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...