All the Hacks · Wednesday, September 16, 2026
Chris Hutchins shared how he first got into the world of points and miles, sparked by a college spring break trip to Cabo. He recounted how his father's frequent travel led to early frequent flyer accounts for him, which eventually enabled him to afford the trip he otherwise couldn't have.
“And then I looked and I had enough American Airlines miles from flying on trips with my family and other things, because I didn't sound like I was traveling for work in college. To buy the ticket to go on this trip that I wouldn't have otherwise been able to go on.”
“And I was like, This is awesome. I need more of this. But then I used all the points. So I need more of these points. Because I don't want to miss out on another trip like this in the future.”
“So I think that was like when I started playing things. Like if I look at Amex, you know, it's like member since, you know, it was 2003. Nice. So I was 19. So I know I got into the miles and points game, you know, before graduating college.”