Caplan Legal

I’ve spent most of my career inside the business, not advising it from across the table.

That changes how I practise. I don’t start with what the law says. I start with what you’re trying to do, then work out how to get there.

Elana Caplan

Both sides of the table

I’ve been the in-house lawyer and the outside advisor. I’ve sat on the board of a payments company while it went through regulatory registration. I’ve asked for legal review and done it. I’ve negotiated for the bank and for the fintech, for the platform and for the merchant. When I tell you how the other side will react, it’s usually because I’ve been on that side.

The answer is rarely no

In payments and financial services, there’s always a regulatory reason to stop. A good lawyer knows when one is real. Most of the time, the question isn’t whether you can do something, but how to structure it, what it’ll take, and what you’re accepting by going ahead. I’d rather give you a clear answer with the tradeoffs laid out than a memo full of caveats that leaves the decision exactly where it started.

Risk is a business decision

My job is to make sure you can see the risk clearly. Whether to take it is up to you. I’ll tell you what I’d do and why, and how likely the bad outcome actually is, not just whether it’s possible.

Early is cheaper

The most useful legal work happens before the product is built, the term sheet is signed or the partner is chosen. I want to be there when the decision gets made, not cleaning up after it. The teams I’ve worked with best brought legal in early because it made them faster, not because someone told them to.

Build it so they don’t need me

Over time, you should need me less for the routine stuff. I write the templates, playbooks and approval rules so your team can handle ordinary deals and save my time, and your money, for what actually needs judgment.

Where this comes from

My first clients, when I started Caplan Legal in 2010, were Schedule I and Schedule III banks, U.S. card issuers coming into Canada, and the first wave of fintechs, and they all needed the same thing: a lawyer who understood regulation, contracts and product at the same time. I’d spent the years before in securities law and then in-house in telecom and at TD and American Express, so that combination was simply what I knew.