A lover of all things technology, Nayo lives by the motto “Dance like no one is watching”. This EA, MBA, mother, wife, and proud dog owner is a resident of Baltimore, Md. – a city she’s lived in for more than half her life. Nayo joined Blake and David for an interview recorded at the second annual Accounting Salon conference in in New Orleans in May 2019. Learn about what motivated Nayo to start her own tax practice, the challenges of tax resolution, the opportunities of cloud-based tax and bookkeeping, and more.
Connect with Nayo Carter-Gray
Get in Touch
Thanks for listening! Follow and tweet @BlakeTOliver and @DavidLeary. Find us on Facebook and, if you like what you hear, do us a favor and write a review on iTunes. Interested in sponsoring the Cloud Accounting Podcast? For details, read the prospectus.
Blake Oliver: Welcome to the Cloud Accounting Podcast. I'm Blake Oliver.
David Leary: I'm David Leary.
Nayo Carter-Gray: And I am Nayo Carter-Gray.
Blake Oliver: It's So, great to finally meet you and talk to you in person here at the Accounting Salon in New Orleans.
Nayo Carter-Gray: Woo-hoo!
Blake Oliver: I didn't say that right. How do I say ... Nawlins?
Nayo Carter-Gray: You're not supposed to say Nawlins. N'orleans. N'orleans, baby. That's how the locals will say it to you.
Blake Oliver: I will say it like somebody from Los Angeles.
Nayo Carter-Gray: New [00:00:30] Orleans!
Blake Oliver: We go way back.
Nayo Carter-Gray: We do!
Blake Oliver: First QuickBooks Connect I think we met, possibly.
Nayo Carter-Gray: Actually, it was the second one. I missed the one with Oprah. Wasn't Oprah ...
Blake Oliver: Oprah was the second one, I think.
Nayo Carter-Gray: Oh, So, then it was the third one.
Blake Oliver: Third! Man, that is great [cross talk]
Nayo Carter-Gray: I know. I found out about QuickBooks Connect, Oprah being there, the week before it happened, and because I'm in Baltimore, Maryland, the cross-country trip was just a little unaffordable.
David Leary: As long as you didn't find out too late, because it's not easy to get hotel rooms in the Bay Area.
Nayo Carter-Gray: Yeah, that is true, too.
David Leary: Big [00:01:00] huge conference. Now you're coming to a much smaller conference at Accounting Salon.
Nayo Carter-Gray: Yes. I like events like this, because they're smaller and you kind of get to know people a little better. Then you learn more about what's working in everybody else's practice. You kind of get to hear everybody's flubs, and mistakes, and learn from their mistakes, so that you don't have to repeat them yourself. Especially when you're newish in business.
Blake Oliver: Well, let's [00:01:30] talk about that. Tell us about yourself and your business.
Nayo Carter-Gray: I have been full time in my accounting practice since 2009. My business started because I got laid off from the recession, even though I had been doing taxes for over 26 years now. I'll tell you that story. I started, my first summer job I realized that I could get my tax money back, so I charged all my friends that I knew with jobs $25 to do their tax returns. [00:02:00] That's how my tax practice started. After I got laid off in 2018- 2008, I'm sorry, I decided to venture out and try to do this full time, because I am not a morning person. Somebody telling me I have to be somewhere at 8:00, and it's not my decision, just upsets me very much. I love the flexibility and freedom that owning your own business has.
David Leary: You took that jump really [00:02:30] at the bottom of the economy.
Nayo Carter-Gray: Yes. Yeah, it was- luckily for me, I had a supportive partner. My husband now, who was then my boyfriend, was like, "All right. So, what are you gonna do? Are you gonna go back to work? Or are you gonna try to do this full-time entrepreneur thing?" Because I had already been doing it part-time, I had a small client base. I just told them, "Hey, I'm starting full-time. Anybody you know, send them my way." Luckily for me, my tax practice kind of doubled in the first year, so I [00:03:00] was able to afford to get an office space, and have some money in the bank, and not feel like a broke college student all over again.
Then I got a bookkeeping client who wound up having three businesses. It was like starting just out the gate running with three clients, with one client. I was very, very fortunate, and lucky. Technology [00:03:30] has always been my thing, so early on, I decided to start going to some conferences and learning about cloud-based apps and technology that would make the process easier, because, you know, if you streamline processes, if you use things that work and make your life easy, it makes the business better. Because I also don't want to be one of those people who just work-work-work-work-work-work-work and never have time for anything else either.
Blake Oliver: Are you just doing tax, or are you [00:04:00] doing other services? Are you doing accounting services, bookkeeping services?
Nayo Carter-Gray: Taxes, bookkeeping. I do payroll only for my bookkeeping clients. Tax planning. I'm an enrolled agent, so I also do IRS collections and audits.
Blake Oliver: IRS audits. Fun!
Nayo Carter-Gray: They can be very interesting. Right now, I'm doing more collections work than audits, but to ...
Blake Oliver: What is that?
Nayo Carter-Gray: The difference is, say you get a letter from the IRS that [00:04:30] says you haven't filed in three years. We get you all caught up, and then I help you try to figure out how can you pay this huge tax bill. Because usually people who haven't filed in that long know that they owe, and they know that they owe a lot. We come up with some different strategies to minimize how much they pay. Maybe do an offer in compromise, because usually it's not only the federal liability, you also have a state liability, and states are very hard to navigate, too.
Blake Oliver: What sort of clients do you have?
Nayo Carter-Gray: I [00:05:00] like primarily working with small business owners, those that are in the start-up phase. They've been in business zero to three years, and I like taking them to the point where they're like, "All right, we need to hire someone full-time." I've had a couple of people graduate from me, and I'm totally fine with that, because I don't want to turn into anybody else's employee right now.
David Leary: When you have a client that's graduating, do you always offload them to another person, another [00:05:30] accountant or bookkeeper friend of yours, or do you just kind of cut their wings and let them go on their own? What's that process like for you?
Nayo Carter-Gray: When I notice that they're putting a strain on my time and resources, I recommend that they probably need to hire someone internally, because it's usually they not only need the accounting/bookkeeping help, they also want help administratively. I'm like, "Yeah, I'm not your secretary, so we're not gonna do that, but, if you hire [00:06:00] someone that has certain skills that can help you not only continue the accounting process piece, but they can help you on the administrative side to automate some of the things that you're expecting me to do ..."
Blake Oliver: That was always one of the challenges I had, when I was freelancing in particular, is I was doing bookkeeping, and people would expect me to answer their mail for them ... That's what they think of.
Nayo Carter-Gray: They think ... They figure they're paying you, and [00:06:30] they're paying you to do any and everything they ask to do.
Blake Oliver: Exactly. Yeah.
Nayo Carter-Gray: This is where engagement letters come into play, because you say, "That is not in your engagement letter. I am not your secretary. Your services are blah-blah-blah-blah-blah, because this is what you're paying for. If you want to add some services on, we can do that." I do have some colleagues who include a support package, where they can pay an additional fee to get that mail answered, get the telephones answered, send out invoices, [00:07:00] and do collections. I personally just don't have the time for that right now.
David Leary: There's a lot of services out there, like Ruby Receptionists and services like that … but I've never heard of a bookkeeping firm or an accounting firm ever partnering with a service like that.
Blake Oliver: Right.
David Leary: So, that way you have a place ... "Hey, I have this other relationship with this other company, and we can get your email checked for you and your calendar appointments booked."
Nayo Carter-Gray: It's funny you mention that, because I personally was looking for an answering service for my business, and it is very hard to find one that is affordable [00:07:30] and that can answer the phones and understand the types of calls you get from an accounting perspective.
David Leary: Well, we'll just make something like that this week.
Blake Oliver: No, actually a very good application of Google Assistant.
Nayo Carter-Gray: It would be. Very much so. It really would be. Now, I found a company, and they take all my calls, but even they screw some of those up, too. Like, what in the world? It's because some things just, to me, seem like it would be common sense. Like [00:08:00] if someone calls and says, "I want an appointment," you kind of direct them to how to schedule the appointment online. Or if they say they want an appointment, you get the name and the telephone number, so someone can call them back, if they don't have access to a computer. It's very difficult when you get a lead and then have no information to call the person back. No name ... It's like-
David Leary: It's like having your kids do it.
Nayo Carter-Gray: Yes, exactly.
David Leary: They don't write any of the information down for the phone call.
Nayo Carter-Gray: Right, and [00:08:30] if that's the case, I might as well hire my kids.
Blake Oliver: David is really putting them to work on our podcast, right?
David Leary: I've done some- I've had the kids do some work, but they always want more money.
Nayo Carter-Gray: Well, you know, I'm a big fan of hiring children because it's a tax benefit, especially if you have a sole proprietorship and they're under the age of 17. You could throw some money in a retirement account and write [00:09:00] it all off on your taxes. You can set them up for [cross talk]
Blake Oliver: We need to do this-
Nayo Carter-Gray: Yeah, I have a whole blog post about it.
David Leary: There should be a whole podcast about exploiting your children to do work.
Nayo Carter-Gray: Yes.
Blake Oliver: My son is 4 years old. When can I start hiring him?
Nayo Carter-Gray: As long as you have a job description for him, you can start hiring him right away. The key is to make sure you have the formal job description and you pay him regularly. So, if you have him putting stamps on envelopes, and he gets paid once a month to [00:09:30] do so, then cool.
Blake Oliver: Okay.
Nayo Carter-Gray: But you can put up to the standard deduction, and payment in cash, and then into a retirement account, and get a nice tax benefit.
Blake Oliver: So, these are obviously the sorts of insights that you were delivering to your clients.
Nayo Carter-Gray: Yes.
Blake Oliver: Maybe not as aggressive as what David and I are planning, I bet. I'm curious to know, where do you see tax headed over the next five to 10 years? Because [00:10:00] you've already- you have a cloud-based practice, right?
Nayo Carter-Gray: Yes.
Blake Oliver: You're not shuffling paper around.
Nayo Carter-Gray: No, I'm paperless. When I started my business, that was key from the jump. I wanted to be paperless. And it was funny because I started with Shoeboxed. I don't know, and most people [cross talk]
Blake Oliver: -they were like one of the original.
Nayo Carter-Gray: They were original.
David Leary: -one of the first three apps I bought on apps.com originally.
Nayo Carter-Gray: Yeah.
Blake Oliver: They were acquired by Earth Class [00:10:30] Mail. I don't know if you ever used them.
Nayo Carter-Gray: No.
Blake Oliver: Check out Earth Class Mail. They receive and [cross talk] everything out for you-
Blake Oliver: Scan everything. They do a good job of that. It's just their integration sucks now. They haven't kept up with that side of the room.
Blake Oliver: Oh, with Shoeboxed?
Nayo Carter-Gray: Yeah, but we still use them. If I have people who want to give me a whole box, I'm like, "No, I'm not taking that." I have people that are like, "I'll scan it in." You're not gonna scan it in. Just mail it to Shoeboxed, let [00:11:00] them do all the job, and I can work my magic from there."
Blake Oliver: Saved my life.
Nayo Carter-Gray: Yeah, but where I see accounting and tax, I don't really see it going away. A lot of people are afraid that it's, you know, turning into the bots are gonna take over.
Blake Oliver: Yeah.
Nayo Carter-Gray: They will, but they're gonna mess it up, so accountants are gonna be needed on the back end, especially with IRS audits and stuff, because the IRS uses artificial intelligence to figure out who the heck they're gonna audit. They [00:11:30] also use it to figure out when you did your return yourself, what is it that you messed up on. You can't claim a million business miles and not have any other amounts. The IRS knows this kind of stuff, so they're gonna send you that nasty little letter and you're gonna get scared and you're gonna go to a professional, a CPA and a growth agent [cross talk] someone who knows how to navigate those waters. Or, if you ignore it, you're gonna have that $20,000 debt hanging over your head, the [00:12:00] lien on your house. Then you're gonna do something like get married, and your wife's gonna strangle you because her tax refund got snatched, because you had this old debt you didn't take care of.
Blake Oliver: So, the bots will create more work for IRS resolution. Tax resolution. I like that.
Nayo Carter-Gray: Absolutely. I definitely see that. Then once you get a resolution client, they want to stay in compliance. So, then they know-
Blake Oliver: They learn their lesson.
Nayo Carter-Gray: Yes, they learned their lesson. They also realize, "I need someone to help me, because as much as I would love to do this myself, [00:12:30] I understand that this is outside of my scope. I may have thought I was saving some money, but it just cost me a whole lot of money to get it fixed in the long run."
David Leary: Sounds like working on the tax resolution stuff, you get- versus the regular relationship an accountant might just have somebody come in maybe once a year, do a boring old thing, do your taxes, charge you fees, see you later. You kind of get to be a hero. These people are coming to you a little bit more on the desperate side, and you get to come out ahead. Is that more rewarding to do that?
Nayo Carter-Gray: It can [00:13:00] be more rewarding. It is stressful for the clients, however, because, one, the process isn't fast, you know? It's so much faster when you just come and get your taxes done, in and out, bam. But with resolution work, you have to gather documents, and it depends on how far back they go. They have to do a little work, so, it's very frustrating. You kind of have to put the client at ease, but once it's all done, the client is then like, "Oh, such a relief!" After [00:13:30] they've already paid your invoice, because that's another thing. Resolution work can be lucrative, depending how much you save the client. Then, for example, there was a colleague who just after eight years- eight years it took them to get some penalties removed from an S-Corp client.
Blake Oliver: Eight years.
Nayo Carter-Gray: Eight years. So, sometimes it's not as fast, and clients can get frustrated, because they're like, "We want this to happen overnight." Especially, [00:14:00] they listen to the radio, and-
David Leary: Amazon Prime world [cross talk]
Nayo Carter-Gray: Yes. Yes. Amazon Prime. Social media. It's like, if I saw you checked in somewhere, I'm expecting you to answer my phone, because I know where you are. Yeah.
Blake Oliver: Well, the problem didn't develop overnight.
Nayo Carter-Gray: Yes. It's like when you gain some weight, and you go to the gym three times, and you're like, "Why didn't these 10 extra pounds fall off?"
Blake Oliver: Why not?
Nayo Carter-Gray: Right. [00:14:30]
Blake Oliver: That's right.
David Leary: A lot of the listeners can learn things from Blake and myself. Not much, but they can sometimes. But what's the one thing they can only learn from you?
Nayo Carter-Gray: This is a good question. Technology is your friend. So, I know they can learn that from you and Blake, as well, but I am a big, big, big supporter of apps. If there is something you want to be able to do, don't be afraid to go to the App [00:15:00] Store and actually look for it and search for it to make your life easier. That is the one thing that I push on people all the time. There is an app for that, for everything. You want to learn how to drink your water, eight glasses a day? There's an app that will remind you. You want to be able to ... Like, I have an app that will remind me to brush my teeth before I went to bed, because I hate brushing and flossing. It reminds me like, "Oh, go do that," and I get some points. You want [00:15:30] to save some money? There are apps out there that can help you link to your bank card and put a little extra money to the side. Although I know they can learn all of that good juicy stuff from you guys, I will push it, push it, and continue to push it.
Blake Oliver: It sounds like what you're saying is that you have to be willing to invest the time to learn about these apps, right? Because I'm sure they don't all work.
Nayo Carter-Gray: They don't all work, but, yeah ... I do tell people you spend some time on [00:16:00] the toilet every day. This is a good time to test out apps.
Blake Oliver: There you go. There you have it [cross talk]
Nayo Carter-Gray: Who doesn't take their phone into the bathroom nowadays?
Blake Oliver: Don't spend all your time on Facebook.
Nayo Carter-Gray: Exactly.
Blake Oliver: Get on the App Store, try out some new apps, and maybe that'll make you more productive.
Nayo Carter-Gray: Yes, and depending on which phone you have, they even recommend some apps for you.
Blake Oliver: Yeah.
Nayo Carter-Gray: Based on what you're looking for, right?
Blake Oliver: It's all about continuous learning, right? [00:16:30] We have to constantly invest in ourselves and our firms.
Nayo Carter-Gray: And yourself as an individual. You can't be running on fumes and then try to work and be productive during the day. You also have to take some time for yourself to make sure that you are healthy, you are happy, and that you are in a good space to tackle the day.
Blake Oliver: I like that. Well, if [00:17:00] people want to connect with you and learn more about what you're up to and your firm, what's the best place for them to reach you online?
Nayo Carter-Gray: Their best place? Oh, if you want to see all my good interesting stories, I am on Instagram. [cross talk] I love Instagram stories. I can be followed at Nayo Carter-Gray, or either 1st Step Accounting, and that's the number one - 1-S-T-S-T-E-P-A-C-C-O-U-N-T-I-N-G. I'm also Nayo Carter-Gray on Twitter [00:17:30] and Facebook.
Blake Oliver: You are the Nayo Carter-Gray.
Nayo Carter-Gray: I am the only Nayo Carter-Gray.
Blake Oliver: That's good. It's good to have unique name. I'm the only Blake Thomas Oliver. How many David Learys are there?
David Leary: There's a lot of David Learys. The worst part is if you Google David Leary, Google assumes you can't possibly be searching for David Leary and they serve up eight results of Denis Leary.
Blake Oliver: Yeah.
Nayo Carter-Gray: Really? That is really funny.
Blake Oliver: Why would you search for David Leary? [00:18:00]
Nayo Carter-Gray: Who is David Leary and why should we care?
David Leary: They think for sure you had a typo. A lot of people think his name is David Leary-
Blake Oliver: You should make a page that just explains the difference.
David Leary: That's my plan. I talked to an SEO guy, and I can make a page that says, "This is David Leary, not Denis Leary," and I put Denis Leary all over my page, and I'll actually get to top rank. I have a plan to own my own name on Google one day.
Nayo Carter-Gray: I love that, you know? SEO is huge. That's one thing that I planned on tackling this year, because that is one [00:18:30] area of my business that I just have yet to figure out.
David Leary: Blake has some lessons he can give you offline at the Salon, here.
Nayo Carter-Gray: Ooh!
Blake Oliver: That's why we're here at the Accounting Salon.
Nayo Carter-Gray: Yes.
Blake Oliver: So, let's chat later.
Nayo Carter-Gray: Okay, awesome.
Blake Oliver: Nayo, thanks So, much for your time.
Nayo Carter-Gray: Thanks for having me.
Blake Oliver: Thanks for doing the podcast. We'll talk with you soon.
David Leary: We're so glad you were on.