Everyone told me how miserable law school was, so I decided that if I was going to be miserable, I at least wanted to be in a warm climate. That’s how I ended up in Florida, where I earned my LLM in taxation. This was around the time the US was changing its entire tax code and it was becoming an increasingly important area of law. I realised that if I knew more about it than other lawyers, I would be more valuable. I was always focused on scaling opportunity.
I got a job at a Miami firm called Fine Jacobson, which was the proverbial cat’s meow at the time. After I joined they merged with another firm, and that was the beginning of the end. I was only a baby attorney at the time, but it was clear that the integration was not going well, particularly on the cultural side. There was a sense of “them” versus “us” – and you never want that. It should always be a unified “us,” with “them” being external competitors. For any integration to work, there needs to be one profit pool, one management team, one chair, etc. It just doesn’t work if a firm is split into different factions. That was a key lesson I learned early on.
I then moved to Broad and Cassel, which has since merged into Nelson Mullins. I worked for the managing partner, Mike Segal, who still practices today. He was so kind and such a great mentor. He was transparent in showing me not only how to be a great lawyer but also how to be a great manager. I was dealt into a lot more meetings and projects than I should have been given my level of experience, but I leaned into it. They used to call me “the managing associate” because I was always volunteering for things, taking on managing roles and leading initiatives. People were like, “Who is this guy? Why does he care about this?”
‘I took the role of office head way too seriously! It was teeny – but I treated it as the most important office in the McDermott system’
I’d been there about five years when I got a call from someone I’d worked opposite on a deal who’d just moved to McDermott. He said, “I know you’re a healthcare lawyer, and this is the place. You’ve got to come here.” I loved Broad and Cassel, but I was impressed by McDermott’s reputation. I went to McDermott’s head office and met a bunch of lawyers who were all experts. It was crazy! I was like a kid in a candy store. I came in with various questions, and they’d say, “Oh, you should talk to Jim. He wrote these regulations when we worked at the government.” The depth of expertise was incredible, so that’s why I ultimately chose McDermott. But, as I always say, it’s like when you’re a kid and you leave your parents to go to university. It’s not that your parents did anything wrong, it’s just that this is the next phase of your life.
I was made an equity partner quite early, and pretty soon after that I got to head up the Miami office. I had a lot of support. I was very close with Mike Anthony, a pioneer in health law, and with a wonderful man named Larry Gerber, who is a mentor to me to this day. I took the role of office head way too seriously, and read every book that I could find on leadership. And this was a little office! We had about 17 people at the time. It was teeny! But I treated it as the most important office in the McDermott system. We were the little engine that could. Looking back, those were some of the most exciting days of my career.
I’m sure I made a ton of mistakes. We held mandatory partner meetings on Saturdays. Everybody joined, but I don’t think anybody liked it very much. We held them at people’s homes and rotated around, but they became an imposition. We also hosted a lot of happy hours and other evening events, which were also challenging for people who wanted to get home to their families.
‘It’s not that people around you are sycophants, but they believe in you – and that can create blind spots’
My biggest mistake was not seeing the world through other people’s eyes. You can’t assume everyone likes what you like. I’m a mountain biker and I always loved to take people mountain biking. But, as it turns out, it’s not everyone’s jam! I was shocked when I realised that not everyone wanted to jump at the chance to go mountain biking with me. Eventually I learned to take a broader perspective and I started suggesting additional activities – such as going to a basketball game – or starting after-work events at four o’clock instead of seven o’clock, so that people could still make it home for dinner and bedtime with their kids. Those little shifts made a big impact on building important relationships and a great cultural vibe.
I’m better at listening than most chairs that I know – but I’m still terrible at it. This is also true of most CEOs, but the result can be finding yourself in an echo chamber. It’s not that people around you are sycophants, but they believe in you and they’re aligned with you – and that can create some blind spots. You never want to stifle enthusiasm, but creating the space for people to feel comfortable bringing different perspectives and saying. “Hey, that’s not the best idea” is important.
What we’re seeing in the legal industry is: quality at scale matters. If you’re going to make a significant investment, whether it’s in AI, a new office, talent, or anything else that drives business – you need the scale to support it. Five years ago, if you’d asked whether you need to be a billion-dollar firm, a lot of people would have said no. But now, that’s not big enough. Clients today expect a level of sophistication that requires a higher level of scale.
‘We’ve been approached about private investment’
It’s time to seriously look at how law firms are structured. I always talk to my partners about having a bulletproof balance sheet, or what Jamie Dimon calls a “fortress balance sheet.” The traditional law firm model is, by design, quite fragile, given that profits are distributed at the end of each year. So, if a problem arises without a reserve, it can easily become an existential crisis. But when you’ve got two years of profits sitting in the bank, everything changes. You have security, flexibility, and the freedom to handle whatever comes your way – whether it’s a challenge or a new opportunity.
Having well-funded capital partners can be a very good place to start when it comes to building resilience. We’re already making big investments in AI and talent, and those costs are only going to go up. We’ve been approached about private investment, and discussions we’ve had have been very interesting.
The future of the legal industry is bright. McDermott’s best days are ahead of it. The next 100 years will be better than the last 100 years. Law is still an honourable profession and craft, and we should continue to nurture and respect that.
As one of only 12 LB100 firms to post double-digit increases for both revenue (11.7%) and PEP (12.2%), 
