J. Craig Williams is admitted to practice law in Iowa, California, Massachusetts, and Washington. Before attending law...
Bob Ambrogi is a lawyer, legal journalist, and the publisher and editor-in-chief of LexBlog.com. A former co-host...
Kate Nutting is a longtime producer for Lawyer 2 Lawyer on the Legal Talk Network. She also...
| Published: | September 26, 2025 |
| Podcast: | Lawyer 2 Lawyer |
| Category: | News & Current Events |
In this very special episode, Lawyer 2 Lawyer celebrates 20 years of podcasting on the Legal Talk Network.
Host J. Craig Williams joins former Lawyer 2 Lawyer co-host and host of LawNext, Bob Ambrogi, and producer of Lawyer 2 Lawyer, Kate Kenney Nutting, to chat about some of the exciting discussions we’ve had over the past 20 years. Take a walk with us down memory lane!
Special thanks to our sponsors Alexi, 1SEO, and SpeakWrite.
Kate Kenney Nutting:
Hi everyone. Kate Nutting here, producer for Lawyer 2 Lawyer on the Legal Talk Network. Our host Craig Williams is currently away on a well-deserved vacation but will be returning at the top of next month for a new episode. In the meantime, we have a special treat for you in this episode, Lawyer 2 Lawyer celebrates 20 years of podcasting on the Legal Talk Network. Craig joins former Lawyer 2 Lawyer, co-host and host of law next, Bob Ambrogi and myself to chat about some of the exciting discussions we’ve had over the past 20 years. Take a walk with us down memory lane. We look forward to bringing you a new legal topic every other week. Until then, remember when you want legal Think Lawyer 2 Lawyer,
Bob Ambrogi:
I keep remembering our very first or some of our earliest podcast episodes and we would have guests on and they would’ve no idea what a podcast was. They thought they were on the radio or something, so it was a funny time.
Announcer:
Welcome to the award-winning podcast, Lawyer 2 Lawyer with J. Craig Williams, bringing you the latest legal news and observations with the leading experts in the legal profession. You are listening to Legal Talk Network.
J. Craig Williams:
Welcome to Lawyer 2 Lawyer on the Legal Talk Network. I’m Craig Williams coming to you from Cape Cod, Massachusetts. Today I’m here with producer Kate Kenney and we’re celebrating 20 years of being on the Legal Talk network and running Lawyer 2 Lawyer and in honor of that achievement, we have some old guy that used to be around, not really is Bob Ambrogi. He’s a lawyer and a legal journalist. He’s been writing and speaking about legal technology, legal practice, and legal ethics for more than two decades. He’s been writing a blog since 2002. It’s even before we got started. Bob, he hosts Law Next the podcast that features the innovators and entrepreneurs for driving what’s next in law and he also writes a column on legal technology for Above the Law. He got started with us while way back in 2005 because you were I think originally a editor of the National Law General, so take it away, Bob.
Bob Ambrogi:
Yeah. Hey Craig, it’s so great to be back with you and yeah, I mean we hooked up back in 2005 when Lou Ann Reeb, the former founder of Legal Talk Network, reached out to both of us and said, I have this crazy idea for a podcast between two lawyers talking about things that are going on in the world and here we are. Here we were. Anyway,
J. Craig Williams:
Yeah, well at least with you up until 2018, I read on your blog I’d kind of forgotten how long it’d been, it seemed like yesterday, but Kate,
Bob Ambrogi:
13 years,
J. Craig Williams:
You’ve been 13 years with us and in that time I read on your website, I was surprised that we won a bunch of awards.
Bob Ambrogi:
We did. I guess I don’t even remember what we did, but I mean, heck, you know better than I do. You were the longest running podcast, but we were ahead of our time. I mean, I keep remembering our very first or some of our earliest podcast episodes when we would have guests on and they would’ve no idea what a podcast was. They thought they were on the radio or something, so it was a funny time.
J. Craig Williams:
We started with the woman who is with us on the show today, Kate Kenny Nutting. I think you were Kate Cuney at the time.
Kate Kenney Nutting:
I was Kate Kenny at the time, and then 20 years you get married, you have children, and a whole bunch of stuff goes on. So thrilled to be here with you guys. It’s been so fun. You’re my friends, you’re my family, so it is just always a pleasure being here and we’ve had so much fun over the years and Bob, we miss you and we’re thrilled to see what you’re doing. Yeah, we’re going to have fun today just going down memory lane and so here we go. We’re going to start off with some questions and then we’re going to get some answers and have fun with it. Our first question is why is it called Lawyer 2 Lawyer? Do you know how this started, Craig or Bob?
Bob Ambrogi:
Well, we actually started, we weren’t called Lawyer 2 Lawyer when we started out. We started out with the name coast to coast and the idea was Craig was on the west coast and I was on the East coast and he was a little more conservative than I was and I was maybe a little more liberal than he was, and we were going to be kind of talking about our coastal extremes, our political extremes, and I think as became kind of legend. The funny thing was that Craig and I ended up agreeing on everything rather than arguing about everything more, more than anything, but at some point we were threatened with litigation over the name of the show and Craig, maybe you can take it away from there, you responded.
J. Craig Williams:
It was George Nouri from the paranormal radio show coast to Coast who we were apparently using his name. I think he had a claim to it before we did in terms of time, but he had not copyrighted it, so we kind of wrote back and told him the ghost stuff himself. But Luanne and Scott were both concerned from, they were both news people from WBZ and Washington area rather in Boston, and they were a little afraid I think, of the litigation, so they wanted us to come up with a new name. We came up with Lawyer 2 Lawyer, so there we go, Kate. That was it,
Bob Ambrogi:
Which made more sense anyway.
Kate Kenney Nutting:
Oh, definitely. So I have another question. What’s a legal news story you think we didn’t appreciate its impact enough when it showed up in the news?
J. Craig Williams:
Well, for me it was COVID and it kind of has a double whammy. I know you’re going to ask me another question later and I’ll give you the answer to that one, but I don’t think we appreciated in November of 2019 that COVID was going to be as severe as it was and that we would be led down the path that we were led down about it.
Bob Ambrogi:
I have to entirely agree, I would’ve given the same answer. I mean, I remember being on a flight, I was out speaking at a conference on March 13th, 2020, which was like the day Tom got COVID and the Utah Jazz or something got, it was like this crazy thing that was all happening in the news all at once and I got on this flight and everybody was panicked, but again, I think we all fought, this is going to blow over in a little while and we’ll be back to normal. And then who could have known not just the impact on society, but the impact on law and technology and everything else has just been tremendous.
Kate Kenney Nutting:
Craig, we were able to get a guest at that time who clued us in on what was going on.
J. Craig Williams:
Exactly right, and that’s kind of the corollary to the first answer because of course when she came on the air, one of the things that she said to us was that she now couldn’t return to China because what she had revealed was going on in China. She said that on right in the middle of the podcast.
Kate Kenney Nutting:
Absolutely. I’m going to go to the next question here, Bob, you’ve been away from Lawyer 2 Lawyer here, but I know you have so many memories of what goes on behind the scenes. Can you give us a behind the scenes fun fact,
Bob Ambrogi:
I’m going to give you two fun facts. First of all, I thought an interesting fact was that given that we did this show for 13 years, I actually met Craig face-to-face two or three times maybe ever in all those years, which was kind of funny, but I mean understandable. He was on the west coast, I was on the east coast, but I think people thought we were close buddies who saw each other all the time, and unfortunately that wasn’t true. The other, I think one of my funny memories from the show is just how often either Craig or I were scrambling from some weird place to get connected and get online in time to actually record the show. I remember once being up at Acadia National Park in Maine trying to get a sales connection or a wifi connection, and I think as I recall, it was particularly critical that week because Craig was away and I was the only one who was going to be able to host it, and I actually drove to the top of Cadillac Mountain, which is the mountain in Acadia National Park, just trying to get enough of a connection signal to be able to get on, and it was like a minute before we were supposed to start.
I finally got the signal and finally connected in
J. Craig Williams:
The somewhat similar story I was driving, I think to Whistler and didn’t make it in time to set up my equipment for the podcast and did it from the car on my phone with my wife sitting next to me just fuming that I was interrupting our vacation that way.
Bob Ambrogi:
Oh yeah. My wife was sitting next to me during that whole Cadillac Mountain one, two. Yeah.
Kate Kenney Nutting:
Bob, to go back to you, I think during that time there was one point where the guest was talking and you both went out at the same time. So we’re sitting there and strangely enough we’re messaging Bob in the chat. Bob just say, okay, great. Great answer, great answer. You were both gone. So that was actually my behind the scenes. That was absolutely hilarious.
Bob Ambrogi:
I remember that, and it was like seamless when you listened to the recording, you never knew that we had disappeared out of it and had no idea what the guest was saying.
Kate Kenney Nutting:
Let’s see. I’m going to go to the next question here. What’s the most challenging topic or story you’ve covered?
J. Craig Williams:
I still think I would have to pin that because there was so much disinformation and misinformation about it. We were being told one thing by the government. We were being told one thing by the doctors. There were people in the streets who were flaunting it and we lost so many lives as a consequence of it. I was thinking we did that series Kate, on the life of a lawyer from start to finish as one of the things that Lawyer 2 Lawyers done. I read an article about the top 20 disasters in the world. It would be an interesting to do a series of shows on the potential for those things happening again and what the consequences would be, especially some of the solar flares that just fry all of our electronics. What our world would be in a situation like that, how we would have a rule of law and how we would function without electronic equipment would be just an amazing thing to explore. Bob, what do you think?
Bob Ambrogi:
Well, I mean I have to agree with you on that. I mean, that was obviously most difficult story we could possibly have covered in our lifetimes. Just to mix it up a little bit, I am going to also pick something else because these days my podcasting is mostly about legal tech and technology, and I have to say that covering the whole advent and evolution of generative AI has really been kind of challenging just because the technology is so unique and different and fast moving. The impact on legal practice is still so unknown. The impact on perhaps addressing access to justice is so unknown. So for me, I’ve been covering legal tech for you said more than two decades. It’s actually been three decades at this point. This has been kind of the most difficult technology to get my head around and to understand what the potential impact of it’s going to be. So not as dramatic as the pandemic, but it’s been a tough story to kind of cover and stay on top of.
Kate Kenney Nutting:
Okay, so I’m going to move on to the next one. Okay, so I have what’s the most ridiculous story you’ve covered or I can say what’s the most fascinating story you’ve covered? You can choose.
J. Craig Williams:
I think the story is the one where Bob and I interviewed and you found him, Kate, the lawyer who was out of a job and selling furniture.
Kate Kenney Nutting:
Yes, yes. Paul Za
J. Craig Williams:
And we put him on our show. We talked about him, and then he came back and told us he got a job, and to me that was just one of the most fantastic uses of a podcast that we got this guy back on his feet and back practicing law again.
Kate Kenney Nutting:
Yeah, I was buying furniture from my bachelorette apartment and I stumbled upon him and we just started talking, what a sweet guy. But you know what? At that time it was the recession and everybody was at a job and he had to do whatever he had to do to provide for his family, and we put that out there as a piece and someone heard and he was able to get a job that year. So now that’s magic podcasting and that’s a great one. That’s a great one.
Bob Ambrogi:
My most ridiculous story, it was actually kind of a little bit tragic and ridiculous, but I started, this goes way back, but I discovered that a legal tech founder who had been kind of the toast of the town, he’d actually even been selected to be on Shark Tank. He’d gotten all these awards. I found out he had been impersonating a lawyer, had swindled two clients out of hundreds of thousands of dollars. I reported it and it became this story that just kept getting weirder and weirder and weirder over the years to where I kept writing about him. It turned out he later got accused of trying to bribe several big city mayors. He then wrote this book in which he claimed to be an FBI mole through all this time, and in his book he had a whole section about me and my blog posts about him and how I caused him to lose this major deal he was about to enter into with LegalZoom to get acquired by Legal Zoom. LegalZoom denied that that ever happened at all, but this guy is currently serving time in federal prison for fraud. So a very, very strange and ridiculous story over the, it just kept going.
Kate Kenney Nutting:
Wow. Bob, that’s it. Let’s see. The next one I have, I’ll address this to Bob. How did you feel when you recorded your first episode?
Bob Ambrogi:
If only I could remember back 20 years, that would be great, but no, I do remember, I mean was really excited because I thought we were on the cusp of this sort of new cutting edge. I mean podcasts were very rare when we started this. This was not a big thing. There were in legal, there had only been a couple of podcasts up to that point that Denise Howell and had one for a while and maybe a couple of others, but we were doing something new and different, and so I was really excited about it. And I also do remember so much our first, our early guests, and I know you just had one of them back on the show. I think I remember Mike Greco, who was the just been elected a president that year. I had known Mike from the Boston area as a former mass bar president, and Mike was a brilliant, wonderful lawyer, but kind of old school buttoned up kind of guy, and I am sure he had absolutely no idea what was going on. I know he thought he was on a radio show. He didn’t understand what a podcast was. He was gracious in coming on the show, I think. So I just remember this both kind of excitement and a little bit of this feeling in my head of the humor of the situation of him not really knowing what was going on.
J. Craig Williams:
Yeah, Irwin Dean, Irwin Chemerinsky was our first guest and we had him on again for our 20th anniversary edition. He was dean of the UCI law school in Irvine at the time. Now he’s dean of the law school at Berkeley, and we have remained in touch over the years, which has been great. Recording our first episode to me was equally, I think as exciting as it was for Bob because I had a very significant radio background when I first started on the show. I had done commercial radio, college, radio, even high school radio and proudly hold still a third class FCC broadcasting license, a real rarity these days, but I was very excited to kind of get back into it. It was for me a good way to get a little promotion from my brand new law firm. I had started a law firm in 2003, two years before that, seeing some of the legal technology change thought, wonder what a wonderful way to ride this wave if it ever takes off podcasting, which it has, and be one of the founders.
I did do the research this morning, Bob. We are now officially the sixth longest running podcast straight out. There are five in front of us, one that started in 1995, but we are definitely, as you put on your webpage, and I got the two decades from your webpage, so time to update it on your webpage. You put that we’ve been doing it since August of 2005 for 20 years, and we are the longest running legal podcast by a long shot. I think the next longest running one is now from 2009. A lot of the ones that Denise Howells that you mentioned, and a lot of other ones have started and fallen off, but we’re still here and thanks to Kate, thanks to the Legal Talk Network that picked up our podcast after Scott and Luann sold it, becoming part of the Legal Talk Network now, I think what Kate 30 podcasts the network has?
Kate Kenney Nutting:
I believe so, yeah, and just growing.
Bob Ambrogi:
I remember in those early days of the podcast, I actually would go into the studio, the Legal Talk Network studio down in Norwood, mass down at your neck of the woods, Kate, and sit there and at their professional recording console, and Craig, I think you were in there once or twice over the years, and I remember sometimes we’d have visitors come into the studio and the a b ABA Journal editors were doing a road show one year they came in and sat in the studio and recorded their, I’m sure we could have done it all remotely. You were doing it remotely, Craig in those days, but for some reason I kept going out to the studio for a long time.
Kate Kenney Nutting:
Yeah, it was great having people in studio and see, my thing is when I would call up to book guests, they’d hang up on me. What’s a pod? I don’t even know what a podcast. You just want my money? And I’m like, no, it doesn’t cost anything. I’m just calling you because your expertise in the matter or the topic, so, so much has changed. Now, I sent out an email. I get an email right back before I used to be chasing down people. Anybody want to be on a podcast now? You send one quick email and thankfully there’s a plethora of people, of very intelligent law professors and attorneys out there who are willing to be on.
Bob Ambrogi:
Worst thing about having started my own podcast now is that I don’t have Kate do my own
Kate Kenney Nutting:
Booking. Let’s see. I’m going to move on to the next question. Bob, what is your favorite episode?
Bob Ambrogi:
It was like the most memorable podcast episode I’ve ever done, and unfortunately Craig wasn’t there for at, but it was the one we filmed in the Denver brewery. We recorded in the Denver Brewery that was adjacent to when Legal Talk Network got his building in Denver. There was a brewery, I don’t even know if it’s still there in the building, but there was a craft brewery, and there used to be these people who did a podcast of their own podcast called Foss Plus Beer, and Foss was free in open source law and beer was beer, and they would do a podcast about open source law, but then they would also drink a lot of beer and go to a brewery and record it. And so we got them to be guests on Lawyer 2 Lawyer, and we set up this whole recording in a brewery with all the Legal Talk network people in there, and Mike’s all over the brewery and they all came in and we started drinking beer and it was probably a good hour and a half before we actually started recording, and by that point, we were all feeling pretty good and it was really one of my favorite episodes ever.
Kate Kenney Nutting:
I love that.
J. Craig Williams:
I have to go back to the interview that we did, and you may remember it, Bob with a woman who was the United Nations monitor of trials in foreign countries, especially in Africa, to ensure that they were fair and reported back to us, and she described to us some of the circumstances. You’re trying dictators and you’re being threatened by their underlings and dangerous, very dangerous type of a job, but here she was standing up doing it, a single woman by herself on behalf of the United Nations representing the rule of law, and to me, she wore a cape and it was an amazing interview.
Kate Kenney Nutting:
Amazing. What’s one future headline you predict cover by end of year?
J. Craig Williams:
I think we’re going to see this current battle between Newsom and Trump really explode. The Democrats have been lacking leadership for a very long time since Kamala Harris backed out, lost the election. It’s kind of been a vacuum. Obama has stepped up in ways, but not completely. He’s not really in the political fray or our democratic governors really haven’t stepped up, but Newsom’s new PR team, trolling Trump is I think going to come to a head with this redistricting issue. We just did a show on that and we’re going to have to continue to cover that because what’s going to happen in the midterm elections,
Bob Ambrogi:
The headline I predict we’re going to see by the end of the year is Legal Talk Network announces its honoring its original two podcasters with grants of $1 million each. Woo. You think we’ll see that we
J. Craig Williams:
Win the lottery. Bob
Kate Kenney Nutting:
Craig, I have one final question for you specifically. Do you think it’s time to update your photo on the show artwork?
J. Craig Williams:
I think it is, and I do have some headshots that I need to dig out and send to you. I need to update my profile picture on so many different platforms. It’s a task I’m really sure I want to undertake, but I’m not the same person that I was when I started because of the pandemic, my hair grew and I didn’t go to a barber like they told us not to. And after it was over, I thought, huh, kind of liked it long. So I let it go, and now it’s almost as long as my grandson’s hair who hasn’t cut his hair in. I think the 11 years of his, or seven or eight years of his life,
Bob Ambrogi:
The show logo looks a lot better without my face on it. I’ll say that.
Kate Kenney Nutting:
Oh, stop. Bob, stop.
Bob Ambrogi:
What was the story, Craig, about you once you were in Australia or something and somebody came up to you and said, don’t you do the Lawyer 2 Lawyer podcast or something. Am I making that or did that happen?
J. Craig Williams:
No, that actually happened. I had gone to Australia in 2008 or so very early on, and I was in Sydney and I had climbed the bridge, taking a flight on a float plane and then some other things, and I think we did a ghost tour, and I was in a bar kind of late at night after that tour or during it and walked out and somebody recognized me like, you got to be kidding me. I’m in Australia. Who’s ever heard of this? And apparently at the time, somebody had done some research at the Legal Talk Network and found out that, I think it was Scott who said that we had, we have listeners, he was able to track the URLs to the Supreme Court, and we had listeners on the Supreme Court. So it’s been really interesting. Kate has done a fantastic job with a guest. We had a guest from Hong Kong. We’ve had guests from England, the continent, so we changed our timing for that. So it’s been a real wild ride over the years, and I still love doing it. Kate still gets great guests and because we’ve been on so long, as Kate says, it’s much easier for us to get those kinds of guests.
Bob Ambrogi:
We somehow got an email or something from somebody in Russia who told us they were using our podcast to teach English as a second language or something like that.
Kate Kenney Nutting:
Yes. How cool.
Bob Ambrogi:
Yeah,
Kate Kenney Nutting:
Legally, yeah, in English, yeah,
Bob Ambrogi:
To their studio. You never know who’s listening or watching.
Kate Kenney Nutting:
Guys, this has been so, so fun, and I appreciate you. Happy 20 years, Bob. You have your own podcast. Let everybody know about that.
Bob Ambrogi:
Yeah, I have a podcast called Law Next. You can find us. Just Google it Law Next or it’s law next.com is my blog. You can find it there. We also, every Friday, do a live podcast Legal Tech Week with a whole panel. Joe Patrice is other legal talk network host and other people. We get together every Friday afternoon live at three and just it’s sort of like sports talk for legal tech.
Kate Kenney Nutting:
Hey everyone. Thank you for listening to us over the years. We appreciate your feedback. Feel free to always reach out. It’s been a great 20 years. Here’s to 20 more and keep listening.
Announcer:
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Lawyer 2 Lawyer is a legal affairs podcast covering contemporary and relevant issues in the news with a legal perspective.