Email, Social Media, and When Outreach Becomes Solicitation

SPEAKER_00 (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_01 (0:14): It’s great to be here for another deep dive.

SPEAKER_00 (0:16): Yeah, let’s get right into it today because there is this very specific anxiety. I think pretty much every Executive Director or Development Director out there feels it, even if they never bring it up at the weekly staff meetings.

SPEAKER_01 (0:30): Oh, I know exactly what you’re trying to do.

SPEAKER_00 (0:31): Right. You’re sitting there at your desk, you’ve just drafted an email to your list, and it’s heartfelt. It’s urgent. It’s got a great picture of your team actually out on the ground doing the work. And right there at the bottom, there is a link. Maybe it just says “Help Us,” or maybe even just “Learn More.” You hit send. And then at like 2:00 a.m., you jolt awake wondering, “Wait, did I just accidentally break the law in 20 different states?”

SPEAKER_01 (0:56): Yes. That is the classic 2:00 a.m. panic. And frankly—and people aren’t going to want to hear this—it is not entirely unfounded. It’s the truth.

SPEAKER_00 (1:08): But I guess that is exactly the tension we are dealing with today. We’re looking at that line between, you know, just communication and official solicitation. 10 years ago, that line was basically a brick wall.

SPEAKER_01 (1:20): Very clear.

SPEAKER_00 (1:21): Very clear. But today, with digital outreach, it’s just a blur. A friendly update on Instagram or a quick e-newsletter can actually trigger these intense regulatory requirements. And most leaders don’t even know those rules exist until they get a scary letter from an Attorney General.

SPEAKER_01 (1:40): Exactly. And our mission for this deep dive is to dissect that blur. We aren’t talking about the obvious stuff today. I mean, if you mail a formal printed invitation to a gala…

SPEAKER_00 (1:51): Everyone knows that’s a solicitation.

SPEAKER_01 (1:53): Right. You know it, the state knows it. We’re looking at the gray areas today: the e-newsletters, the viral social media posts, those donate buttons sitting on your homepage. We really need to unpack how regulators view digital outreach versus how we tend to view it as marketers. Often those two views are diametrically opposed.

SPEAKER_01 (2:11): Completely opposite.

SPEAKER_00 (2:12): And for everyone listening, whether you’re on the finance side trying to keep the organization safe, or you’re in marketing just trying to keep the lights on—this deep dive is about giving you the confidence to press “send” without constantly looking over your shoulder.

SPEAKER_01 (2:25): Because confidence comes from clarity. If you actually know where the lines are drawn, you can walk right up to them without accidentally stepping over.

SPEAKER_00 (2:35): So to understand the mess we’re in now, I feel like we have to look briefly at where we came from. Legally speaking, the old “direct mail” days were clear, right?

SPEAKER_01 (2:52): It was incredibly clear. Historically, a solicitation was defined by physical presence or direct contact. You sent a physical letter to a specific address. You knew that Mrs. Smith lived in Ohio; therefore, you were soliciting in Ohio. It was a tangible physical transaction of information.

SPEAKER_00 (3:09): Or like the classic rubber chicken dinner. If I rent a hall and hold a gala in Chicago, I am soliciting in Illinois. It’s distinct. It’s contained.

SPEAKER_01 (3:18): Precisely. You had jurisdictional certainty. But then the internet happened, and we entered what we in the field call the Digital Blur.

SPEAKER_00 (3:31): And this is where it gets so messy because a digital message does everything at once. I can send an email that shares a touching success story, educates the donor on a policy issue, and asks for five bucks, all in the exact same paragraph.

SPEAKER_01 (3:45): And that creates a massive compliance paradox. That email feels informal to you—like you were just chatting with your community—but to a regulator, if that email lands in an inbox in Florida and it asks for money, you have physically entered Florida to solicit funds.

SPEAKER_00 (4:04): Wait, hold on. “Physically entered”? I’m just sitting at my laptop in Oregon.

SPEAKER_01 (4:10): It definitely feels like a stretch to us, but legally, that is the framework they operate under. When you send a targeted message into a state with the intent to receive funds, you are subject to that state’s jurisdiction.

SPEAKER_00 (4:24): Okay, but that sounds literally impossible to police. How on earth do regulators actually define solicitation in this context? Is it just looking for the exact phrase “please donate”?

SPEAKER_01 (4:44): No. Regulators look at the overall context. They are looking for the intent of the message. Most states look to a framework called the Charleston Principles.

SPEAKER_00 (5:06): The Charleston Principles. What do they actually say in plain English?

SPEAKER_01 (5:21): They basically distinguish between where you are domiciled (physical office) and where you have substantial non-incidental contact. Essentially, just having a website isn’t enough to trigger registration everywhere. But if you use that website to specifically target people in a state, or if you receive substantial repeated contributions from a state and then follow up with those people, then you’re on the hook. The activity moves from passive to active.

SPEAKER_00 (5:53): Let’s use a test subject: “Community Table,” a food bank in Kansas City. They send a monthly newsletter. At the bottom, there’s a link that says “Support Our Mission.” That email hits the inbox of a donor who moved to New York. Is Community Table now soliciting in New York?

SPEAKER_01 (6:32): This brings up what we call the Two-Click Rule in compliance—more of a rule of thumb. If the email says, “We need $50 to buy a new tire, please click here to give,” that is a direct solicitation. You are soliciting in New York, period.

SPEAKER_00 (6:53): Okay. But what if the email just links to a blog post about the truck, and on that blog post, there’s a sidebar with a donate button?

SPEAKER_01 (7:02): That is the gray area. Generally, if the email is purely informational—”Read about our truck”—and it links to an informational page, the fact that a donate button exists on the global template might be seen as passive. You aren’t driving them to the donation; you are driving them to the story.

SPEAKER_00 (7:20): But regulators aren’t stupid.

SPEAKER_01 (7:25): Correct. If you internally track click-throughs and financial conversions on that specific email, you are treating it as a fundraising campaign, and the regulator will, too. Intent matters. If you are engineering the user journey to extract a donation, that is solicitation.

SPEAKER_00 (8:09): So do safe harbors actually exist?

SPEAKER_01 (8:16): Yes. Purely administrative or educational updates are fine—impact reports, changes to hours, or research articles. If there is no “ask” and no direct link to a donation form in the body, you are generally in the clear. But the very moment you add a little line at the bottom saying, “And if you want to help, click here”… you have crossed the line.

SPEAKER_00 (8:49): Okay, let’s pivot to social media. Community Table posts a video on TikTok. Paul Rudd shares it. Suddenly, they have 50,000 views and donations pouring in from everywhere. Did they accidentally break the law?

SPEAKER_01 (9:26): Initially, that post was likely passive. They didn’t target California. But once the money starts coming in, the “non-incidental” part kicks in. If Community Table accepts those donations and then sends a follow-up email saying, “Thank you, please consider giving again,” they have officially established a solicitation relationship in those states.

SPEAKER_00 (10:10): So the initial viral explosion might be forgivable, but the follow-up is what traps you. What about “Start your own fundraiser” buttons?

SPEAKER_01 (10:52): If you have a button on your own website that says “Start your own fundraiser for us,” you are explicitly authorizing it. You are responsible for where those individuals solicit.

SPEAKER_00 (11:02): I’ve heard leaders say if I put a donate button on my website, I have to register in all 41 states. Is that true?

SPEAKER_01 (11:16): Generally, no. It comes back to passive availability versus active promotion. If I organically find your website through a Google search from Texas, that’s passive. But if Community Table buys a targeted Facebook ad set to “Texas residents,” that is highly active promotion. You paid money to digitally enter Texas. You are soliciting.

SPEAKER_00 (12:18): Let’s play mythbusters. Myth #1: “We are too small. California doesn’t care about my $50k nonprofit.”

SPEAKER_01 (12:43): That is a dangerous gamble. While some states have threshold caps (e.g., under $25k might be exempt from formal registration), you are not exempt from the law itself. Smaller organizations are often reported by disgruntled former board members or unhappy donors.

SPEAKER_00 (13:15): Myth #2: “The platform (GoFundMe, etc.) handles the legal stuff.”

SPEAKER_01 (13:30): Almost always no. The platform is a payment processor. You are the solicitor. You cannot outsource your legal liability to a tech platform.

SPEAKER_00 (14:09): Myth #3: “It’s just an informal Instagram story.”

SPEAKER_01 (14:16): The law does not care about the medium; it cares about the message. A request for money in a casual TikTok dance is a solicitation just as much as a 100-page grant proposal.

SPEAKER_00 (14:34): So what are the practical steps? What does the Executive Director do tomorrow morning?

SPEAKER_01 (14:52): Break down the silos between marketing and finance. You need a coordination meeting. Before the end-of-year campaign, compliance needs to ask, “Who exactly is getting this email? Are we segmenting our list?” If you aren’t registered in Florida, just suppress Florida zip codes from that specific appeal.

SPEAKER_00 (15:48): But that requires knowing where your donors are located.

SPEAKER_01 (15:52): Step two: Data Review. Pull a report. Look at donors by state. If you suddenly have 500 active donors in a state where you aren’t registered, you either stop asking them for money or you go get registered.

SPEAKER_00 (16:12): I like the mindset shift you mentioned—that compliance is a symptom of success.

SPEAKER_01 (16:34): Exactly! If you’re worrying about New York and California, it means your mission is resonating far beyond Kansas City. It’s a growing pain. Reframe compliance as scaling sustainably. Doing this work up front gives you the freedom to grow fearlessly.

SPEAKER_00 (17:50): We’ve covered a lot: the shift from physical galas to digital blur, the Charleston Principles, and the difference between passive and active outreach.

SPEAKER_01 (18:28): Intentionality is the word of the day. Don’t let an algorithm decide your compliance footprint for you. You need to decide it.

SPEAKER_00 (18:37): And your final thought?

SPEAKER_01 (18:43): We obsess over click-through rates, but have you mapped the geographic footprint of those clicks? Your Google Analytics and email data tell you exactly where your audience is located. Your digital dashboard isn’t just a marketing tool—it’s a compliance map.

SPEAKER_00 (19:29): The map is already there; you just have to look at it. If you found this discussion helpful, you can find additional compliance guides and visual resources at ironwoodregistrations.com. Thanks for listening.