Well Counseled

About Well Counseled

General Legal is an AI-native law firm where world-class attorneys serve companies with unmatched precision and speed, billing for outcomes, not hours. Learn more here: https://general.legal/?utm_source=podcast-feed&utm_medium=social&utm_campaign=evergreen_well-counseled

Publisher

General Legal

Category

business

Language

en

Explicit

No

First episode

29 Sept 2026

Latest episode

10 Nov 2026

Latest episodes

8 episodes in the feed.

1. 

   10 Nov 2026

   AI Raises the Bar for Legal Client Service | Will Holman, Head of Customer Strategy and Expansion

   Katrina Barry sits down with Will Holman, Founding Head of Client Strategy and Expansion at General Legal, for an episode of Well Counseled exploring how AI is changing client expectations, legal pricing, and the way law firms deliver value. After nearly 13 years as a litigator, Will transitioned into legal technology and customer success, helping law firms adopt generative AI at Casetext and advising Fortune 200 legal departments on outside counsel strategy at PERSUIT. He shares what those experiences taught him about client relationships and how AI is changing the economics of legal services. Will also discusses responsible AI adoption, the importance of human judgment, and why better legal service requires more than technical expertise. From upfront pricing to stronger client relationships, he explores what law firms can do to meet rising expectations. AI Raises the Bar for Legal Client Service | Will Holman, Head of Customer Strategy and Expansion at General Legal 00:00 - How AI is challenging traditional legal pricing 00:37 - Meet Will Holman, Head of Client Strategy and Expansion at General Legal 01:46 - From 13 years in litigation to a new career in legal technology 05:41 - Finding fulfillment in customer success 06:23 - What lawyers can learn from listening to their clients 09:12 - Why winning an argument isn't the same as winning a client relationship 10:41 - Why lawyers need to think more about customer service 11:53 - Inside the launch of CoCounsel at Casetext 14:22 - Why changing lawyers' workflows is harder than demonstrating AI 16:02 - Why AI cannot replace legal judgment and expertise 16:49 - The billable hour and the rising cost of legal services 19:12 - Should clients pay less when AI makes lawyers more efficient? 21:17 - Is the billable hour dying? 22:53 - Responsible AI adoption, confidentiality, and client trust 26:02 - What's holding legal teams back from adopting AI? 27:48 - How AI can free lawyers to focus on strategy 30:38 - What clients value most when buying legal services 31:49 - What law firms can learn from technology companies about client relationships 34:05 - What clients misunderstand about AI-native law firms 35:41 - Building the future of General Legal's enterprise client relationships 36:40 - Counsel in 60: Rapid-fire questions 42:16 - Will's closing advice on evolving client service in the legal industry “If you can take a task that used to be five hours and you can now do it in 20 minutes, it should absolutely be cheaper than what the billable hour alternative would have been.”

2. 

   20 Oct 2026

   Building Relationships, Building Community | Brooke LeBlanc, Head of Community at Corgi Insurance

   What turns an audience into a real community? In this episode of Well Counseled, Katrina Barry sits down with Brooke LeBlanc, Head of Community at Corgi Insurance, to talk about how to build the one-to-one relationships which turn into lasting communities and 'fandom' for powerful brands. They get into the difference between followers and true believers, how Corgi’s cafés create meaningful in-person connections, the strategy behind Brooke’s personal brand, what happens when a post goes unexpectedly viral, and how companies can measure the business value of community. Brooke also shares how relationships compound over time, as well as her perspective on why human connection will become even more important as AI improves. Building Relationships, Building Community with Brooke LeBlanc, Head of Community at Corgi Insurance 00:00 - The difference between an audience and a community 00:24 - Meet Brooke LeBlanc, Head of Community at Corgi Insurance 01:26 - From fintech sales to building community in San Francisco 03:20 - The unconventional interview that brought Brooke to Corgi 05:49 - What building a real community actually means 07:31 - The biggest mistake companies make when building community 09:19 - Turning followers into members and evangelists 11:27 - Building an intentional personal brand 14:21 - The cost of becoming highly visible online 16:12 - Why physical spaces create deeper connections 21:10 - Going viral and losing control of your online narrative 25:04 - Turning community into a business function and measuring its ROI 27:56 - Can a strong community compensate for a weak product? 28:58 - AI and the future of human connection 30:36 - Counsel in 60: High-speed Q&A 32:08 - The power of compounding relationships 33:11 - What Brooke hopes changes over the next five years “The value of a community is the quality of each one-on-one connection you have.” “People hate being sold to, but they love going shopping with friends.” Find Brooke on: Instagram – https://www.instagram.com/mbrookeleblanc/ (https://www.instagram.com/mbrookeleblanc/) X – https://x.com/brookeleblanc (https://x.com/brookeleblanc) Check out Corgi Insurance at https://www.corgi.insure/ (https://www.corgi.insure/) Check out General Legal at https://general.legal/ (https://general.legal/)

3. 

   13 Oct 2026

   Transforming Legal Services: Product at an AI-Native Law Firm | J.P. Mohler, CPO of General Legal

   What does it mean to treat the client experience at a law firm as a product? In this episode of Well Counseled, Katrina Barry sits down with J.P. Mohler, co-founder, Chief Product Officer, and Managing Partner of General Legal, to talk about his path from building mobile apps to Harvard Law, practicing corporate law at Cooley and WilmerHale, and developing AI tools at Casetext. They get into what startup founders really need from their lawyers, how General Legal builds technology to help attorneys deliver high-quality work faster, why Slack and upfront pricing are central to the client experience, and why adopting AI only makes a difference when a firm’s incentives reward efficiency. Transforming Legal Services: Product at an AI-Native Law Firm with J.P. Mohler, Chief Product Officer and co-founder of General Legal 00:00 - Why founders value speed and responsiveness from their lawyers 00:24 - Meet J.P. Mohler, co-founder, Chief Product Officer, and Managing Partner of General Legal 02:01 - iOS app engineering before law school 05:04 - Moving from software engineering to law 06:35 - Why J.P. chose law and founded the Harvard Law and Technology Society 09:33 - What representing startups taught him about the client experience 11:56 - Advising clients during the Silicon Valley Bank collapse 15:05 - Leaving corporate law to build legal technology at Casetext 17:57 - Developing early AI systems for judges and prosecutors 19:17 - What it means to run product at a law firm 20:27 - Building technology that helps lawyers work faster 23:07 - How General Legal designed its client experience 24:55 - Designing legal services that feel effortless for clients 26:47 - How General Legal decides what technology to build next 28:26 - AI, human judgment, and the incentives shaping adoption 30:39 - Why having AI does not automatically improve the client experience 31:52 - Counsel in 60: High-speed Q&A 32:43 - Is AI transforming legal services fast enough? 33:37 - The best advice J.P. received as a young associate 35:33 - Where J.P. sees General Legal in five years 36:06 - How technology is changing access to expert legal counsel Check out General Legal at https://general.legal/ (https://general.legal/)

4. 

   2 Oct 2026

   Well Counseled, Episode 1: Honey's former GC on key legal issues at start-ups

   This is the first episode of Well Counseled, a series about the legal questions founders face while building companies. Katrina Barry sits down with Chris Grogan, Managing Partner of Emerging Companies and Venture Capital at General Legal, to talk about how AI is changing legal work, why human judgment still matters, and the legal decisions founders should get right early. They get into co-founder vesting, SAFEs versus priced rounds, preparing for founder departures, choosing the right counsel, and what it actually means to build an AI-native law firm. AI-Native Law Firms, Founder Mistakes, and Startup Legal Advice with Chris Grogan Timestamps: 00:00 - What Well Counseled is about and why this show exists 01:21 - Meet Chris Grogan and what an ECVC lawyer does 05:03 - Why Chris joined General Legal 08:05 - What AI-native means in a law firm 10:26 - How AI fits into client intake and legal workflows 12:55 - What AI can do to legal turnaround times 14:51 - Addressing quality concerns around AI in legal work 16:17 - Where AI genuinely improves client outcomes 18:35 - The first legal mistakes founders make 20:25 - Why co-founder vesting should be handled early 21:21 - When a SAFE makes more sense than a priced round 24:22 - What to plan for before a co-founder departure 27:12 - How first-time founders should choose counsel 28:08 - What lawyers and founders should understand about each other 32:29 - Counsel in 60 - High-speed Q&A Chris' LinkedIn: https://www.linkedin.com/in/chrisgrogan (https://www.linkedin.com/in/chrisgrogan) Katrina's LinkedIn: https://www.linkedin.com/in/katrinabarry2/ (https://www.linkedin.com/in/katrinabarry2/) Check out General Legal at https://general.legal/ (https://general.legal/)

5. 

   2 Oct 2026

   What Every Co-Founder Agreement Needs Before You Build Anything: Employment Lawyer Robert Wennagel

   Most founders wait too long to think about the people side of their company. In this episode, Well Counseled host Katrina Barry speaks with Robert Wennagel, employment attorney at General Legal, to break down the legal mistakes that can cost founders the most, sometimes hundreds of millions of dollars. They get into founder separations, confidentiality and IP agreements, what happens when employee relationships go wrong, why outsourcing HR doesn’t eliminate legal liability, and the growing risks around using AI in hiring. Employment Mistakes Founders Make, IP Protection, and AI in HR Timestamps: 00:00 - The hidden cost of not planning for founder conflict 00:19 - Meet Robert Wennagel and the employment issues founders overlook 03:08 - The optimistic founder mindset that creates legal blind spots 06:59 - Setting up the right legal posture before investors arrive 08:27 - Why IP assignment agreements matter for every contributor 10:14 - What happens when a co-founder leaves without the right paperwork 14:03 - The dangerous gap between starting work and signing agreements 17:08 - What startups should outsource as they begin hiring 22:18 - What fractional HR, staffing agencies, and EORs actually do 24:25 - Why outsourcing HR doesn’t eliminate legal liability 27:13 - The documentation problem behind performance and firing decisions 30:04 - How severance agreements work and why legal review matters 32:12 - What happens to founder equity after a separation 35:33 - How AI is changing recruiting and hiring 36:24 - New AI rules around notice, opt-out, and bias audits 39:13 - Why employers can still be liable for discriminatory AI decisions 42:26 - Employee data privacy obligations under GDPR and CCPA 44:24 - The most common mistake: weak confidentiality and IP agreements 46:36 - Where AI and HR are likely to collide next “It costs you nothing to get that piece of paper signed at the very beginning and it could cost you hundreds of millions of dollars if you don't get it signed.” Check out General Legal at https://general.legal/ (https://general.legal/)

6. 

   2 Oct 2026

   How Founders Get Caught Off Guard by Acquisition Diligence

   How do you prepare your company for an acquisition before an offer lands? In this episode of Well Counseled, Katrina Barry sits down with Shanita Nicholas, senior counsel at General Legal, to talk about what founders can do long before diligence starts to make a future deal easier. They get into why your cap table tells the story of your company, what buyers look for in your financials and documentation, how to think about your ideal exit early, and the legal and operational cleanup that can keep diligence from becoming a last-minute scramble. How to Prepare for an Acquisition: a discussion with Shanita Nicholas, Senior Counsel at General Legal Timestamps: 00:00 (https://www.youtube.com/watch?v=OgNYG-9qZTc&pp=0gcJCWMAwfN6Pr3D) - Why your cap table tells the story of your company 00:50 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=50s) - Meet Shanita Nicholas and her M&A background 03:37 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=217s&pp=0gcJCWMAwfN6Pr3D) - Why selling your company doesn’t necessarily mean you’re done 05:19 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=319s) - What actually makes a company ready to sell 07:26 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=446s) - Financial readiness, burn, and runway 10:06 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=606s) - Why clean paperwork matters to buyers 11:14 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=674s) - Deciding your ideal exit years in advance 13:03 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=783s&pp=0gcJCWMAwfN6Pr3D) - The accounting cleanup founders leave too late 14:52 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=892s) - What founders can do themselves before hiring counsel 17:46 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=1066s) - The cap table problems founders discover mid-deal 19:41 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=1181s) - Control, governance, and money on the cap table 22:21 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=1341s) - Acquihires and whether founders actually want to stay 24:01 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=1441s) - Counsel in 60 - High-speed Q&A 25:52 (https://www.youtube.com/watch?v=OgNYG-9qZTc&t=1552s) - Final advice Check out General Legal at https://general.legal/ (https://www.youtube.com/redirect?event=video_description&redir_token=QUZZTVljRW1zOXFJcGJBellBdm4yWmpjTG92eXxBTl9pYzRlR3lBeF9BdENGV2lMOXRoWkpUWWRTaWhRQjZmaUM3NEY0bGlVWE9vd0xPTUY2QTlIZ01zVXdVTEtnNUY4NU5qTWU5aHYzNWhnS2lpRTdkdGg0czZkUGdHTG82RjJh&q=https%3A%2F%2Fgeneral.legal%2F&v=OgNYG-9qZTc)

7. 

   1 Oct 2026

   Engineering for AI-Native Legal Practice with Javed Qadrud-Din, CTO of General Legal

   What does it actually mean to build a law firm around AI from day one? In this episode of Well Counseled, Katrina Barry sits down with Javed Qadrud-Din, co-founder and CTO of General Legal, to talk about his path from coding as a kid to practicing corporate law at Fenwick & West to building some of the earliest deep learning tools for legal research. They get into why AI is dramatically better at coding than legal work, how General Legal uses AI to do the “grunt work” while keeping lawyers in the loop, why a law firm’s private data may become one of its biggest advantages, and what legal work could look like five years from now. Engineering for the AI-Native Law Firm: a discussion with Javed Qadrud-Din, CTO and Co-Founder of General Legal Timestamps: 00:00 - Why legal training can make you a better technologist 00:24 - Meet Javed Qadrud-Din, co-founder and CTO of General Legal 03:04 - From corporate law to building AI 06:42 - Building some of the earliest deep learning tools for legal research 09:35 - The breakthrough that made semantic legal search possible 11:31 - The engineering philosophy behind General Legal 12:27 - Why lawyers still review every piece of AI-generated legal work 13:45 - What General Legal builds in-house, and why 15:28 - How AI is changing the way engineers write code 16:14 - Why AI is better at coding than legal work 17:39 - What legal work will AI actually be able to replace? 18:08 - Why law firms’ private data matters for AI 18:55 - Building AI that learns from real-world legal outcomes 19:46 - Counsel in 60 - High-speed Q&A 20:50 - Where AI and law could be in five years “Everything goes through a lawyer. You will never be getting AI output from us directly.” Check out General Legal at https://general.legal/ (https://general.legal/)

8. 

   29 Sept 2026

   What is Great Lawyering in the AI Era? | Dan Sito, Tax Partner at General Legal Great Lawyering in the AI Era | Dan Sito, Tax Partner at General Legal

   The role of the lawyer is evolving. Katrina Barry sits down with Dan Sito, Tax Partner at General Legal, for an episode of Well Counseled exploring what it means to be an excellent lawyer in the age of AI. From corporate tax law to software engineering, product development, and design, Dan shares how his pursuit of becoming a better lawyer has led him to develop skills far beyond traditional legal practice. In this episode, Dan discusses how large language models and coding agents are expanding what lawyers can accomplish, why substantive expertise and strong client relationships remain essential, and how technology can help attorneys communicate complex legal concepts more effectively. He also shares his approach to continuous learning, the importance of critical thinking, and why he sees AI as an opportunity to strengthen, rather than replace, professional judgment. What is Great Lawyering in the AI Era? | Dan Sito, Tax Partner at General Legal 00:00 - Can AI make lawyers better, or will it weaken critical thinking? 00:20 - Meet Dan Sito, Tax Partner at General Legal 01:21 - Dan's path into tax law and what makes a great transactional lawyer 03:43 - What corporate tax lawyers actually do 06:04 - From practicing tax law to experimenting with technology 08:50 - How AI and coding agents expand lawyers' capabilities 10:18 - What happens when everyone has access to AI-powered expertise? 13:07 - Measuring better lawyering 15:02 - Legal design and creating better client experiences 19:26 - The challenges of AI-generated legal writing 20:10 - Using AI without sacrificing accuracy and critical thinking 23:10 - Why great lawyers need to keep expanding their skills 26:01 - When are traditional methods still preferable? 29:46 - Advice for young attorneys learning to work with AI 30:35 - Counsel in 60: Rapid-fire questions 33:12 - Dan's closing advice: Expect more of yourself “Challenge yourself to do the things that you would say you couldn't do before.” Check out General Legal at https://general.legal/ (https://general.legal/)

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Guest appearances

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Based on episode analysis; this does not confirm that the show is currently accepting guests.