Sherrell Dorsey on Building The Plug

Jacob: I’ve been following you on Twitter now for a while, but this is the first chance that you and I are getting to have an actual conversation, so I’d like to start from square one. Who are you? How did you find your way to working in media?

Sherrell: That’s such a great question. I like to describe myself as a data journalist, as someone who is just naturally curious about the state of the world, and particularly how innovation can come from anywhere. I’m wholly interested in those who are coming from backgrounds that aren’t necessarily traditional and finding ways to create, build, support, and develop these innovation hubs that are emerging out of the rubble.

I came into media happenstance. I was at first working in fashion and in beauty from a marketing and PR standpoint, and just loved to tell the stories and examine what was happening in the world around me that was obscure, off the beaten path, really looking at these outliers. I made that transition slowly just by freelancing on the side. As I was working for different tech start-ups, I was freelancing on the side and talking about the start-ups I was finding in places like Charlotte or Kentucky or what have you.

Started to map these trends of more founders of color getting access to capital and building these really unique companies that were also providing jobs and going against the grain and the status quo by saying, “Hey, I’m going to opt into building something from the ground up, and not necessarily going the route of just working for a company and potentially just not being seen for my contributions.”

Took that space of freelancing and eventually turned it into deciding to go full throttle in creating a publication that first started off just as a newsletter that talked about what Black and Brown founders were creating against the world. I stumbled into it, but I think, too, just all of my life experiences really helped bring me to this point.

Jacob: I want to spend some time talking about the thesis behind The Plug. Your Twitter banner image says you are contextualizing the Black innovation economy. What does that mean? Why did you feel there was an opportunity with this publication with this specific target audience?

Sherrell: Absolutely. I think that when we look traditionally at media, particularly within business and technology, the conversations and the stories are very disparate when it comes to folks of color or women or other underrepresented folks being covered. There’s either a sense of disparity, it’s either far and few between, or there is this tokenized, magical Black or Brown person narrative that may happen a handful of times out of all of the coverage that traditionally happens within media.

I grew up in Seattle. I took programming and various coding classes and networking administration classes within a program that I was a part of called the Technology Access Foundation in high school. I worked at Microsoft during the summers as an intern. All of my instructors, all of my mentors happened to be folks of color or women.

When I got into the professional work environment, and I was following tech because I just had a natural interest in it and followed business, all of the conversations and the centering were around white guys and what they were building. It was very rarely looking at women or other folks of color who were also doing just as dynamic things. Maybe their companies weren’t as large and as big, but they were very influential.

I think for me, being able to contextualize what was going on, it was going above and beyond not just saying that this person exists, but giving just as much rigor, analysis and attention to examining the work, examining the trends around the work, examining the trends around what this meant on the greater scale and in scope for a community, particularly if they were building outside of Silicon Valley. I wanted to see the prowess of coverage.

Since I didn’t see that in the world of media that I was accustomed to consuming, I decided let me see if I can try to cover this in a unique way. Is there a space for us to do this smartly and also make people care about this person? Not just being a person of color or coming from a background that is not “traditional”, but let’s talk about their work and examine their work and examine why that work matters.

I didn’t know initially if this was something that people would care about or would actually work as a potential and viable business model. Thus far, it has been pretty substantial in terms of what we’ve been able to cover, the databases we’ve been able to build.

I think just coming to the space and wanting it to be more than just surface-level discussions, we’ve built a pretty substantial and unique community I think for a time such as this as business leaders are really starting to question and understand how does diversity, inclusion, and belonging happen within business and within our teams? How do we make it a true priority? I think we were early. I think we’re finally getting caught up here or others are catching up to us.

I knew that what was in the marketplace, so to speak, was unsatisfactory. It was unsatisfactory. I believe that a lot of main newsrooms were doing us a disservice. I also felt that our traditional Black media publications just did not have the resources or the rigor to cover the beat substantially.

Jacob: We’ll talk more about the specifics in a little bit, but you do have a paid membership. Who is the customer of that product? Is it a purchase they’re making personally or professionally? To expand on that, are they mostly small start-ups or larger enterprises?

Sherrell: We’re getting a mix of large enterprises of municipalities, specifically those that are making decisions around how to create the workforce of the future and how does that look from an equity lens or an inclusion lens? We have researchers, both from academic environments as well as from professional environments, that are studying and building products and solutions specifically related to diversity, equity, and inclusion.

We have other reporters who are leveraging our databases to look for Black roboticists or Black researchers in artificial intelligence and really expanding their pool and network of expert sources because 9 times out of 10 when we see quotes taking place, they’re usually from men and, of course, white men.

There has been a nuanced customer base that’s been part of our membership, which is annual as well as quarterly, and includes exclusive access to some of our data libraries, as well as to our exclusive reporting, as well as some of our membership call conversations, where community is able to come together and hear a synthesis on latest research related to Black wealth creation, Black businesses, what have you. Or an innovative leader that’s helping to map out trends that’s related to the industries in which their business is starting to gain some significant traction.

That really is our model. Our customer base, to be honest with you, when I started the newsletter, I just thought it would be other interested Black techies and nerds, and maybe just people who are generally interested in the start-up ecosystem. Then that continued to expand as we continued to be much more data-driven and seeing how decision-makers in these spaces wanted more access to resources to help them think more critically about how they’re approaching start-ups.

I think the other demographic there that I did not mention is we have VC firms who from day one have subscribed and have leveraged the newsletter to find deal flow. There’s never a week where I don’t have a founder say, “Hey, you had made mention of our company and we received an outreach from a firm.” It’s pretty multi-faceted in that sense.

Jacob: As you think about the content strategy for The Plug, what are the types of stories that you do run? Conversely, what are ones that simply don’t fit?

Sherrell: The kinds of stories that we run, we try to be very thoughtful from things like, of course, your traditional this company has raised X amount of dollars and here’s how they’re looking to grow. We try to run critical pieces. For instance, during the summer, during the protests and racial uprisings in those discussions following the murder of several Black people by police officers in various capacities, we started tracking and building out databases and data visualizations on tech companies that publicly made commitments to denouncing racial injustice.

Then when you took a look at their internal culture breakdown, we didn’t see a ton of representation across the board from employee side to leadership side. A sense of accountability in reporting as well.

The stories we try to stay away from are just generally fluff pieces around people that oh, there’s that oh, change the game. We try to stay away from disparity journalism. Things that only talk about Black people being in poverty or not having resources or not having enough capital. I think a lot of those stories have been told ad nauseam. We want to focus on the trends that are not centered on just whiteness and deprivation. We want to be very future forward thinking about what’s possible, who’s gaining ground, why it’s significant, and how it impacts us all.

Jacob: When you started, like most of us who do a newsletter, it was just you doing it on your own. Now you have a team working on The Plug. Can you talk about the team composition of the company? Then to expand on that, you’re rightfully very vocal on Twitter about paying your freelancers fairly and quickly. In your mind, at what point does it make sense to make a full time role out of work that a freelancer was doing?

Sherrell: That’s such a great question. I graduated in the heart of the recession about 10 years ago, and I remember a lot of those full time roles that came with benefits and things like that disappearing in favor of freelancing and gig economy, which I think at the time, we didn’t really call it that, but it was always a hustle. As someone who freelanced following my first job layoff during the recession, I know how much of a hustle it is.

Paying reporters and journalists and freelancers on time matters a great deal to me, because I know what it’s like to not be paid on time and yet you still have to make ends meet. That was one of the values and ethos I wanted to bring into the company. Early on with experimenting and building your startup you are in that experimental phase. You’re trying to figure out if people want to purchase what you’re selling, if you can gain enough traction to build an actual business and make it sustainable. You have to be very strategic about where those dollars go.

In the beginning, it has been being able to leverage others from a contract perspective and people who have other maybe full-time jobs or they are consulting on the side, but being very clear about the distinction of how this person contributes to the business. I still think that freelancers provide a tremendous value and service. Finding and tapping talent and being able to work with them as you grow helps you to really identify, number one, how to be a better leader, how to be a better manager. Then also really defining what level of work do we expect in terms of delivering a strong product and a strong brand.

As we’ve grown and as I’ve been able to raise a bit more funding, bringing in talent for me has really been about where do I want to get to and how do I expand capacity? We made our first full-time offer and a hire who will come on in a few weeks to help lead editorial. That will free me up to continue to expand the team and to invest in some areas that are very critical to our work like research and just general growth.

I think making that choice is different for every entrepreneur. I think that it comes from really understanding your cash flow, understanding what is needed from a capital raising standpoint, and just knowing when you have to begin delegating because the workload is too much and you do not want to compromise the quality of what you’re producing.

Jacob: Let’s jump into the actual business because The Plug is multifaceted, and I want to explore how each piece contributes to the overall business. First, we’ve talked about this, you have the pro membership, which costs $150 a year or $50 a quarter. Can you talk about in specific detail what this product entails and then, because I’m very intrigued with the concept of quarterly and yearly pricing versus monthly pricing, how you came up with that strategy and pricing model?

Sherrell: It’s all been very experimental. I knew that I wanted to charge a premium for our work because I believe that it is high quality. There was the early 2010s or maybe even before where we got into this blog accessible all the time, everywhere. I definitely believe in journalism as a public service. I think once we get into niche spaces and we are looking at creating value for audiences that go and in turn deliver value for their companies, that we have to build a business case, especially around the work and research of what’s happening in Black tech. Really honoring a group of individuals who traditionally have not been seen as critical to the growth of the economy overall.

In terms of pricing, I really looked at others models. I looked at my subscriptions, and who I subscribe to, and what those rates were. I looked at the value of those particular rates and decided I think $150 is pretty standard. Along with that particular package, there’s access to our data libraries, there’s access to our exclusive stories that are under paywall and just for members.

Each month, we have a call with members and someone within industry that can help us synthesize either new reports, new analytics, or even just trends in their particular field to help us just become better thinkers about our work or our investments. Also to showcase and highlight different Black professionals and experts within the innovation economy that we should also be following their work because it’s critical to those next steps and spaces of where we’re headed.

I decided to differentiate between the quarterly, the annual, specifically from the monthly because we did start off with a monthly subscription. I think that just the challenge with that I think it doesn’t foster a true sense of commitment or investment. I think that everyone has, from music streaming services to all kinds of different subscription boxes, things like that, there’s this monthly cadence that we’ve all become accustomed to, but I don’t think it breeds loyalty. I think as well when we looked at reducing churn rate, sometimes people’s credit cards declined or what have you, or they forgot that they had the charge.

It was easier to ask upfront, like, “Hey, rock with us for three months, or rock with us for a year and really get invested.” I think that again, continuing to put a value and a premium on the work that we’re doing is continuing this brand promise of we’re going to deeply cover what’s happening in Black innovation and we want you along for the ride. Make that commitment annually or quarterly. Quarterly is a great way to really test out all the features. It gives you an opportunity to have at least three solid months of great discussions and conversations and as we move forward, will build more opportunity for community building. Overall, the experience, you can’t really get a solid experience in just one month.

Jacob: Can you expand a bit on what’s included in the data library because at least in the B2B space, it’s common for data subscriptions to cost in the four figures per year but you’re including that in the pro membership. Have you thought about creating a more robust and premium price data business?

Sherrell: Absolutely. We’re going to be rolling out some new software and insights tools at the top of Q1 to really capture that part of our audience. The data libraries for us are very standard. They’re really part of what our reporting process has been for specific stories, things like directories. We created the first database of Black owned co-working spaces, measuring this rise of independent work and buildings dedicated specifically to innovation. Being able to provide that as a resource for our audience and for our readers was super paramount.

Then we have databases again on things like who are the top Black researchers in artificial intelligence? Again, converting some of the background work that was traditionally reserved for our stories and making that available to our members. We think we just offered something very unique there. There are several different sectors that we’ve looked at. Even just a rundown of Black CIOs, to Black women whose tech companies have been acquired or they’ve had some liquidity event. Mapping those things that have powered our reporting and our data visualization sharing across social media.

Again, it was going from a test and a resource that we already had on the backend and deciding to make it available as part of that premium tier. We wanted to make it attractive and see how will this stuff be used? How will our folks feel that it’s valued? Then how do we again, upsell them as we move towards a more enterprise level resource? It’s definitely on the horizon. We’ve provided some significant resources. Now as we move forward we will have more of a premium premium tier to our current offering.

Jacob: You also have an events business with the major product being The Plug Live Summit. Can you talk about the structure of that event and the business model vis-à-vis ticket sales and sponsorship? Then how have you had to evolve this event with us living in a COVID world?

Sherrell: The events business is definitely a very precarious one. I think that for every media operator and just event planner overall, this pandemic definitely forced us to pivot very significantly. We hosted our first live summit back in February and that was right before everything got shut down. We were very fortuitous in terms of being able to host that one in person in New York City.

Just about a week or so after is when the world got set on fire. As you can imagine, it was part of our 2020 strategy to start bringing in event revenue and have these intimate coast to coast sit downs with researchers, with entrepreneurs, with investors. To talk about and start to project into the future what the needs and the business climate was going to look like for Black and Brown founders.

As we approached our Q4 summit from a virtual context, we knew that we just had to offer something different and much more robust. It also allowed us to reach a larger audience as well for folks who would not necessarily fly out to New York or to San Francisco to be part of the conversation. From a ticket sales and a sponsorship standpoint, the model still stayed the same. It was probably a bit more work to cut through the noise of all the events that were taking place around the same time.

Just generally, I think that virtual events are just a challenge as people become more burnt out by always being online. As I look ahead and envision what events look like for us in the future, I’ll be very frank. I’m not exactly sure how we make this feel as intimate as we initially designed for in-person. I think the pivoting has been well, I think that being able to bring a protection team on and for all the platform evolution that’s happened around video conferencing has greatly and drastically improved, but we’re still not able to sit in the same room together.

Again, looking ahead into 2021, it’s what can we offer or provide that provides a great experience, dogged information and also builds community, but again doesn’t compromise on safety or quality? Still figuring that part out and hyper-focusing more so on how do we continue to ramp up and build high quality work in general? Then maybe if we’re not able to meet from an events perspective, how do we still foster a deep community that can connect and learn from each other?

Jacob: You recently ran a four-episode podcast called The Clark Street Project. Can you talk about the strategy behind creating this series? Specifically what I mean is, was it to drive additional memberships or did you slash? Do you view this as something that can become a more robust multimedia project, ideally perhaps with a Netflix or a partner like that?

Sherrell: Those are great questions. I think that with everything that we’ve done at The Plug and even in the way in which I started The Plug, it was really about experimentation. We got a tremendous grant opportunity from the News Integrity Initiative that allowed us to have a sense of experimentation. Part of my ethos again is really documenting the contributions of Black entrepreneurship within this country.

THE CLARK STREET PROJECT deeply explores how Black and Brown journalists have made major contributions in terms of helping to document early stage Black entrepreneurs, specifically during times where mainstream newsrooms weren’t covering them at all. From Afro Link in the 1990s who had been funded by AOL, up until current time where we’re looking at platforms like Black Tech Twitter and the connectivity of Black techies connecting online.

In terms of the overall strategy, there was an education component to also test out the ways in which we could further partnerships and develop additional media assets for sponsors that were much more multimedia breadth. Not just the newsletter and not just the website or an online event, but exploring another avenue to provide visibility to partners. As I look forward at embarking on a season two, there’s definitely some of the larger name platforms that we want to have connection with as this content continues to develop.

Quite honestly, it’s all been a learning experience because building the podcast was initially supposed to be set physically in New York city. We had to quickly pivot and I had to order a microphone and I had to soundproof my space and conduct interviews virtually versus in-person. Things got thwarted on that end, but I think overall the experiment did let us know that folks were interested in what we were creating and that this could be a potential brand extension of our overall content.

Jacob: You mentioned sponsorship. On the advertising side, can you talk through the various opportunities you provide partners, because there are many listed on the website from sponsored research, newsletter sponsorships, member calls, and then how do you price those?

Sherrell: That’s such a great question. There are different kinds of opportunities even down to content sponsorships. Particularly with foundations that are invested in journalism and news coverage that is very much geared towards communities of color. We’ve been able to build out those relationships and really focus on a series of topics, be it future of work or ecosystem development or what have you.

In terms of how we price those things, I know traditionally, there’s been that CPM model. Because we’re niche and because we are looking less for volume and much more for our people that are really looking for this content, we knew that it would be a losing game for us to solely focus on CPM. We will provide essentially package deals based on value and general visibility and also really establishing metrics around conversion.

We’ve traditionally partnered with companies that were looking to recruit people into maybe their accelerator programs or to apply for certain funding opportunities. Much more action-driven calls to action that were less about just click to my site and view my product, and more so of you are the product as an audience member and we want you to come into the fold of the programs that we’ve established or that we’re pulling together.

The use case is vastly different there. We try to price on the value that we deliver as well as knowing our audience and segmenting who subscribes to know exactly what it is that they’re looking for when they subscribe and they read The Plug and they read about our partners.

Jacob: What is the technology stack that powers The Plug, from CMS to Membership Software to ESP and anything else that I might be missing?

Sherrell: I used to have a running list of all of the tools that we used because there’s so much that also can be integrated and simplified a bit more. There are a couple of tools that you use for various reasons. I think just from the side that powers The Plug, from WordPress to MailChimp to Memberful, those are top-tier things. Then on the back office side of things, we’re using Asana for project management, of course, things like Dropbox, as well as Wave and Salesforce for analytics and just general reporting and creating systems as our sponsors reach out for inquiries and things like that.

I want to say I always try to keep it as simple as possible, but the more that we do, the more complexities we have to add. We do use a host of software as a service platforms to build our work. Then I think just from a general journalistic standpoint, what’s been great has been social media and just the ability to find stories and scoops, especially since we’re not able to be face-to-face from a tech conference standpoint.

Even being able to use things like Typeform to solicit new startups who are growing, who can share with us their just, here’s what we’re doing, here’s where we’re coming from. Being able to filter that into our Startups to Watch series and our weekly briefing that we send out via MailChimp. I think it’s really makes things seamless for the most part.

Jacob: You mentioned social media. When you were thinking about audience development at The Plug, what tactics and strategies are you focused on specifically?

Sherrell: I have a very distinctive personal brand that is highly tied to The Plug. I think that can sometimes either hinder or help a brand, but for the most part, I think that I respect being a journalist first. When I’m working on stories or a team is working on stories, being able to leverage social media to connect with people quickly, but then also just to be able to discover maybe things that may have initially been outside of my scope or visibility is super important.

Take for instance again, the database we built following all the text statements following the protest over the summer. I asked a question on Twitter and I put out our initial data set and I said, “Hey, here’s who we’ve found in terms of brands that are making public statements. Can you tag additional ones?” Just inbox DMs flooded folks of saying, “Hey, my company just made a statement,” or “Here’s a screenshot of an internal letter.” It helps us to truly do our reporting and I think also to help people feel seen and feel connected to the work that we’re doing.

Quite frankly, I see folks like ProPublica do this quite a bit in terms of, “Hey, we’re working on this kind of story. If this is your experience please hit us up.” I think that having some of that aggregated audience input helps people feel connected in knowing that they get to play a role in helping to give you information and access to information. That I really value social media for. I also like to use it to address issues within the startup ecosystem as a whole. The way that I think Black and Brown entrepreneurs are constantly placed at a disadvantage based on very arbitrary barriers that at this point just seem very unnecessary.

I like to have those kinds of conversations, like, “Why are we still having these conversations? It’s making us inefficient and unproductive.” I also like to share on our reporting and why we’ve done stories the way that we’ve done across that be Twitter, Instagram or even LinkedIn. Just really help to expose people that normally wouldn’t necessarily be checking for The Plug or even checking for me a way to engage and to learn. I try to teach and educate around topics specifically related to race and communities that are typically not seen as spaces for innovation, but very much are.

I try to bring that to the forefront because, as I mentioned earlier in the conversation, the idea that the kind of coverage that Black and Brown and female startups have received in the past has been this like, hey, this is such an anomaly and this is so great and pat on the back, versus, “I’m around smart, dogged, very well educated, very well trained experts all the time that just happened to come from various degrees of backgrounds. Because we’re not as visible in the media as having normal regular lives, we have to be overly emotive and overly represent ourselves, our families, our communities online to remind people that we’re not stupid and we also have opinions about these spaces.

Oh, and by the way, we did a survey of Black-owned tech companies and the kinds of software products that they use. As I mentioned, I’m using products like WordPress, I’m using products like Asana, I’m using Wave for sending invoices, and what have you. The reality is when we think about the number of dollars that are contributed to these big tech companies, there really is an economy out of the Black tech startup ecosystem that cannot be ignored. Particularly when it comes to workforce representation, because if I’m pumping my money into Google and G-Suite, I want to know that Google has a commitment to hiring and treating well folks of color.

I want to know that they’re making commitments to ensuring that college students from all kinds of backgrounds have access to get jobs there. Because if I’m giving them $200 a month in order to manage my email and some of my domains, surely I want to know that this is a company that I’m making an investment in that’s making an investment in the values that I care about.

Jacob: Digging into a little bit more on the audience development tactics, The Plug doesn’t put all of its content behind the paid membership, so it’s not a true hard paywall. How do you find a balance between giving your paid members enough exclusive value while also having enough content that can go wide and act as a top-of-the-funnel for you?

Sherrell: We try to base that on the kinds of content partnerships we develop. For instance, we have a really great partnership with the Kauffman Foundation, which invests in entrepreneurship education and ecosystems. The work that we do in partnership with them, or even an organization like Venture Philanthropy Firm New Profit, which we did a feature of work series with them, those things are generally open to the public.

Essentially, they’ve been paid for in advance and they have a general public interest. Versus we try to differentiate the content that we’re delivering specifically to our members, which is much more of a depth of examination of a particular company or a particular idea surrounding a particular industry and some advances within maybe a Black tech startup or a firm or what have you. Sometimes there are things that are just generally within the public interest that really makes sense to unlock for readers to be able to view and have access to. We do try to ensure that some of the deeper dives and more long form are reserved for our paid members.

Jacob: Thinking about The Plug over the next few years, do you believe that it will look materially different than it is today? Are there new product ideas that you’re thinking about launching or new streams of revenue that you’d like to tap into? Ultimately, where do you go from here?

Sherrell: I think that’s a great question. I would consider us to be almost a new business every six months. I definitely believe that as we learn and grow, get access to more capital, our revenue increases. I’m able to make some deep investments in people as well as systems and operations that allow us to become much more efficient. From a general growth and vision perspective, right now we are exclusively reporting in the US.

I see us having more of an international platform, being able to work with researchers as well as journalists in up-and-coming Black tech hubs all over the world, from Brazil to Nigeria to the Caribbean in these spaces that have pretty tremendous activity and have seen much more investment from large firms in terms of growing those ecosystems. I think from a journalistic and editorial perspective, definitely growth across the verticals that we’ll be covering.

Then we are in the process of launching some software and some insights tools that will specifically be geared towards enterprise clients. Definitely from a product standpoint, there will definitely be extension there, an opportunity for us to really provide deeply, deeply developed research reports that will be productized themselves. That will be outside of pro membership to be a next tier above for industry to really take advantage of.

Beyond that, I would love to again have events, but I think structuring them beyond a conference is where I want to get creative and become much more thoughtful in terms of application. My goal is not to just provide the sense of resource and information for information sake, but to provide the utility for the clients and customers that are going to be making pretty deep decisions, specifically related to how inclusivity really drives their business moving forward.

I think we have a loose roadmap, but if I’ve learned anything this year in a pandemic, it is to be flexible, and be nimble, and being able to be adaptive because we don’t know what’s going to happen in the world. We definitely have some strategic frameworks around really expanding research content and monetizing our insights and our reports.

Jacob: Before we move to the last part of the show, I want to reference something that 2PM’s Webb Smith wrote about you. “Though every technology firm now wants to hire her away from her idea turned creation, I should suspect she will have more impact independently.” Because you are a big part of The Plug‘s brand, how do you think about that balance between everyone wanting your time, including me, and building a media company that takes so much of your focus?

Sherrell: I definitely try to work to be judicious with our time, anything that allows us to talk about what we’re building and how it’s beneficial to people discovering us, as well as learning more about us. When it comes to some of the offers that I’ve received, I think that sometimes I have the conversation because I think number one, it’s flattering and number two, because I know that I always know someone else that would be a really strong fit and I like the ability to provide another resource for someone else.

I’ve had to be very intentional about the way that I spend my time now, especially as we continue to grow, and do some fundraising, and really think about where we’re heading and how we need to get there. I think there’s this case by case basis to create that sense of filtering of what’s going to push the brand forward versus what is just nice to do. As you can imagine, over the summer there was always a request for can you speak to us about this? Can we talk about this?

There’s this propensity for people to reach out to want to talk about diversity and that’s the only thing that people tap you for when you’re a person of color. When you’re a woman, it’s always like, “Can you speak on our panel about being a woman in tech or being a woman in journalism?” I don’t think there’s necessarily a harmful intention around that, but I do think that we have to evolve the conversation.

When I can talk about the business that I’m building or I can talk about what I’m learning in the process, I try to jump at those opportunities, especially when I think that it’s going to provide and do justice to what we’re building and why this is significant as we move into the future. I’ve even just cut down my meeting days to just twice a week so that I can focus on the other days of the week, specifically on growing the business.

Jacob: I want to end with the same two questions I ask everyone on the show. Looking at your media career, what is a mistake that you made and what did you learn from it that made you better professionally?

Sherrell: Gosh, I feel like building anything from the ground up, there’s so many mistakes. I think there’s mistakes around just bringing on talent, even be at freelance, because you only have so many resources. You can only bring on the best that you can afford and even if it’s not the best fit. I think as a leader in general, having to be much more polished even in the way that I present even on social media.

I’ve definitely had those moments where I’ve had Twitter rants and realizing that sometimes you can alienate people by not being very careful on how you’re delivering information. If the goal is to bring new ideas forward and to build community and to build a reservoir of talented people within your corner in which to siphon information about who’s doing what, I can’t be the angry Black woman on Twitter.

Sometimes I can be angry when things just deserve that vitriol, especially when we’re talking about the murder of folks. Then you go into like, “Hey, police did murder another Black man.” Yet I have to interview this person, or I have to hop on this conference call and still work while still being deeply emotionally disturbed.

I think just in terms of having very early convictions about what venture capital is and isn’t, for me, I was very anti raising money, because I didn’t want to dilute the experience of what journalism should be. I didn’t want to dilute the experience of building slow and intentionally and wanting to really test out what we were building first. I think that some of those early convictions stunted my ability to really see how money is used as a tool and how building the right relationships within VC can actually be used to progress what the mission is and what the what the what the overall goal is.

Quite honestly, I plan to continue to make more mistakes. I think that it has made me a better leader, I think that out of the frustration of not getting it right on the first time has also helped me to be much more humble in terms of building a strong network of experts and people who have run this road before, that I’m able to consult with and reach out to and learn from, even if it is just from afar. I’m grateful for those particular mistakes but I think overall, they’re making me a stronger leader and helping me to build a stronger company.

Jacob: If you could offer current or prospective media operators some advice to succeed in media, what would it be?

Sherrell: I think that staying resistant and resilient is super important, visibly talking about your work and why it matters. It takes some time to really convince people that this is important. I look at some folks that I follow and subscribe to who are specifically talking about climate change and I know how challenging reporting in that space is. I think staying consistent and staying on message and dogged about what you’re building is important.

Quickly try to find a path towards sustainability. Not all of us. I didn’t necessarily intend to turn The Plug into this company that it is today. I just started with experimenting and a labor of love and then looking at, “Okay, what’s my quickest path to work to revenue?” Then how do I build that up enough and how do I drop in subscriptions and how to experiment with this and how do I go after grants in order to make this a viable business for myself and for others? I think if you can figure that out quickly and experiment quickly and know what works and what doesn’t and stay resilient in that process, I think you’ll do very well.