Tax Planning for Lawyers: Turning Profit Into Long-Term Growth, with Jayden Doye

What happens when the best lawyer in the office becomes the boss? In episode 615 of the Lawyerist Podcast, Zack Glaser sits down with Debbie Foster and Stephanie Everett to talk about the leadership gap inside most law firms and why technical skill does not automatically translate into great leadership.  They explore why so many firms rely on “figure it out as you go” leadership, how that creates burnout and frustration, and why so many leaders end up becoming the bottleneck in their own business.  Debbie and Stephanie introduce their four leadership cornerstones and explain how law firm leaders can shift from solving every problem themselves to creating teams, systems, and workflows that work without constant intervention.  If you are tired of putting out fires all day, this episode is your reminder that leadership should feel more strategic and a lot less exhausting.  Listen to our previous episodes on Law Firm Leadership & Building Better Teams.  #600: Designing a Law Firm You Actually Want to Run, with Stephanie Everett Apple | Spotify | LTN  #597: What Lawyers Get Wrong About Teaching Clients and Teams, with Danielle Hall Apple | Spotify | LTN  #575: From Overwhelmed Lawyer to Strategic Law Firm Owner, with Chad Fox Apple | Spotify | LTN  #568: How to Build a Law Firm You Can Sell, with Victoria L. Collier Apple | Spotify | LTN  Links from the episode:  https://beanextlevelleader.com/    Chapters / Timestamps:  00:00 – Introduction  00:30 – Using AI as a Thought Partner  02:00 – Better Prompts, Better Leadership Decisions  05:30 – Meet Debbie Foster and Stephanie Everett  06:40 – What Are Next Level Leaders?  08:15 – Why Most Law Firms Don’t Train Leaders  10:05 – Learning Leadership the Hard Way  12:10 – The Four Cornerstones of Leadership  17:20 – From Heroics to Architecture  18:45 – Why Leaders Become the Bottleneck  20:10 – From Problem Solver to Multiplier  21:30 – Building Sustainable Leadership Systems  23:00 – Who This Program Is For  25:30 – The Book, Workbook, and Leadership Cohorts  28:00 – Leadership Is a Skill, Not a Title  29:00 – Closing Thoughts

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

Most law firms are designed for lawyers, not clients. And clients feel it. In episode 609 of the Lawyerist Podcast, Stephanie Everett sits down with Laura Hartnett to explore how design thinking can transform the way legal services are delivered.  Laura breaks down why clients often feel confused, anxious, or left in the dark, even when lawyers are doing excellent work. She shares how small changes, like rethinking communication, mapping the client journey, and understanding what happens after you deliver advice, can dramatically improve both client satisfaction and firm efficiency.  Together, they share practical ways to rethink your processes, clarify your communication, and deliver work clients can actually understand and use. If you want to build a law firm that feels clearer, more human, and easier to work with, this episode offers a smarter approach to designing your practice.  Listen to our previous episodes on Client Experience & Designing Better Legal Services.  #606: Breaking the Copycat Cycle: Building a Law Firm with Personality, with Patrick Patino Apple | Spotify | LTN  #600: Designing a Law Firm You Actually Want to Run, with Stephanie Everett Apple | Spotify | LTN  #597: What Lawyers Get Wrong About Teaching Clients and Teams, with Danielle Hall Apple | Spotify | LTN  #462: Designing an Empathetic Client Experience, with Kirk Simoneau Apple | Spotify | LTN    Links from the episode:  https://laurahartnett.com/  https://lawyerist.com/turn-ai-into-your-small-firms-advantage/    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  04:20 – Meet Laura Hartnett  05:00 – What “Design Thinking” Actually Means  06:05 – Why Client Experience Starts with Emotion  07:45 – Stop Inheriting Your Law Firm  08:40 – Where to Start: Understanding Your Client  10:20 – Mapping the Client Journey  12:15 – The Hidden Friction in Law Firm Processes  14:30 – Why Clients Don’t Understand Your Work  16:25 – Designing Deliverables Clients Can Use  18:20 – Lessons from Other Industries  19:05 – AI, Client Expectations & New Behaviors  21:40 – Teaching Clients When to Call You  23:00 – Redesigning Legal Services for the Future  25:00 – Staying Curious About AI & Change  27:00 – Closing Thoughts

In episode 608 of the Lawyerist Podcast, Stephanie Everett talks with former Big Law business development professional Megan Senese about the human side of legal marketing and why the most effective client development strategies often look less like selling and more like genuine connection.  For many lawyers, business development feels awkward, performative, and disconnected from the real work of practicing law. Megan challenges that assumption by showing how meaningful relationships, not sales tactics, are what actually drive sustainable growth.  They explore why traditional networking advice fails so many lawyers, how small thoughtful gestures can build stronger professional relationships, and why authenticity matters more than ever in a crowded legal marketplace. Megan also shares practical ideas for nurturing relationships, staying top of mind without being transactional, and approaching business development in a way that feels natural rather than forced.  If the idea of “doing marketing” makes you cringe, this episode offers a more sustainable approach to building relationships, trust, and ultimately a thriving legal practice.  Listen to our previous episodes on Law Firm Marketing & Differentiation.  #606: Breaking the Copycat Cycle: Building a Law Firm with Personality, with Patrick Patino 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  #549: A Journey into Video Marketing, with Temi Siyanbade Apple | Spotify | LTN  #515: Simple Marketing Hacks Lawyers Swear By, with Gyi Tsakalakis Apple | Spotify | LTN   Links from the episode: https://stage.guide     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  02:05 – Why Thoughtful Gestures Strengthen Professional Relationships  05:10 – Meet Megan Senese  06:25 – Why Business Development Feels So Hard for Lawyers  07:10 – How to Make Networking Feel Natural  09:20 – Why Copying Other Firms’ Marketing Doesn’t Work  10:15 – Turning Personal Interests into Business Development  12:30 – Simple Ways to Nurture Professional Relationships  14:00 – Staying Top of Mind Without Being Salesy  15:10 – How Long It Actually Takes to Build Client Relationships  16:05 – How to Ask for Business Without Feeling Awkward  18:05 – Why Listening Creates Better Pitch Opportunities  20:00 – Staying Curious About New Tools and Technology  23:00 – Closing Thoughts

AI is more than just another tool for lawyers. It may fundamentally change how law firms make money. In episode #607 of the Lawyerist Podcast, Stephanie Everett talks with legal industry analyst Jordan Furlong about the shifting economics of law practice and what happens as AI begins doing work lawyers once billed for.  Jordan explains why the traditional law firm model built on billable hours and human effort is starting to break down as legal workflows become automated. Together, they explore how AI may shift lawyers away from producing legal work and toward supervising systems, validating outcomes, and delivering the one thing machines cannot easily replicate: judgment under uncertainty.  The future of law practice may depend less on expertise and more on qualities machines struggle to replicate such as judgment, character, and the ability to guide clients through uncertainty. The conversation also explores why hourly billing may no longer make sense in an AI-driven world, how firms can rethink pricing around outcomes and client experience, and why smaller firms may adapt more quickly.  If the billable hour fades and AI begins handling the routine “widgets” of legal work, the real question becomes what a lawyer’s value is now, and how firms should prepare for what comes next.  Listen to our previous episodes on Artificial Intelligence and the Future of Legal 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  #587 – Future-Proofing Your Firm in the Age of AI, with Jack Newton Apple | Spotify | LTN  #577 – Rethinking Law Firm Growth in the Age of AI, with Sam Harden Apple | Spotify | LTN   Links from the episode:  https://jordanfurlong.substack.com.    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  01:45 – Why Everyone Is Talking About AI in Law  04:20 – Meet Jordan Furlong  06:40 – The Real Disruption AI Brings to Law Firms  09:30 – The Economics Behind the Billable Hour  12:50 – What Happens When Software Does the Work  16:05 – The Shift from Expertise to Judgment  19:20 – What Lawyers Still Do Better Than AI  22:40 – Client Value in an AI-Driven Profession  26:00 – Why Smaller Firms May Have an Advantage  29:10 – What This Means for New Lawyers  32:45 – Preparing for the Next Version of Law Practice  36:10 – Closing Thoughts

Standing out in a crowded legal market requires more than competence. It requires intentional client experience. In episode 606 of the Lawyerist Podcast, Zack Glaser talks with Patrick Patino about redefining professionalism and building a law firm people actually want to work with.  Patrick shares how he walked away from a successful bankruptcy practice to experiment with a more human-centered model focused on connection, accessibility, and community. They examine why most firms look and feel the same, how experience shapes client loyalty, and why fear-based marketing quietly undermines trust.  If you are questioning the traditional law firm playbook, this episode offers concrete ways to attract better clients, clarify your positioning, and design a firm that fits both your values and your market.  Links from the episode: https://podcasts.apple.com/us/podcast/the-newfangled-lawyer/id1699645225 Listen to our previous episodes on Client Experience & Law Firm Differentiation.  #603 – Turn Expertise into Clients: Building Authority That AI Recognizes, with Karin Conroy Apple | Spotify | LTN  #600 – Designing a Law Firm You Actually Want to Run, with Stephanie Everett Apple | Spotify | LTN  #575 – From Overwhelmed Lawyer to Strategic Law Firm Owner, with Chad Fox Apple | Spotify | LTN  #559 – The Imitation Trap: Lessons from 15 Years of Top Law Firm Websites, with Conroy Creative Counsel 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 – Introduction  01:15 – Discipline Is Boring Until Results Show Up  07:05 – Meet Patrick Patino  09:30 – Rethinking Professionalism  11:15 – High Five Legal and the Bankruptcy Experiment  13:30 – Fear Based Marketing vs. Levity  16:10 – Meeting Clients Where They Are  18:45 – Community Over Sales Pitches  20:50 – The Copycat Law Firm Problem  23:30 – Experience Is the Differentiator  26:05 – The Crumbl Cookie Model of Law  28:40 – Scaling Culture with the Pod Model  31:15 – Talking With Clients, Not At Them  34:00 – Collaboration Over Control  36:20 – Define Your Ideal Client for Real  38:45 – Solo and Small Firm Advantage  41:20 – What It Means to Be Newfangled