
2026 Midlife Entrepreneur Grant Winners
Our Grant Winners
PAM JACKSON
Dip N' Double Ice Cream
Pam Jackson is the founder of Dip N’ Double Ice Cream, a Chicagoland-based mobile dessert experience brand known for premium service, fun energy, and community connection. After a long corporate leadership career in operations, people leadership, and customer experience... more
MANDY GILES
Parents of Trans Youth
Mandy Giles (she/her) is the parent of two transgender young adults and is a fierce advocate for transgender and gender-diverse youth. Leveraging more than two decades of serving children through educational nonprofits, Mandy is the founder and CEO of Parents of Trans Youth... more
RONDA BILLING
RDay Cake Creations
Ronda is the owner of a custom cake shop dedicated to creating beautifully designed cakes that celebrate life’s most meaningful moments. Through both custom orders and interactive decorating classes, Ronda and her team provide memorable experiences that bring people together... more



