Bob Tarantino

2I'm good, Pulat. Thanks for having me on the show. I've been looking forward to this conversation.

4Bob Tarantino is a middle-aged guy. I have been a lawyer since the very late '90s. I graduated from Osgoode in 1999. I started my career in New York City, worked at Sullivan& Cromwell, came back to Toronto in 2001, and I joined Heenan Blaikie at that time. Eventually became a partner there. I was there until the very end when Heenan Blaikie collapsed in 2014. And then what happened was the, the entertainment group at Heenan Blaikie in Toronto moved as a sort of unit over to Dentons, which is where I am now. And over the years, so I— one of the things that I think has marked my legal career is that I occasionally sort of stop practicing law.

5So I sort of take these self-directed sabbaticals from time to time. I did that first in, in 2008. I went to Oxford and did a graduate degree there. And then in 2015, I started doing my PhD. And yeah, I'm just a, I'm just a guy who helps people make movies and stuff. I, I basically, I move paper around. That's my job.

7Sure.

9It's a good thing to get out of the way. So no, I'm not. So it's strangely enough, there's absolutely no connection between Quentin Tarantino and myself. I guess one thing I should also mention, somewhat related to that point, is there's another lawyer in Toronto whose name is Robert Tarantino. He and I are also completely unrelated to each other. So we sort of discovered each other a bunch of years ago, and we went out for coffee, I think it was, and tried to sort of figure out whether there was any connection between us whatsoever. And so there isn't. So it's a— to me, like, I'm not good with math, but I've always struggled to figure out what the sort of statistical odds are of two guys, both named Robert Tarantino, both practicing law in downtown Toronto.

10And like, we're roughly the same. I think I'm older than he is, but we're sort of roughly the same age. And yet having absolutely no connection to each other whatsoever. So, so yeah, no, I mean, having the last name Tarantino has certainly— it gets my phone calls returned quicker when I, when I call LA, but that's about it.

12Yes, I did.

14No, no. I mean, one of the— it's not that it's a secret, but one of the sort of unfortunate aspects of being an entertainment lawyer is that we never actually meet the interesting people. You know, in fact, there's— look, there's lots of clients of mine who are producers or directors or whatever who I've actually never met in person. I've only sort of corresponded with them or spoken to them over the phone. But yeah, no, Milla, never met her.

16A little bit, yeah.

18Yeah,

20It's a good question. I, I'm not sure that it's changed a lot in terms of the, the day-to-day practice of individual lawyers. So let Just to take a step back. So when I first was a summer associate, our law firm or the law firm that I was working at, at the time, we did not have internet access. So there was literally, or individual lawyers didn't have internet access. So there was literally one computer per floor that had internet access. And so if you needed to go to the internet, you had to sort of, you know, go to that computer and make sure that there was nobody else there. That being said, email was already sort of widely in use.

21And the sort of quickening of the pace of legal practice, I think, had already taken place. In other words, I think if you were somebody who started in the 1980s, so pre-email, I think the pace of legal practice was slower. Whereas by the late '90s, it had already— picked up significantly to the point where when a client reached out to you by email, they expected a response quite rapidly. I think what's happened in the sort of last 20 or so years is more at the systemic level in terms of legal practice, in the sense that it's much more fluid than it used to be. So when I started, it was still not unusual, but it was still sort of noteworthy when somebody left the law firm, right?

22There, people's careers tended to be much more stable. You tended to stay in one place for a longer period of time. That's, I think, disappeared now, right? Like, somebody staying at a single employer for, you know, 5, 6, 7 years, I think now that's almost the noteworthy thing. And I think also the profession has become— so I think the profession has diversified. I think the other sort of in a demographic sense, so it's a much more diverse profession now than it was 20 years ago. I think the other thing that has been important at a systemic level is it's much easier to start a legal practice now. And I think that's a function of technological change.

23And I think it's also a function of the community that has built up around new law and legal innovation. And there's— there are more resources, both in the sense of sort of, you know, documents and guidelines and sort of physical resources, but also there's more resources in the sense of people that you can speak with who are encouraging you to go out there and start a— start a practice and to explore different opportunities in the law. So I think that's that latter thing, that, that change in how easy it has become. Not that it's easy, but it's become much easier to, to start a legal practice. I think that's a real seismic shift in the way that the, the profession is structured.

25Yeah,

27I guess it— look, to give sort of the lawyer's answer, I guess it depends on what you mean by dominate, right? I think large firms play an outsized role in how lawyers conceive of themselves or how particularly how law schools conceive of lawyering. But, you know, like, just on the numbers, I mean, the number of lawyers who are at, you know, large firms, you know, is a tiny fraction. Like, you know, if you look at the 30 biggest firms in Canada, so if you sort of— which I think is a very rough measure of what constitutes Bay Street, you know, there's less than 4,000 lawyers on Bay Street. And, you know, just in Toronto, or just in Ontario.

28I mean, there's more than— there's close to 50,000 lawyer licensees in Ontario, so it's, you know, like not even 10% of the profession practices in large firms. But again, the, the large firms tend to play an outsized role in terms of not career prospects, but, but the, the vision or the, the landscape that's presented, I think, to law students. And also, I think the media conception of what lawyers look like and what they do and how they operate. So it's like an iceberg, right? Like that sort of archetypal iceberg where you can only kind of see the top 10% of the iceberg. Like this is a massive and very diverse and variegated profession.

29And the vast majority of it is not at a big law firm and is doing stuff that big firm lawyers don't do. And so, you know, there are more opportunities out there to practice law than are at law firms. And I think that tends to get lost in sort of the, the image or the, the self-conception of the, of the profession as it's presented, again, particularly to law students.

32Yeah, I don't think it's a dumb question at all. And frankly, I think, you know, when you talk about the, the discourse in sort of the, the legal tech space and the new law space, I think figuring out why clients choose big law firms is something that a lot of those conversations have never really grappled with. Like, they just don't understand why would somebody go to a big law firm because, you know, they're so expensive, there's cheaper alternatives out there. I think there, there's a couple of answers. So I think one is there are some types of work that you just need the infrastructure of a large firm to actually kind of play out.

33So large M&A transactions, for example, like you just need a lot of bodies to sort of throw at those sorts of transactions. And it would be very difficult, I would think, for a sole practitioner to, or even a small firm to do that. I think the other element of it, and this is something that I see in my practice, is if you have a firm like Dentons where we have a deep bench in the sense of we have entertainment lawyers like myself who, you know, do day-to-day what I'll call production work. I deal with the contracts. We also have tax specialists who have, you know, decades of experience in the entertainment industry. We have immigration specialists.

34So when we're flying people across the border or driving them across the border, as the case may be, we have lawyers who can deal with that. We have labor and employment specialists. We have people who are able to answer pretty much any question that comes up, no matter how unexpected it may be. And for a lot of clients, I think that's a real value add, right? That if something— so like immigration, for example, if they're having trouble getting an actor across the border, they don't have to call somebody else. They don't have to call another law firm, or they don't have to call their lawyer and then their lawyer goes, "Hmm, yeah, I don't really know the answer to that.

35I've got to find another their lawyer. They like the fact that it's one-stop shopping, that pretty much any question that they're going to pose, the firm will be able to answer in a fairly short period of time. So I think that's a critical piece to why clients, and particular types of clients, like having access to large law firms.

37No, no, definitely not patents. I'm just simply not equipped to deal with patents. But yeah, no, copyright is the biggest piece of the intellectual property aspect of my practice. I think also there's sort of some— I'll call them IP-adjacent subjects. So things like publicity rights or personality rights, defamation law, which sort of on an expansive definition of intellectual property, those are captured. That's the kind of stuff I deal with on a day-to-day basis. So my practice really has sort of two components to it. So one is what I'll call production work. And so that's helping people create things. Mostly it's film and television projects, but I do a bit of work in sort of all of the different facets of the entertainment industry.

38So I do some work in publishing, I do some work in music, I do some work in live theater and video games. So that's essentially, putting in place contracts, drafting, negotiating, and sort of interpreting contracts to get things done, to make a project happen. And then the other element of my practice is really a sort of entertainment-focused M&A practice. So when people are buying or selling music catalogs or film libraries or otherwise transferring rights or dealing with rights. And those, at the core of it, in, sort of 98% of the cases, the rights that people are concerned with are copyrights.

40Yeah,

42Yeah,

44And everybody's better off for that. Yes, I get it.

46right?

49These are big questions. I don't have a perfect answer. I have some thoughts on it, though. I think the— and look, a couple of— within the last few months, Richard Susskind, who's sort of one of the leading lights in the new law sort of legal tech space, he published a piece with one of his co-authors, where he essentially finally, in my view, conceded that his predictions about the pace and the scope of change in the legal industry were wrong because he had underestimated how complicated it is. And I think that's really the nub of it, right? So if you look at what it is that lawyers are called on to do, there are relatively few things that we do that I think can be reduced to a process or can be reduced to at least a process that can be outsourced to a computer or a device or something.

50So like, as an example, we'll go to, you know, the sort of stereotypical M&A deal. One of the things that happens in an M&A deal is the lawyers look at a whole bunch of contracts, and they look for particular types of provisions in those contracts. And then somebody has to make a call or provide legal advice on what the implications of those provisions are and give guidance on what the client should do in light of the provisions that they have found. You can speed up the front end of that process And that's been done successfully, right, by having AI and other sort of mechanized processes in place, which will go through the contracts and pull out those provisions.

51What you can't speed up is the second step, which is, okay, now that we know these provisions are here, what do those provisions say? And what are the consequences for our clients? Or maybe it's, it's better to say it's not that you can't speed that up, but it's much more difficult because that sort of analysis at that second step is very contextual. It's personal in the sense that you have to give advice to somebody who has to make a decision and you have to understand what their tolerance for risk is, for example. So that sort of thing can't easily be optimized with technology, I don't think, or at least we haven't done that successfully yet.

52You know, or to give another example, AI that's analyzing case law and saying, okay, given this set of facts, you know, we predict that the outcome of litigation or the sort of the probability of outcome A is this and the probability of outcome B is this. Great. It still doesn't tell me what to do in light of those probabilities. I know I have a 65% chance of winning the case. The computer isn't telling me, or the software or the device is not telling me what to do about that 65% probability. That's really— and giving that advice is really the thing that lawyers do. That's what we're sort of, I think, best positioned to do and what we're equipped to do.

53And so I think the sort of the push to dramatically change the way that law is practiced has underestimated or overlooked the sort of human component or the personal component of legal practice. So I think that's why you haven't seen those, as you describe it, those tectonic changes in the practice of law.

55Yeah, that's certainly part of it. I think I would extend that to say it's not just the facts of the case, right? Like, and I think this is the, this is one of the steps that, that a lot technologists miss. We have to extend that contextualization not just to the facts of the case, but to the client, right, and the situation that they find themselves in. So one of the questions that I think you have to contend with as a lawyer, and you have to counsel your clients on, is what's their risk tolerance, right? That's not really a fact. That's something inherent in the person that you are giving advice to. What's their budget?

56Do they have $500 to spend on legal fees? Do they have $50,000 to spend on legal fees? Do they have half a million dollars to spend on legal fees? The advice that you're going to give and the decisions that they're going to make are going to be very, very different in those different scenarios. And so it's easy to overlook how embedded legal issues are in very particular facts patterns. And that extends not just to the fact pattern in the sense of, you know, Person A did this to Person B, but the fact pattern includes the internal subjective, you know, views and proclivities of the individual client and the people on the other side. How are they, you know, if you take a position in a contract negotiation, It's not just a question of what position does your client want to take?

57It's an issue of, well, how's the other side going to react when you take that position, when you present that to them? So there are a lot of things which I'm convinced just cannot be automated, or at least can't be automated in sort of a timescale that's kind of relevant to us.

59Yeah, I think, look, the market is, is not demanding change in the way that I think a lot of people expected it to. And so I think one of the things you can look at here is like the billable hour. There have been critics of the billable hour for decades now, many of them very passionate. They are convinced that the billable hour is itself sort of a source of many of the ills that plague the profession and clients. But you don't see that many clients who are putting their foot down and saying, "We will not accept hourly billing as our fee structure." You see some, definitely. But I think part of that story is also that there's a caricaturing of different aspects of legal practice and of the industry.

60And there's been a caricaturing of the billable hour. So nobody that I know, and again, acknowledging that my experience is, you know, quite narrow but nobody that I know has ever sort of used the billable hour in the way that it's described in sort of think pieces arguing against the billable hour, right? Like, nobody that I know has ever said, okay, we start the clock here, we stop the clock here, and whatever that number is, we bill that and that's it, right? The billable hour is always just a starting point. There's always negotiations, there's always discounts, there's always— there might be additions or premiums for success. So the billable hour is much more malleable than it's presented as being.

61And so, yeah, I mean, the market-driven, the demand-driven change hasn't occurred because I think to a large extent, for the types of clients that big law firms service and for the types of, you know, activities that they need performed, big law firms do a decent job of delivering on

63So it's a good question. So I'm going to focus on sort of the production side of my practice. And so that, as I said, that, that's sort of where I'm helping people create things. Number one is contract drafting, right? So a film or television producer comes to me, says, we need— we're making a movie, you know, help us. And so what we do is we put in place all of the contracts. So there's an option agreement, you know, they, they want to adapt a comic book into a movie. So we have an option agreement, the agreement with the director, the agreement with the actors, the location agreement because they're going to film at some building, you know, downtown.

64We do all of that. So we put in place all of the contracts. The, the second big aspect is clearance. And so that's advising people, film and TV producers, on what they have to do in light of the fact that they want to include certain things in their movie, right? So they want to use a song in their movie. There's— they're going to shoot a scene where, you know, behind them, the two main actors, there's going to be a painting on the wall. One of the actors, you know, has a hat on and it's got a logo on the front of it. So we advise them on what it is that they need to do in light of wanting to include all of this stuff that's protected by copyright or by trademark or some other— they want to talk about somebody who's actually alive, or could they be defaming that person?

65And then the third thing is transferring rights. And so getting rights from— A to B to C, or vice versa, and taking the steps. And again, that's sort of a function of the first, of the contractual step there, but it's slightly different in the sense that it's got a different purpose. And so it has kind of a different teleology, but getting rights from where they start to where they need to end up. So those are the sort of the three things that confront me on a, on a daily basis.

68Yeah, great question. So look, I, I sort of share your your view about the difference between sort of what barristers do and what solicitors do, right? I'm not, I'm not completely convinced that we are the same profession. Right, like I sort of like the, the, the English model of these are really two different professions because we do such dramatically different things. That being said, in terms of that split, it's really a function of the sophistication of the client, right? So a lot of clients will come to us and they know exactly what the contract needs to have because they've seen those contracts before, they've done these kinds of deals before. And so in those cases, there's not a lot of education which is happening.

69When you're dealing with clients who don't have as much experience, you know, that's where you really start getting into— because their initial ask is always, okay, I need a really simple contract, right? Like 3 pages at the most. And you kind of have to go through the process of explaining, okay, well, we could do that. But that's going to be a really deficient contract. And that's going to pose all kinds of problems down the road. So here are the kinds of things that you need. So you need a termination termination provision in the contract. You need an indemnity provision in the contract. You're gonna need like an assignment provision. In terms of the grant of rights, like, I know you want it to be one sentence long.

70It's gonna make everybody's life easier if it's a page and a half long. So yeah, it's definitely—

72I don't know that I tell them, I advise them. So let me, like, you know, an easy example is they, let's say they want to license the rights in a movie. So there's a bunch of different ways you can describe that. You could say, "Party A hereby licenses to Party B the rights in the movie." That doesn't tell me much. What rights are being licensed? And then you can go from— you can say, well, we're licensing all rights. Okay, well, that's better. Oftentimes what you will see is we are licensing all rights, including— and here's a litany of the rights that we are licensing. And part of the reason that that dynamic exists is because contracts are really there to solve a problem if a dispute arises.

73And so it's great if you've got a contract, if a dispute arises, which says in very specific detail, here's the right that got licensed, as opposed to a very generic sort of, we're granting some ambiguous set of rights. So contracts are really just tools, right? They have a purpose. They're there to memorialize the agreement between the parties. I think that's one one aspect of them, but they're also there to forestall disputes or provide a resolution once a dispute arises. So, you know, look, there's tension there, obviously. Longer isn't always better, but shorter can be very problematic. So you try to find a happy medium given budgets, given the expectations of the parties, given sort of the realities of the situation that they find themselves in.

75Another great question. And I think to a certain extent, that's also driven by the sophistication level of the client. There are some— there are clients who you don't need to spell out everything for them because they have an understanding of kind of the background state of affairs in an industry or in a contract. And so you can rely on that knowledge to a certain extent. There's other clients who don't have that level of experience who you have to— it behooves both the lawyer and the client to spell out in great detail exactly what all the ambiguities, what all the potential pitfalls are, and what all the potential sources of conflict might be. That being said, again, To a certain extent, it can be driven by the client's budget, right?

76If the client, you know, only has X number of dollars to spend on due diligence, you know, and that's only going to pay for 10 hours of work, that you end up with a different work product than if the client has a budget that will, you know, accommodate sort of 100 hours of due diligence. So, and again, that goes back to the risk tolerance of the client. Some clients are happy to just sit there and say, "Tell us what the really important and big problems here are, and the rest of it, it'll sort of get figured out in the reps and warranties, or we'll get insurance to cover it or something." But due diligence is a— I mean, you're right to question it because it's a potential source for real liability and real stress in a relationship.

77Because if things go wrong, the clients, with some justification, are going to turn around to the lawyers and say, "Why didn't you catch this?" Or, "Why didn't you tell us that this was going to be an issue early on? We would've made a different decision." So it's a tough thing to navigate, or it can be a tough thing to navigate.

79So there's, there's rep and warranty insurance, which you can get for M&A transactions, which covers— it's kind of— it functions in a similar way to title insurance, right? The insurance company sort of does a risk scoping exercise and then prices it accordingly. And they'll say, okay, we'd like 'You know, we, for this number, for this amount of money, we will take on the risk that, you know, these representations are breached.' That being said, there's all kinds of other insurance that gets put in place, particularly in film and television production. So you can have cast insurance, you know, if somebody gets sick, if, you know, your star gets sick or, you know, injures themselves while they're hang gliding or something.

80There's production insurance, you know, if the cameras break or if, you know, somebody slips and falls while they're on set. So there are a variety of different ways that a client can attend to the risks that are inherent in what they're doing. Yeah.

82Yeah, absolutely. Look, it's a complicated world out there and there's lots of situations where clients will ask for a risk assessment. And I always try and qualify those things and say, look, I'm a lawyer. I'm not an actuary. If you want to figure out with real specificity what the risk here is, call your broker. To talk to them about how to deal with that, how to assess and deal with that risk. I can give you relatively high-level assessments, but those might not be worth the paper that they're printed on, frankly.

84I didn't. So I didn't actually get an undergraduate degree degree. I only did 2 years of undergrad. I worked, or I went to Western. I did 2 years of an undergrad in philosophy, but I knew I wanted to go to law school. And so I applied as soon as I could. And once that door opened, I walked through that door.

86I'm a very bad philosopher, but I think what the next 20 years for the profession are going to look like is there's going to be a— I, I think there's going to be a splintering of the profession, frankly. I, I think the profession has become much more attendant to and aware of sort of the, the, the subjective psychological impact on individual lawyers and how they deal with being a lawyer and the impact on them of practice. And as we sort of alluded to earlier in this conversation, you know, different lawyers are confronted with very different realities, right? My— look, I'm sure there are lots of lawyers who would look at me and be like, that, like, that guy's not really a lawyer.

87Like, he makes sort of— he moves paper around for people who are making things on Netflix. That is a very different life than somebody who is a criminal defense lawyer or a family law lawyer. I'm not completely convinced that the structures that we have in place, the governance structures that we have in place, are alive to that, like the disparity in legal practices. And so I would not be surprised if we start seeing a shift towards different expectations, different regulations, different reporting requirements depending on what kind of practice you have. And that, again, that's really a function of this broader shift, not just in the profession but in society at large, towards being much more sensitive to people's subjective experiences and how people's lives are lived.

88So that, that would be my predict— I think 20 20-plus years from now, the Law Society will look different, or at least the relationship between the Law Society and the people that it regulates will, will look quite different.

90I have to say, so I find— so one of the things, I love reading, I'm a big reader, but I do— I will say going to bookstores and going to libraries I find a sometimes depressing experience because I hate going in there and being confronted with the fact that there are all of these books that I'm never going to have the chance to read. Right? I find— so that's on the one hand, that's kind of— there's an inspiring element to it because it gives you a goal. There's like, oh, I got to read all these books. And on the other hand, you sort of end up with the realization like life is only so long and I'm just never going to get around to it.

91So yeah, no, thank you. I'm a big believer in the joy of reading. And the how it can enrich your life. So I try to, I try to read as much as I can, definitely.

93I like it. Let's make that happen. Thank you a lot. I really appreciate it.