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What It's Like To Work For A Billionaire

During my 20+ year career in financial services, I had the fortunate opportunity to work for several well-known billionaires.  

A calculator sits in front of a printout with numbers on it
Crunching Numbers on Wall Street

What is it like to work for a billionaire?

Billionaires tend to be enigmatic, yet full of conviction. They exhibit genius but are normally misunderstood. In the eyes of the public, they are either loved or hated.

Despite these dichotomies, billionaires also happen to have keen eyes for human talent - an important lesson I learned very early on in my career.

In fact, when I worked for my first billionaire boss, my promising work journey had barely begun.

After a grueling summer internship in Investment Banking on Wall Street at J.P. Morgan - a fascinating story which you can read all about here - I had secured a full-time offer to return back to "Mother Morgan" after my final year at university, which I immediately accepted.

As a result, I could strut around campus my entire senior year knowing that my illustrious career was all but assured, and I savored every moment of my perceived security.  

This contented feeling was a stark contrast to the year prior when my visceral feelings of self-doubt eventually led me to meet my first billionaire socially (click on my eye-opening narrative about that experience here).


I was all set to begin my job as an Investment Banking Analyst in September 2000, and I graduated the University of Texas at Austin summa cum laude in early May 2000, leaving me plenty of free time on my hands before joining the work world.  

Starting at the end of May, I spent a month and half in Europe touring the continent. 

A picture of Austin Rosenthal in a fancy suit in front of a London double decker bus
Me in London circa July 2000

My European graduation trip would traverse 14 countries in 52 days and consist of three different itineraries. First up was a month with The Flying Longhorns, a group of recent UT graduates circumnavigating Europe from London to Athens. 

The second portion I spent in the French Riviera and Amsterdam, and the final leg was with my family on a luxury cruise through Scandinavia and Russia, ending up in London.   

Needless to say, I spent all my meager savings on the trip, and when I arrived in New York at the end of July, facing rent and six weeks of potential unemployment before my start date at JPMorgan, I began to seriously FREAK OUT.

I had just moved to one of the most expensive cities in the world, and I had ZERO income.

This was not the career start I had envisioned.   


After two days of eating nothing but ramen, I decided to reach out to a high-end staffing agency for some part-time work in my few idle weeks before the real beginning of my career, which I awaited with great anticipation.  


Within days of visiting the midtown Manhattan Randstad staffing office, I was requested for a one-day trial at a Park Avenue hedge fund run by a famous billionaire sports owner’s daughter.  

I put on one of the suits I had recently purchased (see link to my story about the Investment Banker Wardrobe) and walked from my apartment at 55th and Broadway to the Rolex building at 5th Avenue and 53rd Street, where the hedge fund was located.  

After checking with security downstairs, the elevators took me up to a plush office with sweeping views up 5th Avenue towards Central Park.

Upon arrival, I met with the head of the firm - the billionaire’s daughter, and learned that she was in charge of investing the family fortune.

Surprisingly, she was less than ten years older than me; however, her high intellect was obvious, and her Harvard business school degree loomed behind her jet black hair as she spoke to me across her desk, which was adorned with multiple Bloomberg terminal screens.

Stock and bond figures appear on a computer screen
Screens of Wall Street Traders

As CNBC ran on the TV in the background, the billionaire’s daughter explained the firm’s investment strategy to me - a buy-and-hold fundamental analysis approach investing in high yield bonds.  


In the summer of 2000, the high yield bond market was in its adolescence.

What are high yield bonds?

According to Investopedia,

High-yield bonds (also called junk bonds) are bonds that pay higher interest rates because they have lower credit ratings than investment-grade bonds. High-yield bonds are more likely to default, so they pay a higher yield than investment-grade bonds to compensate investors.

My boss, the billionaire’s daughter, had convinced her father that there were significant investment opportunities in the evolving high yield bond market.

Specifically, she believed that many of the securities in that market were mispriced, and that she could identify which bonds were undervalued.  

a technical line chat with stock price data
Wall Street Analytics

As a result, in my role as an Analyst, I needed to pore through company annual reports and calculate a variety of leverage ratios in an Excel template that she used to uncover which bonds she thought would go up in value.

I also was to permanently man the fax machine - yes, back then in the summer of 2000, we received high yield bond prices and yields from the dealers via a daily facsimile.  

To execute any purchase or sale order, you would actually have to call the broker and make the trade - very little was executed online, which is substantially different than today.  


Over the course of the rest of my first day as a temp worker, I completed a few of the templates, and at the end of my 9-5, she reviewed my work.

view of a page with pie charts and figures with a female hand and pen checking the work
Financial Analysis

I spent half an hour in her office as she meticulously spot-checked my numbers, her expensively-manicured eyebrows raised from time to time.

I had no idea how I had done.  

At the end of her assessment, she put down the papers and pen and looked straight at me.

“Very good,” was all she said.

As I walked back to my apartment, I received a call from the staffing firm.  Apparently, I had impressed her enough that I was extended indefinitely (until my start date at JPMorgan).


I was happy and settling into New York City life.  

A view looking up at the clouds past urban skyscrapers
New York Skyscrapers

I was barely 21 years old, and I could actually afford more than fast food.  

Meanwhile, over the course of August 2000, I became an essential part of the hedge fund firm, assisting with the investment analysis of over $200mm of high yield securities the billionaire’s daughter eventually purchased.  

While I felt respected, she never really warmed up to me, which was fine.  I did my work during the workday and then got to experience the city in the evenings, walking around Central Park and checking out the Museum of Modern Art and the Metropolitan Museum of Art.  

As a result, I was surprised that on my final day before starting at JPMorgan, the billionaire’s daughter called me into her office.   

She smiled at me, and then I heard a voice coming from the air.  

It was the famous billionaire father on the speaker phone, and he was offering me a full-time job!

An office phone circa the 2000s
Office Phone

Here is how the conversation went:  

“Austin,” he said, “Do you know who I am?”

“Yes sir, very nice to speak to you, sir.”

“My daughter thinks you are an exceptional worker.  How about you forget about JPMorgan investment banking and come work for me instead?”

I stood there speechless as the thoughts were racing through my head faster than the Formula 1 race cars down the straightaway at Circuit of the Americas in Austin, Texas.

I can't believe my good fortune! But now I have to make a life-changing choice, and I am terrible at that!

I need to think about this logically in terms of pros and cons and not let my emotions cloud my judgment.

Pros for working for the billionaire - he is incredibly well known and owner of several successful sports teams, and he wants me to come work for him.  That's insane, maybe I can just skip a step in my career and go straight to the buy side of investing.  

Cons - this job offer was not part of the plan.  I really enjoyed my time at JPMorgan last summer and already committed to them. What happens if things don't work out with the billionaire, and I gave up my opportunity on what was really meant to be - the job that I had set my heart on for the past year?

What should I do?  

In that terrifying yet exhilarating moment where I was put on the spot, I made a decision that had major ramifications on my future.

Starting my career at JPMorgan had been the initial plan, and I needed to stick with the plan.

After listening to his sales pitch, I politely declined, thanked him effusively and wished he and his daughter success in the future.

The following week I began my career in earnest on Wall Street in JPMorgan’s Investment Banking Division.

My career journey was just beginning.  


These days I look back at my career and wonder.  

What would have happened if I had accepted the billionaire’s job offer then and there?

The answer to that question is impossible to know; although, I am still incredulous that I actually declined a billionaire's plea for me to join him.   

What I can say is I have NO REGRETS.

In the end, I took the traditional path early in my career (Wall Street investment banking) and then the non-traditional path at the end of my career (quitting my finance job and becoming a digital media entrepreneur), and that is exactly how it was meant to be.

I hope you enjoyed this original story.  If you are interested in reading more of my tales from Wall Street, check out the Passages from My Book section on my Social Musings by Austin website. 

P.S. - The billionaire’s daughter is now also a billionaire.  So it was like I worked for two billionaires in that one family.  🙂

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Fascinating Austin, best of all is the "no regrets" aspect.

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