How Financial Advisors Can Help Clients Understand What is Actually Happening in Their Portfolios
“We’re not just translating numbers. We’re giving advisors the language to deliver real, human conversations at scale.” – Justin Whitehead, CEO of Pebble Finance
In this episode of the Modern Financial Advisor Podcast, Mike Langford welcomes Justin Whitehead, Co-Founder and CEO of Pebble Finance, to explore how AI is fundamentally transforming client communication in wealth management.
Forget the hype. While many firms are still slapping “AI-powered” labels onto basic automation tools, Pebble is quietly redefining one of the most important—and often overlooked—aspects of the advisor-client relationship: communication.
Justin’s story begins with a moment every investor can relate to: a well-intentioned but poorly informed decision to diversify into Chinese markets… followed by silence from his advisor and a sharp market downturn. That experience, and his background in building portfolio analytics tools at FactSet, sparked a question that now sits at the heart of Pebble:
Why is it still so hard for advisors to clearly explain what’s happening in a client’s portfolio?
Why Portfolio Conversations Are Broken (And How Pebble Fixes Them)
Modern portfolios are complex. Clients are overwhelmed by jargon. Advisors are stretched thin. And yet, the expectation for personalization and clarity has never been higher—especially among younger, self-directed investors who grew up with Robinhood, Reddit, and real-time market commentary.
Pebble Finance solves this by combining deep portfolio math with AI-powered content generation to create real-world narratives that advisors can use immediately.
Think:
✅ Contextual explanations for market shifts
✅ Client-ready commentary in plain English
✅ Custom newsletters at scale
✅ All without touching PII or raising red flags with compliance
As Justin puts it:
“We’re enabling advisors to speak their clients’ language—quickly, accurately, and at scale—without having to sacrifice compliance or credibility.”
What This Means for Financial Advisors
For financial advisors, Pebble isn’t just another dashboard. It’s a conversation engine.
Imagine being able to instantly generate timely, portfolio-specific commentary that references what your client read in the Wall Street Journal yesterday or what they just asked you about over email. Or sending a personalized newsletter that highlights what’s driving returns in their portfolio—without spending hours researching or writing.
Now you can.
More touchpoints. Better conversations. Lower churn. That’s the promise of Pebble—and it’s one that couldn’t be more timely as advisory firms face increasing pressure to scale personalization without adding headcount.
Related Episodes You Might Enjoy
🎧 Behavioral Portfolio Management with Felipe Toews
In this episode, Felipe Toews, CEO of Toews Asset Management, explores how honest communication and scenario planning can deepen client trust. A perfect companion to today’s conversation on AI and behavioral finance.
➡️ Listen & Read the Episode Recap
🎧 Arnim Holzer on Macro Risk and Client Conversations
Another great episode for advisors who want to make market risk relevant and understandable for clients. Learn how to frame global macro events in ways that actually resonate.
Want to Stay Relevant in the AI Era of Wealth Management?
If you’re an executive at a wealth management firm or a FinTech provider looking to empower advisors with scalable, high-quality client communication—Pebble deserves a look. This is the type of innovation that will define the next generation of advisory excellence.
