Interview Series

Insights from an accomplished attorney

Matt Viera
December 02, 2022

Image by David Mark

Good morning and happy Friday!

I hope you had a productive week.

I started this newsletter with a focus on personal finance and building wealth.

However, I had the idea of creating an interview series.

I have many friends who are incredibly successful in their respective careers.

Each of these individuals can provide valuable insight into life and career success.

I emailed each individual a series of questions for them to answer.

My goal is to find key takeaways from their answers that I can apply to my life and career.

My hope is that their answers can do the same for you.

This week, I'd like to introduce my friend, attorney extraordinaire, Max McCann.

Max McCann

I have known Max for ten years. Max started his career as an attorney in New York City.

Max has been practicing law for 14 years and currently lives in St. Petersburg, Florida.

While I have never worked with Max, I can safely say he is a highly knowledgeable attorney who is fiercely disciplined in his career.

I can write a book from what I learned from Max over the years.

I am also fortunate to say Max gave me one of the greatest compliments.

One evening, in a Brooklyn bar, Max said to our friends, "Matt had the right idea when he decided to stop practicing law."

There's not a day that goes by that I don't think of that statement.

Here is my interview with Max:

What motivated you to pursue a career in law? Where did you go to law school, and how long have you been practicing?

I went to law school to make the world a better place (idealist, I know). I went to Brooklyn Law School and have been practicing for 14 years.

What are some of the highlights and accomplishments of your career?

I'm proud of having conducted six trials in federal district court, even though I hated every second of it. I'm also proud of having successfully argued a case before the N.Y. Court of Appeals [New York State's highest court and court of last resort in most cases].

How has failure, or apparent failure, set you up for later success?

The failures that I've had as a lawyer have taught me that being right on the law will only get you so far. At the end of the day, judges and juries are going to do what they want. Realizing this has made me more creative in my approach to litigation because now I know that you can't just beat the judge over the head with the law. After several tough oral arguments, I've also realized that there's a difference between winning an argument and being persuasive. Even though I know this, I still struggle to internalize this lesson.

What are three life lessons you have learned so far in your career?

My career has taught me that I don't really like being in the spotlight and that this is perfectly okay. Society often sends the message that, to be successful, you need to perform publicly, and the larger the crowd, the better. But you can also be successful by simply producing great work by yourself. It took me 40 years on this planet to accept that I would rather work quietly or in a small group to solve difficult problems than be the center of the attention of a large crowd.

My career also taught me that you can be perfectly happy with a modest salary and a good work/life balance. I have a quote on my whiteboard that says, "the easiest way to gain happiness is to want the things you already have." Working for the government, I've sometimes had to make what felt at the time like sacrifices, but now I know that consumerism is a trap. Put differently, if you're looking for happiness at the bottom of a shopping bag, you're setting yourself up for a lifetime of disappointment, no matter how large your salary is.

Finally, my work has taught me that I prefer collaboration over confrontation. I still do litigation, so I deal with confrontation, but I look for as many opportunities to work collaboratively as possible these days.

What advice would you give someone interested in pursuing a career as an attorney?

My advice for prospective law students is: don't trust the employment and salary statistics published by law schools and be prepared for the possibility that you might graduate with $200K in loans while making around $50K per year. Also, talk to as many lawyers as you can before making the decision as there is so much variation in legal careers and experiences.

What advice would you give your 20-year-old self?

I would tell my younger self to recognize that time is your most precious commodity, so guard it jealously.

A few years ago, you decided to move from NYC to Florida—what prompted you to make this move?

We moved to Florida to be closer to my wife's family and for general quality-of-life reasons. Here in St. Petersburg, we still live in a fairly urban environment, but we have been able to buy a home here, which probably would not have happened in NYC, and we have more space for my daughter to run around.

What obsessions do you explore on the evenings or on weekends?

Working on my house and trying to be a good dad and husband. I recently realized that being a lawyer, I really missed working with my hands. Building something that you can see and touch can provide a lot of satisfaction in ways that mental work cannot. I also think about sustainable transportation a lot these days.

If you could have a billboard anywhere in the U.S., where would it be, and what would it say?

I've thought about this before. I would put the billboard somewhere like Times Square so that the greatest number of people could see it, and it would say, "Cars ruin cities" or maybe a more R-rated version of that message.

My key takeaways:

“There's a difference between winning an argument and being persuasive.”
“Collaboration over confrontation.”
“Consumerism is a trap...if you're looking for happiness at the bottom of a shopping bag, you're setting yourself up for a lifetime of disappointment, no matter how large your salary is."