When Compliance Starts Affecting Fundraising Strategy

SPEAKER_01: 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 is so good to be back. And uh today is actually going to be a little bit different for us.

SPEAKER_01: 0:19

Yeah, definitely different.

SPEAKER_00: 0:20

Because we aren’t just looking at a specific tax form or dissecting a particular state rule like we usually do. Today we are talking about growing pains.

SPEAKER_01: 0:29

Which is something you know every listener implies when they tell you, hey, we had a really great year. Exactly. I was looking through the research for this deep dive, and there is this recurring theme that stood out to me: the tipping point.

SPEAKER_00: 0:39

The tipping point, yes.

SPEAKER_01: 0:40

It almost reads like a movie script. The hero, in this case, your scrappy startup nonprofit, overcomes the odds, they start winning, and then suddenly they realize that uh winning is actually really complicated.

SPEAKER_00: 0:55

It really is.

SPEAKER_01: 0:56

We are looking at that specific moment where compliance stops being this annoying thing you do for an hour on a Friday afternoon, and it suddenly transforms into the main thing that decides whether or not your fundraising strategy actually works.

SPEAKER_00: 1:10

That is the pivotal moment for any organization. It’s when the administrative burden just it starts being a footnote and it becomes a headline.

SPEAKER_01: 1:18

Right.

SPEAKER_00: 1:18

What we want to really unpack today is the trajectory of that growth. You know, why do regulatory requirements start dictating how and when you fundraise as you get bigger?

SPEAKER_01: 1:28

And more importantly, how do you keep that momentum going without getting completely tangled up in red tape?

SPEAKER_00: 1:33

Exactly. Because usually when compliance starts affecting your strategy, it just feels like hitting a brick wall.

SPEAKER_01: 1:38

Yeah, and nobody starts a nonprofit to fill out state paperwork.

SPEAKER_00: 1:42

No, definitely not.

SPEAKER_01: 1:43

They started to fix a problem in the world, and the sources describe the early days of a nonprofit as the wild west. I just love that imagery.

SPEAKER_00: 1:51

It fits perfectly, doesn’t it? In that wild west phase, you are a startup. Decisions are driven almost entirely by your mission and by immediate opportunities.

SPEAKER_01: 2:01

You see a need, you have an idea, and you just ask the people around you for money to fix it.

SPEAKER_00: 2:06

Right. It’s the kitchen table era.

SPEAKER_01: 2:08

Yeah.

SPEAKER_00: 2:08

You have a laptop, maybe a basic website, and you are literally Venmoing money around.

SPEAKER_01: 2:14

You’re blasting emails to your college roommate, your cousin, uh, that guy you met at a conference three years ago.

SPEAKER_00: 2:20

Yeah.

SPEAKER_01: 2:20

It is chaotic, but it’s incredibly fast.

SPEAKER_00: 2:24

Aaron Powell Speed is the ultimate currency at that stage. If a disaster strikes or if a news story breaks that directly relates to your mission, a startup can launch a campaign in an hour.

SPEAKER_01: 2:35

Aaron Powell Literally an hour.

SPEAKER_00: 2:37

They throw up a social media post, they send an email blast, and the money just starts coming in. There is very little friction.

SPEAKER_01: 2:42

Aaron Powell But is that because there are actually no rules for startups, or is it just because no one is paying attention to them yet?

SPEAKER_00: 2:47

Aaron Powell Well, it’s a bit of both, but mostly it is a matter of scope. Compliance exists, absolutely.

SPEAKER_01: 2:52

Okay.

SPEAKER_00: 2:52

But in this phase, it’s dormant.

SPEAKER_01: 2:54

Dormant.

SPEAKER_00: 2:54

Dormant, okay. You probably filed your 990N postcard. Maybe you registered in your home state where you incorporated. But because your revenue is low and your donor base is strictly local, mostly friends and family, the heavy regulatory machinery just hasn’t kicked in yet.

SPEAKER_01: 3:10

You aren’t tripping over the wires because you aren’t moving far enough to actually hit them.

SPEAKER_00: 3:13

Exactly. You are flying under the radar. But then your strategy works. You grow.

SPEAKER_01: 3:19

Which is the goal.

SPEAKER_00: 3:20

Right. And this is where the entire dynamic shifts.

SPEAKER_01: 3:23

Yeah.

SPEAKER_00: 3:23

The Wild West ends not because you failed, but because you succeeded. Aaron Powell, Jr.

SPEAKER_01: 3:28

Which is such a weird paradox. The the trigger for all this headache is almost always expansion, right? Specifically geographic expansion.

SPEAKER_00: 3:35

Aaron Powell That is the trigger. As your revenue increases, you naturally look for new donors. And where are those new donors?

SPEAKER_01: 3:42

Everywhere.

SPEAKER_00: 3:43

They are everywhere. They are not just sitting in your home state anymore.

SPEAKER_01: 3:46

Aaron Powell And this is where I think a lot of leaders get completely blindsided. They think, well, it’s the internet. I can ask anyone for money.

SPEAKER_00: 3:52

Oh, we hear that all the time.

SPEAKER_01: 3:53

Right. I mean, if I tweet a donation link, I’m not specifically targeting someone in Florida. They just happen to see it on their feed.

SPEAKER_00: 4:00

Aaron Powell That is probably the single most common misconception out there. The internet creates this illusion of a borderless fundraising environment, but the laws are still very much based on physical borders. Aaron Powell So sending a general tweet is one thing, but once you start actively targeting donors, like sending marketing emails to a list that specifically includes people in California, or running Facebook ads that are geo-targeted to zip codes in New York, you have crossed a legal line.

SPEAKER_01: 4:29

Aaron Powell Okay, so the strategist session fundamentally changes. It used to be just how do we get the money?

SPEAKER_00: 4:34

Right.

SPEAKER_01: 4:34

Now someone in the room has to raise their hand and ask, wait, where does that donor actually live?

SPEAKER_00: 4:39

And that single question kills the momentum. Because the rule in most states is that you must register before you solicit.

SPEAKER_01: 4:46

Okay, we need to pause on that. The word before, because in the real world, does that actually happen? If I’m a development director and I have a massive hot lead in Texas, am I really going to wait four weeks for a state registration approval before I send that introductory email?

SPEAKER_00: 5:02

That is the million-dollar risk question right there.

SPEAKER_01: 5:05

Yeah.

SPEAKER_00: 5:05

In practice, a lot of organizations solicit first and try to clean up the mess later.

SPEAKER_01: 5:10

Which sounds incredibly risky.

SPEAKER_00: 5:12

It is a very dangerous game. If you launch a deliberate expansion into highly regulated states, places like California, New York, or Florida, without that prior approval, you are opening the organization up to fines.

SPEAKER_01: 5:26

Not to mention cease and desist orders.

SPEAKER_00: 5:28

Exactly. Cease and desist orders and severe reputational damage.

SPEAKER_01: 5:32

So this before rule effectively alters the timeline of your entire organization. You just can’t be spontaneous anymore.

SPEAKER_00: 5:38

No, you really can’t. Growth has to become highly deliberate. You have to move away from casting a wide net to strategic targeting.

SPEAKER_01: 5:45

Aaron Powell, which means leadership actually has to sit down and do the math.

SPEAKER_00: 5:48

Yes.

SPEAKER_01: 5:48

Like, is it actually worth registering in all 41 states that require it? And if we do register in all thumb, do we even have the administrative staff to handle 41 renewals next year?

SPEAKER_00: 5:57

That is a massive operational shift. You are moving from let’s go viral to let’s go viral in the jurisdictions where we are legally compliant.

SPEAKER_01: 6:06

Which is a significantly less catchy slogan.

SPEAKER_00: 6:09

Very much so. But this leads us to what the research calls the friction point. This is where the rubber meets the road, or maybe where the car hits a massive pothole.

SPEAKER_01: 6:19

We are talking about campaign timing and deadlines.

SPEAKER_00: 6:21

Yes. This is where the internal frustration really peaks. You have an ambitious fundraising goal that violently clashes with bureaucratic reality. And the biggest obstacle here is the registration approval period.

SPEAKER_01: 6:34

Aaron Powell So walk me through this scenario. Let’s say I want to run a massive Giving Tuesday campaign. It’s in late November. When do I actually need to be worrying about my state registrations?

SPEAKER_00: 6:44

Well, if you start worrying about it in November, you are already way too late.

SPEAKER_01: 6:48

Too late. For a late November launch.

SPEAKER_00: 6:49

Over certain states, absolutely. Take New York or New Jersey, for example. These are not instant online approvals like Colorado, where you just pay a fee and get a license in 20 minutes. These are manual human reviews. During peak times, like the end of the year when everyone is trying to fundraise, those backlogs can stretch to weeks or even months.

SPEAKER_01: 7:08

Oh wow. So if I apply on November 1st, just hoping to catch that Giving Tuesday wave.

SPEAKER_00: 7:14

You might still be sitting in the pending queue when Giving Tuesday comes and goes.

SPEAKER_01: 7:17

Yeah.

SPEAKER_00: 7:18

And strictly speaking, you cannot legally solicit in that state while your application is pending.

SPEAKER_01: 7:24

That creates a complete revenue blackout for that specific geography. Oh yes. That is terrifying for a budget. You are basically grounded in that state.

SPEAKER_00: 7:33

And it gets worse if your internal systems aren’t organized. Think about your annual renewals. Every state expires at a totally different time.

SPEAKER_01: 7:41

It’s not just a single deadline.

SPEAKER_00: 7:43

No. Some are based on your fiscal year end, some are just arbitrary anniversary dates. If you let a license lapse because your team was too busy planning the big winter gala, you are technically grounded again.

SPEAKER_01: 7:54

I can easily see how this happens. You are sprinting toward the end of the year, everyone is completely exhausted, and someone misses a generic email from the state of Illinois saying your renewal is due.

SPEAKER_00: 8:04

And suddenly you cannot ask your Chicago donors for money during your biggest push of the entire year.

SPEAKER_01: 8:10

There is another point in the research about financial statements holding this whole process up. This feels like a classic chicken in the egg problem.

SPEAKER_00: 8:18

It really is. Yeah. Most state renewals require your latest financial reports. That means your IRS Form 990 and potentially an audited financial statement. Right. Let’s say your fiscal year ends in December. You might not have your audit finalized until June.

SPEAKER_01: 8:33

But some of those state renewals are due in May.

SPEAKER_00: 8:36

Exactly. So you have a gap, you have to file extensions, you have to manage the calendar perfectly.

SPEAKER_01: 8:41

So if the finance team is running behind on the audit for whatever reason, the compliance team can’t file the state renewals. Yep. And then the development team cannot legally launch their summer campaign. The fundraising calendar is effectively handcuffed to the accounting calendar.

SPEAKER_00: 8:56

Aaron Powell, handcuffed is a great way to put it. You can no longer just pick a fun marketing date. You have to pick a compliance ready date.

SPEAKER_01: 9:03

And that brings us to the financial reality of all this: the cost of growth. Because we aren’t just talking about a$50 state filing fee anymore. We are talking about the success tax.

SPEAKER_00: 9:14

The success tax.

SPEAKER_01: 9:15

Yes.

SPEAKER_00: 9:15

This is the stark financial reality of scale.

SPEAKER_01: 9:18

Aaron Powell, this is all about the audit thresholds, right?

SPEAKER_00: 9:20

Correct. When you are small, you might just pay for a compilation or a basic review of your finances by a CPA. It is relatively cheap, maybe a couple thousand dollars. Sure. But as you raise more money, states demand a much higher level of assurance.

SPEAKER_01: 9:35

Aaron Powell What kind of numbers are we looking at for those triggers?

SPEAKER_00: 9:38

Aaron Powell It varies by state, naturally. But the most common triggers are$500,000 and$1 million in annual contributions.

SPEAKER_01: 9:45

Okay.

SPEAKER_00: 9:46

Once you cross those specific lines, states like California, New York, and several others legally require a full independent JAP audit.

SPEAKER_01: 9:53

Aaron Powell And an independent audit is not cheap.

SPEAKER_00: 9:55

Aaron Powell Not at all. You are moving from a$2,000 annual expense to a$15,000 or$20,000 formal engagement, plus all the internal staff time required just to prepare the documents for the auditors.

SPEAKER_01: 10:07

That is a massive jump. I can just imagine a development director popping champagne, saying, guys, we hit$550,000 this year. We broke the record. Right. And the finance director is just sitting in the corner sweating because they know that extra$50,000 just triggered a regulatory requirement that is going to cost$20,000 to satisfy.

SPEAKER_00: 10:27

Exactly. And if you didn’t budget for that, if you didn’t actively strategize for that success tax, you are in serious trouble. You literally have to spend money to prove you manage the money correctly, just so you can be allowed to keep asking for money.

SPEAKER_01: 10:43

It feels incredibly bureaucratic. But the sources do argue there is a silver lining here. It’s not just about blindly checking boxes, it’s about utilizing transparency as a strategy.

SPEAKER_00: 10:54

It is. You really have to reframe it. Financial transparency becomes a product you are selling to your donors.

SPEAKER_01: 10:59

How so?

SPEAKER_00: 11:00

Well, when you reach this level of growth, you aren’t just hiding your shoebox of receipts anymore. You are showing your pristine books to the world to prove you are a stable, mature organization.

SPEAKER_01: 11:10

And this pivots perfectly to the trust factor. Because at this stage of the game, you aren’t just asking your aunt for 20 bucks. You are asking a major foundation for a$50,000 grant.

SPEAKER_00: 11:23

Right.

SPEAKER_01: 11:23

And they do their homework.

SPEAKER_00: 11:25

They absolutely do. Large institutional donors, big foundations, corporate grantmakers, they have their own internal compliance officers. Before they ever cut a check, they run a thorough background check on your nonprofit’s posture.

SPEAKER_01: 11:38

So they are Googling you.

SPEAKER_00: 11:39

They are doing way more than just Googling. They’re pulling up the Attorney General’s charity registry in their state. They are checking to see if your organization is listed in good standing.

SPEAKER_01: 11:48

So if I miss that renewal in Illinois that we talked about earlier.

SPEAKER_00: 11:51

And your status publicly shows up as delinquent or withdrawn, that can be an automatic disqualification for a six-figure grant. Just like that. I have seen it happen. A nonprofit does all the hard work. They write a beautiful, compelling grant proposal. They have amazing impact data, but they get flat out rejected purely because they weren’t legally compliant in the funder’s home state.

SPEAKER_01: 12:13

Wow. So compliance at this level isn’t just about avoiding a minor fine. It is about being eligible to even play the game.

SPEAKER_00: 12:20

Precisely. It validates the organization to big donors, it tells that foundation, we are professionals. We are not some fly by night operation. We actually have the administrative infrastructure to handle your money safely.

SPEAKER_01: 12:34

So if you are fighting compliance or just ignoring it because it’s tedious, you are basically sabotaging your own credibility.

SPEAKER_00: 12:40

You are building a glass ceiling for your own fundraising strategy. You can only grow so high before your lack of compliance completely stops you.

SPEAKER_01: 12:49

Okay, so we know it’s important. We know we absolutely need it to scale. But let’s get real about the internal politics for a second. The notes describe this as a development versus finance tug of war. Oh, yes. And having worked in nonprofits, I know this exact vibe. It is the classic clash of departments.

SPEAKER_00: 13:05

It is the ultimate silo problem. And it is not just about clashing personalities, it is about fundamentally opposed incentives. Think about it. What is the development team incentivized to do?

SPEAKER_01: 13:16

Urgency, emotion, opportunity. Launch right now, ask questions later.

SPEAKER_00: 13:21

Right. And what about finance? They’re incentivized for accuracy, risk mitigation, and strict regulation. Stop, check, verify.

SPEAKER_01: 13:29

So development is slamming on the gas pedal, and finance is slamming on the brakes.

SPEAKER_00: 13:34

And when you put those two teams in a room without a shared overarching strategy, you get incredible friction. You get that Friday afternoon panic.

SPEAKER_01: 13:43

Right.

SPEAKER_00: 13:43

Development drops a massive new campaign on finance’s desk for a Monday morning launch. Finance looks at the target states and realizes, wait, we aren’t registered in half of these places.

SPEAKER_01: 13:53

And then finance is forced to be the Department of No.

SPEAKER_00: 13:57

Which they hate doing. Nobody wants to be the internal killjoy. But they have to protect the organization from legal risk. This leads to this awful lingering uncertainty where everyone is sitting around asking, are we actually allowed to send this email?

SPEAKER_01: 14:11

And that kind of doubt just kills the creative energy of a fundraising team.

SPEAKER_00: 14:15

It absolutely does.

SPEAKER_01: 14:16

It sounds highly dysfunctional, but you made a note here in the research that I found really surprising. You said these painful growing pains are actually a good sign.

SPEAKER_00: 14:24

They are a very good sign. Look, if you weren’t growing, you wouldn’t be having these problems in the first place. That’s true. If you were still just raising$20,000 a year from your neighbors, you wouldn’t need a gap audit. You wouldn’t need 41 state registrations. The fact that your teams are fighting about this means you are succeeding.

SPEAKER_01: 14:41

So it’s not gross mismanagement, it’s organizational puberty.

SPEAKER_00: 14:45

That is a brilliant analogy. You’re getting bigger, and the old clothes just don’t fit anymore. You cannot run a multimillion dollar organization using Wild West operations. The friction is just the signal that it is time to mature.

SPEAKER_01: 15:00

Okay, so how do we actually grow up? How do we get these two teams, the gas pedal and the brake pedal, to actually drive the car together?

SPEAKER_00: 15:08

The solution is actively integrating compliance into your strategic planning. And I know integrated planning sounds like the most boring corporate buzzword in the world.

SPEAKER_01: 15:16

It really does.

SPEAKER_00: 15:17

But it is completely revolutionary for these teams.

SPEAKER_01: 15:20

Give me the practical version of that. What does that actual meeting look like?

SPEAKER_00: 15:24

It means the compliance or finance person is invited to the strategy meeting in January, not just the frantic cleanup meeting in December.

SPEAKER_01: 15:31

So you involve them before the campaign is even designed?

SPEAKER_00: 15:35

Yes. You review the fundraising geography early on. Development says, we really want to break into the Pacific Northwest this year. Okay. Finance looks at the map and says, okay, great. We aren’t registered in Washington or Oregon yet. It will take us roughly six weeks to get those licenses approved. So let’s put that administrative work on the calendar for quarter one so you can safely launch the campaign in quarter two.

SPEAKER_01: 15:58

That immediately turns a departmental fight into a workable timeline.

SPEAKER_00: 16:02

Exactly. It aligns the calendars and it also prevents massive staff burnout. How so? Well, if you know a major state renewal or that big scary audit is due in November, maybe don’t plan your biggest, most highly complex campaign launch for that exact same week, if you only have a small support staff.

SPEAKER_01: 16:19

It seems so obvious when we say it out loud, but in the heat of the moment, people completely forget that the staff who processes the incoming donations is very often the exact same staff that processes the state regulatory filings.

SPEAKER_00: 16:32

And they can only do one thing at a time. This is why conducting periodic compliance assessments, just stopping the machine to look at the map, saves so much heartache.

SPEAKER_01: 16:42

And this brings us right back to the core theme we saw in the sources. Compliance tends to expand alongside fundraising growth, and organizations that review requirements periodically avoid most problems.

SPEAKER_00: 16:53

Exactly. If you acknowledge that growth means more rules and you just review it periodically, you avoid the crash.

SPEAKER_01: 17:00

But if you just treat compliance as a static checklist, like, oh, we did that registration three years ago, we’re good forever, you will inevitably hit a wall.

SPEAKER_00: 17:07

You absolutely will. But if you treat it as a living, breathing part of your growth strategy, it scales with you.

SPEAKER_01: 17:14

It really is a massive mindset shift. It is moving from compliance as a restriction to compliance as infrastructure.

SPEAKER_00: 17:20

That is the ultimate key takeaway here. I always like to think of it this way: you cannot build a skyscraper on a foundation meant for a garden shed.

SPEAKER_01: 17:32

I really love that visual.

SPEAKER_00: 17:33

Right. When you were a startup, you built a shed. It was great, it served its purpose perfectly for that phase. But now you are building a skyscraper.

SPEAKER_01: 17:41

So you need deep pilings, you need steel.

SPEAKER_00: 17:44

You need compliance. It is not sexy, it is not fun, but it is exactly what keeps the entire building from falling over when the regulatory wind blows.

SPEAKER_01: 17:53

And it essentially validates the hard work of the fundraising team. It ensures that the money they work so incredibly hard to raise actually stays with the mission rather than going to pay state fines or legal fees.

SPEAKER_00: 18:04

Exactly. It protects the bag.

SPEAKER_01: 18:05

It protects the bag. We definitely need t-shirts that say that.

SPEAKER_00: 18:08

We might need to get legal approval for that t-shirt first.

SPEAKER_01: 18:10

Very fair point. Well, before we wrap up, the research left us with one final, slightly provocative thought to sort of mull over. We’ve talked about compliance as infrastructure, but what if you took it a step further? What if you viewed your flawless compliance record not just as a defensive shield, but as your biggest competitive advantage when pitching to major institutional donors?

SPEAKER_00: 18:33

Oh, I like that. Using your good standing as a core part of your actual marketing strategy, showing them you are the safest bet in the sector, it completely flips the narrative.

SPEAKER_01: 18:44

It really does. It changes the whole perspective on the paperwork. Well, we have covered the entire journey today, from the Wild West to the skyscrapers. It is a lot to take in, especially for those listeners who are stuck right in that messy middle phase.

SPEAKER_00: 18:56

It is a tough phase.

SPEAKER_01: 18:57

But I think for anyone listening right now who feels that friction between their teams, it is really good to know they aren’t alone and that it is actually a sign they are on the right path.

SPEAKER_00: 19:06

Absolutely. Growth is inherently hard, but planned growth is sustainable. And that is exactly what we want for everyone listening today.

SPEAKER_01: 19:14

If you found this discussion helpful, you can find additional compliance guides and visual resources at ironwoodregistrations.com. Thanks for listening.