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Guest: Dr. Preston Cherry, the Founder of Concurrent Wealth Management.
In a nutshell: The business of financial advice has always been built on a foundation of trust. But AI’s ability to synthesize complex ideas into easily-digestible soundbites and talking points has created a tempting shortcut for investors and advisors alike.
Why go through the work of building a relationship with a client if AI can optimize a portfolio in a couple clicks?
And how can everyday investors tell the difference between a trustworthy decision partner who’s going to guide them through a Life-Centered Financial Plan and an “expert” who lets AI do their thinking for them?
On today’s show Dr. Preston Cherry returns to discuss why an advisor who lacks genuine wisdom, judgment, and lived experience will never be able to fill those gaps with AI or deliver lasting value to clients.
.Dr. Preston Cherry and I discuss:
- Creating a “five-star restaurant” client experience.
- Dr. Cherry’s three stages of earning trust to build and maintain a client relationship.
- Moving beyond data to provide clients with clarity and confidence.
- Why younger tech-native advisors must pair their natural digital fluency with client connectivity.
- How to use AI as a communication coach.
- Why doing the “analog work” of defining your identity and ideal client is mandatory before optimizing for digital marketing.
- The ethics of AI-assisted writing.
- Will AI ever be better than a human advisor at behavioral coaching?
Preston Cherry on AI and the “advisor in the loop”:
“ AI moved from a prediction formula — what is the outcome that we’re getting to, and it just speeds that up — to now it’s agentic, doing massive workflows for huge companies. It’s almost a being. It’s proactive. It’s predicting more than math. It’s, ‘Where do you want to go and what do you want to do? We can do it right now.’ It’s fascinating how quickly it’s moved.
“Now, that said, to trust and making somebody smarter, there’s two things AI needs still. It still needs a competent expert person or entity and a combination of time and resources put together to scale the power of AI. And you can ask it to do things. You can ask it to ‘be a financial advisor.’ But then when that spits out what an advisor could and should be or what it needs to do, or to connect all these things and go further, that person, or the massive resources it takes to build a financial advisor agent, needs to be able to take that many steps deeper than what the AI is going to produce at that first go.”
Dr. Preston Cherry on what it takes to achieve true efficiency gains with AI:
“One of the terms that I use is ‘financial reality interpreted’. Yes, you can have all the information that you want. How are you interpreting reality? That is where terms like ‘discernment,’ ‘conviction,’ and ‘decisive clarity’ come from. People want to be led. They want answers, they want conviction, and they want the weight of those decisions taken off of their shoulders. After you receive all of their information and AI helps you organize it and gives thoughts, you have to know what to ask for the next question and several questions after that. I’ve had to curse AI out a couple times: ‘ Oh, you’re getting worse. Oh, we’ve already discussed that. No, that’s wrong. Where did you get that? Blah, blah, blah, blah.’
“So when you’re talking about will AI save us time, it depends on are we using it right to gain that efficiency, because it can be a rabbit hole. And if you don’t know what to ask it next, then it’s going to direct you somewhere that you don’t want to be. Time has been undefeated and still is undefeated, just like age. You have to put the time in for AI to learn yourself, learn your advisors if you have a team, learn your firm, learn how you do things uniquely, how you have those deliverables, how you transfer that trust. You have to have agents, rules, guidelines, and guardrails. And it takes time. And if you don’t have any of that in place, then no, it won’t save you time.”
Dr. Preston Cherry on whether or not technical financial advice will still be valuable in five years:
“It’s still going to be valuable. I’ve had a client come to me with pretty good financial planning deliverable. I was like, ‘Man, this is pretty good. Are you sure that you want to keep on with your profession? You want to be an advisor?’ It was good, and I told him that.
“I still looked at that and I came up with half-a-sheet of questions, and ‘This affects that, this affects that,’ and then how to narrow it in a way and make those decisions integrate and make them work. I’m not just talking about the humanness of it. I’m talking about the strategy, getting down to it and executing in a way that satisfies what he and his wife and his household wanted to do, not only now, but long term.
“And this person was a surgeon … of the brain! I’m never going to be that. I don’t care how many hours that I spend at Googling and YouTubing and using AI and trying to build an agent, I’m never going to be at that, never. And would I trust myself, after all that Googling and AI-ing, to do surgery on another person’s brain? No. You still have to know what to do with the information and know what to ask.”
