Why Compliance Gets Hard Around $500K in Donations

SPEAKER_02: 0:00

Welcome to the Nonprofit Compliance Brief, where we explain charitable solicitation and multi-state fundraising requirements in clear, practical terms for nonprofit leaders and finance teams. This podcast is produced by Ironwood Registrations.

SPEAKER_00: 0:14

It’s great to be here for another deep dive.

SPEAKER_02: 0:16

Yeah. So today we are tackling what I think is a bit of a mystery for a lot of people. It’s a mystery that a lot of nonprofit leaders face, usually right when they’re right when they should be celebrating a pretty big milestone.

SPEAKER_00: 0:30

Right, exactly.

SPEAKER_02: 0:30

Because imagine you’re running nonprofit. You know, you’re growing, the mission is taking off, things are going great, and then suddenly, right around the time you hit uh, let’s say half a million dollars in revenue, everything just feels significantly harder. Yes, harder.

SPEAKER_00: 0:44

It really does. It’s what the sources refer to as the success penalty. Trevor Burrus, Jr.

SPEAKER_02: 0:48

The success penalty.

SPEAKER_00: 0:49

Yeah.

SPEAKER_02: 0:50

That is exactly what it feels like. It’s like you hit this invisible wall, the fundraising is going well, but the paperwork, the filings, the questions from the board, it all just explodes. And the mission for our deep dive today is to really answer why. Why does compliance seem to get so overwhelmingly difficult right around that$500,000 mark?

SPEAKER_00: 1:11

Aaron Powell It’s a fascinating phenomenon. And you’re spot on to call it a mystery, because it almost always takes organizations by complete surprise. Because look, what we’re going to look at today from the materials, it isn’t a single new law that gets passed overnight. Right. It’s not like a switch flips of$500,000 that rewrites the entire tax code.

SPEAKER_02: 1:30

Aaron Powell So there isn’t some like half million dollar act that we all missed in the news. Congress didn’t sit down and just decide to make life miserable for medium-sized charities.

SPEAKER_00: 1:39

Aaron Powell No, nothing like that. What we are actually dealing with here is a tipping point. It’s this convergence where multiple completely different regulatory systems, so financial reporting, state registrations, governance expectations, they all just happen to intersect at the exact same time.

SPEAKER_02: 1:56

Wow. Okay.

SPEAKER_00: 1:57

So we want to map out that transition today. We’re going to look at the behind-the-scenes changes driving this complexity, and more importantly, talk about how you can prepare so that growth doesn’t feel like a punishment.

SPEAKER_02: 2:09

I love that phrase. Don’t let growth feel like a punishment. Because uh, in the early days, it doesn’t feel like that at all. When you are just starting out, compliance feels, well, manageable. Almost deceptively easy, I’d say.

SPEAKER_00: 2:22

Deceptively is the perfect word for it. I mean, think back to the good old days of a startup nonprofit. Why was it manageable? Usually it’s because your operations are contained. You’re likely just operating in a single state.

SPEAKER_02: 2:34

Right. You’re helping the local community. Your donors are the people you literally see at the grocery store. It’s high touch, but very low complexity.

SPEAKER_00: 2:42

Aaron Powell Exactly. And if you look at the back office, who is doing the bookkeeping?

SPEAKER_02: 2:45

Oh, usually the founder, or you know, maybe a well-meaning volunteer who happens to be good with Excel and does it on Saturday mornings.

SPEAKER_00: 2:53

Right. It’s entirely internal. Yeah. It’s informal. You file your Form 990N postcard, which, let’s be honest, takes about five minutes. Yeah. Or maybe the 990 EZ. And the states generally leave you alone because your revenue is so low, you are flying completely under the radar.

SPEAKER_02: 3:09

Aaron Powell And that creates this false sense of security, doesn’t it? You get used to the idea that compliance is a Friday afternoon task. You think, oh, I’ll just knock this out before the weekend.

SPEAKER_00: 3:18

That is precisely the trap. Because the organization is growing gradually over time, there’s this very natural assumption that the compliance work will just scale linearly. Yeah. You think if we raise 10% more money, we’ll have 10% more paperwork.

SPEAKER_02: 3:31

But the data in our sources shows that isn’t true at all.

SPEAKER_00: 3:34

Not even close. The administrative burden does not grow in a straight line. Yeah. It steps up. Think of it like a staircase. Yeah. And the biggest step, the one that trips everyone up, is waiting for you right in the mid-six sigure range.

SPEAKER_02: 3:46

Okay, let’s unpack this tipping point then. We’ve established that 500,000 isn’t a magic legal number, but it definitely seems to be the practical threshold where the systems break. So what is actually changing in the plumbing of the organization here?

SPEAKER_00: 4:01

Right. It’s a practical threshold where your administration is basically forced to catch up with your success. Several factors collide. First, your fundraising has likely expanded geographically. You aren’t just local anymore.

SPEAKER_02: 4:14

Makes sense.

SPEAKER_00: 4:15

Second, outsiders start scrutinizing your finances more heavily, grantors, watchdogs, people like that. And third, the reporting expectations from the states themselves jump up a level.

SPEAKER_02: 4:26

So it sounds like the organization’s sheer complexity starts outpacing those informal systems we talked about. The volunteer with the Excel spreadsheet just can’t keep up anymore.

SPEAKER_00: 4:36

Precisely. And the most tangible place you see this is in what the research calls the financial assurance ladder.

SPEAKER_02: 4:41

The financial assurance ladder. I like the sound of that, though it does sound kind of expensive.

SPEAKER_00: 4:45

It can’t be.

SPEAKER_02: 4:46

Walk us through this ladder because I think a lot of people just assume accounting is accounting. Numbers are numbers. Why does it get more complicated just because the numbers are bigger?

SPEAKER_00: 4:54

It’s all about who is vouching for those numbers. That is the assurance part. So at the bottom of the ladder, step one, you have those internally prepared statements. That’s what we do in the early days.

SPEAKER_02: 5:05

It’s our founder with the spreadsheet.

SPEAKER_00: 5:06

Right. Low cost, zero external scrutiny. And that works perfectly fine when you’re small. But as you grow, you hit step two, which is the compilation. This is where you actually hire an external CPA. They take your numbers and they arrange them into a proper financial statement format.

SPEAKER_02: 5:23

Aaron Powell But and this is a key distinction I saw in the notes here. They aren’t checking the numbers, right? They aren’t digging into the receipts or anything.

SPEAKER_00: 5:32

Aaron Powell Correct. In a compilation, the accountant is basically just saying if these numbers are true, here is what they look like in the correct format. They offer absolutely no assurance that the numbers are actually accurate.

SPEAKER_02: 5:42

Aaron Powell Okay, so it looks very professional, but nobody has really looked under the hood.

SPEAKER_00: 5:47

Exactly. Then you move up to step three, the financial review. Now the accountant is doing analytical procedures. They’re comparing this year to last year, asking things like, why did travel expenses double? They provide limited assurance.

SPEAKER_02: 6:00

And then step four.

SPEAKER_00: 6:01

The full independent audit, the big one. Here they are testing transactions, verifying bank balances, checking your internal controls. It provides the highest level of assurance.

SPEAKER_02: 6:12

And I assume comes with the highest bull.

SPEAKER_00: 6:14

Oh, significantly higher. We are talking thousands, sometimes tens of thousands of dollars. And here is where that$500,000 number comes back into play. Because looking at the state requirements across the country, this isn’t a choice the nonprofit gets to make anymore, is it?

SPEAKER_01: 6:28

Wait, so the state actually tells you which step of the ladder you have to be on.

SPEAKER_00: 6:32

Exactly. As you approach$500,000 in contributions, many states simply stop accepting step one or step two. They legally mandate the audit, or at the very least, a review.

SPEAKER_02: 6:43

So simply because you raise more money, the state of, say, Pennsylvania or New York might say, We don’t trust your internal spreadsheet anymore. If you want to solicit money from our residents, we need to see an external CPA’s signature.

SPEAKER_00: 6:58

Exactly. And think about the logistical reality of that shift. An audit isn’t something you could just pull off on a Friday afternoon. It requires budgeting thousands of dollars for external accountants. It requires planning months and months in advance. You have to actually have your records in a state that they could be audited.

SPEAKER_02: 7:15

And if you didn’t budget for it, if you didn’t know this invisible wall was coming.

SPEAKER_00: 7:19

Then you end up with what the industry calls a rushed engagement. You’re scrambling to find a CPA in April who is willing to take you on, which is nearly impossible, by the way. You’re paying massive rush fees, and you’re stressing your entire team out because you need that audit just to renew your state registrations.

SPEAKER_02: 7:35

That sounds like an absolute nightmare. And I feel like that connects directly to the next big stressor we need to cover, right? Yeah. The expansion of where you actually have to register. We talked about how early on you’re usually just registered in your home state. But does hitting half a million suddenly mean you’re officially soliciting everywhere?

SPEAKER_00: 7:54

Not automatically, no. But there is a very strong correlation. The sources call this the quiet expansion of multi-state obligations.

SPEAKER_02: 8:03

Quiet expansion? That sounds almost sneaky, like it’s happening behind your back.

SPEAKER_00: 8:06

It feels sneaky because it happens without a boardroom decision. You didn’t hold a vote to expand nationally, you just got better at marketing. Think about the specific things that drive growth to get an organization to 500,000.

SPEAKER_02: 8:18

Well, probably better online marketing, maybe a viral social media campaign. You aren’t just selling tickets to the local chicken dinner anymore.

SPEAKER_00: 8:25

Exactly. Your digital footprint grows, maybe you get some national marketing exposure, or here is a very common trigger that people almost always miss your recurring donors move.

SPEAKER_02: 8:36

Oh, right. I saw this in the materials. Unpack the Dave scenario for us.

SPEAKER_00: 8:40

So imagine you have a donor. Let’s call him Dave. Dave lives in your town. He gives$50 a month. He loves the mission. Well, Dave gets a new job and moves to California.

SPEAKER_02: 8:51

Okay, good for Dave.

SPEAKER_00: 8:52

Great for Dave. But he doesn’t tell you. He just updates his billing address in your credit card system, or maybe he doesn’t even do that immediately. But the money just keeps coming.

SPEAKER_02: 9:01

And you keep emailing him.

SPEAKER_00: 9:03

You keep emailing him, thanking him, sending him newsletters, asking for support. Well, suddenly you’re actively soliciting a resident of California. You have triggered a nexus in a brand new jurisdiction.

SPEAKER_02: 9:14

Just because Dave moved.

SPEAKER_00: 9:16

Just because Dave moved. And California, as you might guess, has very strict rules. If you are soliciting their residence and receiving funds, they expect you to be registered.

SPEAKER_02: 9:26

So you can easily have 10 Dave’s moving to 10 different states over a couple of years.

SPEAKER_00: 9:31

Precisely. So even though your office hasn’t changed and your staff hasn’t changed one bit, your compliance obligations have expanded geographically. You are now playing by the rules of five states or 10 or 20.

SPEAKER_02: 9:43

And that leads to what the outline calls the administrative complexity. It’s not just that the rules are harder, it’s that there are just so many more of them.

SPEAKER_00: 9:50

Yes, it’s a volume issue versus a complexity issue. The form for registering in Georgia isn’t inherently that different from the form in Florida. They ask for similar things: your 990, your bylaws, your board list. But when you multiply that process by 20 states, it’s chaos. It is absolute administrative chaos. Because the deadlines aren’t the same. Georgia’s due in November. California might be due in May, depending on your fiscal year. You end up with a constant dripping stream of document gathering.

SPEAKER_02: 10:20

It sounds like a full-time job.

SPEAKER_00: 10:22

It really becomes one. And this brings us to the coordination crunch. In a smaller nonprofit, say sub 500K, the person raising the money and the person counting the money might literally be the same person, where they sit right next to each other.

SPEAKER_02: 10:36

Right. They basically share a brain.

SPEAKER_00: 10:38

Exactly. But as you grow to that$500,000 level, those teams have to split. You hire a dedicated development director, you hire a CFO or bring in a contract accountant. And they often operate in completely different worlds.

SPEAKER_02: 10:52

Oh, I have seen this happen. The development team is high-fiving in the hallway because they launched a great campaign in Florida. And the finance team is hyperventilating in the back room because nobody told them they need to register in Florida.

SPEAKER_00: 11:04

Precisely. The friction point is very real. At this stage, compliance is no longer just about filing a form, it’s about coordination. Finance needs to know what development is planning before they launch. And development needs to know where they are actually legally allowed to ask for money.

SPEAKER_02: 11:22

That is a massive cultural shift for an organization. It stops being just isolated paperwork and starts being about internal communication. It does.

SPEAKER_00: 11:30

And that cultural shift ripples all the way up to the board of directors.

SPEAKER_02: 11:33

Yeah, let’s talk about the board. Because usually in the good old days, they just want to know: did we hit our fundraising goal? Or is there enough cash to make payroll this month?

SPEAKER_00: 11:43

Aaron Powell In the early days, yes. It’s very much a survival mindset. But as the organization matures, the board’s fiduciary duties become much more tangible. They start asking much tougher questions.

SPEAKER_02: 11:54

Aaron Powell Like what? What changes?

SPEAKER_00: 11:56

Well, instead of just asking if the bills are paid, they start asking, are we compliant?

SPEAKER_02: 12:01

Aaron Powell Are we compliant in every state where we solicit? That is a scary question if you don’t actually know the answer.

SPEAKER_00: 12:08

Aaron Powell It is terrifying for a leadership team. The board will ask, do we need audited financials now? Who is actually responsible for tracking this? Is the CFO, the development director. Trevor Burrus, Jr.

SPEAKER_02: 12:18

So it shifts from a maintenance mindset, kind of like paying the light bill, to a full-on risk management mindset.

SPEAKER_00: 12:23

Exactly. Compliance becomes a core part of governance. The board starts to realize that failing to comply isn’t just a nuisance, it’s a severe reputational risk. Because if a major donor looks you up on charity navigator, or they check the state charity database and see not in good standing or registration expired, that hurts trust.

SPEAKER_02: 12:43

And trust is the primary currency of the nonprofit world. You can survive a bad quarter, but you really can’t survive a loss of trust. Okay, so if I’m listening to this and I’m thinking, uh-oh, this sounds a little too familiar. Or maybe I think I might be the one sweating in the finance office right now. What are the warning signs? How do I know if I’m currently entering this transition zone?

SPEAKER_00: 13:05

There are a few classic indicators highlighted in the source material. First, look at your mail or your email. Are you seeing a sudden increase in letters from state regulators?

SPEAKER_02: 13:15

Like what? Dear sir or madam, where is your form?

SPEAKER_00: 13:18

Pretty much. Or request for clarification. Things like, we see you reported X amount of revenue on your 990, but you filed a waiver with us. Please explain. If you get one of those, maybe it’s a fluke. If you get three, it’s a pattern.

SPEAKER_02: 13:33

That’s a huge red flag. What else should they look for?

SPEAKER_00: 13:35

Second, listen to your grant makers. This is a big one. Are they asking for more documentation than they usually do? Are they saying things like, we can’t release these funds until we see your audited financials?

SPEAKER_02: 13:44

That’s a massive one because that directly hits the revenue. That’s not just annoying paperwork, that is lost money.

SPEAKER_00: 13:51

Exactly. Third, listen to your accountant. If they are proactively suggesting upgrades to your financial statements, do not ignore them. They are seeing your risk profile change. And finally, look at your internal systems. Are your spreadsheets failing? We have all been there. If you are missing deadlines because the spreadsheet wasn’t updated or someone messed up a formula, or if you can’t confidently tell which states you are registered in without digging through three different folders, you have outgrown your systems.

SPEAKER_02: 14:22

So if those red lights are flashing all around you, what is the survival guide? How do we navigate this without completely burning out the staff?

SPEAKER_00: 14:30

The sources point to four key strategies here. The first step is to centralize. You simply cannot manage multi-state compliance on sticky notes or scattered desktop files. You need a central tracking system, whether that is sophisticated software or just a very robust, tightly controlled shared cloud system.

SPEAKER_02: 14:48

Just one single source of truth.

SPEAKER_00: 14:50

One source of truth where anyone can look and immediately see, are we good in Ohio? Second strategy, align. You have to force regular communication between the finance and fundraising teams. Make them have lunch together, make them sit in the same quarterly planning meetings.

SPEAKER_02: 15:07

Before we launch this campaign, let’s check our registrations.

SPEAKER_00: 15:10

Exactly. Third, review. Conduct a formal annual review of your obligations. Don’t just assume what you did last year works for this year. Remember, Dave might have moved again.

SPEAKER_02: 15:20

Classic Dave, keeping everyone on their toes.

SPEAKER_00: 15:23

Always. And the fourth strategy, anticipate. Budget for those financial reporting upgrades before they are strictly required.

SPEAKER_02: 15:30

That is great advice. It’s so much better to have the audit budget ready and not need it than to need an audit and have no money to pay for it.

SPEAKER_00: 15:36

Absolutely. It turns a potential crisis into a simple line item.

SPEAKER_02: 15:40

You know, we’ve talked a lot today about the burden, the complexity, the cost. And I imagine for some listeners, this feels a bit heavy. Like, why did I even bother growing if it just means more headaches?

SPEAKER_00: 15:51

It is a very common feeling, the whole YME syndrome. But I really want to reframe that.

SPEAKER_02: 15:55

Please do. We could use the silver lining.

SPEAKER_00: 15:57

The silver lining is that this pressure is actually a positive signal. High compliance expectations are a proxy for trust. They are a proxy for reach. The fact that state attorney generals care what you are doing means you matter.

SPEAKER_02: 16:12

That’s a really healthy way to look at it.

SPEAKER_00: 16:14

It really is. Increased compliance requirements are essentially a certificate of growth. It means you have broader institutional reach now. It means donors trust you enough to give you significant amounts of money.

SPEAKER_02: 16:26

So the pain is really just a growing pain.

SPEAKER_00: 16:28

It is. Think about it. When you can put the platinum transparency seal on your website, when you can look a major donor in the eye and say, here are our audited financials, we are fully compliant in all 50 states, that closes the deal. It signals incredible maturity.

SPEAKER_02: 16:43

So it stops being a barrier and literally starts being an asset.

SPEAKER_00: 16:46

Exactly. And to bring it back to the core theme we see in the research, compliance tends to expand alongside fundraising growth. And organizations that review requirements periodically avoid most problems. It’s not about avoiding the work entirely, it’s about managing it so it supports your mission rather than detracting from it.

SPEAKER_02: 17:06

That is a fantastic takeaway. So if you’re drowning in paperwork right now, take a deep breath and pat yourself on the back because it means you are succeeding.

SPEAKER_00: 17:15

In a way, yes. You’ve officially leveled up.

SPEAKER_02: 17:17

I want to leave you, our listeners, with a thought to mull over. We so often look at compliance as the department of no or the department of slowing things down. But based on what we explored today, think about this. Compliance isn’t getting harder because you’re doing something wrong. It’s getting harder because you’re doing something right. You are building something that is big enough to require scaffolding.

SPEAKER_00: 17:39

That is the perfect way to frame it.

SPEAKER_02: 17:41

Thank you so much for breaking this down for us. It’s a dense topic, but understanding the why behind it really changes the perspective. If you found this discussion helpful, you can find additional compliance guides and visual resources at ironwoodregistrations.com. Thanks for listening.