The Billable Hour is Broken: How Blackletter is Redesigning Law for Startups | Jonathan Rosenbluth (CEO and Co-Founder)

Jonathan Rosenbluth (0:01)

Any time you have a client thinking, should I call the lawyer or message them? Am I going to be billed for this, or should I just take the risk? That's a bad experience. So if one of our clients wants to call us, we won't charge them for that call, because that's a bad client experience.

Matt Cohen (0:14)

Welcome back to Tank Talks. I'm your host, Matt Cohen, founder and managing partner of Ripple Ventures. And in this week's episode, I'm chatting with Jonathan Rosenbluth from Blackletter Law. John has one of those backgrounds that only makes sense in hindsight. Harvard Law, McKinsey, and then it's time at Cohere, where he joined the company as a small seed startup, as the first non-engineering hire, and stayed all the way through to $6.8 billion valuation, working BD, partnerships, and GTM while the company scaled.

Now he's building something that most people in legal tech are not building, Blackletter. As John explains, he's not just building a co-pilot bolted on to big law, it's an actual law firm. No billable hours, just flat pricing, same day or next day contract review, elite lawyers in the loop, and a multi-agent system underneath that remembers the client instead of starting from zero every time a new MSA shows up. He started it with his co-founders, David Stewart and Avi Brindner. Frontier AI infrastructure on one side, big law and legal ops on the other. Today, we're going to talk about why billable hours exist in the first place, why they had built a firm instead of another legal SaaS tool, what actually happens when a contract hits their pipeline, and why Jonathan pushes back on being lumped in with the AI native law firm Wave. This is an eye-opening conversation about how Blackletter is revolutionizing one of the oldest service-based industries in the world, law.

Now, let's jump into the tank for this week's episode with Jonathan from Blackletter. Thanks for joining us in the tank today, John Rosenbluth.

Jonathan Rosenbluth (1:47)

It's great to be here.

Matt Cohen (1:48)

John, it's great to have you here and to talk more about what you're building, but I want to go back to your background because it's quite unusual. Harvard, JD background, and then McKinsey, walk us through a bit of your early childhood experience, where you grew up, how you ended up thinking you were going to do law, wanting to do law, ended up in consulting before we get into what you've been doing recently.

Jonathan Rosenbluth (2:08)

Yeah, I grew up in Toronto, childhood Mark Basely, but I just playing as much baseball as I can, watching as much of the Blue Jays as I could.

Matt Cohen (2:15)

Born in 92, so you didn't get to see the World Series, but you were born and alive at that time.

Jonathan Rosenbluth (2:19)

Yeah, sort of taking it in through osmosis, I guess. We got close, we got close last year.

Yeah, I studied history in undergrad, and when you're in a history major, the natural path is just to go into law. It seemed interesting, it seemed like a place to have impact, to build a career, and then I went to law school. I loved law school, fascinating, but when I would be doing my summer internships, it was just clear that practice was reactive, it was siloed, it wasn't a place to actually build, and so I left, which is a little bit unusual.

Matt Cohen (2:47)

Did you talk to people about that while you were working in law and saying like, hey, how do you get excited by this practicing of law when you were questioning it so early in your journey?

Jonathan Rosenbluth (2:56)

Yeah, I spoke to one lawyer, this one sort of sticks out, and he was like, I get really excited by the number of zeros in a deal. I was just, that's not how I'm wired.

Matt Cohen (3:06)

Right.

Jonathan Rosenbluth (3:07)

So it didn't fit. I went to McKinsey in my 2L summer, I split it between a law firm and consulting, and consulting was forward thinking, problem solving before the problem occurs, and that just let me out.

Matt Cohen (3:20)

Something off. What was your first few projects you were put on?

Jonathan Rosenbluth (3:22)

Working for financial institutions in Canada, in the US, and even in Jamaica.

Matt Cohen (3:28)

Wow, a lot of travel?

Jonathan Rosenbluth (3:30)

A lot of travel.

Matt Cohen (3:30)

What was the best experience you got out of the McKinsey years?

Jonathan Rosenbluth (3:33)

McKinsey's got a great culture and feedback, and it's people who are invested in each other and helping each other grow more so than I had seen at any point in my career. And that was super exciting for me.