Casey Riggs

Casey Riggs – How Entrepreneurs Can Identify Business Problems and Make Informed Decisions

Casey Riggs is a Member of Riggs Davie PLC, a boutique law firm specializing in corporate and securities law, mergers and acquisitions, venture capital/private equity, and estate and tax planning. In his practice, he focuses on estate planning, including wills, trusts, powers of attorney, and health care directives for individuals and families. Casey also advises clients on corporate matters such as entity formation, financing, equity compensation, and mergers and acquisitions.

Here's a Glimpse of What You'll Learn

[1:24] How Casey Riggs joined EO after starting his law firm — and why he left a traditional firm
[5:49] Common misconceptions about working with lawyers
[7:02] Personality traits Casey observes in entrepreneurs
[8:50] How EO influenced Casey’s leadership style and risk-taking pursuits
[10:02] Casey’s toughest firm decisions, including letting employees go
[14:00] The impact of AI on Casey’s legal work and productivity
[27:02] Why ideal client referrals outperform search-based inbound leads
[29:11] Casey’s personal career plans and approach to scaling his firm

In This Episode

Entrepreneurs can struggle to define the underlying problem behind the urgent issue they bring to advisors. Questions get buried under assumptions, and complex challenges get reduced to overly simple requests. Uncovering the actual problem can be one of the most valuable skills a business owner develops.

According to business attorney Casey Riggs, clarity is the starting point for every effective solution. He recommends digging past the surface by asking targeted questions and resisting the urge to fix what hasn’t been fully defined. Casey also emphasizes the importance of working with people familiar with professional processes and leveraging AI tools to improve accuracy, efficiency, and decision-making.

In this episode of The Decision, Robert Hartline and Eric Jackson chat with Casey Riggs, a Member of Riggs Davie PLC, about identifying client needs. Casey shares how he diagnoses core issues, how EO shaped his leadership style, and how AI is transforming his legal work.

Quotable Moments:

“I think figuring out what the real problem is is always a challenge.”
“I didn’t know what that thing would be, but I wanted to sort of… own something, run something, control something.”
“Entrepreneurs are aggressive… they’re risk takers.”
“I think the AI stuff’s been life-changing. I mean, in the last year, I feel like my practice has changed dramatically.”
“It’s fun to talk to someone and solve their problem — doesn’t matter what their problem is.”

Action Steps:

Clarify the real problem before acting: Taking time to uncover root issues prevents wasted effort and misguided decisions. A clear understanding leads to more targeted solutions and better outcomes.
Work with professionals who understand your needs: Experienced advisors reduce friction and improve collaboration. Their familiarity with complex processes helps you avoid costly mistakes.
Build a team with strong attention to detail: Precision in execution prevents errors that compound into bigger problems. Detail-oriented team members also lighten the workload for leaders and partners.
Leverage AI tools to streamline tedious tasks: Automating drafting and research frees you to focus on higher-value strategic work. Using the right tools also improves accuracy and accelerates decision-making.
Keep learning and experimenting with new technologies: Rapid change rewards those who continually adapt. Staying curious ensures you remain competitive and ready for emerging opportunities.