“We also don't have tons of data sets that get as granular because we also have a problem with funding black research. And when you look at black think tanks compared to others, the funding is always just disproportionate. And so without that, that research or without the access to deep and granular research, how do we truly know what's going on?” -- Sherrell Dorsey

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ROB
Welcome to Disruption Now. I’m your host and moderator, Rob Richardson. With me is… honored to have Sherrell Dorsey with The Plug. She's been a person I’ve looked up to, admired, and she has been in the black innovation space before it was popular to be in the black innovation space, really focusing on data and contextualizing the experience of the black innovation economy, really focusing on disrupting the narrative about who gets to be called a genius, who gets to be called an expert in tech. You know that a lot of black and brown people are that, we just don't get the credit. We don't get the recognition and that's why The Plug is needed. That's why she started it.

And then she also has a new project that I’m very excited about, her podcast -- I’m a fellow podcaster. Welcome to the podcasting space now -- the “Clark Street Project” which is named after where the Associated Negro Press started on 312 Clark Street in Chicago. -- Sherrell, welcome on.

SHERRELL
Thank you so much for having me, excited to be here.

ROB
Well excited to have you here. As I said, I’ve done a lot of these interviews in person but now we don't do that as much. Thankfully, I was already doing virtual interviews, too, and I look forward to those. This is our first time meeting virtually. We've talked over the phone so it's great to at least kind of see each other via video, get to know each other and I look forward to further developing the relationship.

I’ve looked at your career. It's very interesting. Sherrell, you have a very just broad experience. You can't really pin you in really one place, right? You've been a coder. You've been in marketing. You've been in fashion design. You've gone to Columbia. I’m like, “Okay.” To me, you have all these pinpoints that somehow connect to what you're doing.

So as an origin, I’m kind of curious… one of the questions I like to ask people especially with somebody with such a very background as you, “What did you want to be growing up and what do you want to be now?”

SHERRELL
That's such a great question. I think initially, I really wanted to be a producer of Broadway shows.

ROB
Interesting.

SHERRELL
Growing up, I was really into the arts. My mom was the person that always had us season tickets to the theater and ballet and what have you. And so between learning coding and computer networking, I was also in dance -- mostly tap but also some other art forms.

I initially went to New York City for college because I was part of a tap company there and so I thought I’d get to Broadway, I’d be producing plays, what have you. And just along the way, you start to grow up and your world gets a little bit bigger as you start to experience it.

I always knew that being an entrepreneur and having my own company was going to be the thing. I had always been a huge writer. In college, I really got to flex some of those skills. Blogging became a pretty centralized platform and that's really where I kind of started to hone in on being a storyteller and trying to figure that part out.

So I kind of fumbled my way through PR and marketing and working for different fashion companies and designers and just really enjoying learning the sales and marketing process of how you build a brand and how you build a story around a line. And I think all of those skills were super imperative and have been super imperative for my work today.

ROB
Right.

SHERRELL
I went to the Fashion Institute of Technology. I studied international trade and marketing for the fashion industry. And what you learn in fashion is the feeling that people get with design and how design dictates history. It dictates movement. It dictates who we are throughout time.

We select things and [indiscernible - 04:22] one of the best forecasting libraries. So we're testing the colors and trends that were going to be popular for the next year or so. It was very, very industry-focused in terms of the professionals who would come to our school for research.

As I look back on that experience, it has this deeply humanistic element to it that I think helps you in business overall, is like having that intimate understanding of your customer and how they feel about your product or your service.

ROB
Well how do you focus on that? I think people like to say that they are focused on their customer. I would argue most people are not. They get in their own brain or they get in their own way of what they think is the right thing to do.

I had Jewel Burks Solomon on the show and she said, “You have to fall in love with the problem, not necessarily the solution.” And as entrepreneurs, our labor of love becomes what we've done. But sometimes, if it's not in line with what the customer or the problem we're actually solving is aligned with then it doesn't get there. How do you keep yourself focused on, I guess, who your user is and having empathy for their situation? How do you keep yourself internally focused in the business that way?

SHERRELL
That is such a great question. With The Plug, The Plug truly sets itself apart in being a very niche-focused space. It is reporting on the black innovation economy and really looking at trends and observing data and information and insights, really about where we're going.

This morning, I did some writing on just why data matters and I think that data has been highly oppressive for us for decades.

ROB
Absolutely.

SHERRELL
We’ve told us so many different--

ROB
Speak more into why data is a problem. That's one of our questions but since you got to it earlier, why do you think it’s a problem?

SHERRELL
Yeah. I had a moment where it always feels heavy when we hear about the deficit, when we hear about our standing across health, education, housing, transit, food access, outcome. It’s across the board. We didn't have this 400-year head start. We didn't have infrastructure, policy or resources that worked in our favor and so we are dealing in the aftermath of what systemic and institutionalized and government-sanctioned racism looks like.

ROB
Yep.

SHERRELL
And it's hard and it's heavy. It's not that it's not true, I just think that there's some incompleteness.
ROB
Absolutely. I like to say, Sherrell, is that… I’m sure you've heard the saying, “Numbers don't lie but liars use numbers.” And how you use numbers, how you use data, we know data was used to say that black people weren't as smart; black people couldn't do certain things. It still is to this day how data is used, how it's presented. It paints a narrative which will fit into the overall construct that we don't do things a certain way or we only fit into certain categories.

That's why I think when you really talk about data being so important and combining it with media, I mean I think that's where we really focus on changing the narrative which I believe is… That's what disruption--

We're about changing the narratives and the constructs around the black and brown experience. That's what we do. And I think what you do, better than anybody I’ve seen, is use data to tell that story.

And I’ll tell everybody, I’m a subscriber. I think everybody should be a subscriber because we have to get in a mindset as a community to support each other early on because I know a lot of people look at it, “Well why should I have to pay for news?” It's really simple -- because there's not any news outlet that's going to report on us unless we pay for it and it has to be done.

SHERRELL
Yeah, in a vigorous way. I think the reality is that we've always set ourselves apart. I love what you were just saying earlier or just asking the question on “Knowing your customer.” And I’ll be honest, I think that building The Plug truly was a personal endeavor for myself because I was trying to synthesize the conferences and the people that I was meeting and going to.

And I had never really set out to create a platform. I just want a daily tech newsletter that talks about the black and brown folks in tech and ideas that I’m seeing and I want to pair that with some of the external freelance writing I’m covering for the rude and fast company and black enterprise. And I want to make it robust and smart and interesting and not just kind of this copy and paste or fluffy narratives. I want to get… Let's go in deep.

ROB
Yeah.

SHERRELL
And even now, the level on reporting is still very high but I’m looking at like, “How can we be even much more observational?” I think, too, when it comes to data, there's a lot of databases we had to build ourselves. We built the first database on black-owned coworking spaces. We did that in 2017-2018. But to think about the fact that no one ever asked who are the operators of coworking spaces, that happened to be black. We never did an examination of that.

And I think it's truly indicative of the fact that we also don't have tons of data sets that get as granular because we also have a problem with funding black research. And when you look at black think tanks compared to others, the funding is always just disproportionate. And so without that research or without the access to deep and granular research, how do we truly know what's going on or what's being measured? I mean we kind of have things in a macro level. And I think there's power in some definitive stories. So I’m thinking about these things.

And like I said, I was doing some writing on this -- just some personal writing on trying to work out why is this part of the storytelling significant? And even as I’m starting to read the biographies of black engineers in the ‘60s and ‘70s who sold their companies, I’m like, “Why am I just now learning about these people for the first time?” Actually, I have readers that send me books and materials and they tell me, “Hey, I just read this. This seems right up your alley.”

And I just think about the narratives that we miss when we don't have proper data highlighting our accomplishments as part of the narrative of what's happening in business society and the history of successful entrepreneurship outside of kind of the usual cast of characters.

ROB
To that point, before you finish, it makes the point that because of the regular cast of characters, whoever that might be, it's usually seen as the anomaly and that's not true. It's just a few people you know about. And we have to, again, use the data and also use the power of journalism to make sure people know the truth that this is something that you can do, that others have done. It's not a one or two or three or just a few people. There have been a lot of people who have made it under harder circumstances. Is there any particular story that sticks out to you that comes out at the top of your head that really just motivated you and say like, “Wow, people really need to know about this story and this data”?

SHERRELL
We actually had a data fellow this summer work on pulling together database of black women who have had successful exits of their companies or companies that they have represented and we did a very strong data visualization around them -- what year they sold their companies and their company name -- a very basic infographic and then matched with the actual database.

And it occurred to me that I, personally, can name a ton of white guys who sold their companies and made millions to billions of dollars but when I look at black folks in the same level of case study, it's really hard for me to do that in this industry in which I work in particularly in the technology space. I’m not talking like beauty brands or things like that. I found that I had a problem with that but I also understood the power of visibility which is why the data visualization is really important.

And it was important for us to put these women's spaces into the data visualization and not just like their names so that as it circulated across the internet, we saw that these black women across the spectrum looks like us in our community and that we knew their name in perpetuity around the companies that they sold.

So for me, I thought that was significant because, again, I think we have podcasts where we listen to entrepreneurs who have built these massive entities. And essentially, they control almost our total way of doing things, right?

And I think about how little in the mainstream, I suppose, we ask the same kinds of questions to entrepreneurs that are coming from our communities that have been wildly successful. I want to say maybe the news attention started to dig a bit deeper in terms of its sources. We have so many reporters now that follow our work who are at major publications who are now like, “Oh we want to start interviewing more diverse [voices - 14:14].

ROB
Of course, yeah. But you never have to worry about it because it's never going to be their focus. It’s because it's popular to them right now because--

SHERRELL
It's part of the climate.

ROB
Exactly.

SHERRELL
It’s hard. It’s grappling with it--

ROB
It’s the flavor of the week. That’s what it is -- not for us but for them. Go ahead.

SHERRELL
Right. We go through these cycles. So I think when I decided to take The Plug into the direction of, “Let's get some strong original reporting. Let's build out the subscription-based, information-based products that has an emphasis on data to set ourselves apart from anything that black tech media was doing, that traditional tech media was doing,” my goal here--

And then today, I was listening to this podcast with Seth Godin. He said, “You know, you're not for everyone. You're for someone.” And I knew that for me, it wasn't about, “Let me build a site that gets millions of views and clicks” but more so, “How do I build an intimate community where we can have deep discussion and conversation?”

ROB
And a variation of that saying you said is, “If you market to everyone, you market to no one anyway.”
SHERRELL
Absolutely.

ROB
If you're trying to make your goal to reach everybody in the world, you'll probably end up reaching no one anyway. So that's how I feel anyway. Go ahead.

SHERRELL
Yeah, absolutely. And I think that it troubled me for a while because it's like, “Oh man, am I missing the boat here?” And the reality is that being consistent, I built up a really strong audience of people and folks who are executives and leaders and decisionmakers and part of governments who are making big choices around business and where they're making investments to support stronger and more diverse ecosystems.

Daily, I’m just challenged with, “How do I provide value to these people who will go into their offices, virtually or physically, who are going to be at these conferences and they are going to be making choices or helping to persuade the choices of people who are going to say, “Yes, we will set up a fund in this city specifically for black and brown founders. Here's the data information we've been following over the last year that informs us that this is going to be a great bet” or what have you.

ROB
I’m curious. I want you to finish that but I want to ask you a question that relates to consistency. It's easier to feel that way right now because you've had some success recently. But I’m sure there was a time when it felt like, “Is this ever going to work? How will we…” Or maybe not. You might have had it all together at the beginning. You know, “How can we make sure that this turns into a model where I can not only eat but scale?”

Talk about a moment when it just felt… Maybe it was a low moment. Maybe it was a huge setback. Can you think about that moment and how that has informed you to where you're at now to really help you grow. If there was a huge setback; it was something that didn't go as you had planned because we know every entrepreneur, particularly every black entrepreneur, is having… not “every” but most are having some type of struggle in that in some ways and they can probably learn from your challenging moments and how you were able to pivot from it.

SHERRELL
That's such a great question because… And I’m sure, as you know, in entrepreneurship, we get a lot of low moments.

ROB
There’s a lot of them.

SHERRELL
Yeah, daily, weekly, monthly, annually.

ROB
Yeah.

SHERRELL
I started working on The Plug while I was working full time. So I’m waking up six-seven in the morning, pulling it together before work and you're thinking, “Is anybody reading this? Does this matter? Why am I even committing myself to this?” But for me, it was just like, “Be consistent. Give of yourself. And if something comes from it, great.”

I think in deciding to make it a business, it's hard when you're like, “Okay, if I put this out here in the world, are people going to resonate?” Even from when I dropped the membership and it was just like, “Okay, I got my first hundred folks in the first week” who were like, “I’m willing to pay for an executive level membership--"

You know I think entrepreneurship is part vision and part straight delusion and you just have to every day--

ROB
Some people call it “Faith” but I guess it's “Delusion,” too. [Laughter]

SHERRELL
It's delusion. It's like, “Why would anyone decide to do this? There are so many easier ways to make a living and to show up in the world.”

And I think that for the low points, I don't know that they're necessarily specifically tied to the business. I think sometimes, it is the environment. It's in the way in which you're treated or spoken to or not considered or looked over, and that's what builds up your grit and your resilience. And it's okay to say like, “Today is a really terrible day. I’m going to do what I can and I’m going to come back swinging tomorrow,” you know.

ROB
Yeah.

SHERRELL
The great thing is that you start to have this community of other entrepreneurs and you lean on supports. Every time you don't get into the accelerator or you don't get the funding, an investor says “no” or a grant says “no…” You know, I think now I’ve gotten so many rejections. It’s like, every… you know, announce the wins so you see all the good wins.

ROB
Right, yes.

SHERRELL
And I think at some point, you get to this place where you're just like, “What is for me is for me and it won't pass me by.”

ROB
Yeah.

SHERRELL
And who I am -- and this is what we were talking earlier -- is just about, I fundamentally have had to change as a leader, as an entrepreneur, as a journalist. I fundamentally have had to change because you start to respond and adapt to your environment.

And the reality, if I show up with kindness, compassion, integrity, character, I show up with a true mission for the success of my business and I’m working every day to bring it to, not just a good situation that people admire but something that's going to be excellent and useful at the end of the day, this will help to change the way people work, think, what have you. Whatever the outcome is, the impact is key and important -- that I have done my job.

And everything else is feedback. It helps me to refine my thinking. It helps me to refine my work. Especially if I get a rejection and there's feedback attached to it then that helps me to see, “Here's where my blind spot is.”

I’m a solo entrepreneur and I work with a lot of contractors. I’m making my first hire--

ROB
Yes. I do as well, yes.

SHERRELL
Yeah. You don't get the benefit sometimes of having constant feedback and other people chiming in. You're having to make the best choice that you have with the knowledge that you have right then and there. I’m hiring my first employee this year.

ROB
Congratulations.

SHERRELL
Thank you.

ROB
No small fee.
SHERRELL
Yeah, exactly. As you know, you're responsible for someone else's livelihood and you're responsible for creating a company culture that they can thrive in and do their best work. And you have to continue to step up as a leader.

I don't know if there's one specific moment. I will say that--

ROB
If you don't have a moment, I have another follow-up question that might help with this.

SHERRELL
Yeah. Yeah, this year's definitely been tough. Just mentioning -- we chatted earlier -- a lot of us have lost loved ones.

ROB
Yeah. You and I both did, yes. So how would you responded… This is a good anchor because I have some questions for about dealing with this moment of… You've obviously had some great highs but lots of people are going through, myself included, anxiety in this moment. I’m an extrovert, normally. I think you might be a slash of extrovert and introvert just knowing you a little bit.

SHERRELL
If I could live in a library and nobody, I’d be that.

ROB
A tall tale, yeah. Okay, become an extrovert. Literally, I like being to myself sometimes but I also get energy… You're a writer. I’m a speaker. I’ve been in front of many crowds. That's who I am. And so not having done this and just not being able to travel normally and freely and… These are, I guess, 1% problems. I also lost somebody, too. But they still get to you after a while.

So how do you cope with going through when you go through a rut, when you go through some anxiety or some depression, which all of us, if we're honest, probably are going through somewhat in this moment. How do you deal with that and keep a way to move forward and keeping yourself anchored especially at a time like this when there's a lot of pressure?

SHERRELL
It's a great question. I don't know that I have a perfect answer. I think the things I try to do is commit to myself and showing up for myself. Sometimes, I will cancel meetings that aren't important and try to push them to the next week so I can give myself some breathing room.

I stay committed to therapy. I started with betterhelp.com back in March at the height of the pandemic. I talk to a therapist every week and that is something that I am bullish about. It is a form of therapy--
ROB
That’s smart. I need, too, more. That's something that… And I think black people in particular need to embrace counseling.

SHERRELL
Yeah.

ROB
There is nothing taboo about it. In fact, it's healthy. You got to keep yourself tuned.

SHERRELL
Yeah. It’s a maintenance thing. You brush your teeth every day so that you don't get cavities and gingivitis. For me, it is that moment for myself where… As an entrepreneur, you're always giving. You're always giving to everybody. So this is the moment that someone gets to give to me. So that is my weekly commitment to myself. Some people do bi-weekly. I have friends who… once a month, just do check-ins. It just depends on who you are and what you need.

ROB
Yeah.

SHERRELL
I’ve committed to moving my body every day. I’m a huge fan of peloton right now and just--

ROB
Yeah, Beyonce. It’s going to get bigger now for black [venture - 23:52].

SHERRELL
Oh yeah. I have several friends, we're all doing… My friend is coming today. We're going to do the Beyonce yoga tonight. I’m really excited. But knowing that when I work out, it helps to take out some of that stress and anxiety.

ROB
Sure. I can't stress that enough. Just to point, I religiously work out. It’s not for pure vanity reasons, it's because it actually anchors me. It is more important in this environment where you're home more to do it. Because it anchors me, I’m able to focus the rest of the day. If for by some chance I don't work out, my whole mind and routine is messed up. It’s anchoring.

SHERRELL
Absolutely. Those things are important. You know, a lot of people are into meditation. I am sometimes but… You know, I journal. I read. I love to read the work of other people because they talk a lot--

ROB
What's your favorite? You got a favorite topic, favorite book or two of all time?

SHERRELL
Not necessarily favorite books because I--

ROB
Let's say books you recommend to people, just come at the top of your head.

SHERRELL
Right now, I’m in the middle of reading “Mindful millionaire.” It's just really a resetting of values around how you approach money and management. I’m reading “Proving Ground” -- about the story of David Tarver who was a pretty successful entrepreneur who sold his company years ago, a black guy out of Flint. What else? What else -- a lot of business books like, “Traction, Leapfrog.” Some other things in that manner are right now on the list.

ROB
I know some of these books. These are good recommendations and good recommendations for the listeners. You know, iron sharpens iron. It's always important to know what people are learning and gaining knowledge from.

Talking about anchoring, Sherrell, this has been I think a unique environment in terms of the amount of, at least, talk and attention to social equity particularly around black lives and black equity. I read growing up that there was a lot of impact on your life when it came to social impact activities from your family.

I’m curious about what you think in this moment. We obviously just had an election. Thankfully, Trump lost. So that's the optimistic part. The challenging part is that 70 million people in the United States of America voted for an over incompetent racist and said that was cool. So I’m curious to see what you think the challenges are ahead with your work in media particularly fighting for black equity in the tech space, how this moment informs you and what you think we need to do to position ourselves for the long fight. I have a lot of thoughts on this but I’d love to hear your thoughts.

SHERRELL
That's such a great question because it's something that I’m constantly thinking about and chatting with friends. I think right now like in Georgia where I’m based, we have to really prepare for--

ROB
I’m thinking about moving down to Georgia to help you all work because I’m not… -- Go ahead. For a month, I’m serious.

SHERRELL
Quite frankly, we need these wins in the senate.

ROB
Oh absolutely.

SHERRELL
And I think the two contenders running right now are pretty phenomenal. I think that we have to definitely keep our eye on the prize from a policy perspective. Especially the social media world, and even I think this is true even for the VC and entrepreneurship world, we're all kind of focused on this future projecting and like, “Let’s tackle racial wealth inequality through apps and games and VC dollars.” And the reality is policy and government actions have the greatest spread of change.

ROB
Preach us the preach. Go ahead.

SHERRELL
And there's not enough venture capital money in the world that can solve for some of the ills that have generationally disenfranchised folks. I’m talking just clean water, not having lead in your home in low-income housing. There are many factors here.

So I think that we have to get as engaged as possible, truly backing candidates that have progressive policies and we know that are going to take congress to task. I think we also have to be very vigilant within our families, about, “What is our family and community strategy? How do we see ourselves sheltering up? Does this mean that we get together and ensure that we are funding and supporting efforts that are helping our community?”

Our kids right now, a lot of them are not logging into school because they don't have a home environment where they can actually get access to a safe place to do school work.

ROB
Or they don't literally have access to enough broadband or internet power to do it anyway. That's also an issue.

SHERRELL
Absolutely. So what are the organizations that we are going to support collectively as groups or as families? I’m not doing Christmas gifts this year. I’m not traveling for Christmas this year. I usually go home to Seattle but… You know, instead of traveling, I’m going to ask my family, “Can we make a family-sized donation to the Human Utility project,” which is paying the water bills for folks whose water is getting turned off--

ROB
What's that project called? I haven't heard. Say again.

SHERRELL
It’s Human Utility run by Tiffani Ashley Bell. She's a software engineer.

ROB
I’ve got to have her on. I haven't heard of her. I’d love to have her information. That sounds like great work.

SHERRELL
Absolutely incredible. I mean it's literally stopping water bills from being cut off from elderly and single mothers -- things like that. What are these impact-oriented community, center-oriented initiatives that we can be throwing our money and our support behind? I look at the efforts of A Stacey Abrams and a lot of the grassroots efforts and how powerful that campaign has been. It's just the diligent constant consistent support of these things that are going to be extremely helpful for our neighbors, knowing that if my neighbor does well and my neighbor's children does well, my community does well and I do well.

ROB
Absolutely.

SHERRELL
I think that there just has to be a hyper focus on those areas that are some of the most troubling, from education--

SHERRELL
I completely agree. I do.

SHERRELL
Even from a food access standpoint. I mean the reality is lots of folks has lost their jobs. We still have a challenge because we don't have stimulus checks that have come out to help further support people. Conditions have risen.

So in what ways can we be… Again, being catalysts in our own communities on a local level, even if it's making donations to the food bank or volunteering right now to help with logistics and driving folks… you know, when people were driving people to the polls. How do we do that on a consistent basis where we are ensuring that folks are getting meals -- whatever it is. I think that we can really make an effort.

And I say this to say like I’m telling myself that as well because I’ve been so bogged down in building my company that I also have to take a break and think about, “What is my civic duty and what are my civic actions that are going to make me a better citizen and resident in my community?”

ROB
Yeah. So many great points I want to get to. And after this interview, I want to talk to you offline because I agree with what you're saying. And I do think, actually, an app I’m building right now, it will help do that -- a lot of things you're talking about.

If you don't know my earlier career, I was in all public service. I ran for statewide office in Ohio, so very familiar with everything you're saying.

And I know there's an under-appreciation for the amount of effort and organization we need to have to make successful, sustainable impact. A lot of our focus is often reactive which is understandable. It's protests, which we need, but I tell people, “Protest is one level then you got to get to policy” because protest without policy is… Nothing happens. It’s not changing anything.

SHERRELL
It's hot air.

ROB
It's hot air, right. So it's just that. Sometimes protests can spark the policy but only if we vote. And then to make it sustainable, we need the third component. We need power. And we have to do all these things consistently and that requires organization.

One of my favorite lines is from A. Philip Randolph He talks about organizing. He was speaking of it, Sherrell, in the context of labor and organizing your power there but it still remains the same. He said, “Look, in the banquet of life, there are no reserved seats. You only get what you can take and you can only keep what you can hold. You can't keep or take anything unless you're organized.”

So I think it comes to us now, as a black community, understanding that we have to organize, politically and economically. And the two are not separate tracks. They are very much related. In every community, besides for us, understands that. And I know from my own personal experience running, that we have some ways to go to understand what we have to do collectively because--

You know, when I talked to a lot of my Jewish friends, they understood it. When I talked to my Muslim friends, they understood it. I could say it was a little more challenge -- I got folks there but it was late -- with some black funders. But we have to understand how we invest in each other early. Just like we have to invest in each other in tech, we have to also invest in each other in the political system to really have the systemic effect to change things. So I completely agree with you on that.
And I’d say we got to be vigilant because the fact that a president could be overtly… I mean usually, people would try to pull it back a little bit but people said they were cool with this. And not only were they cool with this, in fact he got more votes than any other republican president in history. So that tells me that they might try these strategies again. We can't just be on the defensive, we need to go on offense. So I completely agree.

SHERRELL
Yeah, I think it's an interesting time because there is power in unity and also realizing that there are people who are okay with the status quo and believe that by you having less that they can continue to have more…

ROB
Correct.

SHERRELL
…even if it's a farce.

ROB
By the way, it's always a farce. I mean we have data on that, right? Have you read “Why Nations Fail?”

SHERRELL
I have not yet.

ROB
Good book for you. It just talks about nations and structures. You're a nerd like me. I say that as a compliment. But it talks about the structure of nations and it really debunks all these myths about, “Oh it's because of our great culture.” No, it's because of the systems and the incentives that are in place. And they happen -- not surprised -- because of history and how they happen.

I’ll just get to the really short part of it. South America and north America is one example. South America, the economics are very different. There's a reason for that -- because when Europeans came to south America, they just went there, extracted all the resources and then put up this state that wasn't very stable. And then when they left, people just recreated that same thing. And the incentives were in place to have not a very innovative culture. And it's very oppressive and repressive.

In north America, even though we have slavery, it still had a lot more independent states. And people came here because they couldn't just make all the Native Americans do all the work. It was a very different structure. They fought back so they had to come here and do the work themselves. And then eventually, we know they imported us as well.

But it was a different structure so they had more independence. They set up a state that was more independent. And of course, they end up fighting back. There's a reason for that over time. And when all that got together, we were economically stronger.

But a point here is very important. The south was always lagging behind the north because of how they treated black people. And because of slavery, it actually brought down the economics of the whole area. The data proves that out.

But the stories people tell themselves that “I am better. I can feel better than you because society places me above you” doesn't help them. It just helps them feel better about themselves but--

We have a lot of work to do, making sure we shape that narrative. And also we don't believe it because… We know even though 80% of black men voted against Trump, more and more voted for Trump and we need to make sure we're not adopting the narratives of the oppressor. I don't know how the hell else to say it.

SHERRELL
I think in general like breeding better candidates is a big task for the democratic as well the republican parties and any independent parties. I think at the end of the day, we should definitely be free thinkers. I mean I don't know which candidates, in general, have been the best for black folks since Kennedy, to be honest with you.

ROB
I won't go too far down as we got to hold on the conversation. The problem is also the obsession with presidential politics.

I ran for treasurer. It doesn't sound sexy but it have the ability to lend billions and billions of dollars, determine where contracts go, make millions for people. But everybody was like, “Well it's treasurer. What do you do?” You do a lot. You're the bank for the entire state.

SHERRELL
Yeah. I mean the same like you said like the board of education, I mean these people make very scathing… I mean I don't know any public-school education board that isn't a very hostile environment in terms of determining the future of schools and systems in a city or a state. And I totally agree with you. I think that the call for us today is to get much more engaged because…

ROB
Exactly.

SHERRELL
…we can't govern through an app. That's just not what would change us because we--

ROB
No, no, no. An app, it can only work if it's an extension of the real work, right? The reason why--

SHERRELL
Yeah. It should be supplemental. It should not be the primary source for us in which to engage in our political system or our civic duties. I think there should definitely be a level of complimentary opportunities there but there's also “Roll up our sleeves and let's get to work.”

ROB
Yeah.

SHERRELL
So I think this is a really interesting time. I think that we're looking at leadership from folks like Stacey Abrams and all of the other indigenous folks and Latin women and all of these other groups of individuals and organizers who've been on the ground really, really catalyzing people towards showing up at the polls.

ROB
Yeah.

SHERRELL
Like I said, I feel like watching this moment in time and looking at where we've come from for the last four years, I have a greater sense of optimism. But I also feel a greater burden of responsibility to also ensure that I’m not just out here making conjecture and critiques but that I am also engaged in some form or fashion on an individual level as well as how I show up in my current city where I live as well as how I’m sharing and informing my friends around the country who are also looking to get much more mobile at.

ROB
Yes. I’ll move on because I love this point so much. I would say we can't solve the problem through the apps particularly the apps that are in their current form but I will say there needs to be more technology that is geared towards solving our problems and social impact, which hasn't been.

We haven't really used data, for example, to go after fixing the criminal justice system. We haven't used apps in terms of really focusing on candidates the way you say that they are and highlighting the races that can have real impact and make people say, “Okay, can you give to this candidate… this candidate going on…” I think it's both end and we have to get on the ground, work with people and then we have to make sure that we use technology to supplement that.

But that's not the focus of any app out there right now. The apps right now, they’re media. Their focus is to make money. And of course, people have to make money. You can make money a lot of ways. But their focus is just to make as much money as they can. And that focus has just been on, “How do we sell ads to people,” not, “How do we actually connect people to have impact?”

This is not their model. That's not Facebook's model. I mean Twitter, as progressive as they are, that's not their model. Their model wasn't that. So we also can't expect a model that was never created for us to do that to actually work. I mean that's my only real point too there.

I have one origin story then I want to talk about the origin question again then I want to talk about the podcast and then end with a few rapid fire questions I’d like to ask.

You had a lot of experience here -- getting to The Plug, getting it to be successful and lots of other journeys along the way as we talked about. I’m curious to see what you would tell your younger self now. Like what advice would you give your younger self, one, and what advice would you ignore?

SHERRELL
I would say, “Keep doing the reading” -- just really, really immersing myself. Like you alluded to earlier, I was a nerd. I was going to all of these other colleges and getting the free student pass to go to conferences and policy discussions. What I realized back then is that I wish that I would have just continued to do much more exploration even through coursework. You know, you're kind of floating a bit when you're younger, trying to determine what your skills are and what your interest is.

I think secondarily, I really wish that I would have had more guidance around strategically planning a financial future, so really understanding how my goals, my dreams, desires and my environment in terms of cities that I decided to live in, how does this fit into the larger narrative of me, creating opportunity for myself and for my family so that I can fully function and build out all things I want to build out and also be a catalyst to investment in terms of like--

ROB
It’s so hard for a dreamer though. I go through this tension, too -- just figuring it out like were you’re just obsessed about making the numbers versus filing the vision. To me, it is tricky. How do you balance that?

SHERRELL
I’m working on this thing called “Giving myself grace.”

ROB
[Laughter] How’s that going?

SHERRELL
It’s a hard thing, I think, especially you feel like, “Why didn't I know that” or “Why didn't I spend more time on this” and you're constantly reevaluating yourself. It's part of like trying to get better, trying to challenge yourself.

ROB
Sure.

SHERRELL
You start to surround yourself with people who are really excellent at what they do and you see how far you have to go. When I give myself grace, I’m showing up every day. I’m consistent. I’m learning. I am prioritizing this, this and this as part of my day. I’m establishing and strengthening my values. I am ensuring that I am best representing my truest and my highest Self. And every day might look different, right? Everyday might look different.

ROB
Right. Every day will look different.

SHERRELL
It will, absolutely.

ROB
It never goes the linear process we expect it to be.

SHERRELL
Absolutely.

ROB
I never thought I’d be doing what I’m doing now. I had a very different path that I thought… Still doing the same work but it's in a different function.

SHERRELL
Yeah. And then just committing yourself to being a lifelong learner, to being okay with changing your mind, with having different assumptions, even giving other people grace. I think that I can be highly, highly critical because I have this thing… I don't like when people play in my face that's why I’m always like, “Show me the data.”

ROB
You don’t like when people play in your face you said?

SHERRELL
Yeah.

ROB
What do you mean by that?
SHERRELL
I think about… especially when it comes to this narrative of black folks in funding and in VCs or what have you, I think that there can be a lot of showboating, a lot of--

ROB
Do you mean from larger corporations and entities that pretend like they're doing something and just want to just say “Black lives matter” and then--

SHERRELL
Yeah -- entities, corporations, individuals. I’m like, “Show me the checks and balances there.” I think that--

ROB
Oh yeah. You know, what, a point you made… Sorry to interrupt you but it sparked another question I wanted to bring up. And you and I, we are aligned on this in the universe completely about diversity and inclusion and what they're--

I’ve said on the show, the revolution will not be brought to you by diversity and inclusion training. It's not happening, right? I mean that's not the method to really create a sustainable difference but that's been the check box approach to things without any real measurables or really any real outcomes. What do you see needs to happen in that industry to make it real? How do you want to challenge that industry and disrupt it?

SHERRELL
I just think that there needs to be more accountability and transparency. At the end of the day, I think that it's not enough to have great platitudes and to just kind of designate people the king or queen or this messianic figure of saving black capital. I think we just have to have much more nuance and honest conversations about the industry itself and its behavior.

At the end of the day, I don't care if you think I’m the smartest person in the room. All that stuff to me is distraction.

At the end of the day, I want people who want to just help build super dope businesses.

At the end of the day, all this other fodder and stuff, let's skip that. Let's skip that. Let's just go build dope things and then moving on and creating great things in the world.

ROB
People who ran an organization, when I get to whatever that is, had I won the treasurer's office, we weren't going to have a diversity and inclusion office. I didn't need it. I was going to be the leader and just hold everybody accountable to make sure that they're doing it because it's in the best interest of the state and it's the right thing to do. You're right -- it should be part of your culture, not--
Often, I’ve seen there are some good well-intentioned D&I directors -- I am sure -- but often, they don't have any power, money and it's just platitudes like you said.

SHERRELL
Yeah.

ROB
“Clark Street Project,” let's get to that a little bit. Tell me about the Clark Street Project -- what that narrative is about and what looks like success in terms of the impact you want to have with the Clark Street Project podcast.

SHERRELL
So the Clark Street Project is really an exploration of early black internet entrepreneurs as well as black journalism -- what does that look throughout history. Claude Barnett started the Associated Negro Press in 1912 and it truly was an interconnected network of black-owned news publications -- about 100 of them or more across the African diaspora. The significance of that was super critical because--

When I learned about him, I was in J-School. I didn't learn about it in class. I actually got a book from a professor. And I had no idea that the Associated Negro Press existed.

The idea behind the project truly was about, “What has the evolution of black journalism looked like? Why has that been significant to the way in which our businesses are covered?” And then also sort of, “What are the challenges or the opportunities that have existed when black journalists have also been able to do work around covering black folks in black business within mainstream spaces?”

I think that sometimes we lose the opportunity to honor black journalists that have been on the line telling our stories and bringing visibility to our work as well as our genius.

And so it was very experimental as an opportunity. We got a great grant from the News Integrity Initiative out of the city -- the University of New York Journalism School, the Craig Newmark School of Journalism.

And I worked with some dynamic producers and creatives to build this together. We had an opportunity to talk to black researchers talking about the effect of Black Tech Twitter, that being such a dynamic media platform for discovery and for learning, talking to folks who built Afrolink and Afroman, the early days of AOL Black Voices. You know, we don't get to hear those origin stories because we're always focused on like the Googles, right?

ROB
Yeah, exactly.

SHERRELL
But there is Afrolink. We were out here.

ROB
I remember BlackPlanet. I don't know how old you are but--

SHERRELL
Yeah, BlackPlanet.

ROB
Okay, good. You’re in my range, okay.

SHERRELL
I was in high school on BlackPlanet. Yeah, I was in high school on BlackPlanet. And the significance of these--

ROB
The pre-Facebook, that was just for black people, yep.

SHERRELL
Absolutely. So we wanted to just really shape this as part of this dynamic history around entrepreneurship and journalism. I’m excited about the possibilities for the second season. We have four very strong episodes.

ROB
You do? I’ll check them out. They are great.

SHERRELL
Yeah.

ROB
Agree. Everybody, go check it out. Everybody, listen to the podcast.

SHERRELL
“theclarkstreetproject.com,” absolutely.

ROB
What do you think the future… and I got rapid fire questions. What do you think the future of black media is? They've obviously had lots of challenges. I think there are a lot of reasons for that. I hear some people blame Facebook and the social media atmosphere now. My perspective is also some failure to pivot and innovate, too, and I know this dealing with--

I mean I’ve tried to get black radio because I had a radio show… It must have been seven years ago working with radio. One, I said, “Here, I will start a podcast with you. Let's do it digitally. We can do it.” Mm-mm-mm… I mean now everybody has podcasts. I think there's a lot of reasons for it. But what do you think has been the reason for, I guess, the decline lately and what do you think the future is in terms of maybe more opportunities in the horizon there?

SHERRELL
Journalism is hard. Yeah, the major platforms have sucked up -- most of the ad revenue that media was getting before; of course, black media getting a lot less in comparison to some of the larger publications.

A slowness in terms of innovation, I think, is definitely a challenge. It's such an old industry and so you do have more of an old guard for some of the legacy publications. I know there's that frustration of making that transition.

I think lots of legacy news before they got the talent in to help lead into a new direction just had a hard time with the pivots and really understanding how technology is affecting media. So I don't want to say that it's just a black media problem. I think it's--

ROB
No, it's a media problem, definitely.

SHERRELL
Absolutely. So in terms of future, I think at the end of the day, you have these new entities that have popped up.

ROB
Like you. You’re one of them.

SHERRELL
Yeah. Absolutely, myself, tribed out of Chicago. Blavity and that team and Morgan DeBaun, they built something super incredible a few years ago that continues to thrive today. I think that there's always going to be a new world order. And I think that, yeah, some of the legacy publications aren't able to make that pivot. It's going to be a tremendous challenge.

I think for like black newspapers, just your traditional newspapers, they're finding and attempting to make these transitions into digital. You have like the Facebook Journalism Project who we've gotten a grant from as well as Google News Initiative who are working and retraining newsrooms and teams. So I’m really hopeful about these social media platforms coming in to provide their expertise to help some of these newsrooms to make transitions because at the end of the day, it's still necessary.

There are a lot of folks thinking about the New York Amsterdam News – one of the oldest black publications in New York City -- they cover Harlem. They cover Inwood Park. These are neighbors. And stories that they're talking about in their local communities, I would hate for that to be lost.

ROB
Yeah, local news is such a challenge right now, too. You're so right. Well we can have a whole session on that. Maybe we'll have another podcast on that.

Let me get some rapid fire questions in here. If you had a committee, living or dead, of three advisors to advise you on life, business, personal -- they can be living, they can be dead -- who would these three people be and why?

SHERRELL
That is a dynamic question. Dorothy Dandridge.

ROB
Okay.

SHERRELL
I’ve always loved Dorothy Dandridge. I feel like she was gone too soon.

ROB
Definitely.

SHERRELL
I just think she had this powerful finesse as a performer, as an actress -- so definitely her. Who else? Would definitely love to sit with Oprah.

ROB
Oh yeah, Oprah is always good.

SHERRELL
Yeah. I just find her to be absolutely phenomenal on so many different levels particularly in business. Who else? Gosh. You know, I would love to have a sit down with Seth Godin. I think he has incredibly interesting things to say. And I think that the simplicity in which he thinks about business and art is truly compelling and focused and so it would be great to break bread with him.

ROB
All right. Two more questions very quickly. What's an important truth you have or conviction you have that is controversial that very few people might agree with you on?

SHERRELL
Oh gosh, that's a great question. You don't want to incriminate yourself. [Laughter] I will say something that I think might be relatively controversial. I don't think we need to continue to have these black people programs. Especially following the George Floyd murder, I feel like there's a lot of these programs that are so geared toward, “Let's set up this temporary illusion of helping black people.” I was talking to someone the other day and I was like, “It feels like these are just the equivalent of welfare programs. Instead of saying, “Let's just use our traditional fund or our traditional mechanism and ensure that we are funding more black folks--””

ROB
Yeah.

SHERRELL
And I look at the people, I think about Impact America Fund who has stayed hyper-focused, had been led by one of the most incredible black women investors, Kesha Cash and Stefanie Thomas and the others on their team, they've just had a commitment to investing in diverse founders from the beginning.

I just think about these other like “Here today gone tomorrow” folks. Why do we always need this kind of separate and unequal mechanism to right wrongs that seems much more performative than anything else…

ROB
I agree.

SHERRELL
….because if these programs are so great and the businesses you're funneling in are so great, why aren't your other investors who are investing in the big big deals also tracking that?”

And I’m not saying that they're not routes for people. They're great opportunities for people. I don't want to disrespect or throw shade on any of the folks that apply to and get into these programs because it is a stepping stone. I just question this ongoing need that we always have to have the separate and unequal mechanism in order to get our foot in the door.

ROB
It's the same thing with the D&I conversation we had earlier. Having a diversity and inclusion person that's supposed to be overall our diversity and inclusion, it never changes anything. And they never really have any accountability or responsibility to easy check the box approach.

To your point, if we're really trying to solve these systemic problems, it requires innovation. It doesn't require the same level of thinking that created the problem as Einstein said.

Final question: You have a billboard or Google ad that summarizes what you stand for in life -- your principle -- what would that say and why?

SHERRELL
“Lifelong learning, transmuting constantly and designing a life that is significant and well-lived.”

ROB
Hey, that’s good. -- Sherrell Dorsey.

Check out our new podcast, “The Clark Street Project.” Also, of course, check her out on The Plug. Sign up. I’m a member. I also subscribed to the podcast. I want to share the love. She's doing great things. She's going to continue to do great things and we're honored to have her on the show. -- Thanks for coming.

SHERRELL
Thank you so much for having me, Rob. I really appreciate it.

[END OF TRANSCRIPT]