July 2026
Featuring
Stacey McKinnon, COO, CMO, Wealth Advisor and Partner
Kevin Rex, Wealth Advisor and Partner
Two hundred million people a month turn to AI for financial advice. The answers they get are technically accurate, carefully hedged, and almost completely generic. In this episode of Couchside Conversations, Wealth Advisors Stacey McKinnon and Kevin Rex ran a live experiment: they asked ChatGPT to surface the five most common financial questions people search for, then answered each one themselves without seeing the AI’s responses in advance. What emerged is a study in the difference between information and advice, and a reminder that the most important financial questions are never really just about money.
AI gives you information. A financial advisor gives you advice.
ChatGPT’s answers to every question in this episode were directionally reasonable and consistently shallow. They gave benchmarks without context, formulas without values, and frameworks without follow-up questions. The gap between what the AI said and what Stacey and Kevin said is precisely the gap between a starting point and an actual plan.
The right financial question is almost never the one being asked.
Behind every question about retirement savings or career changes is a set of values, priorities, and life circumstances that change the answer entirely. Stacey and Kevin returned to this point across all five questions: the real work of financial planning is identifying what someone actually wants before running any numbers.
The sandwich generation needs a conversation strategy, not just a savings strategy.
Caring for aging parents and children simultaneously is one of the most financially and emotionally complex situations a person can face. The most underrated tool for navigating it isn’t a budget — it’s a frank conversation with your parents about their financial situation before a crisis forces it.
Debt payoff isn’t always the mathematically correct move but it’s sometimes the emotionally correct one.
The 7% threshold Kevin uses as a guidepost is a useful starting point. But both advisors note that clients who carry debt they hate. Even low-interest debt, often benefit from paying it off early for reasons that have nothing to do with the math. The emotional freedom of a cleared payment has real value.
The rent-vs.-buy calculus has genuinely shifted in Southern California.
For the first time in a generation, renting and investing the difference can produce more wealth than owning in high-cost markets like Southern California. The 40-year bull market in real estate that made homeownership a reliable wealth-building tool is not something either host expects to repeat. Homeownership is not the same as financial success.
“There’s a narrative that the American dream means you’re successful if you own a home. I actually don’t think homeownership should equal success. If renting gives you more financial freedom to do the things in life that you love, that could be a successful life.” — Stacey McKinnon
0:01 The premise: 200 million people a month seek financial advice from AI
1:06 Why AI is great at information but struggles with personalized advice
1:38 Question 1: Am I saving enough for retirement, and is it too late to catch up?
2:14 The 5% rule: how Stacey backs into a retirement number from desired spending
3:25 Why your house is not a retirement plan, and the case for a three-bucket approach
5:10 ChatGPT’s answer to Q1: generic benchmarks, zero values
6:19 Question 2: How do I take care of my parents and my kids and still build my own wealth?
7:01 The sandwich generation: time, complexity, and what gets missed without early conversations
8:19 Why talking to your parents about money in your 30s changes everything in your 50s
9:56 ChatGPT’s answer to Q2: right direction, wrong depth
11:14 Question 3: Should I stay in my career or make a change, and can I actually afford to?
12:56 The question under the question: do you have growth opportunity, or just discomfort?
14:06 ChatGPT’s answer to Q3: solid math, nothing about fulfillment
16:02 Question 4: Should I pay off my debt first or start investing?
16:54 The 7% threshold and how to think about arbitrage between debt cost and investment return
17:48 When the emotionally correct answer beats the mathematically correct one
19:23 ChatGPT’s answer to Q4: the one where they mostly agreed
20:59 Question 5: Should I buy a home or keep renting, and how do I know if I’m ready?
21:19 Why renting can produce more wealth than owning in Southern California today
23:19 Dismantling the American dream narrative: homeownership is not the same as success
24:51 The 40-year real estate bull market and why it probably isn’t repeating
26:08 ChatGPT’s answer to Q5: the price-to-rent ratio and what it actually tells you
26:46 Closing: what surprised them most about the questions people are actually asking
Watch previous episodes:
Top Reasons We Overspend (Even Financial Advisors Do It)
These are the questions real people are typing into ChatGPT, Google, and Instagram every month. We’ve addressed them directly below. The full conversation, including how the AI answered each one, is available in the transcript further down the page.
Am I saving enough for retirement, and is it too late to catch up?
The short answer is: it depends on what you want retirement to look like, and the starting point isn’t a benchmark — it’s a spending number. Stacey uses a straightforward rule of thumb: decide how much you want to spend annually in retirement, multiply by 20 (or equivalently, target a portfolio that lets you withdraw 5% per year), and that’s the number you’re working toward. A $3 million portfolio supports roughly $150,000 in annual spending; $4 million supports $200,000. ChatGPT’s answer cited age-based benchmarks — three times your salary by 40, six times by 50 — that tell you nothing about your actual expenses, your housing situation, whether you have kids, or what you want the money to do. That’s the difference between a benchmark and a plan.
How do I take care of my parents and my kids and still build my own wealth?
This is the sandwich generation question, and it’s as much about time as it is about money. Kevin’s first instinct is to understand the full picture: what do your parents actually have, what do they need, and what do you want for your kids? Those answers drive the number. But the single most underrated piece of advice in this episode is to have that conversation with your parents before a crisis makes it urgent. Families who talk about finances in their 30s have options. They can plan, save, structure, and prepare. Families who don’t tend to find out the hard way in their 50s. You can’t borrow for retirement, but you also can’t retroactively create a plan you never had.
Should I stay in my career or make a change, and can I actually afford to?
There are really two questions embedded here: one about fulfillment, one about finances. On the financial side, the basics matter — what are your fixed monthly costs, how much runway do you have, and what does income look like in the new path over a five-year horizon? But Stacey pushes further: people in this situation are usually either unhappy with the work itself or feel like they’re not making enough to live comfortably. Understanding which problem you’re solving changes the answer entirely. A career change that pays less but offers growth and satisfaction may be a better long-term financial decision than staying put, especially if the numbers support it. And knowing your full financial picture, including what a partner contributes, what you actually spend, and what a transition period costs, is how you make that call with confidence rather than anxiety.
Should I pay off my debt first or start investing?
Kevin uses 7% as a practical threshold: if your debt carries an interest rate above 7%, pay it off before you invest, because you’re unlikely to reliably beat that rate in the market. Below 7%, there’s a case for holding the debt and investing the difference, particularly if your employer offers a 401(k) match, which is an immediate guaranteed return. The nuance both advisors add: this is also an emotional question. Some clients hold a 4% mortgage but can’t stop thinking about it. Paying it off may not be the optimal financial move, but if it eliminates a source of chronic stress, it has real value. Knowing why you have debt in the first place matters too. If overspending is the pattern, eliminating debt without addressing the habit just resets the cycle.
Should I buy a home or keep renting, and how do I know if I’m ready?
This is the question where Stacey and Kevin pushed back hardest against conventional wisdom. In high-cost markets like Southern California, the math has genuinely shifted: when you account for mortgage payments, property taxes, insurance, and maintenance, all of which have increased significantly, renting and investing the difference can produce more wealth over time than owning. That wasn’t true for most of the past 40 years, when a bull market in both real estate and interest rates made homeownership a powerful wealth-building tool. It may not hold going forward. The other factor: younger generations are more mobile, waiting longer to marry and start families, and less interested in being tied to a location. The price-to-rent ratio is a useful tool, if it’s above 20 in your market, renting often makes more financial sense. But equally important: stop treating homeownership as a proxy for success. It isn’t one.
What can AI actually do well when it comes to financial advice?
Stacey and Kevin aren’t anti-AI, they use it themselves and expect its capabilities to keep improving. Where it earns its place: surfacing information quickly, explaining concepts clearly, and giving people a starting framework when they have no framework at all. Where it falls short: asking follow-up questions, understanding values, knowing what a person actually wants, and translating general principles into decisions that fit a specific life. The five questions in this episode all got directionally reasonable answers from ChatGPT. None of them got the answer a good advisor would give, because a good advisor knows the person asking.
Two hundred million people a month are getting financial guidance from AI. That number is going up, not down. And for most of them, the information they’re getting is not wrong, it’s just incomplete in ways that can cost them significantly over time.
This episode is especially relevant for:
At Morton Wealth, the difference between information and advice is something we think about constantly. The questions in this episode don’t have universal answers, they have answers that are right for you, based on your values, your situation, and what you actually want your life to look like.
DISCLOSURES
Information presented herein is for discussion and illustrative purposes only and is not intended to constitute financial advice. The views and opinions expressed by the speakers are as of the date of the recording and are subject to change. These views are not intended as a recommendation to buy or sell any securities, and should not be relied on as financial, tax, or legal advice. You should consult with your finance professional, accountant, or tax professional before implementing any transactions or strategies concerning your finances.
