Bobby recently admitted to a little parenting fail: he thought he’d recorded the moment they told his wife Catilin's parents about the baby news… only to realize he double-hit the button and didn’t capture a single second. Cue the guilt. But it sparked a bigger conversation about the kind of parent he wants to be.
Growing up, Bobby has admitted over the years he resented people with money. That perspective is shaping how he thinks about what he’ll give his own child and what they’ll need to earn. He joked that his kid might grow up with a “jalopy,” a beat-up car straight out of humble beginnings, though Caitlin quickly shut that idea down. Amy reminded him he still has time to figure out the balance: giving opportunities without removing the lessons of appreciation and responsibility. It’s about finding that fine line between spoiling and teaching.
When the topic of paying for college came up, Bobby was candid. “Probably not,” he said, not because he wouldn’t help, but because their kids will likely be smart enough to earn scholarships (thanks, genetics!). Beyond that, he’s happy to invest in their education if needed because he believes education should be free for everyone.
But perhaps the most valuable thing Amy says Bobby can pass on? Financial smarts. Over the years, he’s learned about investing, budgeting, and managing money, knowledge which he can share so his child can navigate life confidently. At the end of the day, Bobby’s reflections show that parenting isn’t just about milestones or material things. It’s about teaching lessons, sharing experiences, and figuring it out along the way, sometimes with a laugh, sometimes with a little guilt, and always with love.