Swinging and Missing

Hello! As you may know, I wrote a book called “Hey Yang, Where’s My Thousand Bucks?” that comes out February 10^th. It’s a more personal and humorous account of my rise and fall and rise again to become the emperor. To get you to want to buy the book, here’s an excerpt that recounts my misspent twenties as a young, wannabe entrepreneur. Hope you enjoy!

The book is now available for pre-sale and I hope you consider buying a copy. Use code “UBIUBI” for 25% off. And I’ll be doing a book tour to New York, New Jersey, Connecticut, DC, LA, SF, and Seattle so come on out and say hello!

Chapter 9 - Swinging and Missing

Okay, I’ve been talking a lot about my spare time. What the heck was I doing for work and money in my twenties? Good question.

After law school, I was a lawyer at a big corporate firm, Davis Polk and Wardwell. Pretty soon, I had two thoughts:

1. I am getting better at this job.

2. I hate this job.

I went home for Thanksgiving to my parents that November and said, “You did not come to this country for me to do this. It’s mind-numbing.” My job at the time involved scouring hundreds of pages of documents looking for issues.

“What are you talking about Andy? You have a great job. We are very proud of you.” Ah, Mom.

“You shouldn’t be.” I joked with my brother that when we were kids I dreamt of going into the woods and killing a dragon, not being the fucking scribe.

So why was I doing this lawyer job? Aside from the fact that I spent 3 years in school for it, it had to be the money.

I’ve had something of a funny relationship with money. I guess we all do. My parents were suck-the-meat-out-of-the-bones stingy. My Dad still takes joy out of getting through a day without spending a dime because he’s found some free source of food.

When I was a kid, my Mom used to tell me how much everything cost so we would know how much she was spending on my brother and me. “You know how much this costs? You know how much that costs?” When I was a teen, I got fed up. I said to her, “How about this Mom, you can document everything you ever spend on me, and then when I’m older I’ll repay every penny, and then we can never talk to each other again.”

She was hurt. “Why are you so mean?”

“Okay, then if you’re doing it out of love stop talking about it.” I love my Mom.

Anyway, I’ve had a sense that I was going to need to work for money since I was a kid. As a teen I sold knives door-to-door – Cutco – and still remember the sales patter. Did I cut my hand with one of the ultra-sharp knives while cutting a bagel? Yes I did. Those things were a menace.

I worked at the school library at Exeter for $6.25 an hour. I was a snack bar worker frying chicken fingers at Josiah’s during my freshman year at Brown. It was interesting how classmates wouldn’t recognize you as soon as you put on a fast food hat and apron. I was a camp counselor during the summers.

Looking back, this was probably a little bit excessive. I was a middle-class kid. My parents at one point told me to work less and study more. But I always wanted to make my own money. I was on a partial scholarship to Brown from IBM but my parents often reminded me that they’d taken out a second mortgage on the house.

This extended past college into law school. When I was a 2^nd year I got a summer associate job at a big firm. We were given a lunchtime reimbursement of $50 if we ate with a current lawyer. I know, it’s a lot of money, and everyone used it to eat at fancy restaurants. One time I went to lunch with a couple of associates and they picked a fairly normal restaurant. The lunch entrees were ‘only’ $17 each, so I ordered two of them.

Everyone at the table was like, “What are you doing?”

Embarrassed, I said “Oh, I’m just really hungry” when the truth was I just wanted to make sure and spend all $50. Who wanted to leave money on the table?

I sensed everyone’s eyes on me. I had to eat two lunches to avoid making it a thing. I moved the items around the dish to make it look done by hiding some remaining food under some mashed potatoes.

After law school I owed $110,000 in school loans. The firm I joined paid $120,000 plus a bonus of $45,000 to start. It seemed like an absurd amount of money to pay a 24-year old who hadn’t done anything and didn’t know anything. It was more than my Dad made, and he had generated 69 patents for GE and IBM. I felt like I was way too young to be making that kind of money but also that I shouldn’t feel too committed. I didn’t have kids, a mortgage or even a girlfriend. Whose dreams was I supporting?

So I left the firm after five months to try and start a dot-com company. Stargiving.com would raise money for non-profits, where if you clicked on an ad you’d help the charity and then maybe meet the celebrity. My parents thought I was a moron walking away from a six-figure job for my longshot little start-up. Turns out they were right, as we would throw in the towel about a year-and-a-half later.

I felt like a failure, lying on the floor of my little bedroom; I had moved in with my old doubles partner Andy to save money and was paying $1,080 a month. I had gone through my savings. My classmates were still making six figures practicing law. I had a net worth of negative $100,000. But I wanted to get better at becoming an entrepreneur.

I got a job at a mobile software company that ran out of money a few months later. One of my colleagues moved into the conference room with duffel bags of his stuff and was showering in the office. “You’re living the dream!” I said to him, trying to be positive. He glared at me. I found another job working at a healthcare software company that made health records digital.

Given that I’d by then been a part of two companies that had gone under, I started looking for side hustles. I tutored students in standardized tests. I also began promoting parties under the name “Ignition NYC” with a few partners. We would throw big parties in Tribeca.

Throwing parties started with a simple but compelling question. A friend of mine asked me one night as we shared tales of rejection, “How do we become cooler?”

I answered, “We throw parties.”

He said, “We can’t do that, we live in tiny apartments with roommates. That won’t look cool.”

I said, “Then we use a lounge or bar. If we get enough people, they’ll let us use it for free.”

The reality was even better; if you got enough people to show up, the bar would actually pay you a percentage of the bar and give you some drink tickets. You could throw a big party and give free drinks to your friends and even make some money if you could get a couple hundred people to show up.

That didn’t seem that hard for a 26-year old in New York City. I enlisted a few partners. One was Mike Skinner, Miika’s roommate in Brooklyn who was the drummer for his band. Mike was cool. The other was Amy Engelhardt, who had grown up in the town next door. Everyone had a crush on Amy. The last was Gunny Scarfo, our resident tech guy.

If you want to become an entrepreneur, it turns out throwing parties is a great way to start. We had some phenomenal parties including one that drew 500 people on New Year’s Eve in 2003. Everyone was desperate for something good to do on New Year’s Eve, which is a holiday everyone secretly hates. Sort of like Valentine’s Day.

I had three jobs for about 4 years; healthcare startup guy, tutor and nightclub promoter.

I was single for just about all of these years. One problem for me on dates was that I was very frugal. I lived on protein shakes and yogurt, so it was tough for me to switch gears to treat a woman to a nice meal. Look on the inside and believe in me, ladies! When I met a woman who didn’t like me I thought it was because I wasn’t successful enough. Meanwhile it was probably just me being insecure or a cheapskate.

Did I mention that I still owed six figures in law school loans? I started calling my loans ‘my mistress’ because it felt like I was sending checks to support a phantom family in another town. I hoped they were living a good life.

As you can tell, the book is a bit different for me and tells stories I never could before. I hope you check it out and pick up a copy!

The book is now available for pre-sale; use code “UBIUBI” for 25% off. Book tour dates in New York, New Jersey, Connecticut, DC, LA, SF, and Seattle can be found here. Go to noblemobile.com/yang for 3 months off your wireless bill, the best deal around. I’m also celebrating my bday on Jan. 15^th at our Offline Party in NYC so come find me there!