Taking the Leap Into Full-Time Entrepreneurship

Sasha: 0:00

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Dorothy: 5:01

Yes, I don't know how I would existed this long without wine. My twins are turning 21. They're my oldest next week, and now they can pick up wine on the way home.

Sasha: 5:18

Like, it might be worth it in the end that they can. I'm at the very beginning so that my son is five. So we're starting and he's an everything like we do the T ball. He does gymnastics, he has done soccer. So we do. I mean, the beginning stages of that, though.

Dorothy: 5:39

Yeah. It's amazing how, at the end stages, I only have one left in high school. And I'm starting to miss it already. Oh, you never think you will. You're like God, if I could just have a Saturday morning to myself. And then you're like, man, it's like, I wish I could go to a lacrosse game.

Sasha: 5:57

Yeah, I don't know if he doesn't do the lacrosse. But I don't know if I missed the Saturday morning soccer games. I'll say that much. So tell us a little bit kind of about your journey and why you left the corporate world? And yeah, just tell us a little bit about yourself.

Dorothy: 6:16

Yeah, so yeah, you set it all, you know, all the places that I've worked this whole time. I will openly admit, I never wanted to be an entrepreneur. That was not in my, this is what I'm going I come from a long line of people who did it, now I'm motivated to do that myself. I was laid off as the CFO of a company. And as you mentioned, I have four sons. And at that point in time, I had been working for remotely actually since 2013. But the last, and as a CFO for a company. But the last job that I had out of my house, I was commuting to DC, you know, an hour plus hour and half.

Sasha: 6:59

I know that commute very well.

Dorothy: 7:00

There you go. It's never fun, there's never a good day. And I realized I could not be gone from like seven o'clock in the morning until 7- 730 At night, every day with four sons, especially they were going into their teen years. And I feel like that's an even worse time to be away than when your kid is small, small. Because you know, there's only so much you know, okay, don't put that in your mouth kind of stuff, right. But when you get older that it takes on a completely different context. So I realized that, oh, shoot, I am going to have to figure something out. And to be honest with you, I'm a fractional CFO, which means I come in as the chief financial officer to companies, and I help advise them in on strategy and how to, you know, utilize their money for the best purposes and how to scale and grow and sustain. But my first two clients were bookkeeping, because that's what I could get. I mean, it was like, okay, yeah, I'll pay your bills, and I'll send out your invoices. And it was, honestly for me. I mean, there's nothing wrong with bookkeeping. But when you have, I've never had never done it before. I was an accountant. But I'd never done that before. And it was just I think, as a parent, we tend to just do whatever has to be done. So mine is a journey more of hindsight, like, oh, what could I have done better back in the day? And I think, you know, some of the things that, that really, you have to really think about is one, you know, do I have the space in my house? Do I have an office, whatever, away from children and pets and all that kind of thing. I can't tell you how many times your space I was sitting in on a board meeting with a client, their whole board, and my son came in in a towel to ask me if I had done the laundry yet. It was a video meeting. It was a zoom call. And I'm like ughh. So I ended up putting like an "on air light" outside my office door so that they saw it there was like don't come in. But it took like, it was scary. I'm not gonna lie. It was really scary. It wasn't like I could go from the side hustle to the, which I think is also like, really scary. Because it's like, when do you make that jump? When is it enough? When, and there's always going to be that element of like, okay, I'm just going to do it. But I think you know, like, you know, just not knowing. We were talking about this earlier, not knowing what you don't know, I think makes you slightly

Sasha: 9:33

Yeah, it makes it a little easier, because you're like, I'm just gonna do this and we'll see what happens.

Dorothy: 9:39

And it's like, you know, I had four kids, my first two were twins. And so when I had the third and it was just one I didn't like I didn't know any better going into getting pregnant that twins was going to be that much different than having one. You just don't know. So kind of the same, the same concept, but I think the things that you really have to think about are you know, can I do I have enough support? Whether that's financial or, you know, support with your kids getting them to and from things, you know, structure in your house? Like, do I have an office to sit? And do I have whatever? Like thinking about that stuff? Do I have that that behind me? You know, in order, like, what if I falter just slightly? Do I? Do I have a safety net a little bit? And I think, you know, going into it just thinking about is my, you know, is what I do, really a viable thing on its own? That's the other thing, right? We all come from these corporate environments, and we have our own little silo that we sit in and our own little thing that we do, and we're supported from all these other areas. And it's like, oh, wait to see what I just do by myself. Is that enough? Or do I have to be part of a team? You know.

Sasha: 10:55

I do want to ask, though, so even though you were laid off, what made you decide to kind of jump into I'm just gonna do a business instead of going to get another job?

Dorothy: 11:07

I didn't want to I couldn't, I didn't want to, I didn't want to be away from the house for that long every single day.

Sasha: 11:13

Yeah, I understand that completely. When I will say the I don't mean this in a facetious way, because I know COVID. Of course, it's so many bad things to a lot of people. But the biggest blessing that it gave me was time with my son, like it gave me the ability to be home. And I was just like you, I would wake up at five o'clock in the morning, I'm out the house by

six. I'm picking him up by 5: 11:35

30. And he was not even two at the time. So he's going to bed at like seven. So I have at most an hour with him during the day and, and he doesn't even remember now like when Mommy used to go to work. And now he's just like, Oh, mommy just goes to her office. And she does work there. So he doesn't remember me not being home. But I just remember, like, I barely see my son, I don't see my son at all.

Dorothy: 12:01

Yes, and you get him for the worst parts of the day.

Sasha: 12:03

Oh the worst, I tell my husband.

Dorothy: 12:06

And then you get him at nighttime when they're trying to go to bed and you're like, I'm the bad guy.

Sasha: 12:12

My husband and I had so many conversations about that, because he's a police officer, but he would work in the evening. So he would have my son in the mornings until he dropped them off. And I was always like, you get the happy kid. You get the kid in the morning who's just like, they just woke up. They're in a good mood. I was like, I come home and I'm dead tired because I've been at work all day. And then on top of that, I get like the cranky, like, I just ready to go to sleep. But I'm fighting sleep kid. And I was like it's not, I don't even get the fun kid.

Dorothy: 12:46

It's so true. It is so true. Oh my goodness. I don't miss those days. Now, like the other end of it, where they're out, you know till way late, you know, like the flip side of it. Where are you, just come home? Yeah. So it was it was more a matter of like, necessity is the mother of invention, right? So it was I have to find something, I'm just going to do this. And I answered a couple of like ads in Upwork. And yeah, and it was like, Okay, I'm doing this now. And I'll be honest, like, I'll be honest, I sat... like my kids at that point, so this was five years ago. So they're between 16 and 21. So they were between 11 and 16 at the time. And I sat them down and said look, our finances are like shrunk, like big time. And I showed them flat out here's what I have coming in every month. It's the things we have to pay, you know, at that time I was renting. So it was the rent, utilities, car payment, whatever. And they now get it and now they're good at their own finances. Like they're like, Oh, I only have this much coming in, I can't go do that I have to save for it. You know.

Sasha: 14:03

Saving who knew that was a thing. I want to ask you though, because I know that while you went through this journey, you know, you're a single parent, I have help, I have my husband. So you know that and I have a full time job, which makes it a lot easier to have a business but I also know a lot of entrepreneurs who have a partner, which makes it easier for them to have their own business and to step out into that business because you know, there's somebody else that can pay the bills, there's somebody else that can support them and things like that. So from a single parenthood perspective, what did you need to have or what do you think people need to have if they're making that that journey from having a quote unquote secure job into the unknowns of entrepreneurship It doesn't suck. It's great and it sucks at the same time. You because... know, it's great because you have flex ability and the ability to walk away from something that is not serving you. But you also have the ability to walk away from something, and they have the ability to walk away from you. So it's a little like ugh, but I think, you know, I, everybody says this, and I did not do this. So they're like that, having, you know, the three to six months, you know, expenses in the bank, so that I did not, I had was freshly out of a divorce, I had no money in the bank, I had given my last like, deposit money, like free money to for a deposit on my house that I was renting. And that was super freaking scary. So as much as you can have. I sit down with women all the time, women, I work with women entrepreneurs, and I sit down with even women who are pre entrepreneurial. And say, go through the list of what are the things that you're responsible for finance wise, and that will become the salary that you need to get out of your business. Your business, if you have $1,000 worth of expenses every month that your business needs to be making $1,000, at least for to work for you to step away from whatever else you're doing. So it's that mind shift of what is my salary, your salary numbers now becomes the personal expenses that you're trying to cover. Yeah, I think that's what's scary to people is that it's kind of, you know, they look at that number, whatever that number may be, and especially if you're doing it by yourself, like I have to be able to consistently have that money coming in. And so having that cushion of that safety net, at least makes it less scary. I guess.

Dorothy: 16:43

It does. You know, the other the, the other side of it, too, is when you have, you know, consistent you're talking about consistent, right. So when you have months that you get in a lot more. Say it's saying no, I'm not gonna go out and buy all this stuff that I feel like I deserve right now. Or I've put up it's taking the vast majority of that and putting it aside. And you II keep, and this is kind of like there's there's a book called Profit First that goes into like, I only keep three bank accounts, because I can't do the five and the dripping from one to the other.

Sasha: 17:14

And I have one, I didn't read the book, I listened to a podcast about the book. And I was just like, that seems like a lot to manage.

Dorothy: 17:23

I have my modified version, where I have like what operating account, I have a savings account for just savings, and then I have a tax account for putting stuff and every month I like siphoned off into both of those. So that if, and for example, I just disengaged with two clients this month,

Sasha: 17:43

That's a nice way to put it.

Dorothy: 17:46

And I have money set aside for okay, I'm okay for, you know, three or four months until I can backfill those, you know, those pieces in my business. But if I had spent that like at Christmas, like, Whoo, yeah, right now, I would be panicking in a big way. So I think it's being you'll also have to be really, really strict with yourself on what am I going to do with the money when it comes in the door? I'm not going to spend it all I'm going to put it aside. And the thing people also have, you know, always forget about our taxes.

Sasha: 18:15

I was just about to say that I was going to say I'm so glad that you mentioned that tax account, because that's the one that everyone forgets about. Because when you have I mean, it's not even in our thought when you get a paycheck that you're not seeing your whole money, like taxes. I have looked at what my my gross is, and it makes me very upset at what my net is because it's like, oh, so much money that just goes away. But people forget that, when it's just you that money is still, you still have to pay that money.

Dorothy: 18:49

Yes. And it's scary. And we're I think so many of us are also really tempted to and I think I'd be lying if I didn't say a lot of us do this, where at the beginning, you put a lot of your personal expenses through, you know, okay, yeah, this is office supplies, I'm buying my kid books for school. But you know, you don't want to continue that. And you don't want to do that in a in a manner where the IRS starts going that's interesting. So, you know, it's kind of a balance of what are necessary, you know, ordinary expenses that and when I say necessary and ordinary, I mean, when I'm looking at your business, does this make sense that something like this would go through, right. Those are fine. And then putting the money aside, just you know, even if it's like 5% a month, 10% a month, whatever, just putting it aside so that you have it so that when a tax time comes estimated payments or year end or whatever you're like, holding on, because I've been there to where you're like, oh, and then you look at I've got this covered. How smart of me.

Sasha: 19:56

Yeah, I've been in situation. I just last year switched and I since you an accountant you'll understand this way more than I did. Because I still don't understand it. My tax guy looked at my business stuff. I've been a sole proprietor for a long time. And he was like, we probably need to make you an S corp, because what's happening with your money isn't making sense for you tax wise. And so it makes sense for you to become an S corp. And I was like, Okay, I don't know what that means. To this day, I still don't really understand it. I get some of it. But I know it'll help me on the tax end. And so I think it's kind of like, I think that's also something people don't think about when they are transitioning into entrepreneurship full-time. It's like, talk to someone like talk to people who are like accountants and lawyers who can set you up in a way, set your business up in a way that makes the most sense financially, legally, that's going to help you come tax time come those times when you're like, I don't know what's going on.

Dorothy: 20:53

Yeah, no, absolutely. I think that one of the biggest things, so many people just put that stuff aside, I've seen you know, threads on Reddit, where it's like, why do you need an EIN you're fine, just do it on your own. You don't need anything else until you make X dollars a year? And I'm like, no, no, you don't want to backtrack. You want to start off on solid footing. And yeah, finding out what entity type you should be, you know, even if it's you spend $150 talking to a lawyer for half an hour to go what do I do? Do it legally?

Sasha: 21:22

And sometimes they have free consultations too.

Dorothy: 21:25

Exactly. I mean, that yeah, that's, that's, you know, on the on the higher end, and then, you know, you don't need a bookkeeper. But try to use something like QuickBooks or something not in an Excel doc. And just educate yourself. There are so many just communities you can join and free courses and paid courses and things like that, the more education you have around it, the more confident you're going to be in putting yourself out there as a business and knowing I'm good to go.

Sasha: 21:55

Yeah, I definitely advocate towards the very least talking lawyer and a tax professional. And not especially like, not going on Facebook and asking these kinds of questions. I saw a post in a Facebook group. Yesterday, I think it was about you know, of course, end of January, it always comes to 99 time, when do I need a 1099? Who I need it from? How do I spend the 1099? And someone was asking or someone said, like, Oh, if it's under $600, you don't have to report it. Everyone's like, no, that's not what that means.

Dorothy: 22:28

You dust don't get the 1090. That doesn't mean you don't report it,

Sasha: 22:33

Like all income is like you're supposed to report all of it. So at the very least I talked to someone who has letters behind their name.

Dorothy: 22:46

Yeah, you know, you can, there are a lot of really...those letters like, you know, CPA, of course, it's they can, you know, they can be scary, like, I'm a CPA, I don't do taxes, though. But I have my CPA license, but I send my stuff out, I'm not going to do it myself. It's just too complicate it, but you can find and this is the other super important thing as you're setting yourself up find people to work with, that you can you can talk to, you should never be intimidated. Your lawyer or your tax accountant or something that you feel like, oh, I don't want to ask this question. Or, Oh, they're gonna think I'm stupid. You want a good relationship with them? Because you need to be had that information flowing.

Sasha: 23:26

I completely agree. Like I think it can be intimidating. Because you're walking into situations where you don't know like, sometimes you don't know the question that you should be asking or the information that you need. But these people are here to help you right? They're meant to guide you and set you up in the best way possible. So if you ever talk to someone, you don't feel comfortable asking the questions or, you know, you feel like they're not giving you the responses that you need, then find someone else that you will work better with.

Dorothy: 23:57

Absolutely. And if you have other friends that are in the similar thing, and they have asked them who they use, yeah.

Sasha: 24:03

You know, like recommendations, word of mouth is, is a way a lot of people grow their businesses, but it's there for a reason. It's you know, these people trust who they are working with and and who they think could help you. Well, thank you so much for sharing your journey with us. I think you gave people a lot of things to think about when it comes to kind of stepping out on their own. So where can people find out more about you and your business? And if they're looking for like that financial help, because I know that's what you do?

Unknown: 24:30

Yeah, I have a website. You could put it in the notes, I guess. It's dkeast.com. And I actually have a digital course coming out on this very subject of knowing and understanding your financials. So that's coming in March, and that's also on my website. So if anybody's interested in checking out what that might be all about. I'm on Instagram @dkeastassoc and on LinkedIn all the time, you know all the places.

Sasha: 24:57

I will make sure I put all of that in the shownotes so you guys can check out Dorothy, and what she does. But Dorothy, thank you so much for being on the show today.

Dorothy: 25:05

Yes, thank you so much. It's great.

Sasha: 25:09

Happening next week on the Strategy for Creatives Podcast - I'm talking to Kim Dang, founder of Group Convert and creator of the G.O.L.D. rule of group sales method about how to use a Facebook group to grow your business. So don't forget to tune in next Tuesday to listen to the episode. Thanks for tuning in to the latest episode of the Strategy for Creatives Podcast. I hope you enjoyed the insightful discussion and hopefully found valuable tips that you can put in your business today. If you found the podcast helpful, I'd love it if you take a moment to rate and review the show on your favorite podcast platform. Your feedback helps me make a better show and reach more listeners like you. And don't forget to share the podcast with your favorite business owner who could benefit from the strategies and insights I share on the show. New episodes come out every Tuesday so make sure to subscribe and stay up to date with the latest trends and techniques for growing your creative business. If you want more don't forget to join the Strategy for Creatives Facebook group, or you can follow me on Instagram @strategybysasha. Have a topic suggestion or a question you want to hear answered? Email me at hello@strategybysasha.com Thanks for listening, and I'll see you next week with another episode of the Strategy for

Creatives: 26:20

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