Planning & Beyond® - Where financial planning meets human understanding

62. AI and Client Connection with Gabe Caldwell

Ashley Quamme

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What if AI helped advisors become more human, not less?

In this episode of Planning & Beyond®, Ashley talks with Gabe Caldwell, co-founder of Quin, about how technology can help financial advisors get time, energy, and attention back.

Gabe explains that the best use of AI is not simply writing LinkedIn posts or brainstorming ideas. For advisors, the bigger opportunity is using AI to handle the routine work that often eats up the week: meeting prep, notes, follow-up emails, CRM updates, scheduling, and client communication.

Ashley and Gabe discuss the reality that many advisors are spending about 22 hours a week on admin work, and what changes when some of that load comes off their plate. Gabe shares how reducing admin work can help advisors sleep better, feel less rushed, show up with more energy, and be more present in client meetings.

They also talk about the concerns many advisors have around AI, including control, compliance, privacy, and whether technology could weaken the client relationship. Gabe explains why good AI tools should keep the advisor involved, especially when client communication is being drafted or sent.

Episode Highlights:

  • How Gabe’s earlier business experiences shaped the creation of Quin
  • Why AI should help advisors get time back, not just do more work
  • How admin tasks affect advisor presence and client relationships
  • Why reducing mental load can improve how advisors show up in meetings
  • Common concerns about AI, control, compliance, and client trust
  • Why human review still matters when using AI tools
  • How advisors can use technology to support the work they actually enjoy

This conversation is especially useful for advisors who want to use AI thoughtfully, reduce routine admin work, and create more space for the human side of financial planning.

RESOURCES AND GUEST INFORMATION

Gabe Caldwell is co-founder of Quin, an AI assistant for financial advisors and other relationship professionals. Quin helps with routine work such as meeting prep, note capture, email drafts, CRM updates, scheduling, and client communication through tools like SMS, email, voice, Slack, and Teams. Advisors using Quin save 5 to 15 hours per week by offloading routine admin work.

Gabe is also a co-founder of Plain Sight Ventures, where he and his team have built and scaled multiple software companies to millions of users over the past 10 years. His work focuses on helping professionals automate the tasks that slow them down so they can spend more time on relationships.

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