Summary

Tune into "Adventures in Legaltech" for an engaging talk with Caspar Roxburgh, GM of Draftable. Discover how to tackle the infamous Word doc track changes mishap, get insights on law firm tech overload solutions, and explore fresh paths in legal technology innovation. 📄🎙️.

Episode Highlights

00:05:45 - Introduction to Colin's vexing problem: missing track changes.

00:07:44 -Options for document comparison in legal tech.

00:10:18 - Caspar's transition from product team to general management.

00:13:43 - The importance of customer feedback in product development.

00:16:40 - Caspar's unexpected journey from agriculture to legal tech.

00:19:57 - Tech overload in law firms and renewal cycles explained.

00:24:58 - Balancing off-the-shelf solutions versus building bespoke tools.

00:28:35 - Navigating pricing and honest cost structures in legal software.

Episode Resources

Resources mentioned in the podcast:

www.redcavelegal.com

www.draftable.com

Binge Thinking

Keywords

• Adventures in Legaltech

• Legaltech conversations

• Technology issues

• Law practice technology

• Red Cave Law Firm Consulting

• Legal software solutions

• Document comparison software

• Draftable

• Legal tech commentary

• Real estate, banking, finance, M&A

• Podcast professional

• Vibe coding

• AI in legal tech

• Vendor-law firm relationship

• Legal tech automation

• Law firm tech overload

• Software renewal cycles

• Legal tech pricing

• AI technology features

I spoke with a solo attorney, who gets a heck of a lot done in her unique practice niche, by leveraging AI + business planning.

Episode Highlights

02:12 - Overwhelming AI solutions in law.

03:56 - Jess Birken recommends note-taking AI.

04:48 - Fathom: AI for virtual meetings.

06:31 - Flat fees vs. hourly billing for AI efficiency.

07:25 - AI in competitive practice areas.

08:55 - Using AI for marketing in law.

12:50 - The rise of podcasting for marketing.

16:05 - Transition to nonprofit law.

18:41 - Vetting AI tools for legal use.

21:00 - Balancing innovation with caution in AI.

23:48 - Prioritizing intentions over rigid plans.

Episode Resources

• Connect with Jared Correia

• [email protected]

• https://redcavelegal.com/

• https://www.linkedin.com/in/jaredcorreia

• https://twitter.com/RedCaveLegal

• www.linkedin.com/in/jaredcorreia/

• Connect with Jess Birken

• https://birkenlaw.com/

• [email protected]

I talked with an attorney who owns a law firm and real estate closing company about how he grew his organizations using acquisition as a tool, as well as about how the firm has stayed on track by adopting modern technology.

Episode Highlights

01:04 - Commitment to actionable insights.

02:05 - Creating a fun workplace culture.

06:22 - Impact of culture and dynamics.

07:39 - Using unexpected initiatives.

10:57 - Decision-making and organizational charts.

13:35 - Featuring the human side of business with events.

17:33 - Approach to business and acquisitions.

19:12 - Opportunities in legal and closing business models.

27:17 - Decision on adopting Qualia for business.

31:43 - Using AI in legal practices.

34:35 - Future for lawyers in AI integration.

Episode Resources

• Connect with Jared Correia

• [email protected]

• https://redcavelegal.com/

• https://www.linkedin.com/in/jaredcorreia

• https://twitter.com/RedCaveLegal

• www.linkedin.com/in/jaredcorreia/

• Connect with Jack O'Donohue

• https://touchstoneclosing.com/

• https://touchstonelawoffices.com/

• https://www.youtube.com/@DonutDigest

• [email protected]

I spoke with a senior paralegal about best practice tips for intake + client service.

Episode Highlights

02:45 - Automations in CRM to filter conversations.

04:04 - The "CRM as ATM" concept for law firms.

06:13 - The importance of cultural responsiveness in client communication.

07:46 - The value of short, effective intake forms.

11:03 - Benefits of outsourcing roles in firms.

12:56 - Effective use of answering services.

16:13 - Importance of metrics and lead tracking.

19:45 - Training clients for law firm communication expectations.

22:15 - Simplifying software usage in law firms.

25:01 - Exploring artificial intelligence in legal practices.

Episode Resources

• Connect with Jared Correia

• [email protected]

• https://redcavelegal.com/

• https://www.linkedin.com/in/jaredcorreia

• https://twitter.com/RedCaveLegal

• www.linkedin.com/in/jaredcorreia/

• Connect with Vanessa Reynolds

• gmrodriguezlaw.com

• [email protected]

I spoke with a lawyer, developer, educator & data scientist about how AI is disrupting law practice & legal education.

Episode Highlights

03:33 - AI revolution challenge for law firms.

05:57 - What is agentic AI?

11:41 - Custom GPTs in practice.

19:52 - Bias in AI and its implications.

25:52 - Tackling AI fairness and justice.

32:57 - Star Trek's predictive view on AI.

36:01 - The concept of P-Doom.

45:20 - Role-playing in AI and law education.

48:30 - The promise of AI in education.

54:41 - Legal students' interaction with AI tools.

Episode Resources

• Connect with Jared Correia

• [email protected]

• https://redcavelegal.com/

• https://www.linkedin.com/in/jaredcorreia

• https://twitter.com/RedCaveLegal

• www.linkedin.com/in/jaredcorreia/

• Connect with David Colarusso

• https://suffolklitlab.org/

• https://lawrpg.org/

• [email protected]

I spoke with Jordan Furlong, of Law21, a legal futurist, about what impact AI is having (and, will have) on lawyers.

Episode Highlights

04:51 - Large language models and ChatGPT in law.

05:39 - General-purpose technology's ubiquity.

07:39 - The empowerment potential of AI.

09:57 - Rethinking legal tasks and roles.

16:59 - AI adoption in law firms: Challenges and opportunities.

19:04 - Billable hours and changing legal pricing.

37:11 - Law21 consulting focus: Adaptation in legal services.

39:59 - The need for legal industry transformation.

54:12 - Reflecting on societal and historical responsibilities.

Episode Resources

• Connect with Jared Correia

• [email protected]

• https://redcavelegal.com/

• https://www.linkedin.com/in/jaredcorreia

• https://twitter.com/RedCaveLegal

• www.linkedin.com/in/jaredcorreia/

• Connect with Jordan Furlong

• [email protected]

• https://www.law21.ca/

I spoke with a consultant who builds document automation tools for private law firms & legal aid agencies, among others.

Episode Highlights

01:21 - Problem of slow document generation.

03:10 - Automating documents with DocAssemble.

07:11 - Open source vs. commercial software.

08:52 - Potential and barriers of document automation.

11:01 - Challenges in automating complex documents.

12:02 - Logic and formatting complexity.

14:09 - Customization in legal tech.

15:51 - Impact of budget cuts on Legal Services Corporation.

16:52 - Legal aid's critical role for community stability.

18:56 - AI's impact on the legal intake process.

20:14 - AI tools for legal outreach.

22:16 - Environmental concerns regarding AI.

23:52 - Upcoming legal innovation conference in Boston.

Episode Resources

• Connect with Jared Correia

• [email protected]

• https://redcavelegal.com/

• https://www.linkedin.com/in/jaredcorreia

• https://twitter.com/RedCaveLegal

• www.linkedin.com/in/jaredcorreia/

• Connect with Quinten Steenhuis

• https://lemmalegal.com/

• https://suffolklitlab.org/

• [email protected]

I spoke to a member of a legaltech implementation & customization firm - the former owner & the new owner, as we spoke about the state of legal software & AI.

Episode Highlights

03:29 - Donna and Jackie offer tech solutions.

04:01 - Importance of customized tech stacks.

06:01 - Evolution from limited to vast legal tech.

09:17 - Jackie on internal transitions and recruitment.

11:48 - The growing allure of Oklahoma City.

14:44 - Shift towards alternative legal billing.

20:51 - AI's role in law firm billing discussions.

25:15 - Automation's impact on billing approvals.

29:37 - Consolidation trends in Legal Tech.

Episode Resources

• Connect with Jared Correia

• [email protected]

• https://redcavelegal.com/

• https://www.linkedin.com/in/jaredcorreia

• https://twitter.com/RedCaveLegal

• www.linkedin.com/in/jaredcorreia/

• Connect with Donna Brown and Jaclyn McDuffey

• https://www.beyondsquareone.com/

I spoke with a business attorney who works for corporations and handles crisis litigation about his practice.

Episode Highlights

03:06 - Importance of technology in managing court deadlines.

06:43 - Evolution and significance of docket calendaring.

08:52 - Insights into selecting travel bags for lawyers.

09:36 - Recommendations for travel gadgets and mice.

10:28 - Sports memorabilia collecting insights.

12:07 - Favorite sports memorabilia pieces.

14:05 - Concept of crisis litigation explained.

17:11 - Handling chaotic legal situations.

19:07 - Working with corporations and honest communication.

21:37 - Key to maintaining lawyer-client relationships.

23:14 - Personal management style advice for lawyers.

Episode Resources

• Connect with Jared Correia

• [email protected]

• https://redcavelegal.com/

• https://www.linkedin.com/in/jaredcorreia

• https://twitter.com/RedCaveLegal

• www.linkedin.com/in/jaredcorreia/

• Connect with Adam Hersh

• https://bluechip.law/ourteam/adam-hersh/

I talked with my guest about adopting and managing legal technology with an eye toward law firm ethics.

Episode Highlights

03:51 - Essential Legal Tech Tools

06:00 - Vendor Partnership Program at alps

06:51 - Wire Fraud and Its Risks

07:59 - Deepfake Scams in Transactions

09:23 - Technology Integration Challenges

10:05 - Importance of Tech Training

13:23 - Tech Adoption Barriers for Lawyers

15:28 - Vetting Tech Vendors for Security

18:11 - Younger Lawyers and Tech Challenges

19:29 - Importance of Processes and Workflows

20:47 - Vetting Software for Risk Reduction

25:51 - Selecting Malpractice Insurance

27:59 - Necessity of Cyber Insurance

Episode Resources

• Connect with Jared Correia

• [email protected]

• https://redcavelegal.com/

• https://www.linkedin.com/in/jaredcorreia

• https://twitter.com/RedCaveLegal

• www.linkedin.com/in/jaredcorreia/

• Connect with Rio Laine

• https://www.alpsinsurance.com/