Tax Fear Is Costly: CPA Nathan Caldwell on Avoiding Expensive Business Mistakes

Nathan Caldwell (00:00)

Yeah, so in today’s day and age, and I think I mentioned this briefly before a call to you Quentin, is that we’re in this gig economy where everyone is their own entrepreneur in a sense, whether it’s door dashing, Ubering, whatever it might be. ⁓ And a lot of people are finding themselves in a lot more of a complex tax situation than they would have otherwise. And it’s okay to be afraid to do your own taxes.

Quentin (02:01)

Hello everyone. Welcome to the Real Estate Pros podcast. I am your host Q Edmonds and I am excited to be here today. I have another fantastic guest who has a fantastic subject matter that we’re going to hit on. Taxes. No, don’t get scared. Listen, don’t get scared. Listen, I’ll tell you, you want, you want to hear what this gentleman has to say about taxes, especially if you are foray into the entrepreneurial world, sometimes for the first time.

Sometimes that taxing is going to be very daunting if you don’t have an experience in filing, especially when you are a business owner. I love the way this gentleman thinks, thinking, actually thinking to change the landscape. And so I’m so excited for us to get to talk to Mr. Nathan Caldwell. Mr. Nathan, how are doing today,

Nathan Caldwell (02:50)

I’m doing great, Q, it’s a pleasure.

Quentin (02:52)

Absolutely, man. So glad you’re here. So happy to have this conversation. And listen, I’m a type I like to dive right in. So I would love for you to tell the people what’s your main focus these days. If you don’t mind, give us a little bit of an origin story, kind of how you got into the space that you’re in. We love origin stories. And let them know what part of world you’re in as well. People love to know where you are geographically. So what it is you’re up to, your origin story and where you are. Mr. Nathan, sir, you have the floor.

Nathan Caldwell (03:20)

Absolutely. So ⁓ I’m a certified public accountant. I’m in Charlotte, North Carolina. ⁓ And I kind of grew up in the accounting industry. My mother owns a CP or a bookkeeping firm, rather, ⁓ over on the coast, Wilmington, North Carolina. So anyone knows where that is? It’s a great vacation spot. If you haven’t been, it’s about an hour and a half north of Myrtle Beach. So for that vacation, skip Myrtle Beach next time. Go to Wilmington. Wilmington’s much better.

Anyways, so I got my bachelor’s and master’s degree from UNC Wilmington. So I moved in 2023 from Wilmington to Charlotte, the banking capital. And I worked for a large accounting firm here, one of the top 10 accounting firms in the world. They’re a large multi-national firm by the name of Forvis-Mazars and got some wonderful experience there.

Quentin (04:03)

Mmm.

Nathan Caldwell (04:19)

working on some huge projects, lots of private equity, real estate investment, and even real retail space ⁓ as well. So we got to see a lot of different things. And it was kind of during that time where I realized, you know, maybe I’m not that good of an employee, and I may not be in the right space. So I left that position almost a year into it and decided to ⁓

Quentin (04:37)

Yeah.

Nathan Caldwell (04:48)

open my own firm, give that a shot. Because at the time, I didn’t really have a lot to lose, ⁓ not a lot of personal expenses. ⁓ So hit the ground running. And for the first, I want to say, you know, three, four months, it was

pretty ⁓ miserable. Lots of marketing, lots of ⁓ door to door, ⁓ you know, trying to trying to get my name out there and network. ⁓ But once the traction caught on, was

I realized that I had made the best decision for myself as an entrepreneur. And as entrepreneurs, we understand that we have this mindset where we’re not going to be and we’re not going to feel like we’re in the right spot if we’re working a WQ job or for an employer. So once you make that leap, it’s like you feel like this burden’s been lifted off your shoulders, even though you have a lot more risk than what someone who’s maybe not as entrepreneurial as us

may think, gosh, well, the risk is too much. For us, it’s like you feel like you’ve spread your wings, you know, and that freedom is, is really, really nice. But ⁓ that was 2024, ⁓ August 2024, when I started. And ⁓ since when I when I first started, I had, I think, two or three clients. And now we are approaching 300 clients.

Quentin (06:39)

Yeah. ⁓

Boy.

⁓

Nathan Caldwell (07:01)

So

it has been an absolute pleasure. love all of my clients that I work with. They love working with us. It’s been so much fun being client facing, ⁓ being able to deliver the value firsthand instead of being in ⁓ a sweatshop of an accounting firm, if you will. ⁓ So that’s kind of where we are now.

Quentin (07:21)

⁓ Nathan, man, sir, thank you. Thank you for taking us through the journey. Thank you for telling us where you are now and then just walking us up into, the journey to how you got to where you are. And as you was talking, I was actively listening and I’m gonna say some things back to you that you said, kind of summarization. So, mom owns a bookkeeping in Wilmington, North Carolina. And so you kind of grew up in the bookkeeping business. ⁓ Went to, I think you said UNC Wilmington. Did I get that right?

Nathan Caldwell (07:50)

That’s correct.

Go Seahawks.

Quentin (07:51)

Don’t see how it’s got masters

and bachelor’s. I mean, worked for a top 10 accounting firm, got great experience from it. But then you was like, you know, maybe I’m not in the right space. Like maybe this employee stuff does not cut out for me. So you left there at the stretch and left and started your own firm. The start was a little bit miserable. But then after the start, I mean, you knew that this was the right fit.

So August, 2024, when you saw the business from two clients to 300, was that a pretty good summarization? Man. And so I did that summary because I often say destiny has no wasted moments, right? Meaning no matter the journey, no matter what leg of the journey we on, we are actually learning something about ourselves and we’re taking part of that lesson and we’re applying it and we continue to grow.

Nathan Caldwell (08:28)

Absolutely.

Quentin (08:49)

We continue to grow and we’re building momentum to the people that we are today and we find success based on the journey. And so Nathan, would love to know, man, throughout your journey, what has it taught you or revealed to you about yourself? Has it revealed discipline, resilience, innovation? Like what is the journey revealed to you about you?

Nathan Caldwell (09:10)

Yeah, so that’s a very, very important question. ⁓ I’ve always been what I call a toxic overachiever. When I was in college, even when the grades didn’t matter in grad school, it was like, well, I want to get an A in everything. And so I always had kind of the spirit of excellence in everything I do. I want to not leave a conversation open-ended, to not leave ⁓ an answer to a question with doubt.

That’s kind of just who I am as a person. I’ve tried at times to maybe stray away from that because it can be exhausting, but that’s kind of perfectionist and ⁓ that strive for perfection is, that’s just something that’s in my blood and I can’t get rid of. one thing that I’ve been thinking about, because people, ⁓ some of my friends and family have congratulated me and

you know, you’ve…

you know, done quite well and you know, I’d say you’re successful. So congratulations on your success. And I always stop them and say, no, success is ongoing. And if at any point in time I stop and say, I’m successful, I’ve arrived, I’m ultimately doomed to So that’s one of those things I’m constantly learning and adapting. And I know I’m not perfect. And I always tell my clients, if I don’t have an answer to a question, I’m going to admit, I don’t have the answer to that question. I’m going to find out for you. And let’s find out and learn together. So that’s one of those things that

Quentin (11:04)

Yeah. Yeah.

Nathan Caldwell (11:09)

I’ve learned along my journey, it’s okay to make mistakes, ⁓ be humble and admit when you don’t know the answer and strive to grow and continue to get better because that’s what success is, it’s ongoing.

Quentin (11:23)

Man, thank you for that answer. Thank you for that just reflective answer. I greatly appreciate that. And I love how you brought up the spirit of excellence. And so we know along the journey, adversity is going to show its head, right? mean, nothing is always smooth sailing. And so you got the spirit of excellence, but I also know adversity had to creep its head up. So how does adversity look in your world and how do you handle adversity when it comes?

Nathan Caldwell (11:53)

man, it’s in many different forms. First and foremost, internally, ⁓ kind of this, ⁓ what’s this imposter syndrome. When I first started, I was like, well, are you, you qualified for this? Are you deserve to do this? That’s first and foremost, the biggest obstacle for me is internally is getting over that imposter syndrome. Because if you allow it to consume you, you’re not going to grow like you’re

Quentin (11:55)

Mmm.

Nathan Caldwell (12:22)

like you want because you’re going to say, oh, I can’t do that. I’m not qualified for it versus saying, okay, this is something that’s going to be a challenge to my skill set. Let’s hone in on the CPE. I need to get 40 hours a year anyways. Let’s learn more about this subject matter and let’s see how we can deal with this question, how we can service this type of clientele because

You never know until you actually start studying a certain area of the market, especially when it comes to taxation. ⁓ Even to pass the CPA exam now, it covers a football field length and information, but it’s only about an inch deep. You can go deeper and deeper and deeper and deeper. It’s crazy how in-depth you can get into certain areas of the tax law. ⁓ Take that first step and…

Don’t be afraid to say yes and try to learn. And if you learn and it’s not for you, you can take a step back. But overcoming that first ⁓ internal struggle of the imposter syndrome, that’s the biggest one for me at least, the biggest challenge.

Quentin (13:32)

Such great wisdom. I he was speaking straight to me because I’m constantly trying to quiet that voice of the imposter. Constantly trying to do it. And so, man, thank you. think that was such great wisdom. Let me ask you this. What is the next real goal? Like, what are you looking to solve or scale next with the business?

Nathan Caldwell (13:49)

Yeah, so right now the number one thing we see this in news headlines everywhere is AI. AI is coming for your jobs, AI is gonna do this, AI is gonna do that. No one’s gonna be able to work in a decade or whatever. There’s a lot of fear mongering that’s going on. We’re kind of in the situation where you have to get on the train or get out of the way, because you’re gonna get run over if you’re not on the train. So there’s a lot of really, really cool tools and AI resources that have come on the market that can help us as taxpayers

professionals deliver more value and scale and maybe tap into a market that hasn’t really been tapped into before. ⁓ That’s going to be very, very important, especially in the next five years. And we’re already looking at building an AI bot to assist with some everyday administrative accounting needs for us. And it’s doing quite well, actually. Right now, we’re kind of in the development stages. ⁓

But ⁓ if that’s successful, that can take the workload of another part-time employee and the people who I actually have working for me right now, working with me, ⁓ they can focus on things that are going to provide more

and they can grow and scale their businesses and whatever it is they’re doing, their expertise more. So we can kind of share the wealth in that respect. So I feel like looking at it as an opportunity versus a

is going to be a lot more ⁓ of an important mindset to have. Because again, if you look at AI as a threat, you’re not going to want to invest in it. You’re not going to want to actually adopt it. And you’re ultimately going to be the one doomed to fail.

Quentin (16:15)

man, yes, yes, I think. Man, you’re so spot on. And I am going to absolutely love asking you this question because we interact either with people as clients or employers, employees, or we interact with ourself. So I’m going ask you this word and I want to hear your opinion on this, the word relationship. When you hear the word relationship, what comes to mind to you,

Nathan Caldwell (16:45)

So relationships are a two-way street. So in order to foster a relationship, you’ve got to be a good connection. You’ve got to be a good fit for the other person, whether it’s a client or whether it’s a coworker. For us, for me, for example, my client’s relationships are very important to me. And if at any point in time I feel like

Quentin (16:47)

Mm. Mm.

Nathan Caldwell (17:10)

this client may not be a good fit because maybe their personality is this way and they’re, you know, maybe it’s, hey, it’s my way or the highway type of client as I like to call them. Maybe it’s not a good fit because maybe I’d want to work with someone who’s a little bit more open-minded, right? So relationships are definitely two-way. ⁓ You want to make sure you’re a good fit for the person you’re working with and the other person likewise. You want to be a good fit for them. That’s how I view relationships. Relationships, that’s what business is built

Because without that, are you really gonna be successful as an entrepreneur, as a business owner? You’re not.

Quentin (17:46)

Man, listen, I am loving everything that you’re saying. I love the way you think. And so I’m going to ask you this, probably maybe the last question I’m going ask. Is there anything that any topic I have not brought up that you would like to talk about? Or is there any kind of other words of inspiration, education, motivation that you want to give? Because if you came in here with a certain message in your mind, like, I want to make sure the viewers get this. I just want to open up the floor so you can land that message.

Nathan Caldwell (18:15)

Yeah, so in today’s day and age, and I think I mentioned this briefly before a call to you Quentin, is that we’re in this gig economy where everyone is their own entrepreneur in a sense, whether it’s door dashing, Ubering, whatever it might be. ⁓ And a lot of people are finding themselves in a lot more of a complex tax situation than they would have otherwise. And it’s okay to be afraid to do your own taxes.

Don’t just take that 1099 input in TurboTax and then say, okay, we’re good because TurboTax asked me the questions. It looks fine, right? In reality, a lot of these self-prepared tax softwares are going to make these underlying base assumptions. On the back end, you’re not going to see, and you’re not going to understand unless you have a base level of understanding of the US tax code. And maybe you are a tax professional yourself. So don’t be afraid to reach out to a professional.

even if they may be a little bit more expensive than using TurboTax, know, reaching out to a professional, finding the answer and getting an answer that’s A, gonna save you money under tax bill and give you assurance. ⁓ That’s very important rather than just, you know, doing that and saying, let’s just get into TurboTax. It looks good. We’re fine, you know? And when waiting to last minute is also something that is detrimental to…

you know, someone’s success financially because on Spaceship we’re on the first of April and we’re getting things on TurboTax and then you turn out and you owe $10,000 and you’re like, why do I owe this much? You may be waiting too long. So be proactive rather than reactive and then don’t be afraid to ask questions when you need to. I will say, I will caution our listeners here, ⁓ chat GPT is only so useful when it comes to asking tax questions.

those language learning models, there’s actually specific ones built for tax professionals. ⁓ There’s one for us tax professionals, for example, called ⁓ Tax GPT. And it’s for accounting firms only. And it’s an AI that is built around the US tax code. So these language learning models, they can get very, very, very specific and advanced on one topic of subject matter. Chad GPT is very generalized.

Don’t ask chat GPT a very specific tax question, you’re gonna get a very general answer. You wanna just seek out a professional help. But again, it’s important to not be afraid to be proactive.

Quentin (20:40)

Yeah.

Such great wisdom. Nathan, such great wisdom, sir. I so appreciate you being here. If someone wanted to reach out to you, connect with you, collaborate with you, learn more about what you’re doing, how can they get in contact with you,

Nathan Caldwell (20:58)

Yeah, absolutely. So we have a website and it’s very, very easy. There’s no www. It’s just NathanCaldwellCPA.com. It’s my name CPA.com, no spaces. And there’s an area for you to visit for to submit an inquiry and we’ll reach out 24 to 48 hours, schedule a call and see how we can help. I give all of my clients a free consultation to see, to listen.

understand what their problem is and how we can solve it and whether we’re going to be a good fit to address those issues for them. Because ⁓ that’s one of those things as tax professionals we’re really, really bad at is listening. ⁓ Oftentimes the status quo for accounting firms is you send an email and you never hear back. It goes into an abyss and it just disappears. I like to be that listener here and I like to be that ⁓ advocate for my clients. So again, don’t be afraid to reach out.

You can do it directly through our website, ⁓ nathancaldwellcpa.com.

Quentin (22:03)

Nathan, I want to say, man, to you three things. One, thank you for your time. You could have been anywhere in the world. Time is our most precious commodity. You hit on it, right? The culture is changing. You said it so eloquently earlier, the times have changed. So time is our most precious commodity. Thank you for your time. Secondly, thank you for your story. Thank you for your narrative. I believe when we tell our narratives and we can tell what we do, has a way of planting seeds in people that literally can course correct them.

So I believe the information that you gave today can literally save some businesses, like literally. So I thank you for sharing your narrative. Lastly, thank you for your perspective, for your mindset and bringing that mindset, expertise, that knowledge to this platform. I greatly appreciate you coming on, sir.

Nathan Caldwell (22:50)

Absolutely, it’s a pleasure Quentin, I appreciate it.

Quentin (22:52)

Absolutely. listen, y’all heard Mr. Nathan. Listen, look into the show notes. His information is there. Get in contact with him. Get these taxes shorted up. But definitely make sure you’re subscribed here because I promise you we’re going to continue to bring up amazing people just like Mr. Nathan. So sir, I say thank you again. And everyone else, you have a fantastic day.