Did you know Pope Francis’ first job was working a bouncer at a nightclub in Buenos Aires? The unpredictability of that trajectory is one reason why we love hearing about first jobs — they are a window into an earlier and often unrecognizable version of one’s professional self.
While first jobs are far from reliable predictors of future income and career prospects, they often reveal early passions, interests, and foundational career lessons learned — all of which can play a role in shaping one’s future.
Our CEO Dave Girouard recently talked to Reuters about his first job working at an ice cream shop, which got the rest of our team talking about their first jobs. Check out how each of us got our start and join the conversation on Twitter @upstart using the hashtag #firstjob.
Jeff Keltner, Head of Growth First job: Hanging and framing art
“I spent a summer in high school working at an art gallery hanging and framing art. My Mom sent me over there because I got on her nerves, but it turned out to be unpaid. I still have the lithograph they gave me at the end of the summer.”
Alison Nicoll, General Counsel First job: cashier
“I worked as a checkout chick at a local supermarket. It was just a job, but it did keep me fashionably clothed during my high school years and paid for my first trip abroad traveling sans family.”
Cindy Smith, Operations Manager First job: cashier
“I worked at the oldest store in Chinatown, Mott Street General Store. I stocked the shelves, worked the cash register and helped customers. I was the only female at the time and learned a lot about Chinese trinkets.”
Paul Gu, Co-founder & Head of Product First job: playground assistant
“I was a playground assistant at Makutu’s Island, an indoor jungle gym. Each day, I printed 100 SAT vocabulary words on a small paper and sneakily studied it while on the job. It wasn’t the best paying job I ever had, but it did get me into college!
Ryan Randall, CFO First job: waiter
My first job was waiting tables at Leatherby’s in Fremont. I started my junior year in high school and worked evenings and weekends delivering sandwiches and ice cream to very happy customers. It was an amazing introduction to focusing on the customer.
One day I had a table of eight for a birthday party. They came for lunch and ice cream sundaes for the entire family. I was able to serve everyone quickly and was bringing the final sundae to the man celebrating his birthday with his family. It was a large black and tan sundae, which is basically a fountain glass overflowing with caramel and chocolate. As I approached the man, I could feel the glass begin to slide of the plate. I tried to set the sundae on the table, but it slipped from my grasp and landed right on the face and shoulder of the birthday boy.
Needless to say, I was aghast and quickly offered to pay for his laundry and his entire meal. Luckily for me, he was very good humored and told me not to worry. Further, he would not let the owners pay for his cleaning, paid for his meal himself and give me the best tip I had ever received up to that point. My takeaways were twofold: 1) always wipe the extra toppings from the bottom of the sundae glass, and 2) always give the best customer service you can and quickly correct any mistake that may happen.”
Simon Lepkin, Engineer First job: tutor
“As a Senior in HS, I tutored a roomful of “smart but struggling” Freshmen in math and science. I liked it a lot! I later learned that teaching a classroom full of students is way way harder than tutoring them.”
Vishal Maini, Growth Manager First job: conducting marketing surveys
“In high school, I conducted marketing surveys on TreasureTrooper.com for a few cents each, so that I could get money in a PayPal account and use it to pay for membership and items in some MMORPGs (massively multiplayer online role-playing games). I used to play 6-12 hours every day - first Runescape, then Knight Online. When I finally quit, I gave away most of my stuff to friends, and then sold my itemless character for about $170.”
Viraj Navkal, Data scientist First job: photo developer
“When I was 16 I worked at a photoshop developing photos. My most vivid memories from that job are the smell of the photo chemicals, the customers who submitted photos with things I should not have seen at that age, and the guy who bought the shop and slowly replaced its employees (and, eventually, me) with members of his extended family. Upstart is a huge upgrade :) “
Jonathan Eng, CTO First job: tutor
“My first job was being a tutor for middle school students. I would help them learn math, science, and english. My most challenging case was a student with a brain tumor.”
Anna Mongayt, Co-founder and Head of Operations First job: piano teacher
“I learned to play piano when I was four. So when I was in high school, I started giving lessons to little kids ages 3-6. By my senior year, they were good enough to hold their first little concert. It was a great way to teach make a little spending money while introducing kids to doing something I loved.”
Brigitte Bradford, Marketing Manager First job: camp counselor
“In middle school, I would help at an equestrian summer camp. I would help get the horses ready, teach lesson and do demonstrations. Many of the campers were older than me, so to help establish their trust in my experience and ability to teach, I would do emergency dismounts and jump course demonstrations on the first day of each session.”