I didn’t know it at the time, but what followed was a period of 5 years where I had no stable income in New York City. I couldn’t get a job no matter how I tried but I kept building things. I delivered for Papa Johns. Turns out I have been undertipping pizza delivery. I went to small stores and checked for Coca Cola branding placement. I did background acting work. I bought a bunch of film equipment and eventually got a coding bootcamp to pay me $300 to make them a commercial. An entrepreneur paid me a few grand to be “CEO” of his statistics app. At one point I recall having a major fight with my roommate at the time over him rounding down 30 cents on a bill we split.
I learned to live with few items: https://mrsteinberg.com/when-to-be-minimalist/
But I needed money fast. I was now slowly building credit card debt and the interest payments were starting to balloon.
Another one of the companies I started, Trusu, got into Y Combinator. Last time I got in we raised $1.7 million in a weeks. All we had to do was get to demo day and we would raise enough for me to pay myself.
We raised a total of $10,000 at demo day.
We had some runway left so we flew back to Hong Kong where we were based and tried some crazy deals like free international shipping over a certain amount. They gave us more customers and traction but we were steadily losing money. Realizing we only had a few months left, we went over our finances.
There was a mistake. We didn’t have 3 months of runway left. We didn’t even have enough money to keep operating today or pay any of our debts off.
I had been purchasing the goods on my private credit card. I had $90,000 of credit card debt and no way to pay it off.
I was royally fucked.
I flew back to New York and tried to find a job ASAP. I wasted the last 5 years of my life.
I interviewed at Facebook yet again and made it to the final interview.
Rejected again. I was up to 400 applications and 80 interviews without an offer.
I decided my worth was at least a $150,000 salary. Nobody even gave me an interview.
I decided my worth was at least a $120,000 salary.
Nobody would interview me for that either. I wasn’t going to work for anything less damn it.
I lowered my salary expectation to $100,000. And after no takers to below that.
Finally jobs interviews. Interviews where they don’t do Leet Code puzzles (I suck at those).
I got an offer for $80,000 and took it right away. Then I kept applying and found a second one for $80,000.
This was before covid though. Jobs weren’t remote. I had to be in person in Manhattan at 2 different offices 20 blocks apart from eachother.
For the second one, I asked to just be half time for $40,000. I didn’t even need insurance or dental, after all the first job covered. That would at least put me at my goal of $120,000 and a slightly more manageable 60 hours a week. The second job accepted these terms.
I needed to pay off this debt!
I don’t know if you’ve ever had an $80,000 coding job in New York, but they aren’t that hard. This seemed like below entry level payment. I am fairly certain people work far more than 60 hours a week for much less than I was making. The issue was the stress of context switching.
Neither company was even close to the same field as the other. One was a social B2B app and the other was a crypto rewards app.
What followed for the next 8 months was a whirlwind of context shifting. It reminded me of those 90s sitcoms where the guy accidentally agrees to two dates at the same time and he has to constantly switch between them.
On my lunch break I would run 20 blocks to the second job. Then I would say I have to use the bathroom and run 20 blocks back. I was a sweaty mess.
Going back to one job after this was a walk in the park. It’s take a lot out of you to constantly remember and hide things and do 2 things at once. I decided to just block times and not respond to one job if they ping during that time. These days you could just do it from a coffee shop remotely with much less stress.
Neither provided me a work laptop either. So I had to install and switch between different Xcode Versions, node versions, everything! It was annoying.
But both companies were happy with me. I was by far the most experienced developer at both companies. I had my dream salary.
In the mean time, I kept my side projects and our startup running…