After graduating from Penn State and following a stint in a PhD program at the University of Maryland, Matt Brezina and his roommate, Adam Smith, developed their first software company, Xobni, in March 2006, creating the first ever socially-aware email service. In just a few short years, the two were hailed by INC magazine as up-and-coming entrepreneurs while raising $40 million in funding and grabbing the attention of Bill Gates, who demonstrated their product at a Microsoft developers' conference.

After leaving Xobni, Matt took a vacation in Hawaii and developed the first concepts around a new mobile gifting company, Sincerely, while trying to keep in touch with family back home. Matt and a former-Xobni teammate, Bryan Kennedy, launched Sincerely in February 2011 and their first product, Postagram, launched in April 2011. Sincerely's products, including flagship mobile apps Postagram and Ink, allow people to create, send and share real personalized greeting cards and postcards from a mobile device, while leveraging photos and addresses on the device. The Los Angeles Times dubbed Brezina's 15-person start-up company as "Apple's chief rival."