Jennifer: Let’s start with the basics…who are you?
Damien: I think it’s Brian’s turn.
Brian: We alternate.
Jennifer: That’s so cute.
Brian: We’re Weinstein & Klein, and we’re very cute. We’re a law firm that primarily works with small and mid-market companies, providing outside general counsel resources. Our three main practice areas are litigation, labor & employment, and general business/M&A.
We started in June of 2019, right before COVID, and have been growing ever since. We’re up to about 15 people now.
Jennifer: Wow. Okay, so when you say “small to mid-market,” what does that actually mean to you since everyone seems to define that differently.
Brian: My favorite answer is the New Jersey Small Business Council’s definition, if you’re over $50 million in revenue, you’re no longer small. Which is insane.
Damien: Or like 1,500 employees. Something equally stupid.
Jennifer: Yeah, that’s dumb. At what point does it make more sense for a company to hire in-house legal counsel rather than relying on outside counsel? Is there a typical company size, revenue, or stage where this transition usually happens?
Brian: It really depends on the project. We have a client doing over $100 million in revenue where we’re handling intensive litigation. Another around the same size where we act as outside general counsel. And then we’ve got small clients who call us constantly. So it’s less about revenue or headcount, it’s about how much time and attention they need.
Damien: But to answer directly, most of our clients have under 100 employees. Since we lead with employment law, we usually look at headcount as the metric. The sweet spot for us is somewhere between 20–100 employees.
Jennifer: So, you guys didn’t just graduate from law school and decide to go out on your own, tell me your origin story.
Damien: We like to say we’ve known each other for more than half our lives. We met as sophomores in college. I met Brian through my then girlfriend, now wife. She introduced me to her friend Brian from home. My first thought was, “I’m supposed to fight this guy, right? My girlfriend’s not allowed to have a guy friend named Brian.”
Brian: So lovable, though.
Damien: We went to different law schools, different practices, but we had two constants: over drinks we’d complain about our jobs, and half-jokingly say, “One day, maybe we’ll go out on our own.”
That went on for years. Then in 2018, Brian got fired, best thing that could’ve happened. He showed up with tequila, and suddenly the conversations got serious. Around the same time, my wife and I found out we were expecting our first kid. Not the best timing to quit my job, but maybe the best timing, too. After a lot of conversations, me, Brian, my wife, we said screw it, let’s do it. Brian had already been running a solo shop for a few months and we teamed up officially in June 2019. I walked away from my job which was terrifying, but worth it.
Jennifer: Love that. Brian, any color commentary?
Brian: Not much more to add. Damien was definitely braver quitting a job with a baby on the way. I just got fired. I was shocked I lasted seven years, honestly. Looking back now as an employer, I can’t believe anyone put up with me that long.
Jennifer: I get that. My husband tells me the same thing when I think about giving up: “You can’t work for anyone else now, you’re unemployable.”
Brian: Exactly. I’m a great team player, as long as I’m running the team.
Jennifer: And you guys are kind of a one-stop shop, right? Was that intentional?
Brian: Yes, from the beginning. We wanted to be a safe haven for small businesses. Big firms price them out, and solos often can’t handle their needs. We wanted to fill that gap, affordable, sophisticated, personal. Labor & employment is usually the entry point.
Jennifer: Like the gateway drug to all legal services is what you’re saying.
Brian Klein: We’re absolutely stealing that for our website.
Damien: Yes, we’re the ketamine of legal services.
Brian: Psilocybin maybe. Either way, once clients trust us with employment law, they bring us the rest. That was always the vision, start there, then build around it.
Jennifer: Anything you don’t touch?
Brian: Criminal law, bankruptcy, and patent law.
Damien: Patent especially, it’s too specialized. We’ll do trademarks, but patents we always refer out.
Jennifer: I’d like to talk about a trend I’m seeing, we’ve had quite a few law firms approach us over the past few months who left big firms to start their own. Why do you think so many partners are doing that now?
Damien: The legal industry is famously resistant to change, but a lot is shifting right now, AI, tech, client expectations. At big firms, people don’t have freedom, and clients are more cost-conscious. Smaller shops can be more competitive, and more people driven. Brian and I run Weinstein & Klein that way, we actually care about building a culture that’s good for our team. That’s basically heresy in our industry, but more lawyers are fed up with the old guard.
Jennifer: Makes sense. Have you ever fired a client for not fitting your culture?
Damien: Recently, yes. A good-paying client, too. But they disrespected one of our junior attorneys, and we won’t tolerate that. I don’t care how nice the invoice looks, if no one wants to take their calls because they’re scared of being yelled at, that’s not a fit for us. Protect the culture at all costs.
Jennifer: And that goes a long way for your company culture. I tell my staff the same thing, not every client is going to be unicorns and sunshine, but there’s a line between being pain in the ass and speaking to us disrespectfully.
Damien: You can handle demanding, you can handle needy, everything is a rush, everything is urgent, but disrespectful is a different thing, right?
And this even went beyond that, in my opinion, and Brian’s too. But yes, it’s happened before, and it’ll happen again, because that comes with being a service provider.
Jennifer: Agree. You both went from law school to working at firms, where clients were assigned to you. How has the transition been to running your own firm, where you also have to handle business development?
Brian: One of the great things about my firm was that even early on, business development was encouraged for young attorneys. My first week, I started thinking about networking opportunities, and within my first year, I joined BNI and really hit the circuit hard. That early exposure to business development is a big reason why, when I eventually got axed and had to start on my own, I was able, within just a few weeks, to bring over clients and keep momentum going while continuing to grow the firm.
That said, I know that experience is definitely not typical.
Jennifer: Same thing for you, Damien?
Damien: Yeah, I was your typical associate, head down, just doing what I was told, like a soldier. When Brian and I teamed up, I had to figure out the business side, strategy, marketing, networking, and the reality hit me: I had zero clients. The ones I worked with before were big clients at my old firm who would never follow me anyway.
I’d never networked a day in my life. I was good at legal work, billing, and checking off my to-do list, but business development was completely new. So I told Brian, “I’ve got nothing,” and together we made a game plan to hit the ground running.
And as we scaled and started hiring, learning the ropes of business ownership, management, and leadership? Totally new territory too.
Brian: Fortunately, I had seen Damien buzzed and drunk, so I knew he could be charming.
Jennifer: You’re a monster on LinkedIn, so it seems like you’ve figured that piece out, but the transition isn’t easy for everyone. We’ve worked with startups led by people who were at big firms, and we’ve seen just as many close because they can’t handle business development and running the business, these are new muscles. You two seem to manage both well, you’re growing fast, so kudos.
That said, why would someone go the outsourcing route with you versus hiring someone part-time in-house to handle everything?
Brian: Better talent at a more affordable price.
Jennifer: Even part-time?
Brian: Here’s how I see it: the best talent knows their value and usually wants full-time work, not part-time. Part-time roles limit the talent pool because skilled people want security, steady pay, and consistent hours.
Outsourcing solves that. Multiple clients needing part-time work can share a highly talented individual, who fills a full-time schedule across those clients, 10 hours here, 10 hours there getting the consistency they want. And you’re not just hiring one person; you’re hiring a team.
Instead of paying a full salary, benefits, and payroll taxes for one in-house general counsel, for a fraction of the cost, you get a team delivering the same or greater value. Whether through a subscription model, which we’ve been exploring, or an hourly model, you’re generally getting a full team in addition to that talented individual. That’s the big benefit of outsourcing: the expertise and support of a whole team for the price of one.
Damien: Exactly. And we’ve done that. Brian mentioned our subscription model, which we rolled out last year, which is steady monthly support.
Jennifer: Okay, let’s talk about your subscription model. That’s something unique to you guys, why did you roll it out?
Damien: The traditional hourly model sucks for clients and for us. Clients don’t want to call us for small things because they don’t want the bill, which means we can’t do our job as well. And for us, it’s unpredictable, high one month, low the next. As a small business ourselves, we need consistency. So we created a monthly subscription. Clients pay a predictable number every month for essentially unlimited access to our attorneys. Big-ticket items like litigation and M&A are excluded, but we discount those for subscribers.
Clients reach out more because they’re not worried about the clock ticking, which means we can actually protect them better. Like the number of times someone says, “I’m stuck in a five-year contract, no termination rights.” And we’re like, “Holy shit, did we let you sign that?” Nope, they just never sent it because it was a two-pager and they didn’t want to “waste our time.”
That doesn’t happen under the subscription model. They call us, we catch things earlier, and everyone’s better off.
Jennifer: I’m guilty of that. Not sending to you, when I should.
Damien: I know.
Brian: Jen, this conversation is about us, not you.
Jennifer: Ha! But I can’t help myself, from a finance perspective, if you know the average client uses X hours per month, what happens when they exceed that?
Damien: It happens. Early on, some months the client wins, some months we do, but the perspective shifts over time. The first month or two is usually hectic because we’re getting up to speed, answering questions, reviewing contracts, etc. But once we’re ingrained with the client, understanding their business and how they operate, things calm down. What seemed like overages in the beginning evens out, and the relationship becomes predictable.
Jennifer: You mentioned proactive versus reactive. I try to sell clients on being proactive—good bookkeeping, avoiding issues—but many call when there’s already a problem. How do you shift that mindset?
Brian: It’s always a challenge. Many clients only appreciate the proactive approach after something goes wrong—just like insurance. People buy it because it’s mandatory, not because they want coverage like good D&O, general obligations, or my personal favorite, EPLI. Those are “nice to have,” right?
The difference with what we do is we combine proactive measures with reactive support. With insurance, you just hope nothing happens, check your renewal, and pay your rates. With us, you’re getting proactive guidance to prevent problems before they occur, in addition to handling issues when they arise.
That said, it’s always going to be a struggle—it’s human nature.
Jennifer: Yeah. Over our business history, we’ve had a few “boomerang” clients—people who thought we were too expensive or didn’t need us, then came back mid-worker’s comp audit, realizing their files weren’t kept in order.
Damien: We’re usually good at breaking down those barriers. Take a client referred for a specific employment issue. Once they experience the subscription model, they realize they can also discuss contracts, exits, IP, etc., without worrying about cost. It’s included; they’re not being upsold.
Clients become receptive once they see we’re not taking advantage. Many have had prior experiences with firms where every email cost thousands. Once we break down that barrier, that’s when the magic happens. Clients start running decisions by us, gut-checking conversations with investors, vendors, partners, and it feels like we’re right down the hall, fully integrated into their business.
Jennifer: One of the things I’ve loved about working with you guys is that even when I have no real say in a contract, like with a major vendor, you let me know I have no options while clearly laying out the risks. Just knowing the potential pitfalls ahead of time is such a relief. I can’t imagine going in blindly.
It also surprises me when people sign contracts without really reading them. I’m not trying to be tricky, but I always wonder, did you actually read it?
Damien: You have to know the situation, what the client wants, and the reality. If you don’t have leverage, redlining every clause wastes money, and the other side will just reject it.
So, we call it as it is: “You don’t have much leverage. Here are the things to watch out for. Can you live with them?” If yes, we sign. If not, don’t.
Jennifer: I heard something that freaked me out. I heard a CFO speaking on a panel said they got rid of their general counsel because they’re using AI instead. People keep telling me AI will put me out of business in a year. I see it as a tool, but I guess some are treating it like their general counsel.
Brian: Those aren’t the clients we want. AI is replacing lower-level tasks, not high-level judgment. A great line: “AI won’t replace lawyers. Lawyers who use AI will replace lawyers who don’t.”
Jennifer: Love that! AI helps with summarizing or comparing versions, right?
Brian: Sure, but nuance matters. We don’t just explain legalese, we translate it practically: “You can’t negotiate this, but here’s what it means. Are you okay with it? Sign if yes, don’t if no.” AI can summarize, but without a guiding voice, it’s risky. You need someone to add nuance and verify accuracy.
Jennifer: Exactly. AI only works if prompted correctly. I heard travelers got the wrong documents because AI told them it was fine. It gave the right answer, but the person asked the wrong question. AI can summarize risks, but only if asked correctly: “I have no negotiating power, what are my big risks?” AI won’t figure that out alone.
Brian: Absolutely.
Jennifer: Is there anything I didn’t ask that you want people to know about your firm?
Brian: We’re growing. If anyone wants to join an amazing team in New Jersey, we’d love introductions.
Jennifer: Do they have to be in New Jersey?
Brian: Not necessarily, but they’d need to commute. Culture is important, and we value in-person interaction.
Jennifer: Are you in the office?
Damien: We’re hybrid and will stay that way, even in our new space. Everyone helps shape it, overseeing projects, choosing wall art, plants, decorations. It’s fun and meant to excite the team. Working from home is great, but seeing colleagues and chatting about deals in person has value.
Brian: That’s my extroverted side, I need people around.
Jennifer: That’s it—you guys did fantastic.
Damien: You could ask which of us is 40 and which is still in our 30s.
Jennifer: Oh!
Brian: Give me a few weeks, that might change. For now, this is my little brother, Damien.
Jennifer: You guys are so young!!
Damien: Are we still recording , can you say that again?
