Why You Can’t Trust AI with Your Money (Yet)

One of the reasons why they come to us is to figure out, like, how much is my business actually making? I can't really tell, so I don't know how much to pay myself. So it's like this vicious cycle, and it's really hard to get out of it without help. It's like, kind of like getting mental health help.

Welcome back to entrepreneur school. I have another incredible guest episode for you today, and I'd like to you to meet Serena Shoup. She is a CPA turned bookkeeping CEO, a mom of three and the powerhouse behind, of course, financial and the ambitious bookkeeper podcast, she left corporate to raise her second daughter and built a thriving business from her kitchen table because, you know, spreadsheets and sticky fingers can totally coexist. Now she's on a mission to help entrepreneurs ditch the money shame, understand their numbers and run profitable businesses with confidence. If you have ever said, I'm just not a numbers person talking to me, Serena's here to prove you absolutely can be welcome. Serena, hi.

It's so nice to be here. So nice to see you again. I feel like we just chatted like a week ago, which we probably did.

We did. We recorded for your podcast. So make sure that you go listen to that one as well. Depending on what time it's out, I'll make sure that the link is below to that episode too. Okay, so Serena was just telling you before. I've been doing this fun thing with my guests lately where I'm like, welcome to the show. What is your soapbox or hill that you would like to die on. Let's go there right away and start there

honestly, like the I could go so many different directions. So I'll try to keep it narrowed down to one, one of the biggest issues that I see in the financial professional world is the way that professionals in my space, I won't call out specific people, because this is kind of like across the board. Honestly, sometimes it's a CPA, sometimes it's a financial advisor, sometimes it's a bookkeeper, tax preparer, whatever it's like they I don't know. I don't know where this comes from, honestly, but the shame and the condescending tone towards people when they like, come to you with questions like, as a professional, it's our job to like this is why so many people have fears around money or getting help around it, because they're afraid of being talked down to, and then we go and do that, yeah, and, like, basically shame them for wherever they're at, or the questions they have or whatever. And so that is, that's my soapbox that, since, you know, I have the other podcast, the ambitious bookkeeper, I coach and mentor other bookkeepers and accountants as well. One of the biggest things that I talk about is like just meeting people where they're at and not not being that type of professional, which is honestly very unprofessional, in my opinion.

Oh, it's so true. It is a very delicate area when you're working with people and their money and all of the things that they've done or haven't done, and there's so there's definitely the potential for your clients and listeners and myself and everybody included to feel a little bit of shame if it's if things aren't like all amazing.

Yeah, and it's crazy, because financial professionals can sometimes be the worst around their money mindset and even managing their own money, it's kind of like the cobbler shoes situation where it's like, this happens in every business. We are not exempt from it. And so when you look at it that way, sometimes, like, now I'm like, Oh, well, maybe they're just actually projecting their own shame. True not to get super deep or anything, but we're here be part of it.

Yeah, we're here for it. What are, what are some of the top challenges that you see some of your clients coming to you with when it comes to managing their money for their businesses?

Yeah, I would say in the early stages of business, one of the biggest challenges is usually has to do with like keeping their finances separate, which seems like a basic topic for a lot of us, but it's a challenge for people, especially if they started their business as a side hustle, and they weren't sure if they were going to it was going to take off, and so they didn't really, you know, you sometimes are like, I don't Want to build the system because I don't know if it's going to, like, work out. And so people do the same thing with their money. So they commingle the money, they keep running everything through their personal account, and then you get into a point where you're relying on the business for your income. I've seen this across multiple clients that have come to us initially. There. They get to a point where they're starting to make good money through their business, but they haven't separated things yet, and so now they're afraid to separate them, because they've just been running everything through the business account, or vice versa, everything through the personal account. And they don't know how much to pay themselves because they've been commingling everything, but they know the business is bringing in money, so they just pay themselves by like, using the business credit card or using the business debit card to pay for groceries and things like that. So that can be kind of a difficult thing to untangle. It's not impossible, but it usually requires, like, let's cut off the bleeding and separate things. And you have to just like, buckle down and get on board with like, keeping things separate, but that's part of, one of the reasons why they come to us is to figure out, like, how much is my business actually making? I can't really tell, so I don't know how much to pay myself. So it's like this vicious cycle, and it's really hard to get out of it without help. It's like, kind of like getting mental health help, right?

Sometimes you need the actual medication to be able to stop whatever is getting in your way, so that you can then, like, get outside and take a walk instead of laying a bed. You know what I mean? So it's, it's very similar to that, like you have to get help. Let us, like, help you and figure out how much your business is actually making it's a little bit of work when things are comingled like that. But it's not impossible. It just takes a team effort.

That's not what I thought you were going to say to that question. Interesting. I thought you were going to talk about, like, profitability and profit margin and actually knowing if you're making money. Because sometimes I feel like we can be like, Oh, something came in, and then I just like, oh, I spent it right away.

That's also a thing that happens, like a little further on in the business journey. It depends on where people find us, right? Some people come early on when they're starting to make money, but they're not sure how much to pay themselves. And then issues like that, where they're like, Okay, now I'm ready for growth, but I don't know if I can afford to hire someone, so then we have to look at the profitability and all of that as well. So there's definitely different stages. That is one of them, for sure.

Let's talk a little bit about your journey into into this and because you kind of, you have, like, two businesses that you're running at the same time, but very like intentionally connected, and that you have a CPA firm and you're teaching others how to be financial professionals, bookkeepers, etc, yeah, tell me how you got there,

yeah, so Not on purpose,

yeah, the best stories.

decided to hire a bookkeeper. And so that bookkeeper is actually still with me to this day, and she's also a mom, and we used to just get on Zoom calls in the evening and CO work and work. Through the stuff together when our kids were asleep, and yeah. So the business continued to grow because I had more capacity to do that. And at the same time, I was part of these online communities, aka Facebook groups, right back when Facebook groups were very, very poppin, and and there was, I was a part of several Facebook groups for bookkeepers, as I was kind of building my my business, and wanting to poke around and see like what other people were doing, what were some of the struggles they were having. Other people had solved my issue, and I noticed that the same questions were coming up over and over and over again, and I was the one answering them. Even though I was like, kind of look in those communities for my own support, I was the one that was actually like answering the question. So I was like, okay, maybe I have figured some things out, and maybe I can share this in a better way. So I instead of repeating myself over and over again, I started just blogging and just documenting some of the systems I had created and processes around onboarding clients, and processes around getting clients as an introvert and things like that. Because I don't know if you know this, but a lot of us are introverts in the busy being in finance world. So I was just kind of documenting that. And anytime I would see those questions come up, I would be like, Hey, I wrote a blog on this because, like, I'm passionate about, like, also helping others in this space. And I just started kind of building it that way. I then put together, like a PDF, and it was like $27 and it was basically like a to z, like, how I started my bookkeeping business, like the checklist. Because there was people coming into these groups being like, I have experience with accounting or bookkeeping. I want to do this

on the side, but I just don't know where to start. So I was like, I could literally just make a playbook and sell it. And so I did.

And I love this story, and I love that you're like, I feel like we all need to hear this again and again, just the whole, like, the the stepping stones of I did a thing. I figured it out a bit. Other people asked me about it, so I started telling them. And so I started, like, shifting into doing that. I've, like, always wished that that was my journey. It was not,

yeah, it was, it was interesting, and it's, it was mostly born out of, like, truly wanting to help others in the space be better at helping clients. Because a lot of I would get clients that had had previous bookkeepers and things were just a disaster. So I was like, Well, I can't serve literally every client out there, so the next best thing that I can do is try to make sure that anyone I come in contact with in my space gets a little better at their job. And so that's kind of where the passion was of, like, ultimately, like, everyone's benefiting if I help and like, share what I've learned along the way. And because I came from a corporate background, some people are self taught, and they didn't have a mentor to, like, share this wisdom and these processes and these best practices, so I just kind of felt called to,

I was just going to say, too, from a business model perspective of running like a consultancy, essentially practice where you do the work for your clients, and the scalability opportunities Become hiring basically so that you have more capacity, and then adding on another element where you're doing mentorship and teaching and training, and that creates that one to many opportunity, right?

Yeah, yeah. And it's not like I set out to do that. I wasn't trying to, like, add another revenue stream. I was really just like it was my heart, like I just wanted to help people. And I also, around that time, discovered that I really enjoyed parts of the bookkeeping business, but not all of it. And one of the pieces that I did not so much enjoy was the repetitive nature of doing the bookkeeping every month. But I loved helping to mentor someone else to do that, and like, double checking their work and just being there as a sounding board and providing a job for someone as well. And so I just kind of like jumped on that opportunity, of like, I can mentor other bookkeepers and people within my own business and grow both. And it was very fulfilling. So yeah, that's kind of how the second brand was born, and that took off in the timing. There's always a timing and luck of the situation, right money I've created that. PDF. The way that I did it is, at this point I had had like 100 subscribers to my blog, and so I had a little bit of an email list, and I really didn't have an end, necessarily an end goal with that, it was just like, if you want to be updated, every time I post a blog, subscribe to it, like the old fashioned way of doing things, and it was on Squarespace. And so I had, like the the minimum email marketing thing on Squarespace at that time, and it was also on my firm website. So there was, like a tab for bookkeepers and a tab for clients, and I created that PDF. But like, first I pre sold it, and so I emailed every the, you know, 50 or 100 people that were on my email list. I don't honestly, it wasn't even 100 at that point. I think it was more like 25 or 50. And I was like, hey, people have been asking, like, for a checklist, basically, of like, how do I get my business started? If you are interested in that, here's a PayPal link. It's going to be $27 and after the first person buys it, I will create it, and you'll get it in one week,

Can we also just have a moment to talk about how much easier that would be right now? Like, how much faster you're like, Oh, you needed, like, a graphic designer and like the to make the checklist that you would like be able to build with AI support in moments, and Canva templates to just pop it into and like the whole thing would be done in half a day.

Yeah, and we did. We I was using Canva at that point, but I don't feel like the templates were as good as they are now at that point, and also I just was really inefficient with it, because that's not my background.

Totally. Yeah, yeah, but, oh, I love that. And yes, and thank you for also like being transparent about the timing of it too, because that's a good reminder to people that it's there's always, like, an extra piece. But it was because you were moving in that forward direction already. You had the vision. You saw the gap, like the market opportunity. These are all still important aspects to have kind of behind you as you're moving forward, and then eventually, and I always say this, eventually, it's going to take off, right? Yeah, if you don't quit, you won't ever fail.

What are you seeing in your clients? And I think this is an interesting thought leadership opportunity for you to, like, talk about, like, industry shifts, and how are, how are businesses that are primarily built on, maybe courses and training and that kind of like expert led, which is a lot of my listeners as well. What are what are they doing differently in order to be financially successful?

Yeah, and that's part of being a savvy business owner, is watching the trends and seeing what like, not necessarily like to follow the money, but like, that's part of our job, is to pay attention to what people want and where the economy is going and where the market is going. So I think there's absolutely nothing wrong with jumping on I don't think it's a trend. You know what? I mean. It's not like a trend in the sense of like a Tiktok trend, but like a trend in business is like a bigger thing. Dying than a Tik Tok turn. Yeah, there's nothing wrong with following where technology is going otherwise. Just like everyone has probably used this example a gazillion times right now, just like, otherwise, you'll end up, like a blockbuster, like we're not changing, and then you die.

Yeah, and it's because, like you said, it's built into the buyer's expectation. The expectation is now we have tools like AI that will do things for us, that can make things faster. So if I'm choosing as a buyer between a program or an offering that integrates that or doesn't, I know where I'm what I'm going to choose, yeah,

yeah, and that, like that brings up something that I was thinking about or I had posted about on threads a while back, because I agree people are expecting things to be faster now because of AI. So I was like, Okay, how can I incorporate this into my firm and our offerings. They're just starting to roll out some AI features in the software that we use. I don't use QuickBooks, that's the other that's my other soapbox. Save it for another day. But I use a software called Xero. QuickBooks has already started to roll out their AI features. Xero is also starting to roll theirs out, so I haven't done a lot of testing on it yet. As far as the transactional work goes, I have tested it out on some of the other non transactional like research within the system. You can ask it to, like, create invoices, and you can ask it to look up how much does this customer owe me, and things like that. It's still not great on that regard. Have not tested out the actual transactional work of it yet, but I'm preemptively preparing for rolling that out by, you know, getting feedback from the marketplace. So like, what would that do for us? If we can get the transactional work processed quickly, then essentially, we should be able to deliver reports and insights to our clients more quickly. But there's still a layer of review that I will always do on the financial stuff, because the the experience I've had with popping financial information into chat GPT or using AI for it is sometimes it just, you want to talk about non numbers. Person, chat, GPT is not a numbers. Person, simple math. We'll get the best of it. And so, like, I don't trust it yet on that regard. So we're still, like, no matter how much we use AI, I do still think human touch, obviously, but also like oversight and review, just like I would do for human bookkeepers, we have a review layer, and so we're going to treat the AI situation just the same. Have a human layer of review and delivering

results to clients, and have that human touch. But I was I posted something on threads about, like, you know, how important or how like, excited would you be about like, I don't remember how I worded it, but basically, I was like, what if we offered financials within five days of the close of business? Most of our clients don't get financials until the 15th or the 20th because it that's how long it takes us to get information from them, to get the reports and all that kind of stuff. But if we can implement, if we can get our systems better using AI or whatever, get our clients more on board for faster results, then wouldn't, is that what they're expecting? Would you pay more? And then someone was like, why wouldn't you just have ai do it? And I'm like, the whole freaking point, but there Yeah, to be a layer of review, so it can't be immediate.

100% I was just having a conversation with somebody else as well. There is a misconception that AI is supposed to be a know all like truth finder, and that I think is entirely the wrong way to look at it. It is a support that can do things way faster than you when you give it the instructions that you need, like so you are still the human who provides all of the context and the details and the tweaking, and then also, like you said, you are still the human that needs to do that review layer before it goes out to anybody else. But I love how you're thinking about adopting this, because what it does do is allows you to be providing more value to your clients, and that should be how it's being integrated. So how can we do things a little bit faster so that they can get insights that will help them make better decisions more quickly, or like, whatever is the problem that you're solving for your clients?

Yeah, yeah. That's, I mean, that's kind of where I see things going, and some clients what are going to value it, and some aren't. So that was basically what I got from that thread. Response was, like, that's fine. Like, if you don't value the human touch in the bookkeeping process, then you're not. Client. If you believe AI can completely handle your bookkeeping on its own, have at it. But good luck, right?

Well, and for some people who maybe have, I don't know, a simple business, like some basic expenses and whatever, but if you are wanting to, like, really analyze your information so that you can make, you know, big expenses make sense, or hiring or growth decisions like, which is like the next level of probably what's scary for a lot of people to think about being in a position to do that. But at some point, you know, we're putting on the big girl pants, and we're going to have a business like that, if we're really stepping into our own ambition. Yeah, then, then we need these types of insights and that specifically, like, that's definitely an area that I know I don't look at my numbers enough. Either it's kind of that out of sight, out of mind. I've talked about this openly on the podcast before. It's like, once a year or once a quarter, I'm like, okay, cool. Or, you know, my measure of success sometimes is, well, I didn't put any personal money into my business this month or this year or whatever. So, yay.

Yeah. Well, that's a start. That's totally fine. We all go. I go through phases too, where I avoid looking at my numbers, because I kind of know what's going to be hiding under there. You know what I mean? And so no, like I said before, no one's exempt to it's human behavior, like, if we know something is probably not right, like, sometimes some of us will avoid it, and it's one of those things that I have to, like, it's just like, starting the gym again. It's like, no shame, like, it's been two weeks since I've been there, but I went back Monday and, like, nobody cares. I'm the only one that cares, and it's totally fine that I'm beginning again, and I look at the money stuff the same way. Like, every time I just make that decision, it doesn't have to be at the beginning of the month or at the end of the month. It's just like, Okay, it's been, like, a week since I've checked in with my numbers, or a month, or however long, but like, at least I'm doing it now, and now I have information, and now I have, you know, I can make better choices and not judge myself in the process, because that really doesn't help anything.

Yeah, absolutely. The money mindset in that. That's why I understand now, why they talk about like a relationship with money and a relationship with food and whatever relationship with your health and exercise, and that's

because it's continual.

Yes, yeah.

It's not like you'll never be able to just set it and forget it, because that's how things get off track.

Yes. Oh, I feel like that's the whole theme of this conversation, right? It's like the actual like you need to understand your money piece and the in the market, and these are all tied together, because that is it's there to help inform the decisions that you make as a CEO,

yeah, yeah. And no decision can be made in a silo either. So it's like, you have to consider what's happening in the marketplace. You have to consider the behavior of your customers. You have to consider your own finances like and you have to look at everything all at once in order to really make a decision. And that honestly, can be very overwhelming and isolating as a CEO, and that's one of the things that we provide our clients, is the space to talk all that out, because typically, when you run a business, most of our clients don't have, like, partners or anything in the business. It's like a solo S corp or a solo entrepreneur, maybe a husband wife situation, but for the most part, there's, it's just a single, single member LLC, and they don't have someone that knows all the things that we know about their numbers that they can have those open conversations with. So a lot of times it is like, we're just a sounding board of like, okay, well, here's what the numbers say. Like, let's look at all these revenue items and decide, like, what was like, did that? How much time did you spend on that one? Is that? What lights you up? That's the money maker. But that doesn't necessarily mean that's, like, the long term thing or whatever, and we'll just have discussions around different investments they've made in their business. Like, did you see an ROI on it there? It doesn't appear on the P and L that you got an ROI on this investment, but it doesn't mean that there wasn't one, because it could have been that they bought back their time. Yeah, what I mean? So it's, there's always more context than it's a discussion with the client, for sure, and that's one of the things that I love doing, is providing that non judgment space for them to talk it out. And a lot of times I'm not providing any advice. It's more like, Okay, here's what the numbers say. Check in with what your goals are. And is this an alignment? With what your goal is. Or like,

for instance, a couple years ago, I had a client who had a membership and was doing some other stuff in her business as well, like a mastermind, a membership, a bunch of different things, and the membership was the main revenue generator and but she was just really tired of running it. And she's like, I know this doesn't make sense on paper, but like, I have to close it down. And I was like, that's okay. Like, you don't have to explain it to me. I'm just going to report the facts that show up on the PnL, and then you get to decide, because it's your business. But like, if you like, I would just encourage you to consider, like, if you do shut that down, you will that affects your bottom line this much. So if you have a different plan for it, great. If you're just trying to run your business like on the side of other life stuff, that's okay, but this is the impact of it, and so now you know, and you can make a more informed decision, instead of just on your gut. Ultimately, she still ended up closing down the membership, and she's replaced some of the income, but now she just works less, and that's okay.

Yeah, and it's so, like, it's so different from what like if it were like a fortune 500 company or whatever, and you have all these stockholders, oh, yeah, have to do the financially sound decision. You can't decide based on your time or how much you like doing something, but that's why we build these businesses, right? So we aren't beholden to someone else's agenda and all of that, like, it's great if we can make a lot of money and it be what lights us up. But sometimes that's not the truth of it forever. Sometimes things change. Seasons of lives change our you know, our kids get older, our kids, yeah, we have more kids or whatever,

yeah, yeah, they are in school. And then you have more time, and you do different things, and you or you choose that you want to do different things. Yeah. So Serena, as we're wrapping up, I want to give you, like, an an exit soap box. What are the your final words or last things you wanted to make sure we touched on, if we didn't cover them in this conversation?

Yeah, I would say, like, if you've been considering some big moves in your business and you do want a second pair of eyes on your numbers, like it's okay to get help. And the other thing too, is my, my other little soapbox is like, if you're not in love with QuickBooks, you don't have to use it just because everybody else. But yeah, and if you if you do have a bookkeeper or a CPA or someone that doesn't that every time you walk into their office or get on a zoom call with them, you feel shitty. Maybe it's time for someone else. And there's definitely better options out there, so I would explore them

so much permission. Can everyone get in touch with you? And I think we do need to say, because you and I are both talking to each other from different countries right now, yes, and I so a good portion of my audience is Canadian. You are in the US.

I am in the US, but I have a great Canadian bookkeeper referral if you want one, and so you can reach out to me on Instagram. I'm at, of course, financial, I'm a little slow to check messages because I'm checking them through many chat because I don't have Instagram on my phone right now. But or you could just go to my website, of coursefinancial.com and there's some different contact methods there as well.

Awesome. Thank you so much. Serena.

Thank you for having me. It was a blast.