If you’ve ever attended a networking event that felt like a waste of time, you’re not alone. Too often, attendees leave without meaningful connections, and sponsors struggle to see ROI. James Chapman saw this problem firsthand—and turned it into a business.
As the founder and CEO of Plain Sight, James built a platform that helps event attendees connect with the right people and makes sponsorships easier for brands. Think of it like a marketplace like Uber that connects drivers and riders… Only Plain Sight is connecting event creators and sponsors.
Plain Sight has been behind countless successful events all over the US. But getting there wasn’t easy. With no product, no funding, and no team, founder James Chapman truly started from scratch.
Today, he’s raised over $1 million and works with major brands like Microsoft and GitHub to improve event experiences.
Here’s how James did it—and what you can learn if you’re trying to launch a business from nothing.
Spotting a Real Problem
James’ entrepreneurial journey started not with a tech company but with community-driven events.
“I was hosting late-night coworking sessions, and people kept asking, ‘Who else is coming? Can you connect me to someone in my industry?’” James recalls. “That’s when I realized networking at events was broken.”
At every event, attendees struggled to meet the right people, and sponsors weren’t getting enough value. This was a gap in the market that nobody was addressing.
The takeaway for James (and founders) is that before building anything, you have to find a real pain point or problem worth soliving. If people keep asking for the same thing, that’s a business opportunity.
Launching Before Everything Is Perfect
James didn’t wait for a perfect product to start testing his idea.
“We started by hosting our own events, curating networking experiences, and bringing in sponsors,” he says. “We saw immediately that when connections were intentional, people stayed longer, engaged more, and sponsors saw better results.”
At first, Plain Sight focused on ticketing, but James quickly realized the real value was in sponsorships—helping brands connect with the right audiences through events.
Testing your idea with real users before building a full product is key. The market will tell you what works.
Raising Money by Selling the Vision
In 2019, James secured $1 million in pre-seed funding, with investments from Dan Gilbert, owner of the Cleveland Cavaliers and a major backer of StockX.
“When you raise pre-seed, investors aren’t betting on the business—they’re betting on you,” he says. “They saw my track record in events and my ability to execute.”
However, looking back, James says he would have raised less money upfront.
“I would’ve started leaner, proved product-market fit faster, and then raised more strategically. The pandemic hit right after we launched, and we had to stretch that funding longer than expected.”
Investors back expertise. Build credibility, show small wins, and don’t raise big money too early.
Pivoting When the Market Changes
Plain Sight launched in October 2019—four months before the pandemic shut down the events industry.
“We had just launched, and suddenly, there were no events,” James says. “Investors were telling me, ‘Maybe it’s time to move on.’”
Instead, James relocated to the southeast, where events were reopening sooner, and shifted Plain Sight’s focus to sponsorships.
“The real pain point wasn’t just event logistics—it was how brands find and manage sponsorships. Companies were drowning in requests but had no structured way to vet them.”
By positioning Plain Sight as a sponsorship management tool, James unlocked a scalable revenue model, and major brands like Microsoft and GitHub started coming back for repeat deals.
If the market changes, founders have to adapt quickly. Listening to customers and being willing to pivot can determine whether a business survives or fails.
Scaling by Focusing on Revenue First
Early on, James invested heavily in product development but quickly realized that sales and marketing should have come first.
“Your first hires should drive revenue,” he says. “We grew by hosting our own events, bringing in sponsors, and then keeping those sponsors engaged for future events.”
Once he proved that companies were willing to pay, growth followed naturally.
Before scaling, make sure people are paying for your solution. Growth starts with sales, not just product development.
The Future of Plain Sight and Smarter Event Networking
James has big plans for Plain Sight.
“We want to be the number one way event creators get paid,” he says. “Right now, sponsorships take 60 to 90 days to pay out. We’re working with finance partners to get organizers paid in three to five days.”
For athletes and entrepreneurs, Plain Sight is becoming a key tool—helping them maximize networking, host activations, and secure sponsorships effortlessly.
“I’ve seen firsthand that when networking is done right, it changes careers, businesses, and lives,” James says. “That’s what we’re building—a smarter way to connect.”
Join The Players Company or login to check out Plain Sight’s exclusive investment opportunity. To get in touch with James directly, send an email to james@plainsighthq.com. For updates on sports events with curated networking, as well as founder insights, subscribe to our newsletter.
