Throwback Thursday: That Time I Tried to Work for Donald Trump

Growing up in the suburbs of Cleveland, Ohio I tried to make money where I could, or as some may say, I ‘hustled’. I’m not the biggest fan of that word and while I’m on the topic of words I dislike, I also don’t like ‘disrupt’ as it too has been grossly overused. Particularly due to all the ‘hustlers’ ‘disrupting’ every industry known to man in Silicon Valley. You know, like that new company, that is the Uber of (insert anything here).

I shoveled driveways, mowed lawns, charged kids to see my magic tricks at recess, I even worked at a magic shop. I was so young they couldn’t pay me, I was under the legal age to work. Instead, the arrangement was I’d take a trick home as my compensation or sometimes a book on magic tricks. I opened my first savings account in 1992 after my Grandpa explained to me what interest was. I was in the second grade and after my birthday party I told my mom, “I want the bank to pay me interest, can I go get a savings account today?” I remember my birthday cash being spread out on the couch. I emptied my mickey mouse tin can where I stashed my other money and I had a total of $350 I saved up over a few years. Later that day we went to the bank and opened a savings account and I couldn’t wait to deposit more! At times I’d ride my bike by myself 2 miles just to deposit $7. Looking back it was like something out of a movie. A 7 or 8 year old kid parking his bike in front of the big window at the bank, walking in, stopping by the counter to fill out the deposit slip, and then standing in line surrounded by adults — tall people. That summer, Sue, the branch manager, started calling me by name because I was coming in so often. I loved that but not as much as I loved the 6% interest I was getting on my money! Ah, those were the days.

I played sports year-round, Football, Basketball and Baseball, but always worked whenever I could. In the summer of 8th grade I started working at an Italian restaurant washing dishes. I recall after my first shift asking to speak with the manager. I felt like I was being cheated. I was far more efficient at getting the tubs of dishes cleaned than many of my coworkers who were slacking off while I did all of the work. So I did what any reasonable dishwasher busting their hump would do, I asked my manager for a raise! That’s right. After 6 hours on the job I asked for a raise and I got it. That took me to $5.25/hour. Throughout high school I held several jobs from McDonald’s to Best Buy to an AT&T Cell Phone Kiosk. My senior year of high school I worked at MBNA where I got my first taste of a bonus check. I was a telemarketer slangin’ credit cards. (My apologies if I interrupted your dinner back in 2002.) As a high school kid, I was making around $1,500–$2,000/month — part time. MBNA taught me a lot about sales and for how horrendous of a job it was, it actually was one of my favorite jobs. Sounds crazy to say, but it’s true. It was there I learned that the people you work with can make or break a job. Shout out to Matty I, my manager, who talked me into staying when I wanted to quit after the first week!

My parents paid for all of my college. (Thanks again Mom & Dad) After my freshman year, I lied to my parents and told them I was going to work part-time to make some extra spending money. They didn’t have a problem with me working as long as my grades didn’t suffer. The lie was that the job wasn’t part-time, it was full-time. By choice, without student loans in my future, I chose to work full-time and go to school full-time. Once into my major, I loaded up two days a week where I’d go to classes from 7am to 6 or 7pm. That meant there were 5 other days in the week where I could work, and so I did. It didn’t have much of an impact on my social life, in fact, I’d argue it helped fund a better social life. I had more disposable income than most kids, or even recent college grads for that matter. I worked for Nextel and then Sprint once they acquired Nextel. They did tuition reimbursement too! So now I was working full-time AND getting a tuition reimbursement check each quarter. I sent my parents on two great vacations, one year for their Christmas gift I sent them to New York City, the next Christmas to San Francisco. They hadn’t been to either place and it felt good to give my parents a gift that they’d remember forever. My parents are typical midwestern folk. They’ve worked at the same jobs all their lives, live within their means; and it’s not that they couldn’t afford the vacations on their own, but I simply had to force them to go explore. I booked both trips and said, “take off work these days, the trip is paid for, you’re going!” My parents wondered how I could afford these gifts and in one breath I told them I had lied and that my part-time job was really full-time, and in the next breath I showed them my grades and how they actually had improved each quarter. I didn’t get smarter, I just became much better at managing my time.

As a college senior (06') I recall sitting at my computer looking at jobs, but nothing really jumped out at me. As a regular viewer of The Apprentice, I remember thinking to myself, “If I can make it on The Apprentice and win, that’s a solid start to my career.” This was the 6th season, and a couple years prior they introduced a new theme to the show, “book smarts vs street smarts” (contestants with college degrees vs those without); I began to think, “what if they do some kind of theme like ‘Rookies vs Vets’ where they had some recent college grads compete against industry veterans?”

I was an Economics major at The Ohio State University and had done several internships at MBNA, which was later acquired by Bank of America. I never really had a clear cut career path in mind. Business interested me and I had some success with sales early in my life. From shoveling driveways as a kid, to selling cell phones and credit cards to brokering my first real estate deal as an unlicensed college student. This was enough to convince myself to book a last minute flight to New York City to try out for The Apprentice.

I remember this trip so vividly, it’s hard to believe it was exactly 10 years ago today! It wasn’t my first time to NYC, so I knew what to expect, but this wasn’t vacation, this was all business! Tuesday Night, technically Wednesday morning, around 1am (March 22, 2006) I booked the cheapest flight I could find. It was for Thursday, March 23rd at 4am departing out of Columbus to Philadelphia with a connection in Detroit. I know, such a crappy flight! My friend Pete lives in Philly so I knew I could crash with him.

I arrive in Philly around 4pm on Thursday and we grab an early dinner. After dinner I shower at Pete’s place and put on my suit and red power tie and head to the train station. These details I feel are important to the story, so bear with me… A year earlier on Ohio State’s campus they held an Apprentice casting. I tried out. I showed up around 5am the morning of the casting and there was already 100 people in line. The official start time wasn’t until 8am and yet there was a long line and again this was Columbus, Ohio — NOT Donald’s home turf, Trump Tower. My thinking going into The Apprentice casting in New York was the following, “Donald Trump will be there, the casting is in Trump Tower and this is New York City! I better go plenty early!” It was my first time on the New Jersey Transit, here I am in my suit, with a laptop bag (without a laptop in it) but I had several copies of my resumé ready to go! I get to Penn Station (12:05am March 24, 2006) and get a cab. “Trump Tower Please.”

I arrive at Trump Tower at 12:20am and without hesitation, as if I lived there, I go up to the main doors and I’m quickly met by a large security guard. He asked me what I’m there for and I tell him, “I’m here for The Apprentice.” I’m still standing outside while this dialogue is happening, the security guard has the door half-propped open against his back and replies, “Congrats you’re the first one here, but you’re about 8 hours early stand along that wall over there.” As he says ‘over there’ he points to about 50 feet behind me, outside. It’s March at midnight and 30 degrees, I’m wearing nothing but a suit. No overcoat. No gloves. No winter hat.

I’m standing outside by myself in Manhattan at 12:30am and I begin to pace the same 10 foot by 10 square of concrete in efforts to stay warm, or at least prevent myself from feeling numb. Around 1am a Rolls Royce pulls up, and the driver rolls down the window and shouts at me, “are you the first in line for the Apprentice?” and I say “yes”. No further questions, the driver rolls up the window and speeds off. Now around 1:15am or so a few people have arrived. We begin chatting about our backgrounds, the common question I keep getting over and over is “Oh you’re the first person here, what time did you get here?” Around 1:45am a guy in his mid to late 30’s comes up to me and says, “you remember that Rolls Royce that pulled up here about an hour ago? I said, “yes” he said, “I was in the back seat, I asked my driver to ask if you were the first person in line because I wanted to be the first person in line.” I said, “oh, well, sweet car man!” (We don’t see too many Rolls Royces in Ohio) He said, “I’ll give you $1,000 right now, if you let me take your spot in line.” I quickly fired back, “Sign over the title to your Rolls Royce to me and you got yourself a deal” we shared a chuckle and he said “no, but seriously you really won’t let me take your spot in line for $1,000” I said, “no thanks, but if you don’t mind me asking, what do you do?” he said, “I work at Goldman Sachs, you?” “I’m a college student.” He literally laughed at me and proceeded to the end of the line.

Around 5am someone from Trump’s camp came out and asked me if I was willing to come inside for a few minutes to participate on the radio show that was broadcasting from inside Trump Tower. Of course I would! And if for no other reason, I couldn’t feel my toes! Around 6 or 6:30am Trump comes outside surrounded by his security team and in typical Trump fashion it took all but 12 seconds before you hear him say, “Isn’t Trump Tower beautiful, wait til you see the inside.” He continued, “wow, the line is wrapped around the building, I’ve never seen anything like it, do you believe this.” He makes his way back up to the front of the line near me and that’s when the woman I spoke with earlier says, “ok, we’re going to go do the radio show now, follow them” and she points to Trump and his security team. I was escorted inside to the table where the radio show was taking place. They spoke with Trump first and then brought me in. I had the opportunity to talk about myself a little bit as well as mention how I turned down $1,000 for my place in line. Trump said, “well you sound sharp and look at his tie, he dresses sharp too.” We had similar solid red ties on that morning, and this couldn’t be going any better. After the quick radio segment, I was whisked back outside by a security guard into the cold for another hour before they began to let people inside to begin the casting. I had several news reporters ask me for a statement and I could see the very same people behind me that I had chatted with were now jealous/annoyed at the attention I was getting.

At 8am, now awake for over 28 hours straight, having flown from Ohio to Michigan to Pennsylvania and then a train from Pennsylvania to New Jersey to New York; it was game time! Production assistants begin assigning 7 or 8 people to each table that has one casting director or assistant director awaiting your arrival. We all know, or should know, television has one mission and one mission only, get ratings. Period. So, even though The Apprentice is about business and getting people with stellar business backgrounds, at the end of the day they want characters that will deliver rating. Of course, no bigger character than The Donald himself. It’s strategic that the casting tables are set up to have you and the 6 or 7 people you just shared your life story with for the last 5 or 6 hours be at the same table as you. They want to try to flip the script and get those soft and fluffy conversations you just had with those people, standing behind you or in front of you in line and spice them up with subjective questions in an effort to fuel disagreement. They want to see personalities.

The casting director has each persons resumé fanned out in front of him, with respect to the order in which we’re sitting around the table. In addition to our resumés he also has our applications which is very much geared more towards a reality show than a true job application, but there are some typical job application questions, like: “tell me a time when you thought outside of the box to get a sale” or “what has been your biggest accomplishment in your career so far and why” — things of that nature. The casting director goes around the table asking a few random questions, like one guy that was in real estate, “What’s the biggest house you ever sold, and how much was it?” To another girl, “Was Harvard Law School hard?” and so on. He asked me how I was able to broker the sale of a townhome in Columbus without being licensed. I explained that when I was renting a townhome the developer decided to make these townhomes for sale, AFTER I had already signed the contract to extend my lease. My neighbor, who was an ear nose and throat surgeon at OSU Medical Center (the hospital he worked at was only about 5 miles away) wanted to buy his townhouse and mine, knock down the common wall and have two properties converted into one large property. My roommate who majored in social work, didn’t have a clue how to negotiate, additionally a dollar amount that would have gotten him excited for us to move was far lower than the dollar amount that it would take to get me to move. We had all the leverage, my roommate had a hard time seeing that. We didn’t HAVE to move out, in fact, moving, whether it’s 500 feet or 500 miles is the same thing, a move is a move, it’s one big pain in the ass!

One day I came home from work and my roommate, Tim, with far too much excitement in his voice tells me, “Karen next door knocked on our door earlier today and I answered and she wants to pay us to move out so they can buy our place and we’d only have to move down the street to one of the vacant townhomes and she said she’ll give us $750!” and before I could even say anything Tim continued, “Oh crap, I forgot to ask if she meant $750 total or for each of us.” I said, “well, what if it’s total?” Tim said, “I’d move for $375!” I said, “remember this conversation, you’ll be thanking me later. There is no way we’re moving, not for $375 each, not for $750 each, no way!” I said, “I’ll make you a deal, if you agree not discuss with the neighbors or the leasing office anything related to this transaction moving forward and simply say, ‘You’ll have to ask Jason’ and we don’t end up getting at least $750 each, I’ll personally pay you $750 myself.” The townhouses were being listed for around $190,000, two master bedrooms, with walk-in closets and 2 private baths, then a half bath off the living room, equipped with a fireplace, two car attached garage and a balcony overlooking the Olentangy River. We were renting it for $1,150/month. Karen had asked me what I was willing to move for and I was quite candid with her, “I hate moving, not that anyone enjoys it, but it’s going to have to be a pretty good sum of money. Karen, I’m not sure why you’re doing all the negotiating, did the leasing office tell you that you’re the one that needs to do this? I say me, you and your husband sit down with the leasing office, who is taking the current tenants as first options to buy and work out a deal. They should be willing to come down in price, afterall you’re looking to buy TWO!” Knowing that they are only interested in buying two if we move out (because they don’t want to move), still leaves us with all the leverage. If I get too aggressive, they can simply say, “that’s too much, we’ll just wait until your lease is up and then buy” but they’ve already shown their cards, I know they REALLY want this thing now, not in 14 months from now. After further negotiations, I ended up getting us $7,000 plus moving expenses for the movers. Tim was happy he let me handle things. As I was explaining this to the casting director, I noticed he made some notes on my resumé.

Soon after the casting director completes these indivuals questions he then poses a single question for the group to answer, the question was: “Do you think dating should be allowed in the work place?” After about 90 seconds into the question being asked people are yelling over one another and name calling, I personally didn’t think it was such a loaded question. The casting director is getting what he wants, some voices being raised and “drama” as the group weighs in with their opinions.

Donald Trump makes his way over to our table while the arguing is going on, Trump kind of bends down to get ear level with the casting director who is sitting at the table and says “Anyone here I should know about?” Remember how I said the casting director had everyones resumés? Well, mine was the only one printed on deluxe parchment paper, so just by the shade of the paper, I could tell he picked mine out of the group and handed it to Trump. While all this is happening everyone at my table is still yelling and getting louder and louder, in an attempt to have Trump recognize them. I’m sitting back not saying a word, just observing. Trump says, “Jason, you’re awfully quiet, what do you think, do you think dating should be allowed in the work place?” I said, “I realize its a subjective question, I think in general it’s frowned upon more than it’s encouraged, but it depends on the company. For example, let’s take two magazine, Forbes and Playboy. Steve Forbes could not date his employees or contractors, yet, Hugh Hefner has built an empire doing exactly that, so it truly depends on the organization and the people.” Trump gave a small smirk and said to the group at the table who were now quiet as they listened to my response, “you know, he was the first one that arrived at like midnight, and was on the radio with me this morning, he’s young, but he’s a fire pistol, you guys really need to watch out for him, that I can tell you.” I gave a humble smile and thanked him for the compliment, but inside I was thinking, “holy shit, this couldn’t go any better, where do I sign, this is it!”

After that, the casting director dismissed the group and said, “If you don’t hear back from us by midnight that means you are not moving on.” We all left the table and yet again I was pulled in several directions, all simply because I was the first to arrive. I did an interview with CNN and half-dozen other publications. I left Trump Tower, and wanted to explore the city but I simply didn’t have the energy. I had been up for over 30 hours straight and still had to get on the train and head back to Philly.

I get to Pete’s place and he asks me how it went, I tell him, “I literally could not have planned it any better if I tried.” I was so afraid of falling asleep and missing the call, I asked if Pete would watch my phone while I take a nap. I napped from about 5pm-10pm then went to the bar with Pete. Midnight came and went, no call. NO CALL??? WHAT??? AFTER ALL THAT???

I get back to Pete’s place around 1am, and what did I do? I booked a flight to Chicago for the last city on The Apprentice Casting Tour. I went and I did not make it.

Despite several attempts I’m left with an entertaining story that has actually helped me in interviews and even client dinners. Some people pay for material things, some people pay for experiences, this was definitely an experience.

Who would have thought 10 years later Trump would be on the other side of the table interviewing for a job he wants.

Jason Von Sick lives in Orange County, California and did not write this with a political agenda, but just a great time to revisit a fun story.

Contact: jason@vonsick.com