Category: Expert Opinion

How AI Is Helping in Tax Planning and Smarter Charitable Donation Valuations

     
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      In this video, Seth Fineberg speaks with Todd Gray, Founder and CEO of Value Insights.AI, about how AI can reduce repetitive work and help tax professionals focus on higher-value services. They discuss how AI-powered tools such as ValueInsights.ai can simplify charitable donation documentation, improve tax preparation, and make firms more efficient.

      Drawing on more than 24 years of experience as a CPA and sole practitioner, Todd explains how he built ValueInsights.AI to solve a real problem he faced in his own practice.

      He also shares why accountants should embrace AI as a tool that supports better advisory, stronger client relationships, and a more efficient tax practice instead of viewing it as a replacement for their expertise.

      Video Transcript

      Seth: Hi again, it’s Seth Fineberg for Ace Cloud Hosting. I am once again very honored and privileged to be talking to a practitioner that I know in the space who has built something really cool and we’re going to get to that.  

      But I wanted to personally introduce you to Todd Gray, a CPA in the San Diego area. Todd, say hello, man.  

      Todd: Hello. How are you? My name is Todd Gray. I am the founder and CEO of ValueInsights.AI and as Seth had mentioned, I’m a 24-year veteran CPA with the tax practice here in Carlsbad, California.  

      Seth: Yeah. So you, really kind of jumping in Todd, just tell us a little bit about the kind of work that you do as a sole practitioner.  

      Todd: So as a sole practitioner I work with individuals, small business owners primarily. I’m intimately tied into tax planning. I have a fixed fee structure. So included in that is emails, phone calls. But more specifically I’m answering questions throughout the year. I’m providing advisory before it was advisory on its own, because I think I’m most valuable in my expertise in my advice.  

      You know, I would rather have clients make good decisions midway through the year, then find out about bad decisions at year end when I’m doing the tax return. So I’ve always kind of you know declared to my clients of how valuable I am throughout the year not just the tax return.  

      Seth: Excellent. So our overarching you know, kind of theme today is really how Tax Pros can you really continue to add value, particularly in the age of AI that we are entering now? You are sole practitioner and like many in the space, you know what’s been the most challenging aspect of your work and how have you handled it.  

      Todd: So as a sole practitioner one of the main kind of I would say pinch points is just two main things technology. And, you know, in the age of AI, technology is changing all around us. And without colleagues that, you know, in a big firm, you have you’re surrounded by colleagues all the time.  

      Seth: You have teams. 

      Todd: Yeah, you have teams and you have maybe a dedicated person that all they’re doing is keeping up with publications and you know, blogs and, you know, going to seminars to learn about the latest and greatest and the best things that are coming online both now and in the future.  

      Well, as a sole practitioner you know, your days and your hours are you only can get through so many things. So one of the things that I’ve done is branched out. I’ve joined networking groups, you know Jason Staats and Realize Group, Logan Graf and the Counter Community.  

      And all of a sudden I can align and tap into the expertise of all these other sole practitioners or small firm owners and even big firm owners, and find out what they’re using and what tools they have that I may be able to tap into. 

      And with all honesty, there are still times where the cost benefit still doesn’t make sense as a sole practitioner but at least I know kind of what might be available and how we could use it.  

      Seth: So you’ve leaned into charitable donations for your client work. Tell me why and meaning you know what prompted it and anything, you know, kind of in the current tax code because it definitely feeds into what you built, which we’ll get to in a moment.  

      Todd: Yeah, absolutely. So, the ValueInsights.AI app it’s a web based app. It sourced from me trying to fix my own problem first. I’ve been doing this for a long time and for years and years I would have clients that would come in with these non-cash contribution slips, you know, Salvation Army, Goodwill, disabled veterans. 

      Seth: Maybe they filled out themselves  

      Todd: Well, no, because they’re required to get that contemporaneous acknowledgment. But a lot of times that’s a date. It’s a name and a couple boxes checked but it never really disclosed what it was that they gave none of the details about what it was. You know, like you know, it’s just a couple boxes checked, it’s household items, it’s electronics, it’s furniture. 

      And so, with technology and just with my own frustration, I reached out to a client of mine who was also an app developer and web developer. And so, we developed a web-based app where you can use your phone. Or if you take photos with a camera, you know, you can upload photos and have a full valuation report for every item that you donate.  

      And the main goal of that was to create a paper trail to have something that was identifiable, that was you could substantiate it, you could value it at the fair market rates in terms of comparable sale. It goes out to the market and it says, I found this couch, and this couch is being sold on eBay and Facebook Marketplace and all these other and then pulls those values back, and then it produces a valuation report with an analysis of both the condition and then compares it to these other comparable sales.  

      Seth: And it uses AI to do that.  

      Todd: And it uses AI to do that. And so now it’s embracing the technology available and the resources available to search for both current sales transactions as well as prior sales transactions, and then pull it into a written concise, identifiable report that, you know, the goal is to have that exported and be able to pull that into a tax software for the tax practitioner.  

      But if nothing else, that the client now has a written documentation of every single thing that they donated and then have higher values because of that. It started from me trying to fix my own problem but really shifted to I want everybody else to save.  

      It drove me crazy for clients to pay too much in tax, and for tax practitioners to be in the position where I don’t want to guess. I want my client to come with realizable, identifiable, and reasonable documentation.  

      Seth: Understandable. And that’s, you know, the nature of the work that you do. So I’m curious how a tool like ValueInsights.ai helped add value to your business, to your practice, and possibly even other practices that you know, they are using it.  

      Todd: So for my clients in particular, I just gave them a tool that in most cases is doubling, if not more, the value of every item that they donate. So traditionally, the IRS has coupled with Goodwill and Salvation Army and other organizations, but they’ve come up with a thrift shop value listing.  

      And those listings are very conservative. And they just don’t reflect the fair market value of those items. You know, my clients they don’t have $8 shirts. That’s just not. But if you go to the Goodwill listing it’s anywhere from $3 to $8. 

      Seth: It’s Goodwill so. 

      Todd: Yeah, because that’s what they feel they’re going to end up selling it for. So that’s the value they assess it at based on thrift shop value.  

      Seth: Right.  

      Todd: But the IRS defines comparable sale as what a willing buyer and a willing seller even if they don’t complete the transaction would value that up. And so therefore we go out and we’ve specifically set the AI to look for those comparable sales and pull them back in into that written report.  

      Seth: Right. And that, you know, records it. And then you can, you know how does it work. So then the client will kind of come back to you with not paper receipts or paper forms, but 

      Todd: Well, they still have to have the paper forms. We’re actually working. Yeah. We are actually working on a, the ability to actually take a snapshot and upload that into the app as well. So you can couple that transaction into one singular thing. 

      So if you donated ten items and you’ve got the contribution slip from, you know, the charity to be able to upload that and kind of combined it into to one singular transaction. But in terms of advisory, this is a tool that now helped me do my job better.  

      I can generate more value for my clients. I’m going to have a more efficient tax return because I’m not having to follow up with the client and say, yeah, you’ve got these ten contribution slips. What did you give? What was the fair market value, that back and forth. 

      This app eliminates the majority of that if not all of them. So, it really helps me do my job better and more efficiently.  

      Seth: And you’re kind of seen as a hero because at the end of the day, like you said it really bothered you that you know, you’re seeing clients that just, you know, you felt like, wow, I feel like I could save them more on their taxes.  

      Todd: Yeah. Call it idealistic. It bothered me that my clients were, were incurring more tax than they needed to.  

      Seth: Yeah. You know, other factors and such. Have you heard similar stories to from other folks who are sharing this with their clients too. 

      Todd: So, what’s been really I say interesting, but it’s been funny is this is a pinch point for every single CPA, every single tax preparer. When I bring up the client that walks in with the stack of contribution slips and the lack of documentation, they all just laugh because it is a problem and it has been a problem. And I wanted to fix the problem.  

      I wanted to enable a tool for the tax preparer and for the taxpayer where everyone wins, the taxpayer has a larger deduction and pays less tax. The CPA or tax preparer has a more efficient and more valuable tax return that hopefully they can charge more for. And the only one that loses is the IRS and the state governments.  

      Seth: So that’s I mean that’s some great real-life accounts of how technology and AI is playing a bigger role. How do you see tax work evolving in the next few years? Kind of hard to really see well beyond that. But just, you know, you’ve been doing this for a bit. How do you see it evolving in the next few years?  

      Todd: Yeah, I mean, I’m excited to see where we’re at AI wise and just compliance wise over the next, let’s call it 6 to 18 months. We have been at breakneck speed when it comes to, you know, what Claude can do, what ChatGPT can do. And then everybody building stuff off of those.  

      I think it’s going to be really interesting. I think the compliance side is going to streamline. I think we’re going to have either agentic you know, preparation or, you know, document import into things. 

      I think there’s going to be a lot more analysis, review. I think a lot of those smaller steps in the tax preparation is going to go away. I think we’re going to streamline a lot of those things, but that also enables us to do the more valuable things to be reviewing returns and reviewing the work and advising as to how to structure things. 

      To me, as a sole practitioner, one of the biggest things that I run into is the daily burn of minutes and hours on small tasks, because small tasks build up to big heavy backpacks. And I need to lighten my backpack. Because that takes me away from being able to add value to all of my clients. So, if I can eliminate some of those smaller rocks, that’s a great thing. And it allows me to be more valuable to my clients. 

      Seth: Excellent. Thank you, Todd. What would you say. And this has been very insightful. If you had sort of an encompassing statement that you wish to make to your fellow practitioners about AI in the tax base, what would you say?  

      Todd: Embrace it. This is a powerful tool to make all of us better. You know, I’ve used the example that, you know, the tide raises all the boats. Well, let’s embrace this because it’s going to give us a stronger, better, more efficient business.  

      And there’s I don’t feel threatened by AI that it’s going to replace me. I think if anything, it’s going to trigger more conversations and more things where clients are coming to me and saying hey, you know, I heard about this thing, or you know, I think it’s just going to free up time.  

      It’s going to make it more efficient and more effective advisory is really where I think we’re going to end up, because I think a lot of the compliance side, a lot of those small rocks like I said I think are going to get addressed with some of the technology and really allow us to use what we’re most valuable, our brain.  

      Seth: Todd, thank you so much for your time today and thank you to Ace Cloud Hosting and also any Tax Pros out there. Definitely check out ValueInsights.AI for your clients that have charitable donations. 

      Todd: Thank you so much, I appreciate it.  

      Seth: Thank you. 

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      About Julie Watson

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      Julie Watson loves helping businesses navigate their technology needs by breaking complex concepts into clear, practical solutions. With over 20 years of experience, her expertise spans cloud hosting, virtual desktop infrastructure (VDI), and accounting solutions, enabling organizations to work more efficiently and securely. A proud mother and New York University graduate, Julie balances her professional pursuits with weekends spent with her family or surfing the iconic waves of Oahu’s North Shore.

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