James Chapman, Plain Sight

What’s the inspiration behind Plain Sight?

I’ve always had a passion for entrepreneurial and creative development endeavors. Around 2016, I started a co-working space for side-hustlers open between the hours of 6pm and midnight. The people coming to the space would always ask me who was working there, and they were eager to make connections based on their specific needs. That’s where the idea came from: I wanted to create a way for people to make new, hyper-local connections with others who have complementary interests.

James designed Plain Sight to remove unconscious biases in tech

This is not your first time founding a company—what do you think is the most important skill founders need to succeed?

Patience. Building a company that lasts takes time. You can’t skip to the end or rush the process. There are beautiful lessons to be learned from the journey of building a business. If you try to rush it, you might miss something that will actually make your product or service defensible and more sought after.

James at work in his co-working space for side-hustlers

You previously started Detroit Demo Day, which provided over $4M in funding to small businesses. How did this experience your plans for Plain Sight?

Detroit Demo Day is my love. Being able to provide access to financial capital for entrepreneurs who need it most gives me great fulfillment. With Plain Sight, we are creating access to human capital. What that does is get to the root of the need. I believe that once you can access the right human capital and grow your network, the money will be more readily available to you.

James, Entrepreneur in Residence, at Detroit Demo Day 2019

What does “hustle” mean to you?

The hustle is the great equalizer. You may not be able to control the cards you're dealt, but you can control the effort you put forward. The hustle is the pursuit of your goals. It looks different for everyone, which makes it so special. It’s the secret sauce to achieving success—whatever that looks like for you.

The hustle is the pursuit of your goals. It looks different for everyone, which makes it so special.

How do you handle risk and competition?

I don’t. I stay in my own lane with my unique offering and my vision. I spend more time with our users than I do studying competition. There’s enough out here for everyone to win, so I’d rather stay focused on the main thing: providing value and solving problems with our unique offering. After that, I let the chips fall how they may.

Plain Sight as exhibitor at the Forbes 30 Under 30 Summit

What’s been the #1 (or two) top challenge(s) you’ve faced while launching your company?

The pandemic, without question. We had a plan and a path forward that was beginning to bear fruit. Then, out of nowhere, it was all snatched away. Like others, we couldn’t plan for it, we only had to react to it (and in many ways are still reacting to it). Usually that type of shift takes years and it happened to us within a matter of days, and it's now something all entrepreneurs need to navigate.

A day in the office at Plain Sight pre-COVIDHave you learned anything new or surprising about yourself through this process?

Just how resilient I am. I was brought up to be tough, but honestly, I’ve just taken the stance of not giving up. If we lose, I know my team and I did everything we possibly could do to be successful. 

James having a candid conversation at Michigan House for SXSWIt’s been harder than ever to curate meaningful connections during the pandemic. What are some surprising ways you’ve built relationships over the last year? 

One thing that sticks out to me is that I have become a part of this small group of six other entrepreneurs who meet every other week via Zoom. It’s a guided format, and we discuss both business and personal topics. This has been a great experience not just for my personal and professional growth, but I now have a new group of friends that I can call on at any time. 

What’s your team culture like? 

Authentic. I try to empower my team to come to the table as they are. We are all very different and that’s what makes us special and powerful. I don't want anyone to feel afraid to bring their thoughts to the table. We have tough and open conversations, we respect one another, and we work very hard.

An illustration of the team at Plain Sight

What is your superpower?

I’m approachable. Which certainly helps when you’re building community.

What’s your kryptonite?

Game of Thrones. I can’t stop watching it, haha, even when I sometimes need to be working. 

What’s the best piece of advice you’ve received?

What you do to get there will have to be different than what you do to stay there, and go higher still.

James onstage at the Forbes 30 Under 30 Summit