Be willing to move. Family is important.  Don’t burn bridges.

A conversation with attorney Jerry Grossman reflecting on his career in the legal field.

This week, we’re visiting the coastal San Diego office to have a conversation with Jerome “Jerry” Grossman reflecting on his 30+ year career in the legal field practicing commercial real estate. Jerry is an Of Counsel attorney in our San Diego office who has a wealth of experience in real estate finance law and has represented clients in a broad range of general commercial and real estate finance matters for more than 30 years.

He focuses his practice on Uniform Commercial Code secured transactions, real estate secured transactions, and other financing transactions (including securitized financings) – from the initiation stage through workouts and restructurings – and third-party legal opinions.

Hi Jerry! Great seeing you today. Everyone has been talking about the blockbusters of the Summer, Barbie and Oppenheimer. Have you seen either of them?

I took my 22-year-old grandchild to see “Barbie.”  It was surprisingly deep and had a good sense of humor.  It was a lot of fun.  I’ve read that Greta Gerwig, the director, had eaten many Sabbath (Friday night) dinners at the home of a Jewish friend as a child, and that her friend’s father had always said the traditional blessing over the children, including Greta.  Per Greta, “I remember feeling so safe in that and feeling so, like, enough.  I want people to feel like I did at Shabbat dinner. I want them to get blessed.”  It worked for me.


How did you end up practicing commercial real estate law? Was there one moment where you knew this is what you wanted to be your primary practice?

I started with Heller, Ehrman, White, & McAuliffe, in San Francisco, in September 1982.  Sometime in the first half of 1983, I worked on my first financing transaction:  representing Wells Fargo Bank in the secured financing of oil drilling rigs that would be leased to a drilling company.  I enjoyed that project, and was able to handle a second, nearly identical, financing with only a little supervision.

 Then, in January 1984, Heller moved my entire family to Hong Kong, where I was the junior corporate associate for two years.  There, I was able to work on a number of loan transactions, including intra-company loans made by parent companies to subsidiaries to finance U.S. subsidiaries as well as commercial loans—including a syndicated loan to the Hong Kong partner in a Chinese joint venture to finance the installation of an aluminum can manufacturing plant at a brewery in Zhaoqing, China.  I found working to ensure that the several documents involved in a complex financing transaction meshed well together an intellectually stimulating task, and one that I was temperamentally well-suited to.  When I got back from Hong Kong, I actively sought out more of it, and Heller Ehrman was happy to accommodate me.

I’ve also been fortunate in that, by and large, I’ve not been stuck working on cookie-cutter deals, and have been able to familiarize myself with a broad range of different financing transactions.

What made you interested in pursuing a career in law after studying Anthropology at UC San Diego in under grad?

A 790 in English on my GRE, having a child the year I graduated from UCSD, obtaining a vocational teaching credential and teaching high school kids and adults how to be grocery clerks for the San Diego County ROP (Regional Occupational Program.)

I went to UCSD.  I spent my junior year in Spain, studying Spanish at the University of Madrid–but UCSD offered no degree in the Spanish language, so I returned from Spain with a ton of Spanish credits but no upper-level credits towards a degree in any available major.  I looked at Linguistics and Anthropology, and chose Anthropology as a degree I would most likely be able to complete in a single academic year.  Shortly after starting my senior year, however, I met and married my wife, Mary.  It took me two years to graduate, and by then Mary was pregnant with our first child.  Moreover, I’d realized that Anthropology was not my “forever” field. 

I started taking classes at SDSU to get into their elementary teaching credential program while working full time as a cashier at FedMart.  A friend who had been teaching retail cashiering for the ROP talked me into applying to teach there, so I took the necessary classes and earned a temporary vocational teaching credential.  I learned, however, from parenting my own child, that I might not have the patience to teach little kids, and I learned from my vocational teaching that adults were far more motivated students than were high school kids—so that if I ever did teach, I wanted to teach adults.  Mary became pregnant with our second child.  I decided that, if I didn’t want to spend my life as a grocery cashier, I needed to go back to school for a degree that would allow me to earn enough to support a family immediately following graduation.  I’d gotten that 790 on my GRE, and I had always enjoyed reading and language. I took the LSAT, scored an 800, and went to Berkeley.

With 30+ years of legal experience under your belt you must have a strong understanding of how law practice – a very traditional career field – works. What do you foresee being the biggest change in legal practice in the near future?

I think there are two:  the adoption and integration into our practices of AI-generated output, and the adoption of remote working. I think that, with a proper appreciation for both its strengths and its weaknesses, we can use AI to improve the quality of the service we provide to clients.

  I have mixed feelings about fully remote work—I perceive benefits to in-person interactions—even serendipitous ones—that I’m not convinced can be achieved over Teams or Zoom.  (For example, when I was at Dewey Ballantine in LA, we had a group of 5-6 folks, including real property dean Alan Wayte, who went out to lunch together on a weekly basis.)  But people are different in that regard.  As long a decent number of folks elect to spend time in the office, the hybrid model may let both those who value in-person interactions and those who function best remotely achieve professional and personal satisfaction in their practice of law.

What advice would you offer to someone who is just starting out their career in law now?

Try to find work you enjoy doing—it will help avoid burnout–but be flexible. Be willing to move. Family is important.  Don’t burn bridges.  (Over the course of my career, I’ve worked twice at two different firms.)  And, of course, anything worth doing is worth doing well. 

Are there any TV shows or movies that you’ve been binging lately? Or book that you just can’t put down?

I just binge-read N.K. Jemisin’s The Inheritance Trilogy, as well as her follow-on novella, The Kingdom of Gods.  I read the bulk of the third book in the Trilogy on our flight to Hawaii and the follow-on novella on the way back.

Before leaving, my daughter Hannah and I re-watched “Good Omens” in preparation for “Good Omens 2.” We watched the first episode last night.

 And last but not least, if you could only eat one meal for the rest of your life, what would it be and why?

Based solely on taste: chicken tikka tandoori—I fell in love with the dish in Hong Kong (where I worked for two years as a junior associate), especially as prepared at the Maharani Mess.   But I’m practical enough to say that, if I were really going to be limited to one meal, I’d want something that was nutritionally complete and that worked with my low-carb diet—so I’d also want salad with lots of veggies, avocado, Swiss cheese, and nuts (preferably pecans, walnuts, and pistachios).  And for dessert: Montezuma’s Absolute Black chocolate (100% cocoa).

Many thanks to Jerry for his profound insights!

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