Jan. 6, 2021

#13: Heather Hiles - Founder and CEO of Imminent Equity and Board Member at Udemy

My guest for this episode is Heather Hiles. Heather has over 30 years of experience in education. She founded non-profit and for-profit organizations in Break-the-Cycle, San Francisco Works, Pathbrite, and Imminent Equity. She is currently a board member at Udemy and Black Girls Code, as well as an advisor for startup founders. 

In this episode she talks about her founding experiences at both the for-profit and non-profit level, her investing experiences, and some financial literacy tips for beginners. Most importantly, we talk about why being comfortable in your own skin and blocking out the noise from others can really help you pursue your dreams.

Show Notes

Introduction [0:00]

How She Became Interested in the Fields of Education, Technology [02:20] 

 How She Ignored Criticism to Pursue Her Dreams [08:20]

How She Founded Four Organizations [18:12]

Her Role as an Advisor, and a Board Member in Different Organizations [26:00] 

Did She Ever Envision Herself Becoming a CEO, Advisor, Leader, and Board Member [30:45]

Why She Joined the Board of Black Girls CODE [35:35]

Challenges of Starting a Non-Profit Versus a For-Profit Organization [37:50]

What Got Her Interested in Venture Capital and Why She Started Imminent Equity [43:31]

How She Got Past the Obstacles in Her Career [47:48]

How People Can Move Forward to Acquire Assets [50:57]

Her Advice for Black Founders Looking to Raise Capital [58:35]

Key Takeaways

  • My passion came from a couple of places, and one is that I have been mindful for a lot of different reasons, what the American dream has been...
  • What I realized then and there was that not everybody was blessed to get exposed to a good education, or role models...
  • If I can be of service, I want to be of service, especially for people who are ignored...
  • You have to acknowledge different people come from different life experiences, have different kinds of assets, understandings and exposure as a as a result. So, we are not all starting at the same place…
  • “Everybody wants to be able to take care of themselves and their families, this just a basic human need...”
  • I really am somebody who, for a lot of my life has been self taught...
  • I'm passionate about learning, and helping people have the feeling that they can learn whatever they want because I want people to feel personally empowered.
  • “In today's society, the thing that scares most people, most Americans, more than anything, is a free Negro.”
  • “I trust that if people really felt free, were okay being themselves and doing what they wanted to do, we could all probably get along better...”
  • I think White America and this whole economy has been built off the backs of the talents, resilience and productivity of Black people...
  • In corporate America, White people love to tap our brilliance, our culture, and our capabilities. But they want us to be contained...
  • “I think, the first and most important commitment is for us to know ourselves, to love ourselves, to be content, to feel like we're enough, and we're whole, and then we can share what we have to offer with others...”
  • “I think you don't grow unless you can be honest with yourself and others who love you can be honest with you, and vice versa.”
  • “I am about personal empowerment, self actualization...”
  • “What I've been clear about as a Black American is that formal education and educational institutions were not made for us to be successful...”
  • “Advisor and directors are really different things. An advisor can be much less formal, and it really can be more bespoke...”
  • When you are on the board of directors with a big company like Udemy, you have fiduciary responsibilities, you sign off on the audit, and much more.
  • “I'm not there to micromanage or do anything, I'm just there to kind of be at the governing level...”
  • Exposure is really important, and the earlier, the better—because you can't become something you don't even understand exists...
  • If you want to get good at something, you have to practice it every day or be consistent.
  • “You can't become something that you don't know exists.”
  • “I expect my generation to do better, to open more doors and to educate our young people and our upcoming generation a lot better than what people did for us…”
  • “I actually believe most non-profits should create value and be able to generate revenue for the services that they provide, that a public sector entity can't do itself...”
  • “Portfolios are proven to improve critical thinking skills, metacognition, meta learning, writing proficiencies...”
  • “Black women are still the most undercapitalized founder communities right now…”
  • There is a need for good VCs and investors who are not just trying to take you apart for parts or make the most money they can off you at whatever expense.
  • Just expect to keep learning and changing, it is just not going to stop.
  • The primary and the biggest asset that drives a lot of our financial behavior in this society is home ownership. Then, there is real estate and education.
  • “Investing in your own knowledge, in your own credentials, or in your own experiences that you can monetize in different ways, is a big investment in yourself, and you will see the return…”
  • You should think of your own life as a balance sheet. You should have some assets and your assets should be worth more than your liabilities, and that is the difference between those two that tells you what your net worth is.
  • There are a number of Black investors, who are holding themselves out there to be accountable to us and to investing in us, so we should be knocking at their doors a lot.
  • If you are not persistent, and you are not willing to be persistent and tenacious, you're not really an entrepreneur.

Where to Find Heather Hiles

Twitter: @HeatherHiles: https://twitter.com/HeatherHiles

LinkedIn:  linkedin.com/in/heather-hiles


Note: Black Enterprise Network transcripts are generated using speech recognition software and human transcription. They may contain errors, although we do our best to avoid them. Please check the corresponding audio before quoting a transcript in print. Questions? Errors found in a transcript? Email us! 

Kimmiko James  0:00  
Before we get into the episode, I wanted to take a quick second to talk about the new website I've released for the podcast. So the website has been something that's always been on my mind, especially when there's so many resources being mentioned. And these episodes, there's so many social media links that are being mentioned. But it's not always as easy to look up. And yeah, that's why I got the website, I'm super excited for you to check it out at Black enterprise network.fm. I'll go a little bit more in depth and the outbreak for this episode and the following episodes just because I feel like it's important to just promote the website and the resources that are available through thanks for listening. In this episode, I had the pleasure of speaking with Heather Hiles. She talks about her founding experience of both the for profit and nonprofit level, her investing experiences, and she even shares some financial literacy tips for beginners. Most importantly, we talk about why being comfortable in your own skin and blocking out the noise from others can really help you pursue your dreams, even some even more so to the point where basically, you feel free without so much pressure. And I personally believe that that's what most people should strive to be at, at some point in their lives. Let's get into it a

small percentage of black people are currently represented in the tech industry and entrepreneurial spaces. This includes engineers, startup founders, investors, especially those that hold leadership roles. I want to share your stories. So yeah, so I was checking out your LinkedIn and a different article. And it seems like you have well, it doesn't seem like you, you do have a lot of experience working in education technology for about 25 years, correct me if I'm wrong.

Heather Hiles  1:52  
30 years, I've been added different ways. Yeah.

Kimmiko James  1:55  
Oh, that's crazy.

Unknown Speaker  1:56  
I'm mad. Oh,

Unknown Speaker  1:57  
no. I mean, I didn't

Unknown Speaker  2:00  
have to look in your eye and

Kimmiko James  2:03  
tell me otherwise. I mean, it was more of a look of just being impressed of like putting 30 years of your life into something you're just so passionate about. When other people they might not be able to put a year into something that's just amazing to me nothing about age. So. So yeah, I just love to know what got you interested in the fields of education, technology? And yeah, just your various experiences over the last 30 years. Okay.

Heather Hiles  2:28  
Well, the last part of that question, we'll see where we can go with the first part. You know, my passion came from a couple of places. One is that I have just been mindful for a lot of different reasons that the the American dream has been, you get a good education, you can put it to work, you can have a good job, you can buy a home, you can do these things. And over time, and through, especially over generations, you can build wealth for yourself, your family, your people. And that's been somewhere inside of me, maybe it's from my father's side of family. They started the first black owned mortuary in LA, a long time ago. So maybe that comes from that, that that genealogy. I was recruited to play basketball at UC Berkeley, which is how I got up to Cal. And I turned down the scholarship because I wanted to be doing all these other great things that I saw going on. When I came from my visit, people were protesting apartheid and Sproul Hall, people from all over the worlds were in the cafes, talking about really interesting things. And I want to be part of all that. And so I went home to my mom, I was raised by my mom. And I said, Look, I don't want to do any more tours. It's all about Berkeley. And she was like, great. And then I said, but thing is I don't want to play basketball. And she was she was upset, and I now understand why it was my scholarship and a full ride. And she thought I was crazy. And she's like, Well, can you get accepted that I and I did have, you know, pretty decent grades in AP courses. And anyway, I got admitted. And the thing was, I had to have a full time job and to work my way through through Berkeley. And so I worked with this former Black Panther who had stayed in Berkeley, he you know, he defended make the best in peace, Ronnie Stevens and he, he protected Angela Davis, he was bringing food and everything to the schools and he was a real Black Panther. He went to Cal matriculated himself, and he created this program called break the cycle. And what what we did is we had, I became the CEO of that nonprofit. We trained UC students about their history and about all the sacrifices made so we could just get an education. And then we taught them how to be good tutors. We bring them to public schools, elementary grades like kindergarten through third grade, and we'd have them too

During these kids at a ratio of one to four, and it made all the difference, these kids weren't getting good grades on standardized tests, they weren't getting good grades in the classroom. They weren't, they were under educated in a lot of ways, and they need a lot of support. And this model was very effective. I worked a lot with not only setting up the kind of operations and expanding but working with the families to say, Hey, you know, your kids need to be in bed by eight o'clock at night, and they need to be bathed and fed and ready to go. And this is what it takes for your kids, because they were intimidated by the teachers, and they didn't, and the principals because a lot of these families, their parents hadn't had success in school. So what I've realized then in there was that not everybody was blessed to get exposed to a good education, I was blessed to have my role models of you know, the thing about having a single mom, as my parent was, she worked and I saw her work and pay the bills. And I saw that she had to, you know, do work every day to get it done. And so I expected to support myself and to have to learn some skills and get a good job. And I was blessed in that way. So I ended up writing my honors thesis about the achievement gap before it was called that. And I talked about how, you know, not everybody got the same equitable equity of opportunity even to realize their dreams. And so the one thing that is through line throughout my career, my 30 years is usually in my day job sometimes fall on the volunteer side, trying to help people realize their, you know, realize their dreams. And that could be of getting good grades in high school, going to college, could be getting a job, getting a better job, could be starting a business, getting access to capital, whatever the rung of the ladder, if I can be of service I want to be of service, especially for people who are ignored. And one of the things that has troubled me is this myth of meritocracy. That, as if, you know, just letting anybody in, you know, apply to UC Berkeley is not really the kind of meritocracy I'm talking about. You have to acknowledge different people come from different life experiences, and have different kinds of assets and understandings and exposure as a as a result. And so we're not all starting at the same place. And we need different kinds of supports to get us where we want to be. Yeah, I kind of want to just backtrack just a little bit about the the American dream, which I think still rings true today, honestly. Yeah. Like you go through your general lower level education through preschool Elementary, then you hit Middle School, the high school hit college, get that I guess, quotation, where his dream job, and then get a family house, etc. So I think that still rings true today. Yeah.

I think worldwide is not even as country worldwide, what people want is they want a good job where they feel like they can master something where they have some something to offer can be productive, and where they put themselves in their families. Everybody wants to be able to take care of themselves and their families like this just a basic human need.

Kimmiko James  8:20  
But I would say I feel like a lot of people would have called you crazy back then, like your mom did when you just gave up, you know, a full ride scholarship, a lot of students would jump at the opportunity to have their college paid for in full, and then they can work that dream job after. But you kind of like separated yourself from that to do things you actually cared about. And I'm sure people thought you were crazy doing a lot of volunteerism as well. So like, I don't know how to word this, but like, how did you just ignore them? break the mold and ignore them and do what you felt was best for you.

Heather Hiles  8:54  
You know, I think part of it comes out of the fact that I I have always felt like an outsider, like if, like a true community of one, like that was my life experience growing up I was, you know, raised by a white woman in a black community, have a black had a black father and and was never never felt 100% of any kind of family or community and even his reflect up to it up through high school. Like my high school experience was super fragmented. I was the only person of color in AP classes in Santa Barbara High School. My mother had moved us out of South Central la into Santa Barbara, so I could go to a good public high school. And I was the only kid of color student of color in those courses. All my friends were black and brown. I played basketball so I had different friends there. I you know, I had boyfriends because I wasn't prepared to be gay and out and I had girlfriends but it was so fun. fragmented. And it wasn't till I got to Cal that I started to try to integrate my life and Berkeley was the perfect opportunity for me to do that. You know, you have some fits and starts, I tried to be straight again. So I had a boyfriend who played football IQ cow, that didn't work out because I fell in love with, with with one of my best friends who was female. And so you know, you know, I stumbled a little bit I had to come out of once I became an aka and that was a little bit rough waters and stuff like that. But for the most part, my political and my personal and my identity, I started to feel comfortable in my own skin. And I even chose a major which was multi disciplinary meaning it was called development studies, which is the study of developing countries, but I had to pick a region, which was West Africa, I had picked it like an emphasis within that, which was economics. And I had to pick my own courses that would correspond to my major. And more so than somebody who just says, You're an engineering major, and these are the courses you have to take. And so I really am somebody who is for has, for a lot of my life, I've been self taught, I've been interested and learn, learn that I could learn by myself. Like from the age of five, I've been tinkering with stuff and taking stuff apart, putting it back together. So I think when I look at society, and this comes back to why I'm passionate about learning, and feeling in helping people have that feeling that they can learn whatever they want, because I want people to feel personally empowered, I think the best gift I got from my mother was all kinds of freedom. If anything, I was the adults in our relationship. But that meant that I really called all my own shots, I did exactly what I wanted to do. And then I got to become who I needed to become. And I didn't have many social norms, I didn't have anywhere but up to go, I didn't have anywhere, I didn't have anyone expecting me to do X, Y, and Z. So then I was gonna disappoint them. And that's a lot of freedom. And I think actually, in today's society, the thing that scares most people, most Americans more than anything, is a free Negro because we were brought here to be free. And, and but the thing is, is if you feel liberated, like you understand how it works, and how, what you need to do to be happy in your life, you can be free and, and that's, I think that's the concept that I'm most enamored of in the world is unlocking people's freedom, like I just want everybody to feel free. I trust that if people really felt free and that they were okay, being themselves and doing what they wanted to do, that we could all probably get along better because so many people are playing the zero sum game I got to take from you so I can have enough and I gotta have more than you and that stuff's not really working. I don't think that well for us as a society. But I think the thing is, is that I'm I am an unusual animal in that I've always felt free to just be and and I think a lot of people are just told by society and a lot of and, you know, unspecific unconscious and a lot of unconscious ways, you're supposed to fit into this mold, you're supposed to do this. And that's the pathway to, to ultimate happiness, which is usually a crack of mass. And we should just be doing ourselves and getting to be better in touch with who we are, and trying to express who we are the better versions of that. I think that's all it's about.

Kimmiko James  13:49  
Exactly agreed. 100% like, as someone that I was in college opened up a lot of that perspective for me as well, compared to middle school in high school, where everything's very clouded. And you're very confused. For me in high school was kind of the same thing of like, I grew up middle school with a bunch of black and Mexican friends. And then my mom kind of did what your mom did, she wouldn't need to go to high school in a good neighborhood, but that it didn't feel good to me. It felt weird, being a lot of the AP classes with the bunch of white students, but didn't really talk. And yeah, it goes beyond that. But it just wasn't comfortable. So I was like, I don't know who I am, or what I want to be right. But I will say coming to UC Davis or for anyone coming to college, it's like, I don't know, the more you see people just doing their own thing, not given a down kind of just opens you up to that as well.

Heather Hiles  14:42  
Yeah, it's less, it's less it becomes less scary and you realize there is what is the downside? What's the consequence of you being you? I want more of you. I want to know exactly what you're about. I want to feel the whole 100% of you, not 50% and And you're a beautiful being in all your manifestations. And I just want to experience that, what's the consequence of you being you, you might offend somebody, they don't need to worry about being themselves, they don't need to worry about you doing you, number one, unless you're hurting somebody, and I don't think you're gonna hurt anybody. So unless, you know, just assuming everybody safe and nobody's being themselves is going to hurt somebody else. I think the only consequence is that you're going to look up sometime and feel unfulfilled or feel like you didn't get to experience all that was available to you just because you're afraid of being your full self and being your true self. That's the only consequence I can imagine is that we get robbed of who the real Kimmiko is, and what's really going on there. Other than that, I mean, people try to scare you, I think into being and I see this in corporate America, with black women in particular, I think white America has been this whole economy has been built off the blacks of off the talents and resilience and productivity of black people. And I think that when you get into corporate America, white people love to tap, love to tap our brilliance in our culture and our capabilities. But they want you to be contained, like they want to contain you though, they don't want you to surpass them, they don't want you to shine, they don't want you to be the star on the tree, they want you to be their little super secret sauce or something like that. And that's one of the things that really bothers me and all of this rush to, to push capital out there is yet again, it's about a lot of people who just make money by making money and just doing documents and being able to own more, because I started with more. And that kind of energy of white people just wanting to tap an untapped market is really bothersome to me, and we need to be able to invest in ourselves. So we can be our best selves and reinvest in our, in our own communities. And so that's one of the things that's really top of mind for me right now. But

Unknown Speaker  17:13  
the visual level,

Heather Hiles  17:15  
I think, the first and most important commitment is for us to be to know ourselves, to love ourselves, to be content, to feel like we're enough, and we're whole, and then we can share what we have to offer with others.

Kimmiko James  17:29  
Thank you for sharing your perspective on that. It's it's very admirable. And I would say very honest,

Heather Hiles  17:35  
I mean, I that's one of the things that I try to live by, in my professional and my personal life is, is to be intellectually honest with myself, and try to make safe environments for people to be able to be honest with themselves. I think you don't grow unless you can be honest with yourself and others around you who love you can be honest with you, and vice versa. And I it doesn't need to be punitive. But I think I think that there's a lot of harm that and damage this cause when people aren't honest, really honest about what's working, what's not, why not all that kind of stuff.

Kimmiko James  18:12  
I was originally gonna just ask about path bright, but you corrected me and said you had founded for organizations, which is that's that's amazingly crazy. And in a good way. So what were those four? And were they all based around education, since that's something you've been passionate about? Yeah.

Heather Hiles  18:32  
So there's a slightly bigger frame beyond education that I would say that I'm about, about personal empowerment, self actualization. And for a lot of people that's looked like academic success, or in my career, I started out doing a lot of academic success. And the thing I wanted to say, which we can get back to maybe a little bit later is that what I've been clear about as a black American is that formal education and educational institutions were not made for us to be successful. So that's really inspired me to help unlock the keys to the information and the secrets that people have wanted to hold dear and within their cliques. And so one of the things that really motivates me is when I can make at scale, the the answers to the test available, the keys to the kingdom within within reach. And so that looks like academic and it looks like economic development. It looks like business opportunities. It looks like access to capital, it looks like access to information to build your business. It looks like lots of different things. So it's more than just education or learning. But learning is a key and you can be a fantastic learner and successful without being successful in traditionally Education, which wasn't built for a lot of us. And so that's been a lot of my passion, which is different from the kind of the traditional education systems, which I've succeeded on a personal level of times and failed at an institutional level to, to do what I want to deliver for a lot of reasons, because I don't like the constraints of traditional education. So the first organization that I founded was called SF works. And what that did was it got employers to identify jobs where they couldn't find enough and retain enough talent. And then I built bespoke training programs that were a combination of traditional education like Business English, or business math, with online e learning solutions with on the job training, and retention and mentorship and other supports, to get people from welfare into those jobs. And with SF works, we were able to get 11,000 women, mostly from welfare or ex felon and ex felons, off those out of those institutions and into living wage jobs. That was the first nonprofit, I built the second nonprofit, I built what's called urn which help low income people save for their first assets, because we know that the way to break the cycle of poverty is by acquiring an asset. And the thing is, is that economists have said that by the middle of this century, if, if the trajectory doesn't change in our economy, black median wealth will go to zero. And actually, I've talked with the economist who did the study, and I said, actually, that was being positive. They said, it could be sub zero, by the middle of the century. So I feel a tremendous amount of pressure to help build the economic engine and the way that is for black and brown people. And the way that I found to do that is we've got to acquire assets, and we've got to grow them, we've got to pass them on to our children so that they can live better than we lived in. And we have failed at that as black Americans for a lot of different reasons. But we fit we're failing right now. And so we've got to change your trajectory. And so earn was the second nonprofit I started. And over 30,000, San Franciscans have been able to learn about assets, learn about investing, learn how to budget and acquired assets in San Francisco. So we've matched what they saved, sometimes two to one, sometimes seven to one for home ownership. But 30,000 people have acquired their first asset, so they're breaking the cycle of poverty. The first for profit business I started was a professional services company that consulted to foundations and philanthropists, so that they could have better more strategic focus, have more focus on outcomes and impact. And I worked with over 100 different organizations and people. The biggest gig I had, in my like nine years of doing the work was I worked on a by a billion dollar grant and investment into global biodiversity for the Gordon and Betty Moore foundation. And then the second company I started after that, I realized I didn't want to be in professional services, because you basically are selling your time. And there's no scaling that at a certain point, you can get a bunch of people under you. But when every client wants to talk to you, there's only but so many ways you can do that. You can't make money while you're sleeping. So I bought some real estate. But more importantly, I started a tech company. And I've always been a technophile. And I enjoyed new technologies. And so I learned about a technology called e portfolios, and I built the first enterprise wide digital cloud based cloud driven portfolio platform. And my first customer was Stanford University. That's where I raised $12 million in venture capital. I sold the company a few years later, we had a good exit from my investors. And and then since then, I've been doing work with other big organizations like Bill and Melinda Gates Foundation, like starting up a statewide upskilling Community College for the state of California. And now I'm getting to go back to what do I want to do next as an entrepreneur, and it's more around investing. Then the last thing I'll say is about where I'm headed is that I joined the board of you to me, yeah, and so I've been on the board of lots of nonprofits. I'm on the board of Black Girls CODE, give them a shout out. This was really great for me, they asked me to be a board member last year and I had to turn them down because it was conflict of interest. And they came back which I was just so surprised and so grateful. And this is an amazing company because the whole thing I talked about, about making Access to Information affordable and accessible is exactly what you to me has figured out, they built the first real learning teaching marketplace. And so our instructors make money and some of them make really great money teaching courses online. And then 35 million people worldwide are learning through these courses, and they're affordable. And then, and so that's a, it's been really fun to be part of the strategic planning, some of the product development, some of the rebranding, but I'm really enjoying being part of the board.

Kimmiko James  25:35  
Yeah, yeah, I love Udemy and Black Girls CODE Udemy, very cheap courses over the last few years, I've used it, like 999 to 1099 for just something that's obviously it's not gonna replace university level stuff. But I've learned quite a bit in terms of side projects and web development and other things through you to me, so love it very much. What role do you play as like an advisor, or as a board member in these different organizations? Like, do you have like a big impact on diversity solving the very hard hard problems? or What role do you play? Exactly?

Heather Hiles  26:10  
Yeah, so advisor and directors are really different things. So advisor can be much less formal, and it really can be more bespoke. So what one CEO needs, I'm advising probably 15 companies right now. And

Kimmiko James  26:29  
hey, guys, Pardon the Interruption, but I just wanted to take a minute to talk about the new black enterprise network podcast website. If you've ever been curious about what a guest looks like, or what their social media links are, then we have detailed guest profiles for each episode. And there's also detailed show notes with time markers in case you wanted to find a specific point or piece of advice without listening to the entire episode. There's also readable episode transcriptions. And also the website allows you to easily send questions and feedback, if you want to get in contact with me, just know that the website will be updated on a weekly basis. So if you don't see something done already, then it will be done soon. Check it out at Black enterprise network.fm.

Heather Hiles  27:12  
One, one CEO might need just to be able to talk about the loneliness and the pressures of being the CEO, which are very real, and another CEO might need help. I'm working with one company to sell her company and the assets of the company. So it's a very focused set of activities I'm doing, putting her in front of the right companies, we're in due diligence with to two different entities right now. And there's another company, I don't know if you know, shirelle Dorsey of the plug in Yeah, it's a great newsletter. And it's all about kind of the black capital entrepreneur ecosystem. She's working on a new product that I won't spill the beans on today. But we do weekly sessions together. And I've helped her get the pitch deck, right for the round, she's raising, and I've gone through the wireframes of her for her product, and whatever I'm introducing her to her first founding customers, and just trying to help her be set up to be, you know, to build a billion dollar company and, and so it really depends on the entrepreneur and how I'm going to advise them and how I'll help them. I volunteered for momentum at Morehouse and helped with a full stack dev training boot camp for for black folks this summer and during the fall. So it depends on what what of my skills are needed. So that's advising, when you're on the board of directors with a big company like Udemy, which has like over a $3 billion valuation, you have fiduciary responsibilities, you know, they do background checks, you're responsible for governing a really important entity, you sign off on the audit, and you're saying that you believe the audit to be true. And there's a lot more to it. And you know, if we ever go public, which I really hope and pray and I think we will someday, you know, there's a lot of scrutiny on the board, the board members around what they're doing and how they're doing and making sure that you're mitigating and managing for making sure there are no disasters that are going to happen. And then all simultaneously, I think, a really good director. The way that I describe it is you have space to be a strategic thinker, whereas the people, the management team are in the foxhole, and they don't get that perspective. So you should also be able to like, anticipate, hey, this is trending right now and you're gonna have to deal with this. You know, your competitors are going here or I think of a blind back there. And let's shed some light. Let's take a look at that. It's not to micromanage. You are the boss of you who are responsible for hiring and firing the CEO. But you really shouldn't micromanage the CEO, you should wait to be invited into projects, if they really need you to get deep into something like they've asked me to look into their rebranding and certain product related questions. But other than that, I'm not there to micromanage or do anything, I'm just there to kind of be at the governing level. And that's different from an director what a director does at a startup on that board. If it's like three or five people versus what you do at a large company board, it also looks different.

Kimmiko James  30:45  
I think to myself, when I'm like a teenager, I would say I was more knowledgeable things I would say compared to middle school. I can't even imagine seeing myself now and just believing this is me doing these things like being more outspoken because I'm a natural introvert, if you can tell already started starting a podcast being more, I guess, more active on social media in terms of LinkedIn and networking, and just putting myself out there in general. Yeah, go for you. Did you ever think that you would become this this founder, this CEO, this advisor, this this leader, this board member, etc? Like Did you ever think this would be in your your future or your path?

Heather Hiles  31:27  
Well, so in the early years, I didn't have an understanding of how it worked. I've always been entrepreneurial. I've always liked making money. I like to help other people make money too. But I've always been like that, that kid like, I got one year, I got an Easy Bake Oven. I don't even know if you know what those are.

Kimmiko James  31:47  
Yeah, I do.

Heather Hiles  31:49  
predates your time, or whatever. But anyway, I live for this Easy Bake, I like to cook a lot. So I live for it. But as soon as I was making those cakes, I was selling those cakes. And I'm some bad kid. And I was always a Tinker. And that was something Also, my mother would just like, let me take stuff apart in the garage and put it back together and Tinker. So I had that freedom. And I didn't know what that was going to what I could grow up to be by high school, I wasn't quite sure that I would be anything by high school, I thought I might not live to be the age that I am now. And I didn't know what was going to happen. But by college, I realized I could get A's and B's in college and that I could, I could keep up with them. And so by college, then I think I had all kinds of dreams. And I'm still living those out. But I'm, I'm hitting the things that I had dreamt about doing. And so that's a really humbling interesting experience. I remember applying to Yale for business school and thinking, that's not gonna happen, but it did. And shoot, I made it out nine I know finance pretty well. So you know, yeah, it's weird how that happens along the way. But that's why exposure is so important. And the earlier the better. You know, my stepdaughter, she went to Howard, by the time she went to Howard, she expected to become an engineer. And so by the time she graduated Howard, she was an engineer. And she works at Boeing. And she's, you know, but she she hit her mother was putting those expectations into her, like, by age 10, you know, so the exposure is important because you can't become something you don't even understand exists. And and that's a really big deal around inequity and opportunity and all that jazz. But yeah, it's it's interesting. I mean, a lot of what I fantasize about in life, I'm I'm living right now, which is a weird thing to do. My wife is always questioning me about like, when is enough enough? And when will you feel like you're actually successful? And well, you know, when we feel like you've had the impact you want to have at the scale you want to have and I don't have any of those feelings yet, but I'm actually trying to work on feeling more content and like, I'm enough right now.

Kimmiko James  34:11  
Yeah, it's not an easy place to get to especially black person. Well, I just want to highlight a quote that I resonate with, and I feel like a lot of black Americans resonate with as well. You can't become something that you don't know exists. Exactly. That was me like when you I don't know why we're so similar, but I feel like with my dad, very hustler, hardworking man, and with me on the playground at school, I would sell Pokemon cards. I would sell snacks. I would sell toys right here. I don't know why I was doing it. But I was doing it and I liked the money I was getting. Yes. And then when it came to high school, just being on the computer all day. time fixing the internet just fixing little things for my mom, my family. I mean, I didn't know that could be related to engineering in any kind of way over it, I guess. But if I would have known that there was a path available to learn about entrepreneurship outside of just selling things, or just, you know, knowing how to use a computer for computer science, which is, I think getting a head start is very helpful, because in college, it just rips you to shreds. So, right, right, like you said, just the lack of equitable access to these things in certain communities. It's, it's very unfortunate.

Heather Hiles  35:36  
Exactly. And then that's why I, you know, join the board of Black Girls CODE code when Kimberly set up the first board, because we've got to, I feel a very strong obligation to continue to share the information with our girls and with our young people as they're growing up. And I feel like one of the things that, again, I don't know all the reasons why I'm not a social scientist, but I feel like the generation my parents generation of black people had been so have been holding on with dear life, to continue to, to, to achieve what they need to achieve. And they've, I think, not done a good job of mentoring and shepherding and bringing up my generation or generations younger than me. And so I want to want to correct that. And I want, I expect my generation to do better, to open more doors and to educate our young people and our upcoming generation a lot better than what people did for us. Because all of the almost most of the black professionals I know, have stories about the people who could have been there for them, but really weren't and didn't learn how to do that very well. I think a lot of other communities have figured out how to take care of themselves better, and to get their their young people to really advance and take it to the next level. We're going in the wrong direction. A lot of ways, and I'm trying to untangle why that is. But I think it's important that we all share the information that people have been hoarding, and we really try to bring others along with us. It's

Kimmiko James  37:28  
at least from what I've learned in my African American Studies class, and just from talking to a lot of black professionals I've interviewed it seems very systemic, of like a lot of and I'm sure you know, this, too, like a lot of things have been set in place the last few 100 years. And we're slowly like you said slowly untangling things, but there's still a lot that needs to be figured out and set in place. So

Heather Hiles  37:50  
yeah, that's right. That's right.

Kimmiko James  37:52  
I wanted to ask, like what have been some of the challenges of starting a nonprofit versus a for profit, because of the nonprofit a lot of I mean, both have their challenges. But a lot of people are scared to start a nonprofit, because you have to ask for money constantly. And you never know when the money's gonna stop and things like that. So what is your experience? So

Heather Hiles  38:12  
you know, that's a that's a, I think that's a myth, what you just said at the end there about nonprofits just have to be on the door raising money all the time. So first of all nonprofits have what a for profit we call profit margin. Nonprofits called retained earnings. And so most large nonprofits have a lot of money in the bank have retained earnings. So they don't live year to year and they're not like going, Oh, my gosh, if we don't raise this $100,000 we're gonna have to shut down. Large nonprofits that are effective, have a lot of money in the bank, and they're continuing to save money. So they're not dependent on philanthropy. And, and whether you want to call it a nonprofit or think of it more as a social enterprise, I actually believe a lot of nonprofits should be in the business of creating value that people or entities will pay for, and that they don't have to stay dependent on philanthropic gifts. So I'll give you an example. So I stood up Cal bright college, which is the first statewide Community College to upskill, underemployed Californians. And it was a startup within the governmental sector. And I wrote the business plan for this business and I said, what we're gonna do is we're going to partner with employers. We'll learn what jobs they have a way to train people for their jobs. And when Amazon wants to hire one of our graduates they will pay 15 or 20% of this the annual salary of that higher they will pay to calibrate college for the privilege of getting a train person who hits the ground running day one. Now So financial model where my projections were, we would be financially self sustainable by year seven. Unfortunately, the government didn't actually want us to make a financially self sustainable entity. And that's one of the reasons I wasn't a good fit for staying at Cal bright college and I resigned earlier this year, I actually believe most nonprofits should create value and be able to generate revenue for the services that they provide that a public sector entity can't do itself. And they need nonprofits to do the work. Or, you know, like my example, with employers, they need this service so they can pay when I had SF works in the late 1990s. Employers were they were giving us philanthropic grants. But once I demonstrated to UCSF, my whole training system, got them people that not only were trained for their jobs for day one, but also that they would retain for a long period of time, they took the whole program from beginning to end that I had built out and they brought it in house into their HR departments. And so that kind of nonprofit is one that is called an I would think of as a demonstration project. So I didn't have the goal of having SF works be out there forever. I wanted to prove to policymakers and others that if you invest in teaching people hard skills, they can get permanently off welfare instead of staying dependent on it. If you teach someone how to go work at McDonald's, and they can't make enough to survive and take care of their families, they're always going to be dependent on some kind of welfare. But if you can get them a living wage shop and a career path where they can continue to advance and make more money, and do better, they can get completely off welfare. And that was the business case that I got the businesses involved in. But it was meant to prove that out not to just do it forever, and be relied upon philanthropy. One could argue that path bright which was a for profit company, where I raise venture capital return to investors, money, portfolios are proven to improve critical thinking skills, metacognition, meta learning, writing proficiencies. And I wanted every student at CSU Fresno every student in a public sector institution to be able to have the best the best of technology, not the worst of it, in their learning experiences. And so I had a social mission, even though we were making money and profiting and making a profit margin. Thanks, sir. Thanks

Kimmiko James  42:37  
for breaking that myth. Because I mean, even myself, I've thought about wanting to start a nonprofit one day, and I'm just like, I was just so nervous about having to rely on donations and stuff. So

Heather Hiles  42:48  
yeah, and and that is in that and that doesn't mean that there aren't some really great nonprofits that are that are reliant, that are not relying on on philanthropy, some are and so it depends on what the model is that you make. And some things are meant to be funded by the government or by donations. And so it really, you know, depends everything depends on what what your scenario is. But if you can think in the lead through the lens of social enterprise, something that creates value, and you know, where the source of the fuel is going to be to create that value. You know, you're working with a winning model, whether it's in the for profit or nonprofit sector.

Kimmiko James  43:31  
Are you interested in venture capital, and what influenced you don't want to start up m&a equity.

Heather Hiles  43:38  
What got me interested in venture capital is that mentioned, you know, I raised $12 million in venture capital for my fund for my company, rather. And for a really long time, I had the distinction, I think, through 2018, the distinction of being the black woman founder who had raised the most money, and then the black woman founder who had the biggest exit. And I was, I was embarrassed and ashamed to even tell anybody when it was the reality because told me that that was a lot of money for a startup, but it's not a lot of money in the sense of venture capital. And I thought that if I've raised the most, we're really undercapitalized. And black women are still the most undercapitalized founder communities right now. And so it is really heartbreaking. And that was the beginning of me caring about people getting access to capital because I know how hard it was for me. In fact, I wrote a blog in recode. Kara Swisher had asked me to write this in 2015. I think it's about the lack of diversity in Silicon Valley. And it's, it may still be an interesting read. I talked about how people should practice oferte inclusion it before is a buzzword, but anyway, that it talked about my very lonely experience of going on Sandhill road and pitching the VCs and just people staring at me like, Who are you? Why are you a Martian? Why are you here? You're not the executive assistant. And you're not the, you know, partners, like, Who are you? That was interesting. So that was the beginning of me wanting to do better venture capital, then I remember getting invited to the first Andreessen Horowitz get together for black founders and entrepreneurs and stuff is probably like, maybe it was like 2017, or something, I don't know, when he announced that he was going to tap the black market and how it's under, you know, undercapitalized and under tapped. And I just thought, I just don't need another white man talking about how he's going to make more money out of us. And I don't, you know, and it didn't feel good to me at all. And I was pretty underwhelmed by that whole experience. And then also, while I had my company, I had the experience of the head of the lead investor, trying to sell my company out from under me to another one of the companies in his portfolio. And it was only because one of my other board members clued me into that, that I even found out and I had to fight to hold on to my own company. And so I really, I learned the hard way that there are a lot of bad VCs who really don't give a shit about their entrepreneurs, all they care about is making more money. And so I want to be a better VC than that. I want to invest in people better, and be nurturing and help them achieve scale and success. And there's just, you know, and so there's a need for good VCs and investors who aren't just trying to take you apart for parts or, you know, make the most money they can off you at whatever expense.

Kimmiko James  47:00  
Yeah, so I think we both know that the venture capital space or raising funding in the entrepreneurial space as a whole has been very friendly to underrepresented groups, and a more specific place, black founders and even more specific black women.

Heather Hiles  47:18  
founders, well, big difference between black women and men. Yeah, for some reason, black men and white men can do this bro thing. And that leaves women at large, excluded, but really penalizes then the woman black woman entrepreneur. And I've learned that through actual research, I didn't know that exactly, for sure. But I've, I've seen the data and I know that to be to be the case.

Kimmiko James  47:48  
Yeah, I've heard a lot about the bro things. Like just the bro personality gets them past the the pitch presentations and the meetings and stuff like that. I, I didn't know it was actually successfully working. So that's also an unfortunate thing to hear. But I was just gonna ask how, I guess in your past and probably present experiences, how did you get past those obstacles, like, it can't be easy. And I've experienced those looks to my computer science classes and office hours, just people looking at you as if you don't belong and other things like that.

Heather Hiles  48:23  
Exactly. You know, I've survived at the same way you have, which is you just keep you got to believe in yourself, you've got to be grounded by what grounds you. And now pay attention to the noise and the drama. I mean, you know, I can have that experience today as easily as I could have at age 17 with being treated a certain way for the wear, you know, because who I look in the body that I inhabit. And there's not a lot I have no control over that all I have control over is how I respond to it and what I do in my life. So given that, and given that I'm not going to change how I look or anything, I'm going to just keep doing what I do.

Kimmiko James  49:08  
Yeah, it's pretty good answer. It's

Heather Hiles  49:12  
good. It's all I got.

Kimmiko James  49:15  
I mean, it just goes back to what you said earlier of like just being comfortable in your skin. And then when you when you're at that point, then nothing else really matters. But it's a work in progress for me personally.

Heather Hiles  49:26  
There you go. There you go. We're all works in progress. But the thing is, you think maybe when you're younger that like by the time you're, I don't know I am about to turn 52 on Friday, you do

Kimmiko James  49:37  
not look 52 by the way. Oh, well,

Heather Hiles  49:40  
thank you. I appreciate that. And I probably thought at 22 or something that I would have had, you know, a whole bunch of stuff like maybe everything figured out by this age. And it's funny because what happens is, your like your body and what you care about all these things actually just keep changing. So you can can't ever master it wholly, because it's like, you know, the target actually does keep moving. And so it's just like you're always a work in progress, because things are always changing. And that's why even to participate in this economy, you have to be a lifelong learner. Now, my mother had the same job for 35 years, and I've had like, 35 different jobs, because that's the world in which we live. So, yeah, just expect to keep learning and changing. It's just not going to stop.

Kimmiko James  50:30  
Exactly. best advice. best advice. So the first question of advice that I wrote down earlier, it's just about it's based around financial literacy, which I think should be taught in high schools, maybe even as early as Middle School, and in college, because a lot of people are lacking that. I'm lacking that and trying to figure it out. And like you said, assets are the key to not only Well, we'll just say they're the key to freedom,

Unknown Speaker  50:55  
financial freedom. Exactly,

Kimmiko James  50:57  
yeah. So how can people move forward to acquire some of these assets? And the sense that could you give an example of what an asset is, because a lot of people might not know what that means.

Heather Hiles  51:09  
Yeah, so the primary the the biggest asset that drives a lot of our financial behavior in this society is homeownership. You know, a lot of people have gotten from working class to middle class through and owning a home that has appreciated and insists the biggest asset class that we're aware of in it also, you know, also the reality of, you know, got a 30 year mortgage, most of us are living to pay for shelter, when we have to stay employed. So it really is the biggest asset class that we're talking about is real estate, and usually your home. And then if you can get into other investment or real estate opportunities, that's a great way to acquire more assets. But other assets are businesses, small businesses, large businesses, it's a another stream, like I was talking about with path bright, I was really enamored with the idea of building a technology that can literally be serving people working, making money, and I'm not having to do things on it all the time. And you build up equity, when you build a company that becomes more and more valuable, and you have some ownership of it. That's another major asset category. And then a third major asset category may feel a little bit less tangible, but it is education. So the more skills like so you're investing in your own your own asset right now, by going to college, at Davis to great investment, your likelihood and your income earning power has increased by at least quadruple because you went to college, because you're going to college and get a fish. So investing in your own knowledge in your own credentials, or in your own experiences that you can monetize in different ways, is a big investment in yourself, and you will see the return. Now what happens and you and you made a really good point, especially college, students get really hoodwinked a lot of times. So a lot of times people pay more for college than they should, and meaning that they're not going to necessarily see the same return, like they may not have a college where they're going to actually be able to get a job doing what they learned in college. And sometimes they pay way more than they should for it. One of the things about starting up Cal bright college, is I met people throughout the country throughout the state, but even the country, but especially in the state of California, who were 50 and even sometimes $100,000 in debt in student loan debt. And that's the only kind of debt you can't file bankruptcy against. So there are a lot of vultures taking advantage of college students, they're getting you to take out credit cards and spend those up on stuff that you shouldn't be spending money on, like, you know, gear and you know, food and stuff like that, you're gonna have to, you know, you clock up $20,000 in credit card debt, it's gonna take you a really long time to pay that off, and that's terrible. But student loan debt, you can't ever file bankruptcy, you could technically, I don't advise getting down this road. But if worse came to worse, you could file bankruptcy around credit card debt, and then you're gonna have to take seven years to clean it up and start over. But you can't do that with student loan debt. It will be there for the rest of your life. And so I've met so many people, adults who can't buy a home and who have terrible FICO scores and are just miserable because there's And saddled with this terrible debt. And so learning how to live underneath beneath your means, even if you're on you're working and you you're cobbling together your student loan money, if you can save a little bit so that you have a little bit of a nest egg, if something happens, your car breaks down or something happens, you're not in a crisis, or something else happens. And you know, you graduate and you have six months until you're, you have a job and you've got a I don't know, move and you got you need first last month's rent, these are real things that happen for people that put them in financial crises. Over time, now, what you want to do is you want to acquire your home, you got

to save money, and then you get a mortgage, and then you want to pay off the mortgage as soon as possible. A lot of people refinance, they do stuff like that, and they might be paying off mortgage, the same mortgage for, you know, 4050 years instead of even 30. And that messes up with you being able to retire and enjoy not working, which is a nice place to be. And so how you manage your finances is is a big deal. And it's worth, you can learn anything you want to learn. So it's not an excuse to say, Well, nobody taught me well go and learn it. That's what I've had to do most of my life. Go and figure it out. There's lots of information from Credit Karma to there's a great app created by a sister for especially focusing for kids called goal setter. And Tanya van court is the sister who created she was, I think born and raised here in Oakland, and goal setter, she has a mission of having at least a million black kids on her platform, who are all learning how to save money from their allowance or whatever their parents get involved. They learn how to save money, and then they learn how to invest it. And this is what we have to learn ourselves and for and teach our kids and our community. I have sisters, I have family members whose money is funny. And they never learned how to manage their money. And it's painful, because they're still trying to learn some fundamentals that we should all learn very early on. I not only have you know, my primary home, well, my wife and I between us, we have two homes, one in DC one here. But we have you know many investment properties. And it's a great way to diversify your own portfolio, you got to start with start with one property and go from there. And when you're young, there's a lot of I think in almost every state in the country. And on the federal level, there are first time homebuyer benefits, you can get lower rates and things like that. So there are no excuses, the informations available, but you got to take the time, and it should be taught in K 12. school so that everybody learns it, know why we don't teach it. The fundamentals of you know, you should think of your own life as a balance sheet. And you should have some assets and you should in your assets should be worth more than your liabilities. And that's the difference between those two that tells you what your net worth is. That's the most basic I can make it but that's how to think about it.

Kimmiko James  58:20  
Yeah, I read that in Rich Dad, Poor Dad.

Heather Hiles  58:25  
educating yourself don't Yeah, yeah, I

Kimmiko James  58:27  
know. The last question of advice I have, and this could be lightning round, I guess. Okay. Okay. Do you have any advice for black founders looking to raise capital but are struggling to even get their foot in the door to begin with their foot in the door? Meaning maybe they don't know these investors? Maybe they try reaching out, they get ghosted? Maybe they try applying to these programs and still get ghosted or denied stuff like that.

Heather Hiles  58:51  
Okay. Yeah. So there are, I would look into pitch competitions and incubators, just to get started for will the caveat morning I have is I've seen too many entrepreneurs who are living on the revenue of pitch competitions instead of actually actual customers. And that's a problem. So it's a good way to get started. But it is not an end destination unto itself. And what I would say is that, first of all, there are a number of black investors who are holding themselves out there to be accountable to us and to investing in us so we should be knocking at their doors a lot. And I'm thinking of the great work that Keyshia cash does that impact America. I'm thinking about Arlen Hamilton at backstage capital. I'm thinking about Mac ventures. There are a lot of lot more funds coming out every single day. So, so there are those folks, but there are also a lot of angel funds and venture capital funds who are saying in They're being told they need to be more accountable and recognize more diversity in entrepreneurs. So we should be going to top tier VC funds, we should be continuing to knock on their doors. And if they're not responding to us, we should go on, you know, some of the websites that that ranked VCs and we should share the information that these people are not interested in seeing anything from black folks. So be aware of them, don't waste your time, we've got to be more transparent, share more information amongst ourselves. And what I would say is any entrepreneur is going to hear, you know, 100, nose to one, yes. If you're not persistent, and you're not willing to be persistent and tenacious, you're not really an entrepreneur. It's unfortunately, it's just one of the things. It's one of the traits you have to possess in this society. So if you're not that person, and not everybody, I've been told 5% of any population are actual entrepreneurs. If you're not that person, there's no, there's nothing wrong with that. But it means like, maybe you should work in a company where you can be part of an entrepreneurial group or a startup without having to be the founder, because then you don't have that pressure.

Kimmiko James  1:01:13  
Solid advice for myself as well. Thank you for coming on. Heather, I really enjoyed talking with you, and just learning more about you. And yeah, just thanks for sharing all these value, valuable advice that other people are gonna love as well.

Heather Hiles  1:01:26  
Okay, well, thank you. It's been a lot of fun. Get in touch.

Kimmiko James  1:01:30  
Yes. Where can people find any of your socials, your websites? Or if they want to find you? How can they do

Heather Hiles  1:01:37  
the best site right now I'm about to put up a website soon. So if the if you got any listeners out there who want to work with me on that, we could work, we can talk about that. But right now, and probably the best way to reach me is through LinkedIn. I definitely track and communicate with people there. Also, if you looked at look at my LinkedIn influencer site, I'm going to start starting the New Year, start posting a lot more again. And so you can kind of see what's what's on my mind, but I'm working on that kind of stuff. But I should have a website up sometime. First Quarter next

Kimmiko James  1:02:11  
year. Yeah, same here. Thank you again for listening to this episode, The Black enterprise network podcast. Join me in the next episode in which I'll be joined by Whitney Griffin, a software engineer at Microsoft and social entrepreneur. She shares how she went from wanting to be a pre med student to a computer science major at Howard University. And she talks about the different ventures she's worked on. See you that

Heather Hiles Profile Photo

Heather Hiles

An expert in technology, learning and talent development, with a 30-year track record of creating and scaling nonprofit and for-profit organizations that have improved millions of lives. Heather is a founder of SFWorks, EARN, The Hiles Group, Pathbrite, and Calbright College.