Alexander Apostolopoulos has worked for multiple American multinational law firms in New York City. He excels in areas of transactional tax law, with a focus on optimizing tax structures for business enterprises in both the public and private sectors. He has extensive experience with spin-offs, initial public offerings, private and growth equity transactions, and continuation fund transactions, among other corporate matters. Alexander Apostolopoulos has represented clients during numerous large transactions, including growth equity transactions for a technology investment firm with $21 billion in capital commitments. He began his career as a tax associate at Sullivan & Cromwell in 2011. During his eight years with the firm, he represented major corporations such as AIG and Wells Fargo. He also represented Kodak during the company’s bankruptcy and restructuring.
Alex Apostolopoulos studied ancient Greek and Latin at Yale College, graduating summa cum laude in the top 1 percent of his class. He received his juris doctor from Harvard Law School. He studied corporate and securities law policy, bankruptcy, financial regulation, and tax law, graduating magna cum laude.
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What is your typical day, and how do you make it productive?
I stay on top of current news and events, especially in turbulent times like these, by reading various news outlets. I also stay on top of developments in my professional field, transactional tax, by reviewing articles, proposed and final regulations issued by the Department of the Treasury, and legislation proposals. I balance my professional activities through almost daily exercise, which helps me stay physically in shape, but also provides a “time out” from thinking.
How do you bring ideas to life?
I am an intuitive thinker, so ideas can come to me from various sources and sometimes seemingly at random. At the same time, I am a very analytical person, so when I have an idea, I question it at first and mull it over from various perspectives, never jumping to conclusions that the idea itself is valid or has merit. I think it is important to critique one’s own ideas and be self-critical in all respects. To bring an idea to life then requires a detailed plan before plunging into action, but once I have assembled everything in my mind, I tend to act decisively.
What’s one trend that excites you?
I am excited about artificial intelligence, although I am also a bit wary of where it will take us. I grew up at a time (the early 90’s) when the internet was in much earlier stages of development – it felt a little bit like the Wild West. (Of course, that can be said of the internet and social media today, but back then, it had a feeling of experimentation and newness to it.) The current developments in AI feel similar in that a new frontier is being explored, so I am excited to see where we will go next.
What is one habit that helps you be productive?
Exercise. While I was always practicing sports growing up, I started neglecting physical exercise when I began working professionally. This was also the time I first moved to New York City, so I was excited to spend time exploring the city whenever I was not preoccupied with my busy job. I am very glad that, in 2015, I committed to working with a personal trainer to get myself back into shape. Thankfully, my trainer was excellent – her style and personality were a perfect fit for me. Since then, I have been going to the gym on an almost daily basis. I almost always look forward to it and always feel great afterwards. On days when I do not look forward to it, I force myself to go and then realize afterwards that it was worth the effort.
What advice would you give your younger self?
To be a little more easy-going on myself. I have the tendency to be a perfectionist, and everything needs to be “just right.” Of course, making things perfect can be very satisfying; however, it can also result in frustration when things don’t go as well as planned or roadblocks are encountered along the way. Achieving the last 0.5 percent of a desired goal can often require outsized energy that may ultimately not be worth it when looked at post-hoc.
What is the one thing you repeatedly do and recommend everyone else do?
Keep your mind and body active. I have a large array of intellectual interests, and I can easily spend a few hours on a weekend deep-diving into such diverse topics as current cases before the Supreme Court, the history of certain historical architectural trends in New York City and their landmarking designation, or reviews by various commentators on newly released music by contemporary artists that I admire, such as Aphex Twin or Burial. And, as I mentioned before, exercise is key to stay in shape and feel good.
When you feel overwhelmed or unfocused, what do you do?
I remind myself that I have previously encountered problems and have previously been overwhelmed or unfocused, but that I have been able to overcome those instances. Also, taking a break and stepping back to assess the reason for the feeling can help overcome it. In addition, depending on the situation, calling a trusted friend or colleague to discuss the situation with them and seek their insight.
What is one strategy that has helped you grow your business or advance in your career?
Being excellent in my field. I am a transactional tax lawyer, so I work on complex business transactions and advise on the tax structuring thereof and participate in the related contractual documentation. Being known for my commitment to excellence and reliability has helped me advance my career.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Any practitioner in my field will tell you that the US tax system is incredibly complex and riddled with traps for the unwary. And they will also tell you that it is inevitable, although regrettable, that mistakes can happen. In a rare instance when I uncovered a situation where a slightly different approach to the one I had originally proposed would benefit the client, I immediately brought it to the attention of the legal team advising the client, and we were thankfully able to fix it. It is important to be aware that we are not perfect. But living up to mistakes is important, and it is always very helpful to run ideas past trusted colleagues to get their take on them.
What is one piece of software that helps you be productive? How do you use it?
There are various redlining tools that are helpful in my practice. A PDF redline will show all the changes made between the versions compared and will aid (and make more efficient) the review of the latest document and required edits thereto.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
My favorite book is called The Man Without Qualities by Robert Musil. The novel is a “story of ideas,” which takes place in the time of the Austro-Hungarian monarchy’s last days, and the plot often veers into allegorical digressions on a wide range of existential themes concerning humanity and feelings. It has a particular concern with the values of truth and opinion and how society organizes ideas about life and society.
What’s a movie or series you recently enjoyed and why?
I enjoyed the series Succession. I would say that I would find it hard to believe that it was close to a realistic depiction, but all the actors did an extraordinary job portraying their character. I also thought that the quick-witted dialogue was entertaining.
Key learnings
- Staying mentally and physically in shape by pursuing intellectual interests and exercising consistently are key to feeling good and being balanced.
- When facing difficulties or failures, stepping back and/or seeking help from trusted friends and colleagues often can provide a path to a solution.
- While commitment to excellence is a key element to success in academics and in a legal career, there are levels of perfectionism that can be disproportionate to the goal that you are intending to achieve.