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

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