Have you heard of the Venmo Challenge? People ask their followers on social media to donate less than a dollar each (which really adds up after a while!), then they give that money to someone in need. Brittany Jill is no stranger to the Venmo Challenge, and this time around, she's giving the money to a waitress in Wisconsin. When Brittany surprises the waitress with a generous $750 tip, she breaks out in tears of joy.