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

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

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

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

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

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

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

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