Podcast with Jim Day, Founder and Managing Partner, Claritas Law Group (Part-1)

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Welcome, coffee enthusiasts and legal eagles to another delightful episode of LexDiscuss

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Cafe

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I am your host Avi and today we are brewing up a special blend of legal insights, golf

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antidotes, and maybe even a dash of hazelnut flavored contracts.

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Our guest needs no introduction.

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He was working as a senior corporate counsel at EquityZen and now he's working as a trusted

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C-suite advisor and outside counsel.

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Please give a warm cafe welcome to Jim Day.

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As usual, this will be a two-part series because I forgot to record the second part.

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Jim, thanks a lot for coming on the podcast.

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For our listeners who don't know anything about you, who don't know what kind of amazing

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background that you have had so far, do you want to give a brief introduction to themselves?

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Sure.

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I feel really lucky that to this point in my career, I've been able to associate with

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organizations that are solving what I think are really interesting and important problems

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and are doing things that are bigger than I am.

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And that was the thing.

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So my career to this point is basically broken down into three, maybe four major categories.

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I started off as a military officer, having gone to the Naval Academy, and from there

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after doing a JD MBA at Georgetown, transitioned into private law practice in large law firms.

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From there, went in-house at EquityZen, and now I have my own law firm where I'm sort

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of doing a hybrid private practice and in-house work where part of what I do is either an

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outsourced general counsel or an outsourced senior corporate counsel, typically for large,

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highly regulated technology companies and industries like SaaS, healthcare, transportation,

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some blockchain and anti-fraud types of organizations.

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And the thing that I really have appreciated the most is that I've gotten to be a part

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at various points in my career of things that were in the news, things where I felt

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like I got to contribute to a bigger organizational objective than just my own career advancement.

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So I got to participate in one of the most successful counter-narcotics operations that

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the U.S. Navy had ever launched in private practice.

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I worked on the financing of what is now a very large publicly traded electric automotive

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company representing the trustee in the Madoff litigation.

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And companies that I have been privileged to have represented since then are also, I

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think, doing a lot of really interesting and important work.

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So I currently have clients solving problems like how to make workflows more efficient

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so that the workers can organize their workflows more efficiently, collaborate with one another

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than email typically provides another client that is solving some really important problems

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in transportation and transportation technology so that people can better leverage the resources

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of their local communities and transportation access won't be a barrier for them.

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And so that's really been the primary aim of my career is just to align myself with

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people that I think are doing interesting things.

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Wow.

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Thanks for that context.

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You know, that's what brings me to the next question.

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With such a successful career so far, what inspired you to start Claritas?

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The main incentive for starting Claritas was I think that the legal industry is undergoing

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a rapid transformation right now where it is becoming easier and easier for costs to

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be lowered by sending work down to highly skilled attorneys who can operate with very

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little overhead and still produce work product that is as good or sometimes better than can

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be produced by much larger law firms and organizations.

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I think there's a real need in the marketplace for experienced attorneys that have multidisciplinary

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backgrounds to act not just as an extension of corporations and to help companies fill

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unexpected gaps in their labor force, but also to provide general consulting type of

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advice where they bring their experiences and their multidisciplinary approach across

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a variety of industries to help those companies implement best practices, particularly in

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the area of commercial contracting, but also in regulatory analysis and general corporate

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work as well.

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And so I am taking advantage of that need right now.

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And as I mentioned earlier, I've been fortunate to work with some really great clients.

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You know, your answer kind of inspired me to ask a little controversial question because

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earlier you were a corporate attorney and now you are an external counsel.

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Who do you think is more important for a company?

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I don't think it's either as more important than the other.

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They both have important roles to play.

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I look at it more as different types of problems need different types of tools.

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So it's kind of tools in a toolkit, if you will.

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So certainly for very complex at the company types of matters, whether it's a litigation

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or a transaction, you're going to want an outside law firm for that with a deep bench

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that has done that thing as many times before as possible and can provide immediate top

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of mind advice as to what works, what doesn't, what's normal, what's not, and can really

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provide that perspective.

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However, for things that are part of the day-to-day operations of the business, and that doesn't

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necessarily mean simple problems, but things that come up more regularly and predictably,

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I think those types of challenges are best addressed either from full-time in-house counsel

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or from hybrid in-house counsel such as myself, who are familiar with the business and can

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provide those services at a lower hourly rate.

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Good answer there.

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So yeah, that brings me to the next question.

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You are a former senior attorney at EquityZen.

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Could you share some of the key challenges that you faced and also with the advent of

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generative AI?

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Do you think this technology will help in some of those challenges?

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Yeah, for those in the audience who aren't familiar with EquityZen, EquityZen is a fintech

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company that is focused on providing a marketplace for privately held shares of venture-backed

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technology companies.

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So they're really solving a few different important problems within the fintech and

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startup ecosystem.

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So employees of startup are typically compensated in equity.

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They need a way to trade that equity for cash to pay for large and small living expenses.

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At the same time, ordinary investors who usually aren't able to invest in privately held companies

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because of the way our securities laws are written usually don't have that ability to

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invest in that asset class.

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That's a problem because private growth equity has been one of the highest performing asset

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classes, even after accounting for the downturn that we've recently experienced on a risk-adjusted

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basis.

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It's one of the best performing asset classes that I believe more investors need access

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to.

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So an obvious way to solve for that would be to pair those investors with the employees

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who need to sell their equity.

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That's where EquityZen comes in.

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And at the same time, you have issuers and the companies that these employees work for,

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they need ways to attract and retain talent by awarding equity to their employees.

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And that value proposition for the employees isn't going to work as well if there's no

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way for those employees to sell their equity.

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So it's pretty rare that you run into a business like EquityZen that has this win-win-win dynamic

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going on.

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The reason EquityZen is producing such a big value is because these secondary market transactions

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are just complex enough to not really lend themselves to the same sort of highly automated

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trading that we see for publicly traded companies.

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Every company that's just bespoke enough has just enough variations in the way they've

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organized themselves in their corporate documents, their bylaws, their rights of first refusal.

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All the things that go into that vary from company to company just enough that it can't

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be fully automated.

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It needs more of a specialized platform like EquityZen to make these happen.

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So I think AI generally helps people get some of these more repetitive tasks done faster

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and also helps people zero in on the most important elements of a deal.

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And so I see technologies like this as helping to further accelerate these sorts of processes

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that are in some ways susceptible to automation, but not all the way.

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And that's where the generative part of generative AI comes in, because it's not just a pure

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if X then Y, it's a predictive model that knows where the mean is across a variety of

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different transactions and can direct the participants of a deal to that faster.

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And so technologies like that do help companies like EquityZen that have, you know, regtech

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or fintech element to them.

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Thanks for such a great answer.

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My next question would be, you have been involved in various industries like fintech, e-commerce

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and healthcare.

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How do you adapt your legal strategies to suit the specific needs and nuances of each

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industry?

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Yeah, I'm not sure that the basic strategies really vary all that much from company to

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company.

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I mean, the core idea is that you start with a firm understanding of the overall business

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objectives of the client and look for ways that legal input and legal considerations

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can facilitate that.

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And at the same time, you're trying to uncover any blind spots that the business team might

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have missed or might not have anticipated.

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So that's always the basic exercise.

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But of course, from industry to industry, there's different regulatory regimes in place

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that you have to become aware of.

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So at a fintech like EquityZen, you have to become familiar with the securities laws.

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At a healthcare company, you have to familiarize yourself with things like HIPAA or with how

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insurance regulations work.

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And really, beyond reading things like practical law to sort of get a basic understanding of

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how things work, it really just takes a lot of trial and error and experience and somebody

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willing to trust you enough to give you that initial opportunity to get it so old and begin

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to learn.

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But once you've worked in enough different industries, you start to recognize patterns

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and you see that most businesses are more alike than different.

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All businesses need to make money.

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They need to sell a product or service for more than it costs them to produce it.

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And that's the basic concept that flows through to every contractual negotiation.

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And part of when I say more than it costs to produce it, we also have to account for

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the optionality of legal risk and that's where lawyers like myself come in.

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So my next question is, given your experience as a naval officer and military intelligence

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analyst, how has your military background influenced your approach to corporate law

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and deal-making?

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To corporate law and what was the other element?

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And deal-making.

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Different ways.

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I mean, I think the biggest thing that military did for me, when you're serving on a ship,

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you're there with two or three hundred other people that in all likelihood you wouldn't

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have met, wouldn't have interacted with, but for the fact that you're serving in the military

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and you're going to live with them in the very close quarters for six months at a time

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and they're going to become your family.

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And so that makes you adaptable to dealing with people with different types of personalities

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and makes you, I think, a better student of human nature, human motivation.

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And when you're in a negotiation and a deal, I think the most important principle of any

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negotiation is trying to move the conversation from talking about positions to talking about

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interests.

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So if I'm going through a contract and someone has a certain position that they want to take

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on a confidentiality clause, the best thing that I can do in that scenario is to find

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out what is it they're really interested in?

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What is the actual concern here?

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Are they just applying their corporate policy without really thinking about it?

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Or are they genuinely concerned that some important secret or trade secret of their

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business might leak out?

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And it's sort of that fine tuning to find what is the answer underneath the answer?

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What's the true motivation here?

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That was a skill that I first had to learn as a military officer where I'm leading and

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managing people from every walk of life, every conceivable background.

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And when you've done that, you start to realize that people generally are more like than they

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are different.

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Everyone has fears, they have motivations, they have dreams.

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And oftentimes in a negotiation, they tend to be very fear driven.

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So you have to understand what is the underlying concern or whoever it is that you're talking

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to?

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Are they afraid of looking bad in front of their boss that they want to save face?

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Are they genuinely concerned for what might happen if things go sideways?

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And just kind of getting that complete picture of human element, I think is something that

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machines will have a very hard time replacing and that's where human lawyers can add the

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most value.

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Wow.

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Such a great answer.

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A lot of people don't know that, that you have been recognized by the World Economic

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Forum and you actually received an award for innovation in wealth and investment management.

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What are your thoughts on implementing the latest developments in generative AI in the

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legal profession?

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Well, I have to quickly correct you there.

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I didn't receive that award, EquityZen did, and I had a very small part in that.

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In fact, I think that award was given before I actually got to EquityZen, so I can't claim

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any credit for that.

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However, I was at EquityZen when they were fortunate enough to experience a very strong

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growth.

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I'd love to think that I at least had a small part in that.

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I was part of a team of a hundred or so people that helped make that happen.

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And I think that when I think about generative AI in the legal profession, I don't think

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that it will ever replace lawyers or paralegals.

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I do think it will make it harder for them to profit from inefficiency and it will increase

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expectations around how much these professionals can do or expected to do and at what level

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of accuracy.

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So I think the main value proposition of generative AI is to more quickly guide attorneys

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to areas where they can add the most value, like the human element of negotiations that

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I mentioned earlier.

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And usually, the human beings in intractable negotiation are adding the most value when

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they're making judgment calls, which are informed by their experiences, oftentimes outside of

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the law.

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So to whatever extent AI or machines or technology can minimize the resources applied to everything

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else, that's going to be a tremendous benefit to both the earnings and their clients.

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Personally, when I'm working on a legal project, let's say I'm drafting a contract or drafting

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a legal brief, the most difficult and time consuming step for me is just creating that

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initial draft.

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So to whatever extent AI can get me through that first painful step the fastest so I can

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begin to focus on the best way to communicate whatever it is I'm trying to say.

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That's going to be a huge help.

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It'll move things along a lot faster and I think it'll produce better, less error-prone

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work product, which helps everyone.

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Kunti Greeno, would you like to share a particularly challenging legal case you have handled and

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the strategies employed to navigate it successfully?

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Sure.

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I think while I was in one of my in-house roles, I was tasked with helping our product

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team refactor its whole payment system and the way funds flowed.

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And so that involved negotiating through a whole daisy chain of contracts, each with

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different privacy and indemnification requirements.

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And the thing that was really challenging about it was that it was something that was

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critical to the business because it was the fundamental cash flows that were affecting

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the company and the number of different counterparties that were involved that weren't all necessarily

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talking to one another.

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So one of the skills that I've had to refine as I've practiced is sort of developing a

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sense as to how many people need to be involved at each different level of communication.

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So sometimes it makes sense to have an all-hands call with every single stakeholder on it and

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every single party on it.

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And oftentimes the fastest way to get things done is through one-on-one communications,

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finding out who the actual pen holder is for a particular party and just having a no-nonsense

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conversation with them about what their needs and interests are.

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So in terms of solving for that, first involved getting a real firm understanding of how our

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product actually worked, why we were doing engaging this exercise at all, and what were

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the legal risks involved.

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And then after that, it's really just sort of quarterbacking the deal and making sure

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that everyone who's involved has the information they need and the overall context behind why

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that information is being provided to them.

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And just through a lot of iteration, we eventually got through it.

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Such a great story.

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So the next question is, in your role as a visiting professor in Mozambique, what lessons

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did you learn that have shaped your approach to advising startups and entrepreneurs?

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So the opportunity in Mozambique was a function of having done an MBA at Georgetown University,

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which has a capstone project where the students are required to go to some other country and

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do a consulting project.

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And through that, I came into contact with the dean of a new MBA program that was getting

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started there.

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And he invited me to teach, which actually came as a bit of a surprise, but I left at

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the opportunity.

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And really, I went there and did the best I could to replicate a similar course that

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I had just taken at Georgetown.

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And the thing that I learned the most from that was I gained a new appreciation for the

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nuances of how different economic systems operate.

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So for instance, Mozambique, like a lot of sub-Saharan African countries, you don't actually

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own the land.

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You have to lease it from the government in many instances.

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And that has implications for how the land is actually managed and used and taken care

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of.

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And so I feel like I learned a lot more from the students that I was teaching than I possibly

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could have imparted on them from trying to replicate this course that I had taken at

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Georgetown.

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But I did learn a lot about how different elements of the Mozambican tourism industry

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operates there, telecom industry.

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When I came back to the United States, again, that helped with my overall pattern recognition

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of what are the similarities and differences between how an economy like Mozambique operates

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versus what we have in the United States.

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And there you have it, the first part of our conversation with Jim.

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Stay tuned and subscribe to our channel for the second part.

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Until the next legal adventure, this is Avi signing off.

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Stay caffeinated, stay curious and keep those legal marks refilled.