The Great Pivot 

For years I bought airline and credit card points and sold plane tickets for a living. In retrospect, my career choice was pretty ironic for someone with my background; I didn’t get on a plane until I was well into my beis medrash years, and didn’t travel internationally until I was 20 years old and heading to the Mir. I grew up in a simple family in Baltimore — even if midwinter vacation had existed at the time, my parents weren’t the type to go to Florida. The apex of my travel experience as a kid was driving Route 17 to the Catskills every summer to the bungalow colony.

But I was nudged into the travel industry after a few years of learning in kollel. Providing for our growing family was becoming difficult, and it was clearly time to look for a job. My uncle had a side hustle of buying and selling airline points and making first-class reservations for the wealthy (or “comfortable” as my mother called them). He took a chance and hired me to run his company.

We would buy up points from businesses that paid for products they needed with credit cards; we amassed millions of credit card points a year. We’d also buy points off individuals who were looking to trade them in for cash. Often those checks were made out directly to the caterer for their son’s bar mitzvah. It felt good giving these families an infusion of cash at the time they needed it. Other times we’d buy points off of bochurim who “churned” (opened and closed) credit cards for their hefty introductory point offers and then sold those points to us. I’d like to think these bochurim then used that cash to buy seforim they needed for the zeman, but we may actually have unwittingly helped start the 2012 Ferragamo-shoe-and-belt trend with the cash we gave them.

We would then “upsell” the points to people traveling to Eretz Yisrael and other destinations, allowing them to fly there in business class for a 40 percent discount. We used certain metrics to understand which airline and credit card point systems were most valuable, and I became quite good at picking winners. With millions of points between all of our accounts, we received the bonus of being able to travel ourselves, a luxury I didn’t have growing up. My wife and I took annual trips to Eretz Yisrael and saw some of the lesser-known parts of the world as well, places where I had to wear a baseball cap for extra safety.