Episode Highlights

Choosing Deals Over Fighting and Puzzles

Someone once told me lawyers basically do three things: some come to work every day to fight as litigators, some come in to solve puzzles in regulatory or tax practices, and some do transactional work. When I started out, I sampled all three and realized pretty quickly that I enjoyed the transactional side much more than the fighting or the pure puzzle-solving.

— Andy Sucoff

The Billion-Dollar Sears Tower Deal That Hooked Me

One of the first deals I worked on at Goodwin was the first single-asset, billion-dollar real estate transaction in the United States—an acquisition of what was then the Sears Tower in Chicago by a local Boston pension fund adviser. The deal was on the front page of The Wall Street Journal, the clients were dynamic, it was the tallest building, and it was the first deal of its size. I loved everything about it, from the people I worked with to the scale of the project. That experience really got me hooked on real estate.

— Andy Sucoff

Designing Offices People Actually Want to Work In

In addition to chairing Goodwin’s Boston office, I’m responsible for our real estate globally, and we constantly ask: how can we make our space work so people actually want to come in and collaborate? It’s a competitive environment for legal talent—if your offices have no light, no views, and the wrong technology, people won’t be excited to be there.

Your generation grew up working in places like Starbucks, often around other people, while others grew up wanting quiet, traditional offices. That’s why “live-work-play” neighborhoods like Boston’s Seaport are so powerful: there’s energy, restaurants, and things to do before, during, and after work. There’s a noticeable difference between that and an older financial district, and it really affects where talent wants to be.

— Andy Sucoff

When a Legal Structure Feeds a Neighborhood

One pro bono project that meant a lot to me involved a high school friend who started a fresh food bank in inner-city Boston. The city had property it wasn’t using well, and my role was helping him secure the right legal structure to control that real estate so he could build a warehouse and distribution facility. Getting that structure right meant he could collect and distribute fresh food directly into the neighborhood. It was a reminder that real estate law isn’t just about investment returns; it can have a very real, very meaningful impact on a community.

— Andy Sucoff

Law School and Learning to See the Gray

Law school teaches you to think a little differently and not see every issue as simply black or white. You’re constantly asking, “Is there another way to look at this? What are the implications if I frame it one way versus another?” Three years of law school is really about learning to see all the shades of gray and to think through problems from multiple angles.

— Andy Sucoff

Don’t Be a Scribe—Learn Your Client’s Business

One of the best pieces of advice I got as a young lawyer was that it’s not enough just to be the legal expert. If you really want to be a counselor, you have to understand your client’s business. Don’t just sit there as a scribe. Lean into what they’re doing, learn the business basics—accounting, tax, the market they’re operating in—so your legal advice is grounded in how their world actually works.

— Andy Sucoff

Two Ears, One Mouth: Listening, Curiosity, and Finding Your Passion

Being an active listener is critical. You listen, you reflect back what you’re hearing—“Here’s what I think you’re saying; is that right?”—and you keep asking good questions. Someone once reminded me that we have two ears and one mouth, and that’s the proportion in which you should listen and speak. People respect that you’re genuinely interested in what they’re doing.

I also try to live by this: do what you love and you never really work a day in your life. Finding that passion isn’t always obvious; it can take trying a lot of different things until something clicks and you think, “I like this—that felt good.” It’s a bit like falling in love. When you find that kind of work, you can look back after 36 years and still say you enjoy what you do.

— Andy Sucoff