Move to NYC? 8.13.26

I was quite anxious as my plane touched down in Richmond after a short flight from New York.  I had just finished an intense interview schedule with First Boston, one of the leading investment banking firms on Wall Street. I had decided to make the trip to New York because First Boston was recruiting me to join its Investment Banking Group. It is not every day that one of the most respected and profitable investment banking firms on Wall Street comes knocking at your door. It is usually the other way around – with you knocking at their door.

When I arrived in New York the previous afternoon, First Boston had arranged for a limousine to pick me up at LaGuardia. I was then whisked away to the Plaza Hotel, where I would be staying for the night.  For dinner, I was meeting the Head of the Group and a few senior bankers at “The Sign of the Dove”, an upscale restaurant located on Third Avenue.  I had eaten at that same restaurant eighteen months earlier for a Closing Dinner that my current employer had hosted.  It was very common for investment banking firms to host Closing Dinners to celebrate the completion of large and profitable transactions. The particular transaction that we celebrated eighteen months ago at “The Dove” was a $55 million tax-exempt bond transaction for The Forest at Duke, a brand-new start-up non-profit senior living community located in Durham, N.C. That deal had become a very noteworthy transaction in the industry and had turned a lot of heads.  Not lost on me was that it was because of that deal that I ended up back at The Dove having dinner with First Boston Bankers.

Although I was happy at my current firm, Wheat, First Securities, Inc., a well-respected regional firm in Richmond, Virginia, I decided it could not hurt to talk to First Boston.  I had only been at Wheat for three years when First Boston came calling.  And I had been there for only a year when I began working on The Forest at Duke transaction. However, I had learned the business quickly and I had advanced accordingly.  My first day at Wheat was my birthday, June 6, 1989. I was hired as an Associate.  In less than a year I was promoted to Senior Associate.  By the time The Forst at Duke deal closed, I had been promoted to Assistant Vice President.  And a year after that to Vice President.  So, when First Boston came knocking on my door, I had been promoted to Vice President. However, I was killing myself, working sometimes 80 hours a week.  So, one of the reasons I decided to talk to First Boston was to explore whether it might be better to work 80 hours a week in Richmond or in New York City.

So, why did First Boston want to hire me?  When I had graduated from the UNC School of Business with an MBA five years earlier, I would have jumped at an opportunity to work for a firm like First Boston.  However, the only regional investment banking firms were willing to interview me – Wheat, First Securities in Richmond and Interstate Johnson Lane in Charlotte.  And I got no offers from them.  I did end up at Wheat First Securities two years after I graduated from Business School, but that is a story for another day. The only offers I did receive after graduation were consulting jobs from two regional accounting firms– one in Richmond and one in Greensboro.  I became depressed.

I think having no business experience prior to business school hurt me as a candidate. Prior to business school, I was a systems engineer at NASA.  I thought that getting a degree from one of the top business schools in the country would land me a job with a prestigious investment Banking or consulting firm, or at a minimum, a fortune 500 company.  But the best I could do was land a job as an entry level general management business consultant with a regional accounting firm.  MBA in hand, I chose the job in Richmond to be closer to family. 

So, what had changed from five years ago to cause First Boston to come knocking at my door? Two things occurred. The first is that First Boston was experiencing huge “deal flow”. Usually, investment banking firms train their own bankers, especially their “Deal Bankers”.  Sometimes called “Day-to-Day” bankers, these Deal Bankers are the people who get the deals done.  And because the senior bankers at various firms are very particular on how they want their deals structured and how “their clients” are served, you can understand why firms want to train their own bankers.  But First Boston had a problem. It did not have enough Day-to-Day bankers to handle the deal flow.  There were not enough bankers to process the numerous tax-exempt bond transactions that were coming through their door. So, they needed a “trained” Day-to-Day banker that could hit the ground running.

I had a very good friend once, Rusty Quynn, who was known for coming up with catchy phrases that creatively and succinctly captured the essence of a situation or idea. He used the following phrase to summarize the hierarchy of the investment banking world. He said investment banking shops had “Finders, Minders and Grinders.” The Finders were the senior bankers – the rainmakers who made most of the money.  The Minders were the Day-to-Day bankers who worked hard to get deals done and got paid relatively well.  The poor Grinders did a lot of number crunching, worked endlessly on “Pitch Books” and had to do most of the administrative work associated with processing a deal. They got paid well given their age and rank, but it was a brutal schedule with bosses who treated most analysts like paid slaves.  Even though I had become a Minder, I still had to do a lot of the Grinder work because Wheat First Securities was a small shop.  I found out that if I joined First Boston, I would no longer have to do the Grinder work.  First Boston had a sweat shop of analysts who did most of that.  I would be a full-time Minder. THAT was very appealing.

So, a unique situation presented an opportunity for a Day-to-Day banker like me who was already trained.  But why me?  There were several bankers in the industry like me, some who were already in New York.  What made me unique?  Well, I had become a very good Day-to-Day banker. I could process deals and did so very well. In fact, because I reported to no less than three senior bankers, I was processing as many as six or seven deals at once. 

But how would First Boston find me? Sometimes investment banking syndicates are formed where more several investment banking firms work together to underwrite a deal. In fact, this arrangement was very common.  However, I had never worked on a deal with First Boston.  Their deals were much larger than ours.  They were in another league altogether.  It would be like the New York Yankees deciding to go after a AA player from another organization.  How would they even know about such a player?

I found out later that First Boston had been given my name by two people who I had worked with on several deals, including the aforementioned Forest at Duke deal.  The first of these was Peter Michelle, a well-respected bond lawyer for Brown and Wood, one of the most prestigious Securities Law Firms in New York City.  A Duke Law graduate, he had a commanding presence. You could feel the gravitas when he walked into a room. To be honest, when I stared my career as an investment banker and attended my first few document meetings where Peter was in attendance, I was totally intimidated by him.

The second person who gave them my name was Chris Taylor, who worked for the North Carolina Medical Care Commission. In North Carolina, every tax-exempt healthcare bond transaction, no matter the size, had to get approved by the “Commission.” And the staff of the Commission was very tough on investment bankers. They saw their role as advocates for the borrowers to make sure that the shrewd investment bankers did not take advantage of the 501© 3 healthcare organizations in their state. Chris not only paid attention to detail, but he also had strong opinions on the structure of a deal and how the bonds would be sold to investors.  Chris was another person who intimidated the hell out of me.  With a stern face that seemed frozen, he rarely smiled.

When we began the Forest at Duke deal, my boss and mentor, Cam Hoggan was running point on the deal. By the time we got the deal closed, I was running point on some of the document meetings.  Cam was very good at delegating. Evidently my “deal management’ skills and attention to detail must have impressed both Peter Michelle and Chris Taylor. When I received the first phone call from the bankers at First Boston informing me that they were interested in talking to me about joining their firm, I asked the obvious question, “How do you hear about me?”  Without hesitation they said that both Peter Michelle and Chris Taylor had recommended me. I was taken aback.  I really respected those two gentlemen.  Later, during my investment banking career, both would become dear friends and colleagues. Elizabeth and I would visit Chris and his wife in North Carolina. We would schedule our NYC trips so that we would be in New York at the same time.  Chris loved attending plays in NYC.  So, we would sometimes attend plays together.  I still smile when I think of all the deals we worked on together. As he got older, he relaxed more and smiled more.

So, that is how I ended up back at The Dove in New York with First Boston Bankers.  I must have somehow made a decent showing over dinner because the next morning, when I met the Big Boss, the Head of the Municipal Investment Banking Group, he mentioned that the folks that I had dinner with the night before had good things to say about me.  As I went through that day’s activities including numerous interviews and lunch with the other Day-to-Day Bankers, I kept asking myself why am I here? And I kept telling myself that this is a “once in a lifetime” opportunity.  I loved investment banking and I loved working with non-profit organizations.  I also loved working on very high performing teams.  And this opportunity would allow me to work with the best of the best doing what I loved to do.

Before I had left for New York, I had sat down with Elizabeth, and we talked about the opportunity to work for First Boston in New York City.  Davis, our oldest son, was three years old at the time. Jack had just turned one, and Elizabeth was seven months pregnant with Carter. So, we were a growing family.  What would it be like to live in metro NYC with three small children?  One thing Elizabeth made clear.  There was no way we would live in New Jersey, or in Connecticut, or on Long Island with a long commute. Because of the hours I would be working, she wanted me to be close so that I could get home and then go back to work if I had to. So, if I was going to work in Manhattan, that is where we would live.

And she said she was willing to sacrifice space and live in a small apartment for a while. However, she was not willing to live in NYC forever.  In fact, she said she would prefer three or four years – five max. And then she wanted to move back to the Southeast, saying that even Charlotte would be ok. So, my beautiful and understanding wife was willing to leave our community in Richmond to allow me to pursue what appeared to be a huge career opportunity. When I originally brought the idea to her, I thought she would say no.  Instead, she was supportive.  And so, after I landed in Richmond and got into my car to begin the drive home, my anxiety only increased? What if First Boston offers me the job? How do I transition to New York? Can I really hold my own with the talent at First Boston? Can I leave Wheat? Can I leave Richmond? What should I do?

As I was driving home, I figured out a way to relieve my anxiety. I decided I would not worry about deciding on whether to accept a job on Wall Street until it was offered.  Maybe I was being a little cocky.  In fact, during the interviews, I made it clear that if I came to work for First Boston, I strongly preferred to work in NYC for only 3-5 years and then wanted to move back to the Southeast, preferably Richmond, but would consider Charlotte. I thought that request would put a big splash of cold water on their enthusiasm of me as a job candidate.  Who is this guy making demands about location when he should be licking our shoes for this opportunity.  So, I thought that maybe they would decide I was not the right candidate.

When I got home around 7 p.m. that evening, Elizabeth asked how it had gone.  I relayed the day’s events including my request to move back to the Southeast. And then the phone rang.  It was David, the head of the Healthcare Group at First Boston.  He said that everyone loved me.  The firm wanted to fly my wife and me to New York as soon as possible to scout out homes in Connecticut, New Jersey and Long Island.  I guess they figured that anyone with three kids would want to live in the suburbs of NYC. 

I had not told First Boston that I would have to live in Manhattan.  When I asked him about my desire/requirement to move back to the Southeast, he said, “Yes, we did discuss that.  And in fact, we love the idea.  We had discussed opening an office in the Southeast to serve our clients there. And we believe that you, after working in the home office for three or four years, would be the perfect person to open a Southeast office.” He then explained that they were also in the process of putting a formal offer together.  It would obviously include a signing bonus and a guaranteed minimum bonus for the first two years. I was stunned.

I realized I had been playing a game of make believe up until that point – in essence what was happening was not really happening. The idea of working for one of the top firms on Wall Street, living in Manhattan, and raising a family in the city was so foreign to me that I could not really wrap my head around it.  I do not remember what I said when I hung up the phone, but I must have mumbled something about getting back to him.  I relayed the conversation to Elizabeth and she said, “Well, you have a tough decision to make. As I said, I am willing to move to support you. But only you know what this really means for your career.  So, you are going to have to make it.”  I did not sleep well.

There are times in our lives when we are faced with decisions that we know will totally change the trajectory of our lives and the lives of those we love. I knew that if I continued to pursue the opportunity with First Boston, not only would my life change, but so would Elizabeth’s and our children’s.  Let’s be real here.  My ego wanted to pursue this opportunity.  If this was going to be about me, I would go to NYC and I would kick ass. I would become the best investment banker, and people would know that I was the best because I would be the best of the best. My talents would no longer be hidden at a small regional firm.  However, if that was why I wanted the job, was that the right reason? There would be a lot of sacrifice – not just from me, but for my family, especially my wife.  You do not get to be the best of the best on intelligence and talent alone. You also outwork everyone else.

And when that realization, like a friend telling you something that you know is true, but you do not want to hear it, became crystal clear and apparent, I knew that I would not pursue the opportunity with First Boston. If I wanted a good marriage and an actual relationship with my children, taking the First Boston job would be the last thing I should do.  In addition, we lived on a wonderful street, and we were beginning to make close friends in our community. We had just built our new house. I did not know it at the time, but that street and neighborhood would become important influences on our family.  We would develop close life-long friendships with many of our neighbors, as would our children. And we would join a church that would also become a huge influence on our family.  In summary, we would become a part of a community that most people only dream of.  I did not know these things in 1992 as I lay awake contemplating my decision.

Several times I thought, “Maybe I could manage it and have it all.”  Here is the sad truth – if I pulled that off, I would be the exception. That is the lie we and society tell ourselves – that we can have it all.  But we cannot. Life is about tradeoffs and always will be.  Going to college, getting married, having children, where you live, and… career choices.  All come with tradeoffs.  But the realization that made me confident with my decision was the following – I already had my dream job living in a dream community.  If all I was going to do was live and work in NYC so that I could move back to the Southeast, why leave the Southeast to begin with?

The next day, without fanfare and without drama, I called First Boston back. I told David, the Group Head, that First Boston would not need to fly my wife and me to New York because I was going to stay where I was.  I was happy at Wheat First Securities, and the firm had treated me well.  I think David was as stunned by my statement as I had been the night before from his.  He was quiet. I continued. “I am so honored that you and your firm have presented this opportunity. I am not making this decision lightly.  I know it may be a once in lifetime opportunity.  You and your team have been so gracious, and so generous with your time.  And that is why I am stopping the process now.  It would not be fair to you and First Boston if I let you fly me to NYC, to be wined and dined, and all along, knowing that I probably will not take the job.”  I told him that I realize they needed someone quickly, and if I was not going to take the job, they need to pursue someone who will take the job. I could tell he was processing.  “Are you sure?”, he asked. “I am sure.”, I said.  

I have not told many people this story. When I recently relayed this story to my brother Keith, he said he had never heard it. I guess I had just moved on after it happened. When I did occasionally tell this story someone would inevitably ask if I ever regretted turning down opportunity.  My response is always, and remains, “Not ever.”

Later in my career, I would have another opportunity to work for a Wall Street Firm, which I would take advantage of.  However, that is also a story for another day.