GRAND RAPIDS, Mich. (WOOD) — A heartfelt homecoming turned into a day of giving as entrepreneur Chris Sain Jr. kicked off his “100 Days of Giving” campaign Tuesday, surprising two Grand Rapids nonprofits with generous donations—and inspiring hope across the community.
Sain, who grew up in the Baxter neighborhood of Grand Rapids and has family roots in Wyoming, returned to his old neighborhood with purpose. His first stop: delivering a $25,000 check to Endless Opportunities, a youth mentoring program that plays a vital role in supporting local kids facing uncertain futures.
“In the nonprofit world, everyone’s searching for funding,” said AJ Hills of Endless Opportunities. “Given the current climate, it’s unclear who’s funding what. For Chris and Corinthia to come in and plant a seed in our program—it’s nothing short of amazing.”
But Sain didn’t stop there. Just a short drive away in the Boston Square neighborhood, he handed a $10,000 check to Positive Impact for Life, a mentoring and tutoring initiative focused on youth education.
“Usually, we get left behind,” said founder and CEO Malique Grear. “I was in awe—grateful, shocked, and deeply appreciative.”
For Sain, now a successful entrepreneur and author, the mission is personal. His goal: uplift organizations that are often overlooked but doing powerful work on the ground—especially those helping at-risk youth in communities like the ones he grew up in.
“There are so many great people and organizations doing the right thing—but too often, they go underfunded,” Sain explained. “Because I’m in a position to give back, and I know these neighborhoods and what they need, I wanted to invest in the people and their work. I believe in their missions—just like they do.”
The impact is immediate. The donation to Endless Opportunities covers roughly 20% of its annual budget, allowing them to run vital summer programs that guide students toward career readiness. At Positive Impact for Life, the funds will boost summer reading programs and fund a new tutor position.
And this is just the beginning.
Sain’s “Pull Up Season”—his 100-day journey of surprise giving—will continue, with 99 more days of donations to nonprofits and small businesses that are making a difference.
He has a message for community organizations in Michigan and his extended network in Wyoming: “Stay ready. You never know when I’ll pull up next.”
