software solution to help our time management and time sheets. We're spending a lot of time in our hospitals with physicians categorizing their time." So Kesha came up with a solution for her clients that helped to automate timesheets for healthcare systems.

And at the time this founder had bootstrapped the company and already had paying clients. And there were a lot of good green, I'll say green flags, for me. And I really loved that she represented everything that Pipeline Angels was about. It reflected my own values of diversity, equity and inclusion, and supporting this founder was, as a bit of a no-brainer to me.

And then when we went through the due diligence, it was really clear that she had created this company with a strategy in mind and putting the foundations in place, building a team and building a set of advisors around her that would help her grow. And at the same time she was getting accepted into different accelerators and incubators that represent groups of... if you're not familiar with an accelerator or an incubator, it's kind of a place where let's say Barclays Capital or HearstLab, these different institutions say, "We really want to support entrepreneurs and give them the advice and introductions and just to help support them to take their business to the next level."

So it was a good indicator that these accelerators wanted to support Time Study and I was happy to make that one of my first investments.

Carol Fishman Cohen: [00:23:25] Oh, that's pretty good to have that be one of your first investments. I might have to say, I love this concept of looking for green flags as much as you're looking for red flags.

So that's, I've never heard that before. That's great.

Nicole Cuellar-Lopez: [00:23:39] I think it's really important. I think you can talk yourself out of anything and doing something new is scary. So as we're sitting around the table, "but what about this, but what about that?" Yes. But we've needed to remind ourselves that we're going to take our risk and we're going to put our money where our mouth is. And put it on the line to support. So looking for reasons to do that is important.

Carol Fishman Cohen: [00:24:00] So let's switch gears now and talk about the individual who is joining a startup, who is presented with some sort of compensation package that includes equity or options to get equity. Because some of our relaunchers are going to be in this position as opposed to being able to be an angel investor in a company like that. So can you give some advice in terms of, how do you evaluate the equity part of an offer when you're joining a startup?

Nicole Cuellar-Lopez: [00:24:33] Yes. I had a conversation the other day with a friend of mine who said," I've worked for these big companies and everywhere I've worked, they've had these employee stock purchase programs where I've been able to purchase stock at a certain price, but never have I had the opportunity when I was joining a company to be granted stock." And that was a real aha moment for her when she learned that. And for me, I didn't know until I had really pursued my first opportunity at Uber. And if we have time for a quick story, I can share this learning moment for me.

And that was, here I was joining this company. I was in my mid-twenties. It was my first time evaluating an offer like this. And in the negotiations, they said to me, this is the cash salary amount and this is the number of shares in the company you'll get. And, here I am weighing this amount.

I'm thinking and I'm comparing it to my previous job and the salary amount I was getting. It was a total black hole to me, like what these shares were potentially worth. If I had to do it again, I would've asked a lot more questions. Like, what is the current value per share? What is the current valuation of the company?

Can you tell me if this represents X percent of the company at this time? But, in my mind at that moment, what was important to me was, can I pay my mortgage? Can I pay my credit card? I think I'm going to need more cash. And I actually negotiated my offer and took a little bit less equity for a little bit more cash.

In hindsight, right? Hindsight is 20/20. I never would have done that, knowing what Uber would become. Fortunately it wasn't too big a deal in the long run, but I wish I had a little bit more of a long view in, "Hey, if I really believe this company is going places I want to negotiate and ask is there an opportunity for me to take more equity with this offer?" Maybe I'd even be willing to do a little bit less on the cash side, if you really believe in the company. Now, depending on where you sit and how much information you have you really want to be careful because you don't know, right? Most startups do fail, but at the stage that they're able to hire and might be hiring multiple positions at a time. Maybe the company has just raised around and that allows them to do a lot of hiring. Those are good indicators that a company is on the up and up.

Carol Fishman Cohen: [00:27:03] That's excellent advice. And I'm trying to put myself in your position. You're early in your career, you're presented with this combination of equity and cash at a company where you don't know what's going to happen with it. And it's so hard to evaluate. Yes. Surely, in hindsight you could look at it, but I feel like I would have done the same thing.

I would have thought, I have to have a minimum amount of cash to pay my bills and that would have been a priority early on.

Nicole Cuellar-Lopez: [00:27:34] That's right. I think it was the right decision at the time. If I were making it today, I would do something different.

Carol Fishman Cohen: [00:27:39] Well, thank you for those lessons learned from your own experience, passing them on to our relaunchers who might be encountering this situation for the first time and laying out those questions that are really important to think about and ask.

Nicole Cuellar-Lopez: [00:27:57] Yeah, my pleasure.

Carol Fishman Cohen: [00:27:58] You have talked about sponsorship, this is offline. We've talked about sponsorship and the role of sponsorship in your career and in angel investing. And I wanted to know if you could elaborate on that a little bit for our audience.

Nicole Cuellar-Lopez: [00:28:12] Yes. So I think about sponsorship as the next level of mentorship. In mentorship, you might seek someone out who has a little bit more experience, or maybe a lot more experienced than you for their advice and their wisdom.

Now in sponsorship, this is when you have a relationship with someone who might be your senior or might be senior to you, or might be more influential than you in order for them to be your advocate, to speak your name in rooms where your name hasn't been spoken to build your reputation, maybe to give you information that you can act on to do great things in your role. And I was fortunate at Uber to have some really wonderful sponsors that made it possible for me to stay at the company as long as I did. I think that people oftentimes... so I would categorize myself as an elder millennial, and millennials and Gen Z, we get a reputation for hopping around companies every one to two years. And this is my own opinion, but in my own perspective, when you feel like you don't have a connection to folks and people who are rooting for you, it's really hard to stick around.

It's really hard to see a path for yourself, but when you have a sponsor, it's a great feeling to know that someone is believing in you and someone is invested in your success. So I would definitely urge women to make sure that they do have that sponsor at work and that you are creating those relationships with your people who are junior to you, people who are lateral to you and people who are above you who can help you operate well in your space.

And if you're in a role where an equity package is part of your compensation, you don't get all of that equity at once when you walk in the door. And most equity packages are set up to vest over four years time or even more. So it really matters every month or every quarter, every year that you stay, you're vesting more of your package.

And if you're turning around and leaving companies one year in or two years in, you're not really able to extract all the value that you’re due with those equity packages.

Carol Fishman Cohen: [00:30:26] And how do you get a sponsor? Is it something where you need to let the relationship or relationships that you have in general develop over time and then it becomes apparent to you that certain ones are deeper or more meaningful, or even maybe reciprocal to some degree and that's how it happens? Or do you think more like, that person over there is someone I really want to be my sponsor. And, how does that work?

Nicole Cuellar-Lopez: [00:30:54] I think it can be difficult to create these relationships out of thin air. In my own experience, I found that the folks who sat on my interview panel had a voice in bringing me into the company, and those people typically are chosen because they are invested in your work or they have insights or relate to your role in some way.

So those are the people I would look to first when you're new at a company is, "Hey, who said yes to me working here and is invested in my success because they probably spoke up in favor of me having this opportunity?" And then as you go along in your path, who are you working with that is a really great thought partner or you're able to deliver value to, and you might want to be inspired to continue the conversation and continue the relationship.

Other companies have formal mentorship or sponsorship programs where you might be matched a little bit at random with someone more senior than you. But I would start with some of those organic relationships.

Carol Fishman Cohen: [00:31:57] That's great advice. I've never thought about that before. Thank you. Nicole, we're running out of time now and we need to wrap up the conversation.

And I wanted to ask you the question that we ask all of our podcast guests, and that is, what is your best piece of advice for our relauncher audience? Even if it's something we've already talked about today?

Nicole Cuellar-Lopez: [00:32:19] My best piece of advice for relaunchers is to seek opportunities where you feel inspired to take ownership of the work. And that might be because you're so invested in the mission, or it might be literal ownership in, "I want to be invested in this company. I want to be owning a piece of it as I work towards its success." But for me, there's been nothing better than feeling like an owner in the work that I do.

Carol Fishman Cohen: [00:32:47] Wow. Well, Nicole, thank you so much for joining us today. I found this so enlightening and I know that our audience is going to learn a lot. Nicole, how can people find out more about Pipeline Angels?

Nicole Cuellar-Lopez: [00:33:04] The best way to find out more about Pipeline Angels is the website PipelineAngels.com. That's P I P E L I N E A N G E L S.com.

Carol Fishman Cohen: [00:33:16] Thank you, Nicole. Thank you so much for sharing all of your knowledge today.

Nicole Cuellar-Lopez: [00:33:21] My pleasure. Thanks for having me Carol.

Carol Fishman Cohen: [00:33:23] And thanks for listening to 3,2,1 iRelaunch the podcast where we discuss strategies, advice and success stories about returning to work after a career break. I'm Carol Fishman Cohen, the CEO and co-founder of iRelaunch and your host for more information on iRelaunch conferences and events to sign up for our job board and access our return to work tools and resources, go to iRelaunch.com.

And if you liked this podcast, be sure to rate it on Apple podcasts and your favorite podcast platform, and be sure to share this podcast with a friend on Facebook, Instagram, and other social media. Thanks for joining us. .