The Legal Toolkit

What’s the next big thing coming in AI? Autonomous agents, that’s what! Currently, you have to drive the process of genAI by honing the iterations of your prompt. But, an autonomous agent can do that stuff without you worrying your pretty little head, dear lawyer. So, what’s there to know about this latest tech evolution? Jared’s here to talk about attorney use cases and whether this tech may be used for good or ill. Later, the AI apocalypse isn’t upon us yet, so let’s enjoy some awesome music. Jared welcomes Rock and Roll Hall of Famer Richie Furay who, among other accomplishments, was a member of the great American bands Buffalo Springfield and Poco. Jared and Richie talk through his history, digging into many colorful moments from his experiences in the music industry. Richie performs live on the podcast, and he and Jared discuss his upcoming documentary. ----- Need more Richie? Jared's got you covered. ----- Mentioned in this Episode: Spellbook Associate, effectively acting as a junior associate in a law firm. Spellbook Launches Gen AI Agent that Can Plan and Execute Complex Transactional Workflows | LawSites by Bob Ambrogi LawNext Podcast: Ep 256: All About Spellbook’s New AI Agent, Capable of Performing Complex Legal Tasks, with CEO Scott Stevenson Richie Furay Documentary — Richie Furay

Dear lawyers, software integrations exist to help you make life easier, make work faster, and much more. So, get on board as Jared takes us on a magical journey of understanding, helping lawyers everywhere grasp the versatile, customizable integration possibilities in legal practice. Jared explains the differences between direct, indirect, and DIY integrations, and gives real-life, legal-centric examples of how to amp up the usefulness of your software in almost innumerable ways. Next, there are definitely some issues with our current legal ethics rules, but is there really any way to clear up the confusion? Jared welcomes legal ethics expert Jayne Reardon to talk about some of the inconsistencies at play, antiquated rules, inconsistent enforcement, and all sorts of other ethics questions worth examining in view of the current climate of the profession and needs of consumers. While Jared wants to burn it all down, Jayne offers constructive criticism vital to the future of legal ethics. And, finally, the Rump Roast, of course! Jared and Jayne play a round of trivia called “Questionable Ethics”. Which philosopher had a penchant for being swaddled like a baby? Yikes. Jayne R. Reardon is a Partner and Deputy General Counsel at FisherBroyles LLP, a distributed global law firm. ----- This week, Jared shares the playlist he turns to for help making the "right" choice. Proceed with caution. ------ Our opening song is Two Cigarettes by Major Label Interest. Our closing song is Something Else by Nu Alkemis$t.

If you’re not marketing your law firm well, you’re sitting on a whole lot of untapped potential for income and growth. Jared talks to Ashley Robinson of Green Cardigan Marketing about the need she saw in the legal world for honest, straightforward marketing tactics that help law firms bring in new clients and greater profits. She explains engagement strategies, effective intake processes, essential marketing technology, and more. Later on in the Rump Roast, Jared and Ashley play “Don’t Sweat It!”––a delightful round of sweater-related trivia. And, it might seem like Sheryl Crow got a late start to her music career, but she was deeply involved in the music industry for many years before her breakthrough solo album, “Tuesday Night Music Club” rocketed her to fame at age 31. That first album was pretty fun, but Sheryl’s perfect album came later with “The Globe Sessions.” Jared digs into the exceptional appeal of this deliciously hard-edged pop/rock album. ----- Yes, Jared does have a playlist of his favorite Sheryl Crow songs. ----- Our opening song is Two Cigarettes by Major Label Interest. Our closing song is Golden Light by Reveille

Too many law firms aren’t great at being productive, and downfalls in efficiency are often traced to attorneys using the wrong software, or none at all. Jared outlines six productivity-boosting software tools all lawyers should have in their toolkit. Later, what’s going to happen to your law firm if something happens to you? Don’t wait until late in your career to establish your succession plan. Start early and communicate well to make a plan that protects your legacy and those you care about. Jared welcomes Ivy Slater to learn the ins and outs of succession planning. And, last but not least, what past Olympic event involved two opponents whacking each other with canes? It’s that time of the quadrennial again—so “The Shitty Olympics” returns to the Rump Roast! Jared describes a variety of absurd former competitions, and Ivy must guess the events. Ivy Slater is CEO of Slater Success, a consulting and coaching company focused on sustainable growth and leadership development for high level service-based businesses. 6 Under-The-Radar Software Tools Project Management Notion Taskade Trello Asana Basecamp AI Notetaker Zoom AI Companion Fireflies AI Fathom Otter AI Features in Your Existing Software Duet AI for Google Workspace Copilot for Microsoft Teams Passive Timekeeping Apps Clockify Toggl Chrometa WiseTime Memtime (formerly TimeBro) Expense Tracking Expensify Automated Client Communications: Hona Case Status ----- If these software tools aren't enough to give your productivity a boost, try listening to this playlist. ------ Our opening song is Two Cigarettes by Major Label Interest. Our closing song is In Your Head by Reveille.

Were the Beach Boys once on track to become America’s version of the Beatles? Surprisingly, maybe. Disney recently put out a less-than-stellar Beach Boys documentary, so Jared takes on the task of dishing on the true talent, grit, beauty, and tragedy of the group’s career. Next, We all have connections that carry the potential to be valuable in our professional lives, but if those connections are difficult to maintain, possibilities may slip away. How can attorneys deepen relationships and strengthen their business opportunities? Just like everything else—with AI, of course! Jared talks with Jody Glidden about new AI-fueled software that helps attorneys with front-office tech geared toward nurturing your network. And last, Jared hands over the Rump Roast to Real Housewives superfans Ally Kvidt and Lindsey Egan! As it turns out, Jody is a regular on Real Housewives of Miami (gasp!). So, now it’s their turn to dish on the talent, grit, beauty, and vapidity of the RHOMers. Plus, you’ll finally find out whether Jody and Lisa really stole that waffle iron. ------ Good, good, good, good vibrations (oom-bop-bop). This episode's playlist is all about the inventors of the California sound: The Beach Boys. ----- Our opening song is Two Cigarettes by Major Label Interest. Our closing song is Kokobongo by Alessandro Gugel.

Nowadays, all the cool kids are using customer relationship management (CRM) software, and you should too. It’s not new technology, but if you’ve missed the boat or need a refresher—Jared’s here to fill you in on CRM technology and what it can do for you. He explains different types of CRMs in detail to show you its potential for creating seamless intake experiences and optimizing your workflows. Speaking of CRMs, Jared welcomes Matt Spiegel of Lawmatics to learn about his story as a tech founder and his methods and means for solving problems for attorneys. Matt offers his perspectives on CRM functionality and its latest developments, and also offers hints at how AI will affect this tech in the future. Last, but not least, Bobby Orozco joins Jared for the Rump Roast to flex his rap knowledge, unpack the Drake/Kendrick Lamar feud, and talk about the best diss tracks in rap history. Matt Spiegel is the co-founder and CEO of Lawmatics, an attorney-client relationship management platform. Bobby Orozco is director of sales at Lawmatics. ----- Drake v. Kendrick is just the start. This week's playlist features some of the best rap diss tracks of all time. ----- Our opening song is Two Cigarettes by Major Label Interest. Our closing song is Grime by Ghost Beatz.

Getting in front of an audience to communicate on camera certainly doesn’t come naturally to all (most?) attorneys, but if you’re feeling embarrassed by your lackluster video presence, there are ways to overcome those on-camera nerves. Jared talks with Kerry Barrett about how she helps professionals sharpen media skills to increase their visibility and present confidence and credibility to their audience. In the Rump Roast, they play “Candid Camera”, where Jared asks Kerry questions on the history of all things video. What was the last truly silent film? What band played the first-ever music video on MTV? Listen in to find out if Kerry’s up to the trivia challenge. And, lastly, hating on Caitlin Clark is utterly ridiculous. Jared expounds upon the many reasons why WNBA players (including Caitlin’s own teammates) need to take advantage of the hype and bask in all that Caitlin Clark is bringing to women’s basketball. ----- Since Video Killed The Radio Star, here's a playlist featuring songs that had some of the best music videos. ----- Our opening song is Two Cigarettes by Major Label Interest. Our closing song is Just Like Me by Thruline.

Jared kicks it off by exploring the biggest players in productivity software you should be using, well, be more productive. But no productivity suite is perfect. So, get to know the strengths and weaknesses of each so you can make the right choice for you. Then, back in the day, lawyers often got their IT services from some independent techie who took care of stuff on an as-needed basis, but that sort of break/fix model is problematic if your tech strategy is only reactive instead of proactive. Jared talks with Michael Doherty about what it looks like for lawyers to engage IT services through a managed service provider (MSP). Michael walks attorneys through modern realities and ethics for technology use in their law firms and the potential for better outcomes when working with an MSP. Later on—the Rump Roast, of course! The guys play “Hard Choices”, where Jared poses difficult Boston-themed scenarios and Michael must educate the masses on what a true Bostonian would do. ----- Let's keep this Boston train going. Next stop: some of Boston's greatest musical hits. ----- Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Take a Ride With Me by The Revolution.

AI’s prime directive is to give you answers, buuuut… it might just be telling you what it thinks you want to hear—with no concern over providing actual verifiable facts. This issue (and oodles of others) have initiated a trickle of case law/guidance/opinions/etc. in the legal AI scene, and you, dear lawyer, want to be on the right side of legal ethics on this one. Jared breaks down the latest developments on this topic to give you a better understanding of where things are headed. Next, some of us are, admittedly, BS-ing our way through all this AI stuff, but Josh Noffke really and truly uses AI as much as he possibly can in his law firm. Since the rest of us are still muddling through, Jared welcomes Josh to give attorneys tool recommendations and pointers on use-cases for AI in their law firms. Later, it turns out that Josh played as a walk-on for the University of Michigan’s football team, so the Rump Roast is dedicated to team trivia! The guys play “Michigan Man” to test both Josh’s knowledge and reputation as a former Wolverine. Serious stuff. ----- Ah, Michigan. The mitten shaped state that gave us Motown. ------ Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Renegade by The Revolution. Mentioned in This Episode: Notion Scribe Loom Videos Rocket Typist TextExpander

Bored with your run-of-the-mill marketing campaigns? Maybe it’s time for you to make a musical! Jared brings on Jacob Sanders to learn all about the recent release of NinjaCat’s Big Data Day – a corporate musical. They talk about the history of these sorts of marketing ventures and their uniquely fun and tactical advantages. They also dig into how super effective use of your data will help you run a better, more profitable business. Next, the Rump Roast! In a new trivia game called “Large Fathers”, Jacob must answer questions about big daddies of historical pop culture. ----- Also in this episode—Jared, in general, hates musicals (Sorry, Jacob). No spoilers here, but a very select few did make Jared’s remarkably minuscule shortlist. ----- Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Sepulveda by Midnight Daydream.

So much of our communications and societal existence is housed online, so e-discovery is the major way we gather evidence. Jared talks with Cat Casey about the AI spectrum within the e-discovery world, explaining the many ways varying elements of machine learning and AI have created more powerful tools for attorneys. They also discuss the promising future of AI in e-discovery and the legal profession. This time on the Rump Roast, Jared quizzes Cat on cat-themed song lyrics. Is Cat an expert on feline musical appearances? We shall see. Everybody keeps asking about AI, so Jared’s delivering! There are quite a few budding AI softwares tailor-made for attorneys, so what tools are worth your attention? Jared reminds everyone—lots of the things you already use have had AI baked in for a long time, so use it. Security is important, folks, so picking vetted technology over an unknown/free tool could definitely keep it from coming back to bite you in your ethically questionable ass. Cat Casey is Chief Growth Officer at Reveal Brainspace, helping lead innovation and direction for their legal technology solutions. ----- Since you're listening to Cat on the mic this episode, the logical next step is to listen to this cat inspired playlist. ------ Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Banksy by Lunareh. Links Mentioned: Women in eDiscovery Operation Safe Space SPLASH Pledge Law Rocks!

Sometimes, legal tech is the perfect solution for the needs of your law firm, but sometimes, lawyers need to look outside the legal tech world at other technologies that can serve their legal practice better. Emily Gordon has always been a tech-forward attorney, and she’s got tons of recommendations for non-legaltech tech tools that have become the most effective solutions for her law firm. Then, Emily sticks around for the Rump Roast! The “Amara” in Emily’s firm, Amara Law, is actually her middle name, so Jared devised a middle-name trivia game: “Stuck in the Middle With You”. And, dear listener, get ready for a hot take from Jared: SNL sucks, and… you know what? Maybe it always has. But, there’s something better out there—”I Think You Should Leave” on Netflix is worth watching again and again. Have fun! _____ Since we talked about middle names coming first, I’ve put together what is, perhaps, our most middling playlist ever. Links Mentioned: Front Twilio PandaDoc Stripe

Adjusting to the new and persistent presence of AI in the legal world isn’t easy, but it is necessary. Jared welcomes brothers Justin and Luc Cary, an attorney and software engineer, respectively, to unpack the current state of AI in business and legal uses. They discuss current safety issues, emerging guardrails, best practices for research, AI in legal tech software, and more. Later on in the Rump Roast, the guys play “Brother Up”, where Justin and Luc must identify famous brothers in history and pop culture. And, should you be entering confidential information into generative AI tools? Well, there are layers, folks, but in the current AI environment, lawyers should never assume their data is secure. That being said, Jared doesn’t want to throw a wet blanket on the AI revolution, he just wants you to know the three simple things that will enable you to use these tools safely and ethically. Justin Cary is an attorney at Drummond Woodsum. Luc Cary is associate director of machine learning at Invitae. _______________________________________________________ Since we have the Cary brothers with us this week, here's a playlist all about siblings! _______________________________________________________ Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Promised Land by Brian Brown

Backsliders are the worst, and if you’re making your employees come into the office after years of successful remote work, then, well… you’re the worst. Jared weighs in on the remote/in-office work debate to help you take a hard look at why you’re doing what you’re doing—and whether your reasoning is utter bullshit. Next, Jared welcomes first-time guest Rob Joyner to talk about how technology adoption is the means to the end of future-proofing your law firm. To some lawyers, new tech may feel like the great unknown, but failing to learn and implement it will make you fall behind your competitors. Jared and Rob talk about the latest in AI and other essential legal tech and the best ways for law firms to stay current. In the Rump Roast, Jared forgoes his typical torturous games, because Rob has a legit cool hobby to talk about. You can learn more about it at paintedjoyner.com. Rob Joyner is Senior Vice President of Business Development at Centerbase. ----- Since we talk about artwork - a departure for us, for sure - here are some songs related to art. ----- Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Spoken Word by Renderings.

Why is it that law firms are a frequent target for data breaches? Make no mistake, attorneys, you’ve got a lot of sensitive, valuable data that a threat actor would love to get their hands on. If your cybersecurity isn’t effective, you’re opening yourself up to a whole lot of ethical and legal issues. Jared chats with David Aaron about preventative measures lawyers should employ, what to do if you suffer a breach, and current cybersecurity trends. Later on in the Rump Roast, the guys play “Doubling Up”––where Jared quizzes David on trivia devoted to people blessed with a first-name first name and first-name last name. You get it, right? And, is anything more annoying than email? Not in Jared’s estimation. He shares his thoughts (read: rants) on the vexing email follow-ups people tend to send with irritating regularity. ----- This episode, we covered some annoying email tactics, so we made the playlist all about the proper messaging. ----- Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Christmas Time is Lambs Farm by Sam Barsh.

If your firm is experiencing operational challenges you just can’t seem to overcome, you might be in need of some C-suite help. Lawyers don’t necessarily want to take on the business responsibilities of running a practice, and there are many flexible ways to get the business guidance you need. Jared talks with Seth Tuman of 2GO Advisory Group about how either fractional or full-time C-suite professionals can help attorneys take their law firms to the next level. Later, you’re in for a holiday treat on the Rump Roast with the return of Correia Family Stories! Jared’s mom and brother, Pat, share some of their favorite holiday memories. Was it Jared or his sister who was responsible for the pine needle in Pat’s eye? And, who knew Scattergories could be so delightfully awkward? Listen in for more. And, last but not least, if you’ve always wanted to elevate your holiday entertainment aficionado status, Jared has all the little-known titles you need to watch to become a truly well-versed movie snob. ----- The holiday's are a good time to connect with your roots, so in honor of my mother and brother joining, here's a playlist of Portuguese music to honor my family's native land. ----- Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Christmas Time is Coming by Moments.

Searching for state court data used to be a huge pain in the ass, but data analytics has almost entirely fixed it, giving attorneys searchable databases in just about every state. What else has data analytics done for the profession? Plenty. Jared talks with Nicole Clark about how the aggregation of legal data has given us a much deeper understanding of courts, judges, and law firms—and even gives lawyers an edge in the courtroom. Trigger warning: they also give a nod to AI and its major contributions to legal data analytics. It’s almost Christmas, but let’s take a look back at Thanksgiving! Jared and Nicole play “Overrated, Underrated, Properly Rated—Thanksgiving Edition” to determine whether beloved Thanksgiving traditions like stuffing, football, and uncomfortable political conversations are given their due. Though controversial in its day, Paul Simon’s “Graceland” is a perfect album. After a run of personal and professional disappointments, Simon hit upon some pretty fortuitous inspiration that led to this pristine collection of musical craftsmanship. Jared unpacks the surprising and varied Americana-meets-world-music vibe of “Graceland”, the most popular album of Simon’s career. Nicole Clark is co-founder and CEO at Trellis Research Inc. ----- We celebrate Paul Simon's perfect album 'Graceland', with our episode + this playlist. ----- Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Life of the Party by Dr. Delight.

As lawyers, you constantly assess the risks of your clients, whether in their business practices, court cases, personal relationships, or a multitude of other things. So, managing risk for your clients is what you do, but when was the last time you took a hard look at your own liabilities? Jared welcomes Mark Bassingthwaighte of ALPS Insurance to chat about common risks in modern legal practice. Mark’s approachable take on insurance could help just about anybody understand what they need for their law firm, and he and Jared also talk through current ethics considerations around AI and cybersecurity. Then, in the Rump Roast, Jared tests Mark’s expertise on authentic blunders in a game called “Historic Mistakes.” Did the Titanic sink because of a sleepy watchman? Was Archduke Franz Ferdinand’s assassination the result of a forgotten fancy hat? Listen in to find out. And, lastly, everybody’s rolling out their AI tools/extras/whatever, and pricing for these things is truly all over the place. Jared ponders this issue—as a lawyer, you need to be able to keep up with the other guy, but how much should all this cost you? Mark Bassingthwaighte has been a Risk Manager with ALPS, the nation’s largest direct writer of lawyers’ malpractice insurance, since 1998. ----- Since we talked about mistakes - those lawyers make + historical ones, have a listen to our playlist featuring songs about fucking up. ----- Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Night Whispers by Dr. Delight.

Whether there’s a generational divide, unhelpful technology, a lack of emotional intelligence, or, really, a whole bunch of other issues—communication is hard. And, when communication breaks down, your business just doesn’t operate like it should. Is there any way to bridge all these gaps and interact effectively in your workplace? Jared talks with Rachael Bosch about her strategies for helping both individuals and teams understand each other better and overcome challenges in their professional lives. In the Rump Roast, Jared and Rachael play “A Rose By Any Other Name”—a game entirely focused on… deodorant! Jared tries to stump Rachael with a variety of real and made-up slogans. And, speaking of deodorant, Jared’s monologue took a deep, unpleasant dive into what is apparently acceptable on network TV commercials these days. It’s pretty revolting. Has Jared gone too far this time? Probably. Rachael Bosch is the founder of Fringe PD. ----- We talked about how to cover up for your stankiness, and so we put together some songs about smells. ----- Our opening track is Two Cigarettes by Major Label Interest. Our closing track is I'm Drowning by Dr. Delight.

Document management is a must in legal, and Microsoft 365 has plenty of ways to organize and process your documents for you. So, what do you need to know about it? Jared welcomes Keith Vallely to talk through the uses of SharePoint, OneDrive, and other Microsoft features to help attorneys understand the nuances of Microsoft’s methods for document management. The Rump Roast digs deep into tricky Star Wars trivia in a game Jared likes to call “Star Tours.” Do you know what language is written on Darth Vader’s chest plate? Does Keith know? Listen in to find out. And, Jared taps into his unapologetically nerdy side to analyze the current sci-fi offerings in the multiverse and beyond. So, if you’re in need of some excellent escapism, Jared has plenty of recommendations for the sci-fi movies and shows you should watch. Keith Vallely is Vice President and Senior Consultant at Epona USA. ----- Since we talked about a lot of different sci-fi IP - including Star Wars - let's enjoy a list of the best sci-fi movie needle drops of all-time. ----- Our opening track is Two Cigarettes by Major Label Interest. Our closing track is Tenderness of You by Cast of Characters.