The Redline The Morning Show for Lawyers Who ❤️ AI https://the-redline.beehiiv.com/ en © 2026 2025 019dc4c0-56ea-7155-bfba-e46e8d3d4f55 no podcast https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80/uploads/asset/file/bacdf0e7-a43c-4ad4-afff-641629c9bc4d/Untitled_design__29_.png?t=1782153381 The Redline https://the-redline.beehiiv.com/ false episodic Mike Whelan The Morning Show for Lawyers Who ❤️ AI

]]> Mike Whelan niko.pajkovic@spellbook.legal Thu, 02 Jul 2026 14:01:22 +0000 Thu, 02 Jul 2026 14:34:18 +0000 beehiiv Everyone's Wrong About AI and Access to Justice | Natalie Knowlton https://the-redline.beehiiv.com/podcast/s/theredline/everyone_s_wrong_about_ai_and_access_to_justice_natalie_knowlton Natalie Knowlton has spent 20 years working on what everyone in legal calls "access to justice", a phrase she calls "the buzzword to end all buzzwords." Now as the Associate Director of Legal Innovation at the Center on the Legal Profession at Stanford... Thu, 02 Jul 2026 14:01:22 +0000 1374 Mike Whelan false full Natalie Knowlton has spent 20 years working on what everyone in legal calls "access to justice", a phrase she calls "the buzzword to end all buzzwords."

Now as the Associate Director of Legal Innovation at the Center on the Legal Profession at Stanford, she's focused on civil justice reform, family court, and the middle-market clients most lawyers forget are locked out too.

During this conversation, Mike and Natalie discuss what AI can and can't do for access, why self-help isn't the fix everyone wants it to be, why the adversarial system was already broken before ChatGPT showed up, and what practitioners themselves would have to change for anything to actually improve.

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:
Get the latest news, trends, and tactics in legal AI—straight to your inbox.
➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:
Draft and review contracts 10x faster
➞ try it free: https://www.spellbook.legal

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁:
https://www.linkedin.com/in/natalieanneknowlton/
Bluesky/X: natalalleycat

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝗠𝗶𝗸𝗲 𝗪𝗵𝗲𝗹𝗮𝗻:
https://www.linkedin.com/in/mikewhelanjr/

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:
0:00 - Introduction
0:37 - Meet Natalie Knowlton
1:07 - What "access to justice" actually means
6:07 - Self-help and its limits
7:23 - Why pro se filings are flooding the courts
9:37 - The three functions of lawyers and where AI fit
10:46 - AI in the adversarial system
13:13 - The emotional good of being seen and heard
14:16 - The Nippon Life / OpenAI case
15:37 - Law as a credence good problem
16:41 - Small legal AI vs. big general AI on accountability
18:30 - Regulation and the trust vs. capability question
20:03 - What practitioners need to do next
22:11 - Bottlenecks surfacing older problems
22:33 - Connect with Natalie

]]> Why Every Legal Team is About to Be Restructured with Alex Su (Latitude Legal) https://the-redline.beehiiv.com/podcast/s/theredline/why_every_legal_team_is_about_to_be_restructured_with_alex_su_latitude_legal Alex Su talks to the people who hire lawyers. As Chief Revenue Officer at Latitude, an alternative legal services provider that builds on-demand teams for firms and in-house departments, he sees the resourcing decisions, the AI pressure, and the trade-... Mon, 15 Jun 2026 17:46:57 +0000 1597 Mike Whelan false full Alex Su talks to the people who hire lawyers. As Chief Revenue Officer at Latitude, an alternative legal services provider that builds on-demand teams for firms and in-house departments, he sees the resourcing decisions, the AI pressure, and the trade-offs play out in real time.

During our conversation, we spoke about why in-house teams keep growing, why "judgment" isn't something you type into a chatbot, and what lawyers need to underline when their bosses ask what humans still do.

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝘀𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗔𝗜 𝗶𝗻 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲:

Spotify: https://open.spotify.com/show/1RqIrtq...
Apple: https://podcasts.apple.com/us/podcast...

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁:

https://www.linkedin.com/in/alexander-su/
https://www.alexofftherecord.com/

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:
Get the latest news, trends, and tactics in legal AI—straight to your inbox.

➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:
Draft and review contracts 10x faster

➞ try it free: https://www.spellbook.legal

]]> The Client Side of Legal AI with Hilary Bowman https://the-redline.beehiiv.com/podcast/s/theredline/the_client_side_of_legal_ai_with_hilary_bowman Hilary Bowman built Querious to solve the most frustrating moment in legal practice - when something unexpected comes up in a client meeting and the lawyer has to say "let me research and follow up." After more than a decade as a healthcare attorney at... Thu, 28 May 2026 14:46:44 +0000 1376 Mike Whelan false full Hilary Bowman built Querious to solve the most frustrating moment in legal practice - when something unexpected comes up in a client meeting and the lawyer has to say "let me research and follow up."

After more than a decade as a healthcare attorney at law firms and in-house at enterprises like IBM, she founded Querious to sit inside attorney-client conversations on Zoom, Teams, or phone and surface issues, questions, and follow-ups in real time.

In this conversation, she flips the usual AI for lawyers script and asks what these tools actually do for clients - why most clients want a relationship partner instead of a black box, why timely follow-ups beat fancy portals, and how language tools finally let lawyers meet clients where they are.

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁:

https://www.linkedin.com/in/hilarybowman/
https://www.querious.ai/

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction
0:50 - Meet Hilary
2:03 - What Querious does in a client meeting
2:45 - From healthcare law to founding a startup
4:10 - What clients actually want from a lawyer
5:21 - The lawyer as relationship partner and traffic cop
6:55 - The black box problem of hourly billing
7:30 - Bridging asymmetries between lawyer and client
8:03 - Why law can't have a Domino's Pizza tracker
10:36 - The most powerful LLM unlock for clients
12:38 - Where AI ends and creative lawyering begins
14:22 - Change costs and tool adoption
15:55 - Speed to value: narrowing the scope
17:45 - Building feedback loops with clients
20:18 - One thing to implement on Monday
22:15 - Connect with Hilary

]]> Why AI Won't Fix Your Broken Workflow with John Grant https://the-redline.beehiiv.com/podcast/s/theredline/why_ai_won_t_fix_your_broken_workflow_with_john_grant AI tools won't solve your overwhelm if your processes are the problem. John Grant is a fourth-generation lawyer turned workflow consultant. He spent a decade in tech before practicing law, and another eleven years helping firms fix how work actually mo... Thu, 14 May 2026 00:19:21 +0000 1565 Mike Whelan false full AI tools won't solve your overwhelm if your processes are the problem. John Grant is a fourth-generation lawyer turned workflow consultant. He spent a decade in tech before practicing law, and another eleven years helping firms fix how work actually moves. In this conversation, he breaks down the "magical thinking" behind AI adoption, why the real bottleneck is almost never where lawyers think it is, and how speeding up the wrong step actually makes everything worse. He also explains the concepts of "definition of done" and "definition of ready," why legal has an immature relationship with quality assurance, and what courts are already seeing as AI-assisted filings flood systems that aren't built to handle them.

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁:

https://www.linkedin.com/in/johnegrant/
https://agileattorney.com https://greenlinelegal.com

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox.

➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster

➞ try it free: https://www.spellbook.legal

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction
0:42 - Meet John Grant
2:13 - What is Greenline?
3:18 - AI hasn't reduced work
4:30 - The optimism bias and the planning fallacy
6:00 - AI and the last mile problem
7:09 - Output vs. productivity: the developer study
8:06 - Effort is not value
9:21 - Reimagining what value actually means
10:00 - There's only one bottleneck
11:16 - Why improving the wrong step makes things worse
12:10 - AI-assisted pro se filings are flooding courts
13:45 - More but worse vs. less but better
14:00 - Where bottlenecks actually form in legal
15:27 - Legal's immature relationship with quality assurance
16:15 - Quality control is chosen friction
17:21 - Definition of done and definition of ready
18:06 - Failure demand and rework
19:29 - Lawyering is a caregiving profession
22:39 - The board game analogy: multiple ways to lose
23:32 - The Agile Attorney 101 podcast series
25:04 - Takeaway: AI won't solve overwhelm without design
25:38 - Connect with John

]]> Are AI Notetakers Ethical for Lawyers? with Wendy Meadows & Michael Eisenberg https://the-redline.beehiiv.com/podcast/s/theredline/are_ai_notetakers_ethical_for_lawyers_with_wendy_meadows_michael_eisenberg In this episode, Mike walks through the New York City Bar's recent opinion on using AI to record, transcribe, and summarize client conversations, and boils it down to four duties you probably already follow. Then mediator Wendy Meadows shares her full ... Sat, 25 Apr 2026 13:34:43 +0000 1013 Mike Whelan false full 12 In this episode, Mike walks through the New York City Bar's recent opinion on using AI to record, transcribe, and summarize client conversations, and boils it down to four duties you probably already follow.

Then mediator Wendy Meadows shares her full workflow, including Fathom for capture, Clio for document production, Spellbook for quality control, and how it turned a two-hour MOU into a 20-minute job. Michael Eisenberg breaks down consent rules, one-party vs. two-party states, and why none of this is actually new.

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox.
➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster
➞ try it free: https://www.spellbook.legal

https://www.linkedin.com/company/spellbookai/posts/?feedView=all
https://www.linkedin.com/in/mikewhelanjr/
https://www.linkedin.com/in/scottas/

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:
0:00 - Introduction
1:46 - The New York City Bar opinion (Formal Opinion 20256)
2:45 - Risk 1: Consent and one-party vs. two-party states
4:48 - Risk 2: Confidentiality and ABA Rule 1.6(c)
6:06 - Risk 3: What if the client records the call?
8:46 - Why these rules aren't new
9:05 - Wendy's practice: mediator on Zoom all day
10:00 - Turn off the defaults
10:51 - Using it like an associate
12:27 - Drafting direct examination from a transcript
13:08 - Spellbook as the quality control layer
14:48 - Predicting the future: insights in context
16:01 - Why the good outweighs the bad
16:37 - Connect with Wendy and Michael

]]> How a Business Lawyer Reviews a 56-Page Contract with AI with Chris Brown https://the-redline.beehiiv.com/podcast/s/theredline/how_a_business_lawyer_reviews_a_56-page_contract_with_ai_with_chris_brown Contract review is tedious, but missing something can be expensive. In this episode, Chris Brown of Pixel Law shares his screen as he reviews a 56-page Asset Purchase Agreement using Spellbook. See how effective AI tools can help you: - Surface unknown... Fri, 10 Apr 2026 16:47:00 +0000 1945 Mike Whelan false full 11 Contract review is tedious, but missing something can be expensive.

In this episode, Chris Brown of Pixel Law shares his screen as he reviews a 56-page Asset Purchase Agreement using Spellbook.

See how effective AI tools can help you:

- Surface unknown risks, - Draft clauses like indemnification and delivery terms, and - Update you on substantive legal issues within a contract.

Chris also shares how he uses Spellbook for a "second opinion," and why he believes AI will change the practice of law.

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁:

https://www.linkedin.com/in/thepixellawyer/

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction

0:37 - What contract review looked like before AI

1:52 - The document: a 56-page asset purchase agreement

2:11 - High-level risk overview

4:18 - Diving into indemnification

8:25 - Non-compete analysis and Florida law

10:46 - Breaking down the purchase price

15:08 - Reps and warranties review (35 issues in 9 pages)

17:52 - Running the same prompt twice for a second opinion

18:24 - Closing deliveries and what's missing

22:08 - Catching missing terms across the document

24:44 - Compare to Market feature

28:35 - What stood out most from the process

29:51 - When to trust AI vs. your own judgment

31:00 - How to get started with AI tools

32:09 - Wrap up

]]> Is Your Client's AI Chat Discoverable? with Leslie Bender & Craig Linton https://the-redline.beehiiv.com/podcast/s/theredline/is_your_client_s_ai_chat_discoverable_with_leslie_bender_craig_linton What happens if your client asks ChatGPT for advice about their case? Is that discoverable? Is it your fault if you didn't warn them it might be? Leslie Bender and Craig Linton join the show to unpack two cases: Heppner and Warner v Gilbarco, that seem... Fri, 27 Mar 2026 17:18:00 +0000 2036 Mike Whelan false full 10 What happens if your client asks ChatGPT for advice about their case? Is that discoverable? Is it your fault if you didn't warn them it might be? Leslie Bender and Craig Linton join the show to unpack two cases: Heppner and Warner v Gilbarco, that seem to reach opposite conclusions as judges try to draw lines around privilege, work product, and AI in an area where the rules haven't caught up to the tools.

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝘀𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗔𝗜 𝗶𝗻 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲:

Spotify: https://open.spotify.com/show/1RqIrtqTgbng2BGuzr4aAq

Apple: https://podcasts.apple.com/us/podcast/ai-in-practice/id1846506529

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁𝘀:

https://www.linkedin.com/in/lescbender/

https://www.linkedin.com/in/craigalinton/

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox.

➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster

➞ try it free: https://www.spellbook.legal

https://www.linkedin.com/company/spellbookai/posts/?feedView=all

https://www.linkedin.com/in/mikewhelanjr/

https://www.linkedin.com/in/scottas/

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction

1:49 - Meet Leslie Bender 2:31 - Meet Craig Linton

3:31 - Attorney-client privilege and work product 101

5:54 - Clients have always gone rogue with case info

8:00 - The Heppner case: a CEO, AI, and a 31-point memo

11:21 - Does it matter if the lawyer directed it?

13:00 - Warner v Gilbarco: the pro se counterpoint

16:08 - What discoverability means for pro se litigants

19:21 - Assume your AI self-help is discoverable

21:37 - The engagement letter hack

23:19 - Should we encourage or discourage client AI use?

25:06 - Lawyers as AI consumers: is Claude enough?

28:10 - Reasonable privacy expectations vs. the fine print

30:49 - Three predictions for the next 10 years

33:06 - Connect with Leslie and Craig

]]> How to Run a Law Firm Like a Tech Startup with Kyle Westaway https://the-redline.beehiiv.com/podcast/s/theredline/how_to_run_a_law_firm_like_a_tech_startup_with_kyle_westaway Kyle Westaway has run his firm for 17 years without ever tracking a billable hour. In this conversation, he breaks down why he believes 75% of a lawyer's value has nothing to do with documents—and why that makes AI a tailwind, not a threat, for firms b... Thu, 22 Jan 2026 11:00:00 +0000 1481 Mike Whelan false full Kyle Westaway has run his firm for 17 years without ever tracking a billable hour. In this conversation, he breaks down why he believes 75% of a lawyer's value has nothing to do with documents—and why that makes AI a tailwind, not a threat, for firms built around outcomes instead of time. He also shares how he prices work without defaulting to hourly estimates, why clarity with clients takes courage, and what it means to design a law firm from first principles.

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal

https://ca.linkedin.com/company/spellbookai https://www.linkedin.com/in/mikewhelanjr https://ca.linkedin.com/in/scottas

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction 1:14 - Meet Kyle Westaway 2:30 - Starting a firm fresh out of law school 4:00 - Designing a firm for startups from first principles 5:00 - What do lawyers actually sell? 7:00 - Why the billable hour persists 10:45 - Flat fees only: How Kyle prices work 13:00 - Why clarity with clients takes courage 15:00 - Why they've never tracked a single hour 17:00 - The "market for lemons" problem in legal 19:30 - Why AI helps flat-fee firms (and hurts hourly ones) 22:00 - Purpose and the future of law practice 23:30 - Connect with Kyle

]]> How to Build a Subscription-Based Law Practice Fueled by AI with Ryan Juliano https://the-redline.beehiiv.com/podcast/s/theredline/how_to_build_a_subscription-based_law_practice_fueled_by_ai_with_ryan_juliano Ryan Juliano runs Darwin Legal, a subscription-based fractional general counsel practice serving early-stage tech startups. After 15 years moving down the legal food chain from IPOs to pre-seed companies, he's built a model that replaces the crushing w... Thu, 11 Dec 2025 10:00:00 +0000 2093 Mike Whelan false full 8 Ryan Juliano runs Darwin Legal, a subscription-based fractional general counsel practice serving early-stage tech startups. After 15 years moving down the legal food chain from IPOs to pre-seed companies, he's built a model that replaces the crushing wave of hourly billing with committed capacity—and he's using AI across every part of his practice. In this conversation, he shares what it means to use tools "promiscuously," why lawyers need to get comfortable chopping with blunt axes, and how AI helps him think through not just legal problems but business model design.

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁:

https://www.linkedin.com/in/ryan-juliano-b3833124 https://darwinlegal.com/

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction

1:12 - Meet Ryan Juliano

2:15 - From IPOs to early-stage startups

5:34 - The subscription fractional GC model

8:34 - Who manages legal before you arrive

11:01 - Running everything through AI

16:19 - Good enough vs. perfect

17:55 - Will tools consolidate or stay fragmented?

20:29 - How Ryan spends his time now

24:37 - Shifting from inputs to outputs

27:23 - Capturing knowledge to repurpose

32:57 - Defining "good enough" in legal services

34:04 - Connect with Ryan

]]> Why AI Is Stalled At Your Firm (And How to Fix It) with Colin Lachance https://the-redline.beehiiv.com/podcast/s/theredline/why_ai_is_stalled_at_your_firm_and_how_to_fix_it_with_colin_lachance Colin Lachance helps law firms implement AI without the paralysis. As founder of LawQi and former Innovator in Residence at the Ontario Bar Association, he's developed a practical framework: start with tasks, not processes. In this conversation, he exp... Thu, 27 Nov 2025 11:00:00 +0000 1491 Mike Whelan false full 7 Colin Lachance helps law firms implement AI without the paralysis. As founder of LawQi and former Innovator in Residence at the Ontario Bar Association, he's developed a practical framework: start with tasks, not processes. In this conversation, he explains why most firms aren't ready for full process redesigns, what infrastructure you actually need before experimenting, and how to build the skills that prevent expensive mistakes.

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁:

https://www.linkedin.com/in/colinlachance https://lawqi.com/

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction 1:30 - Meet Colin Lachance 4:15 - Working inside a real law firm 6:00 - The messy garage problem 11:30 - Tasks vs. processes: which comes first 14:00 - What infrastructure you actually need 17:30 - Why start with tasks, not whole processes 21:30 - How lawyers should learn AI 24:15 - Connect with Colin

]]> Using AI to Compete with BigLaw: The Small Firm Playbook w/ Shavon J. Smith https://the-redline.beehiiv.com/podcast/s/theredline/using_ai_to_compete_with_biglaw_the_small_firm_playbook_w_shavon_j_smith Washington, DC attorney Shavon J. Smith runs a small firm that serves growing businesses as their fractional general counsel. In this episode, she explains how AI helps her compete with larger firms – from mapping workflows to drafting contract checkli... Thu, 20 Nov 2025 10:00:00 +0000 1596 Mike Whelan false full 6 Washington, DC attorney Shavon J. Smith runs a small firm that serves growing businesses as their fractional general counsel. In this episode, she explains how AI helps her compete with larger firms – from mapping workflows to drafting contract checklists, improving client alerts, pressure-testing assumptions, and crafting clearer redline comments during negotiations. She also shares where AI meaningfully improves efficiency, where it simply improves quality, and where human judgment still matters most, especially in negotiation and client counseling. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction 2:15 - Meet Shavon J. Smith 3:32 - What is fractional general counsel? 4:00 - AI for process mapping and improvement 6:03 - Using AI as a brainstorming partner 7:46 - Marketing and client communication 8:25 - How clients find the firm (including through AI) 10:06 - Email overwhelm and client management 13:12 - AI for contract drafting and review 16:06 - Being a better strategic advisor 18:00 - Understanding clients' businesses 19:48 - Managing people and processes 22:35 - Where AI can't help: settlement psychology 24:17 - Learning from other lawyers 24:35 - Connect with Shavon

]]> AI Readiness: The IT Infrastructure Lawyers Need Before Adopting AI with Olivia Anderson https://the-redline.beehiiv.com/podcast/s/theredline/ai_readiness_the_it_infrastructure_lawyers_need_before_adopting_ai_with_olivia_anderson Olivia Anderson helps law firms build the IT infrastructure they need before adopting AI. As Principal at Framework IT, a managed service provider working with legal practices of all sizes, she's seen what happens when firms rush into AI without the cy... Thu, 13 Nov 2025 10:00:00 +0000 1851 Mike Whelan false full 5 Olivia Anderson helps law firms build the IT infrastructure they need before adopting AI. As Principal at Framework IT, a managed service provider working with legal practices of all sizes, she's seen what happens when firms rush into AI without the cybersecurity foundations in place. In this conversation, she walks through shadow AI, the $5.5 million problem most firms don't know they have, and why managing partners need to own AI governance whether they like it or not. 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:21 - Meet Olivia Anderson 2:11 - Shadow AI and the $5.5M problem 6:09 - IT readiness for solo lawyers 10:16 - Consumer AI vs. legal-specific tools 13:15 - Creating a responsible AI policy 17:22 - Who owns AI governance at your firm 21:45 - Risk tolerance culture in law 28:56 - Quantifying your firm's risk profile 31:00 - Connect with Olivia

]]> AI's Role in the Courtroom with Appellate Lawyer Todd Smith | AI in Practice https://the-redline.beehiiv.com/podcast/s/theredline/ai_s_role_in_the_courtroom_with_appellate_lawyer_todd_smith_ai_in_practice Todd Smith is a board-certified appellate lawyer in Texas who consults with trial teams and handles appeals. In this conversation, he explains how AI tools are changing his work—and where they hit their limits. 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 1... Thu, 06 Nov 2025 10:00:00 +0000 1734 Mike Whelan false full 4 Todd Smith is a board-certified appellate lawyer in Texas who consults with trial teams and handles appeals. In this conversation, he explains how AI tools are changing his work—and where they hit their limits.

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:42 - Todd's appellate practice model 6:10 - AI collaboration challenges 9:15 - Analyzing trial transcripts with AI 14:57 - Finding arguments vs. knowing what to do with them 19:03 - Small data sets and judgment calls 24:50 - Why hourly billing is breaking down 28:04 - Flat fee experiments 31:23 - Marketing as an AI quick win 34:19 - Connect with Todd

]]> How to Build a Law Firm That Runs Without You with Joey Vitale https://the-redline.beehiiv.com/podcast/s/theredline/how_to_build_a_law_firm_that_runs_without_you_with_joey_vitale Before "AI automation" was a buzzword, Joey Vitale built Indie Law to operate without him. That experience—paired with years helping lawyers scale through virtual assistants—turned him into a quiet expert on systems, delegation, and identity. In this e... Fri, 31 Oct 2025 01:08:00 +0000 1807 Mike Whelan false full 3 Before "AI automation" was a buzzword, Joey Vitale built Indie Law to operate without him. That experience—paired with years helping lawyers scale through virtual assistants—turned him into a quiet expert on systems, delegation, and identity. In this episode, he and host Mike Whelan dig into what happens when the work that once defined you starts running itself, and why the real value of a lawyer might have less to do with tasks and more to do with trust.

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal/

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction

2:15 - Why Joey left litigation

5:34 - The crisis that forced systematization

8:27 - Four stages: doer to strategist

14:44 - Managing VAs prepares you for AI

19:42 - Prompting AI effectively

24:15 - 80% right is 100% awesome

32:51 - Redefining lawyer identity

36:20 - Why clients still need attorneys

]]> Teaching Lawyers to Prompt with AI Legal Consultant Alessandra Colaci https://the-redline.beehiiv.com/podcast/s/theredline/teaching_lawyers_to_prompt_with_ai_legal_consultant_alessandra_colaci Alessandra Colaci helps in-house legal teams figure out how to actually use AI—not just talk about it. As the founder of Legal Plus AI and former founding marketer at Harvey, she's spent years teaching lawyers to prompt, experiment, and integrate AI in... Thu, 23 Oct 2025 08:00:00 +0000 1788 Mike Whelan false full 2 Alessandra Colaci helps in-house legal teams figure out how to actually use AI—not just talk about it. As the founder of Legal Plus AI and former founding marketer at Harvey, she's spent years teaching lawyers to prompt, experiment, and integrate AI into their daily work. In this conversation, she breaks down the quick wins that build momentum, the security concerns that keep lawyers up at night, and why most teams need to start smaller than they think. 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:10 - Meet Alessandra Colaci 2:34 - The adoption gap: Strategy vs. reality 3:42 - Micro-learning and experimentation 6:04 - Quick wins 6:54 - Using AI as a thought partner 11:32 - The "prompt library" approach 13:48 - What to try on your own vs. with the team 17:18 - What's real vs. what's fear 22:53 - When courts will catch up to AI as standard practice 24:27 - Learning what works for you 27:34 - Connect with Alessandra

]]> Fixed Fees, AI Experiments, and The Future of Family Law with Beau Atkins https://the-redline.beehiiv.com/podcast/s/theredline/fixed_fees_ai_experiments_and_the_future_of_family_law_with_beau_atkins Beau Atkins runs Evolve Family Law in Saskatchewan, Canada, where he's using AI to reach the 79% of people with legal problems who never hire a lawyer. In this conversation, he shares how he built an AI-assisted tool that guides self-represented client... Wed, 15 Oct 2025 23:50:00 +0000 2080 Mike Whelan false full 1 Beau Atkins runs Evolve Family Law in Saskatchewan, Canada, where he's using AI to reach the 79% of people with legal problems who never hire a lawyer. In this conversation, he shares how he built an AI-assisted tool that guides self-represented clients through court processes — and how he's testing an AI agent to handle intake calls. His end goal? Serve with three lawyers what would normally take 300.

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction 1:14 - Meet Beau Atkins 2:15 - The journey from frustrated lawyer to entrepreneur 5:34 - AI experiments in family law practice 8:27 - Solving the 79% problem 14:44 - Ethics, disclaimers, and hallucinations 19:42 - What clients really want (and don't get) 27:58 - Product design: Flat fees and AI tools 30:25 - Learning from COVID experiments 32:51 - How Beau uses AI today 33:33 - Connect with Beau

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.com

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