ROB RICHARDSON
Welcome to Disruption Now along with the Global Entrepreneurship Week. I am honored to be here. I am your host and moderator, Rob Richardson with Disruption Now Media.

We have a great panel today talking about entrepreneurship, what it means, particularly Black entrepreneurship. With me is Carlin D. T. Jackson with Wyes David, Ltd. Also with me is Anthony Gillespie of Keen Point Consulting and Jay Williams of the Hartford Foundation. -- Brothers, good to have you on. How are you all doing today?

JAY WILLIAMS
I’m doing excellent. Good to be with you, Rob. And Anthony and Carlin, with you also.

ROB
Good to have you all on. I want to talk to you guys about entrepreneurship. You all are either entrepreneur leaders or have helped support entrepreneurs so I want to really get the perspective of the black entrepreneur.

We know it's tough to be an entrepreneur no matter what. And being black on top of that, there are additional obstacles. There are additional barriers that are unique to the black experience. We want to talk about that and figure out ways to navigate it so we have more successful black and brown entrepreneurs.

Jay, I want to start with you. You've been a mayor. You've been in charge of helping develop ecosystems. I know you were the mayor of Youngstown so shout out to Ohio, Cincinnati here. Give us some perspective on what you think... In particular, I want to say this. If you had to speak to your younger self or when you first started in this process of being a leader, what advice would you give yourself now with the knowledge that you have now and what advice would you ignore?

JAY
Sure. Again, while I’m not an entrepreneur currently, I have spent the past 10 to 15 years of my career helping to build ecosystems for entrepreneurs, specifically entrepreneurs of color whether during my time as mayor of Youngstown or in Washington DC working with the Obama administration or even now here at the Hartford Foundation for Public Giving.

And I do have first-hand experience because my father left corporate America to become an entrepreneur realizing... and would share to my younger self that it is the most difficult, challenging but also, simultaneously, the most gratifying experience that you will probably embark upon. There is nothing more difficult than working for oneself and having to go out and… You eat what you kill. But at the same time, the gratification--

I remember my father telling me as he was leaving General Electric, he said, "Jay, as long as you work for someone else, there will always be a ceiling that you will never exceed and that ceiling will be whatever they set for you. Whatever your title is, whatever salary and benefit package they're giving you, it is always limited by their discretion. But when you go work for yourself, while it's challenging, the sky is the limit. You set your own bar and you continue to exceed that bar."

I think that is what I take away because I was young when he left GE and I thought, "Man…” He's at GE so there's a steady paycheck every two weeks. It was a good job, good corporation. My sister and I... Christmas looked a certain way when he was working at GE and then when he left to go out on his own, Christmas was a little bit differently. At eight or nine, 10 years old, that's how you kind of judge. "How are we doing? What is Christmas looking like?" But I saw his level of satisfaction in what he was able to do. He would often take me along with him on those jobs.

Again, I learned that the ceiling is set by others when you're working for someone else but when you're working for yourself, the challenges are there but the gratification in what you are able to give of yourself takes on a whole different connotation.

ROB
Yeah. Anthony, I know you are an entrepreneur. Can you think about when you first started in this process… I think being an entrepreneur, it's kind of hard to advise oneself because it's just an experience one has to go through. Take me through your experience. Knowing the things you know now, what advice would you give yourself? And then if you heard any advice about being an entrepreneur, what would you ignore?

ANTHONY GILLESPIE
I started down this journey... I mean I worked in industry probably for almost 25 years in a variety of technical positions. I’m an engineer by training, so having that comfort zone as far as working for a company, and as Jay mentioned earlier, having a steady paycheck was always comforting. But at the same time, I always had that urge to strive for more and go off on my own.

One of the things for me, I always dabbled as far as starting up a business, never really leaped over the edge until about five years ago when my position in my group was pretty much shut down within a major organization and I had a choice to go look for another corporate opportunity or actually go off on my own and start my company.

With my wife's urging… She always knew I always had that interest in going and pursuing that entrepreneurial route and she said, "You’ve learned a lot. Why don’t you go ahead and start?"

I really didn't go through a deep process as far as developing a plan as was prescribed in the books as far as developing a business plan. It was really out of the need--

ROB
I thought most entrepreneurs don't, by the way. -- Go ahead.

ANTHONY
Exactly. Exactly. In my case, it was really out of need. "Hey, we got to pay our bills and get things going." And I know a lot of things so I started Keen Point Consulting which really is a consulting firm that works with a lot of organizations to really help them figure out how they can leverage technology assets to drive economic development.

ROB
But if you can't, Anthony... I want to guide the question a little bit.

ANTHONY
Sure.

ROB
Let's get to a point where you... because there are some things you were kind of forced into going the direction that you believe you should have gone at some point, it sounds like. Talk to me about something that you wish you would have told yourself when you first started that you just didn't know, like, "Wow, if I was starting over again, with the knowledge I have five years out…” Can you think of something that just sticks out in your brain like, "Listen, young Anthony, do this or do not do this"? What would that be?

ANTHONY
Well it comes back to the basis. As you're always told, "Save. Have adequate savings.” And that was one of the things that really hit us at that time because personal savings really turns into helping your business grow and succeed. And so having that cash cow... It goes back to "Cash is king." That's the key. I wish I had really listened more to folks who had advised me over the years to have a little more savings on the side because it would have made the pathway much more smoother.

ROB
Any advice you would ignore?

ANTHONY
It goes back to what we're talking about. Entrepreneurship is not as it's described in the books.

ROB
You would have ignored the plan idea. Just forget about that.

ANTHONY
Exactly. Exactly. You don't need a fully developed business plan to start. You just need an idea of where you want to go. [Crosstalk - 07:18].

ROB
Yeah, I think that's a great point.

Carlin, when you think about the process of how challenging it is to be an entrepreneur... It's not something you can plan for but are there things that you know now that you're like, "Okay, had I known this a little bit earlier, I would have been more successful faster”? And is there a type of advice that you got as a black entrepreneur that you think it totally should just be taken in the garbage and thrown out?

CARLIN JACKSON
Yeah. Those are both great questions and kind of two sides of the same coin, if you will. For me, personally, my entrepreneurial journey started as a very young child in school, finding creative opportunities to make money, at the same time, be a help to my classmates. I remember seeing after gym, everyone was thirsty so let me provide frozen packs of drink and make like a 50% margin selling them for 50 cents.

ROB
You really were early. Jeez, man. You have found your calling, brother. You have found it.

CARLIN
Exactly. You know, you take that approach trying to find opportunities. Forward many years later, I’m graduating with my masters and I have a choice to make. I, too, have a background in engineering. I then spent time in a business school and I was like, "How do I utilize my background and experience?" I just decided that striking out on my own, starting my own consultancy, “Theo. Wyes David,” was the path.

Right now, I’m primarily engaged with a newly launched tech startup in the e-commerce space as their technical co-founder. So on two hands, I have experience with entrepreneurship with a services-based organization and actually now offering a product and offering to clients and customers. One is taking on projects whereas the other is kind of responding to the needs of the market and the customers.

You have to have clarity and focus, right? For the consulting side -- I’m sure Anthony, you will agree with this -- understanding what it is that you are and aren't going to do from an offering standpoint. Sometimes, people have requests to build you the moon for $5. Well maybe it's just, more or less, totally outside the realm of… This is what I’m trying to focus on from an offering standpoint.

ROB
Yeah. Carlin, just to interrupt you very quick. A point, I think, telling my younger self… I’m the newest probably in entrepreneurship between the rest of you guys. I only really have been about 18 months in. I would have looked at the importance of knowing the process for how you price things because… That kind of gets to what you're saying because it's very... I mean it's easy to get that wrong -- it's easy to get that wrong. And understanding how much does it really cost you. What are your cost of goods?

You don't need a business plan. You do need to know what your services are worth -- how much time is going to take you to get it and how you're going to scale it -- because if you don't know that, either you’re going to have to spend all your time and you won't make any money or you're going to lose money -- one of the two.

CARLIN
Yeah, you're absolutely correct. It's both pricing, what you're willing to do, but also limiting that scope of those things as well because some requests, no matter how much someone would be willing to pay or what you will want, it might not be a strategic fit for what you want to kind of pursue.

And that's kind of where I was leading with this tech startup status -- understanding what our place in the market is and making sure we own that. You know, it could be very easy to become distracted as an entrepreneur. Maybe you're wanting to pivot or try to take on more than what you really need to.

And then I would say, to answer the second part of that question about advice, maybe to reject or not give too much weight to, I would say as a--

There's already a lot of challenges as minority entrepreneurs and I think one of the biggest traps is to try to fit a certain mold of what it means to be entrepreneur whether it's the way you speak, talk, dress, interact with the ecosystem at large. You might say, "Okay, let me very much fit this very particular shape so as not to rock the boat” -- to minimize my identity almost so that I’m not a controversy in terms of who I am.

ROB
Right.

CARLIN
Right? And I think by focusing too hard on such things can really limit your ability to express why you're unique, why you're creative and why your entrepreneurial path should be a success. I would say that's probably one of the more powerful things you can tell folks to reject as they start their entrepreneurial journey.

ROB
Man, that's a great point -- being confident in who you are and not worrying about, I guess, making people upset because of who you are or trying to fit into something that you're not.

But let me challenge that statement. Let's be clear. It's a world that's not embracing black people being proud to be black or black people fighting for equity, of black people saying--

Even the word "Black." It just now became popular for everybody to say, "Black lives matter." And certainly, we all do a huge congratulations. People could say, "Black lives matter." That was a controversial statement six months ago. It wasn't to us. But for lots of people, that was a controversial statement.

So you're in a world that we, unfortunately, are not the majority in and there are people that have these biases and beliefs. How do you navigate that tension towards not losing confidence in who you are while still figuring out how to survive and thrive in this environment?

Does that make sense, Carlin? I think it's a great point you're making, by the way. I mean the name of the show is Disruption Now so clearly, I agree with you. What advice do you give entrepreneurs that are trying to figure that out in this space right now?

CARLIN
That's a great point. There is, I believe, an article series -- I can't remember if it was Bloomberg or Wall Street Journal -- in the past few months where they profiled an entire list of black and minority workers on Wall Street who kind of detailed their experience at multiple levels, whether you had chairman, the CEOs or daytraders, who basically kind of spoke to this point about navigating their identity in the realm of industry that was very prototypically not a minority.

It's very a complex issue. And it almost comes down to case-by-case basis of saying, "How do I balance staying true to myself with being able to actually have success in this moment" because not every situation is supposed to be one where you trailblaze or where you rock the boat in a sense. But at the same time, we all have that core sense of, "This is my limit and this is the amount which I’m willing to subject or morph my identity."

What I would say is find where that limit is for yourself because I’m never going to advocate someone to have to fight battles that they don't feel they're prepared to but at the same time, I want them to feel encouraged that if they do indeed have a conviction about saying, "This is who I need to be in this moment,” to know that it's okay to do that.
I hope that makes sense.

ROB
It does. Anthony and Jay, I want to get to you. One quick point. What I tell black founders, black leaders, is that when you deal with -- and you're going to deal with it -- racism, when you deal with ignorance, when you just deal with people that are culturally insensitive or don't understand or don't care to understand, what you have to do is have something--

There is more of a burden on us for this and it's just the fact. But we have to understand, when people react that way, it has nothing to do with us. It's their issue. And having the emotional maturity to not react to something at that moment and figuring out, "How do I move forward--"

I give people this example all the time. I was the youngest chair of the University of Cincinnati. There was a lot to that but I’ll get to one point. I’ll say right before they were selecting me to be chairman, I had done everything. It shouldn't have been an argument but it was. I had never ever brought up issues of race but there came a point that I had to ask. And I didn't bring it up like, "You're being racist." That's usually not effective. What I said is, "Why does my process look different than everybody else's?"

I just had a question for what it is then there was a pullback. They're like, "Are you calling me racist?" I said, "I just asked a question. You said "racist."" I said, "Why does the process look different?"”

I became chair, long story bearable, but I had a lot of moments where I had to figure out when to strike. And it's not always the right time to strike. Even if you are "right," that you know that they're wrong, you have to have the discipline to think for the long game.

Pivoting to this moment, Anthony, when you think about this moment right now -- it's for Anthony and Jay. Go, Anthony then I say Jay -- this moment right now that we're in, whatever you want to call it -- the "Black Lives Matter" moment, "Black Equity" moment, whatever you want to call this moment--

I do think this is a unique moment in the amount of attention and time that has been put to discussing issues of black equality, black equity that I haven't seen in my lifetime. What do you think are the risks or the opportunities in this moment right now given this, if any? What do you think, Anthony then Jay?

ANTHONY
I really see it as opening up a lot of doors that typically may have been only cracked or not necessarily opened up at this point. You see, right now, as far as a lot of big companies now, they're pouring dollars and they're interested in investing in black-owned businesses. They're starting to help as far as create capital funding to support black-owned businesses. So the doors are probably opening up wider than what has been in the past and it's just because--

You know, it really comes back to now, a lot of folks who may not either known it or they weren't willing to acknowledge it, that the perceived risk, as far as for black entrepreneurs and black businesses, really, is probably the same as any other business. So that's really opening things up at this point.

ROB
Yep. -- Jay, what are your thoughts?

JAY
I agree. Rob, I describe this moment almost verbatim the way you've described it -- a unique opportunity that we have not seen in our lifetimes. We are probably all relatively close in age within a few years. We have not seen this in our lifetime.

I think that this moment does provide some unique opportunities for us to assert the talent that is part of the black experience in ways that people are more receptive to. There is a reckoning and an awakening of the importance in understanding the black experience and what we've endured for more than 400 years.

And very quickly, two examples that I have that you were describing is that in 2005, when I ran for mayor, I was the first black mayor of the city of Youngstown. But in doing that, I had to gauge how and when to assert and to react to certain things

In my own town, there were segments of the town that the experts told me not to spend time because those precincts were never going to support a black candidate. I made a decision that I was going to go anyway because I wasn't going to give them an opportunity to say, "He didn't ask."

And while I didn't win those white precincts, I did well enough to ultimately become mayor of the city of Youngstown. But along the way, there were some people who made it very clear that I and my type and my supporters weren't welcome, whether those supporters were black or white.

Now fast forward to where we are now, as the president of a large community foundation, I still struggle with that because... I’ve been president here for three years. When I started, I had a much different style of hair -- more conservative, low-cut fade. And I’m on some boards where people got to know me. But then over the last year and a half, I’ve let my hair grow out and now have a hairstyle that is certainly more communicating my ethnicity.

And I had an individual who I sat on a board with, look at me, who hadn't seen me for about five or six months but had known me and he came up to me after the meeting, he said, "Hey, I haven't seen you in a while." He said, "When I looked and saw your hair, I asked myself, "Is this a guy I would trust to run a billion dollar foundation?""

ROB
Oh my god. Okay. Wow.

JAY
And I'm like, "Wait a minute. I’m the same guy I was a year ago when you knew me.” Just because my hair is different, in his mind, gave him the liberty or the comfort to now question… The fact that we're still facing those things, the change in my hair, in his eyes, gave him liberty or freedom to question whether I had the same level of capabilities.

ROB
[It gave him the extra rant in his mind to go to his vice - - 21:49].

JAY
Absolutely. So we still struggle with that. But it goes to your point, I’ll end with this, is that we still have to gauge when and how to assert. But I think this moment that we're in gives us greater opportunity to really assert the talent, the skill, the fact that as black entrepreneurs, as a black culture, there is a great sense of relevance and value that has, prior to this, been devalued, dismissed and people haven't been willing to reconcile.

ROB
Yeah. I agree with that, Jay. I'll give my skeptic part of the moment. I do think this is an opportunity. I do think there is more attention to it. But I also think because of that, corporations and others are very strategic about highlighting this because it is... First of all, it's smart. It's smart. It's probably profitable to do at this time because their base wants it to happen. The emerging… particularly young people and many other people have been engaged in this.

So I believe that black people, black entrepreneurs, leaders in general, need to take the lead in this and don't allow everybody else to determine what it means to have black equity. This is what--

Look, we started Disruption Now and I’ll just tell people we'll have our platform ready by early next year but it will be a crowd investing entrepreneurial platform for us, built for us, engaged for us. We want people to invest and make sure that we are building each other, investing in each other. And then corporations can participate. We want them to.

And go beyond the "checking the box" of diversity and inclusion. I don't want to just hear diversity and inclusion trading. In fact, I don't even think it matters that much. We need to see how many dollars are being spent with black entrepreneurs. “What does your board look like?” Real measurable, not, "Did you host a good event and put up a beautiful report to tell us nothing has changed.”

I think we need to end that type of expectations and really have this moment where it can be used as possibly a third reconstruction and looking at a moment that we can really advance for all of America, I’ll say, because when black America advances, all of America does better.

So what do you think in this moment, speaking of that now, what is the greatest risk? I think I’ve said what I believe is the greatest risk. What is the greatest risk and opportunity in this moment right now for black entrepreneurs or just being a black entrepreneur in general? I’ll start with anybody.

JAY
Well I’ll certainly say I think that there is a risk that the status quo, those who have fought against so long this notion of the value of black lives, the value of the black community could use this moment to further embolden and galvanize and say, "You know what? This is a rising up,” that we are going to turn this and feel more comfortable now trying to undermine, trying to disrupt this consciousness. This is awakening.

We see actively that there are those who are actively sowing distrust, actively being brought to the forefront to devalue even a simple phrase like "Black lives matter" and to turn it into something of a threat. And I think that we have to understand that when there isn't that viral moment that is galvanizing us, that we can't allow this moment to pass, that we have to understand while there's a lot of attention, there's a risk, that we assume that people are always going to be as tuned into and as conscientious as they are now.

ROB
And they won't be.

JAY
And they won't be. So I think that is a huge risk that we become comfortable and complacent or that we rely on something to spark a social and national reckoning when we have to make sure that this becomes as part and parcel as "apple pie," that the value of black lives, that the equity is not a momentary issue, that this is a permanent demand and requirement of this country and not something that was sparked by unfortunate events such as George Floyd or Breonna Taylor or you name it. This is what we expect going forward, period, permanently.

ROB
This reminds me, Anthony. I just got done re-reading the Autobiography of Malcolm X. Towards the last part of the book, he goes over 1964 and all of the things that were going on in terms of the protest, in terms of some violence just going on in black communities because of the injustices that were happening then.

And he made a comment and... Someone asked him about the presidential election at that time and he said... He was talking about Barry Goldwater, that Barry Goldwater was more effective in the current environment in terms of what the person said. But Barry Goldwater was the beginning of what a lot of what we see in the current political environment.

He asked about Barry Goldwater and Lyndon B. Johnson. And his statement was something similar to what Jay said. He said, "Look, I look at it as a difference between the fox and the wolf. The wolf, I know who I’m dealing with. When black people tend to see the wolf, they are in an environment where they know they have to be on guard rather it's just the fox, they're more likely to go to sleep.” Like, "Okay, well maybe things are better now because this one thing happened," understanding that--
And this is my belief, and I could say as a democrat, that at the end of the day, no matter who's in power, they are a symptom. They are not the cause. The cause is systemic and it will take a long-term effort and it will take a lot of engagement on multiple levels both political and economic. What do you see is the risk in this moment? I mean Jay talked about his. I just kind of told you mine. What's your thoughts?

ANTHONY
I definitely would say one risk is also, like you said... You talked about political economic but it's also looking at some of the social risks that's involved. It's a combination of those factors. That's a big area when you look at it as far as some of the social risks. And folks typically look at economic dollars as far as put towards entrepreneurship in businesses as well as the political policies behind it.

There's a lot of social challenges that we have to face. To a certain degree, we have to look at how we're bringing up that younger generation which is going to build that pipeline to be the future entrepreneurs and the future business people. And a lot of those challenges come back to some of the social challenges we face.

ROB
What do you mean by "social"? Dive into that a little bit more. When you define "social," how are you defining that, Anthony?

ANTHONY
I’m really looking at just as far as the philosophy towards really valuing education. We have to continue to--

You know, with “Black lives matter” it’s creating definitely a big opportunity for a lot of our businesses here. But we really have to look at how do we really educate and continue to encourage folks to really get into the pipeline that's going to build our next generation of talent. That's where it really comes from as far as doing that.

ROB
Carlin, what do you think?

CARLIN
Well the answers given thus far have been great so I’ll try to come at it more of a strictly entrepreneurial business angle.

ROB
Okay.

CARLIN
Outside the context of this current environment, one of the aims often for black entrepreneurs is to kind of be understood and perceived as a quality entrepreneur who happens to be black versus you're a "Black entrepreneur."
And to try to make that kind of subjective distinction between those two, to try to manage how others might respond, I would think that in the current environment, there's the risk that maybe you might just be slighted, "Oh that's just another black entrepreneur who, in the moment, has a good idea, good opportunity" and try to actively manage to say, "Wait. No. Whether or not this pandemic [is] going on or whether or not the context of climate is what it is, this opportunity idea stands on its own." That's part of just within the entrepreneurial environment -- finding good allies, good organizations, those with a good perspective on these things.

I think one of the benefits and opportunities of this climate is that there has been an awakening whether it's among venture capital groups or other facets of the industry that are saying, "Let's broaden our perspective on what it means to be diverse, on how we evaluate candidates from an objective standpoint to kind of remove those notions of bias that one even allow us to make that distinction, that for these... Let's say for this accelerator, for these 10 companies, we have our aides but let's throw in some token minority businesses instead of fundamentally changing that pipeline in the first place so that those candidates all feel more of a natural demographic of the populace.

ROB
Yeah.

CARLIN
So I would say just kind of continuing to be cautious and wary of that classification of who you are from your identity standpoint.

ROB
I think you bring up a couple of points that I’d like to dive into a little bit more. One, changing the narrative and the expectations of what it means to be -- well this is kind of really what it means -- to be black-- and then what it means to be a black entrepreneur because the--

The truth is this. Black entrepreneurs and diverse entrepreneurs, overall, tend to be more successful. There's a reason for that -- because they have to overcome more. And they're more innovative because they have to be as we've talked about. So getting people to really understand that, I think, is really, really, very, very important.

And then understanding, as we tackle bias... because I think the hard part of what you said there, Carlin, is that bias, from a system's point of view, we know for you to really tackle your bias, it requires you to have a check and it requires you to do it over and over and over and over and over again because the mind will want to always go back to what it's known.

And I think we have to get in a place where we are there and saying, "You have to do these things if you're really trying to be inclusive," one. Two, "We expect you to do these things or we will actually hold you accountable.” Because I think if we can get collectively there, that's where we have to be because I think people are always going to see, unfortunately, black entrepreneur together.

But what other communities have shown -- Italian community, Jewish community, name the community -- is that they have to work together and then get people to understand that we expect to be brought in for the value that we bring -- end of discussion.

I do think that's really important. But how do we do that? How do we push organizations in the right way? How do we collectively do that for them to go beyond the lip service, to go beyond saying, "We believe black lives matter”? They get funding, oftentimes... I'll very much a “Wait and see.” I’m a skeptic.

I’m an engineer, too. I’m also an engineer, by the way. You can't improve it, as you guys all know. I want to see what your actual metrics are. How do we go about this in terms of making sure we go and push in a different way where we're just not directed to the head of diversity and inclusion and supplier diversity where their job is just to make sure that they have to work within the system?

That's not true all the time. There are some that are going out there and getting it but more often than not, it's very difficult for the diversity and inclusion head to really make a difference because they're not empowered to. I said a lot. What's the thoughts?

JAY
Let me give you one example of what we're doing. The Hartford Foundation for Public Giving is a large community foundation that covers 29 communities in Central Connecticut. We are primarily known as a grant maker and that's a big part of what we do. But we've also recognized, as we've looked introspectively, “How do we begin to change that narrative as a funder?”

And there's always this power dynamic between a funder and a grantee. Philanthropic organizations are, by and large, very well-intended but don't often or enough recognize that they sit in a position of power that grantees and those, whether they be entrepreneurs or nonprofit organizations, are going to respond in a way that they think that the grantor wants them to in order to get resources. What we've attempted and what we are doing is instead of just the grant-making, we understand the need to share power. And right now, I’m defining “Power” as in the wealth that we possess.

We are, right now, going beyond grant-making and figure out, “How do we share the power that we have as a wealthy philanthropic organization to say that we can make investments in Black and Latinx-led organizations who can do things to build the ecosystem in ways that we can't?”

Even as well-intended as we are, we have committed ourselves to that. But instead of us trying to own that space, we're saying, "Let's take some of this power we have” -- and again, defining "Power" very narrowly with financial resources -- “and invest in these organizations such that they now have greater agency, discretion, autonomy to make decisions to build out the ecosystems in ways that have a greater level of credibility and authenticity.”

So instead of just us sort of writing a check and feeling good and, "Look how many grants we've given to Black and Latinx organizations and entrepreneurial support systems," we're saying, "Why don't we take a chunk of this wealth that we have, place it there and trust and know that there is a level of creativity and expertise that goes far beyond anything that we could possess" and see them more as a partner than as an agency coming to us for a grant. So that's just one example of how we're [crosstalk - 36:49].

ROB
I think that's powerful. I really do. Go ahead. I just wanted to say that. I think that's great because that's often been, I think, a stumbling block when it comes to nonprofit organizations or the charitable world. It's seen as a way to kind of… "Okay, we can give some money here" in almost like a paternalistic kind of a--

JAY
Absolutely. You hit the nail there. How do we move away from that savior paternal… "We know what's best. Here's a little money. Go and do well.” And we feel good to saying, "Wait a minute. Here's some power. You know what's best." And these communities of colors aren't looking for saviors. They're looking for opportunity and the same pathways that the majority communities have had for long. So that's how we're trying to even change the narrative in our space.

ROB
Yep. My fellow entrepreneurs, how do we change the mindset within ourselves and what do we need to do there? As I think about it -- you guys kind of hint around this -- we do go through structural issues. There's no question. But then we also have to work to not internalize that too much as a barrier in our mind. How do we go about that? And then how do we go about, I think, making the rest of the community understand how entrepreneurship has to work?

We need to support each other. We shouldn't view other black businesses as a black business with the label “as a black business” and we're going to treat them differently, expect a discount on or expect the worst out of people simply because they are a black entrepreneur.

I’ll say this as a disruptive statement but I still think it's true. I think we are just as guilty of adopting this mentality as we accuse others of being. Difference of opinion there? I mean you don't have to agree with me. What's your thoughts, Carlin and Anthony?

CARLIN
I would say, just to your most immediate statement, I think the fact that it could be made and argue would lend credence to the fact that there are definitely a sizable portion of our community that might hold those views. Of course, each of us, I presume, try to fight that perspective in our own lives in how we interact with businesses in our communities.

But to your point of mindset, I think, if I understand the question correctly, one of the biggest things we can try to advocate for is really a stubbornness, a stick-to-itiveness, just to say that... and whether it's in ourselves or it's just supporting that, in the entrepreneurs who happen to be diverse that we know in our lives, that encouragement to keep after it, recognizing that there are challenges and struggles and things of that nature and saying, "Are we fostering an environment that encourages failure" -- or as we say "learning opportunities" -- to say that it's okay to pursue this path and whether or not you hit a stumbling block, keep on going because of how important it is, that mission to create.

ROB
Carlin, can you think of an example of a stumbling block you had that now serve as a greater opportunity for you?

CARLIN
Sure. I’ll kind of speak a little bit more generally. It was kind of early in my professional experience before really striking out as an entrepreneur, learning how I wanted to navigate the relationships between me and my… whether it's direct reports or me and those above me and understanding--

I'm blessed to come from a great multiculturally-diverse city -- Cleveland Heights -- and then I spent, of course, my educational time at Case Western Reserve University. Through those environments, you build up a certain perspective of how you're accepted and understood. But then when you hit the workforce, the predominating views and perspectives and maybe even biases people had were, up to that point, a little bit new to me.

And I’d say that shock of saying, "Wow, I don't have the benefit of doubt in this situation" or that implicit trust in learning how to deal and navigate with that, I think has helped me out now later down the road when it comes to saying, "Okay, here's how I’ll approach these types of situations moving forward."

ROB
Yep. That's great. -- Anthony, thinking about where we are here, what would you say is your greatest learning lesson from being a black entrepreneur and how would you advise others in this moment to move based upon other things you've heard? What's your thoughts?

ANTHONY
My greatest learning lesson as entrepreneur is “Opportunities come, often times, from unknown sources.” We talked about, as far as sticking to it and being persistent, that leads to opportunities.

For me, as an entrepreneur, my opportunities have come from just sticking to it and then from some unknown sources -- folks that I networked with probably 10 years ago, with a former employer actually turned into being current clients. And actually, as I mentioned, besides wearing an entrepreneurial hat, I work for a nonprofit organization and that was through a connection that I made 10-15 years ago.

I would say, as an entrepreneur, a lot of times, we look for known sources and probably some of your biggest opportunities are going to come from the unknown just by being persistent and networking and really talking about what you do to make those connections.

So that's what I found out. That's been the biggest lesson for me is really sticking to it and really networking and looking for opportunities well and making opportunities off of your connections in your network.

ROB
Yeah. Jay and I can both relate. I’m a recovering politician, I guess, or public servant and so is he. We've both been in this world. He'll relate to this story that I’m going to tell him. It has informed my entrepreneurial journey.

When I ran for treasurer of the State of Ohio, I had to figure out how to raise millions. I didn't know how I was going to do that. Like I could put on my paper how much I can raise and I think it was a couple hundred thousand. I did raise $2.5 million. And here's how it happened. I mean it happened through the same way you guys talked about.

Literally, I would get on the phone for four or five hours and essentially, 90%, no one would answer the phone and 90%, "No." And there was one time where… I called people 50 times. I was very persistent. One person ended up just giving me $12,000. It's like, "This guy has work hard enough." It can be like, "I’m just going to go ahead give him some money." That happened.

And it is true. You have to be persistent. It’s a journey between being persistent and patient because you have to realize that just because things aren't happening right now, they're not going to happen--

This is what I’m going to guarantee. They're not going to happen according to the way you think and it won't happen on the timeline that you think. Some people, it happens for them immediately -- you know, "Boom.” But that's like trying to win the lottery. You're hoping things are going to go like that. Most likely, it, as you said, Anthony, will be just from persistence.

The people that you expect to help you probably won't and the people that you don't expect to help you will give you opportunities and that's why you have to just stay persistent.

But first, you have to know your product or know what you're doing and have passion for it because it is going to wear you out. It is a hard long road. It's rewarding but there are periods that... You know, you spend most of your time in the process and very little in the proceeds and people get a little discouraged in that.

So having that long view and having enough runway for that long view... Because that's the issue, right? There are no shortage of great ideas within the black community. There are none. There are tons of great ideas. There are tons of great entrepreneurs that don't get the runway because they don't have the capital, connections or the resources.

Now that you guys know what you know now and you've been in entrepreneurship for enough years, what resources would you point people to say, "Okay, this is something that, if I had to start over again, I would look up this”? That's my first question. I got one more as we conclude. I’ll start with you, Carlin, because you guys are the entrepreneurs.

CARLIN
I'd tell the power of asking for help both explicitly to mentors or just folks but also of your region and your environment. I’m sure, Jay, you're aware of the wealth ecosystem of support organizations that encourage entrepreneurship. I’m here in Cleveland, Ohio. Whether it's the Veale Institute for Entrepreneurship at Case Western Reserve University, organizations like Jumpstart or even just other key individuals that you know are connected, make sure they know who you are. Make sure they understand what you're working on and they are aware of what your needs are because more than often, these are folks, organizations, who want to be able to help to demonstrate their worth and their value. You never know how far they could accelerate your journey and your path just by letting them know, "This is who I am and this is what I’m working on."

ROB
Yep. -- Anthony.

ANTHONY
Yeah, I would agree with what Carlin said. Definitely, there's a vast ecosystem throughout the state and throughout the nation to support entrepreneurs. One of the hats I wear is actually providing support and counseling to entrepreneurs and small businesses. So I had the opportunity to witness it firsthand on how valuable... There's a lot of resources out there.

And I would say that starting off, first of all, you don't always necessarily have to pay [equal - 47:22] service or a fee to take advantage of the resources that are available. So it comes down to really, as Carlin mentioned, starting off and looking within your local ecosystem for those business assistance, resources. And then there are others that you can go ahead to help expand your horizon and meet the needs and fill the gaps to help you grow as a business.

I’ve seen it as far as myself, personally, having worked with organizations here collaboratively such as Jumpstart, Magnet, other organizations more in the tech, innovation side of things.

But there are also other organizations here that have a business development center supported by the federal government -- small business development centers, minority business development centers. They offer services to entrepreneurs and small businesses to help them thrive and grow. And you don't have to pay for that service and that support.

So I definitely encourage any black entrepreneur or business to really investigate those opportunities because a lot of times, you don't necessarily know. And the information is highly fragmented out there.

ROB
Yeah, it is.

ANTHONY
So talking to folks in networking, that's how you learn how to really take advantage of those resources.

JAY
Rob, if I can add two quick things even as not currently an entrepreneur. You know, mentors are excellent. Allies are excellent. But what I’ve heard other successful entrepreneurs say is beyond mentors and allies, find an accomplice. We think of an accomplice in a criminal sense. An accomplice is somebody who goes down with you. It's like, "We're in this together."

And find a sponsor. A sponsor is someone who is willing to put some of their credibility on the line. A mentor is great who says, "Hey, you can shadow me. Let me show you what I do" but a sponsor says, "Listen, I need you to sit down and talk to Anthony" or Carlin or somebody in the way... They're putting a little bit of their capital or credibility on the line beyond just mentorship.

ROB
Yeah.

JAY
Mentors and allies, I never discount. But accomplices and sponsors, look for those, too.

ROB
Oh that's such a great point. There's a process to getting those, too. You have to be intentional about building relationships. And it takes some time. There is an art to intentional networking that I believe is lost because people have the false belief that… because someone's on LinkedIn, I can just go out and I’ll just say, "Can you be my mentor?"" That's not how you do this, right? There is a process to this.

Can you reach out to people? Can you understand something that they have? And can you add value to their life in some way or can you make them understand that you understand them and their story and that you somehow connect with them? You don't just go out and... I mean you can do that but you're probably not going to be successful, right? You got to have a process.

JAY
That's a goldmine. They say, "Man, that was me 20 years ago. That was me so let me now invest in this person and help them navigate the pitfalls that I experienced." I mean if you can connect on that level, you're absolutely right.

ROB
Yeah, and that’s it. Like I said, there's more access to people than there ever was. But I believe there's a lost art in how you go about networking. Because it's so accessible, people think that you can do it and just reach out.

JAY
Technology can make it too easy, yeah.

ROB
Right. You go out and just, "I'll reach out." I’ve had a lot of success going out and reaching out to people both on Instagram, LinkedIn and Twitter. I believe there's a few reasons. One, I try to understand and research who they are and then make my ass specific to something that they do. So I’m either adding value to them or they can say, "Oh he really understands and did his research," so on and forth or because of my track record. I built up credibility so you can look me up.

I tell entrepreneurs, black entrepreneurs in particular, that you have to understand that you are... I say this all the time, "You are two things no matter what your company is." You are a tech company. I don't care what you do. You are a tech company. You need to figure out how you use technology to scale, to automate, whatever. You are a tech company. And if you're not a tech company then you're not going to be a company.

Second, you are a media company. You have to figure out how to get your brand out and market even if you don't have a marketing department, that you need to know how to use social media, how to engage your core base and to keep in touch with them before you ask them for money or time or whatever. You are already putting your vision, your statement of who you are.

So this leads to my final question. And Carlin, I’m going to start with you. I already know your answer because you kind of said it earlier but I want you to dive into it. What is the most important characteristic for… And Jay, for you, it's going to be a leader but for Carlin, an entrepreneur. As a leader, what is the most important characteristic? Is it clarity of vision which you already said it's going to be. Is it the ability to raise money? Is it knowing how to build a team? I want you to choose one. What is the most essential quality for a founder? What do you think, Carlin?

CARLIN
Actually, one of the last answers I gave was that stubborn confidence, a shakable faith in a mission--

ROB
I thought you were going to say "clarity of vision." -- Go ahead.

CLARIN
Well it kind of leads to that a little bit but it's more or less that you have to be totally bought in and passionate about what you're pursuing. You can't have a reckless blindness about it but at the same time, to not be so easily shaken by the structural issues you might overcome whether it is of a race space or societal space. It could just be fundamental business problems that every entrepreneur, no matter who you are, faces; to understand that the journey won't necessarily be easy. It's going to come with these challenges.

And then have that mindset that if you persist through it, if you continue on that path and that journey and reach the end, whether it's a traditional clinical success or a failure aka "learning opportunity," that... You know, you can't really see that to that end unless you stick with it. And I’d say going in with that mindset ready for battle, if you will, is probably one of the most important qualities an entrepreneur can have.

ROB
I like that. -- Anthony, what's the most important quality?

ANTHONY
I will come back and I would say "Flexibility." It really comes down to being flexible. As an entrepreneur, you're going to reach to times where maybe cash will be a challenge. You may not necessarily have the network to go to friends and family as far as to help support your company. So where are you going to go to find opportunities to keep your business going?

It could be other aspects of running your company. We mentioned as far as the expansive ecosystem here to support your company. You have to be flexible enough to take coaching and work and collaborate with those resources to help you grow.

I’ve realized, over a period of time, as a business, personally, for me, opportunities have come from keeping an open mind and being flexible. I got a project up in the northeast part of the U.S. and it was an area where I knew there wasn't a very diverse population but it was a good fit for my expertise, my background, and bid on that project and actually won. And that's turned into a repeat client that kept me going and kept the business going. So just having that viewpoint.

I think sometimes, we, as black entrepreneurs, will really sometimes feel as if there's not a lot of opportunities there. But it comes from also being open to looking at, "Hey, we have a chance to go ahead and make these opportunities." So being flexible really enables you to take that viewpoint and really help keep your business going.

ROB
Jay, what do you think is the most important characteristic for a leader overall to lead?

JAY
If not "Characteristic..." I think that there are several important characteristics. But one of the most important decisions you can make as a leader or an entrepreneur is who you surround yourself with. It will make or break your company, your administration.

And I say that because I have always sought as a leader to surround myself with people who are smarter, brighter, more talented in their respective area. And as a leader then to empower them to bring the best that they have to the table, to the problem, to the issue, to the organization and then being confident enough in myself that ultimately, I have to make a decision. Who you surround yourself with will absolutely make or break the trajectory.

And being confident enough that you're the entrepreneur or you're the leader but you can't be the best in everything. So get the best financial person. Get the best marketing person. Get the best... whatever it is -- the logistical person. Get them around. Give them every power that they need, ultimately knowing, that when you make that decision as the leader, the founder, the entrepreneur, you're making it based on an informed group of talented people who are better in their individual fields that are ultimately giving you the direction that you ultimately choose. So that's what I would say is probably the most important decision you can make.

ROB
Yeah. That's great. Similar to that, I would say it's "Self-awareness" -- understanding who you are truthfully. Not who you want to be, not who you aspire to be but who you actually are.

One of my favorite authors -- I had an episode on this with Robert Greene -- he views, when you talk about self-awareness, not how you think of yourself but how others see you. And you can really learn from experience. Some of your most difficult experiences can be, "Okay, what did that person do to wrong me? What can I learn from that situation to figure out how I’m actually viewed and how can I use that to be a more effective leader?"

And it goes to your points, Jay, because you're honest about your shortcomings, you're honest about your triggers and then you also know what you stand for and who you are -- so that goes to your vision.

If you have self-awareness, those things come about and it makes things more clear and it allows you to be able to be the leader, to set the vision but then also set an infrastructure that allows innovation to occur because innovation can occur if everybody agrees with you. That's going to lead to an organization that's going to die.

So you got to have an organization that has a constructive rivalry where people can come back, push back, give good ideas and not feel like their ideas are just going to be drowned out or pooh-poohed simply because the leader doesn't agree with them. So I believe that's what it takes.

I want to say I’m proud of all of you. Thank you for all that you've done for entrepreneurship. Thank you for all that you're going to do and much future success to you. Until next time, we'll see you at the next episode. I appreciate everybody coming on.

JAY
Brothers, it's great to be with you. Thank you.

ANTHONY
Thank you.

CLARIN
Absolute pleasure. Thank you.

[END OF TRANSCRIPT]