1/2 chose to divorce

Welcome to another Founder Wisdom podcast. We have my friend Josh Skaknow. It's been a while, Josh, but yeah, Josh was running an AI business for lawyers. Now he is running his own firm. I believe it's in the family space, family law, and he's AI-fying his own practice. So want to talk about everything you're up to, Josh. Been some time. What's up, dude?

Yeah, I mean, we, we, I still have both companies. So, so we have a, and, and, and I gave up on family law, which we can talk about if you want, but it's, it's not as interesting of a story. So I started out as an immigration lawyer, co-founded a company. We built an immigration platform that powers a whole bunch of other immigration law firms across the country. Um, and now at the same time, I've, I'm continuing my own practice. and just really AI-powered, tech-forward law firms, starting with immigration. I'm actually looking to expand into family law and some other areas of law. So I'm looking for some like tech-forward lawyers who are maybe bored of the traditional practice, traditional law firm. But, uh, yeah, practicing, still have the tech company as well, which is fun. It's a nice little mix. And, uh, It's just crazy times with AI and what's happened over the last few years, and now it's happening, it feels like, every month or two.

Interesting. So what's been the latest pivot? Because last time we spoke, you went into family law. Now are you acquiring other firms? Like, what are you doing?

Yeah, I pivoted. So I spent the first 7-ish years of my career practicing Canadian immigration law. And quite frankly, I got a little bored and frustrated of it because we don't have to go all political here, but Canadian immigration shifted in a major way around 2023, 2024. It became a little bit more difficult and quite frankly frustrating. And at that point, I just felt like I needed a bit of a break or a change. So I, I tried family law, which for those who don't know, separation and divorce.

Mm-hmm.

And kids and money fighting and blah, blah, blah. And I did it for about a year and a half and decided, number one, it's not for me. Very emotionally charged, high conflict, stressful, all that kind of stuff. And then also, number two, harder to automate. It's harder to automate negotiating with opposing parties, going to court, that kind of stuff. So that kind of brought me back to immigration. And which is very different. A lot of the work is paper-based, easy to streamline, easy to automate, and it's still pretty difficult these days in Canada.

Like, emotional.

I mean, it's interesting. It's emotional in a different way. The work itself is not so emotional, but getting the results and helping your clients can obviously be very emotional, but more so for them, right? As opposed to your client and you're up against another party and they hate each other. And almost no matter what you do as a lawyer, they're probably still gonna hate each other, right? Not saying every couple that divorces hates each other, but I was doing a lot of litigation and it's usually the people who hate each other that end up in litigation, right? The couples that are in a better position, they mediate, they settle things out of court, right? On average.

I think all couples hate each other in that period of time. Maybe some of them like, uh, mend, uh, wounds after to just like spare the child, right? But I would say probably like 30 to 40% still hate each other after everything is done.

Yes and no. Like, hate is a strong word, right? They definitely dislike each other. It's not fun going through separation. But I would say there's a fair amount of couples who— or former couples— they don't hate each other. The relationship didn't work out. They're moving on. They don't like each other. The problem is when you're going through that process and you're trying to agree on what's called a separation agreement in Canada, there's a lot of things like these separation agreements can span 30, 40, 50, 60 pages.

Right.

So you may have started out pretty, pretty good, but as you start negotiating paragraph 32A of like, it's a lot of stuff. And so it ends, you know, in some cases it stays positive enough and you sign the agreement and you move on. But in some cases you don't see eye to eye on a few things, and all of a sudden people who just— they don't like each other, it didn't work out, that's fine. Now they're really butting heads because they can't agree on that, and they can't agree on that and that. And then depending on are the lawyers doing it in a more amicable way, or are some of the lawyers kind of fueling the fire and making it, making it a little bit more Confrontational, shall we say, so that they make more money or what?

Like, is that the incentive so that they spend more time? And I mean, that's the thing.

Family law in most cases is hourly. So there is a financial incentive for the lawyers to draw it out, cuz the longer you fight, the more you're billing right now. I will say a lot of lawyers are good people. A lot of the lawyers I were working with, I did not think they were fueling fires and trying, you know, I was practicing mostly in Toronto, the GTA, Ottawa, and I would say on average the lawyers were quite pleasant. They were good people. There's enough family law business to go around that there's good money, right? It's not like you need to drag on these files to pay the bills. And then there's all— it's like anything, there's always a few bad apples. I had a few files with opposing counsel who I thought very negatively about, shall we say, just to keep things PG here. But, uh, yeah, listen.

And then suits.

Yeah, I learned a lot. It's super interesting from like a psychology and like relationship. Like, I learned so much. Not to mention, around that time I had my first daughter, right? So you and I were talking before the show, I've got a 20-month-old daughter now. She was like just being born. And my God, did that— like, every day I would finish work, I'd come up and like kiss my daughter and kiss my wife and be like, oh my God, I'm so lucky, I'm so happy.

Yeah.

Right?

Yes.

So there's that too. But yeah, not for me. I've gone back to immigration. We do think there's a lot of opportunity to innovate in those areas of law that are still hourly billing. So anybody in the GTA who's a family lawyer and may be interested, definitely, uh, definitely reach out.

Did you get all these cases from post-COVID, right? Because COVID really fucked people up mentally. It fucked relationships up, right? Lots of cases of domestic violence and lots of divorces post-COVID. Have you seen that?

I mean, I started January 2025, a little over a year and a half ago now, right? We're September of 2026. So I don't know. I feel like the surge from COVID probably had ended by then, right? Like we'd been— we— everyone was mostly back to the office, but maybe not. Maybe there were some people that were holding on or saying, you know, hey, let's let the kids get one year older. I don't really know. That never really stuck out at me, honestly. I think the divorce rates are just so high in America. And yes, there's probably ebbs and flows, but like, and spikes here and there, but there's just always enough business. It's, it's sad to say there's just always enough business going around, right? I'm sure it's similar and it's definitely similar in the US and maybe some other first world countries. I don't know.

But, and why is that? Is it because of social media, people comparing themselves, this being super toxic? Plus, like, I don't know, people are, are higher mobility nowadays. I would say women have jobs, have their own independence, right? It's not the same values as before, not as much family time. Why is that?

I think a little bit of what you said. I really think the biggest factor— now keep in mind, I'm only 35. I've only been married for a few years. So I'm no expert here, but my opinion is that most people get married too early. That's my opinion. Because when you're 20, 22, 25, 27, especially for me as a man, like, I feel like I didn't even really— and, and curious to hear if you agree with this— biologically, I wasn't like fully ready to settle down, commit. And have a family until like 27, 28, 29, right? That's what I would say, roughly speaking. And so I also think I'm such a different person, like at 35, if you compare me to 30 and then you compare me to 25 and 20. So a lot of these people, and again, this is a generalization, but on average, if you meet somebody at 22 and marry them at 25, if you meet somebody at 19 and marry them at 23, if you meet somebody at 21 and marry them at 27. I don't think it's that surprising that by 35, 40, 45, maybe you're not happy anymore for a variety of reasons. Or maybe that person's not the right person for you, right? Like, I didn't get married until I was, what, 31, 32? And I'm happy about that because I've— now I know who I am, right? Like, can you relate to this? Like, 10 years ago, were you not a totally different person?

Yeah, but the core is still there. I think I matured pretty quickly as well. I was, yeah, I was pretty immature and then I matured all of a sudden when I started on this self-improvement path, when I discovered entrepreneurship, right? I was like, yeah, I can just keep on having all these partners and just fuck around.

But how old were you when that happened? How old were you when that shifted?

My serial Tinder hunter phase was like 19 to 21, but I happened to be an entrepreneur back then. So I was A/B testing that. I was like, no, this is not a life, right? This won't lead to stability and my higher goals financially, from a stability perspective, from a happiness perspective. And I maxed out this game. I was like, okay, I've seen it now. Like I've done that for a couple of years now. let me just go and commit to something, right?

Um, and when did you meet your now wife?

Yeah, 22. 22, Nadia? 23? Yeah, 22 or 21, I think, as we're pretty young, right? Um, but I was mature. I was very mature. I was the—

Pretty young, but you had that—

I was in the season of— I'm still in that season right now. Maybe I shifted in that season because I had a daughter, right? I think that's another new season of life. But I was pretty smart and thoughtful and thinking long term, right?

So, but you had that shift, right? So like, imagine if you had met somebody at 17, and you had a, and you had a 3, 4, 5 year old, and this is a lot of people, right? Especially in America, you meet somebody 17, 18, 19, you date for 3, 4, 5 years, and everything's fine. Or it's good enough. And then what's the next step? You get married. You're in your young or, you know, early or mid-20s and you get married, but then you maybe have a shift. You finish school, you start a new career, you become an entrepreneur, blah, blah, blah. And you're still my— basically my thesis is, and everybody's a little bit different, but you're still growing so much until you're like maybe mid to late 30s. For some people earlier, for some people later. And if you don't meet the right person once you're at that point, if you meet them a little bit too early and you kind of haven't figured things out, or people are going, you know, going on their own journeys, and if your journeys fluctuate too much, it should be of no surprise that you wake up when you're 28, 35, 42 and say, hey, this wasn't the person I was meant to be with. Now everything you said, that flames that fire.

Yeah, I had a friend exactly that divorced with, uh, Another person that I knew, like, at what, they got together at like 15, and then they lasted what, like 15 years together, right? And just recently divorced after they had kids. So to your point, right? And she's an entrepreneur. I think she was a dentist or something. Yeah, there's always like some financial stuff, right? If your partner makes like $200 grand a year and you're like— $200 grand a year. I make $60 grand a year. It's like, there's all these conflicts, right? And yeah, you're right with the identity stuff, but no, dude, I think it's a conscious decision. And me, thank God that I went in that direction 'cause I have like an addict's personality, right? And I don't think I'd be scaling the way I am today. And you need to have a rock when you're like wild and you take all these risks, right? Like you need to, that's the right decision for me. I'd probably not be in a good place I probably wouldn't be in an alley shooting, but I'd probably be, I don't know, like making respectable money but blowing it out and just like not being stable, going left and right, right? So I think like definitely a good decision. Also, this happened to me in my prior relationship before. I wasn't ready for it, and she kept like being, oh, like this, we need to be together, right? And I unsubscribe from that, right? And that led to my current relationships because I wasn't ready. I wasn't in the mindset of being stable and scaling from there. Let's talk about your business. Still fascinating topic because humans don't talk enough about relationships and how to not fuck them up, right? Which is pretty hard feat, to be honest. It's a very hard thing, which is why 1 out of 2 quit. And that's not to talk about unhappy relationships, right? Like some people stay together and it's even worse, like, than just ripping the bandaid off, right? It's like, it's just not positive. So that led back to immigration stuff. Okay. So what are you doing different now than you were doing when you started being an immigration lawyer? Tell me about some AI and agentic systems you run now.

Man, it's, it's night and day, right? So we, we, we have our own platform, we build on top of our own platform. And, you know, when I first started, I mean, this, like, even before I co-founded my tech company, right, this is 2017. I mean, what did practicing immigration law or most law look like? You emailed your clients back and forth and they emailed you PDFs and they, you know, uploaded Google Drive, you know, Google folders and stuff like that. And now it's just a totally, totally different ballgame. So we've actually built internally our own CRM. There's AI agents helping us manage it and nudge leads and poke leads and, you know, send follow-ups and stuff like that. We have entire workflows built out on the platform with document checklists and forms and stuff like that that get auto-filled. We do have internal AI that we're using right now to help us review files. Send feedback to clients, nudge clients, nudge us, you know, files are sitting too long, this, that, and the other. Probably the biggest stuff is some of the file review stuff that we're building. So we have an internal AI agent that helps us review files, make recommendations, help us process applications a lot faster and a lot more accurately. And we're working on a client-facing agent, almost like a, like a, like a concierge that would kind of work with our client directly to help get intake over and done with as quick as possible, right? Because the biggest thing, if you're a client, if you're an immigrant and you're working with a firm, is you need to download a whole bunch of stuff to that firm. You need to send them a bunch of documents and answer a bunch of questions, right? And you don't really need a human to do that, right? So that, so that's what we're working on to kind of help that make, you know, a lot better. And looking at other areas of law that we think lend themselves well to AI. So, you know, that's a fun part as well.

I need to plug you with a guy that is not a lawyer. He's a business guy and he acquires a bunch of these firms and runs them with his own system. And I think he's doing probably $10 to $20 mil a year with his law firm. And he has like 2 or 3 employees, which are lawyers, by the way, right? Yeah, that seems like an obvious strategy in your case, dude. Like fetch these law firms that are cash flowing, acquire them, meaning like, yeah, obviously do get some money, right? Like raise from LPs or from a bank and then slowly give them a paycheck throughout the years and have them finance half of it, right? Like that seems like a no-brainer. Is that where you're headed?

Yeah, I mean, we're kind of doing that at the same time. So, so growing organically in the form of, you know, ad spend, content, SEO, that kind of stuff, and also trying to look for firms, especially older lawyers who are kind of on their way out anyways. Because if you're a lawyer in your 60s, 70s, whatever, and you're looking to retire, there isn't like a like a Flippa for law firms, right? Like, you're not just going to list your law firm on an online portal, right? Some, some people might, maybe, you know, but at least in Canada, there's no like marketplace just for lawyers or for law firms. So finding the right lawyer at the right time in the right situation is— can be a little bit difficult. If there's any out there who are looking to, you know, sell and move on, then please, please reach out. Probably more activity in the US, as with anything, right? The US usually just— we lag them a little bit in terms of immigration or innovation and activity, and just because we're a smaller market in general. But yeah, in talks with a number of lawyers, hopefully looking to grow by acquisition a little bit as well. And, uh, that part is interesting too, learning about that process. I haven't done much M&A myself. I do find it interesting. Um, but there's the, there's the money side of it and there's the personal side of it, right? Like, these lawyers are looking for a firm that will take care of their clients, that will, you know, take care of their reputation and their brand and stuff like that as well. So kind of that double-sided coin of, yes, the numbers have to make sense for both sides. You also want to find a good fit because at the end of the day, if somebody's been practicing for 30, 40, 55 years They have some clients and, you know, who they know really well and respect one another and they want them taken care of. But I would love to connect with the guy that you mentioned. Is he based in Canada or the US?

US. Yeah.

Yeah.

Yeah. The thing is in M&A, you need to have a secret sauce, right? And which isn't that hard, to be honest. For example, me, you know, I've built like these go-to-market systems and as soon as I plug these into a company and I'm like, hey, founder, get the fuck out of the way. And I'm just going to plug my systems because most founders aren't even capable of implementing their systems. That's how bad most people are at sales, right? So if you have these proprietary systems and you can come in and almost immediately clack your fingers, implement your system and start seeing revenue, that's where it gets really interesting, right? So it's like cut the shit also, right? Like I'm also good at that. It's like I think most employees are useless and can be replaced by agents. It's way tougher than it sounds, right? But yeah, take that and maybe upsell some clients, re-sign some contracts. Like they're super happy, but a lot of founders are just scared to ask them like, hey, let's renew for another 12 months, right? And just because they're scared internally, not because the other party doesn't want to sign a longer contract, right? So I think it's super interesting, right? And it's challenging and it's risky as well, which makes all kinds of sense. But I think ultimately it's a huge time saver. It's like you come in, you spend very few time, you implement your system that are known to work, right? And you trust the system and you trust the numbers and eventually they go up incredibly fast. But yeah, you need experience for sure because It's highly possible to fuck this up as well.

Yeah, I mean, you won't know until you try. But the demographics— like, I've been saying this for years— there's all these boomers are already retiring and going to continue to, right? So everything we just talked about, plus the fact that there are so many entrepreneurs, lawyers, but way more than just lawyers, people who own businesses, whether it be a law firm, an accounting firm, a consulting firm, a tech company, a this, a lawn mowing business, between 50 and 70 who are going to be retiring soon. And those can be really good opportunities, especially like you said, if you can come in with a fresh set of eyes and no attachment to some things and just say, hey, we can improve this, we can tweak this, we can cut this, we can add this. And, you know, right out of the gate, like 2x the business sort of thing. So huge opportunity. I think anybody around our age or even a little older or even younger. Look for those opportunities. If you find the right person, the right business at the right time, could be a huge opportunity. Oh, you're muted.

I think you need to run to your next one. Where can people find out more about you, Josh?

LinkedIn is really easy. If you look up my name and you want to shoot me a message, you can check out my law firm at JoshuaShacknowLaw.com. That's a little bit more of a mouthful for spelling, or just Google Josh Shacknow and reach out. But LinkedIn, I'm pretty active.