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In this Best of 2024 episode, we revisit our conversation with Scott and Digby Leigh, founders of AltFee—a legal tech startup tackling one of the industry’s biggest challenges: the billable hour.
Despite decades of debate, the billable hour still dominates legal billing. Enter AltFee. The app helps legal professionals scope, price, and manage projects using alternative fee arrangements (AFAs), offering clients more transparency and value.
Scott and Digby highlight why AFAs matter now more than ever: as AI reduces time spent on tasks, value-based pricing will become essential. AltFee provides a foundation for law firms to shift away from time-based billing, encouraging lawyers to focus on the actual value of their services—not just the clock. From scoping projects to auditing fees, this conversation explores the future of legal pricing and how AFAs can reshape client relationships for the better.
If you’re curious about innovation in legal tech, or if you’re tired of the constraints of hourly billing, this episode is a must-listen.
Episode Credits
Editing and Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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What does it take to build a successful legal tech startup? In this Best of 2024 episode, we revisit our conversation with Zach Posner, co-founder of the LegalTech Fund, an investment fund focused on supporting innovative legal technology companies.
Zach’s unique perspective on legal tech investing is rooted in his broad experience, including building an education tech company acquired by McGraw Hill. During our conversation, he shares valuable insights into what makes startups thrive. From the importance of transparent investor updates to fostering frequent, meaningful customer interactions that guide product development. We also explore the LegalTech Fund’s investment focus: Tools leveraging contracting data for business insights Tech solutions expanding access to legal services Whether you’re an entrepreneur, an investor, or simply interested in the evolution of legal tech, this episode is full of practical advice and inspiring insights.
Episode Credits
Editing and Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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In one of the most popular episodes of 2024, John Grant talks about how legal teams can adopt Agile and Kanban project management methodologies to optimize workflows, correct bottlenecks and increase client satisfaction. John is a lawyer and the founder of The Agile Attorney consultancy.
As John explains, the traditional project management method is waterfall. A technique often used by technology companies, involving a sequential approach where each stage is dependent on the completion of the previous one.
But John is a proponent of the newer, Agile methodology, which emerged from the software development community. It is a flexible approach where tasks are broken down into small increments with minimal planning, and processes are iterative. Agile is one of John’s favorites because he believes it is well suited for legal work.
John also talks about the value of a Kanban board, a visual tool used to manage work at various stages of a process. It typically includes columns such as “To Do,” “Doing,” and “Done”.
So why is he so into project management methodologies? Because despite coming from a long line of lawyers, before he went to law school, he first worked in tech.
Episode CreditsEditing and Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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Conrad Everhard, founder of Flatiron Law Group discusses his career trajectory from Georgetown University to becoming a partner at Big Law firms Jones Day and Brian Cave. He explains why he left BigLaw to found Flatiron Law Group, to provide a more cost effective and efficient way to offer legal services to clients involved in mergers and acquisitions.
To do so, the firm leverages a multi-pronged model: flat fees, low overhead, general contract labor to assist with the more labor intensive parts of an M&A deal, and advanced technology, including the firm's own custom build Deal Driver software that provides the clients with data and other insight about the deals they are working on.
Conrad also talks about his work with Stanford’s Codex project, where he is helping develop an AI based negotiation simulator to train young lawyers in M&A deals. He highlights the importance of capturing the decision-making process of senior lawyers to effectively guide the AI model.
Key Discussion Points & Timestamps:
Transition from Big Law to Entrepreneurship: [0:40 - 13:03]
The Flatiron Model: [14:16 - 26:48]
Work with Codex and AI in Legal Training: [26:48 - 33:00]
Resources & Links:
Flatiron Law website: flatiron.legal
Episode Credits
Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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This episode features Stan Shepard, General Counsel of Atlassian, a leading provider of team productivity and collaboration software. Stan discusses his unique career journey from a finance journalist to the current GC of Atlassian. He shares valuable insights into how Atlassian's legal department leverages the company's productivity software products and AI for maximum efficiency.
Episode Highlights:
[00:00:09]: Introduction and Stan's background - Learn about Stan's journey from finance journalist to lawyer at Charles Schwab, and eventually to his current role at Atlassian.
[00:04:00]: Why Stan transitioned from journalism to law - Discover his motivations for pursuing a legal career, including the desire for greater impact and client interaction.
[00:07:00]: The growth of Atlassian's legal department - Hear how the legal team has expanded significantly alongside the company's rapid growth, particularly during the pandemic.
[00:12:39]: How Atlassian's legal team uses their own products - Stan explains how Atlassian's legal department utilizes Jira, Confluence, and other tools to streamline workflows and improve collaboration.
[00:14:10]: AI routing of legal requests - Discover how AI automates the process of routing incoming legal requests to the appropriate specialists.
[00:17:02]: Atlassian's new AI product, Rovo - Learn about Rovo's search, chat, and agent capabilities, designed to enhance teamwork and efficiency.
[00:23:31]: Advice for legal departments adopting AI - Stan provides practical guidance on how legal teams can effectively integrate AI into their workflows.
[00:24:29]: Responsible AI implementation - Stan emphasizes the importance of approaching AI adoption with a focus on ethical considerations and mitigating potential biases.
[00:28:16]: Atlassian's involvement with BSA | The Software Alliance - Learn about Atlassian's advocacy work in the global software industry and their efforts to shape responsible tech policy.
Key Takeaways:
Embrace continuous learning: Stan's career path underscores the importance of adaptability and a growth mindset. Leverage technology for efficiency: Atlassian's legal team exemplifies how technology can optimize legal workflows and improve collaboration. Adopt AI responsibly: Stan highlights the need for a thoughtful and ethical approach to AI implementation.Resources Mentioned:
Atlassian: www.atlassian.com Jira: Atlassian's project management software. Confluence: Atlassian's knowledge management software. Loom: Atlassian's asynchronous video messaging tool. Rovo: Atlassian's new AI product with search and chat functionality. Responsible Tech Review Template: A guide for responsible AI development. (Available on Atlassian's website) BSA | The Software Alliance: bsa.orgConnect with Stan Shepard:
LinkedIn: Stan Shepard
Episode CreditsEditing and Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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New Era ADR CEO Rich Lee makes a return appearance to Technically Legal to talk about the company’s cutting-edge platform revolutionizing dispute resolution. Rich first came on the podcast in 2021 right as the company launched. Rich discusses the company's mission to provide a faster, more efficient, and cost-effective alternative to traditional litigation and arbitration, the company’s growth and what he has learned from a few years in.
Key takeaways:
New Era ADR offers a unique platform for resolving disputes in under 100 days, significantly faster than traditional methods.
The platform leverages technology to streamline processes, reduce costs, and enhance accessibility for all parties involved.
New Era ADR boasts a diverse pool of experienced and qualified neutrals, ensuring fair and impartial resolutions.
The company's commitment to innovation is evident in its use of data and technology to drive efficiency and transparency.
Timestamps:
[00:00:00] Introduction and recap of New Era ADR
[00:01:30] Discussion of the platform's features and benefits
[00:05:00] How New Era ADR addresses common dispute resolution challenges
[00:10:00] The importance of social proof in legal innovation
[00:15:00] Attracting and recruiting qualified neutrals
[00:20:00] The neutral selection process
[00:25:00] Future developments and roadmap for New Era ADR
[00:30:00] The impact of New Era ADR on various stakeholders
Resources and Links:
New Era ADR website: https://www.neweraadr.com/
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This episode features Matthew Rasmussen, Founder and CEO of ModeOne, which is an app that provides targeted smart phone data discovery. Matt discusses his journey from a psych major waiting tables to landing a job in eDiscovery in its earliest days-- a job that ultimately helped him land jobs in BigLaw for multiple firms running their litigation technology departments. It was when he was working for O’Melveny & Meyers when he had his "light bulb moment" that led to the creation of ModeOne, a solution addressing the challenges of efficient data collection from mobile devices.
Matt explains how ModeOne works, its benefits over traditional digital forensic collection methods, and how it addresses concerns about evidentiary defensibility. He also highlights the various use cases for ModeOne beyond litigation, including internal investigations, HR matters, and compliance. The conversation delves into ModeOne's development, its unique approach compared to competitors, and its future roadmap, including internationalization and integrations with other platforms like Relativity.
Learn more about Matt.
Key Discussion Points:
[0:39] Matt's unconventional path to eDiscovery
[3:35] The "light bulb moment" that sparked the idea for Mode One
[9:02] How Mode One works and its advantages
[11:36] Addressing evidentiary concerns and gaining credibility
[19:19] Expanding use cases beyond litigation
[22:48] iOS and Android certification process
[23:31] Apps and data supported by Mode One
[25:18] Mode One's built-in review tool and Relativity integration
[28:04] Future roadmap and upcoming features
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Jason Heinze originally wanted to be an architect but got into disability law after taking over his father in law’s practice. To establish his client’s disability claims, he would have them manually enter daily notes into a pain journal, but he often had difficulty getting clients to consistently maintain the journals because they might forget and it was a completely manual process.
He thought to himself, there has to be an app for that, but when he looked, he found some that were close, but not exactly what he needed. So, he created his own and called it ClaimData. By using the app, disability claimants can now make pain journal entries via a web app and it will also remind them to enter it.
ClaimData uses a progressive web app model for efficiency and cost-effectiveness. ClaimData integrates with case management systems and plans to expand into personal injury and workers' compensation. The app aims to simplify the evidence-gathering process for attorneys, making it easier to prove disability cases.
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Amanda Tuminelli, Chief Legal Officer for the DeFI Education Fund, visits the podcast to discuss her role with the organization and its objectives. (What is DeFi? It is shorthand for Decentralized Finance and the backbone of DeFi is blockchain technology and smart contracts.)
The DeFi Education Fund is a nonpartisan research and advocacy group working to explain the benefits of DeFi, achieve regulatory clarity for the future of the global digital economy, and help realize the transformative potential of DeFi for everyone.
Amanda goes in depth into the DEF’s areas of focus:
Research and Advocacy
Policymaker Education
Messaging for Crypto Companies
Research about Blockchain Issues and Regulations
Providing “Legal Firepower” to Crypto Causes; and
DeFi Project Best Practices
Amanda also discusses how lawyers can pursue a career in crypto and why that wasn’t the case a few years ago. It’s not only an option now because the industry is more mature, but also because of the openness of those in the crypto world and their desire for passionate individuals to join them. To get a job in crypto law, Amanda emphasizes the importance of understanding the technology and finding projects of interest.
So how did Amanda get to the DEF? She started out as a securities and white collar crime lawyer, but a case came along that would change her career trajectory. She was working for Kobre and Kim, a law firm focused on disputes and investigations, when the firm was hired by a client accused of running an illegal crypto mining scheme. To get up to speed on the case and get her client out of jail, she had to dive deep into learning about blockchain technology and that is when she caught the bug. A few years later, a friend and former college friend contacted her about joining the legal team at the DeFI Education Fund and she took them up on it.
Episode CreditsEditing and Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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AffiniPay is historically a fintech company with a big presence in legal. Their flagship product is LawPay used by law firms to bill clients and accept payments. Dru joined the company in 2021 and right around that time, the company ventured beyond the world of payment software and acquired MyCase, which is law practice management software used by law firms to keep all case details and documents in a single location, keep track of tasks and streamline client communications.
Growing up, Dru wanted to be a lawyer because she comes from family of lawyers, including her father. She studied law at the University of Chicago, but after a couple of gigs with law firms, she figured out that maybe the law wasn’t for her.
So, she finished her MBA and went to work for Boston Consulting. After a few years as a consultant, she needed a break, and, being somewhat of a foodie, she went to work in the kitchens of some of New York's finest dining establishments.
She took lessons learned from the kitchen into her later work as a co-founder of a baby monitor start-up and ultimately roles as CEO of the property management company Grace Hill and now AffiniPay.
In this episode, Dru talks about:
Joining AffiniPay and its mission
The company’s acquisition of MyCase and expansion into practice management software
Affirm, AffiniPay’s Buy now, pay later product and its impact
The company’s AI plans and integration within the platform
Core responsibilities of a CEO and what has surprised her in her role as a CEO
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Episode CreditsEditing and Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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A conversation with Lucas Moskowitz, General Counsel for financial services company Robinhood. Launched in 2013, Robinhood’s stated mission is to "democratize finance for all" by making it easy for investors to start investing with a few bucks rather than having to be a high roller. Key to this effort is the fact that Robinhood offers commission-free trading and also provides access to cryptocurrencies.
The discussion covers various topics, including:
Robinhood’s Mission: Lucas explains Robinhood's mission to democratize finance by breaking down barriers to investing and making it accessible to everyone, regardless of their financial background.
Lucas’s Career Path: Lucas shares his unique career journey, transitioning from big law to the SEC, Capitol Hill, and eventually Robinhood. He emphasizes the importance of diverse experiences in shaping his perspective.
Regulation in the Financial Industry: Lucas advocates for a data-driven approach to regulation, striking a balance between investor protection and fostering innovation and access.
Crypto & Blockchain: The potential of crypto and blockchain technology is explored, with Lucas highlighting their role in making financial markets more efficient.
Education: The importance of educating investors about making sound investment decisions and also educating legal professionals about emerging technologies like blockchain and tokenization of assets.
Stay in the know:
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A conversation with Matthew Veale, a European Patent Attorney and UPC Representative at PatSnap, an app that provides users with a comprehensive and user-friendly platform to conduct patent searches. Matthew discusses his experiences from work as an attorney in private practice and a stint at the UK Patent Office before joining PatSnap.
Matthew will discuss:
The future of AI in patent searches: How PatSnap's new AI component is transforming years of knowledge into a 10-second search.
AI's capabilities in analyzing and classifying images: Why AI can outperform humans in these tasks.
The impact of AI on legal practice: Assisting attorneys in understanding patent data and improving client communication.
The role of AI in due diligence: Enhancing efficiency without replacing human expertise.
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This episode involves two people with very distinguished careers. Bridget M. McCormack who now heads the American Arbitration Association (AAA) and Colin Rule, the founder of ODR.com just acquired by The AAA.
Bridget has served in just about every role you can in the legal industry. She started her legal career in legal aid and as a public defender handling trials and appeals. She then moved to teaching law school, first at Yale and then Michigan.
After her stint as an educator, she decided she wanted to help foster even more change and won a seat on the Michigan Supreme Court where she ultimately ascended to the position of Chief Justice. Fast forward to 2023 and she took the helm of the AAA.
One of Bridget’s biggest initiatives at AAA is bringing tech into the arbitration process and that is where Colin Rule comes in. He founded an online dispute resolution (ODR) company, about 15 years ago that ultimately became ODR.com which the AAA just announced it was acquiring.
To say that Colin is an ODR OG is an understatement. He literally wrote the book on ODR way back in the early days of the internet. Ebay brought him on board in the early 2000s where he headed up the company’s ODR function.
In this episode Bridget and Colin discuss:
AAA's acquisition of odr.com: The strategic partnership between AAA and ODR.com to revolutionize dispute resolution.
AI's transformative role in dispute resolution: How AAA is using AI internally and through external tools to improve efficiency and accessibility.
The future of dispute resolution: A vision for a more accessible, efficient, and user-friendly system that leverages technology and data.
Episode CreditsEditing and Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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Dr. Heidi Gardner of the Harvard Business and Law Schools joins the podcast to talk about about latest book Smarter Collaboration and the importance of collaboration in legal teams and in all organizations generally.
Smarter Collaboration is Dr. Gardner’s second book and a follow up to Smart Collaboration: How Professionals and Their Firms Succeed by Breaking Down Silos. Both books are helpful to those in law because much of Dr. Gardner’s research is based on the many years she studied collaboration in professional service firms, including many law firms.
Why is collaboration across different disciplines and business units important? As Dr. Gardner explains, most importantly, it creates better client outcomes which improve revenues and profits. But collaboration doesn’t just help make clients happy and improve the bottom line, it also fosters diversity and reduces enterprise risk.
Dr. Gardner has cold hard data that supports her conclusions: Back in the 1970s, 60% of US patents were awarded to individual inventors. Nowadays, that numbers has reversed. The vast majority of patents are issued to teams and the more diverse the backgrounds of those teams, the more successful their innovation.
Episode CreditsEditing and Production: Grant Blackstock
Theme Music: Home Base (Instrumental Version) by TA2MI
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Medex Chief Forensic Officer Brandon Epstein joins the Technically Legal Podcast to discuss the purpose built forensic tool for use in legal proceedings. The company counts legal professionals, law enforcement and journalists as its customers.
Medex is used to examine digital video files to establish provenance, detect tampering and identify modifications. Users may also use Medex to identify the device type that created the video.
As Brandon explains, the type of hardware used to create a digital video file leaves its own fingerprint. By examining the bits and bytes of a video file, Medex can discern whether a video file was created by, say, an iPhone, an Android based device, or even whether it was altered by posting on social media.
Brandon got his start in law enforcement as a patrol officer and through that work, he became acutely aware of the importance of video evidence in helping to solve crimes. Fast forward a few years later and he met Medex’s CEO at a conference they hit it off and Brandon was asked to join Medex.
Learn more about Brandon.
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Litera’s Haley Altman visits the Technically Legal Podcast to discuss the company’s new software offering: Foundation Dragon–an app powered by artificial intelligence that helps legal professionals advise clients based on market insights drawn from their law firm’s existing data and prior deal points.
This is a repeat appearance for Haley. She was first on the podcast in 2018 to discuss the company she had recently launched called Doxly. Founded in 2016, Doxly is a cloud based app that helps automate processes involved in closing M&A deals. In 2019, Haley sold Doxly to Litera and she too joined Litera and currently serves as a strategic advisor to the company.
One of the initiatives in which Haley is heavily involved is the company's recent launch of an AI product called Foundation Dragon.
Foundation Dragon is an app that connects to a law firm’s document management systems and experience software and once connected, using GenAI, it compiles information from the software and enables lawyers to enter into contract negotiations from a position of strength.
For instance, using Foundation Dragon users can:
Learn what contractual positions opposing counsel starts with or has agreed to in the past
Provide industry standards for individual contract clauses; and
Enable users to find precedents across a law firm to figure out what terms colleagues are using
In addition to Foundation Dragon, Haley also shares insights for startups. Including the importance of understanding the implications of capital raises and the potential impact on future exits.
Learn more about Haley and if you're interested in learning more about Foundation Dragon go here.
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Attorney Chris Edgar talks about founding Filmtracts- a DIY platform indie film makers can use to create entertainment based contracts for their projects.
Chris’ career path started with a clerkship for a future U.S. Supreme Court justice and then long hours as a Big Law litigator. After a few years of legal battles in and out of the courtroom, he realized that maybe his current career path wasn’t for him.
That’s because the world of entertainment law and independent film production was calling him. In 2010, Chris threw out his own shingle and founded an entertainment law practice. A few years later he and a partner launched their own indie film production company.
When other indie filmmakers figured out he was an attorney, he was often peppered with legal questions, but most of the time, those asking could not afford his services as an attorney. That’s when he decided to launch Filmtracts. A self serve repository of film related contracts that users can tailor to fit the needs of their project–and depending on the subscription they buy, they can also get a few hours of legal consultation from Chris.
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Studies determined that at least one litigant does not have a lawyer in 75% of civil cases in the United States. The number is even higher when it comes to family law, domestic violence, housing, and small claims matters.
But organizations like Oregon’s Commons Law Center are doing something about it. On this episode, Kamron Graham, the Law Center’s Executive Director, talks about the not for profit law firm’s efforts to provide affordable legal assistance to people that make too much to qualify for legal aid, but don’t make enough to hire a lawyer.
The Commons Law Center helps out people facing evictions, have family law issues or need help with wills and estate planning.
Kamron initially planned to pursue a career in finance but pretty quickly figured out that her empathy and concern for others probably might not jibe with a Wall Street career. After returning to Oregon after college in the Northeast, Kamron started her career working in group homes, homeless shelters and served a stint with the United Way.
These experiences made clear to her that a professional degree might help her have a greater impact on people's lives and give her even more of an opportunity to use her education to help others. So, in her 30s she decided to go to law school.
After law school continued her career helping the underserved, including work for Legal Aid Services of Oregon and work as a public defender.
Eventually she landed at the Commons Law Center, starting as a tenant defense attorney and ascending to the role of executive director.
The business model of the Commons Law Center is not free legal work, but charging a sliding scale fee based on a client's income. Currently 70% of the firm's budget comes from fees. The firm is working to become 100% self-sufficient, but in the meantime to fill the gap, the firm leverages tech to streamline their processes and keep costs down. It also relies on donors, foundations, and grants.
** Thanks to former Technically Legal Guest John Grant for making this episode happen and connecting us to Kamron.
Learn more about Kamron.
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Zach Posner discusses the LegalTech Fund, an investment fund he helped start that focuses on legal tech businesses and offers insight on what it takes to build a successful start up.
The LegalTech Fund has a solid track record and, if you have listened to a few episodes of this podcast, you’ve probably heard from founders of companies in which the Fund has invested–including Scott Stevenson from Spellbook, Otto Hansen at Term Scout, Tom Dreyfus at Josef, and also Zach’s colleague at the Fund, Mike Suchsland.
Zach brings a unique blend of experience and insight to legal technology investing. Among other things, prior to starting the LegalTech Fund, he helped build an education tech company that was ultimately acquired by McGraw Hill.
The LegalTech Fund has a couple of main areas of investing interest: Companies building tech that harnesses information from contracting processes and companies that are working to make legal services available to more people.
Zach also offers insight and advice for those trying to build a company–including the importance of investor updates because the most successful companies often have the highest frequency of reporting to stakeholders. He suggests that entrepreneurs should be open and honest about challenges, allowing investors to assist in problem-solving.
Zach also says it is important for entrepreneurs to demonstrate their products in a quick, iterative manner. He stresses that frequent engagement with customers can provide invaluable insights guiding the product development process. He further suggests that entrepreneurs should be tenacious with their vision, but flexible in their approach to achieving it.
Learn more about Zach.
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This episode is a conversation with Michael Clark the VP Global Head of Digital Transformation and Futurist at MasterCard. He discusses his upcoming book "Data Revolution, The New Currency of You" and what he believes will be a new paradigm in data ownership–that we will actually own our own data and benefit from its value. He also examines what role the law and regulation should play in it.
Michael and many others like him, believe that data is going to become a new currency and that to date, we have overlooked its value. Consumers have given up most of their control and access to this value because we have been too focused on what we were getting in exchange its use –i.e. The software tools we use.
Michael is well suited to write a book about the value of data. He has long worked in banking and spent a lot of time in the open banking world which, among other things, is a practice that provides third-party financial service providers open access to consumer banking information through the use of application programming interfaces (APIs).
For consumers to take back their data and capture its value, Michael says the focus needs to broaden from data privacy and also onto security, ethics, and bias in data usage
He says it is going to also take a new way of thinking–specifically more cooperation between regulators and the tech industry to effectively manage and leverage the tech fairly.
Michael also believes that the use of AI will play a big role in data management going forward because there is so much data, it will continue to grow and AI is the only way we are going to be able to understand what data tells us and harness its value.
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