Gordon was a corporate lawyer in Toronto, closing deals in boardrooms with the occasional champagne in hand. After making a niche tool that automates legal transaction processes, he created another product that anyone with a PDF can use, turning every “I know I’ve read that somewhere" into “I know exactly where that is.” That product is Eno.

Most AI tools answer your questions with generated summaries and vague citations, but Eno is what Gordon calls “evidence-based AI.” It’s a zero-retention desktop app that surfaces the actual document snippets on screen so you can find what you’re looking for in your source material at 10x speed. Think of it as a “fuzzy Control+F.” Because attorneys can’t afford to communicate paraphrases of the law to clients, this distinction is critical. Gordon’s goal is to get another business acquired and make Eno big enough to be in a crossword puzzle!

Watch the episode to get in-depth insight about Gordon, why locally run apps are becoming legal tech’s latest trend, and how he’s deciding to run Eno in comparison to Closing Folders.

More on Gordon Cassie:

• Gordon Cassie on LinkedIn

• Gordon Cassie on X

• Eno Website

• Eno on LinkedIn

“And so.. we wanted to essentially be able to provide this same level of capability that people would’ve paid thousands and thousands of dollars for a forensic analyst.” - Dory Lord

Anyone who has been divorced understands how strenuous it is to sift through years of financial documents, as if the divorce itself wasn’t mentally taxing (pun intended). It’s the last thing people want to deal with, and now it’s a process that lawyers and forensic accountants can expedite! We’re highlighting CounselPro co-founders Ian O’Brien (CEO) and Dory Lord (CRO) in this episode.

After experiencing this exact issue himself, Ian looked for a simpler way to manage his financial statements but couldn’t find anything satisfactory. Through market research, he discovered a need to automate financial evaluation for family law and bankruptcy attorneys. With Dory’s marketing operations and legal tech background, and Ian’s engineering and marketing expertise, they joined forces to create CounselPro.

In Ian’s words, “CounselPro is so easy, even a lawyer can use it.” With its drag, drop, done interface, CounselPro’s platform ingests thousands of pages of financial documents. It'll organize PDFs, categorize every transaction, flag missing statement ranges, and allow attorneys to search and filter by merchant, date, account, and more. The output can withstand scrutiny, making it court-ready by design.

This episode covers Ian’s and Dory’s path to entrepreneurship, why they’re targeting solo practitioners and small law firms, the industries they want to reach next, and their vision for CounselPro’s future.

More about Ian and Dory:

• Ian O’Brien on LinkedIn

• Dory Lord on LinkedIn

• CounselPro Website

• CounselPro on LinkedIn

Her journey began in Big Law at Sidley Austin, where she worked on pro bono cases for domestic violence survivors as a litigator. Her time there sparked the idea for a document automation platform, which was later known as Documate. So, despite the risks of leaving a secure full-time job, she bet on herself and quit to pursue entrepreneurship.

Not long after launching Documate, she realized early on that the legal tech industry was headed toward an AI-centered direction. With the help of her team, investors, and a CTO with deep AI knowledge, Documate was rebranded to Gavel. The rebrand was a necessary move to encompass the added AI-native products that complement the original document automation service. And for those of you who know Dorna, you may have even participated in suggesting a name for the rebrand! All the decisions she’s made as a founder have paid off, and Gavel is now part of the legal AI platform, Relativity.

Hear from Dorna herself about how understanding her customers has helped her business grow, the benefits of staying agile, the hardest decisions she’s had to make as a founder, and her thoughts on the recent acquisition.

More about Dorna:

• Dorna on LinkedIn

• Dorna on Substack

• Gavel Website

• Gavel on LinkedIn

• Gavel Acquisition Announcement

Hey readers, Hana and Nick here! We understand how busy a working professional’s life can be. Calendars stacked with meetings that could have been emails, looming deadlines, booking back-to-back flights to attend conferences, and don’t even get us started on fixing technical issues. Things add up, and the time to hear your favorite legal technology podcast dwindles. But you’re in luck! Here’s a recap of all the episodes since the relaunch.

Episode 132 announces the relaunch of the LegalTechLIVE podcast! Founder Nick Rishwain introduces his new co-host, Hana Zumout, a digital marketer with 7 years of experience in the legal technology space and the person behind the podcast’s rebrand.

Episode 133 highlights our first guest since LegalTechLIVE’s return, Nathan Walter, CEO of Briefpoint. His career as a litigator exposed him to how opposing counsel used discovery as “lawfare,” which inspired him to build Briefpoint. Nathan’s goal with Briefpoint is to “eliminate discovery off the face of the earth” by automating the discovery document drafting process. Briefpoint saves litigators’ time and brings justice to their clients.

Lindsay Kim Chung, CEO of TensorCase, is our guest in Episode 134. Most legal technology services cater to attorneys, but we rarely hear about tools for other legal professionals, like investigators. Before she became an entrepreneur, Lindsay was a lawyer and corporate investigator. She found herself facetiously commiserating with her colleagues, wishing there was an efficient way to manage evidence and draft reports. So, Lindsay built TensorCase, a “thinking partner” for investigators.

In Episode 135, Director of Policy at The Digital Chamber, Jonathan Schmalfeld, shared his experience in blockchain advocacy. He was an attorney specializing in trade secret litigation. As a crypto enthusiast himself, he entered the digital asset space professionally while working on NFT trademark and consumer protection cases. Jonathan now lobbies for policies, like the GENIUS Act, to Congress to make digital assets more accessible to the public.

Mathew Kerbis, a.k.a “The Subscription Attorney,” podcast aficionado, and Practi founder, talks to Nick and Hana about how AI is breaking the billable hour on Episode 136. Because tools like Harvey and Legora shorten the time it takes to complete legal work, the billable hour model isn’t ethically or financially sensible. Wanting to drive systemic change, Mathew built Practi, an easy-to-build subscription-based billing system for solo practice and small law firms.

Episode 137 features Chris Ford, co-founder and CXO of Legaltech Hub. His marketing expertise complements the entrepreneurial mind of CEO Nicole (Nikki) Shaver, who also happens to be his wife. We LOVE love in legal tech! LegalTech Hub has transformed from a COVID side project into a functioning media and insights business with 30+ team members, 3,000+ listed legal technology tools, and dozens of events led by Chris. He also shares priceless marketing advice founders should hear.

It’s not often we cover legal operations on the show, but we believe in highlighting all legal professionals. Episode 138 highlights Cheyenne Gabourel-Moseley, the Legal Operations Director at Rasa. After spending 21 years at LegalZoom, starting in customer service and finishing as director of an entire division, she left to join Rasa. Rasa helps people expunge their criminal records and provide freedom as a service. Cheyenne details the day-in-the-life of a legal operations professional.

Erich Dylus’ unique background as a programmer and solo-practice attorney helped him create CamoText. In Episode 139, he shares the obvious and latent privacy risks that AI poses, and how attorneys could inadvertently breach the attorney-client privilege. CamoText anonymizes personally identifiable information (PII), such as names, locations, and financial account details, in documents. Attorneys can then run the documents in their AI tool of choice.

As a solo-practice lawyer, Erich underwent the mind-numbingly mundane task of manually removing private data in his legal work. He noticed that the labor of wiping metadata and copy-pasting clean text into AI chats was the kind of friction that causes lawyers to ignore privacy steps. Erich wanted a way to expedite and preserve confidentiality. Luckily for him, he’s also a programmer.

The Python script he wrote became CamoText, a fully offline document app that detects and replaces PII (personally identifiable information) with placeholders. Names, email addresses, UUIDs, locations, finances, and other private information are camouflaged. And the best part? You can paste the sanitized version from CamoText into your AI tool of choice, with human review, of course.

Tune in to learn about less obvious privacy vectors, how CamoText also serves non-legal industries, and why offline apps offer security by simplicity.

More about Erich:

• Erich Dylus on LinkedIn

• CamoText Website

• CamoText on LinkedIn

• Varia Law Website

• Varia Law on LinkedIn

Cheyenne spent 21 years at LegalZoom before joining Rasa. She started in customer service roles and worked her way up to director of an entire division. Within that time, she saw legal tech scale from Manila folders and FileNet to Salesforce and AI tools. After meeting her boss and the founder of Rasa, Noella Sudbury, she decided to leave her corporate job for a mission she couldn’t refuse.

Rasa’s goal is to help people expunge their criminal records, which is different from LegalZoom’s high-volume business formation. As Legal Operations Director, she navigates multiple counties across multiple states whose courts have different timelines and processes (that’s if they have a process). Her role brings about additional nuances compared to business operations, as people’s freedom is the service Rasa offers. What remains the same is how Cheyenne applies the same operational skills she learned in corporate to a public benefit corporation setting.

Get to know Cheyenne, understand legal operations and Rasa’s mission on a deeper level, and discover how she creates repeatable processes in this episode.

More about Cheyenne Moseley:

• Cheyenne Moseley on LinkedIn

• Rasa Website

• Rasa on LinkedIn

Chris entered the legal industry right out of college, selling document services to law firms in America. As his career progressed, he found himself in marketing roles and realized this was what he was meant to pursue. He landed a role at LexisNexis in Australia and met Nikki several years later.

What started as a COVID side project became the legal tech industry’s first full-scale solutions, media, advisory, and events company. While Nikki was working at Paul Hastings, she was frustrated by the lack of a consolidated, objectively truthful source of legal tech tools. So, they made one. Now, Legaltech Hub is a company of 30+ team members, 3,000+ tools listed, dozens of global events led by Chris, and a project involving lots of blood, sweat, and tears.

Watch or listen to Chris’ in-depth marketing advice, endearing sentiments toward Nikki, and future goals for Legaltech Hub.

More about Chris Ford:

• Chris Ford on LinkedIn

• Chris Ford Legaltech Hub Email

• Legaltech Hub Website

• Legaltech Hub on LinkedIn

With tools like Harvey and Paxton shortening the time it takes to execute legal work, billing by the hour doesn’t make sense, financially or ethically. The consequence is a decline in associates at law firms and the loss of priceless time with loved ones. Mathew saw an opportunity to increase attorneys’ revenue, close the access-to-justice gap, and drive systemic change.

Practi is not an AI service, but a company that exists because of AI. It provides an easy-to-build subscription-based billing infrastructure to solo and small law firms. The set-up alone takes less than 10 minutes, and it’s free! The billable-hour model doesn’t suit an AI-forward legal industry, but the subscription model fits right in.

Hear Mathew’s arguments for a subscription-based billing system, his founder story, and how he created a marketing ecosystem in this “name-drop” episode.

More on Mathew Kerbis:

• Mathew Kerbis on LinkedIn

• Subscription Attorney Website

• Subscription Attorney LinkedIn

• Practi Website

• Practi LinkedIn

• Legal AI Live Substack

• Legal AI Live LinkedIn

• Law Subscribed Substack

• Law Subscribed LinkedIn

“The only people who really use crypto for crime are… people who don’t realize it can be traced back to them…, or people that don’t care.”

Now that we have your attention, you can probably guess what this episode is all about (no, it’s not crime). Cryptocurrency and the blockchain industry have existed for decades, and you might have bought some yourself. We’ve brought you insider knowledge of how digital assets are handled at the federal level. Meet Jonathan Schmalfeld, Director of Policy at The Digital Chamber.

Jonathan spent a decade as a practicing attorney at law firms like Polsinelli and Husch Blackwell, specializing in trade secret litigation. As he was buying and selling Bitcoin and Ethereum (regretably, too soon), he broke into the digital asset space while working on trademark and consumer protection cases involving NFTs. What was a personal interest turned into his full-time job. Today, Jonathan works for The Digital Chamber, the United States oldest and largest blockchain advocacy organization. He works with government officials to sign bills into law (such as the GENIUS Act) and to make digital assets more accessible to the public. For Jonathan, there has never been a better time to be in the room where financial regulations are made.

Watch or listen to the episode to learn about changes in the digital asset industry, common misconceptions, blockchain advantages for Americans, and how Jonathan informs Congress about digital assets.

More about Jonathan Schmalfeld:

• Jonathan Schmalfeld on LinkedIn

• The Digital Chamber Website

• The Digital Chamber on LinkedIn

During her corporate investigator days, Lindsay and her colleagues would facetiously commiserate over managing mountains of evidence and having the time to draft reports. At times, she found herself needing that one email, interview, or other piece of evidence that actually mattered, and wondered why there wasn’t a better way to do the job she loved. After coming across research on LinkedIn noting that founders of high-growth unicorns are 45-years-old on average, she courageously pursued the entrepreneurial grind that always lingered in the background.

TensorCase is an AI-powered platform supporting investigators with evidence management, data analysis, and report drafting. With built-in investigator-specific terminology and context, TensorCase is essentially “Lindsay’s brain,” a silly yet true way of saying that it’s a tool for investigators, made by an investigator.

Find out more about Lindsay’s career pivot, the problems TensorCase solves, and the highs and lows of founding a startup in this episode.

More about Lindsay Kim Chung:

• Lindsay Kim Chung on LinkedIn

• TensorCase Website

• TensorCase on LinkedIn

Discovery is the pre-trial phase of a lawsuit in which parties exchange information about the witnesses and evidence to be presented in court. At times, discovery can turn into a long-standing battle. As a litigator, Nathan was so frustrated with opposing counsel weaponizing discovery to bleed clients dry, a.k.a. “lawfare,” that he built Briefpoint to automate the discovery document drafting process, save fellow litigators time, and bring justice to clients.

In the beginning, Nathan simultaneously built Briefpoint and learned the business by selling technology to attorneys at Ironclad. He studied venture capital acronyms for investor meetings, cold-called attorneys from the California Bar website to establish his consumer base, and made vaporware programs for market research. He and his top salesman managed to close $20,000 deals hours before payroll was due to keep Briefpoint’s lights on! Now, Briefpoint serves 1,500+ law firms nationwide. Nathan’s journey is a survival story filled with quick wit, slight sarcasm, and insightful entrepreneurial advice.

Watch the rest of the episode to deep dive into the four real moats of legal tech, how generic AI companies like Anthropic compete with their own legal tech consumers, and lessons learned from starting a business.

More about Nathan Walter:

• Nathan Walter on LinkedIn

• Briefpoint Website

• Briefpoint on LinkedIn

After a five-year hiatus, the LegalTechLIVE podcast is BACK! From company acquisitions and emerging players to the rise of AI integration, the changes in legal technology are unfolding rapidly. We’re here for these conversations and believe in sharing the wealth of knowledge.

It might seem random that Nick asked me to co-host LegalTechLIVE, but if you didn’t listen to Episode 132, here’s a recap:

Outside of being cousins, we worked together at Experts.com. We also launched a partnership with Experts.com during my time at WordRake. With my background in Digital Audience Strategy, I have roughly 7 years of marketing experience in legal tech. Being a young professional in the industry without a law school education adds a fresh perspective to the podcast. The questions I’ll ask startup founders and legal tech professionals will differ from Nick’s, which we hope will set us apart from our beloved legal tech podcast comrades. Whether we’re new to legal tech or have been in the game for a while, there’s a lot we don’t know. Reviving and rebranding the podcast with an energetic, friendly, and inquisitive feel helps us all learn from the people shaping it.

Speaking of rebranding, you may have noticed some changes. Given my addition to the podcast and minimal design changes sine 2015, a makeover was needed. Nick and I wanted to incorporate a masculine and feminine aura through the color scheme while maintaining a technology-focused aesthetic, with many hues of blue and contrasting colors to grab your attention. While the design has changed, the tone remains the same: casual, cheerful, and curious. The legal industry is stereotypically stoic and boring, and it deserves some levity with lighthearted, relevant conversations!

Stay tuned for our upcoming episodes, and welcome back to LegalTechLIVE!

Watch, listen, and subscribe to LegalTechLIVE and stay tuned for our next episode!

Connect with your hosts:

• Nick Rishwain on LinkedIn

• Nick Rishwain on X

• Hana Zumout on LinkedIn

Over the course of his career, Allen has built a reputation for creating innovative #legalservices products as well as developing highly effective law firm business and marketing strategies. Allen is a valued speaker on the topics of law marketing, legal services product development, and future of law issues. He has provided consulting and marketing services for companies such as McKinsey & Co., Coleman Research Group, LexisNexis, and Littler.

Before starting The Singular Law Group under the Arizona alternative business structure for #lawfirms, Allen founded law innovation agency ONE400 and was the Director of Attorney Services at LegalZoom. While there, his work contributed to a substantial portion of overall revenue at the company and helped LegalZoom move from a provider of "do-it-yourself" legal services to a comprehensive legal solutions provider, incorporating attorney-fulfilled work across all U.S. jurisdictions. Additionally, this was a special evening event on #VeteransDay and Allen is a United States Army veteran.

We were honored to have him join to tell us about the Singular Law Group on such a special day. For those considering building a law firm in Arizona, that allows for non-lawyer ownership, you're going to want to catch this replay. Allen doesn't only give us the vision of Singular Law Group, he also lays out the exact steps he went through to apply to the Arizona bar and the efforts it took to be approved to offer legal services under the ABS model. Thanks for spending time with us this season... we'll be back in the future!

More about Allen Rodriguez & Singular Law Group:

Allen Rodriguez on Twitter: https://twitter.com/allen_rodriguez. Allen Rodriguez on LinkedIn: https://www.linkedin.com/in/allenrodr... The Singular Law Group: https://singular.law/. ONE400: https://one400.com/.

The Effectiveness Project is an international working group of legal professionals, with support from LTC4, collaborating to establish best practices and baseline skills for creating effective legal documents. They are focusing, at present, on what is called Document Competency.

The first release from The Effectiveness Project, is the Document Competency Best Practices Guide. This guide is free and can be downloaded right now. See the link below. The Best Practices Guide was created with the understanding that the legal document-creation process is highly individualized. As such, The Effectiveness Project sought to provide guidance that is specific, yet flexible. To meet that goal, the Best Practices Guide is divided into drafting stages so it can be used as a modular part of a workflow.

Two participants in the collaboration are friends, and former guests, of LegalTechLIVE. They joined us to describe the goals and mission of The Effectiveness Project.

Ivy Grey is the Vice President of Strategy and Business Development at Wordrake. Ivy has been the driving force behind the effort to improve efficiency and effectiveness of document creation through The Effectiveness Project.

Chris Cangero is the Chief Executive Officer of DocStyle, LLC and another of the leading voices behind push for better document creation via The Effectiveness Project.

Take a listen and download the Best Practices Guide. Connect with our guests and get involved!

Here is how it works: 1) Tell us about your dispute. We will invite the other side to resolve it and assign a qualified and friendly Arbitrator. 2) You will upload evidence and have a live phone or video hearing where the Arbitrator will hear both sides of the story. 3) Your Arbitrator will issue a decision within 8 days of your hearing. This decision is legally binding and enforceable.

Stephen Kane is a former practicing lawyer who has been working on this #accesstojustice solution since before 2016. As an attorney, he saw how unfair the legal system can be for both individuals and businesses. As a result, he built a platform where parties can be heard, regardless of who they are. Learn more about this online dispute resolution ( #ODR ) platform for binding arbitrations. In the discussion, we cover a variety of issues, from fundraising, to founding, and beyond. Sit down and watch and enjoy another discussion with a #legaltech founder.

More about Stephen Kane & FairClaims: Stephen Kane on Twitter: https://twitter.com/stephenlkane. Stephen Kane on LinkedIn: https://www.linkedin.com/in/stephenlkane. FairClaims on Twitter: https://twitter.com/Fair_Claims. FairClaims website: https://www.fairclaims.com/.

Karen Renee owns Milwaukee Court Reporters and actively provides court reporting services. Graduated 2008 cum laude from Alfred State College, New York, associates degree. She was awarded Innovator of the Year from the State Bar of Wisconsin, Innovation Use of Technology from the National Court Reporters Association, and Bright New Idea award from the Governor's Business Plan Contest.

Karen is a lifelong entrepreneur to say the least. In this episode, she tells a story about her introduction to the Uber app which inspired her idea to do the same thing with court reporting, as it has inspired a wide number of other technology innovations. There is a need for "gig" work and coordination. That's what eCourtReporters is offering to court reporters, legal videographers, and attorneys. A simple and effective way to coordinate freelance work. It is also helping court reporters, who are certified in more than one state, to accept work from all of the jurisdictions in which they're certified.

More about Karen Renee and eCourtReporters:

Karen Renee on LinkedIn: https://www.linkedin.com/in/karen-ren.... Karen Renee on Twitter: https://twitter.com/eCourtReporter. eCourtReporters on Twitter: https://twitter.com/eCourtReporters. eCourtReporters website: https://www.ecourtreporters.com/.

Talitha and Kristin were associates and a large regional firm before they made the move to a boutique law firm in Las Vegas. Near the time they made the change from "BigLaw" to the boutique firm, they also started the development of their #legaltech startup. Solution born from the problem they were facing now that they didn't have the massive number of associates and staff with which to turn to when things got busy, they began developing their own solution. A solution, meant to provide attorneys with greater control over their careers and help small and medium law firms find the expertise they required. Learn more about their journey and #startup life from two practicing attorneys and company founders!

More about Talitha, Kristin and LawClerk: Talitha Gray Kozlowski on LinkedIn: https://www.linkedin.com/in/talitha-g.... Talitha Gray Kozlowski on Twitter: https://twitter.com/TalithaBGray Kristin Tyler on LinkedIn: https://www.linkedin.com/in/kristin-t.... Kristin Tyler on Twitter: https://twitter.com/KristinTyler. LawClerk on Twitter: https://twitter.com/lawclerklegal. LawClerk website: https://www.lawclerk.legal/

More about Sophie Walker & Just-Transcription: Sophie Walker on LinkedIn: https://www.linkedin.com/in/sophie-wa.... Just Transcription on Twitter: https://twitter.com/SpeechToJustice. Just Transcription website: https://www.just-access.org/just-tran.... Just Access website: https://www.just-access.org/.

Here's a little background on the impressive pedigree of Jacqueline Schafer: Jacqueline began her career as a litigation associate at the New York law firm of Paul, Weiss, Rifkind, Wharton, & Garrison, and spent much of career as an Assistant Attorney General in the Washington and Alaska Attorney General's Offices, where she specialized in appellate practice and complex litigation.

Before joining the startup world and founding Clearbrief, Jacqueline also served as Senior Director, Program Counsel for the national child welfare nonprofit Casey Family Programs, negotiating agreements with courts across the country and managing litigation and amicus efforts in impact litigation. Jacqueline was recognized by VentureBeat as one of four semi-finalists for the 2020 Women in AI Rising Star award for founding ClearBrief, as well as for her Dec 2020 law review article describing how AI and natural language processing (NLP) will transform courts and government social services.

We won't tell you the story that changed how Jacqueline started to think about clarity and facts that led to the creation of Clearbrief... you'll want to catch that story in in the episode. Clearbrief allows you to know the record inside and out. The only tool that instantly finds and links to the best record documents (facts and evidence) to support each sentence in the brief, while you write! All while using #NLP.

More about Jacqueline Schafer & Clearbrief: Jacqueline Schafer on LinkedIn: https://www.linkedin.com/in/jackiesch.... Jacqueline Schafer on Twitter: https://twitter.com/jackiegschafer. Clearbrief on Twitter: https://twitter.com/Clearbriefai. Clearbrief website: https://clearbrief.com/. #startups