When I was a kid, I didn't work. I got a tiny allowance ($5 per week, or maybe per month), and every now and then I'd age or undergo a holiday, so friendly relatives would send me money. But the only things I wanted to buy were desktop computer parts and video games, and I easily saved enough money for those. Parents took care of everything else–thanks parents!
Later, I was a college student. Sometimes I wanted to buy Chinese food, but that's about it; I still had roughly no spending. (Apart from how expensive school was, but again, I mooched from parents and scholarships–thanks parents!). Still, I felt like I should earn money, so first I worked as a dishwasher for around $8 an hour, and then as an inept ResEd student web developer for maybe $9.50 an hour. Suddenly the savings I had slowly built from that $5 per week allowance seemed meaningless.
Still feeling like I should be doing something career-related, I nepotised into a co-op preprofessional software engineer summer job at IBM. (Thanks Dad!) That was $20 an hour, full-time, with overtime even! After a few months of that, I came back to that student web developer job and realized I didn't care about it at all–I'd written more than my share of abominable Perl forms, and with $13,000 in my bank account, why would I want to get paid $9.50 an hour to write more of them when I had better things to do? I helped them hire a younger minion and lounged around on my coins. The money I had made from the web developer job also never mattered.
After college, George, Scott, and I started Skritter, and apart from rent ($300/mo) and food ($6/day), I had a few other small expenses (lasers, bowie knives, whips, etc.), but really, life was cheap. Skritter survived at first off of the entrepreneurship grant our school gave us (more mooching). I was finally glad I had made some money at IBM, because those savings kept me out of debt until Skritter could slowly become profitable. I could also calculate utility and buy a few things, like a sick office chair and some large computer monitors–they were like like three cents per hour of use!
Across several years of working on Skritter and moves to Costa Rica, Pittsburgh, and Sunnyvale, revenues grew, but my spending habits didn't change–I was still living like a kid who occasionally needed to eat something or upgrade his computer. If I had to buy something, I'd buy the cheap thing—I mean, you gotta save money, right?
This is a video I made on how to do the first skateboard trick you should learn, the Ollie!