Into that vacuum stepped Hamilton Chan, Loyola’s new Director of Executive Education at Loyola Law School. His new approach to legal education is already making waves, with many proponents labeling it “the Netflix of legal education.” It definitely isn’t your standard law school experience—Hamilton’s methods include video libraries, digital learning environments, and even paid actors and performers.

Hamilton doesn’t see this approach as new-fangled or high-tech; he sees it as the logical next step for legal education in general, and his diverse career path specifically. How does one person find success at JP Morgan, become a rising star at a prestigious national law firm, surpass expectations at MGM, and then find his way into cutting-edge legal education?

Find out in this episode of the Filevine Fireside, and learn more about Hamilton Chan’s education program at Loyola Law School’s website.


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Full Transcript

Katie Wolf:

Welcome to the Filevine Fireside, I'm Katie Wolf. There's no simple way to introduce Hamilton Chan. I've got to tell you about his time as a rising star at JPMorgan, and then how he left to be a rising star at a prestigious law firm, and then how he left that to be a rising star at MGM. And that's only the beginning of the story. After all that, he decided to run the family's printing business and create tech startups. Now, Hamilton has gathered the wisdom he's learned at each stage of his life and turned to education. He's an executive coach and a professor at Loyola Law School. He's the director of executive education at LLX, Loyola's new executive education program. Hamilton is here today to tell us about taking risks, finding your path and negotiating for success. Thank you so much for being with us here today, Hamilton.

Hamilton Chan:

Thank you so much for having me, Katie. It's great to be here.

Katie Wolf:

So you have lived a wild and varied life, if it's fair to say that, but can you give us the cliff notes of what your story is and how you ended up here?

Hamilton Chan:

Yes. More than happy to. I must say I have a slight aversion to Cliff's notes. So I'll go with Reader's Digest summary.

Katie Wolf:

Perfect.

Hamilton Chan:

And wild and varied definitely is all relative. I did not live in a cabin in the woods, or [crosstalk 00:01:26].

Katie Wolf:

True.

Hamilton Chan:

... jump off a cliff ever in my entire life. So it's really boring compared to most people's lives, but maybe actually compared to the standard corporate executive or attorney, it might be considered a bit of a boomerang career. So I will just say I, to give you a quick snippet of how I've come to be here. I was born and raised in Los Angeles. I always start there because I am the biggest fan of LA and all LA sports teams, and LA traffic that ever existed. So I was born and raised out here. I grew up the son of an entrepreneur. I started working at my family business, which was called Charlie Chan Printing since I was five years old. But the running joke in the family was always, should everything fall apart, and you do really poorly in school, career and life, there's always Charlie Chan Printing for you to work at.

Hamilton Chan:

And spoiler alert, I ended up doing it, but I did focus on school. I went to Harvard for college, and I majored in psychology. After that, I did work at JPMorgan in Hong Kong and in New York as an investment banker. I then went to Harvard Law School, came back to Los Angeles, practiced at a law firm called Munger, Tolles & Olson, representing Berkshire Hathaway, Kobe Bryant in his corporate transactional matters and large companies.

Katie Wolf:

Uh-huh (affirmative). Yeah, just a little known law firm, Munger, Tolles, you might have heard of it.

Hamilton Chan:

Yeah, I was definitely drawn to certain aspects of the firm, their strong academic side, I really felt like it was a company of great people. So I went there. I tried to make a shift in my career by moving into entertainment, and I ended up working in business affairs at MGM, that was very short lived. And I ended up saying, you know what? What I really want to do is I'm supposed to be an entrepreneur, that is ultimately the best expression of who I really am. So at that time, my parents said, we could use your help at the printing company, Charlie Chan Printing, the family business I grew up with, which I must say at one point in the eighties had a larger footprint in Los Angeles than Kinko's did.

Katie Wolf:

That's wild.

Hamilton Chan:

So we had about 14 locations right in the heart of LA. It was a thing. And I ended up taking over the company, running it for 16 years, and halfway through, I started a tech startup and I was running two businesses simultaneously. I went through this incubator called Y Combinator, raised a seed round of funding of about $1.7 million. And I thought I was going to explode from the stress of running the two do businesses. Fortunately in 2016, I was able to get a good exit for me and my family. And I left the business world and I started to help young tech founders on doing their own businesses. And I became an executive coach where I parlayed some of my psychology training and certainly a lot of my experience as an experienced entrepreneur.

Hamilton Chan:

And then about a year and a half ago, I got a call from the Dean of Loyola Law school, who actually worked at Munger, Tolles & Olson with me, and who graduated from Harvard Law with me. And he asked if I would help him start the executive education program at Loyola Law School. And I thought this was the perfect opportunity to marry my business side with my legal side. And so here I am today, teaching at Loyola Law School, running it as an entrepreneur, and also as a professor, and really, really excited to be here and to talk about everything and anything you want to talk about.

Katie Wolf:

So from the research I've done, at each point of your career, you were a rising star, and everyone wanted to hold onto you and say, no, this is who you are. This is what you're going to do. And then you left it and started something new. How did you do that? Did it take a lot of courage? How did you know when it was time to leave what had become perhaps safe in some way and start something totally new?

Hamilton Chan:

Well, thank you. That is a very kind interpretation. I honestly look at it as having no choice, and not being able to deny who I realized at that time I really was. I went into investment banking originally thinking, well, that's the Ivy League thing to do, and it looks like there's a lot of money. And for me personally, it was an interesting ticket to go to Hong Kong. I was born and raised in Los Angeles, but I grew up with a lot of strong Chinese influence. My parents speak Cantonese, I'd watched Hong Kong soap opera since I was a little kid. So my dream was to go and see what it was like there, and JPMorgan was the ticket to do it. But I realized before long that even though I picked the bank that I thought would be more the gentleman's bank, as they described JPMorgan, the culture still ultimately riled against me.

Hamilton Chan:

I went to an all boys school called Harvard High School when I was young. And I never liked that too much of that all guy culture. I always felt like it was like a version of Lord of the Flies, and I felt like I wanted something that was not the male locker room culture. And that very much was what it was like in the nineties in investment banking. So I knew that it just wasn't the right cultural fit for me, though I learned a ton, I really enjoyed financial modeling. I enjoyed presentations and pitchbooks and all that. I liked excitement. I liked all of that, but I just didn't like that other aspect of it. When I did the law, I realized that I was no longer doing any pleasure reading. I could never pick up a book at Barnes & Noble, I couldn't pick up a magazine and read a paragraph, because all I did at work was scan tons and tons and tons of documents. And I had lost my desire to read anything.

Hamilton Chan:

I also got tired of writing, because I was generating so many memos and contracts, as a corporate transactional lawyer, you're going to be doing crazy things like writing a paragraph that lasts half a page long with 17 semicolons, and keeps reiterating, provided however that notwithstanding the foregoing, blah, blah, blah, blah. And so I realized at some point that I had just reached an internal threshold for exercising that side of my brain. It's almost one of those thing where when you get good at something, it can almost become bastardized where that becomes the only thing that you do. And so I had reached my limit, I felt, within corporate transactional work at that time. And I couldn't deny to myself, but ultimately the true expression of who I am is somebody who would be able to exercise their creative side. So I felt like, well, what about strategy? What about design? What about managing people and leading people? What about crafting a vision? And I felt like all of that was left off the table in my work as a corporate transactional attorney. So I left that.

Katie Wolf:

So if others were listening in and are finding themselves dissatisfied, or incapable of going on in the career track that they have, what would you recommend to them?

Hamilton Chan:

Yeah. I remember a decisive moment in my college career when I met with a professor of psychology. And I was telling him that I was thinking about doing this investment banking thing. I had applied to law school and had gotten in, and I was trying to decide if I wanted to defer my admission and do the JPMorgan thing, or go straight in, or what in the world I should do. And he said that there was a study that was done on people facing major life and career decision points. And there was always the option of sticking with the tried and true, the status quo, or taking the road less traveled.

Hamilton Chan:

And it turned out that when they looked at people who took the road less traveled and did well, versus the people who took the road less traveled and did poorly, versus the people who stayed on the tried and true and did well, and the tried and true and did poorly, when they compared all those, and I guess they must have had a controlled group of people who never faced a major career life decision, but when they compared all of that, the people who had taken the offbeat path ended up being the happiest, this is all subjective. And there could be also some element of confirmation bias for sure. But there could be confirmation bias on maintaining the status quo as well. But the point that I learned from this was take that risk. You don't want to live with regret. You don't always want to be left wondering what if I?

Hamilton Chan:

So I think I've really led my career following that model. I hope those results were true and that the theory has not been debunked, but I will say from my own experience that, yeah, variety is a spice of life. And especially in this world that we live in today, I feel like people are changing careers and reinventing themselves every two or three years. So I'm really glad that I stayed ahead of that curve and it's worked out for me.

Katie Wolf:

Well, you have at least anecdotal evidence that it's true, whatever that study might say.

Hamilton Chan:

Yes. That's the most powerful thing there is.

Katie Wolf:

I want to talk to you about LLX, because it's such a unique program. Can you explain a little bit more what it is and why some people call it the Netflix of legal education?

Hamilton Chan:

Yes, I'd be happy to. So the raison d'etre, I would say for LLX, is post the 2008 recession a lot of law schools in America had to scramble, even the Harvards and the Yales and the Stanford Laws had to go and reckon with decreased applications and potentially reduced enrollments, and Loyola Law School was no different. And as a result of that, since 2008 law schools across the country have been looking for interesting ways to shore up their value proposition. And the Dean, Michael Waterstone of Loyola Law School, to his credit came up with this notion of, well, there's executive education for business school, why isn't there executive education for law school?

Hamilton Chan:

And so I really jumped at the possibilities of what we could do with this. I personally always thought that going to law school was a better value for me than going to something like business school, because I thought business school is great for networking and meeting people, but ultimately I would think that business is learned in the real life as opposed to in the classroom. Whereas law is such a technical field that you simply wouldn't know all of the vocabulary terms and the jargon and the statutes and how the whole machinery work together, unless you went through lots of class and lots of studying.

Hamilton Chan:

So I feel like executive education is actually quite a natural extension for law school. The law touches so many areas of life these days, and increasingly it's touching more. So I feel like it behooves folks to learn the law, even if they don't intend to practice as attorneys. And I think we all know people who will say, I always thought about going to law school, but I just didn't want to be an attorney. And so LLX provides those folks a chance to finally learn this material. Imagine, for example, the business person who deals with contracts every day, they're working in licensing at a music company, for example, but they've never taken contracts. They're not an attorney.

Hamilton Chan:

So we would provide a course where they can learn, all right, what is consideration? What is reliance? What is a meeting of the minds? What is restitution? How do all those things come together? And even more practically, if I agree to something over email, does that form a contract? If I put an attachment to that email, is that part of the new contract? So these are things really practical aspects, short form courses that we're delivering through LLX, that's what we call the program. And we're delivering it through three channels, online, on campus, and onsite where we'll go to companies and teach that.

Katie Wolf:

I think it's so exciting. Going back to this idea of lawyers being very risk averse, and not being useful for certain aspects of their job, do you have recommendations or ideas of what lawyers could do to open themselves up a little more to edge a bit out of that risk aversion when it comes to some of their technological decisions?

Hamilton Chan:

Okay. I like that last part of your question, because I was about to say embrace skydiving and bungee jumping, but to strip themselves away from the risk aversion towards technology, I think actually every lawyer should learn to code, and it's becoming almost cliche now that, oh, we should all learn to code. Maybe not everyone's meant to be a coder, but of all of the professions I feel like law lends itself most to code. If you look at a legal document, you're going to define terms, those are like variables in code. You're going to have certain clauses and contracts that get triggered. Those are like functions in a JavaScript program. So I feel like there are tremendous parallels between code and between law.

Hamilton Chan:

And once you learn to code, it's like Neo from the Matrix, waking up, and pulling himself out of the fake reality that he was in. You realize how much more you are capable of and how much more is possible. So I think when you learn to code, you're like, you know what? I could create a simple little program here that makes it so I can track my time more easily, or allows me to automate emails, or allows me to save templates for contracts, or pleadings. And I think that really diving into technology as opposed to being adverse to technology will make lawyers embrace technology more.

Katie Wolf:

That is a super interesting answer. So one of the courses that you are teaching right now is this in depth negotiating course, Negotiating for Success. Can you tell us about that?

Hamilton Chan:

Yes. I will say quite proudly that for some time in my career, I've been thinking to myself, when am I going to produce my magnum opus? When am I going to write a book that I can be really proud of, that I can put on the shelf? And in developing this course, and finally getting it published and present it on LLX, I really feel like this has been my magnum opus. I'm super proud of this class. It's a six week online course, and it includes 65 videos where I'm the professor teaching negotiations. It's a subject that I helped teach as a teaching assistant at the Harvard Law School program on negotiation. And it includes more than a hundred interactive exercises.

Hamilton Chan:

And what I really love about the class is that I feel like it's not an ivory tower class, it's not purely academic. We definitely go over the key terms in the fields of negotiations as an academic subject, but it's really colored with a lot of my life experiences negotiating. And if you want to learn negotiations, there's no better way to do it than to become a small, medium sized business owner. And that's what I was for 16 years.

Katie Wolf:

So, there's some obvious ways that lawyers use negotiation all the time, but are there some unexpected ways that you teach about where it's important?

Hamilton Chan:

One thing that I do emphasize a lot in the class is the importance of developing soft skills, and specifically how to build rapport. And this goes back into how to do business development, and how legal training might still leave something on the table for people to learn in order to actually be successful. One of the things that I try to do anytime I negotiate is I initially start by trying to build a rapport. And it reminds me of ninth grade history class, where the teacher says, pop quiz. You have 15 minutes, here's the subject. I need a short answer on the subject. And one thing that my teacher would always emphasize to me is make sure that you do not begin writing right away. Think about it. Plan. And some students would just go straight in and start doing the answer.

Hamilton Chan:

To me, it's like entering into a negotiation without bothering to build rapport, but negotiating the meat of the matter. It's just not going to go nearly as well. So sometimes I'll do a negotiation where 90% of the time we're just getting to know each other in the same way that I wanted to know whether you're in Salt Lake, and whether you like to be called Katie or Kate, and shout out to the engineer, Michael, and the great job that he's doing in the back over there, and getting to know him, this is just part of who I am, and this is part of how I approach the world. And I find that it makes an enormous difference, that way if I mess up, Michael will have no problem saying Hamilton we'll just cut out that silly little track that you did, and we'll resume right from there. So that makes people want to do favors for you. And that's what you're ultimately asking for in a negotiation.

Katie Wolf:

Did you just grow up with these skills, because of the family you grew up in, or did you figure these out at some point?

Hamilton Chan:

No, I definitely did not grow up with it. I think part of growing up from a second generation immigrant family is, in a lot of less first world countries, negotiation is [foreign language 00:18:32], expected. You're going to do it. You go to the market, you expect to negotiate, everything's supposed to be half off. And so I think that predisposed me, just seeing my mom navigate the world, even in America, and just demand the things that she wanted and be really a tough nut to crack, a strong negotiator. She's Chinese, but she grew up, was born and raised in Vietnam and left during the Vietnam war. So she was hard as nails and really an amazingly strong negotiator. So I learned stuff just from watching her. Then the other thing is working in business since I was young, since five years old, literally, I was used to seeing how we interact with customers and how there is always something at play, how people are happy when you give them just a little bit of a discount, rather than saying no, no discount at all.

Hamilton Chan:

So you learn these things over time. I used to be really shy and quiet, believe it or not. And it wasn't until I took speech and debate in ninth grade, and I got really into it and started competing in national tournaments and stuff like that, that I started to be able to use the power of articulation to combine with the context of seeing that things very much are negotiable. And when you combine those two things, you start to get better and better at it. I would say that the Harvard Law School class that I helped teach, and that I took in law school, that definitely gave me additional ideas on how to be an effective negotiator. And ultimately, I think it was cemented by 16 years of being a hard nosed entrepreneur negotiating with everybody, from employees to customer, to vendors, to banks, to whomever you can think of, buyers. That's really going to get you a lot of practice in that area.

Katie Wolf:

Yeah. I imagine it helps that you went through a recession as well while you were a business owner.

Hamilton Chan:

Yes. A lot of built up scar tissues in those days. For sure.

Katie Wolf:

You mentioned before that you have a background in psychology as well. I believe that was your undergrad. Right?

Hamilton Chan:

Yes. I was.

Katie Wolf:

Are you using those skills as well when you're teaching these courses?

Hamilton Chan:

I am. It's amazing because I remember specifically thinking, after I graduated from college, that I didn't learn anything, I was horrified. I was like, oh my gosh, I graduated from law school. The only things I learned were certain kinds of video games, where to buy Doritos, and the value of staying up late, and how much I can get away with procrastinating. But it turned out that quite secretly, my brain was picking things up in psychology. And I realized that I learned to see the world in a different way because of a lot of the principles that we were taught in psychology. So for example, one thing in social psychology, one of the tenets of social psychology is the fundamental attribution error. And the fundamental attribution error is that we tend to over attribute qualities to a person as opposed to their environment.

Hamilton Chan:

So if someone is amazing, we're like, oh, they're so great. They're such a great person. They're such a hero. Brad Pitt must be so nice, whatever it is. And if they've found themselves in a bad situation, we're like that person's a villain, they have a terrible heart. They're evil. They're not a good person. When in reality, so much of this stuff can be explained by the environments that led to these circumstances. I think Malcolm Gladwell describes it a lot more elegantly and eloquently than I just did there. But that gives you a certain humanism also when I'm an executive coach and I'm talking to people, I will try to get them to see beyond themselves so that they don't tend to over personalize and over attribute, and think that their failures, say as a startup founder, are entirely because of their own failings as opposed to something like market conditions.

Katie Wolf:

So that helps with both internal self forgiveness and empathy, but also building connections externally because you haven't just labeled a person as bad, or whatever it is, but instead you're reaching towards something that's deeper than the some of the things that they've done.

Hamilton Chan:

Exactly. I love the way that you put it. And I think another element of psychology and of connection is the notion of continually staying curious about other people. When you lack curiosity is when you've accepted that that is the way that they are. And even for yourself, when you lack curiosity about yourself, you're just accepting that these are the inputs and those are the outputs. But when you stay really curious, when you stay open minded, and you wonder why does someone think the way that they think? Then you have the potential to unlock your relationship, and find ways to reach understanding, and reach commonality.

Katie Wolf:

That's fascinating. This is going deep. You do have a depth of education in all of these subjects, I'm fascinated by this.

Hamilton Chan:

I'm glad we don't carry it one layer further, because I think I've gotten so abstracted, I really have no idea what's coming out of my mouth next.

Katie Wolf:

No, it could be anything. Speaking of next, Hamilton, what's next for you?

Hamilton Chan:

I'm happy in the present. I really like the institutional support that I've gotten for building LLX, just today we're actually launching our first on campus course, a class called Intro to IP Law, and it's being really well attended. So at this point now we really have such strong support from the professors here, the administrators, our larger college campus, Loyola Marymount University, from the Dean, and from our alumni base. So it's been so much fun just getting us to this point, and we're only getting started. We're going to record the next online class on contracts in early 2020. And we intend to roll out probably eight more online courses after that. There are really amazing productions, and we've tried to make it look absolutely like a Netflix, David Chang cooking show or something, and really get the best of LA talents, even in acting, we have actors in our classes to really illustrate the point.

Hamilton Chan:

So this has been fun and it has struck the right tones for me, or the right notes for me, of creativity, entrepreneurship, and also academics and intellectual activities. So, I'm really, really happy. I have no idea what's next, but as long as they'll have me, I'm here.

Katie Wolf:

After a lifetime of exploring new careers, you might have found something that actually just works long term, huh?

Hamilton Chan:

Yeah. Yeah. You never know. Well, especially if my employer is listening. Yes, I'm here to stay.

Katie Wolf:

Where can people learn more about LLX?

Hamilton Chan:

They can go to llx.lls.edu.

Katie Wolf:

I know I need to let you go, but my final question, you mentioned that you like to read, are you reading at anything good now?

Hamilton Chan:

You know what? There is a new book that I just picked up, I believe it's called Relentless, and it's about peak performance in sports, but also in life. I was actually speaking with a professional top tennis player that I was trying to help advise on what she could do with her career, and she's competing with the best and the best in the world. And she was talking to me about mindfulness, and how she wonders if that mentality has drawn away some of her dark side. And the interesting thing about Relentless is, it embraces the dark side.

Hamilton Chan:

So the author was the trainer for Michael Jordan and Kobe Bryant. And he's saying, own that side, you need that edge, nevermind all of this kumbaya stuff. So I decided to read it to get an alternative take on how people ought to be in order to achieve their greatest potential. And I think it is very much yin and yang, I do think that ultimately it is nice to have that reflective side and self forgiving side as you so well put it, that compassionate side, empathic side and the growth mind that side. But at the same time, it's nice to balance that off also with a certain amount of results orientation, and a certain amount of killer instincts. So I believe in both.

Katie Wolf:

That's great. I'm looking forward to your course on the dull of executive skills.

Hamilton Chan:

The dull of life? How about that?

Katie Wolf:

The dull of life, I'll take, yeah. Sign me up. Hamilton, it's been so wonderful to talk with you. Thank you so much for taking this time and sharing your wisdom with us.

Hamilton Chan:

It's been my absolute pleasure. Thank you so much, Katie and Michael, and look forward to talking again soon.

Katie Wolf:

The best of luck to you. You've been listening to the Filevine Fireside. Join us next time.