BiggerPockets Money Podcast - How to Use AI to Improve Your Finances and Reach FI Faster

Episode Date: September 18, 2026

In this episode of the BiggerPockets Money Podcast, Mindy Jensen and Scott Trench explore how you can use AI to make better financial decisions and move closer to financial independence. They share practical ways to ask better questions, give AI the right context, stress test your financial plan, and even develop an investment thesis. Plus, they talk about where AI can help and why you still need to double-check its work.To go beyond the podcast:Interested in a Flat Fee Financial Planner? Go to https://biggerpocketsmoney.com/fipro/Interested in Learning More About Buying a Franchise? Check out: biggerpocketsmoney.com/franzyGet 50% Off Your First Year of Monarch by using code ‘Pockets’: https://www.monarch.com/pocketsWe believe financial independence is attainable for anyone no matter when or where you’re starting. Let’s get your financial house in order!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Can AI help you reach by faster? Today, we are talking about how best to use AI to help you stress test your financial independence plan, whether you're just starting out or you're nearing the finish line. Hello, hello, hello, hello, and welcome to the Bigger Puckets Money podcast. My name is Mindy Jensen, and with me as always is my AI agnostic co-host, Scott Trench. Thanks, Mindy. I'm always just excited to work on my core model. But yes, I'm excited to talk about this. We just talked with Professor Oswath de Maderen from New York University about AI and the Mega Cap Complex. And, you know, I think that there's a little bit of the question mark out there about how AI is going to generate returns for investors. But I think there's no question that AI is an extremely powerful tool that you can

use in your personal finances today. Even if you only use one tip from today's episode, I think it'll be very powerful for you, even if you're not using it at all. And hopefully some of the ideas will give you, you know, just a little perspective about how I'm using AI and how Mindy's using AI and how we think it can be applied to your situation. We'd also, this is a new field. We'd love your feedback if you have tips or prompts or ideas that you are bringing to the table and using with AI to evaluate your personal finances. So send them to Scott at BiggerPocketsMoney.com or Mindy at BiggerPocketsMoney.com if you have them. And with that, let's get into it. All right, Scott, what are some of the guiding principles that you use to help you

formulate your questions for your AI. I think AI benefits most when you can bring it a framework. If you let it invent the framework, that's where you can get yourself into trouble. And you can get yourself into trouble when you depend on it. When it's telling you to do something you don't understand, that's when you're about to really burn yourself. But when you use AI to take the complex, messy situation of your life and summarize it, simplify it or make it actionable, that's when the power begins to emerge from AI. Well, the first principle, I think of using AI is to start with tangible questions and get as much clarity as you can bring to your financial position, especially in the context of your specific situation, exactly where you're at

today and where you want to go, with your goals in the future. If you can articulate those crisply, you're going to help the AI just as you would help yourself, your spouse, or a financial planner in a professional setting if you could bring that information to that. One of the big tips that I have learned when using AI and using, like, writing prompts is more is better. So, yes, you want to be succinct as possible, but give this thing a ton of information, especially when you're first starting out. This is me. This is what I want. Like, have a conversation with it.

Don't just type in five words. Do this. No, this is all of my background. Pretend like you're having a conversation with an actual person instead of asking a software to do something for you. I think framing it with information is very helpful as well, because it will invent stuff sometimes if you don't give it detail. And it will still mess up, even if you do provide a detail, but just like humans do, by the way, in some situations. As part of that, some of the stuff we're building over at biggerpocketsmoney.com slash resources,

for example, could be helpful. Like, we've got a personal financial statement over there. That could be a great thing to download, put in some of your information or redacted or change it if you're concerned about privacy. But put in the information into the personal financial statement and upload it to the AI, the AI will then have context on your situation and be able to answer certain questions. You can reference that document, right? Another good one is framing how you want to handle certain situations. So, for example, I, with my insurance, as someone who's financially independent and has a significant net worth, I like to pay the lowest premium possible, and I'm willing to pay a higher deductible in order to get a lower premium. That means I'd want a bronze

Affordable Care Act plan, for example, for my family. A car insurance policy, for example, that had a lower premium and higher deductible, or maybe I would self-insure my car as I bought the insurance to insure other drivers in the road. So that framework matters because the AI is going to default to something different if it doesn't understand your preference and how you want to handle some of those. And then the core challenges that you want to address, right? The core challenge at first could be where the heck is all our money going? I don't even know. Help me diagnose and just build an accurate representation of my finances. Another core challenge could be, I feel like I'm underpaid at work. how do I progress my career going forward? Another one could be I'm overpaying for insurance and I want to shop and

change my insurance philosophy because I can afford a higher deductible and I have a large cash position. You know, can one parent afford to quit or just work less? That's a common one we get. But giving those challenges and saying what are the top concerns in my situation will help the AI ground its discussion and interpretation of these things against that core challenge. These are all great tips, Scott. And again, I can't stress enough. give this thing a ton of information, especially when you're first starting out. They learn about you as you go. So down the line, you might not need to give them so much information. But if this is your first interaction with AI, act like you're meeting a new person. This is all about me. Act like you're meeting a new CFP. And then the information that you get from AI, you are definitely going

to want to double check. The next principle that I like to put into play when using AI is I like to give it a definition of strategy. I'm a big stickler for this, and I annoy people with this, but strategy, I think, is key, is so many things in business and life. And it's a diagnosis that accurately represents your situation. It's a set of guiding principles that actually focus on your challenge. And then it's a specific set of actions that you could begin implementing reasonably quickly or immediately to actually follow from the diagnosis instead of guiding principles. For example, if a one parent wants to quit or work less, then the entire strategy, the financial plan that we're building here, should be a reasonable interpretation of our existing position, what the cash flows look like or withdrawal capabilities of our portfolio look like, what the difference in the remaining spouse who continues to work's income and your expense profile is going to look like, and whether we can reasonably cut back or stop working entirely. We want everything grounded in that, and we want to understand the tradeoffs, the lost wealth that we will not be building towards age 65 around that.

That's what strategy or financial planning is. It's a set of tradeoffs. And I think that that's where the AI can be a superpower. If you force it to apply strategy. And if you don't, you can risk getting a garbage checklist of best practices that broadly apply to American finance, but don't apply maybe to your situation. Yeah, I think it's really helpful to be able to ask. specific to you questions. This is my specific situation. This is how much I make. This is how much my partner makes. We want to have a baby and I want to stay home. Or I already have a baby and I want

to go down to part-time. These are our expenses. This is all of our information that will maybe be pertinent to this decision. Help us walk through this. And you can anchor the strategy component with that by giving it a prompt like using Professor Richard Ruhmelt, author of Good strategy, bad strategies, definition of strategy in diagnosis, guiding principles, and specific action. Help me understand, you know, what my core challenge is here and how I can go about addressing it most effectively. That kind of thinking will help the AI focus on your challenge, for example. The next principle I have is think in iterations. AI's superpower is its ability to generate a draft almost instantly, right? I mean, you can literally type in a prompt and you will get a draft

if you ask for it, moments later or minutes later, depending on how big of a prompt you get, maybe a few hours at most if you're doing something really complex, I'm using one of the frontier models and there. But that's its superpower. Abuse that. It should help you generate a bad rough draft almost instantly and iterate sequentially to a fantastic rough draft over the course of the day or even a week or two. And that is really the superpower of this. And if you think like that, hey, this is my latest iteration. This is a draft here. That's going to help you not overcommit yourself or make a huge mistake that you can't cover from in this process because the AI can make mistakes. But if you put it together in draft format, I think you're going to get to a really strong starting position where the huge irreversible

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rough draft that you get from this AI, download it, and and then upload it to this AI and ask it to give commentary about that, ask it to pick this draft apart. That's a great way to find good overall but not good for you suggestions in this what you thought was a fantastic rough draft. Or maybe the second AI or the third AI doesn't find any issues with it. That's when you know that you've got a really solid plan to start looking at more deeply. Yep, absolutely.

And by the way, incognito mode is a great friend for a lot of these, right? So you can say, hey, go into chat GPT and do a temporary or incognito chat and ask it to produce a rubric, say, what does a world-class financial plan look like for a married couple in their 30s with two young children earning about this amount of income with about this amount of expenses in this type of portfolio in its existing sense. The goal is to retire early, but still have plenty of margin of safety to make it to 65. It wouldn't be the worst thing in the world. You know, we don't hate it.

We know at our jobs right now. It wouldn't be the worst thing the world to work an extra year or two if that greatly increased our safety margin and gave us long-term terminal wealth. Give it a prompt like and ask it, what does a world-class financial plan look like? Or a rubric for a financial plan look like to have a grade a financial plan artifact for this couple. And then once it's produced that, then submit your latest draft or iteration against that and ask it for grading against that rubric. It's not perfect. You'll still encounter problems, but I think you'll be able to see the power of that speed of that iteration. and exposing weaknesses in your plans or unaddressed areas or challenges very quickly.

And that's going to greatly improve the quality of the artifact that you, the draft that you're producing. Yeah. Keep in mind that it is just a draft. I think the fourth guiding principle should be don't take it for granted. It's still a work in progress. AI can absolutely make mistakes. And it will occasionally confuse popular opinion for accurate factual information in the context of analysis.

So I think, yeah, that's the last. principle, right, is don't take it for granted. It will confuse this stuff all the time. For example, I think that in the world of financial independence, a good option for life insurance is to build a term life ladder, right? So if I need two and a half million dollars to hit my financial independence number and I had zero net worth, I would want a two and a half million dollar term life policy to protect my family in that situation. I'm overly simplifying here, but that's, that's an idea. But let's say a couple years go by and I have a million dollars in net worth, and my financial independence number is still two and a half million dollars, well, then I'd want a $1.5 million

policy to bridge me from my $1 million net worth to my $2.5 million financial independence number, right? So a term life ladder, if someone was starting from zero and working towards a two and a half million dollar target might look like having a $500,000 policy that will expire after 10 years, a $1 million policy that will expire after 20 years, and a second $1 million term policy that will expire after 30 years. That way, as they reach presumably growth, wealth across that time period, those policies roll off, and the insured amount is the remaining bridge to my financial attendance number, right? You can see how that would save you a lot of money because you're not paying for 30 years for a policy you don't need the entire way, and you're still,

you know, assuming you have your framework correct and you understand how much your family needs, making sure that your family is protected in the event of your passing. That's to me what a good policy looks like. However, most of the rest of the world talks about a multiple of income, you know, 10 times your income or 20 times your income, and that's the amount you should insure for. So if you don't give the AI frameworks like that, then the AI may default you to something that is not best for your family or your situation in a lot of these situations. So that's, the more you know, the more powerful the AI is in some ways in a lot of these areas. Because otherwise it may produce a recommendation. You don't understand what's really behind it,

why it's doing that, because it's just giving you consensus or most popular viewpoint, not what's actually making the most sense in your situation. Strategy. Yep. That's a great tip, Scott. Let's talk about some specific tips. What do you got, Mindy? What's So what's the first one here? Use the AI to help you develop your personal financial statement or a summary of your position. Now, you can take the one that we have at biggerpocketsmoney.com slash PFS, which stands for personal financial statement, fill it out and upload that to the AI and ask it to analyze where you're at along with where your goals are and give you kind of a plan for how to get to that place. If you are using a tool like Monarch, you can download your transaction activity and, upload that to your AI, or you can use the native AI on Monarch.

Upload your credit card statements, your bank statements, and ask AI to analyze what's going on in your situation compared to where your goals are. By the way, you can redact all of this information if you so choose to. You can pull out certain things. You can choose exactly how much or whether to share anything with the AI. However, this I think episode does presume that you're generally comfortable with sharing the information with the AI. If you're not, don't and go talk to a financial planner or use some other process here. I'm a big believer that this is going to amplify our financial journeys. And if the AI becomes as good as we think it will be, it'll be able to hack our information anyways within a few years.

So might as well make the best use of it. It could be a risk that other people find totally unacceptable. I find the benefits to be very, very powerful from using AI and being fairly open with it and with my finances. But that's a personal choice that many other people will make differently across time. But you can redact this and should abuse incognito mode. with the AIs where it supposedly does not store your information. And yet, like when you said, the personal financial statements, the resources we're building at bigger pockets money.com slash resources are built with AI in mind and using AI in many cases because I think that that's what makes it powerful. Download that personal financial statement, fill out that information.

Now the AI is receiving your information in a framework that makes sense to it and the approach to financial independence. Then ask it to modify and personalize it, right? If you're not a real estate investor, the real estate schedule and the personal financial statement is useless. If you are a real estate investor and you have 40 properties, it only has the fault template for five or six of them, and you're probably going to want to really turbocharger or enlarge or zoom in on that to some degree. That's what AI is so powerful as. When you have an idea of the problems you want to face, asking it to summarize or magnify or zoom in on or focus on the challenge areas, becomes a really powerful tool that helps you make decisions and frame problems. Yep. Okay, what's the second

tip, Mindy. Use AI to draft a draft financial plan. So this is not your final financial plan, but you want them to give you, I keep saying them like it's a person, treat it like a person. Ask questions like, what does a world-class financial plan look like for someone like me? Again, you've given it all your information or most of your information. You've given it your specific scenario. What does a great financial plan look like for me?

Oh, maybe this is something that I love. Maybe it's not. Then you start iterating on what it is you've asked it to do. Ask a question, like, what would an elite CFP's approach to developing a financial plan look like for someone like me and execute that? And you don't have to ask it just one question. Ask it a bunch of stuff. Ask it to throw a ton of things at you. And then you kind of comb through that.

It's, ooh, I like this. I like this. I like this. I can see how this would be valuable too. and then, you know, craft your own plan from all the different things that you've asked. The next tip here is to iterate, iterate, iterate, right? So once you've drafted something that's useful, something that's directionally helpful to you, but I'll literally do sometimes is I'll open up four incognito tabs or temporary chats with

GROC, Gemini, Claude, you know, the latest model, and then GPT's latest model. And I will put into each of them, give me a rubric for a world-class financial plan look for someone like me. just like Mindy said in the last step, using to draft the plan. Then I'll submit the plan that I have, get all four of them at once. And over the course, the next 10, 15 minutes, I get a grade back in suggestions or feedback from it.

And that gives me an enormous amount of input on there. I can read through that and say, I like this, I don't like this, this AI is being overly in the weeds here. And that allows me to iterate. I can take the parts I like from those reviews and feed it back into my core chat with the AI and say, what do you think of this?

Let's talk about this. I like this one. I want you to update this. That iteration process is extremely powerful. You can go through that over the course of a day or two and get a ton of iterations out to get to a really, really strong place. But one tip, though, is to make sure this doesn't go to infinity. The AI will go on forever finding ways to expand or make your plan more comprehensive until you get to, you know, 50 pages of AI slop. So make sure that as you get past those first few iterations where you genuinely want like an open-ended model, make sure you force the review or the AI to distinguish. between factual errors, major omissions, things that weren't included. Preference it has,

or you have on an unknowable or unanswerable challenge, right? It's a preference to do life insurance the way I discussed, not a absolute law. So it may or may not be a factual error to get a term life ladder versus a larger term policy for the full 30-year period. You know, make sure it distinguishes between those and what optional additions it might suggest are. Once you get to a point where it stops beating up on those or you can't find too many iterations or evolutions that aren't preference or decisions you've already made or whatever, then you know you're getting to a pretty good rough draft. A pretty good rough draft. I like that. Scott, what's your next tip? My next tip is to use the AI as a neutral observer. So when I'm using AI, for example, with open AI in

particular, which is, I used to use Clawed up until a couple weeks ago or a week or two ago when the new GPT model came out. I tell the GPT model, I don't, I don't want to to be sycophantic. I don't like it when it tells me that I'm great and my plan's awesome. What a good grade you got here and all that. I wanted to actually produce, you know, real feedback that I can begin to iterate on. So I set the AI to efficient mode. You know, I don't want it to be verbose. I want it to be direct. I want it to be critical or harsh. That, that creates a problem in itself, but I want it to be accurate, as accurate as it possibly can. So I go into the settings and change some of those. And then I ask it to provide an opinion before, like, you know, abuse incognito mode.

So I say, a household like mine should spend what on groceries or what on electricity or what on these items here. And then it provides that answer. And then I submit my data to it so I can compare it without it anchoring to me to tell me something I want to hear. Because that's one of the problems of these data models that they want you to keep using it. But if you can get it to anchor and provide an answer first and then compare yourself to that answer, that will give you a lot more power in these processes and will expose a lot more of your weaknesses. What's the next tip, Mindy? Ask specific to you questions.

You can use AI to help you create a budget, especially if you're in the beginning stages. Upload your bank and credit card statements and ask them for spending habits and potential spending leaks. Ask it for help determining your asset allocation. Again, these are my goals. This is where I'm starting. Where should I be putting my money based on what I want to do? What accounts should I be putting my money based on what I want to do? What accounts should I be putting my money based on what I?

I want to do my 401k, my Roth IRA, et cetera. And you can use it to ask specific to you questions when you're faced with unusual scenarios. Let's take our couple who decided that, in fact, their partner could decide to quit their job. But that partner was the one providing health insurance. They usually have the option of Cobra, which is continuing the health insurance you had before,

but you're probably paying the entire premium versus going out on the exchange. You can ask AI to run through all the insurance. scenarios, run through the costs, and give you a good idea of what would be the best choice for you. It always sounds like, oh, just go on the exchange. It's going to be so much cheaper. I actually had a friend. They had had a baby that year. They had almost reached their entire out-of-pocket max spending, and it was July. So they weren't sure if they should go on the exchange or go on Cobra. Cobra turned out to be the best choice for them. And then they had a bunch of like extra medical expenses that were essentially paid for because they had hit their out-of-pocket max already.

Just to piggyback on this analysis of asking the eye for specific to you questions, there's kind of two use cases for this. There's like a use case for the incognito mode where you're saying, hey, I don't want the A to know it's me and what my situation is. I wanted to evaluate objectively or as objectively as I can what a household of this type will spend in these areas on the situation. That's a great use for incognito. For the persistent chats, the chats that are stored in memory or a project, that's when I want to ask, compare this to last month. or for my situation, what should I be doing here? Give me a protocol, for example, to maintain my lawn or to set the thermostat in my household to reduce my ongoing monthly energy expenditure without changing my quality of life.

Those are great things to ask the eye for how to do. But when you want judgment, I usually like to go in the incognito mode because that I believe produces a more balanced viewpoint. And it's not anchoring to the discussions we've had. I think that filing my taxes is among my least favorite activities on Earth. That's why we've partnered. with a new tax planning firm here at Bigger Pockets Money. They're a tech forward AI integrated CPA firm that works with high income business owners

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trips, family, wellness, that's brought me a lot of value. Longangle is a vetted community of 8,000 or more entrepreneurs, executives, and investors who came for the financial conversations and stayed for everything else. Membership is free for those who qualify. Apply at longangle.com slash money. That's longangle.com slash money. Scott, do you have any more tips for using AI to help you with your financial independence plan? I think that the AI can really help you with your investment philosophy and or your investment

thesis that you come up with. So for example, one of the things I find really challenging is who was a gentleman we had on Mindy recently who had the wonderful investment philosophy discussion grounded in Bogleheads? That was Bob Haynes. You know Bob. Bob came on and provided a really wonderful investment philosophy. And for Boglehead, it's very simple. There's no real need to build a better investment thesis. Where that breaks to some degree is when you have other assets in play, right? And so many bigger pockets money listeners have a pension or have a real estate portfolio or a small business, or equity in their company or some tale that is different from a stock bond portfolio or stock portfolio in their various retirement accounts and all that.

And so that requires some thinking to build an investment philosophy that mapped to the reality of what you have. Even if you want to get to a Boglehead philosophy, there needs to be a bridge that helps you do that tax efficiently over time. That's where an AI can really be helpful is, you know, take the Boglehead philosophy as it exists in the Boglehead Forum or in Reddit and help me draft something that gets me there. or help we draft something that's relevant in my situation. And that's the same iterative process that we went through in some of the other items.

And then if you're going to make side bets, I think it's a good practice to get into the habit of building an investment thesis. And I'll tell you what, AI has been very powerful for me in helping me draft better investment thesis. They'll probably still be wrong. I'll probably still lose a lot of money. I don't to perform the index. But at least now I've got a document that says, here's my thesis. Here's why I believe it. Here's what I'm going to do.

Here's how I'm going to cap my exposure. here's what would prove it right, here's what would prove it wrong, here's when I will enter or exit across those. And I have those documents now for my office investment play. And so I can laugh myself with much more conviction in a few years after having drafted that. And again, you submit this and say, what does a good investment thesis look like at a, you know, world-class institution, condensed the two pages for this particular process. And in a few hours, if you're going to commit serious capital, you can get something that will help you at least poke holes. You know, again, you submit your thesis against that rubric. And it will poke holes in it.

you what it likes, what it doesn't like and what's well supported and what's not in your research. So I find that to be very helpful if I'm going to make side bets, which I do. And I use that as part of my process. Well, and this is just another tool in your arsenal to help you on your paths to financial independence. I think that there's a lot of benefits for using AI to help you just think through. I mean, AI can calm the entire internet in a split second. Maybe not a split second, but they can calm the entire internet a whole lot faster than you can. It's like a turbo boost to your financial plan. That's what I think it is. I think it's a trooper boost to your financial planning process. It is not a substitute for a professional advice and it can make big

mistakes. But I think if you treat it as, here's how I'm going to build a really powerful rough draft of various financial planning artifacts, I think you're going to get very far and you're going to avoid some or a big part of that risk that comes with AI being preposterously wrong or hallucinating or doing bad math. because you're treating it as a draft, and you're going to verify that before you act on it. I think if you treat it that way, it can be exceptionally powerful for you. So I think I would encourage folks to try out some of these. Again, it depends on your comfort level with AI in terms of sharing information,

redact the information or make-up scenarios that are intentionally different from yours. If you would like, I think you might find it a very valuable thought partner. And I think you can get pretty far these days with the free models on some of these and even further with the frontier models. For a single actionable step following this, go to biggerpocketsmoney.com slash resources, download the personal financial statement. It's a spreadsheet. It's just free. There's no email required. Download the goal setting template. And that's it. Just take those two documents. You can redact them or put in intentionally different numbers. You can put in an intentionally different vision or whatever. So the AI can't recognize that it's you if you want. Or you can put in your actuals. And then upload those to the AI and ask it for that first draft or a financial plan. That's effectively. what I have done to a large degree to draft and iterate and get to the current form of the trench

family financial plan. It was literally like the process and then I went through many of the tips that we just discussed. I'm probably also missing some. So again, if you have better tips, if you have different ways you're using the AI, please let me know. I'd love to hear I'm at Scott at Pickerpocketsmoney.com. I'm learning about this every day. I think the field is evolving rapidly. But that's what I do.

Scott, that's what I was just going to ask. If you have any tips that we didn't share on this show, please reach out and let us know so we can update this show. And all of these ideas are available as a document on our resources page called AI for FI. So you go to BiggerPocketsMoney.com slash AIFORFI and you'll be able to download this. It's also in the resources page. And guess what? That document is an iteration. So we're going to post one and our best, our best iteration we have now. We're going to get a feedback from you and we're going to update it in a few

weeks or a few months as people say, oh, I like this prompt. Oh, that is better than what we had there. Oh, implement this. Oh, we upload it to the next generation groc model that comes out in six months. That's way than what we have currently. And it evolved it. Like, that's, that's what AI is and that's the best way to use it. I think it's never finished. It's always in the latest iteration, but you can get from nothing to pretty good, very fast in today's world. Unbelievably fast. That is what is shocking to me is how fast it actually is. And if you want even more financial independence information like resources and calculators and templates, you can go to biggerpocketsmoney.com and find these on our resources page, biggerpocketsmoney.com

slash resources. We also have more financial independence information if you follow us on Instagram, Facebook, or YouTube at Bigger Pockets Money. All right, Scott, should we get out of here? Let's do it. That wraps up this AI episode of the Bigger Pockets Money podcast. He is Scott Trench. I am Mindy Jensen saying catch you later, Tater. You know that feeling you get when checking your finances means logging into five different apps? That's why I use Monarch. Setup takes about 10 minutes. You can link your accounts and everything you own and owe lands in one clean dashboard,

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