The Devil Made Me Do It (So I Could Pay for Bible School)

On the surface, James Rupard seemed like a stand-up guy. He was a volunteer firefighter and a pastor at the community church of his small town. When he was arrested for stealing money from the same organizations he volunteered at, people were surprised. But that was nothing compared to the shock when they found out the dark secret from his past.

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[00:00:46] America's most wanted friends.

Greg: Hello, and welcome to another episode of "Oh My Fraud", a true-crime podcast, but instead of murderers, ours features employees who embezzle tens of thousands of dollars. But every now and then, we get lucky, and we also get a murderer. Hello, I'm Greg Kyte.

Caleb: And I am one of America's most wanted, Greg. It's good to be back with you.

Greg: Most wanted friends. That's my friend, Caleb Newquist.

Caleb: That's sweet of you to say.

Greg: To launch into it, here's a question I got to you to kind of set us up for today's case is-

Caleb: Shoot.

[00:01:23] Greg's and Caleb's past jobs.

Greg: Well, first off, Caleb, about how many jobs have you had in your entire life so far?

Caleb: Well, point of clarification here, let's define job. Are we talking like employers, do volunteer jobs count, or things and activities, some illegal, some possibly illegal that made me money? I need some parameters to work with here.

Greg: Well, I mean, okay, so that totally sparks my interest. I want to know about all of the possibly illegal ways that you've made money, but specifically what I'm talking about is like employer, like W2 generating jobs.

Caleb: Okay. W2 generating jobs. It's more than-

Greg: Yeah, where you were an employee.

Caleb: Yeah. So probably close to 15. What about you, how many?

Greg: I counted them up, and if I'm remembering everything correctly, I've had 15, which seems like more than what I would have thought. If I was going to guess, I would have said less than 10. So, follow up question, how many of those jobs that you have of your about 15, because we're about the same, about 15 jobs all time.

[00:02:31] Did any of those jobs run a background check

Greg: How many, do you remember any of those jobs running background checks on you and how many do you remember having a background check on?

Caleb: I mean, I don't explicitly remember having background checks run, but I'm almost certain that virtually every job I've had as an adult probably involved a background check. I did have this one-

Greg: Oh really?

Caleb: Yeah, probably. I mean, I just don't know. The most memorable kind of related thing was I did have to take two drug tests to be onsite at a large international investment bank when I was working as a big audit's auditor. That's urine and hair - for those wondering - the urine and hair. And I think I may have gotten some low-level security clearance at some point. I don't know. I did some government jobs, so I think I had some security clearance at some point, but that expires pretty quick. And I mean, they definitely do the full Mantoux, those kinds of things. But yeah, like explicitly, I don't really remember. What about you? Lots of background checks? I don't know, how would you remember?

Greg: I swear that you have to be informed if your employer is running a background check on you. I don't think they can just sneaky, sneaky, run a background check on you. And part of my belief in that is you may not know this about your cohost, Greg Kyte, but he is currently a registered certified notary for the great state of Utah in the United States of America. It's a responsibility that's been delegated to me by the Lieutenant governor of the state of Utah, which I mean, pretty big time, pretty big time.

Caleb: As you say, it's a big responsibility being a notary.

Greg: Yeah. And no.

Caleb: I just had some stuff notarized the other day.

Greg: I have been a notary for three commission terms, and I just started my third commission term. And I had to specifically say I was okay with them running a background check on me. And they wouldn't run the background check until I told them. However, and I think this is also the case with employers, at least in Utah, they have no responsibility to inform you of the results of their background check. So that's my understanding of the dance is they have to inform you that the running one, you have to have some kind of consent for them to do that, but then after that, it's all just whatever. It's behind the curtain.

Also, I used to be a public-school teacher in a past life, and I'm confident that they ran a background check for me then because I had to get fingerprinted to be a schoolteacher. So, I'm pretty sure they're not going to take my prints if they don't run a background check on me as well. That would seem a little strange.

Caleb: Wait, whoa, whoa. Hold the phone there. Why do they need your fingerprints?

Greg: Because school teachers are the most likely makers of meth. I don't know, have you ever watched a TV show. So, I think it's to track down meth deal. That's my guess. I didn't ask.

Caleb: That was only after 2006 though, right?

Greg: Yeah.

Caleb: So, if I read your comment correctly, you approximate about 20% of the jobs you've had had background checks. Does that sound right?

Greg: Yeah, yeah, I'd say it's probably around 20 to 30% of them. So, here's some interesting stats. According to the ACFE, and we look at their stats a lot when we're doing this, they produce their biannual reports to the nations on occupational fraud.

And they say that that's barely over 50% of all organizations run background checks on employees at all. Which again, is interesting because I'm thinking it was only about 20% of my employers who did it. And of those that did run background checks, 13% of them revealed some kind of red flag, but the organization went ahead and hired those people anyways. So, some interesting stats there.

Caleb: Like one in eight employers. So, you're saying to me that all the employers that run background and then find a red flag, of those, approximately one in eight of them still hire the person. I'm just wondering, though, but I mean, let me ask your opinion as someone so knowledgeable about fraud. I mean, that seems kind of high. Is that high? That seems high. One and eight, like roughly 13%. That seems kind of high.

Greg: Right. And again, one of the things that does become difficult when we are really trying to dig into the ACFE stats is that they don't give a whole lot of like color commentary to them. And so, when they say 13% of background checks revealed some kind of red flag, I don't necessarily mean that what that means is that someone had a minor in possession of alcohol charge 15 years prior.

Well, actually I know, I do, because when you do break this down, the 13%, they do dis-aggregate that, and they say that there's 4% of those people who were charged with a fraud-related crime, and 9% of those people who were charged, but not convicted of some fraud-related crime. So those are the kinds of red flags that we're talking about, and that the organization still went ahead and hired those people, regardless of that being in their background.

There's definitely jobs that have less likelihood of committing fraud. I know that accountants is the most likely department to commit fraud, but only 17% of frauds are committed by people who are in the accounting department. So that means there's still 83% of frauds that are committed by the janitors because those are the only two departments that are in any organization is accounting and cleaning and maintenance. So, I'm just saying there's a lot of genders who are stealing a whole lot of mop heads and you got to be careful of that because that's going to affect your bottom line.

Now listener, when we come back from the break, we're going to tell you about a crazy 200,000 ish dollar embezzlement scheme, and the whole damn thing could have been prevented with a simple background check.

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[00:10:06] James Rupard and Scotland County, North Carolina.

Greg: In this episode, we're going to tell the story of James Rupard, a guy who stole $200,000 from not one, but two different volunteer firefighter organizations and some very vulnerable individuals as well. And there's a special place in hell for a guy who steals from first responders, but there's an even more special place in hell for this guy, and we're going to get to all the reasons why. But first, we're going to unpack this story just a little bit. So, Caleb, James Rupard, the story starts... Actually, where we're going to start the story is in Scotland County, North Carolina in the mid-1990s.

Caleb: Whoa, where is Scotland County, Greg? Do you have any idea where Scotland County, North Carolina is?

Greg: No one knows where Scotland County, North Carolina is because it's that rural and the population density is near zero. For all of Scotland County, for the 2019 sentences, the whole county had less than 35,000 residents. Its biggest city was Laurinburg, that had over 15,000 people in that. So that was close to half of the entire population of the whole county.

Caleb: Let me just point this out. And I've mentioned this on previous episodes, but I come from a small town. The county where I come from probably has a population density smaller than this.

Greg: Really?

Caleb: Yeah, somebody can fact check me if they want, Valley County in Nebraska. Go ahead. Knock yourselves out. But I love a small town, I love a small-town fraud, Greg. That's what I'm trying to say.

Greg: And that's exactly what this is. And I think like some of the dynamics in a small town actually helped this guy perpetrate this fraud.

[00:12:07] James Rupard was a volunteer

Greg: James Rupard, he moved to Scotland County, which again is in Eastern North Carolina. Prior to that, he lived in the far west end of North Carolina, and he moved there in the mid-1990s. So, listen to this character that we have. Everybody loved this guy. He was a volunteer with the Stewartsville Volunteer Fire Department, one of the organizations that he ended up defrauding. he also was a volunteer at the Scotland County Firefighters Association. He volunteered for the American Red Cross and for the Republican Party.

This guy was just volunteer of volunteers. He also was the pastor of the Sand Hills Community Church, and he was a licensed insurance agent, and he created a company called American Insurance Marketing, and so he does his insurance agent stuff through his own insurance business.

And one of the things that I read in the different research that I did on this case was that there was a lot of people in Scotland County who described James Rupard, or Jammie Rupard as being one of the nicest people you would ever meet. So, he was beloved in this small, small community. And again, I think that's one of the things that if you ingratiate yourself to a small community, you earn the people's trust and then you can fleece them.

Caleb: Yeah. I mean, he is definitely ingratiated. I mean, just based on the volunteer work and then having a business and then spending your Sundays doing that thing, I mean, I don't know. It seems like a busy body to prey on some small-town folk.

Greg: Right. Well, and it's interesting too because you kind of wonder what was the cart and what was the horse? Because I know he's got his business of his insurance company, and I could see a lot of people going, "Hey, if I really want to make my insurance company really work, I need to network with people. Oh, is there a way that I could be a pastor of a church? That's a great way to network with people and then I can sell more insurance during that?"

Or was it the other way around where his main thing was pastoring, and because he was a pastor of this church, he was like, "Hey, I'm going to be..." That's just where his heart was, and I'm going to start volunteering for these organizations because I'm a giver is what I am. And the insurance thing is just to pay the bills so I can do this other stuff that's more meaningful to me. That's the sort of stuff that we don't know, which was the cart, and which was the horse on that.

Caleb: But yeah, I see what you're saying, because-

Greg: People are fascinated with stories of hypocrisy is what it is.

Caleb: That's what it is.

Greg: It doesn't matter what the hypocrisy is. Wherever you're at, if you're being a hypocrite, that's always fascinating to people because you're saying one thing and you're doing another thing.

Caleb: It's a double life.

Greg: Yeah. And again, in my research, I found there are many entire websites that are devoted to clergy that have committed crimes. I think one of them was So yeah, go check that out.

Caleb: Nice domain. You nailed that one.

Greg: Yeah, it is. It is.

Caleb: Well, done.

[00:15:46] Comes into the community in 1990.

Greg: So, here's what started happening? So, he came into this community in the mid-1990s, and he immediately started doing all these volunteer work. All that stuff was almost right from the get-go from when he entered this community.

[00:16:04] Rupard opened a secret checking account

Greg: But then in 2000, Rupard, he opened a secret checking account in the name of the Stewartville Volunteer Fire Department, and he did so by forging the signatures of the fire department's treasurer and secretary at the bank. So that was in the year 2000. And then it was a year later in November of 2001 when he convinced the board of directors of the Stewartsville Volunteer Fire Department to move a $10,000 certificate of deposit from their normal bank to the new bank where he opened the secret account. And he had said that, hey, this new bank has better rates than the bank that we're at right now.

And so, this is one of the weird things about this, it's very complex. And I don't feel like James Rupard was some kind of financial genius. I think he was just making it up as he went along, and he just sort of fell into a very complex system. So, they transferred the $10,000 CD to the new bank. And then he transferred it from the CD into the secret account that he had opened earlier. And then from the beginning of 2002 to near the end of 2003, he transferred all of that money out of the secret account into his own personal accounts and other accounts that he controlled. Does that kind of make sense?

Caleb: I mean it does and yet it doesn't. Like you say, there's something that sounds kind of needlessly complex about this particular type of fraud. I mean, we're not here to do a compare and a contrast and say who's good at fraud and who's not good at fraud. But when you think about the Rita Crundwell approach, it was very simple. I mean, she did a lot of work to cover things up. And like all these new accounts and all these transferring and things, it just feels a bit messy. And like you say, it kind of gives you the impression that he was kind of just, I don't know, just winging it in a way. So pretty weird. Pretty weird.

Greg: He faked his way through this entire fraud. And this entire fraud that lasted... Well, and which is funny because is he a good fraud perp or is he a bad fraud perp. He's definitely a great fraud perpetrator because he made it onto the world's premiere fraud podcast, "Oh My Fraud". So that's the best indication. And he was able to carry this thing out for over eight years, which is a crazy long time because again, according to the ACFE, in their most recent report to the nations, the median duration of a fraud was a mere 14 months, and this guy did eight years.

So, I'm going to say he stumbled and faked his way through it. And the complexity was one of the things that helped them get away with it. Even though I don't think he knew what he was doing, I think that his needless complexity was part of what helped hide the fraud. I also believe that, like we said before, the small-town vibe and the fact that this guy was out volunteering everywhere was how he could get away with forging the signatures of the people on the board of directors for the fire department.

Because you go to a bank, you're the pastor of the church, you say, "Hey, here's the thing. I got the signatures from the people," and they go "Right on, Pastor Rupard will open that account right away." And I think that's how that happened.

Caleb: Greg, I know that Reverend Rupard stole over 200K. It sounds like it started off with 10 grands. So, what else? What's some of the other stealing he did?

Greg: I'll get to that. And first off, I realized that was actually more than $10,000 because it was a CD plus the interest that had accrued on the CD. So, it ended up being closer to $12,000 when he got his hands on it and got it out of there. Then the next step in this whole thing was in mid-2003.

[00:20:12] Next steps of his fraud.

Greg: Because again, the guy, he's an insurance salesman, he accepted $7,500 from the Scotland Firefighters Association to invest in an annuity. And instead of investing it in the annuity, he just said he took the money and didn't do anything with it at all. But one of the things that he would do is he would just create fake statements. And this is very common for fraudsters is that he's in a position of authority in a fiduciary role with the organization that he's defrauding.

When they go, "Hey Jimi, how's that annuity doing?" And he goes, "It's doing great. Let me get your statement." And then they just go make up a statement on word and print it out and hand it in and go, "Here you go." And they go, "Awesome, that looks like it's doing great for us." So that was the next 7,500 bucks. It starts getting bigger than that in October 2003. So later in 2003, he, at this point, had become the captain of the Stewartsville Volunteer Fire Department. And the fire department received $163,000 worth of grant money from Thema to purchase firefighting equipment and $38,000 of that as the captain of the Stewartsville Volunteer Fire Department, he decided to steal. So, he just-

Caleb: He showed some restraint, I think.

Greg: Yeah. Well, and again, he kind of did because... I don't know, maybe I'm going to just blow my wad with this guy right now. But when he was on trial, he said that he never intended to steal anything ever. He justified the entire fraud by saying he intended to take the money temporarily and to pay it all back in full. So, I think that's why he didn't take the whole $163,000, he just took the 38,000.

I think that's why it took him over a year and a half to bleed out the first $10,000 that he stole from the fire department because I think it was like, "It's there, I think I can pull this out, but I'm going to put it back in as soon as I make the money back." I think that part of his plan. Again, I don't think he was a smart dude. I don't think he was a financial genius.

[00:22:42] "I never meant to steal - was always planning to pay it back"

Caleb: Yeah, it's weird that I think in a lot of frauds, the idea, you hear this explanation all the time, where people are just like, "Well, I wasn't really stealing it, I was just borrowing it. And I had fully intended to pay it back." But the thing is in order to pay the money back, that either involves an unexpected inheritance, robbing a bank, or moneybag falling from the sky and landing on your fucking head.

Like I just don't know the logic that the people think it through. It's like, well, eventually, the 75,000 will show up on my doorstep, and then I'll make good on it all. I don't know. It's a very weird phenomenon in the fraud logic.

Greg: Right. And I think it's one of those things where these people are trying to... because again, if you look at a lot just the research on ethics is what people are trying to do when they make unethical decisions, rationalizing those unethical decision, is they're trying to create a narrative whereby they're still a good guy.

And so, his narrative was, I'm not stealing this, I just need it right now to get me out of a pinch, but I'm going to pay this back. And then you can continue the fantasy. And again, this is a hundred percent speculation, but I could see this with him owning his own business is he can say, "This time, I just borrowed $38,000 from a FEMA grant." And then you go, "Okay, how many annuities do I need to sell to get a commission to get $38,000 back? Oh, it's this many. Oh, I think I can swing that."

Caleb: I can do that.

Greg: And then you go, "Okay." And then you go, "Cool." And then you don't ever think about it again.

Caleb: You sell zero annuities.

Greg: You sell zero. Exactly. But he could've sold more.

Caleb: He could have. He could have.

Greg: Yeah, exactly. So just to burn through some of these other things, in 2006, he stole another $7,700 from the fire department. In 2007, which at this point, he was the president. So, at one point, he was the chief of the volunteer fire department. Now he is the president of the Firefighters Association where he stole $13,000 from the association. And then in-

Caleb: Just failing upward. I love it. Just failing upward.

[00:25:10] Rupard steps down as treasurer in 2007.

Greg: Yeah, right. Right. Exactly. He's moving on up as he commits these crimes. And then in 2007, and this was very interesting, in 2007, he stepped down as the treasurer of the volunteer fire department. So, he was the chief. He probably was doing both duties where he was the chief and the treasurer, and nobody ever really broke down the timeline of when he had what had on for this organization.

But again, small-town volunteer department, chances are he wore multiple hats at any given time. But before he stepped down as the treasurer, which I think that's interesting period that he would step down because I would think with what he was doing, he would say, "I'll be damned before I stop volunteering as the treasurer of this volunteer fire department" to just make sure nobody ever caught him.

But what he did instead, and again, this seems smart is that he opened a new not secret checking account at the same bank where he had the secret checking account. He transferred $15,000 to the new account and he totally closed the old account, which prevented the new treasurer from seeing any of the fraudulent bank account history that it had there. Because again, he was the only person who was on the secret account.

[00:26:32] Biggest mistake he makes - asks for reimbursement.

Greg: That's how he was able to transition out of treasurer and not be immediately discovered for what he did. But then the very next year, the guy makes the dumbest mistake that he's ever done, where they get another grant to go buy some equipment. And I guess they go and actually do purchase some equipment.

And then right after that, he goes to the treasurer of the fire department who succeeded him. And he goes and says, "Hey, we just bought all this equipment. I need a check from you for $26,121 because that equipment that we bought, I bought it on just out of my business's checking account, so I just need a quick reimbursement from the department. And you're welcome that I did that for you."

But again, this guy, he was beloved, and he was trusted. And so, the new treasurer was like, "Well, that's bad business." To do bad business for the fire department, bad business for your insurance company, that's sloppy. But here you go, here's your check for 26,121. Go ahead and take that. But while you go to the bank and cash that check and then immediately spend it on scratchers, while you're doing that, I'm just going to do a little digging. And at that point, they were like, "Oh shit, this guy has stolen lots of money from us over the years."

And at that time, the new assistant fire chief for the volunteer fire department had learned that Jimi Rupard, that his business phone had been disconnected, which is kind of like going, oh, something's going bad with his business because his business phone... If you have a business, you kind of need a phone for that business. That's sort of a basic office expense you got to have.

Caleb: Hopefully people can call you so they can give you money in a legitimate way.

Greg: Yeah, exactly. And so, I do think that's a red flag that maybe Jimi Rupard's business isn't going awesome is if the business phone is disconnected. And then they also just heard tell in their small town that Rupard was in serious debt, which he absolutely was. And so, the assistant chief went to the bank, he asked for all of the fire department's bank records, and that's when he was able to become apprised even of the secret bank account because remember that bank account was opened in the name of the fire department, even though Rupard was the only guy who had authority over it.

So, they gave them the records at that point, and then they were able to see all the checks that Rupard had written. And the money he took out, he didn't just send it, he gave it to himself personally. Some of it went to his business. Some of it went to other accounts that he controlled. Some of it went to his wife who then shortly after this became his ex-wife. And that's sort of the how this story unfolded. I mean, going back to just how everybody loves a good hypocrisy story.

One of the things that's awesome about this that came out is the... And again, the tallies are different for how much this guy stolen. And part of it is because how much did he alleged to steal? At one point, he was accused of stealing over $300,000 initially.

And then most of the banner headlines for the story say that he stole $200,000, but then his restitution that he was ordered to pay was about in the order of $140,000. So, none of that stuff quite lines up, and it's very difficult to find an accounting that ties out exactly what his restitution was for and how that ties out to the monies that he pulled out from this.

But one of the things that came to light during this case trial is that of the ill-gotten gains that Jim Rupard got, he did spend $2,600 of that stolen money to pay for divinity school tuition because he's a pastor, and you got to keep your Bible school chops sharp because those sermons aren't going to preach themselves.

Caleb: Yeah, thou shall not steal. I'm sure it was, I think-

Greg: Right. That was the next semester after this one. You hadn't quite gotten to that.

Caleb: They got to the 10 commandments. He skipped that semester where they talked about the 10 commandments, I guess.

Greg: Right.

Caleb: I mean, I don't know. I don't know what year this divinity school tuition came to, but $2,600 doesn't seem like a lot of money.

Greg: It doesn't seem like a lot.

Caleb: To be learning about God. To become a man of the cloth.

Greg: Yeah, that's definitely in-state divinity school too. But that's not the crazy part. Do you want to know the-?

Caleb: Oh, there's a crazy part?

Greg: There's a bombshell that also came up during this investigation.

[00:31:35] James Rupard was a convicted murderer.

Greg: The crazy part is this, is that what came out during this trial is that Jim Rupard not only stole all this money from fire departments, but from 1979 to 1994, James Rupard served a prison sentence for the shooting murders of his grandparents who raised him from childhood, from infancy.

Did you hear that? This dude was a convicted murderer, not just for murdering someone who did him wrong, he murdered his grandparents who raised him from infancy after his father died in a car accident. That's the Jim Rupard that these guys put in charge of their money and of their fire department.

[00:32:30] Thanks to our sponsor, Avalara.

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All right. So, two things come to mind. Two things come to mind. Number one, I thought there was going to be a dramatic pause there. And then number two, maybe his grandparents were jerks. I have very sweet grandparents. I don't know about you, Greg. My grandparents were very sweet people. But I had some friends.

Greg: Those grandparents who got murdered had it coming.

Caleb: Look, we're going to get into it. But you know, it's crazy that someone would kill their grandparents. But they could've had it coming. They could have had it coming.

Greg: Well, I'm going to say they didn't. Just going out on a limb saying that they didn’t, and the James Rupard was a bad person, that's where I'm going with this.

Caleb: Go on. Go on.

[00:34:01] Jim shot his grandparents.

Greg: Here's the story. If you'd like to read it for yourself, there's a link to an article in the show notes. But what they said is that... So, Jim Rupard was 17 years old. He was living with his grandparents because they were raising him. And sometime in the wee hours of the morning, there's some construction workers who are working right near his grandparents' house, and they see Grandpa Rupard running out of the house in his bathroom. They see Jim Rupard running out behind him with a shotgun.

Grandpa Rupard turns around to be like, "Don't you shoot me with that shotgun?" And at that point, Jim Rupard shoots them with the shot is what he does. And then immediately, he goes, he chucks the shotgun, and he chucks a 22 pistol into a lake because that's what murders do. And then he goes to a neighbor's house and goes, "Oh my gosh, the craziest thing just happened. Somebody shot my grandparents," failing to save that it was him that shot his grandparents. The police came to the neighbor's house. And obviously, as police do, they initially questioned him right there where he admits to the murder of his grandparents. And they said, "Why did you shoot your grandparents?"

[00:35:23] Why he did it.

Greg: And he said that they were too strict, and they were making him go back to school, and he hated school because apparently, they weren't sending him to divinity school. And Rupard, well, he told them about the guns in the pond, and so the police went to the pond, they found the rifle, they found the 22. And then, and this is where it gets a little heavy, if murder of grandparents wasn't already heavy, but they did find later that the grandpa was shot twice with the rifle and that the grandma had been shot five times with the pistol. So, yikes.

Caleb: Grizzly.

Greg: So that all happened in 1978 when he was 17. And apparently the jury, I mean, it was just open and closed. And he changed his story during the case where he said he didn't do it. And he had like amnesia, and like he just totally couldn't remember anything until all of a sudden, he started remembering that he had guns in his hands and it's like, okay, that doesn't help you convince people you didn't murder. Well, if you're like, I can't remember anything, but when I came to, I had guns in my hand and murder in my eyes, and that's his defense. I don't know how that works. The jury, they deliberated for about three seconds and we're like, "Yeah, you're guilty."

And you're going, "Oh, and he was given two life sentences for the murders of his grandparents." Yeah, that was the original sentence. But then he appealed it and on appeal, they were like, "Oh, you're only 17, you're just a kid. We can't give you a double life sentence because you're just 17, and everybody knows 17-year-olds are babies. And so, they changed it to a 15-year sentence for shooting both of his grandparents.

So that's the James Rupard that we're dealing with right here. And that leads back to the entire conversation we had about background checks. I'm going to say if these organizations did a background check on James Rupard, who ostensibly moved from Western North Carolina where he murdered his grandparents to Eastern North Carolina where nobody knew that he murdered his grandparents, that's why he moved was to start on a clean slate and to be under the radar with what he had done that was so heinous.

And so, he started a new thing over here. I'm going to say if the church, or if the volunteer fire department or the Firefighters Association, if any of them had done a background check on him and found out that he was a convicted murderer of his grandparents, they probably would have found another candidate for all of those positions. Your hot take on that, Caleb Newquist.

Caleb: Well, he clearly didn't have Atticus Finch as an attorney, but barring that, if you're running an organization, and you run a background check on someone, and they did 15 years for murder, even if you are a very forgiving and understanding person, you probably have some questions. There'd be a discussion, at least. Maybe. Probably.

Greg: I think so. And even if you were-

Caleb: I'm not saying it's an unreasonable thing. And you're saying they would probably go with somebody else, but also if this person, he gets into a community and he's very affable, and like you say, he's ingratiating himself, I think even if had come up after the fact, we have a lot of speculation going on here. So, I don't know if this is what we should be doing?

Greg: Yeah. Yeah.

Caleb: But you could say a small town-

Greg: This is our podcast. We get to speculate ad nauseum. But I like the disclaimer. This is all of us on our brains.

Caleb: But yeah, this is all on our brains. But what I'm saying is if a guy like that, even if it were to come to light, you think in a small town where he's really become part of the community, people are just like, "Well, shucks Jim, you didn't tell us about murdering your grandparents. He's like, "Well, can you blame me?" And people are like, "Nope, seems pretty understandable you'd want to get a fresh start, et cetera, et cetera." And he could carry on with the financial shenanigans and no one would be to the wiser."

[00:39:55] Would background check have made a difference?

Caleb: I guess what I'm saying is I think we end up in the same place, right?

Greg: You mean with him? If he had been transparent with that or if the background check had brought that up, that people would have been like, "Oh, I guess people murder grandparents from time to time. And so, you're good, go ahead and continue to run our fire department and our church in our small family valley in this rural community."

Caleb: Maybe I'm way off base.

Greg: Who hasn't murdered a grandparent. We all have four of them.

Caleb: Maybe I'm way off base here.

Greg: I think I'm confident that he would have been shitcanned immediately if that came to light after the fact, and if that was known before, he was given any of these positions, there's no way anyone would have given me any job except possibly a janitor at the Sandhills Community Church, and that would be it. And this is my stereotype of small rural town America. They're going to say, "Oh, we can't have a murderer as our pastor or as our fire department chief." So that would have shut it down.

Caleb: I could see that as a possibility. What I'm wondering while we are kind of speculating an armchair cycle analyzing here, what's interesting and there isn't a lot,

[00:41:24] What was his motive?

Caleb: maybe you found it in your research, but there's no indication that Rupard was... It's not clear as to the motive.

Like money troubles, yes, but there seems to be even like a psychological thing going on here where he... And I don't think we mentioned it, but he also stole money from his mother-in-law, he stole money from a widow, he stole a couple's life savings. His friend who bailed him out, he forged one of his friends who bailed him out. He forged the guy's check.

[00:42:04] Rupard forged his friend's signature on check.

Greg: We got to tell that story really quick before we get into that. So really quick, more of the timeline, Rupard was arrested in September 2009. He was indicted in November 2011. He could do a bail bond to get released and wait for his court hearing. In March of 2015, he pleaded guilty to 17 felonies and was sentenced.

But after his arrest, he has this friend, Randy Blackburn, who bonded him out of jail. And this friend of his, Randy, he was the guy you were talking about who was like, oh, he looked past Rupard's past indiscretions and he was like, "I'm going to help you because you're a friend." And so not only did Blackburn bail him out of jail, he also allowed Rupard to live with him while he was awaiting his trial and while he was this persona non grata in the community. Everyone else was just pissed and wanted to string the guy up. But this guy was the only one who stood by him through this whole thing.

But Rupard, while he was living in Randy Blackburn's house, he stole one of Randy Blackburn's checks and issued it to himself and forged Blackburn's signature to take the money. Obviously, at which point Randy was like, "What the hell are you doing, you son of a bitch?" Kicked him out of his house, and then he lost his last friend in Scotland County, North Carolina. So, yeah

Caleb: So, all this indicates to me is that it's almost like he couldn't help himself. The one person who is really walking in the path of Christ here, Reverend, is your pal, Randy.

Greg: Right. Yeah. No, absolutely. Yeah. Amen.

Caleb: Like he's the one.

Greg: Amen, Brother Newquist

Caleb: It's a plenty of Sunday school. That's not the point. The point is this person who is helping his friend in a time of need, and his friend completely betrays him, there seems to be an uncontrollable urge he cannot help himself from... If the opportunity presents himself for stealing, in this case, he was going to steal. And that's the part that I just can't get my head around is like, it's so kind of brazen and sloppy that it kind of defies comprehension. And so, in any case, it's a sad story also, is what I'm trying to say.

Greg: It is.

Caleb: It's easy to be mad at people, but also, you're just like, "What is going on?"

Greg: Right. Yeah. No, no, no. I hear you. And you kind of wonder if it's kind of like a kleptomania sort of situation where the guy, if there's money, he's going to steal it. So yeah, I a hundred percent hear what you're saying. Absolutely.

[00:45:10] A few more details- sentencing

Greg: So again, just to kind of give some of the last little details about this fraud, is basically just the sentencing. So, like I said, he pleaded guilty to 17 felonies, which interestingly left the maximum sentence for all of those 17 felonies was a little over 41 years in prison, but Rupard was sentenced to four years and 10 months in prison plus six months of house arrest. And when the sentencing came out, he'd already been in jail for 40 months. So, he only had 18 months less.

Caleb: Terms served?

Greg: Yeah. Because time already is served. So, you only had 18 months after he was actually sentenced plus those six months of house arrest. Plus, he was on probation until... Because he also was required to pay back $140,000 of restitution. Funny thing was, so all of these are well over multiple thousands of dollars, but the court also demanded that he paid back Randy Blackburn $885. So, the friend that he stole the money from while he was sleeping on his couch.

Because again, going back to what we said before, initially, he was arrested on the suspicion of stealing over $300,000, then it was found that he stole over $200,000 from these four individuals plus the two organizations. But then the restitution he was required to repay was only $141,000. So that, again, I couldn't find anything that could reconcile those numbers for me, but those are the numbers that are out there is that he was required to pay most restitution specifically to the fire department and to the Firefighters Association than what it was determined that he stole from them.

So that's weird to me as well. And those are all the beats of the story that I've got. Caleb, was there anything else that you found that you'd like to add to the case before we segue into our final segment of this show?

Caleb: You know, as far as victim goes, the only thing he was missing was orphans, I think. You got the widows, you got the first responders, seniors' life savings, no orphans.

Greg: Murdering his grandparents.

Caleb: Yeah, murdering his grandparents. Just no orphans. So, I mean, he was close to the superfecta or like the whatever, but no orphans. But anyway, yeah, that's a weird one, Greg. It's a weird one.

Greg: It's a weird one. Yeah. Weird one. But I say as weird as it is, and if you think about it too hard, it's a super bummer. But if you keep it light and keep it at a distance, it's a very entertaining story of a weirdo that stole a lot of money and did it in some real highfalutin in some... He did it in a very James Rupard kind of way. I'm going to say it like that.

[00:48:05] Thank you to our sponsor, Avalara.

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Right now, what we're going to do is we're going to look at this fraud. We're going to kind of line it up with some of the research that has been done on frauds and on fraudsters, and we're going to kind of see how this fraud compares to what we would expect from frauds. We're just going to unpack it a little bit to see if there are any lessons to be learned and what those lessons might be.

Caleb: Did we learn anything?

Greg: Right.

Caleb: What did we learn? What did we learn?

Greg: And maybe the answer's no.

Caleb: Nothing. Nothing.

Greg: Maybe we didn't learn a damn thing today. But here's some points of interest, Caleb, that I found. One of the things that's endlessly fascinating for me is red flag behaviors that fraudsters exhibit that weren't picked up on that maybe could have tipped people off earlier to the fact that, hey, we need to at least keep a better eye on this person. And again, the ACFE, they put out, well, what they consider an exhaustive list of red flags. The main red flag that we see is what the new assistant fire chief heard as a rumor around town was that James Rupard had lots and lots of debt, that he was in financial difficulty.

And that is very definitely one of the red flags that the ACFE lists. As a matter of fact, it is what they list as the second, most common red flag for fraud and that 26% of all fraudsters exhibit the red flag of being in financial problem, having lots of debt. Which makes it pretty clear that... I mean, it's clear why that's a red flag. And it makes sense that lots of fraudsters are in that situation.

Caleb: I think what's weird is that the reporting that we read and the research that we did, that there isn't more to it than that. In other another stuff that we've talked about in other webinars and other podcasts, there's just loads of red flags. And in this case, there's just not. But I guess then that just brings up the question, I guess that raises a question for me, Greg, is that there's plenty of fraud that occurs where there's no red flags, right?

[00:51:09] What if there's no red flags?

Greg: Right. And interesting that you mentioned that because I feel like that is one of the most interesting parts of the red flag research that the ACFE does. So, Caleb, you're right. That's weird. I find it weird that there's a lot of fraudsters that, again, according to the ACFE, they don't exhibit any of the red flags that they list because one of the red flags is this exactly "irritability, suspiciousness, or defensiveness". And I'd go find me anyone who's not irritable suspicious or defensive, and I am going to call bullshit because we are all that.

Caleb: I think that's the thing too. I think the people at the ACFE do find work and the report of the nations is always fascinating. But there is something kind of general and very non-specific about some of these things. And we've talked about these another in other discussions, but like a wheeler-dealer type. I'm like, the only fucking wheeler-dealer types I know more than I care to fuck think about. Especially CEO, it's like, oh, he was demanding CEOs. That is a common trait to refer to. Are you kidding me? They're all fucking demanding. And so that's the thing is like so much of it is circumstances and context.

And maybe this is all obvious, but to me, things, like you say, the pressure that a person is under, what is it? It's kind of like minority report. if you turn the fraud triangle into some artificial intelligence, people that are experiencing pressure and have rationalization and have opportunity, I mean, would that fucking fraud triangle robot be arresting people left, and right? Probably.

Greg: It would be. Absolutely. Yeah.

Caleb: Yeah. I mean, that's just-

Greg: Yeah. If it's looking for the red flag. Because again, like you're saying, all of this stuff. Because I believe how they compile the data is they go to their members, and they say how many frauds... They just ask them for a breakdown of the frauds that they investigated in that particular time period. And then they ask them for those frauds, what red flags were exhibited. And I'm sure a lot of the investigators go, "I didn't really know who the fraudster was. I didn't get into their personal life, so none." And they just leave it at that.

But then also, there's lots of subjectivity to that too, because what does financial difficulties mean? Does that mean that you...? Do I have a financial difficulty because I just went to Hawaii last week and I wasn't able to take a helicopter ride? Was that my financial difficulty in Hawaii? I would like to say yes, it was. So yeah, there's a lot of subjectivity in that.

Caleb: On the other end of that spectrum, and maybe I'm belaboring the point at this point, but if financial difficulty means, well, he's living paycheck to paycheck, it's like, all right, well, you've narrowed down the suspect list to roughly 250 million people in the country.

Greg: Right. Exactly. Exactly. That's exactly what it is.

Caleb: So, these are the things where I'm just like, you can say financial difficulty. It means something, but it also means very little.

Greg: Well, just to say that, flip it around. So that means that if 26% of the fraudsters are having financial difficulties, that means that 74% are independently wealthy. Is that what that means?

Caleb: What does that mean? I don't know.

Greg: Yeah. You can flip all of those around. So, the only other red flag that I was able to find that James Rupard exhibited was past legal problems because clearly, he had past legal problems, and 5% of fraudsters exhibit the red flag of having had past legal problems. And again, to me, that was the crux of this entire case. If they knew about his past legal problems, they would have weeded them out and he would have never had the opportunity to commit this fraud in the first place.

Caleb: Perhaps. Perhaps.

[00:55:30] The fraud triangle.

Greg: Now, the next thing I want to do really quick is I just want to go through the fraud triangle just to identify the different things that were there. The first part of the fraud triangle, and I think the most important part of the fraud triangle is the opportunity part because if there is no opportunity to commit fraud, then fraud will not be committed. Which kind of goes back to what you were saying earlier, if someone does have a criminal record, maybe hire them in positions where there isn't opportunity to commit fraud or where it's so minimal that it's immaterial.

And so, when I look at opportunity, the way that I unpack that, as I say, so what internal controls were either missing or could be overridden by this person. And when I look at this fraud, I say all the internal controls were missing and anything that was there clearly could have been overridden.

Are you with me on that? There was no separation of duties. I didn't find any idea that there was internal audits or external audits that were created. And I'm assuming that there's not going to be because either an internal audit or an external audit would have immediately surfaced the fact that this guy was siphoning money out of these organizations.

Caleb: Yeah, I think you're exactly right on this. I mean, it's a common scenario where you're in a, forget about a small town, we're just talking about a small organization and we're talking about a volunteer fire department, we're talking about a Firefighters Association. They may not even have any full-time employees. And the other thing that kind of happens in these small nonprofits is like, no one wants to be responsible for the money. So, when somebody steps up to be responsible for the money, everybody's like, "Whew, somebody is responsible for the money.

Greg: Thank goodness.

Caleb: Yeah, thank God somebody is responsible for the money. And so those circumstances put these small nonprofits and small businesses, as we've talked before, small organizations are just at a much higher risk just because there's not enough people that have the sophistication or the knowledge or even the willingness to do the jobs. And I think one thing that one point that you've made on several occasions is it doesn't have to be complicated. And so, I'm just curious, in your mind, what's a simple control that would have... I think I know the answer to this, but what's a simple control that could have been implemented in this situation?

[00:58:02] Separation of duties.

Greg: I mean, to me, the basics of internal controls is the separation of duties. Is that what you thought I was going to say? Yeah.

Caleb: No.

Greg: Yeah. Because if you've got-

Caleb: Nope.

Greg: Nope.

Caleb: Nope.

Greg: And I think it's just as easy as saying you can't authorize a check and also be the person who controls the physical check itself and the reconciliation. You have to have somebody who's not James Rupard who's authorizing checks to be written. Now, that being said, his sneakiness got him around some of that by opening the secret checking account. So then on top of that, I would have to say there's got to be some sort of just basic financial review, if not a full-blown audit of these organizations on a regular basis. Some kind of oversight that's being done.

But like you said, when you get super small organizations that are volunteer in nature that are in very in very sparsely populated communities, because like you said, small non-profits, small governments, small businesses are all disproportionately affected by fraud because they just don't have the sophistication or the manpower to do these things. So, it's like, it's easy to say here's some simple internal controls that they could have put in place, but they didn't, but then you also go... it's kind of like saying good nutrition is very simple, so why don't poor people get good nutrition. Because they don't have the money to go to whole foods, that's why they don't have the means to do that.

So, it's like, yeah, people know what they should do, but their hands are tied because they just don't have the resources to do what maybe they know they should do and maybe even what they want to do in terms of those things.

So next, and this is pretty straightforward, the rationalization. For this, we talked about before. The apparent rationalization for this. And I think this is one of the things that weirds you out, Caleb, is the only thing that we had was his... And this is the quote that he had from his hearing. He said, "I had no intention of stealing anything permanently only using it and replacing it, that I was not sinning, that I was not breaking any laws or rules."

So, he thought he was doing fine just by going, "I'm just going to borrow it for a second and then give the money back," and that was his rationalization. But it seems like you want to call bullshit on him for that? Is that true?

Caleb: Yeah. Yeah, that is true. I guess I don't... I'm a church and state person when it comes to this. The basis for your values, if you're basing your religious beliefs kind of informed the behavior that you're out in the world, you don't get to have it both ways. You can't just be like, "Well, the Bible says it wasn't sin and so it ain't sinning or it ain't wrong." There's still laws on the books that say, "Hey, you can't do that. You can't take money that doesn't belong to you. Even if you intend to pay it back, you can't take it if it doesn't belong to you." If he wasn't breaking any laws or rules, I mean, I don't know. I don't have the background in ethics to pinpoint the school of thought that this kind of lands in. But it's a pretty clear-cut case of right and wrong. It's like if you take things that don't belong to you, then it's wrong.

Greg: Right. And again, well-

Caleb: Intent is bullshit. His intent is bullshit.

Greg: Well, yeah. But I want to say that he was self-diluted. I believe this, he really thought... We already covered it. I think he really thought that he was going to be able to replace it. However, he justified that to himself, I think he thought he was really going to give the money back. And that's how he justified it to himself. Even if you could take a step back and call bullshit on-

Caleb: Are you asking me, do I think his rationalization is bullshit or do I think that just... I mean, I just want to make sure that I understand because rationalization can be bullshit, right?

Greg: Right. Yeah. Yeah.

Caleb: Just the nature because you're rationalizing something that you're... Well, you rationalize the killing of your grandparents because, well, I didn't want to go to school. I felt like the right thing to do at the time was just to kill them.

Greg: To kill them or else I'd have to go to school. Yeah

Caleb: Right. So yeah. So, there's rationale in that. It's completely wrong and potentially psychotic. But in this case, also to say that, well, my rationalization is that it wasn't really stealing, just temporarily taking it. Bullshit. So, I just want to understand if I answered your question in the right way.

Greg: You absolutely did because I was not splitting hairs like that. I wanted to know all of your opinions about this, and I think you laid them out. And then, okay, the third leg of the fraud is the opportunity rationalization and pressure. I don't think we have to spend a lot of time with pressure because really, that's just the same as red flags is that his lots of debt, that was his pressure.

And really, we touched on that before, it doesn't seem like there was really a whole lot else that was there. He didn't appear to be a raging alcoholic or a gambler or anything like that. He definitely didn't have shareholders to please or stock prices that he had to hit. So, I think it was just he was bad with money.

But that's the other thing in terms of red flags. The most common red flag is living beyond your means, that he had this real exorbitant lifestyle. And there was no indication of that. So, I think this guy was just super shitty with money and it was like, "Oh my gosh, I just spent all of our money on a car that still didn't work" or something like, I don't even.

Caleb: On giant cowboy hats.

Greg: Yeah, something. I think he was just crappy with money, and he was just a sieve for money. So yeah, so that was the pressure.

[01:04:28] Detection of fraud.

Greg: The last thing I want to talk about is detection because that's always an interesting thing is how was it detected and how does that line up with the research? So, we broke that down when we were telling about the story is that he went to the new treasurer of the fire department and said, "Hey, please..." It's where he was just a dumb ass and it was like, "Hey, I paid for $26,000 worth of equipment out of my business account. Can you just pay me back for that?"

But I think ultimately if you look at it, that ended up being a detection by a tip because he was stupid to the new treasurer and the treasurer then was like, "Hey, we need to look into this. And the new fire department assistant chief was also like, "Hey, this guy's in bad debt." That's the only way I can classify the detection was as a tip. Are you with me on that? Because the other thing that would line up is by accident because he just would-

Caleb: Well, yeah, other.

Greg: Yeah. Or other. Yeah. That is one of the categories in the ACFE is the other, which you kind of go, "Gosh what else could-"

Caleb: It doesn't feel like a tip to me just because it was a kind of a comedy of errors, I suppose. It was just one of those things where he let something slip either consciously or unconsciously, and the dude's like, "Well, that's weird." And so, they look into it, and yeah.

Greg: Well, and that's-

Caleb: I don't think they would classify that one as a tip. Again, I don't know. The ACFE people, they can sure correct us if we're wrong.

Greg: They sure could. But yeah, that's right. Because the treasurer is the guy who investigated it, so it's not like the treasurer gave the tip to himself to go, "Hey. Hey, me, I just heard that this guy was doing something weird, maybe I needed to look into that." So yeah, I guess that's not a tip. So maybe it is the other or by it. So, the ACFE says that 6% of frauds are detected by other, and yeah, maybe this is the other and maybe just being a giant dumb ass is one of the subcategories of other.

Caleb: Was one method of detection by accident. Wasn't that one?

Greg: Yeah, it is. Yeah. So, 6%-

Caleb: It might fall into that then by accident.

Greg: And again, you just go, but was it an accident? This guy didn't like accidentally to ask to be reimbursed, he just was like-

Caleb: That's true.

Greg: Yeah. So-

Caleb: No, he straight up asked for it's like, "Can I have 26 grands? Can I $26,000?"

Greg: Yeah. So, it's hard to categorize this in terms of how it's detected. Just to give some stats really quick, 43% of all frauds are detected by tip, 6% are detected by other, 5% are detected by accident. I think it's funny that 5% of frauds are discovered by accident and only 4% of frauds are detected by the external auditor, which means that fraudsters are 1% dumber than external auditors are good at detecting fraud.

Caleb: That particular fact never gets old for me.

Greg: Neither for me. And take that auditor.

Caleb: It's very satisfying. It's very satisfying.

Greg: It's satisfying. Yeah. But also, I mean, again, in terms of best practices and what people can do, if a company does not have some sort of way for like a tip hotline or some way for people to communicate their tips to management, that's just a basic thing that you got to put in there to help detect frauds early enough so they don't go on for eight years and become a $200,000 fraud and they can be... The sooner they're found, the less damage that they do. Any other things that stick out to you about this case?

And obviously, the big one that we've already hammered a lot is, do background checks. I think you got to do background checks on people. Otherwise, you're going to look horrible when it turns out that you hired a murderer.

Caleb: Yeah. I mean, in the spirit of background checks, I think something we talked about before taping was that they are kind of an imperfect thing because of there's some thorny issues around it. And because of people that have criminal backgrounds. And it's been disproportionately difficult for people of color to get back into the workforce if they've been evicted of a crime. And so, acknowledging kind of the flaws within background checks and being more mindful of how you use them I think is something that everybody should do. But I think you're right. I think that it is a simple way just to check somebody out and see what's in their past.

Greg: Right. Exactly. And yeah. And again, with that, I'm a big fan of transparency. And even if that's the whole idea of... If you are an altruistic person and you're like, hey, people can turn a new leaf, people can be rehabilitated, people deserve a second chance, if that's your take on things, I think it's still necessary that if you're a person in charge of hiring, that you do background checks and that you get that out there and say, "Hey, we're hiring this person. They murdered their grandparents when they were 17, and we're moving forward anyways. So, buckle up, County of Scotland because this is the choice we're making, and this is where we're going. So, I think when-

Caleb: We will be putting them in charge of the armory, and we won't be putting them in charge of the money.

Greg: Right. Or of the county nursing home. None of those things are going to be under their purview. So yeah. So those are the lessons I learned. Caleb, I think that kind of is an exhaustive look of what we learned, maybe not of what's possible to learn from this case. Do you have anything else to add before we then wrap things up.

Caleb: Nope.

Greg: Okay. That's it for this episode. Remember to always run background checks, people.

Caleb: And remembered to probably not hire people who murdered their grandparents.

Greg: Hey, Caleb, if people want to find you out there in internet land, how can they do so.

Caleb: Yeah, you can find me on Twitter @cnewquist, and LinkedIn, my full name, Caleb Newquist. What about you, Greg?

Greg: Twitter, I'm @gregkyte, and on LinkedIn, I'm Greg Kyte, CPA. I'm the bald one with glasses and a beard. So, if you find that picture, you found me.

Caleb: You just described most of Portland, Oregon, I think.

Greg: Right. Here's a reality of being a bald guy with glasses and a beard is we're all indistinguishable. I can't tell us apart from each other. But if you find a Greg Kyte with a shaved head and glasses and a beard, that's the right Greg Kyte. All right. And I think that's it for this episode. Caleb, you want to read this out.

Caleb: "Oh My Fraud" is written by Caleb Newquist and Greg Kyte. Our producer is Blake Oliver. Sound design, editing, and mixing by Zach Frank. If you like the show, leave us a review and be sure to subscribe to the show on Apple, Google, Spotify, or wherever you listen. Join us next time. For more average swindlers and scams from stories that will make you say, "Oh My Fraud."

Greg: "Oh My Fraud."

[01:12:09] Thanks for listening, now go earn some free CPE credit.

Blake: Thanks for listening. I hope you enjoyed this episode and that you learned something new. And if you did, wouldn't it be nice to get some CPE credit for it? Well, I've got great news. My new app, Earmark CPE, offers free NASBA-approved CPE credits for listening to podcasts, including this one. Visit to download the app, take a short quiz, and get your CPE certificate. That's

Creators and Guests

Caleb Newquist
Caleb Newquist
Writer l Content at @GustoHQ | Co-host @ohmyfraud | Founding editor @going_concern | Former @CCDedu prof | @JeffSymphony board member | Trying to pay attention.
Greg Kyte, CPA
Greg Kyte, CPA
Mega-pastor of @comedychurch and the de facto worlds greatest accounting cartoonist.
The Devil Made Me Do It (So I Could Pay for Bible School)
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