Networking to achieve your dreams, with Plain Sight founder James Chapman

Donald Thompson says that being a former athlete can make you a better entrepreneur, and James Chapman is no exception. Having played basketball throughout his entire childhood, the founder and CEO of Plain Sight, a mobile app for networking with like-minded people in virtual and physical spaces, is a serial entrepreneur with a passion for helping others achieve their goals, too. In this episode, Donald and James discuss what it takes to turn your ideas into a full time job.


Donald Thompson: Welcome to the Donald Thompson Podcast. I’m here with my good friend, James Chapman, and James is the founder and CEO of Plain Sight. James, welcome aboard.

James Chapman: Man, thanks for having me. It’s good to be here. How are you today?

Donald Thompson: I’m doing really well, I’m doing really well. A little bit, like most people, a little tired of being inside all the time. But I’m happy, I’m healthy, and doing well. Thanks for asking.

James Chapman: That’s right. Yep. That’s that’s most important, man. I’m glad to hear that.

Donald Thompson: James, one of the things that I enjoy doing  with our guests on the podcast is I want to give you some space to talk about you as an individual. Where are you from? Married? Single? You have kids? Where are you educated? Take a moment and just give us a little bit about James Chapman, the individual.

James Chapman: Yeah. So, I’m from Chattanooga, Tennessee, so I’ll start there. I’ve been living in Detroit, , for about four and a half years. Now it’ll be five years in May. And you know, I never thought that I would be living  in Detroit.

I always thought that I would probably just be living, you know, in Chattanooga or somewhere close to it because all of my family, you know, is also born and raised in the city.  Not married, no kids, girlfriend/dating.  Grew up playing basketball,  been playing basketball ever since I was three years old.

You know, I think that if you would’ve asked me when I was 17, 18 years old, what I was going to do with my life, I would have probably told you, you know, go into the NBA, but you know, who dreams the flake, you know, at some point and, you know, had to find a new path.  I’ve always been kind of curious about problem solving and always been hustling and entrepreneurship has been something that’s always fascinated me.

So I think that that’s what’s been sticky for me. I think that I always took pride to the day that I leave, leave this world, be an entrepreneur that helps other entrepreneurs because you know, that’s something that I’m passionate about. So, yeah, that’s a little bit about me.

Donald Thompson: No, I appreciate it, man. And it’s good to hear, because a lot of times former athletes, one of the things, and I take this, mine was on the football field, there’s a lot of lessons that you can learn for business from being a competitive athlete. The teamwork, the toughness, the follow-through in terms of…

James Chapman: The competitiveness, right. The competing.

Donald Thompson: That’s exactly right. And so that’s a great segue into my next question. As we move into the creation and the foundation of Plain Sight. But before that, I want to give you some space to talk about why and how you fell into, or became an entrepreneur. What was the points that drove you into that as a career and as a colleague?

James Chapman: Yeah, so man, like I remember as a kid, I used to take my toys to school when I was done playing with them and sell them. You know what I mean?, I’m like just doing little stuff like that. And my mom got pissed about that but, you know, I didn’t even know that that was a form of entrepreneurship. at at that time, but you know, it was. And I remember in college, I started toying around with selling shoes.

You know, this is before some of the big companies like StockX and GOAT and all this other stuff did the flipping of  the shoes. It was just like, kind of like a little side hustle for me, so I can have some money to take girls to the movies and, you know, stuff like that. So, you know, I think I’d always been curious and dibbling and dabbling with entrepreneurship as a youth.

But then I think the point where I decided to really take entrepreneurship seriously is when I felt like I had reached a ceiling in a job that I was working, right. So, actually i’ll back up a little bit more even before that, played college basketball. Went on to play down in Mexico for a season. Tried my hand at the NBA development league, got cut after training camp.

And I think that that’s  when I stopped with ball and moved back home to Chattanooga, and I started working in workforce development. And you know, while working in workforce,  it taught me a lot, actually. I think that that’s where I became an actual professional,  and started learning about how to conduct myself in business and things of that nature.

I started being really passionate about seeing people’s growth within their own careers, you know, from working in workforce development. And so I ended up, after probably working, , working within that organization for about four years or so, decided that  there’s not more that I could do here within this place.

You know, I was like, I can’t move. There’s not many more moves up, so at some point I got to move out, and just decided to try my hand at business. And so I think that, you know, that’s kind of been the evolution for me from going from, you know, just a snotty nose kid, you know, growing up in Chattanooga, Tennessee with hoop dreams into, you know, working in workforce, to then becoming a full-time entrepreneur.

Donald Thompson: Oh, that’s phenomenal. I think we got the title of the podcast though – From Hoop Dreams to Entrepreneurial Success. That’s good, that’s good stuff. Now transition us to more specifically now your firm Plain Sight. A lot of entrepreneurs are people that are thinking about starting their company, have ideas.

But one of the things we like to share with people is how do you take that concept and then move it to that process of commercializing it into a real company. I’d love to hear your thoughts on that from your perspective of Plain Sight.

James Chapman: Right, I’ve done some entrepreneurship training and things of that nature within my tenure and my career.

And, you know, watching people go from idea to action is very interesting. You know, a lot of people have ideas, a lot of people have things that they’re passionate about that they want to make their full time gig, right. But it’s, it’s all of the little details and in the middle that matter most.

And you know, some of the things that I realized from just being an entrepreneur and being somebody who studies entrepreneurship and being passionate about that growth process. You know, I’ve realized that once it’s time to take that idea into action and start thinking about how you’re going to make money. thinking about who your true competitors are, right. And then also thinking about are you the right person to run this business. That’s when it starts to like drift off a little bit, you know what I’m saying?

So like, you know, the first business that I started after workforce was actually an oil change business. It was an oil change delivery business, and it started to have some success, but it didn’t speak to my passions, right. And so I couldn’t see myself doing it long term. I stopped getting excited, you know, waking up, doing it and things of that nature. And so it’ll become short lived if that’s the case.

So, you know, if anybody who’s watching and listening that’s, you know, trying their hand at entrepreneurship, I would say one, make sure that it’s something that you care about, something that you’re passionate about. Something that you can wake up every day excited about, you know, solving that problem.

And then two, really try to understand how you’re going to be paid for solving that problem, right. Because at the end of the day, If you don’t end up turning that thing into a business or trying to find some way to monetize it, it’ll just be a hobby and that’s fine. You know, passion projects or hobbies,  there’s nothing wrong with that whatsoever, right.

We all need those things, but there’s a big difference between doing that and turning it into a business. And so I’ll segue a little bit now into Plain Sight. I ended up, what gave me the idea for Plain Sight actually is because I started this coworking space for side hustlers. This place was open between the hours of 6:00 PM and midnight.

And so, I was always working on my stuff and people were coming to me saying like, y’all, how did you get your business funded? You know, how do you put a business plan together? Things of that nature off of the oil change business, I started falling in love with their process and just realizing that people need human capital. Right? That’s one of the biggest things that folks don’t talk about that that will make or break your success in your career, whether it’s business or anything else is how can you get connected to the right human capital that’s going to allow you to have open doors so that you can be successful, so that you can learn, so that you can turn that idea into something sustainable.

And so, you know, the number one question that people would ask me when they were come  to the nighttime space, the space was dope, but they would say like, yo, who’s in the space right now, or who’s going to be in the space tonight, or can you help you get connected to, somebody that does this or that.

And that’s when I really started to realize the power of human capital and then started becoming obsessed with how technology could better help leverage  bridging the gap between people who have connections and people who don’t.

Donald Thompson: Oh, that’s powerful. And I want to just restate the ending, right. People who have connections and people who don’t, because a friend of mine taught me early on in my career that your net worth, right, is in your network. Right, so that you can, you can attach yourself to the people you need at the moment that can help you over that hurdle or question or door that you need open. And so, that’s powerful in terms of that human capital.

Now tell us a little bit about Plain Sight, the vision of that company, what it is, what it does, and why it matters to the world.

James Chapman: Yeah. Plain Sight is a social platform for like-minded professionals and business people to get connected with one another in virtual and physical spaces.

So I go back to the reason why I started it, what gave me the idea was when I was running that nighttime workspace. And so like, if you think about the places that you go that says something about you. The people who are going to that nighttime workspace, they were side hustlers. They were working on their thing.

And so they wanted to build community within each other, right. People want to do business with people that they relate to, that they can understand, that they feel comfortable with, things of that nature. So that’s what we’re doing with Plain Sight is we’re creating these spaces, whether they’re virtual or physical, for people be able to tap into, find people who are like-minded, and be able to share resources, news, inspiration, whatever it is, so that you can get better connected to the human capital. That’s going to allow you to leverage that human capital so that you can have overall success with what you’re doing.

Donald Thompson:  Now, is this a bootstrapped business? Do you have investors? Tell us a little bit about that journey to actually start scaling this opportunity.

James Chapman: It started off with just me putting up my own money for a web app, getting it built with the company out in LA. From there, I started going around to different coworking spaces and telling the coworking space managers that I would pay for lunch for their members if they’d be willing to test out the application. So we got a bunch of feedback from that, you know, just like buying tacos and pizza for people,  you use that information, put it into a pitch deck and then started to shop it around with investors so that we could get a mobile app built.

I’m a non-technical founder. I’ve never written a line of code in my life. So we had to find somebody to build that thing up from the ground up, we took on some investors to be able to do that. And today, Plain Sight has raised a million dollars total for the venture.

Donald Thompson: Oh my gosh.  A lot of good stuff there, I want to lean into the raise of a million dollars. There’s a small percentage of African-American led firms that reached that milestone in terms of investment capital.  Why did you make it when others don’t?

James Chapman: If I’m honest, is because of the ability that I’ve had to leverage my own human capital, right. I tap into my contacts from my professional career, whether it be the work that I’ve been doing at Detroit, with building Detroit Demo Day, or the workspace. The people who I’ve met along the way who have bought into me that said like, okay, this is somebody that I believe in because, Oh, pause for a second.

Whenever you’re raising your initial, like funding they’re betting on the jockey, not the horse, right. It doesn’t have a whole lot to do with what you’re building, because you’re just getting started. So you haven’t proven anything really yet, right? Like,  so people are betting on you more than they’re betting on the business.

And again, that’s why making meaningful connections with people and having a deep Rolodex and contacts is so important because if people can see that I built business, and doing it a number of different ways, and I’ve proven myself as an operator. Now I’m not going to them saying, Hey, I’ve got this business that I want to run. There’s a market for it. There’s a need for it, and I feel like I’m the best person to run that. Then people are going to be more inclined to say, all right, James, you know what, I’m willing to bet on you. So I honestly believe that I was able to raise that money from leveraging my contacts that I built over a number of years, you know, I used to work for Rock Ventures, right.

And so like learning the game, like it took me a while to just like learn venture, and learn what it means to even be able to raise money because I’ve never done this before. You don’t know what you don’t know. It’s a long story, less long to answer your question more directly now, I’ve just made a number of different contacts, man.

And I’ve never been shy about trying to meet somebody and deal with them, and build in a very authentic way.  Like if it was so transactional, if all of your relationships are just transactional relationships, that’s not going to get it. You know what I’m saying? Like I’m willing to give to other people.

And then at some point, my time is going to come around where I’m wanting to do something that people are willing to pour into me. So, that’s the stuff that doesn’t show up on paper Donald, you know what I mean? But, but that’s how I’ve been able to do it.

Donald Thompson: You know, one of the things when people talk about, and we’ll come back to Plain Sight a little bit more detail, but I want to hit a point you made about your networking and being willing to give and activate your network. Most people think about networking as a one-way street. What can I get? And even in our first meetings, we both shared with each other things we could do to support we did the two way street , and that is what I think some people miss on their journey to network is is that they’re easy and good at asking for.

But what are they doing to deliver and to be a benefit or a resource to someone else. And then you have that network power, right, when you become that  conduit. And so I wanted to share that because even in our experience together, we both had a 30 minute call. We talked about business, but we looked at ways that we could be a blessing to each other.

James Chapman: That’s right. And it came natural, like it wasn’t forced,  you know what I’m saying? Like, I told you what I was into, you told me what you were into. And I was like, you know what? Oh, I think I can tie a few threads for you man, to help you out in what you’re doing, and expecting nothing in return, you know? And you didn’t expect anything from me, but to try to get an understanding of what I was doing, right.

And who knows? Like two years from now because we know that we’re solid people willing to build and help each other. You may throw me an opportunity, or I may throw you one, just because I know. And so it’s like, again, you can’t duplicate an authentic organic relationship.

Donald Thompson: Now take me into a little more detail on Plain Sight. You’re launching into the Raleigh, North Carolina area where I’m based in, and I’m happy to help push the message and share the narrative. But in your words, tell me why Plain Sight is valuable to business people, entrepreneurs, and why we should use your platform?

James Chapman: Yeah, I mean, now more than ever building community is critical.  The coronavirus is a very serious thing and it should be taken seriously and we need to do everything that we can do to keep everybody safe. Well, we still have to be a business and we still have to be able to engage and we still have to be able to grow.

And so if you, as a business professional, if you’re looking to grow and to connect and to meet new people so that you can expand your network, so that you can grow within your business, that’s why Plain Sight is going to be important.  And there’s other tools that are out there. LinkedIn is very great for like connecting with people who you’ve heard of, or that you’ve come across, and that you know already. So you add them to your network, et cetera, et cetera. And they’ve got a number of other different features.

What we try to do is say, these are the things that you’re interested in. There’s other people out there that are interested in these same things, and you need to find these communities and you need to build with them regardless of it’s virtual or in person. And we still have some physical spaces that are listed on the platform, but we show you the cleaning and safety precautious of those spaces. So that prior to arrival, we know what you’re getting yourself into. And then once you check in you can be social from a social distance.

So we didn’t create this platform for this pandemic that we’re in, but in my honest opinion, and I know I’m the CEO, so, you know, I’ve got a ton of sound bites in my back pocket that I can always use.  But at the end of the day, like I honestly believe that we’re probably more valuable now, during this time where this whole virtual in-person stuff is a little bit in flux, than when we were when we first started with trying to get people connected and fast paced, high density environments, like the networking events, like  some of those in person spaces. So that’s why I think we’re going to be able to help a lot of people right now.

Donald Thompson: Let me see if I make sure I understand. And you correct me if I’m a little off key when comparing the LinkedIn as a networking site, you’re actually trying to physically and/or virtually bring people together. So that, that last mile of the relationship not knowing who’s available and what they do, but actually creating that active connectivity.

James Chapman: You got it, you got it. We don’t even show you names or profile pictures. We want you connecting based off of skills, interests, things that you’re looking for, things that you want to do with people. So we ask you questions, like, are you looking to hire? Are you looking to fundraise? You know, are, are you looking to work remote? Like, what is it that you’re looking to do? What type of people are you looking for? Are you looking for graphic designers? Are you looking for freelance writers? Like who are the types of people, skills and interests that you’re looking for?

And then we try to curate your experiences in the platform and get you connected with those types of people. So like, these are all strangers, but you have things in common with these people, at least the people that you want to get to know and grow your network with, right? It’s just like walking into a networking event and not knowing anybody that’s in the room, but knowing that there’s likely somebody in this room who can help you with your journey, that’s Plain Sight. It’s just with the internet.

Donald Thompson: That is awesome. When you think about your entrepreneurial journey, what are some of the lessons learned, that you would share with an emerging entrepreneur?

James Chapman: I mean, where do I start, man? Like, I feel like if there was something that could, that I could have done wrong and broken and messed up, then I probably did it. You know what I’m saying?  I’ve been a person, honestly, Donald like through my career that I haven’t been afraid to just like try something if it doesn’t work and whatever, and I learned from it and I’ll go and try something else, right. And I’ll try to keep iterating until I get it right. And so, you know, that trial and error approach, you know, can hurt a lot of times and sometimes can be costly, but, you know, I’ve learned some valuable things that’s going to help me with future endeavors and hopefully be able to help other people.

So one of those things I would say is whenever you’re planning out your financials and you’re doing your projections, and you’re trying to figure out how much money do I actually need to start running this business. . Whatever research you find, or whatever analytics and data that you pull about those fundraisers and their projections. Go ahead and double that because there’s things that you didn’t think about there’s things that you left out. And what you do not want to do is put yourself in a bad position where you’re under-capitalized and now you don’t have a way of getting to where you’re trying to go, you know, not to no fault of your own, but outside of just not having the resources necessary to do that, you know what I’m saying?

I got in a pretty bad situation with being under-capitalized early in my career with another venture. You know, I just didn’t know how much money that I needed to make this thing go. I didn’t take into consideration paying myself, you know, like all sorts of things. I would say, you know, that’s, that’s probably the biggest one. Like it takes money to make money and you need to make sure that your I’s are dotted and T’s are crossed, and then also give yourself enough cushion.

And then also I would say  don’t do more than what you need to do. It’s easy to fall in love with the bells and whistles and think that I have to have it all right now. Ask yourself what you really need to serve one customer. What do you need to serve one customer today? And that’s where you start, you know what I mean? Think big, but start small and then get enough resources so that you can start small and then go from there. You know what I’m saying?

Because a lot of people, cash is King and once you’re out of cash you’re dead. So make sure that you, that you provide yourself with enough resources so that you put yourself in a position to even be successful.

Donald Thompson: And listen, that is wisdom and that’s brilliance in a bottle. That’s what that is, right? Because the thing about it is we can allow ourselves to have this view of entrepreneurship and the cocktail party coolness of it, right. But the missing  ingredient is the commitment part,  and the number of nos before you get a yes from an investor standpoint.

A lot of times people talk about their business, their idea, their experience. But what I found in successful entrepreneurs is their temperament, right? Through what lens do you view the failures you need to go through to get to the successes, right. And that  temperament is really, really important. When I’ve gotten that right I’ve invested in firms or done things that have worked out well, where I’ve got that wrong is like burning money in the parking lot.

James Chapman: That’s right. Because stuff’s going to happen. Like nobody planned for this pandemic, man. But I honestly believe that  the people who are going to be really successful and get to the other side of this thing, once the world gets on a better side of COVID, whenever that’s going to be, whatever.

But I think that the people who are going to battle through this, especially the ones that are kind of early stages and that kind of stuff, they’re just resilient. there’s no other way around it. You have to have resilience to be able to get on the other side  of something like this, because it’s hard, anybody that goes out of business because of this don’t feel bad.

You know, it’s not your fault.  This is something that you could not have planned  for.  But I will say you got to take your hat off to the people who are going to power through this who are going to get on the other side, the ones who are going to pivot, the ones who are going to adjust, the ones who are going to adapt. You know, that that’s that true resilience. And those are the types of people that you want to bet on.

Donald Thompson: When I think about Plain Sight, and now I want you to take it even a little more granular. I’m going through the app store, I see you, your article where you were featured in WRAL tech. I heard about it from a friend.

Talk me through when I download the app, what am I doing? Step by step right now, get access to these people in places and ventures.

James Chapman: Yup, I would say the first thing is create a full profile. You know, we can’t connect you to people if we don’t know anything about you. So make sure that you have a full profile. The second thing that I would say is find a space to check into.

We now have virtual spaces that are listed, that anybody can see them no matter where they are, as well as some physical spaces, depending upon what cities taht were in. And you know, the other thing is, we launched this last October and we’ve had to make a lot of pivots and adjustments too. So I would also say understand where we’re going with this and be patient with us.

There’s going to be a lot of value that we’re going to be able to provide with this. And man, we have some pretty amazing opportunities that I would’ve never imagined with it, you know, that we’ve been blessed with and put in our lap that are upcoming.  But the first thing that I would say do. Download the app, create a profile and find a place to get checked into.

Find some type of space that sticks out to you that speaks to you.  Use the search feature, you can search by skills, interests, professions, and then do your part. We’re trying to reach out and find those people and make those meaningful connections. We’re going to try to help as much as we can. We’ll put in that information out there. But at the end of the day, it’s going to be totally up to the user to use that tool as much as they possibly can.

Donald Thompson: And tell me your website, where people can download the app. Like give me some of the details. So as people hear and are interested, they can act.

James Chapman: Absolutely. And thank you for asking, if you search Plain Sight in your app store, we’re going to be the first thing that pops up. P-L-A-I-N S-I-G-H-T. And our website is

Donald Thompson: What are the things when you think about our current economic environment, pandemic racial tension, election that’s finished or almost finished depending on who you kind of know, what advice do you give people to keep focused and motivated through all this external chaos?

James Chapman: I would say, you know, don’t lose sight of who you are and why you started what you started. , and also, you know things are really hard right now, very discouraging. You know,  you’ve got family members getting sick. You’ve got the racial injustices that you mentioned depending upon which side of the fence are on that stuff and politics and all of that.

I realized that I have to take my mental health very serious, and I realized during this pandemic, how strong the mind actually is. Right. And so I would say, don’t forget who you are. Don’t forget why you started what you started. And don’t forget that you can get through anything as long as you put your mind to it.

And that sounds cliche, but it’s so real. The things that you think come into existence, man. And if you believe that you can win through all of these things. And if you believe that you’re resilient, it starts with belief. It starts up here and I know it was very hard, but I would say take care of your mental health.

Try to keep your mind strong, try to surround yourself with positive people who can pour into you because honestly, you know, some of these social platforms have gotten pretty toxic.  And you know, you can open up a social platform and that stuff can get into your psyche and then,  you know, put you in a bad place.

So I would say, just try to stand at this space mentally and try to remember, you know, all the things that you had before this pandemic and the abilities that you have to be able to execute all the things that you can do, and everything will work itself out.

Donald Thompson: James, I appreciate that. That’s a good word of encouragement because we’re all working through these things the best that we can, right. And that statement that you made surrounding yourself with people that will have a positive impact on you, right, is a win, because we all need each other to make sure that we can continue to continue to protect that mental health so that we can win on the other side.

That’s right.

That’s exactly right. James, I enjoyed it. It was great to get to know you a little bit better individually, but more importantly, right, to start to introduce Plain Sight to the folks in the RTP area. Cause I know that’s one of the markets that you all are looking to, to attack. And if I can do anything, to continue to further your growth and success. Please, let me know my friend.

James Chapman: Man., I appreciate this opportunity. Thank you for extending it to me.  I mean that, and also if there’s anything that I could do for you to help out in any way, please let me know. I look forward to expanding out into your area and also, that first beer is on me, man, once we get on the other side of this thing and we can chop it up in person. So I’m looking forward to that day for sure.

Donald Thompson: Sounds good, my friend.

Full Episode Transcript

The Donald Thompson Podcast is hosted by Walk West CEO, The Diversity Movement CEO, mentor, investor, and Diversity and Inclusion Consultant Donald Thompson.

Music for this episode provided by Jensen Reed from his song, “You Can’t Stop Me”.

The Donald Thompson Podcast is edited and produced by Earfluence. For more on how to engage your community or build your personal brand through podcasting, visit

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