5 Questsions About How AI is Shaping the Future of Financial Advice
By J.R. Robinson, Financial Planner (September 2025)
Below are a handful of questions from the transcript of a recent interview with Honolulu Star-Advertiser Tech View columnist, Rob Kay, that ended up on the cutting room floor. I have repurposed them into a timely op-ed piece for our Financial Planning Hawaii Insights readers.
What is your perception of the impact of AI?
I’m not sure I am the most qualified person to address the impact of AI outside of my own profession, as I don’t think I have ever been early to recognize the sweeping societal changes that have resulted from the remarkable innovations in technology over the past 50 years. That said, it seems increasingly evident that AI is ushering in a paradigm shift akin to the internet revolution, the introduction of web browser & search, the shift from desktop to mobile, and rise of social media. I believe there are very few industries that will be untouched by AI.
Do you view AI as a positive development, or do you view it as harmful?
AI is already enormously disruptive. It will undoubtedly be harmful to people in industries in which AI will entirely replace human workers. There are probably many industries where this will happen. Computer programming is an obvious and perhaps ironic career path that appears to be heading for obsolescence. On the flipside, AI is spawning entirely new industries, such as those that deliver AI agents to businesses of all sizes to dramatically improve productivity and workflows.
In terms of societal impact, I have no idea. Compute blew through the Turing Test more than a decade ago, and it is mind-blowing how incredibly real AI simulations have become. It is easy to see the harm and havoc it is already enabling cybercriminals to wreak. AI may even pose an existential threat to civilization. At the same time, the benefits to humanity of machine learning seem boundless. As a simple, tangible example, I describe my first ride in a Waymo cab as akin to what it must have felt like when people first transitioned from horse and buggy to the automobile.
I don’t view AI through a moral lens. For better or worse, I view it as inexorable. The genie is out of the bottle and is not going back in.
How do you see it effecting the investment Industry?
It’s funny you should ask. Last month, Microsoft released a report listing financial advisors at #30 on its list of the 40 industries most likely to be replaced by AI. I agree with industry thought leader Michael Kitces who predicts that attempts by AI-driven financial planning tools to supplant human financial planners will likely play out the same as every other industry disruption and will ultimately compete for the DIY market. This was the case with rise of the discount brokers such as Charles Schwab, Vanguard, Fidelity, and Quick & Riley in the 1980s. It happened again when the Internet ushered in online trading and day- trading platforms in the 1990s. The 2010s ushered in the Robo-Advisors. All of those disruptions were predicted to drive financial advisors to the same fate as the dinosaurs. All ended up expanding market-space opportunities for them instead.
Do you think AI will enhance investors’ portfolio performance?
I just listened to a fascinating podcast on the evolution and legalization of sports betting. It featured a professional gambler with a computer science and engineering background who applied machine learning to build an algorithm that could beat the casinos and the other sports books. He made millions before the regulators took him down.
Renaissance Technologies and Long-Term Capital Management proved that is possible for machine learning to achieve the same type of outperformance legally in the investment markets. My prediction is that select individual day-traders may be able to harness their own AI agents to discover novel ways to outperform even the most highly efficient public markets. However, as with sports betting, most will fail. There is a longstanding adage in the day-trading world – “Every system works until it doesn’t.” Nonetheless, I would not be surprised if consumer-level access to machine learning agents mints a few day-trading billionaires.
How do you see AI impacting your financial planning practice?
The financial advice business has been in a constant state of disruption for the 37 years that I have been in it. The mantra for all advicers is always “Adapt or Perish.” AI will undoubtedly disrupt many financial planners.
I often quip that I have gotten really good at adapting and not perishing. I believe the secret is to not ignore or resist inexorable change but to embrace it and look for opportunities to increase productivity and differentiate from competitors.
One AI tool that has dramatically increased my productivity is AI notetaking software. I include Jump AI in all client meetings. It saves me many hours of work each month and automatically populates summaries to our CRM and to the client’s financial planning platform. Similarly, I have always been a prolific content creator. Enlisting Perplexity AI has cut the time it takes for me to create an article from many hours to 15 minutes or less.
Looking ahead, I will soon be using an avatar to convert my blog posts to short video clips that may be shared on Instagram, TikTok, and YouTube. I am also working on getting my own AI agent I can turn loose on the hundreds of articles and papers I have written over the past quarter century. I am hoping I can harness its LLLM capabilities to serve as my proxy for visitors to our website who have financial planning questions. Both of these applications have the potential to be business differentiators.
My companies are intended to be multigenerational. I tell all new clients that my goal is to have my children and grandchildren help their children and grandchildren secure their financial futures. I view AI’s entrance into the financial planning space as an incredible opportunity to build the Financial Planning Hawaii and Fee-Only Planning Hawaii brands.
John “JR” Robinson is the owner and founder of Financial Planning Hawaii and Fee-Only Planning Hawaii and a co-founder of financial planning software-maker Nest Egg Guru.
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