Bobby has been helping out some people in his DMs on Instagram lately.
He recently became the food sponsor for an eight-and-under girls softball team from Iowa that qualified for a national tournament in Des Moines. The team’s organizers were raising money to cover meals during the tournament and were asking for donations from businesses and families. Rather than contribute a small amount, Bobby decided to pay the entire fundraising goal himself so the team’s meals would be fully covered during the trip. Bobby also brought up his recent decision to help a listener financially after the man reached out asking for help buying diapers while preparing for the arrival of a third child. Bobby had previously sent the man money and later gave even more after learning the listener had recently lost his father. The listener left a voicemail thanking Bobby for the help and addressing Amy who questioned whether the situation was legitimate.
After helping some people and organizations financially recently, his social media messages are now flooded with requests for money and sponsorships. The show then speculated about how often someone in Bobby’s position might realistically get scammed when donating to strangers online, with estimates ranging from a couple of scams to nearly half of all requests.