Navigating The Pit Of Despair AKA Tax Season with Shannon Weinstein
Do you cringe at the thought of tax season, wondering what ugly surprises lie in store for you? As fractional CFO to growth-minded business owners (and top podcaster) Shannon Weinstein says “You can’t hot glue and duct tape your numbers forever.”
Shannon dives deep into how to set yourself up for a smooth tax season, no matter your business stage:
Why collecting good data is an excellent place to start (and what to do if you’ve been avoiding your numbers).
How one small mid-year ask of your CPA can save you a world of hurt at tax time.
Deciding which parts of your business financial life to handle yourself vs. outsource (hint: If it’s not in your genius zone…)
How to start turning your data into smart decisions that align with where you most want to take your business.
Plus, a bonus guide to the types of financial pros serving expertise businesses and sample interview questions to ensure they’re a fit.
LINKS
Shannon Weinstein Website | Guide | Instagram
Rochelle Moulton Email List | LinkedIn | Twitter | Instagram
BIO
Shannon is a fractional CFO for growth-minded business owners, a CPA and a teacher at heart. Her real-talk and relatable examples simplify the financial side of business so business owners like you can stop stressing and start scaling. She is the host of the IRS’s least favorite podcast, Keep What You Earn, where she releases daily episodes. She is also a frequent speaker in business mentorship communities and masterminds.
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TRANSCRIPT
00:00 – 00:20
Shannon Weinstein: A stress-free tax season is the byproduct of planning and looking at the numbers all year to the point where it’s not a surprise. And I didn’t realize this until I started my own practice that the tax bill was 25% of the problem. The surprise aspect of the surprise tax bill was 75% of the problem.
00:25 – 00:59
Rochelle Moulton: Hello, hello. Welcome to Soloist Women, where we’re all about turning your expertise into wealth and impact. I’m Rochelle Moulton. And today, I’m here with Shannon Weinstein, Fractional CFO for Growth-Minded Business Owners, a CPA and host of the IRS’s least favorite podcast, Keep What You Earn, And kudos to her. She’s landed her podcast in the top 1 and a half percent of all podcasts, which is no small feat. And she aims to bust the myth that all accountants are boring. So Shannon, I’ve set you up now. Welcome.
01:00 – 01:03
Shannon Weinstein: Thank you. And expectations have been set. I hope I live up to it.
01:03 – 01:38
Rochelle Moulton: Oh, I know you will. So 1 of the reasons I was so happy to have you on the show is an episode from your podcast where you describe tax season as a pit of despair for some people. And true confessions, I’ve been down that pit myself once or twice in the course of my business. So I’d love to have you spare our listeners from making any visits there. But I’m also fascinated with how you’ve built your business so far and the path that you’re walking to do that. So let’s just start first with your business. And
01:38 – 01:47
Rochelle Moulton: I think McDonald’s deserves a shout out since it looks like both you and I had our first management jobs there at the ripe old age of 17. So high 5.
01:47 – 02:00
Shannon Weinstein: Yes, I was a baby at 14. Like the day I turned 14, my dad was like, get a work permit, make your own money. And I was cashier and cleaning the bathrooms, like internally grateful for that experience 100%.
02:00 – 02:07
Rochelle Moulton: Well, I’m impressed because the state I lived in, we couldn’t work until 16. So I didn’t start till 16. You were good.
02:07 – 02:21
Shannon Weinstein: Yeah, they wouldn’t let us touch the fries until then. And I couldn’t work past like 7pm. But trust me, my dad squeezed out with all the work he could out of me. He’s like, do the minimum that you can do. And it was just great experience.
02:21 – 02:33
Rochelle Moulton: I second that awesome McDonald’s experience. So what made you leave, you were in the big 4 and corporate America, what made you leave that kind of safe, secure place and go out on your own.
02:34 – 02:59
Shannon Weinstein: It’s so funny, Rachelle, that you bring it up as like a safe, secure place, because it feels that way when you’re in it, because there’s security in certainty, in like, I’m gonna get a paycheck that I can kind of coast along, I can fall into a routine, I don’t have to think too hard. I can kind of show up and do the work and go home. And I just kind of got restless because I think there are some of us who, they just want something more. They know they’re meant for more than the paycheck and the
03:00 – 03:26
Shannon Weinstein: cubicle and that type of lifestyle. And I think COVID really accelerated that because I was working from home in my corporate job. I had started building my business on the side, but I really took it seriously when we went remote because I realized that, you know, this is how it’s supposed to be. We’re supposed to be able to integrate work and life. Like we shouldn’t have to be chained to a desk for 8, 9 hours a day. And then you get to go home. It’s not like school used to be or anything. I go, you can
03:26 – 03:50
Shannon Weinstein: learn anywhere. You can work anywhere. We can be productive anywhere. I said, I’m so much more productive working from home when I can set certain work hours and I can break for the middle of the day to go grocery shopping or do laundry. Then I don’t get stressed out about all the stuff I have to do when I get home and I’m not burning myself out. So long story short, I really wanted that freedom of being able to manage my time effectively the way I wanted to.
03:51 – 03:57
Rochelle Moulton: Love that. So now you’re not a soloist as I understand it. You’ve assembled a team of folks to work with you. Is that right?
03:58 – 04:12
Shannon Weinstein: Yeah, I’m still the primary CFO for all the clients, but we assembled a fantastic team of folks who support me in the marketing and podcast areas, not to mention bookkeeping and other roles as well that will help me from an admin perspective too.
04:12 – 04:24
Rochelle Moulton: So with your business, is your plan to scale significantly? I heard something on a podcast that made me think maybe that was the case. Or do you have a sweet spot that you’re either in already or aiming for?
04:25 – 04:58
Shannon Weinstein: So when it comes to scaling, I define scaling as increasing the output without, you know, basically, I can’t multiply myself. Scaling would include really being able to train up and to build other Shannon’s. I’ve just kind of come down to the process of I want to build the recipes. I don’t want to open more restaurants. Let me say it this way that I don’t want to manage 10 chilies, but I would love to cook up the recipe that a bunch of different restaurants then buy from me. So I would rather license my methods, my systems, my
04:58 – 05:24
Shannon Weinstein: operations, everything I’ve learned, I want to package it for other accountants so they can start their own journey and they can pick their own clients. Because I realized that even my clients don’t want to be commoditized. Like I built a business with intention that my clients aren’t a commodity that can be bought and sold their relationships. So if I were to leave my business and to sell it, I’m like, that’s not fair. My client roster, they picked me, you know, they didn’t pick whoever bought me. So I really take care of that. And I look at
05:24 – 05:41
Shannon Weinstein: that as relationships. And I say, you know what, leave it to the other accountant to build their own relationships. But here’s all the infrastructure, the admin, the operations, and here’s how to run everything I’ve done and a massive shortcut to doing it, which I think is valuable. Plus, it can be sold multiple times. So I figure that’s the route I’m probably going to take.
05:41 – 06:15
Rochelle Moulton: You know, what’s so fascinating about that is I take back what I said that you’re not a soloist. I mean, what you just described is exactly what a lot of soloists in my community in any way look for. I mean, they’re looking for ways to license their intellectual property to leverage it in different ways. So good on you. Good on you. Okay. So before we dive into avoiding the pit of despair that can be tax time, am I safe in assuming that if you hit the pit, right, of despair, that it’s not just about taxes. It
06:15 – 06:21
Rochelle Moulton: feels like it’s a sign that something is going off the rails in your business. Is that true or no?
06:21 – 06:49
Shannon Weinstein: Maybe. So I look at tax season as kind of like the ultimate Weight Watchers weigh in. If you’re from my generation, we’re like that was the thing. It’s kind of like when you come out of the holidays, you put your jeans on and you’re like, oh no, I got to jump up and down and wiggle on the bed a little bit to get into these. And then that’s when you realize something’s wrong. So I kind of feel like When you put the jeans on and they don’t fit, it’s not the first sign you were heading in
06:49 – 07:14
Shannon Weinstein: direction, but it’s the first 1 you can really feel. So it’s starting to manifest the symptoms of lack of responsibility and ownership over your numbers, and it just starts showing up in the way of taxis and stress. It’s just like when you don’t fit in the jeans. In reality, there were lots of things that compounded over time that contributed to that feeling that could have been avoided. But you find yourself there because you ignored some of those other signs. That’s how I would view it.
07:15 – 07:30
Rochelle Moulton: Well, maybe let’s take the opposite approach. What does a mostly pain-free tax time experience look and feel like from the standpoint of, you know, a soloist business owner? Like when everything’s working right, what should it feel like?
07:30 – 07:53
Shannon Weinstein: So I’ll start with what the year should feel like to contribute to that. So there’s a couple of key milestones you want to keep in mind. 1 is, let’s just say it’s post-tax season. And I’ll just start from that point and then we’ll work our way through the year of what it should feel like. And then I’ll go through If that isn’t what your year looked like, what you can do about it, because I know that we’re probably at a point where there’s a little control people have over what’s coming up. So in the course of
07:53 – 08:20
Shannon Weinstein: the year, over the summer, you want to be reflecting on how the taxes went, how much you owed, where you’re at, And you want to have a planning meeting with your accountant to go through any tech strategies you want to be implementing that year that could move the needle. Maybe that’s opening a 401k. Maybe that is offering benefits or just having something in place, like an accountable plan for your S corporation. All of this is like jargon written, but these are the conversations you want to have with your accountant to say, Hey, what can I be
08:20 – 08:48
Shannon Weinstein: doing to plan? And what should I be focusing on for this year? Then you want to have a, and a lot of people don’t ask for this. And we just talked about this before we hit record, which is like not knowing what to order at the counter when you go to talk to an accountant. Because there’s no menu. So here’s the thing. You want to order from your accountant. You want to say, Hey, would you be willing to do a pro forma return? What that means in our speak is a dress rehearsal. So if we can
08:48 – 09:17
Shannon Weinstein: do a dress rehearsal tax return in July or August, which I actually do July and August because I have up through June financials, which means do your books. And we put, we pull at least that through the half of the year, pull your January through June and then essentially double it. Or taking into account other factors, put together an estimate knowing half the year is already in ink and half the year is going to be in pencil and figure out, okay, if we plug this into a fake tax return, what comes out? And now you have
09:17 – 09:48
Shannon Weinstein: a ballpark range. It’s kind of like playing pin the tail on the donkey all year, but the blindfold fades. So right now you’re kind of in the dark, you can kind of halfway see through, and you’re going to plot that pinpoint on the map and say, okay, it’s going to be in this general region. And I think that a stress-free tax season is the byproduct of planning and looking at the numbers all year to the point where it’s not a surprise. And I didn’t realize this until I started my own practice that the tax bill was
09:48 – 10:17
Shannon Weinstein: 25% of the problem. The surprise aspect of the surprise tax bill was 75% of the problem. And I think that if you know, you’re going to owe 50 grand, but you know it 10 months in advance, that is powerful. Yes, we are going to try to minimize that as much as possible. However, the time to minimize it is when you still have plenty of story left to write for the year. You do not want to wait until the book is done. You’ve written it and It’s all in dry ink before you’re like, hey, I don’t like
10:17 – 10:18
Shannon Weinstein: that ending.
10:19 – 10:36
Rochelle Moulton: I’m just curious about something because I’ve never had an accountant actually suggest this to me and I didn’t think to ask for it either. Exactly. So is this sort of a question not only that we should be asking, but that our CPA should be asking as well? Or is this just business owner only stuff?
10:37 – 11:03
Shannon Weinstein: In my opinion, this should be a standard offering for any tax professional. But again, I can’t dictate what other people do. But I do think that you should come informed and say, Hey, I would love it if as a part of your service, and this may come in an additional fee guys, but it’s worth it because I think this is the most powerful tool is if you say, Hey, could we meet in July? Because technically that’s a really slow time for accountants. Like that shouldn’t be a problem. So could we meet in July? And could we
11:03 – 11:30
Shannon Weinstein: go through a pro forma return and walk through like using 1 of the old tax returns and kind of coming up with a ballpark estimate of a range of what my liability might be with all these assumptions baked in, right? We’re saying I fully understand that we’re assuming Jan to June is going to repeat itself the second half of the year, or I’m assuming that these sales do close, right? We all know that entrepreneurship is this journey that’s like always in pencil. Like, we don’t know what’s going to happen. But as long as you’re aware that
11:30 – 11:42
Shannon Weinstein: like this isn’t pencil not pen, it’s better than a blank slate. So I say have something have a ballpark range, don’t hold them to it from an accountability standpoint and like come run at them and say, you told me I was gonna like
11:42 – 11:43
Rochelle Moulton: that wouldn’t be fair. Yeah,
11:43 – 12:11
Shannon Weinstein: no stuff changes. We don’t have a crystal ball guys. But what we can do is kind of point you in the right direction from a broad standpoint and say, you’re going to have somewhere between 10 and $25, 000. If I told you that you’re like, all right, cool. Like I feel better now just knowing that in my power to say, if I’m going to owe 10 to 20 grand in 9 months from July, now I have the power to say, okay, but that means that if I save up 2 grand a month for the next 9
12:11 – 12:32
Shannon Weinstein: months, I’m covered. And it’s like, that feels really digestible. So then when you break that down and chunk it down into your savings goal is $2, 000 a month until tax season, most solopreneurs who are probably listening to this go, I could do that. Yeah, but if I told you, if I told you like on April 14th that like you owe 20 grand tomorrow, you’d freak out.
12:33 – 12:35
Rochelle Moulton: And I’ve seen that.
12:36 – 12:59
Shannon Weinstein: Yes. Nobody wants that cashflow hit. And I think that a lot of the times we fall into this trap where we’re just focused on the compliance aspect of the tax return and not managing the cashflow at the same time and making sure that we have the savings to pay for it. So I think the best way to minimize tax season stress is to take away its power by predicting what’s going to happen and not waiting for your fate to be read to you like a fourth quarter report card.
13:00 – 13:26
Rochelle Moulton: Yeah. And I think the other thing is I’m thinking about that is, is part of this, depending on your CPA, is making sure that they stay on top of this. As I’ve asked for different things and they forget because they’re in a heavy production environment and Summer is relaxed time. So yeah, it’s still, it’s like we can’t let go of our responsibility to participate in this process, even though we’ve outsourced aspects of it to a professional.
13:26 – 14:00
Shannon Weinstein: Correct. I’m going to use a McDonald’s analogy because you’ll get this, Rochelle. I mean, how many times did the grill, like we got an order for like hamburger, extra pickles. How many times do they forget to do that extra little step? And like, right. Okay. So why? Because they’re churning out like 100 an hour, right? That like noon on a random Saturday. So why is that relevant? Because your tax professional is like the fast food joint. They are transactional. You are going to them because you need 1 thing done and done right, hopefully, but you’re going
14:00 – 14:35
Shannon Weinstein: to them for a specific thing with 1 fee and saying, do my taxes versus hiring a chef or going to a steakhouse where it’s custom and you can customize your options and you can order from a different type of menu. There’s a different experience associated with that, and of course, a different price tag. So you have to align your expectations with what you’re engaging them to do. So if you’re simply paying to have them do your taxes and publish the story, then you have to reset your expectations. They’re not going to help you co-author that story.
14:35 – 14:51
Shannon Weinstein: They’re not going to probably be engaged with you year round. So you want to find someone who offers that kind of end-to-end service and will be able to do that for you, because not all CPAs are created equal, and not all tax professionals offer all that. So you have to be really clear about what it is you want and what your expectations are.
14:51 – 15:09
Rochelle Moulton: Well, and I think the other thing that you alluded to is you have to be willing to pay for this. And there are a lot of people that I talked to and they have this set number in their mind that is very much what that buys you as a production environment, which is fine for a lot of people, but not for everybody. Sometimes you do need the chef.
15:10 – 15:19
Shannon Weinstein: Yeah. Yeah. Business owners especially, I think if you especially if you’re new to it, you want to form a relationship with that person because they’re going to help you with your biggest expense as a business owner.
15:19 – 15:35
Rochelle Moulton: Oh, absolutely. I think the first business I started, I felt like I was joined at the hip with my accountant. And I had employees and we had contractors. It was complex for such a small business, but I felt like she was my most valued partner in running the business.
15:35 – 15:37
Shannon Weinstein: Yep, that’s how it should be.
15:37 – 16:04
Rochelle Moulton: Okay, so we know what we want it to be like, tax time, and we know that we can do something, say, July, in the July timeframe to help make it better. What gets in the way of our doing all of this? Is it that we’re not setting up the right systems? Are we not hiring the right people? Are we just putting our head in the sand? What gets in our way? Like, why don’t we all just have smooth tax times?
16:04 – 16:33
Shannon Weinstein: All of the above. It’s like saying, why didn’t you work out this morning at 5 a.m.? Well, well, and then like, yeah, like I didn’t get good sleep and I have to do this thing and I have to… And like the kids woke up and they have to go… So there’s a million excuses why we don’t do it. And trust me, I get it. I’m a business owner myself. And if I wasn’t doing this for a living where I felt like I had to live up to my own practice what I preach, It’s definitely tempting not
16:33 – 17:02
Shannon Weinstein: to do it. It’s the eat your vegetables part of your business, but it is what’s going to make you healthy. It really comes down to that human psychology of we do what will give us the most immediate satisfaction or what we think will drive the immediate result. And we don’t do the long-term small consistent things that are really gonna make a difference, like the 5 a.m. Workout every day or whatever it may look like, like eating the vegetables. So I just think it’s the kind of this human psyche of, I’ll deal with that later because that’s
17:02 – 17:26
Shannon Weinstein: not a fire I have to put out. Because I think as entrepreneurs, we tend to just be reactive to the environment that’s being thrown at us and dealing with the stuff we just have to do every day. And this doesn’t feel like a have to do for a lot of people. And I think that’s where it comes into play is treating this and giving us the priority of a have to do and making it a deal breaker thing as a habit that will help you grow your business. Because I think it really will. It will help
17:26 – 17:46
Shannon Weinstein: you build that strong foundation and fortify your business, but you will not feel necessarily the effects of it until you don’t enter into a crisis mode, right? But you will feel it if you hit a crisis mode. Unfortunately, people wait until they hit that moment, like I said, when the jeans don’t fit to then go, I should start working out.
17:47 – 18:03
Rochelle Moulton: Yeah. You know, I’m thinking this episode is going to air just after the first of the year. And so I feel like if you’re searching around for some new year’s resolutions relative to your business, that getting your finances under control might be a good 1 if they’re not already there.
18:04 – 18:04
Shannon Weinstein: Definitely.
18:05 – 18:38
Rochelle Moulton: Not big on New Year’s resolutions, but I do like this idea of approaching this as a habit. I know in my own case, I’d always done it as a habit, But I didn’t have the right level of professional help on the bookkeeping end. And once I did that, and I did it because I had a crisis, once I redid the way it was being done, I outsourced it in a different way. I now get monthly statements. I don’t ever worry about it anymore. It takes me a few minutes every month and the difference is like night
18:38 – 18:38
Rochelle Moulton: and
18:38 – 19:05
Shannon Weinstein: day. Totally. Cause you’re compounding like the few minutes every month plus it will take you instead of a few minutes every month, add it up to a few hours for every month when you’re doing it at the same time. So it’s like, it just compounds into this massive project that we also put off and create in our heads as this monster under the bed that has to get done. And I think that we just tend to avoid looking under the bed because we know there’s a monster under there. In reality, it’s a mouse. But until we
19:05 – 19:29
Shannon Weinstein: look at it in our heads, it’s a monster. So we avoid it. But the truth is, it’s really not. Once you really get your head around it and you start addressing it. I’ve had clients come up to me and friends and colleagues, people I’ve coached who just go, Shannon, you did this training for our coaching group. And you told us like, it was 2 years ago, I was in your seminar and you said, you need to go set up your LLC and set up your bank account. And I was like, yeah. And he’s like, I literally
19:29 – 19:53
Shannon Weinstein: just did it last week. I was like, wait, that was 2 years ago. He’s like, yeah, I know. I was putting it off. I was putting it off because it sounded so daunting because I was set up in LLC. I had no idea where that entailed. Shannon, it took me 20 fricking minutes. And I was like, yeah, dude, I know. And he goes, I was avoiding this thing thinking it was going to take me 12 hours and all this paperwork. I was like, no, dude, it takes 20 minutes. She’s like, I would have done this 2
19:53 – 20:15
Shannon Weinstein: years ago. I would have done this right when we hung up the call. I said, yeah, that’s what I’m trying to tell you. It really is a lot easier, but when you make it up into something in your head that it’s going to take forever, especially if you try to do it alone without any professional help or using resources like me, my podcast, you, if you’re trying to do this all by yourself and figure it out, yeah, it’ll take you a little bit longer, but it definitely won’t be as bad as you think.
20:15 – 20:35
Rochelle Moulton: Yeah, yeah. So we talked about kind of the big things that can go wrong, but are there signs that tell us we should be paying more attention to how we manage our finances and our taxes other than, yeah, there’s no money left in the account. Are there more subtle signs that we should be paying attention to?
20:35 – 21:02
Shannon Weinstein: Yeah, I always say you should be. Now, this is a little bit more advanced, but when you have good data and you have good bookkeeping, that’s the foundation, right? So if we’ve established that we need to be collecting the data through our bookkeeping, the next phase of that is using that data that then turn that into decisions. So if you’re looking at hiring a new contractor or you’re looking at their compensation or you’re looking at new expenses, hiring a coach, whatever that looks like for you or entering into a new venture, the question you should be
21:02 – 21:32
Shannon Weinstein: asking yourself is, how much money will this cost me when and what will it bring in in return? So like, is this something that will return me money or was this something that I will be spending and I won’t see a return on for a long period of time? So for example, I’ll give you an example, social media manager, yes and no, depending on like you’re going to invest in them, they’re going to create content for you. That may not be an immediate return on investment, right? That may not be like an immediate, you know, feel
21:32 – 22:01
Shannon Weinstein: like you’re, you’re recouping all of that money right away. It’s going to be an investment in the growth of your social media and therefore your revenue, but you’re going to see that money come back after a long period of time, probably. Now versus hiring someone to do Facebook ads, that’s different. Because the speed of the ROI should be a little bit faster because you’re literally paying for eyeballs on your stuff and giving them a specific call to action. So there’s a bit of a difference there. Now, That’s just 1 example, but you have to be looking
22:01 – 22:31
Shannon Weinstein: at like, what is the, what we call cash conversion in a way. How long does it take money to come back to you when you spend it? Number 1. And number 2 is looking into forecasting. Now, again, we don’t have crystal balls. We’re not Miss Cleo, if you remember that reference, but Zoltan, if you want to go back. But we are not those people that can just predict the future. However, we can notice patterns. And that’s the biggest thing. Noticing patterns, noticing seasonality, noticing what’s going to be coming up and knowing where you’re going to be
22:31 – 22:54
Shannon Weinstein: at. Like, are you taking a vacation for a whole month? Maybe we’re going to bring in less revenue in that month because you’re going to be so busy with your other stuff. So maybe we need to tone it down a little in figuring out, can we operate? Are we going to be at a loss that month and so on? Can we afford that? Maybe we shouldn’t incur a new hire in that month that you’re going to be a little slower. Or we need to build up a reserve for 6 months before we hire this person. Decisions
22:54 – 23:06
Shannon Weinstein: like that, and that’s where I come in as fractional CFO, decisions like that are really key in looking at your cashflow forecasting and in looking at your projections to know, hey, what direction am I heading in so I know if I need to steer the boat?
23:07 – 23:25
Rochelle Moulton: Yeah, yeah. And what strikes me too is, like, how can we best decide what kinds of help we need? I’m speaking financially in particular. How can we decide which things we’re going to do ourselves, which things to automate or outsource and of course to whom is the other question.
23:25 – 23:46
Shannon Weinstein: Yeah. I think it all starts with how savvy you are and how much joy it actually brings you. So people like you and me, maybe we don’t mind taking on the bookkeeping stuff for a period of time because it’s like, it’s not that much trouble and I feel like I got a good grip on it. It’s fine. But then there are some people who are like, I would rather go get a root canal than open up my QuickBooks. And That’s okay too.
23:46 – 23:46
Rochelle Moulton: Yes.
23:46 – 24:13
Shannon Weinstein: But you just got to be self-aware. So if you’re 1 of those people, I’m going to be honest and tell you, if you’re 1 of those people who would rather get a root canal than open your QuickBooks, guess what? You better have money to invest since you don’t have your time to invest. So you’re going to be investing money or time or both, but never neither. So you’re going to, you’re going to have to invest in your own education or you’re going to have to invest in a professional who has that education to help you. And
24:13 – 24:40
Shannon Weinstein: in terms of who that professional would be, if you want to pay someone to help you, it’s going to vary. But I think you start with a bookkeeper, you layer on someone who can publish the story for your taxes. And I would say if you’re making a couple hundred grand, you want to start looking at tax strategies. You want to start having that person be more of a trusted advisor to you as opposed to your, as I call it, April 15th 1 night stand. You want to have a relationship. This better not be like a you
24:40 – 25:07
Shannon Weinstein: up text person in April. This is somebody who you hang out with and like Go to the lake with in the summer. You know what I mean? Like that relationship. Not the 1 you call in April with a you up text. That is, and that’s what I don’t want to be. I actually put that on my website. Like I’m not your April 15th 1 night stand. Like I want to be wifey material all summer, hang with you, like all that. And you want that person when you hit a few hundred grand because you want to have
25:07 – 25:33
Shannon Weinstein: that person on your side that you can call, know that they’re going to answer you and that they know your business and they know your data and they have access to it and they can help you. Like you said, when you start your business and you have employees and contractors, that’s complicated. When you have sales tax issues because you’re selling a product, that gets complicated. So when you have these other elements, you really should be working with someone in some capacity, but the needs will vary based on where you’re at in terms of your years in
25:33 – 25:35
Shannon Weinstein: business and what you do.
25:35 – 26:05
Rochelle Moulton: Yeah, I’ve said this to a few people that have kind of gotten into this position is there can be a feel of a production environment. Like where they’re just, because doing taxes is a numbers game. You’ve got to do a lot of them to make money at it typically. But when you get to that point where you don’t want to be in that environment, you want what you just described. You want basically a fractional CFO to come and help you think through strategically what you want to do and when you want to do it. And having
26:05 – 26:15
Rochelle Moulton: seen that with my clients, it’s like night and day once that happens. So I guess the message is don’t be afraid, right, to spend some money when you’re ready.
26:15 – 26:16
Shannon Weinstein: Yeah, yeah, definitely.
26:17 – 26:30
Rochelle Moulton: But once we have those people in place, how do we know that we’re getting good advice? Is it as simple as trusting our gut or should we be getting an occasional second opinion? I mean, what are your thoughts about that?
26:31 – 27:04
Shannon Weinstein: It’s like a relationship. Like I said, it’s like dating where, how do I know it’s working? I feel like you kind of know, like your intuition is insanely powerful. Number 1 is if you feel like you’re uncomfortable or you’re insecure, like for example, if you email this person and you’re like, good luck if I ever hear back. If you’re feeling that or you get an email from them and you go, that’s something. Acknowledge that because that’s like a visceral instinct. So That’s something with your intuition that maybe you don’t enjoy talking to this person or whatever.
27:05 – 27:34
Shannon Weinstein: I would say intuition is big, but I think that in terms of how you grade, how well they’re doing in a sense, it really comes down to, are you meeting your goals? Are they listening to you? Are they giving you cookie cutter advice they could give any Joe Schmo? Are they forgetting little things like your husband or your wife’s name? Like they forget about you, forget what your business is called. Are they showing signs that there’s a lot of you in their client roster? Right? I think that accountants, when they have a few hundred clients, it’s
27:34 – 27:43
Shannon Weinstein: hard to keep track of people. Like we’re only human. Like that’s also why I have a dozen clients. Cause I said, I never want to forget 1 of your dog’s names. Like I want to
27:43 – 27:49
Rochelle Moulton: know how somebody can do a few hundred. I would never be able to keep the name straight. I totally get why that would happen.
27:49 – 27:54
Shannon Weinstein: Rachelle, the average accountant has 1100 tax returns per person at the firm.
27:55 – 27:56
Rochelle Moulton: That just boggles the mind.
27:56 – 28:22
Shannon Weinstein: It doesn’t it? But that’s the thing, though, like I go back to my McDonald’s, like how many hamburgers did we churn out versus how many does a bistro steakhouse where a burger is $30. Think about how many get churned out and how much care goes into each 1. So I’m not saying that accountants, the tax pros don’t put care into your tax return. They do, but understand that you are 1 of 100 that is getting done and you are in a line with a bunch of other people doing the same thing. It’s much less than like
28:22 – 28:50
Shannon Weinstein: a custom catering service would give you. So you just have to set your expectations properly that you are 1 of a thousand or 1 of several hundred. They will get to you, right? But if you’re in that production environment where you feel like, I really just want someone to sit down with me, explain this to me in a language I understand, and to make this a bit of an easier experience. There are plenty of modern-minded CPAs out there, especially those who started their own practices that offer a similar service to me and focus heavily on taxes
28:51 – 29:09
Shannon Weinstein: that can help with that because that’s what it’s really coming down to, especially with AI, which by the way is a whole nother thing. But that is going to be a big driver for accountants to learn how to communicate well and to explain the story because eventually we’ll be able to do our taxes pretty much ourselves using different computing methods in the IRS website.
29:10 – 29:17
Rochelle Moulton: I just have to go on record as saying I don’t ever want to do my taxes myself. I would rather put needles in my eyes just saying.
29:17 – 29:42
Shannon Weinstein: Well, good. Every accountant is thankful for people like you to keep us in business, but there are plenty of people who will take the opportunity to… There are some people who say, I’d rather do my own taxes than ever talk to a CPA because they just don’t… To your point earlier, like you mentioned that I want to bust the myth that CPAs aren’t fun. A lot of them aren’t. A lot of them aren’t. A lot of them are not fun to talk to. So like, I understand if you guys don’t want to meet with us, it’s
29:42 – 29:47
Shannon Weinstein: totally cool. But there are some out there that you will vibe with and that will meet your needs.
29:48 – 30:05
Rochelle Moulton: Oh, absolutely. And I think CPAs as an industry have done such a better job at distinguishing themselves, the individuals, you know, somebody who works just with creative professionals, for example. So they’re out there. I just encourage you to find the right fit for you.
30:05 – 30:05
Shannon Weinstein: Yeah.
30:06 – 30:24
Rochelle Moulton: So we’re getting close to time, Shannon. I have 2 thoughts. 1 is, before we hit record, you were talking about an interview guide, And I just love this idea. I wanted you to talk about it a little bit and we’ll put the URL into the show notes so people can access it if they’d like.
30:24 – 30:51
Shannon Weinstein: Absolutely. So you just mentioned, you know, hiring the right person that fits your needs and this fits in perfectly with that. So I noticed that there was a serious need in the industry and in our spaces, entrepreneurs to matchmake the right accountant with the right entrepreneur. I feel like a lot of the times you guys hate school subjects because of the teachers that you had, right? And that’s a big factor is who is communicating with you. And that is going to set the tone for how you embrace these concepts. So I’m a firm believer in matching
30:51 – 31:23
Shannon Weinstein: the right professional with the right person so that you guys can drive results together for your business. So I created this tool called the MoneyPro Matchmaker. You can pick it up at moneypromatchmaker.com. Really easy. Moneypromatchmaker.com. And it’s got tools on what we call ourselves. So it’s, do I need a bookkeeper, a tax pro, a tax strategist, a fractional CFO? What the heck each of us does, what problems we solve, and most importantly, what questions we answer for you. So if you’re struggling with these types of questions, chances are this type of person can answer those questions
31:23 – 31:52
Shannon Weinstein: for you. Because a lot of you guys will go on Facebook and say, I need a good CPA. Here’s the problem. CPA is like saying doctor. If we don’t know what’s wrong, we can’t solve the problem for you. But if you say, I need a dermatologist, bam, we know exactly what specialist to find. We know somebody front of mind. But if you say, I need a good CPA, there’s a bajillion varieties of CPAs out there. There are some that have never touched a tax return in their lives. So in reality, the most effective way to ask
31:52 – 32:03
Shannon Weinstein: for what you need is to know exactly what service you need and this helps you with that. Plus it gives you a guide on how to interview each of these people so that you’re getting the most out of the relationship and setting proper expectations.
32:04 – 32:19
Rochelle Moulton: Love that. I think that will be a hugely useful tool to this community. So thank you for that, Shannon. Of course. So if you could go back to who you were when you first started your business, Like what’s the 1 thing you’d advise her to do?
32:20 – 32:40
Shannon Weinstein: Oh man. Oh, so many things. I would say really respect your time boundaries and keep the promises to yourself because I always had a tendency and still do to say I’m going to do something but the only person accountable to me is me that I said that
32:40 – 32:40
Rochelle Moulton: because I
32:40 – 32:57
Shannon Weinstein: thought it to myself like, oh, I’m going to wake up at 5 and work out or I’m going to get this thing done today. And I just wish I kept more of those promises to myself. I would feel like I had more trust in when I thought I was going to do something working on that. But that would be a big focus of mine to build my own self-trust.
32:58 – 33:09
Rochelle Moulton: Brilliant. Thank you for that. So Shannon, we’ll be putting up all sorts of links to you and your content in the show notes, but where’s the best place for people to learn more about you or catch your podcast?
33:10 – 33:31
Shannon Weinstein: In the same app you’re probably in, head over to, to Keep What You Earn. Keep What You Earn is where everything is. We’re at keepwhatyouearn.com, keepwhatyouearncfo.com to explore our services. We’re everywhere. So check out every podcast platform. We would love to have you as a listener as well to add this to your rotation. So just look for Keep What You Earn wherever you listen.
33:31 – 33:38
Rochelle Moulton: And it’s instructional, it’s fun, it’s interesting, and it has personality. So well done on that podcast Shannon.
33:39 – 33:40
Shannon Weinstein: Thank you so much.
33:40 – 33:51
Rochelle Moulton: Well, so thank you so much for being generous and sharing your expertise and your wisdom and some of your experiences with us. I really appreciate it.
33:51 – 33:53
Shannon Weinstein: Thank you so much for having me on. I’ve had a great time with you.
33:54 – 33:59
Rochelle Moulton: Awesome. So that’s it for this episode. I hope you’ll join us next time for Soloism.
