Last September (2025), I sat down for an interview with local Hawaii journalist Rob Kay who writes the Tech View column for the Honolulu Star-Advertiser. The theme of the interview was to get my take on the impact of AI on DIY investors. It was a fun and engaging conversation, and the article appeared in the October 15th edition of the paper. This article repurposes some of the questions that were outside the narrow scope of the article, but are worth sharing in a broader context.
What is your perception of the societal impact of AI?
I am not sure I am more qualified to answer than anyone else on the planet, but I will try to answer that question from the perspective of someone whose investment career began with the algorithmic trading-induced stock market crash of 1987. Since that time I have had front row seats to the rise of the personal computer, the introduction of the Internet, the introduction of the web browser and search, the rollout of the iPhone, the transition from desktop to mobile, and the rise – for better or worse (mostly worse, I think) – of Social Media.
At the present time, I am witnessing the simultaneous introduction of driverless cars, which I believe is no less awe-inspiring than the transition from the horse to the automobile, and, of course the the beginning of the AI-Age, which I fully believe is the successor to the Information Age.
While I have no idea whether AI stocks are in bubble territory, I do not doubt for a second that the impact of AI will be every bit as impactful as any of these incredible innovations. In fact, I believe its impact on society as a whole may be on par or greater than the impact of the Internet, which ushered in the Information Age. I cannot hazard a guess as to whether the eventual impact will be revolutionary in a positive way for humanity or if it will be catastrophic.
I can say that most of the publicly traded companies that are driving the AI train are not akin to the ephemeral paper tigers that fueled the dotcom boom. They are the largest and most profitable companies on the planet for a reason. Ultimately, I believe there are very few industries that will be untouched by AI.
How do you see it effecting the investment Industry?
Last summer (2025), 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 investor market.
This was the case with the emergence of discount brokers 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 and Robinhood. Each of those disruptions was predicted to drive financial advisors to the same fate as the dinosaurs. All ended up expanding market-space opportunities for us instead.
In my communications with people at some of the AI startups that are aiming to replace financial planners, I see the same overconfidence I saw with Robinhood, Betterment, and Wealthfront. They are all out to “democratize” something but they seem incredibly naïve about how grassroots financial planning really works. That’s just my two cents.
Can AI chatbots or agents accelerate financial literacy?
The short answer is, “Yes.” If AI agents are trained on high-quality, domain-authority sources, they could dramatically enhance consumer financial literacy. I know of one AI firm already in talks with a large advisory company to do exactly that as a public service initiative.
The problem is that today’s leading LLMs (Large Language Models)—ChatGPT, Gemini, Perplexity, and Anthropic—too often amplify “finfluencers” with thousands of followers on TikTok, YouTube, and Instagram rather than academic researchers or seasoned industry voices. That’s how disastrously bad advice proliferates.
AI has the potential to raise financial literacy, but, at this moment in time, AI search is disastrously bad at providing sound investment, tax, and legal advice.
Do you think AI will enhance investors’ portfolio performance?
Unfortunately, no. I believe the allure of AI-driven trading is already proving irresistible to technology minded traders, but the outcome will be similar to the Robinhood experience. Thousands of investors will be encouraged to trade their brains out and will generally be poorer and perhaps jaded for the experience.
As with prior iterations, I suspect that AI-driven trading will tend to look good as long as the stock market is up, but the additional risk from frequent trading in volatile securities will exact its price when the next bear market rolls in. Not to be trite, but, as Warren Buffett always said, “When the tide goes out, you get to see who has been swimming naked.”
Could AI help DIY investors avoid behavioral mistakes like panic-selling?
I’m not optimistic. Vanguard and the Boglehead community, and even Motley Fool have long promoted responsible buy-and-hold investing with low-cost index funds. At the other end of the spectrum, Robinhood gamified investing with and brought meme stocks and crypto trading to the masses. If I had to bet, I think AI-generated investment advice will lean more toward the Robinhood model than the Vanguard one.
So what kinds of AI tools will actually be useful?
I have to admit; the most intriguing application of AI tools will be in enabling investors to train their own AI agents to create personalized trading strategies.
The siren song of “market-beating” returns will be irresistible. Quantitative trading firms such as Renaissance Technologies and D.E. Shaw have already proven it’s possible. However, it is worth knowing that the companies were founded and staffed by mathematical geniuses and cost many millions of dollars per year to operate. This puts your average wishful AI trader at a decided disadvantage, but you never know.
I recently 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.
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. I hope it does.
How do you see AI impacting your financial planning practice?
The financial advice business has been in a constant state of disruption for the entire 37 years that I have been in it. The mantra for all advisors 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 that 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 LLM 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.
Financial Planning Hawaii is intended to be a multigenerational company. 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.
What sources of information do you use to keep up with the latest financial planning and technology trends?
For financial planning industry related trends and new developments, I follow Kitces.com, Jeff Levine, CPA, and Ed Slott & Co. For technology, I am an enthusiastic fan of the Acquired Podcast. The insights I have gained from Ben and David’s deep-dive company histories have definitely made me a more knowledgeable investor. The show, along with their interview-oriented spinoff ACQ2, have helped me to better understand technology trends as well.
Here is a link to my favorite Acquired Podcast Episode – one that is definitely germane to this discussion: Renaissance Technologies, Season 14, Episode 3 (March 17, 2024)
John H. Robinson is the owner/founder of Financial Planning Hawaii and Fee-Only Planning Hawaii. He is also a co-founder of fintech software maker Nest Egg Guru.
