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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What happens when one of the original voices in solo law practice meets the cutting edge of AI?
At 8AM’s Kaleidoscope event, Brian sat down with Carolyn Elefant - legendary founder of MyShingle, author of Solo by Choice, and environmental justice attorney fighting Big Energy with bold strategy and even bolder tech.
In this conversation, Carolyn shares how she:
- Turned a dot-com-era blog into a pipeline for high-value clients
- Uses AI to decode 200-page rulings in minutes (and train new lawyers fast)
- Created a playbook so effective, government agencies distributed it for her
- Is building an AI-first law firm offshoot with scalability in mind
This isn’t your average solo practice story. It’s a deep dive into how to work smarter, build authority, and design a law firm that actually fits your life — not the other way around.
Whether you’re solo-curious, tech-savvy, or just sick of the billable grind, this episode will make you rethink what’s possible.
Hit play and get inspired by Carolyn’s unapologetic, future-facing approach to law.
Connect with Carolyn:
www.myshingle.com
LinkedIn: https://www.linkedin.com/in/carolynelefant/
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Brian Glass is a nationally recognized personal injury lawyer in Fairfax, Virginia. He is passionate about living a life of his own design and looking for answers to solutions outside of the legal field. This podcast is his effort to share that passion with others.
Want to connect with Brian?
Follow Brian on Instagram: @thebrianglass
Connect on LinkedIn
Chapters
1. Live Kaleidoscope kickoff (00:00:00)
2. Origin of MyShingle and early blogging (00:01:15)
3. Niche practice: climate and communities (00:02:45)
4. The guide that marketed itself (00:03:50)
5. Giving away value, earning trust (00:06:10)
6. Dynamic staffing and long-term VA (00:07:40)
7. How AI levels skills and speed (00:08:40)
8. Deep research, sourcing, and safeguards (00:10:05)
9. Process, projects, and custom workflows (00:12:05)
10. Privacy, redaction, and uploads (00:13:45)
11. Efficiency, pricing, and volume strategy (00:15:00)
12. Marketing with AI in real time (00:16:40)
13. Building an AI-forward spin-off firm (00:17:50)
14. The future of legal niches and tech (00:19:10)
15. Conferences, community, staying fresh (00:20:10)
16. Closing reflections and thanks (00:21:00)
242 episodes
