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143: Anonymized Juicy Gossip | What Happens If You Don't Do the Nonprofit Filings?

Charity Therapy

Release Date: 07/24/2025

162: No, Not the Tomatoes! | Are Nonprofit Startup Costs Tax-Deductible Donations for the Founder? show art 162: No, Not the Tomatoes! | Are Nonprofit Startup Costs Tax-Deductible Donations for the Founder?

Charity Therapy

You scraped together your own money to start a brand-new nonprofit. You’re out the money, but can you at least take a tax deduction? Meghan and I are back with a question from a new nonprofit founder who wants to know if the startup cash they put in before getting their 501c3 status counts as a tax-deductible donation. It's one of the most common questions we hear from new founders, and the answer involves a pretty handy IRS rule most people don't know about. Real Listener Question: “In June 2025, two friends and I created a housing placement nonprofit and each put our own money in to get...

info_outline 161: A Rinky-Dink Outfit | Why Recording In-Kind Donations Matters For Your Nonprofit show art 161: A Rinky-Dink Outfit | Why Recording In-Kind Donations Matters For Your Nonprofit

Charity Therapy

Your nonprofit is doing real work, but do your financials show it? In this episode, Meghan and I tackle a listener question from a small nonprofit that's running into a big problem: their numbers don't match their story. The for-profit company supporting them pays for nearly everything, but none of that shows up on the books, and funders are raising eyebrows. Real Listener Question: “Our employees, office space, and equipment are all paid for by a for-profit company and donated to our nonprofit. Our financials make it look like we're barely doing anything. I've been tasked with finding major...

info_outline 160: Indiana vs Minnesota Throwdown | Can Business Interruption Insurance Help Nonprofits Who Closed During ICE Raids? With Cody Wiswasser show art 160: Indiana vs Minnesota Throwdown | Can Business Interruption Insurance Help Nonprofits Who Closed During ICE Raids? With Cody Wiswasser

Charity Therapy

Your nonprofit closed its doors because of ICE enforcement or federal funding cuts. Is there an insurance policy that could actually help? Maybe, but the answer is a lot more complicated than you'd hope. In this episode, I'm joined by Cody Wiswasser, an insurance professional at , to dig into my questions. With so much uncertainty hitting nonprofits right now, I needed to know whether business interruption insurance is something my clients should actually be thinking about. Here’s the situation: Can nonprofits get business interruption insurance? Are closures for ICE raids or funding cuts...

info_outline 159: Reporter on the Street | Can You Use Retirement Funds to 159: Reporter on the Street | Can You Use Retirement Funds to "Invest" In A Nonprofit? With Jeff Beck

Charity Therapy

Do you know someone eyeing their retirement accounts to fund their nonprofit dreams? We need to talk! In this episode, I'm joined by , a wealth advisor at , to tackle a listener question that had me equal parts fascinated and horrified. Real Listener Question: “My partner has a traditional IRA with about $100,000 in it. Can she invest that money in my 501(c)(3) without penalties? Do we need to set up a for-profit company for her IRA to invest in first? Are there IRS rules against her investing in something I founded and run?” Jeff and I dig into the mechanics of IRAs, self-directed...

info_outline 158: Is Your Ringer On? | How Nonprofits Can Find and Hire a Good Lawyer show art 158: Is Your Ringer On? | How Nonprofits Can Find and Hire a Good Lawyer

Charity Therapy

Finding a lawyer should not feel harder than solving the legal problem itself. And yet, here we are. In this episode, Meghan and I talk about something that comes up constantly in my nonprofit law practice: how nonprofit leaders and boards actually find a good lawyer and how to tell whether someone is the right fit. Real Listener Question: “I am a board member tasked with finding my small nonprofit a lawyer. I am trying to collect five options for the board to review and have the board interview each lawyer. I’ve prepared an RFP to get information from as many firms as possible. Is there...

info_outline 157: Old Woman Shakes Fist at Sky | How Classy May Be Hurting Your Donor Relationships show art 157: Old Woman Shakes Fist at Sky | How Classy May Be Hurting Your Donor Relationships

Charity Therapy

Nonprofit newsflash - your donation platform might be quietly annoying your biggest donors 😬 In this episode, Meghan and I dig into some nonprofit LinkedIn drama sparked by a from the one and only . Here’s the situation: You gave a big donation, and you received an auto-generated donation receipt from the org’s donation platform. The problem?  The gift acknowledgement letter and receipt are WRONG.   We break down why donor acknowledgement letters matter so much, what the IRS actually requires in those receipts for gifts over $250, and how automated systems can unintentionally...

info_outline 156: Captain Depressio Reporting for Duty | Can Nonprofits Give Tax-Free Money to People? show art 156: Captain Depressio Reporting for Duty | Can Nonprofits Give Tax-Free Money to People?

Charity Therapy

Nonprofits are tax-exempt, so lots of people assume that nonprofits don’t have to worry about taxes ever. Right???? Well, not quite 😐 In this episode, Meghan and I dig into a question I hear all the time from people who want to help their communities but are confused about how nonprofit tax rules actually work. Real Listener Question: “I own a couple of restaurants and we have several events to raise money for certain causes. Usually the money goes toward a charity or a local group, but sometimes we'll do it for a community member who needs financial support. The problem we're seeing is...

info_outline 155: Baby Don’t Hurt Me | What To Do When a Donor Gift Harms More Than Helps show art 155: Baby Don’t Hurt Me | What To Do When a Donor Gift Harms More Than Helps

Charity Therapy

You’re getting donations for a nonprofit – and that’s great! But sometimes generosity comes with strings you never expected. In this episode, Meghan and I dig into the wild world of donor gifts and why nonprofits need clear guardrails to protect themselves from gifts that actually hurt the nonprofit. Real Listener Question: “We have a donation button on our website where people can give online and set up recurring donations for monthly contributions. A few weeks ago, someone set up a daily 50 cent donation. Our accountant looked into it and is saying that it's not fraud or anything...

info_outline 154: It's Gravy, Baby! | What is a Nonprofit Audit? with Hannah Hugen show art 154: It's Gravy, Baby! | What is a Nonprofit Audit? with Hannah Hugen

Charity Therapy

Think an audit is something to fear for your nonprofit? I get it! But what if it’s actually a powerful tool for growth? In this episode, I sit down with nonprofit auditor Hannah Hugen from to unpack what an audit really is and why it’s not nearly as scary as it sounds. Real Listener Question: “We filed the 1023-EZ and said we’d stay under $50K… but now a funding opportunity would push us past that. Will the IRS audit us? Should we say no to the money?” Hannah and I dig into what an audit actually involves, what the IRS does (and doesn’t) care about, and how nonprofits can...

info_outline 153: It's a Triple Whammy | How to Fix the Culture of Overwork at Your Nonprofit with Rachel Platt show art 153: It's a Triple Whammy | How to Fix the Culture of Overwork at Your Nonprofit with Rachel Platt

Charity Therapy

If your team is exhausted, overwhelmed, and constantly working nights and weekends, you might be dealing with more than a scheduling issue. You might be dealing with a culture problem that is hurting your mission. In this episode, I invited my friend and people strategy expert to talk with me about the hidden issues inside nonprofit overwork and what it really takes to build a sustainable organizational culture. Real Listener Question: I’m a new staff member, and everyone at this nonprofit works tons of overtime without being paid (as hourly employees). The ED works all the time, and the...

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More Episodes

What would you do if you inherited a nonprofit… with 20 years of missing paperwork?

It’s Jess Birken here, and I’m back with my co-host Meghan to dig into one of the messiest listener questions yet. A nonprofit has been operating off the radar for decades, and it's time to figure out what happens next.

Real Listener Question: "I just took on the treasurer role for a family nonprofit, but nothing’s been filed since 2005. The bank account is still under the name of a deceased board member. I’m wondering if I should just start over with a new nonprofit. Is that even possible?"

This kind of thing happens more often than you’d expect. A well-meaning person takes on a board role and discovers the organization hasn't filed anything in decades. In this episode, Meghan and I unpack what to do when you find yourself in a nonprofit compliance nightmare. We cover how to figure out what kind of legal entity you’re actually dealing with, how to protect yourself, and how to decide whether to clean up the mess or start fresh. If you're the one caught holding the bag for a nonprofit with a messy past, this one's for you.

 

What You'll Learn:

  • Why nonprofit compliance is more complicated than for-profit businesses
  • How to tell if your organization is really a 501(c)(3)
  • What happens when a nonprofit operates without filing for years
  • When it makes more sense to start a new organization than try to fix the old one
  • Why board training is essential, even for small nonprofits
  • What every board member should ask before agreeing to join
  • How to stop stressing about the past and start moving forward

 

Bottom line: If you inherit a messy nonprofit past, you are not alone. You can’t fix everything that came before you, but you can take charge today and make sure the future is solid.

 

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