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Below we canvassed more than 20 retirement experts and financial planners in both Canada and the United States about how they and their clients can use new AI Tools to help investors pick stocks or ETFs and plan their retirement.
These experts were gathered by Featured.com, which has been supplying Findependence Hub with quality content for several years now. It has changed its procedure so that editors like myself can request input on particular topics we think will interest our readership. The sources are all on LinkedIn, as you can see by clicking on their profiles below.
Here’s what we asked:
What is your top recommendation for using AI tools like Grok or ChatGPT to enhance the investing experience or financial planning process for retirement?
Their answers are below, which have been re-ordered by me and in some instances edited down, using an ellipsis (…) to indicate cut passages.
“AI doesn’t replace financial advisors: it elevates investors to think and plan like one.”
One of the most powerful ways investors and retirees can use AI tools like Grok or ChatGPT is to transform information overload into clear, actionable insight not just faster, but smarter. These tools allow individuals to run scenario-based retirement models, stress-test investment ideas against historical data, and translate complex financial language into plain English they can actually act on. What I recommend most is using AI as an always-available financial co-pilot a tool that helps you ask better questions, explore tax and withdrawal strategies, and stay disciplined when emotions run high. Of course, AI should enhance, not replace, professional advice; but when paired with fiduciary guidance, it becomes a force multiplier for better decision-making. The future of retirement planning is not just automated: it’s augmented, where every person can access institutional-grade research and personalized planning at a fraction of the cost. — Justin Smith, CEO, Contractor+
Use AI for Grunt Work & Routine Analysis
I use AI to handle the grunt work for my finances. It’s great for automating my investment tracking and finding savings opportunities. For my SaaS business, I have ChatGPT audit expenses and run tax simulations. It catches small details I would definitely miss, but I always double-check with my accountant before making any big moves. — Cyrus Partow, CEO, ShipTheDeal
Running a fintech team, I use AI like Grok to track portfolios and summarize complex financial statements. I have it monitoring global trends that might affect Canadian retirement planning. Integrating these tools took some time, but the process is way less stressful now. My rule is to let AI handle the routine analysis while I double-check any critical decisions myself. — Sreekrishnaa Srikanthan, Head of Growth, Finofo
A good way to use AI tools like Grok or ChatGPT for investing and retirement planning is to treat them as helpful guides that explain financial topics, summarize current market information, and assist with planning choices. These tools can make complex financial ideas easier to understand, break down how different investment options work, and help create scenarios based on your retirement goals. You can ask questions to check your knowledge about topics like spreading your investments or tax rules related to retirement accounts, getting clear answers that fit your situation.
These AI tools also provide updated summaries of financial news and alert you to changes that could affect your retirement plans, like new laws or required withdrawals. While they do not replace a human financial advisor’s insight, they give you useful information that helps you talk to professionals with more confidence. Regular use helps keep you informed about your progress and reminds you of important details, making managing your retirement plan easier. — Richard Dalder, Business Development Manager, Tradervue
Use to summarize Market Trends
I work in tech marketing, so I’ve started using ChatGPT to research retirement investments. I’ll have it summarize market trends in telecom or healthcare IT, then cross-check with mainstream financial sources. This saves me hours of initial screening time. My advice is to never act on an AI’s take without fact-checking it first, but it’s a great way to get the lay of the land quickly. — Andrew Dunn, Vice President of Marketing, Zentro Internet
Use AI as a Personalized Planning Engine
My top recommendation is to use AI as a personalized planning engine. Feed it your retirement goals, income range, expected timeline, and risk comfort. Ask it to build draft scenarios, compare tax-advantaged account strategies, summarize differences between contribution options, or outline the impact of shifting a portion of your portfolio into metals, equities, or fixed income. This gives you a structured starting point before you meet with a licensed advisor.
AI also helps people evaluate items of value they already own. Many Americans keep gold or silver tucked away because they are unsure where to start or who to trust. Ask AI to walk you through how precious metal markets move, how payouts are typically calculated, and what reputable U.S. buyers offer. When people understand what their gold is actually worth, they make smarter decisions about whether to sell, hold, or incorporate it into their retirement strategy.
Using AI this way puts you in control. It speeds up research, cuts through noise, and helps you prepare with confidence before talking to a financial professional. — Brandon Aversano, CEO, The Alloy Market
I work with AI and financial data, and here’s what I’ve found: nobody reads those static retirement planning sheets. We switched to interactive simulations using tools like ChatGPT, letting people play out different investment choices and actually see the results. Engagement went way up. If you’re planning retirement in the U.S. or Canada, this gives you a much better feel for your financial future than any document. — John Cheng, CEO, PlayAbly.AI
Use to plan Retirement and support Financial Literacy
AI tools like Grok and ChatGPT shine brightest in retirement planning when used to simplify complex financial decisions. One powerful approach is creating personalized scenario models: quick projections that show how small adjustments in savings, expenses, or timelines can change long-term outcomes. This turns retirement planning from an abstract, overwhelming challenge into a set of clear, data-driven choices.
Another strong use case is ongoing financial literacy support. AI assistants can distill dense market insights, tax rules, or investment updates into plain-language summaries tailored to an individual’s stage of life. From my experience building learning systems at Edstellar, the real value comes when AI acts as a translator: cutting through jargon and helping people understand the “why” behind decisions. That level of clarity dramatically improves confidence, especially for long-horizon goals like retirement. — Arvind Rongala, CEO, Edstellar
An on-demand Analytical Partner
In my opinion, the best use of AI tools like Grok or ChatGPT when it comes to retirement planning is to enlist it as a personalized, on-demand analytical partner. When you present an AI with your financial data (savings, trajectory, risk profile, retirement age), it has the ability to remit stress testing of your assumptions at a breadth and speed most people will never do for themselves. I have even gone a step further and even asked the AI model to create a variety of long term simulations: good markets, flat markets, inflationary periods, tax shifts, and a few unexpected life surprises here and there. This is when you will feel a much better understanding of what the reality will look like on your retirement path versus static projections.
Where I do think AI can take the planning to another level is the rigor of thinking it is going to force on you. It will find blind spots you didn’t even know to look for, it will challenge your assumptions, it will allow you to show up to your advisor meeting with the potential to be prepared. In the U.S. and Canada—complex situations in retirement planning to say the least, not to mention personal—AI will present a great utility. It won’t replace your financial professional, but it might very well allow you to ask better questions and gain confidence in your decision making. — Kevin Baragona, Founder, Deep AI
AI is NOT a financial advisor
Running a finance team, I’ve found AI like ChatGPT is great for the first pass at retirement planning. It can explain jargon or summarize options way faster than reading a 20-page PDF. But here’s the thing: it’s not a financial advisor. Use it to get the lay of the land, but always talk to a licensed professional before you put any real money in. — Edward Piazza, President, Titan Funding
Treat AI tools as a Scenario Partner
One of the most useful ways I’ve leveraged AI tools like ChatGPT and Grok in the investing and retirement-planning process is by treating them as a “scenario partner.” Not a financial advisor, not a spreadsheet replacement, but a way to explore the assumptions behind long-term decisions.
When I was first building Zapiy, I didn’t have the luxury of long planning sessions with advisors. I needed quick clarity on questions like how much I should be contributing, how aggressive my allocations should be, or how different timelines would reshape my retirement targets. What I found was that AI excels at helping you pressure-test your thinking before you make any commitments.
I’d feed ChatGPT a basic profile — income, savings rate, intended retirement age, preferred account types like a Roth IRA or TFSA — and ask it to model a few “what if” versions: what if I increase contributions by five percent, what if I shift to a more conservative allocation in my forties, what if I retire earlier but maintain the same lifestyle? The answers weren’t perfect, but they gave me a clearer sense of how small behavioral changes compound over time.
The real value is that this preparation makes every conversation with a human advisor more productive. You walk in understanding your own priorities, trade-offs, and risk tolerance instead of starting from zero. For many investors in the U.S. and Canada, this hybrid approach — AI for exploration, experts for validation — seems to strike the right balance.
If I had to give one recommendation, it would be this: use AI to sharpen your financial instincts, not to substitute professional judgment. Let it help you see the landscape more clearly so you can plan with confidence and ask better questions when it’s time to make real decisions. — Max Shak, Founder/CEO, Zapiy
Large-language models aren’t crystal balls
With new AI tools, the first impulse is always to ask for a prediction. People want to find the next winning stock or time the market perfectly. I’ve seen this happen for decades with every new wave of technology.
But these large language models aren’t crystal balls. They’re incredibly good at synthesizing information and finding patterns in past data, but they also have a tendency to invent things with absolute confidence.
The hardest part of long-term investing isn’t about finding more data. It’s about managing your own psychology, your biases, and the emotional urge to react to every bit of market noise. This is where AI’s real, and more subtle, value comes in.
My top recommendation is to stop treating these tools like an analyst and start using them as a sparring partner to challenge your own thinking. Instead of asking something simple like, “What are the best Canadian dividend stocks for 2025?”, give it a much more powerful prompt.
Try something like this: “Act as a skeptical financial advisor. My plan is to invest 30% of my retirement portfolio in Canadian dividend stocks for income. Poke holes in this strategy. What are the biggest risks I’m ignoring, what behavioral biases might be at play, and what alternative approaches should I consider?”
What this does is force the AI to act as a “red team” for your own ideas. It uses its vast knowledge of economic principles and market history to find the flaws in your logic before you commit real capital.
This reminds me of a brilliant young engineer I once mentored. He had designed this complex, theoretically perfect trading algorithm and was in love with its elegance. Instead of telling him it would fail, I just spent an hour asking questions.
What happens if this data source is delayed by two seconds? How does the model behave in a flash crash? What’s the single point of failure? He came back two days later and scrapped the whole thing, starting over with a simpler, more resilient design.
The AI can be that patient questioner for you. True financial security isn’t built on finding the perfect answer, but on developing the wisdom to question your own. — Mohammad Haqqani, Founder, Seekario AI Job Search
Use for Stress Testing Assumptions
My top recommendation for using AI tools like Grok or ChatGPT to enhance retirement planning is not to use them for advice, but for stress testing assumptions. Never take financial advice from a large language model. That is a path to financial ruin. Instead, use the AI to aggressively challenge the core numbers you are already getting from a human financial advisor.
The effective use is feeding the AI a series of complex, negative scenarios based on your existing US or Canadian retirement plan. Ask the AI: “If inflation averages 5% over the next ten years, and my portfolio only returns 4%, where does the system fail?” or “If I move to a high-tax state and health care costs double, how does the plan survive?”
This approach works because it turns the AI into a powerful, objective risk auditor. It exposes the hidden vulnerabilities in your human-designed plan without the emotional filter of your advisor. This is the only high-value application: using AI to force clear, honest conversations about competence and failure points in your retirement strategy, ensuring you have the strongest system possible. — Flavia Estrada, Business Owner, Co-Wear LLC
Use to get a head-start on when to retire
Use AI tools like Grok or ChatGPT to get a head start on how to retire. These services will evaluate the state of your finances and most can administer a wide array of retirement and other accounts then recommend investments that fit your criteria. They demystify complicated financial subjects. They can help you with budgeting, monitor progress and shift plans as markets change. Ask questions in a frame where hopefully will receive clear and good advice. Bots driven by AI help save you time, reduce mistakes and change the way you think about money. It makes retirement planning much simpler and more straightforward. — Keith Sant, Founder & CEO, Kind House Buyers
Use AI as a Personalized Planning Engine
My top recommendation is to use AI as a personalized planning engine. Feed it your retirement goals, income range, expected timeline, and risk comfort. Ask it to build draft scenarios, compare tax-advantaged account strategies, summarize differences between contribution options, or outline the impact of shifting a portion of your portfolio into metals, equities, or fixed income. This gives you a structured starting point before you meet with a licensed advisor.
AI also helps people evaluate items of value they already own. Many Americans keep gold or silver tucked away because they are unsure where to start or who to trust. Ask AI to walk you through how precious metal markets move, how payouts are typically calculated, and what reputable U.S. buyers offer. When people understand what their gold is actually worth, they make smarter decisions about whether to sell, hold, or incorporate it into their retirement strategy.
Using AI this way puts you in control. It speeds up research, cuts through noise, and helps you prepare with confidence before talking to a financial professional. — Brandon Aversano, CEO, The Alloy Market
Use Grok or ChatGPT for financial literacy support
AI tools like Grok and ChatGPT shine brightest in retirement planning when used to simplify complex financial decisions. One powerful approach is creating personalized scenario models: quick projections that show how small adjustments in savings, expenses, or timelines can change long-term outcomes. This turns retirement planning from an abstract, overwhelming challenge into a set of clear, data-driven choices.
Another strong use case is ongoing financial literacy support. AI assistants can distill dense market insights, tax rules, or investment updates into plain-language summaries tailored to an individual’s stage of life. From my experience building learning systems at Edstellar, the real value comes when AI acts as a translator—cutting through jargon and helping people understand the “why” behind decisions. That level of clarity dramatically improves confidence, especially for long-horizon goals like retirement. — Arvind Rongala, CEO, Edstellar
Get simple, customized advice on what you should be thinking about when preparing for retirement using AI tools like Grok or ChatGPT. They can tear apart your finances, recommend sound investments and demystify complicated topics. These are tools to help you budget, measure your progress and bend as needed. Answers can be either helpful or come quickly by being more specific in your questions. They cut down on time, reduce errors and all in all make retirement planning simpler and more effective. — Amanda New, Founder, Cash For Houses Girl
Uncover hidden risks or savings strategies
Try pasting some market data into ChatGPT and ask it to model different retirement scenarios. I’ve seen entrepreneurs do this to test out asset allocations, and it pulls up angles they hadn’t considered. Look, I’m not a financial advisor, but this approach often uncovers hidden risks or savings strategies that the usual tools miss entirely. It can give you a new perspective. — Vlad Ivanov, CEO, WordsAtScale
The best way to use AI tools like Grok or ChatGPT for investing and retirement planning is to treat them as a decision support partner rather than something that makes investment decisions or predicts markets. AI is most effective when it supports how you think, organise, and act, not when you ask it what to buy.
In my view, the real value concentrates in four areas:
1. Clarity: turn complex financial information into something you can understand
Retirement plans, account structures, fee disclosures, and tax rules in the U.S. and Canada are written for estate planners and tax professionals, not for everyday investors. AI can read these documents, summarize the essential points, and highlight the parts that matter for you.
Example: You can paste your 401(k) or RRSP summary into an ChatGPT and ask for “the top five points that affect my costs, taxes, and employer match.” AI produces a clear digest within seconds.
2. Structure: put all your financial information in one place and make sense of it
Most people keep their financial details scattered across emails, PDFs, and personal notes. AI can organise this information into a coherent overview of your financial situation.
Example: Upload statements, notes, and calculations into Google NotebookLM and ask AI to create a consolidated snapshot of your accounts, balances, and key dates.
3. Goal setting: define what you are actually working toward
Good planning requires a target. AI can guide you through questions about lifestyle, retirement age, savings habits, and income stability. It can turn your answers into a concise retirement design brief.
Example: Ask Grok AI to “interview me and create a one-page summary of my retirement goals,” which you can later bring to a financial advisor.
4. Scenario modelling: understand how your choices affect long-term outcomes
AI cannot predict markets, but it excels at showing how changes in your decisions alter the shape of your retirement plan. By adjusting variables such as retirement age, savings rate, or contribution strategy, AI can run simple sensitivity checks that reveal which choices have the greatest impact.
Example: Ask AI to compare retiring at 60 vs. 67 or saving 10 per cent vs. 15 per cent. It can show which variable shifts the outcome most.
In summary, AI should not replace professional advice. Its purpose is to make you more organised and more prepared when working with the tools and experts who manage regulated financial decisions. — Andrius Budnikas, Chief Product Officer, Gainify
Gemini pulls current data better than ChatGPT
Ask AI to identify your knowledge gaps rather than giving direct advice. I prompt with “What would a planner need for my retirement assessment?” This surfaces overlooked factors: healthcare inflation, required minimum distributions, tax implications. I stress-test scenarios: retiring earlier, relocating, adjusting savings.
What works well for me is using Gemini for research since I find it pulls current data more effectively than ChatGPT. This builds financial literacy so I grasp asset allocation and withdrawal strategies without feeling overwhelmed. These tools help me ask better questions before major decisions. Just remember AI projections assume average returns and can’t account for volatility or unique circumstances.
Just keep in mind that they’re educational aids, not replacements for certified professionals. — Nicola Boldrini, CMO, FinchTrade
Use AI to explore, organize and refine your thinking, then consult a professional
My primary suggestion is to use tools like ChatGPT or Grok to pressure-test your retirement planning assumptions but not to make investment decisions for you. In my experience through GPTZero, I’ve found that AI creates the most value when it assists people in eliminating complexity and identifying blind spots and that’s where AI excels in financial planning.
If you’re thinking about retiring at 62 versus 67, contributing more or less to your retirement account or being a little more aggressive or conservative in your investment strategy, AI can model the impact of each of these suggestions in a matter of seconds in easy to understand language. It will help you recognize trade-offs you may not have thought of and prepare you to have a better conversation with a human advisor, as you now have a more thoughtful representation of your financial plan. Think of it as an on-demand engine of simulation combined with real-time insight, clarifying and simplifying financial planning and advisory processes.
Just don’t confuse clarity for accuracy generative AI is not using a current, real-time financial data set, and it can also sometimes misinterpret tax rules or nuances of retirement accounts, so take everything with a grain of salt. The best advice is to simply use AI to explore, organize and refine your thinking, and then use the traditional professional tools or the support of live and human advisors. The combination of both is the best path forward to getting the best outcome for financial planning, trusted, data-driven professionals with the support of AI. — Mr Edward Tian, Founder/CEO, GPTZero
I’ve been using AI tools like ChatGPT for my own financial planning. I uploaded a few years of my spending data and had it run some retirement scenarios. It actually pointed out a big hole in my plan that I’d never noticed. I’d suggest trying it with your own numbers. It gives you something real to bring to a financial advisor instead of just guessing. –– Runbo Li, CEO, Magic Hour
Use AI with a Hybrid Approach
My top recommendation for using AI tools like Grok or ChatGPT in investing or retirement planning is to treat them as research and scenario-testing assistants, not as a substitute for professional advice. These tools can help you explore “what-if” scenarios, compare different withdrawal strategies, or analyze potential portfolio risks. For example, you can model the impact of different retirement withdrawal rates or simulate the effect of inflation on long-term savings. AI can also summarize market trends, highlight risk factors, or compare investment options, saving time and providing structured insights.
However, it’s important to remember the limitations. AI cannot fully understand your personal situation, risk tolerance, tax considerations, or long-term goals. Outputs may be too generic or occasionally inaccurate. The safest approach is to use AI to prepare questions, organize information, or test scenarios, and then validate findings with a licensed financial advisor or up-to-date data.
The most effective use of AI is a hybrid approach: it augments your research and planning, improves efficiency, and provides new perspectives, while you retain control over decisions and ensure compliance with your financial goals. By combining AI insights with professional guidance, investors can enhance decision-making, explore more options, and build a more informed and resilient retirement plan. — Andrew Izrailo, Senior Corporate and Fiduciary Manager, Astra Trust
Use AI to explore Alternative Retirement Plans
Artificial intelligence tools such as Grok or ChatGPT can help simplify retirement planning by explaining your alternatives and guiding you toward better choices. My No. 1 recommendation: exploring alternative retirement plans. They can represent how your savings, investments and spending could appear in the future. Those tools can also demystify the more difficult-to-understand aspects of your financial life — taxes, say, or how to diversify your investments. With the help of A.I. to provide clear guidance and enough time for planning, you can have more confidence that you will reach what you need in retirement. — Evan Tunis, President, Florida Healthcare Insurance
