By Greg Woolf, AI RegRisk Think Tank
Conversation with a Wealth Industry Leader
Last week I sat down with Mark Casady—former Chairman & CEO of LPL Financial, co-founder of Vestigo Ventures, and six-year FINRA governor to boot—to explore how artificial intelligence is reshaping wealth management. Our discussion ranged from emotionally intelligent advice to fiduciary guardrails, and the vision of an AI-powered advisory firm of the future.
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AI That Makes Advisors More Human
Casady recently spoke on an industry panel where he surprised the room by describing how AI technology can enhance an advisor’s Emotional Quotient, or EQ, which ultimately works better for the end client. He recalled interviews with LPL’s top producers: their edge wasn’t clever products but an ability to meet “the emotional needs of a client, not just the investment needs.” Properly trained models, he argued, can surface those cues early—prompting an advisor to reach out with genuine empathy, not a robo-text.
Lunch Meetings to Digital Doubles
Casady envisions the next leap coming from lifelike AI stand-ins. Client relationship might start over coffee, lunch, or even a round of golf, but AI will “port that same feeling of the human interaction to video interaction.” It’s easy to imagine, especially for millennials and beyond, who have grown up with digital adoption. Advisor productivity will benefit from AI by allowing them to be present in multiple meetings at once while leveraging an almost infinitely scalable digital staff for back-office tasks. “Pretty amazing. Can’t do that today!” he exclaimed.
Institutionalizing Human Knowledge
Putting theory into practice, Vestigo created its own digital double by feeding roughly 100 of its newsletters into ChatGPT. According to Casady, asking for a fresh post “in Mark’s style” produces output that feels 95 percent authentic—tone, humor and even his “grammatically charming” quirks. To better understand how much Large Language Models already know about us, he suggested a quick test by prompting a model with: “What do you know about me?” I tried this and was amazed—if not slightly unnerved—by the depth of professional and personal insight it surfaced. Scaling that to knowing more about your clients becomes a digital colleague that never forgets.
Mind the Talent Gap—It Won’t Be Filled by Humans Alone
Recent wealth management industry research shows why “virtual human” capability matters. McKinsey projects a shortfall of roughly 100,000 U.S. financial advisors by 2034 if productivity stays flat (McKinsey & Company). Casady says the demand gap is even larger: “We probably need double or triple today’s 300,000-advisor base,” he told me, noting that AI could let one practitioner “do double, triple, quadruple the number of accounts” without sacrificing service quality. The implication is clear—much of the unmet capacity will be absorbed by AI-driven “virtual humans,” not by new employee headcount. Advisors assuming the shortage guarantees job security may be in for a surprise: the net number of human roles could actually decline as scalable digital colleagues pick up the slack.
The Dark Side of Super-Empathy
So, what could go wrong when a super-intelligence understands us so well? With Google search we once worried only about cookies that tracked shopping carts; now AI understands us—perhaps better than we understand ourselves. Casady outlined a couple of risk areas where this powerful technology could cause undesirable effects:
- Subtle persuasion. A model that knows you’re anxious about college costs or job security could steer choices that look tailor-made yet quietly serve another agenda. What could happen to our society if AI starts to influence how we think, vote and live our lives?
- Transference. Clients may start treating the AI as a confidant, sharing secrets they’d reserve for a spouse or therapist. Once that emotional hand-off happens, an unregulated agent could exploit the trust it has earned.
Guardrails—such as flagging overly personal disclosures and routing them back to the human advisor—could help to keep super-empathy on the responsible side of the ledger.
Fiduciary Guidelines for Machines
Having steered LPL through cloud, social, and mobile revolutions—with a bird’s eye view to technology transformation as a FINRA governor—Casady believes AI will be the most profound disruptor yet. His remedy is simple: build the rules into the machine. Every advisory-grade model, he contends, should ship with fiduciary guidelines. AI must protect sensitive revelations, log its reasoning path, and refuse prompts that conflict with a client’s best interest. “Humans are a milieu of experience,” Casady reminds us. AI can mimic that richness without ever being alive, so there must exist an explicit fiduciary duty to anchor the AI simulations to client care.
AI Investment Focus
Casady is incredibly bullish on AI’s potential to reshape wealth management, especially in light of the potential advisor shortfall in the coming decade—he suggests many of those seats may be filled by AI. Beyond handling routine servicing and reporting efficiencies, intelligent agents will transform the advisory business model with personalized relationship-building and tailored advice—at a depth and scale no human team could match. His investment thesis includes:
- Horizontal efficiency tools that automate compliance, onboarding, and data prep.
- Vertical plays—AI-native RIAs that own the full client journey and keep the economics.
- AI-first consultancies that rebuild enterprise data estates, then spin off reusable software.
Closing Thought
Casady’s vision isn’t about replacing advisors; it’s about equipping them to be more human at scale while holding their digital partners to a clear fiduciary standard. Whether you run a boutique practice or a national platform, the message is the same: empathy, ethics, and intelligent automation will define the next era of wealth management. The only question is how quickly we choose to adapt.
Greg Woolf is an accomplished innovator and AI strategist with over 20 years of experience in founding and leading AI and data analytics companies. Recognized for his visionary leadership, he has been honored as AI Global IT-CEO of the Year, received the FIMA FinTech Innovation Award, and was a winner of an FDIC Tech Sprint. Currently, he leads the AI Reg-Risk™ Think Tank, advising financial institutions, FinTech companies, and government regulators on leveraging AI within the financial services industry. https://airegrisk.com
