This post is a prequel to stories & lessons from the Fed & SoFi and later at Square.
Soccer
I played soccer for ten years. Mostly sweeper – the last line of defense before the goalie. My job was to shut down the offense when they broke through. Near the end of my soccer career in high school I pivoted to swimming year round since it was clear I wasn’t good enough to even make varsity. However, my favorite memory of strategy was in a soccer tournament when I was 9 or 10. We noticed one team that kept winning always had really high scoring, like 5 to 3. Our theory was that they were a mediocre team on defense, but had one offense superstar. When we started playing them, one kid almost scored in the first 2 minutes – it was clear he was their star. We put 3 people on him the entire game, shut him down, and won handily. But we also made him cry during the game. It gave me a sour taste of winning in situations where someone had to lose. However, he later reached out and we ended up somehow playing together with him on our team. I’m glad the story ended better than when he was just a foe we had vanquished.
Soccer Referee
This was my first real job (I was 11, though apparently today you have to be at least 13). I had to pay and get trained to be certified, so it was my first taste in investing in myself to earn some money (I could make close to a hundred dollars with a weekend soccer tournament, which was very good money for Pokemon or MtG cards). I also learned about power, responsibility, and being liked vs respected. While a referee was needed to have a game, people were merciless when you made a mistake (or a perceived mistake). It was also better to be firm on a bad decision than to waver or show you could be convinced otherwise, which opened up a floodgate of complaints. Everyone wanted to win, and would often blame the referee when they lost. It was my first experience having a crowd booing me or a grown man threaten me in front of his child. But a few people after the game would say I did a good job. It was little kindnesses that made it bearable, but I only lasted a year or two.
Vending Machines
This is more of a hobby, but I would crawl under vending machines when I was 8-12 or so to get coins. It was dusty and dirty, which was the ‘cost’ of doing business, but I would sometimes find as much as $5 in change under there (not too bad!). It made trips to home depot and other stores more exciting – like exploring little treasure chests with varying degrees of loot (also it was fun trying to not get caught doing it. I wasn’t really embarrassed, but I would get some odd looks).
Toy Aliens
When I was ten or so I liked buying these little one inch rubber toy aliens in vending machines. I bought them for 50 cents. I would bring them to school and realized some kids wanted to buy them. I sold them for a dollar and made a profit, which I used to buy more. It went on for a little while but eventually my local market got saturated and I didn’t bother finding something else to sell or expanding my market.
Trading Cards
MtG, Pokemon, and Yu-Gi-Oh! were my favorite. I would trade cards with friends sometimes. One time I traded with someone I just met for a card they didn’t have on them. They promised they would come back next time and give me the card they owed me to complete the deal. I said okay, despite my parents warnings. They never came back, or maybe they did and couldn’t find me. Either way, I realized I needed a way to contact them or make sure the deal actually happened. It was, in retrospect, an inexpensive lesson in trust and making sure everything for a deal was ready to go, but it still hurt.
Starcraft
I played computer games since I can remember, but Starcraft 1 was my first deep obsession when I was 13 or so. It taught me about resourcing strategy (macro), combat tactics (micro), and avoiding foolish mistakes that cost me later in the game like getting too hung up on one path (e.g. getting too focused on defense or building resources) as well as gathering info on the enemies strategy. One summer I remember playing it until 7 in the morning, sneaking past my mom going to work so I could go to bed. I hit my limit when I realized that skill progression depended heavily on click speed, good internet, and the right tools—not just strategy.
Helping to build a House
My parents spent about ten years managing an investment property starting when I was 13 or so. The original plan was to fix it up and sell it quickly but they later had to tearing it down and rebuilding it from scratch due to finding unexpected asbestos. My main lesson was not to get into real estate…. it took so much unexpected time / effort / money for so many little things – but it also showed me how to work construction / how a house is built / how to work with the occasional contractor (my dad did most of the work himself). I remember my dad sometimes gave ambiguous instructions, such as telling us to ‘pick up stuff in the yard, like this can’ – when there were no other cans in the yard. I thought he meant garbage but it turns out it was anything above a certain size, so largely rocks. Also, I learned how important it is to brace concrete pours more than you think you’ll need. You do NOT want to have to clean up wet concrete that spilled all over the place / broke out of it’s mold. Also, for me, I’d consider it much better to have money and contractors/people you can trust than the knowledge/experience of build a house.
Janitor
My dad ran a small mental health nonprofit. I cleaned it every weekend or so for a few years (vacuuming, cleaning trash/spills, toilets, etc) after my sister went to college. It was decent money since I worked for my dad ($45 a week) – feeling almost like an extension of random household chores (and unlike household chores, doing good work didn’t lead to more work – since the work was more clearly defined). I see why people didn’t want to do this job, but I found it unexpectedly satisfying to clean things up / organize stuff. The routine was nice and I’ve always found chores oddly comforting sometimes (i.e. work which needs to get done where I can see the impact of my efforts immediately).
Stock Trading
At one point I started exploring different investments and stocks, after reading some books when I was 14 or so. I remember looking at seasonal patterns and trends of some blue chip stocks. I think I put $700 (all my money I had earned) into 3M and made about a $200. But the stress of having all my money in one place, obsessing about the stock, and realizing how little I could control made me avoid stock trading or any form of active investments going forward as it felt too much like gambling. Funny enough I ended up selling in 2007, just a little before the 2008 crash (though long-term everything recovered). Even though things worked out, the stress of active trading was too high and dependent on luck – passive index funds were better. Reading about finance (and some discussions with my mom) also made me realize it was very important to have a clear understanding of my financial situation and to avoid debt with high interest as much as possible.
High School
I didn’t start really trying hard at school until sophomore year when I started getting a C in math (in the past I could get As fairly easily). I decided to make a strategy and focus. I bought a planner to organize my to do list – I wanted to make sure that I didn’t not get an A for something preventable like forgetting I had to do some homework. I still use a planner/notebook to track my work nearly twenty years later. I also saw some people overwork at school, staying up all night to make sure they got every problem correct. I tried to balance routine/sleep (due to the impact on my sports performance), and got everything I could get on the homework and if I got really stuck on a problem, ask for help. It saved me a lot of time to ask for help (and learn who to ask), but ultimately I was responsible for getting all my work done and taking the grade I could get.
Eventually I learned how to ace math tests by studying previous tests and making sure I fully understood the homework concepts. I also learned how to memorize things when I needed to (e.g. writing everything I had to know on a blank sheet of paper again and again), and how to hack certain tests and guess well (e.g. any SAT question that says ‘always’ or ‘never’ is usually wrong in multiple choice). It was more important to be able to pass tests than gain knowledge, unfortunately. Learning was difficult but I figured out how to be consistent with my routines and work very, very hard (while navigating burnout) to make sure I set myself up as well as I could for college applications from my big public school. My last two years of high school might have been the hardest I’ve ever worked towards my goals in my life, often getting up at 4am to swim and finishing homework in the evening before bed after a long day. I was a machine, but in retrospect I was also very lonely and sometimes wished I was more social and had enjoyed my time more. Especially with such kind and funny classmates, where I was more of a chameleon socially go broad and shallow rather that forging deeper connections.
I also started studying economics in 2008, which I always found funny to start learning macroeconomic theory while finding out that theory was being actively disproven daily in the news (fortunately I had a really good teacher) – it gave me the sense that no knowledge lasts forever and there were some things no one really knew.
I got rejected from all the Ivy League schools I applied to, and only got into Carleton, Williams College, and UChicago (early admission). I settled on Williams since it had the most grants and was the furthest from Minnesota (where I grew up) – I wanted to see more of America. Up until this point in my life, my college essay on swimming was probably my best writing by far (it got a lot of review from family), otherwise I was pretty mediocre if I’m being honest. My skills were moreso strategic planning and sustained effort.
Dining Hall Worker
In college I worked in a dining hall for one semester. However, I realized that $8 an hour or so wasn’t worth the time when I could focus on studying/networking/sports and tuition was >$50K (though it was mostly covered by grants and some loans). I liked parts of the work, and having some spending money, but I just couldn’t justify it – it would be better to just take a slightly larger loan before graduating and pay it back when I was working full-time.
Economics Research Assistant
This was my last formal job before graduating college and the closest thing I had to an internship. I had a good relationship with the professor and had fun learning and chatting together, but got VERY bored with the data entry. It wasn’t particularly challenging, but let me stay on campus during the summer which was fun. It also showed me that when someone had the resources to sponsor an internship and wanted to work with me could very easily make it happen – which I was very grateful for.
College
The best description I’ve heard of liberal arts is that it teaches you nothing but prepares you for everything. I learned how I learn, how to apply concepts across disciplines, how to understand the limits of what I could understand. I majored in Economics and Math (a combined 18 of 36 classes), but also took classes in Chinese (8), Psychology (2), English (2), Environmental Science (1), Computer Science (1), Philosophy (1), Music (1) and some fun winter study courses on samurai and horror films (2). I met the love of my life (my spouse) in college, along with many friends who now live all over the world.
In high school I learned how to work hard, be strategic, well-rounded, and organized without burning out too much – but college made me much smarter by questioning my fundamental premises and identity while expanding my capacities. College was a mixing bowl of experiences, identities, and beliefs. But by the end, I burned out on academia and the small town environment. But at its best, college gave me some of the best days of my life. I was in awe of the resources there and level of talent in the students in so many different areas (music, theater, sports, etc). I’d see a national champion tennis player give a solo violin performance that made people cry in the audience or a star mathematician do genius improv comedy. I felt like I was at a super hero training camp.
Beijing, China Study Abroad
For six months in 2011 I lived in Beijing in a study abroad program where we only spoke Mandarin (no English). Within a week I started dreaming in Chinese and even ten years later I would have the odd dream in Chinese. My time there gave me a deep respect for different cultural backgrounds and how much they can shape perspectives. I also learned a deeper sense of self often through some self-destructive tendencies culminating in a broken foot and surgery in a Chinese hospital (where I first learned how to meditate deeply).
Swimming
For eight years, I attended my high school and college, but I lived for swimming. That often felt like the real subject I was most passionate about (blog post on my final swim race). I loved the feedback from repeated trials – every pool was the same distance, but I had changed every time. I had so many chances to reduce my race times and perfect my stroke. I remember learning that Ian Thorpe was faster than Michael Phelps, BUT Phelps had a faster time because of his underwater kicks and better turns and starts, so I practices those relentlessly. I visualized races all the time and spent years thinking of optimization, swimming pretty much year-round. I liked that I could sometimes lose the race, but still get a best time and feel good about my achievement. I loved relays the most.
Through swimming, I learned how to take better care of myself and establish a good sleep and eating routine to be able to maximize my effort over time training in the pool. I learned technique and my body’s weaknesses (e.g. I found out in college my glutes were relatively weak, which caused knee pain, so I learned and strengthened them directly and haven’t had knee or back pain since – article – apologies for the website…). I learned subtle things from underwater videos, like my head was too high up, which moved my legs down and slowed me down at top speeds – training my all-out sprinting with proper head position made me even faster. My parents were very supportive of me, often driving me to practice early in the morning. Even 16 years later I still have my high school 50 free record (21.85), and by my senior year I was on two college relay records. I debated becoming a physical therapist for all the wisdom I learned about my body – but ultimately didn’t pursue that career path.
After I graduated I lost a huge part of my identity as an athelete that took many years to recover from. I had reached the highest level I was going to reach in athletics at 20 (D3 NCAA Finals) – and was ready to be done competing for athletic achievements. Years later I also realized that sports are not always healthy, since they are about winning more than balance. Now I do a lot more yoga and pilates – but swimming will always be a major part of my life and development, where I learned what my body was truly capable of. At a recent reunion (2024), I found out I could still swim a 50 free in 24.1 seconds (~3 seconds off my best time), after 11 years without swimming.
This series continues with Stories and Lessons from my Career at the Fed & SoFi (Before Square) and later in my career at Square.
Daeus Jorento 