Lawyerist Podcast

Most law firm owners are highly strategic in their legal work, but far less intentional about their finances. And it shows up at tax time. 

In episode 614 of the Lawyerist Podcast, Bernadette Harris talks with Jayden Doye about the financial habits that quietly cost law firms thousands and why reactive tax preparation is not the same as real tax strategy. 

Jayden breaks down the key differences between bookkeeping, tax preparation, and tax planning, and explains why many lawyers overpay the IRS simply because they wait too long to act. They also explore common mistakes like misclassifying employees, relying on DIY accounting, and focusing on revenue instead of profit. 

Together, they share practical ways to take control of your numbers, build better financial systems, and make smarter decisions throughout the year, not just in April. 

If you want to stop guessing, reduce your tax burden, and run a more financially stable firm, this episode offers a more proactive approach to managing your practice. 

Listen to our previous episodes on Law Firm Profitability & Financial Clarity. 

#595 – KPIs for Lawyers: Measuring Your Law Firm’s Financial Health, with Bernadette L. Harris (Remastered) Apple | Spotify | LTN 

#583 – From Survival to Strategy: Scaling Your Law Firm Finances, with Bernadette Harris Apple | Spotify | LTN 

#575 – From Overwhelmed Lawyer to Strategic Law Firm Owner, with Chad Fox Apple | Spotify | LTN 

#558: The Wealthy Lawyer: Practical Financial Strategies for Legal Professionals, with Darren Wurz Apple | Spotify | LTN 

Links from the episode: 

https://theelawfirmcpa.com/home 

 

Chapters / Timestamps: 

00:00 – Introduction02:15 – Why Perfectionism Holds Lawyers Back08:10 – Meet Jayden Doye09:00 – The #1 Tax Mistake Law Firms Make10:45 – Why Doing It Yourself Costs More12:20 – Understanding the Financial Basics15:00 – How to Actually Lower Your Tax Bill17:00 – The Hiring Mistake That Can Trigger Audits19:00 – Are You Paying Yourself the Right Way?21:45 – Revenue vs. Profit (What Actually Matters)23:30 – Why Tax Bills Catch Lawyers Off Guard25:30 – Fixing the Problem Moving Forward26:40 – Simple Habits for Better Financial Control28:10 – The One Rule Every CPA Agrees On

Access to justice is not just a gap. It is a scale problem. In episode 613 of the Lawyerist Podcast, Zack Glaser talks with Zach Zarnow, Executive Director of Scale Justice, about what it really takes to reach more people without relying on more lawyers. 

Zach explains why traditional approaches like pro bono work, while valuable, are not enough to meet the overwhelming demand for legal help. Instead, Scale Justice focuses on building systems, tools, and partnerships that expand the reach of legal services through technology and collaboration. 

They explore how courts, legal aid organizations, and community groups can work together to meet people earlier in their legal journeys, why designing for real user needs matters more than ever, and how thoughtful use of technology can increase impact without sacrificing quality. 

If you are thinking about how to serve more clients, build more efficient systems, or rethink the role of your firm in a larger ecosystem, this episode offers a broader and more scalable way to approach legal services. 

Listen to our previous episodes on Access to Justice, Technology & Scaling Legal Help. 

#601: Beyond Chatbots: Using Agentic AI in Law Firm Intake, with Matt Spiegel Apple | Spotify | LTN 

#590: Innovating Without Overwhelm: Practical AI Tips for Lawyers, with Graydon Trusler Apple | Spotify | LTN  

#607: The Future of Law Firm Business Models in the Age of AI, with Jordan Furlong Apple | Spotify | LTN 

#600: Designing a Law Firm You Actually Want to Run, with Stephanie Everett Apple | Spotify | LTN 

Links from the episode: 

www.scalejustice.org 

Check out the episode on YouTube: https://youtu.be/4A3J-UjAdjQ 

 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X! 

 

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you. 

 

Access more resources from Lawyerist at lawyerist.com. 

 

Chapters / Timestamps: 

00:00 – Introduction 

04:40 – Meet Zach Zarnow 

06:20 – The Access to Justice Problem 

07:50 – Why More Lawyers Isn’t the Answer 

09:15 – Building Systems That Actually Scale 

11:10 – Partnering Instead of Selling 

12:30 – What It Means to Be Mission-Driven 

14:00 – Where the Courts Fit In 

15:30 – Solving Legal Problems Before They Escalate 

17:00 – Catching Legal Issues Early 

18:20 – Technology as a Force Multiplier 

19:10 – The Risks of DIY Legal AI 

21:05 – Who Should (and Shouldn’t) Use These Tools 

22:45 – Why Most Legal Tech Should Be Treated as an Experiment 

23:50 – What the Future Could Look Like 

25:00 – Ways Lawyers Can Contribute 

26:30 – Closing Thoughts

AI is not just another tool. It is changing how clients think, act, and make decisions. In episode 612 of the Lawyerist Podcast, Stephanie Everett talks with Cat Casey about what lawyers need to understand before AI creates problems they cannot fix. 

As more clients turn to tools like ChatGPT, lawyers are facing new challenges around trust, accuracy, and confidentiality. Cat explains why even lawyers who choose not to use AI still need to understand it, and how failing to do so can create real risks for both lawyers and their clients. 

They share practical ways to approach AI with the right mindset, including how to think about its limitations, how to use it as a thinking partner instead of a replacement, and how to guide clients who may not understand the consequences of using it. 

If you want to stay ahead of where the legal profession is heading, this episode offers a clear and actionable place to start. 

Listen to our previous episodes on Using AI in Law Practice. 

#601 – Beyond Chatbots: Using Agentic AI in Law Firm Intake, with Matt Spiegel Apple | Spotify | LTN 

#590 – Innovating Without Overwhelm: Practical AI Tips for Lawyers, with Graydon Trusler Apple | Spotify | LTN  

#580 – Smarter Law Firm Marketing: AI Tools That Actually Work, with FirmPilot Apple | Spotify | LTN 

#550 – Beyond Content: How AI is Changing Law Firm Marketing, with Gyi Tsakalakis and Conrad Saam Apple | Spotify | LTN 

Links from the episode: 

 https://thetechnocat.com/about 

Check out the episode on YouTube:

https://youtu.be/PQwAxiNjbhY

 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com. 

 

Chapters / Timestamps: 

00:00 – Introduction 

02:10 – A New Way of Working with AI 

05:00 – From Task Execution to Orchestration 

07:45 – Meet Cat Casey 09:30 – The Shift Happening Right Now in Law 11:15 – The Rise of AI in Client Behavior 13:45 – Understanding AI Without Getting Technical 16:35 – Why AI Is Not a Research Tool Replacement 18:50 – The Role of Judgment in an AI World 20:10 – AI as a Collaborative Tool 22:10 – Why Iteration Is Part of the Process 23:25 – When AI Creates Legal Risk 25:55 – Confidentiality and Privilege in Practice 27:10 – The Reality of Discoverability 28:20 – Lessons from Past Tech Shifts 29:30 – Where Lawyers Should Start

Most law firms don’t have a tech problem. They have a decision-making problem. 

In episode 611 of the Lawyerist Podcast, Zack Glaser talks with Scott Clasen about how to evaluate legal technology in a world where AI is changing everything and somehow making it more confusing at the same time. 

Too many firms are stuck buying more tools, chasing new features, and hoping the next platform will finally fix their workflow. Scott challenges that approach by shifting the focus away from software and back to systems, asking a more important question: what problem are you actually trying to solve? 

They explore the rise of AI-powered SaaS, the appeal of building your own tools, and why “AI-enabled” doesn’t always mean “useful.” The conversation also breaks down how to evaluate legal tech vendors, what contextual AI actually means, and how to think about long-term investments when the landscape keeps shifting every six months. 

If your tech stack feels bloated, expensive, or underwhelming, this episode offers a smarter way to make decisions that actually move your firm forward. 

Listen to our previous episodes on Legal Tech, AI, and Smarter Law Firm Systems. 

#601: Beyond Chatbots: Using Agentic AI in Law Firm Intake, with Matt Spiegel Apple | Spotify | LTN 

#590: Innovating Without Overwhelm: Practical AI Tips for Lawyers, with Graydon Trusler Apple | Spotify | LTN  

#587: Future-Proofing Your Firm in the Age of AI, with Jack Newton Apple | Spotify | LTN  

#575: From Overwhelmed Lawyer to Strategic Law Firm Owner, with Chad Fox Apple | Spotify | LTN  

 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X! 

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you. 

Access more resources from Lawyerist at lawyerist.com. 

 

Chapters / Timestamps: 

00:00 – Introduction02:00 – Lawyers Lab Updates03:55 – Meet Scott Clasen05:30 – SaaS Is Dead… Or Not06:45 – Building vs Buying Legal Tech08:30 – Paying for Tools You Don’t Use09:20 – AI Isn’t Always the Answer10:45 – Context Is What Makes AI Useful13:20 – AI That Works Like a Team Member15:10 – Making Smart Tech Investments16:30 – Start with the Problem, Not the Tool18:30 – Fixing Broken Workflows 

20:10 – When AI Does More Than Your Software21:50 – Custom Software Is Back23:15 – Where Your Data Should Live25:40 – The Build vs Buy Decision27:50 – Is This a Tech Revolution?30:10 – What Will Survive in Legal Tech32:00 – Where AI Is Heading33:30 – Closing Thoughts

In episode 610 of the Lawyerist Podcast, Zack Glaser sits down with Karin Conroy to unpack why so many law firm websites fail to convert and why AI is making the problem worse. 

Karin explains why copycat marketing has always been ineffective, and how the rise of AI generated content is accelerating a wave of sameness across legal websites. As tools make it easier than ever to produce content quickly, the firms that stand out are not the ones moving faster, they are the ones thinking more strategically about differentiation, trust, and positioning. 

The conversation explores what actually matters on a modern law firm website, from messaging that resonates in seconds to branding that signals credibility to both humans and algorithms. Zack and Karin also break down where AI fits into a smart marketing strategy and where it quietly undermines it. 

If your website looks good but is not bringing in clients, this episode will help you rethink what “working” really means. 

Listen to our previous episodes on law firm marketing with Karin Conroy:   

#603: Turn Expertise into Clients: Building Authority That AI Recognizes, with Karin Conroy Apple | Spotify | LTN 

#584: How to Stay Human in the Age of AI-driven Law Firm Marketing, with Creative Conroy Apple | Spotify | LTN  

#559: The Imitation Trap: Lessons from 15 Years of Top Law Firm Websites , with Conroy Creative Counsel (Sponsored) Apple | Spotify | LTN   

#546: Unlock Law Firm Growth: AI marketing Secrets with Karin Conroy Apple | Spotify | LTN 

Links from the episode: 

https://www.conroycreativecounsel.com/lawyerist/

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you. 

Access more resources from Lawyerist at lawyerist.com. 

 

Chapters / Timestamps: 

00:00 – Introduction 

02:00 – Meet Karin Conroy 

03:45 – The Problem with Copycat Websites 

06:00 – Why “Inspiration” Turns Into Sameness 

08:30 – AI Slop Before AI 

10:30 – If You Look the Same, You Compete on Price 

12:30 – What Your Website Should Actually Do 

14:30 – The 3 Second Rule 

16:00 – Messaging That Makes Clients Feel Understood 

18:30 – Stock Photos and Fake AI Images 

21:00 – Using AI Without Killing Your Brand 

24:00 – Why Most Bio Pages Fail 

27:00 – What Clients Actually Care About 

29:30 – Trust Signals That Matter 

32:00 – Content Is Cheap, Expertise Is Not 

35:00 – How to Stand Out in a Sea of Sameness 

38:00 – The Only Shortcut That Works 

41:00 – Closing Thoughts