Best Document Automation Podcasts (2025)

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How I broke Claude's "Unlimited" $200 plan 1:13:32

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4d ago1:13:32

1:13:32

After a surprisingly affordable and delicious trip to Vancouver, we're back and diving headfirst into the AI world's latest obsession: the talent war. Meta is swinging for the fences, reportedly dropping $100 million offers to poach top researchers from OpenAI. This has sparked a war of words, with OpenAI framing it as "stealing" and pitting their …

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What's A Good Invoice 9:44

5d ago9:44

9:44

Is that invoice ready for payment? In accounts payable, best practice accounting organizations like to say, A good invoice gets a good payment. What makes an invoice good? It’s a lot more complicated than it might seem. Best practice accounts payable teams look at 8 different factors. Let’s look at them together. #accountspayable #threewaymatch #in…

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078. Build Financial Clarity into Your Law Firm with CFO Danielle Hendon 1:01:28

6d ago1:01:28

1:01:28

Law firm owners often feel overwhelmed by their financial statements, staring at QuickBooks reports that seem to tell only half the story. The disconnect between having financial data and understanding what it means for strategic decision-making creates unnecessary anxiety and missed opportunities. In this episode, I'm talking with Danielle Hendon,…

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The Biggest AP Automation Issues No One Talks about 38:02

11d ago38:02

38:02

Costly overlooked issues that no one talks about could derail your accounts payable or accounting automation project. But once you know what they are, you can work around them AND recognize them when they arise. Link to The Managing Interruptions Survival Guide https://youtu.be/lAaVtX1Y1vU Subscribe for more tips and insights like this: https://www…

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Special Episode Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 42 29:43

11d ago29:43

29:43

In this 42nd episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the mid-year recap, selecting the proper AI tool, merger mania, and creating a competitive advantage in legal.By Ari Kaplan

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Episode 5 | Navigating the Future of Outbound Sales with AI 45:11

11d ago45:11

45:11

In this episode of the Run Point Podcast, hosts Matthew Hall and Sam Gaddis engage with Shane Stearns to explore the evolving landscape of outbound sales, particularly in the context of AI. They discuss the historical eras of outbound sales, the challenges of the sequencing era, and the importance of quality over quantity in sales strategies. Shane…

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How to Think About AI 26:25

13d ago26:25

26:25

I spoke with Professor Richard Susskind CBE KC (Hon), President of the Society for Computers and Law and author of many notable books, including his most recent publication, How to Think About AI - A Guide for the Perplexed. We discussed strategies for balancing the benefits and risks of artificial intelligence, how technology can help legal profes…

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077. The BEST System for Managing Legal Work: Kanban for Lawyers Part 3 37:02

13d ago37:02

37:02

Legal teams face a unique challenge that factory floors and software developers rarely encounter: managing dozens of active matters simultaneously while dealing with constant interruptions from clients, opposing counsel, and courts. You're juggling multiple cases, each with its own timeline, dependencies, and unpredictable external factors that can…

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Trial Balance vs Balance Sheet What's the difference 8:48

13d ago8:48

8:48

Are the trial balance and the balance sheet the same thing? Of course not. But, confusion between the two is more common than you might imagine. Let’s take a look at both of them so you understand what they are, how each is used and how they are different. They are both used in accounting, accounts payable and finance. But that is about where the s…

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The AI CLI war: who’s winning?! 1:07:39

18d ago1:07:39

1:07:39

One year in the books! We're popping the non-alcoholic champagne to celebrate the first anniversary of the Breakeven Brothers podcast. In that time, the AI landscape has shifted from a gentle tremor to a full-blown earthquake, and in this episode, we're navigating the aftershocks. The AI arms race is escalating, with tech giants like Meta opening u…

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How Generative AI is Affecting the Demand for Legal Services and the Need for AI Fluency 11:19

19d ago11:19

11:19

I spoke with Subroto Mukerji, the CEO of Integreon, an alternative legal and global managed services provider. We discussed how generative AI is affecting the demand for legal services, the value of “AI fluency” in the legal field, and how the legal operations discipline is evolving as generative AI becomes increasingly embedded in legal workflows.…

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076. How Scrum Lessons Can Improve Your Law Practice: Kanban for Lawyers Part 2 37:36

20d ago37:36

37:36

Back in the early 2000s, software teams started embracing a new way of working that turned conventional project management on its head. Instead of trying to define everything up front and push massive projects toward a distant deadline, they asked a different question: what’s the most valuable work we can deliver in the next two weeks? That questio…

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How Digital Transformation is Reshaping Legal Marketing in 2025 11:19

21d ago11:19

11:19

I spoke with Sonya Palmer, the Senior Vice President of Operations at Rankings.io, a marketing company for lawyers. We discussed how digital transformation is reshaping legal marketing in 2025, the types of marketing law firms should prioritize to stay competitive, and the key elements of a strong legal brand.…

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AI In Healthcare: The Invisible Revolution 39:57

21d ago39:57

39:57

AI is reshaping healthcare in ways we couldn’t have imagined a decade ago.In this episode, we explore innovative use cases of AI in healthcare research — from helping doctors predict treatment outcomes to streamlining operations by managing information flows more efficiently. We’ll hear compelling insights from experts like ⁠Dr. Jack Gilbert⁠, co-f…

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Balancing Innovation and Security in Analytics with Oren Falkowitz of Gigasheet 35:11

25d ago35:11

35:11

Security isn’t just a checkbox — it’s the foundation of trustworthy data analytics. Oren Falkowitz, Advisor at Gigasheet, joins us to explore what it really takes to secure data in the digital era. With a background spanning NSA, US Cyber Command, Amazon and Cloudflare, Oren brings a deep understanding of how to strike a balance between access and …

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How Legal Professionals Can Articulate Their Value in an Era of Agentic AI and Automation 17:35

25d ago17:35

17:35

I spoke with Bjarne Tellmann, the founder of FjordStream Advisors, a boutique consultancy that provides advisory services and executive coaching to the legal industry. We discussed the most valuable areas of digital transformation for a law firm, how to build teams that will drive a legal organization into the future, and how legal professionals ca…

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Bookkeeper’s Guide to Accounts Payable 1:07:18

27d ago1:07:18

1:07:18

ookkeeping and accounts payable are closely connected, with many bookkeepers performing the accounts payable function. This guide is designed to ensure those doing that do so in a efficient and effective manner, while protecting against fraud and collecting all data necessary for complete regulatory compliance. This is harder than it sounds. #bookk…

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The Benefits of Leveraging Client Intelligence 9:50

27d ago9:50

9:50

I spoke with Andy Seavers, the Co-Founder and CEO of Case Status, a client engagement platform focused on connecting consumer law firms with their clients. We discussed the importance of a new approach to client engagement for modern law firms, the ethical challenges associated with deploying legal technology, and how AI and data analytics are resh…

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075. Legal Workflow Lessons from the Factory Floor: Kanban for Lawyers Part 1 40:06

27d ago40:06

40:06

A Japanese automobile factory floor in the 1950s might seem worlds away from your law office, but the visual management systems that transformed Toyota's manufacturing process hold powerful lessons for modern legal practice. The same principles that helped Toyota become a global automotive giant can help you create smoother workflows, reduce overwh…

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From Diapers to Deal Flow: How We Actually Use AI All Day 27:14

1M ago27:14

27:14

AI isn’t coming—it’s already in your pocket and on your P&L. In this RunPoint Podcast episode, Matthew Hall and Sam Gaddis break down the real-world ways they’re using generative AI to: Out-think the spreadsheet – build cash-flow models, plan investments, and pressure-test big bets in minutes. Parent with data – get actionable, guilt-free advice on…

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Redefining Legal Operations to Adapt to Uncertainty and Change 11:52

1M ago11:52

11:52

I spoke with Will Seaton, the Chief Customer Officer at DraftWise, Dan Wallace, the Vice President of Sales for the North American Markets at Neota, and Laura Wenzel, the Global Marketing & Insights Director at iManage. The three companies are part of a consortium supporting a new report featuring the perspectives of 31 legal operations leaders, ti…

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Agent to Agent: Google’s ADK and the new frontier of AI 1:20:17

1M ago1:20:17

1:20:17

On this Michael Jordan episode (23!), we kick things off with a classic tale of a "five-minute" project gone wrong. Bradley shares his ambitious attempt at a parking lot car battery replacement that quickly turned into a 30-minute fishing expedition for a single lost part. Meanwhile, Bennett recounts a white-knuckle flight experience made even more…

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Cash Management: Best Payables and Receivables Practices that AREN'T! 8:16

1M ago8:16

8:16

When it comes to cash management, sometimes accounting and finance professionals miss the big picture … and they miss it big time. They can’t see the proverbial forest for their focus on the single cash tree. Today we’re going to take a look at both sides of the equation – payables and receivables – where cash management can make a difference – and…

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074. Using Kanban to Manage Capacity 28:59

1M ago28:59

28:59

In law firms across the country, I'm seeing a concerning pattern emerge when one attorney adopts Kanban and Agile methods while their partner - often from an older generation of lawyers - resists these systematic approaches. This clash of perspectives frequently pushes teams back into overload and burnout. This week, I explore how this capacity ten…

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Amplifying Community Voices Through Data with Russell Stevens of MIT Center for Constructive Communication 44:40

1M ago44:40

44:40

Data doesn’t just reflect communities — it can help shape more inclusive, constructive conversations. We’re joined by Russell Stevens, Head of Strategy and Development at the MIT Center for Constructive Communication, to explore how qualitative data, storytelling and ethical AI design can bridge gaps in society and decision-making. Russell shares h…

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Critical Accounts Payable Document Problems

1M ago

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Not understanding the nuances of the three critical accounts payable documents has caused more than a few accounting professionals countless hours of anguish. For one tiny misstep with regards to these documents can translate into duplicate payments, paying for something the supplier is supposed to pay for, paying too high a price or even worse, fr…

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Adapting ESI Protocols to Address Hyperlinked Files 15:22

1M ago15:22

15:22

I spoke with Brandon D’Agostino, Vice President of Product at Cloudficient, a provider of information governance and e-discovery software. We discussed the rise of hyperlinked documents in e-discovery, the legal challenges of preserving and collecting hyperlinked files, and adapting ESI protocols to address hyperlinked files.…

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AI, Admin and the Future of Legal Work - How Your Role is Evolving in the Digital Workspace 34:07

1M ago34:07

34:07

To accompany our recent white paper - How Your Role is Evolving in the Digital Workspace, we have recorded this podcast where Pippa Shepherd, our Head of Customer Engagement, speaks with our new CEO, Anthony Philips, and our Head of Innovation and AI, John Black. They unpack the results, share additional context and explore real-world implications …

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Accounts Payable Management for Controllers 9:06

1M ago9:06

9:06

So, what’s the big fuss about accounts payable, you may wonder, isn’t it just another accounting function … and one of the more simple ones at that! Let me answer that politely- although you if you know me well, you know what’s going through my mind. Yes, it is part of accounting and NO – it is NOT simple. Get even one tiny part wrong and you could…

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073. Don't Let Magical AI Thinking Cloud Your Sense of Capacity 22:31

1M ago22:31

22:31

A concerning trend I've noticed both in my own practice and among my clients is that the rise of AI technology is making it harder to accurately assess our true capacity. Between constant marketing messages and the promise of enhanced productivity through AI tools, many of us are failing to gauge our own capacity and falling into the trap of overco…

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Closing the Gaps by Modernizing Legal Document Management 15:47

1M ago15:47

15:47

I spoke with Peter James, a Senior Partner with @DOCS, and David Leong, the Chief Technology Officer with @GROUP about how modern law firms navigate document management challenges, what post-COVID print volumes and workflows reveal about document production, and the webinar - Closing the Gaps by Modernizing Legal Document Management - on Wednesday,…

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Lexpo Special Balancing Legal and Business Risks to Ensure the Success of Large-Scale Digital Transformations 14:26

1M ago14:26

14:26

I spoke with Tommi Ogi Possnert, a legal industry leader based in Stockholm and a featured speaker at the Lexpo Conference, taking place in Amsterdam on June 16th and 17th. We discussed the most common challenges companies face when implementing new technologies in legal, how to balance risks to ensure the success of large-scale digital transformat…

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Paying $200/month for Claude Code... here's why 1:20:28

2M ago1:20:28

1:20:28

Guess who's finally back from an epic honeymoon adventure through Japan and Korea?! Bradley rejoins Bennett, and after a two-and-a-half-week AI news whirlwind, we've got A LOT to unpack. We're kicking things off by calling out the "Propaganda We're Not Falling For," tackling everything from overhyped agent overload and why some popular frameworks a…

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Embracing Legal Innovators in California, London, and New York 13:33

2M ago13:33

13:33

I spoke with Richard Tromans, founder of Tromans Consulting and Artificial Lawyer, which is the co-producer of the Legal Innovators Conference Series, including Legal Innovators California in San Francisco on June 11th and 12th. We discussed the genesis of Artificial Lawyer, the inspiration for the Legal Innovators Conference, the importance of fac…

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5 Simple Upfront Vendor File Verifications that Most Overlook 8:57

2M ago8:57

8:57

Time and again, organizations skip critical vendor setup checks when setting up new vendors in the master vendor file, setting themselves up for financial losses, operational nightmares, and worst of all—an irate boss or board of directors demanding answers. Make sure you stick around until the end when we discuss the one task that many take a lack…

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072. The Hidden Dangers of Overcapacity 32:15

2M ago32:15

32:15

We don’t talk about overcapacity enough in legal practice, especially not the hidden ways it erodes performance, burns out your team, and stalls your cases. In this episode, I take a closer look at what really happens when you’re operating beyond your firm’s functional capacity. From unnecessary administrative overhead to frustrated clients and che…

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Revisiting the Best Practices for Business Development Success 15:25

2M ago15:25

15:25

I spoke with Alistair Marshall, the Director and Owner of Professional Services Business Development, a consultancy that focuses on strategy, marketing, and business development for law firms worldwide. He is the author of the newly released Grow Your Professional Services Practice – The Practical Guide to Business Development. We discussed best pr…

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The Rising Demand for Cybersecurity and E-Discovery Talent 9:52

2M ago9:52

9:52

I spoke with Tom Chapman, the Co-Founder of Iceberg, a specialist recruitment firm focused on cybersecurity and e-discovery. We discussed how the demand for cybersecurity and e-discovery talent has evolved, the challenges companies face when hiring for these roles, and how AI and automation are impacting hiring in cybersecurity and e-discovery.…

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8 Untapped Ways to Use LinkedIn 9:39

2M ago9:39

9:39

Think LinkedIn is just for job hunters? Think again. Even if you love your job and plan to stay put, skipping LinkedIn today is a huge mistake for accounting, accounts payable, finance, and treasury professionals. . It’s not just about checking for job openings, it’s the platform every professional interested in their long-term career needs to be o…

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Open-Source Intelligence and Why it Has Become Vital to Modern Legal Operations 11:02

2M ago11:02

11:02

I spoke with Rick Campbell, the Executive Chairman and CEO of @GROUP, and Matt Winlaw, the CEO and Managing Director of @ID, one of three divisions that includes @DOCS and @SOFT, within @GROUP. We discussed open-source intelligence, why OSINT has become vital to modern legal operations, the blind spots in traditional legal risk models, predictive b…

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071. How Trauma Informed Lawyering Helps Avoid Burnout with Dr. Colin James 59:05

2M ago59:05

59:05

The impact of trauma in legal practice extends far beyond individual client interactions. From law school through retirement, lawyers face unique psychological challenges that can fundamentally alter their personalities, relationships, and effectiveness as advocates. Dr. Colin James, author of "Vicarious Trauma and Burnout in Law," brings decades o…

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Episode 3 - Google I.O., newsletter automation, voice memos, AI tools, private equity, AI quality, sycophancy, technology trends 41:40

2M ago41:40

41:40

keywords AI, ChatGPT, Google I.O., newsletter automation, voice memos, AI tools, private equity, AI quality, sycophancy, technology trends summary In this episode of the Run Point podcast, hosts Sam Gaddis and Matthew Hall discuss practical AI tools that can be utilized immediately, including voice memos and ChatGPT projects. They also explore the …

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Special Episode Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 41 22:28

2M ago22:28

22:28

In this 41st episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed value-based billing, driving firmwide innovation, and cultivating a willingness to be engaged.By Ari Kaplan

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Building Emotional Loyalty Through Data with Claudia Infante of Margaritaville 38:56

2M ago38:56

38:56

Data is the backbone of every great brand, but for Margaritaville, it’s also the bridge to a lifestyle of laid-back escapes and unforgettable memories. Claudia Infante, Chief Data Officer of Margaritaville, joins us to explore how this iconic brand blends data-driven decisions with the spirit of escapism. Claudia shares insights into the company’s …

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A New Standard of Accounting Excellence in Accounts Payable The 1% Solution 9:08

2M ago9:08

9:08

You can make your Accounts Payable team in Accounting dramatically more efficient without spending a dime on new technology. Let me show you 8 simple tactics to enhance your accounting operations. Stick with me—because by the end of this video, I’ll show you a tactic few even think to use – and it will leave you slapping your head saying, “why didn…

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CLOC CGI 2025 Mixtape 7:05

2M ago7:05

7:05

I was lucky to have many great conversations with industry leaders at the 2025 CLOC (Corporate Legal Operations Consortium) Global Institute, which I captured in this #ReinventingProfessionals #Mixtape 😀 Thanks to the following participants for sharing their insights: 🎙️ David Blazejewski (David Blaze), Chief Revenue Officer, TruthOrLie.ai 🎙️ Tim B…

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070. Profit First for Lawyers: A Conversation with RJon Robins 51:45

2M ago51:45

51:45

Is your law practice truly profitable? Not just cash-flow positive, but actually generating the kind of profit that allows you to serve your clients well, take care of your team, and live the life you want? In this episode, I dive deep into the critical topic of law firm profitability with RJon Robins, founder of How to Manage a Small Law Firm and …

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Enhancing a Legal Practice with Generative AI-Empowered Conversational Intelligence 13:09

2M ago13:09

13:09

I spoke with Hilary Bowman, a healthcare attorney, who is the Founder of Querious, an application that facilitates virtual lawyer-client conversations using generative AI. We discussed how artificial intelligence can help legal professionals optimize client conversations, the value of real-time legal insights, and how the attorney-client relationsh…

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The State of Accounts Payable Today: Lessons Learned over 20 Years 9:07

2M ago9:07

9:07

Recently, AP Now (and I celebrated) our twenty-year anniversary. That’s 20 years of covering accounts payable, accounting, payment and job interview issues. Kind of a State of the Union, Here’s a look at the State of Accounts Payable today or 20 Lessons Learned. Link to Using AI in Accounting and AP playlist https://whttps://www.youtube.com/playlis…

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Reshaping the Competitive Landscape for Solo Practitioners and Small Firms 11:51

2M ago11:51

11:51

I spoke with Ruchie Chadha, the President of Smokeball US, an AI-powered legal practice management software platform that helps small law firms stay organized, productive, and profitable. We discussed the importance of trust accounting, empowering lawyers by partnering with state bar associations, and leveraging technology to reshape the competitiv…