The Dark Side of Entrepreneurship: Difficult Clients & Refunds
This one's a little different. What you're about to hear is a recording straight from our Weird Hermits Roundtable — a mastermind group discussion where we got real about the stuff nobody likes to talk about publicly.
Difficult clients. Refund requests. Payment plans that ghost you. Employees who snap. Customers who buy domain names to smear you. Yes, that actually happened.
The conversation goes deep on what everyone's refund policies actually look like, the boundaries we've set after getting burned, and the mindset shifts that helped us stop letting this stuff live rent-free in our heads.
- The wildest client situations from a room full of multi-year entrepreneurs (Jordan's story alone is worth the listen)
- Early warning signs that a client might be trouble — and the one pattern that keeps coming up
- How to build refund policies that protect your business AND feel right to you
- Why having a written policy is actually the kindest thing you can do (for everyone)
- What to do when payment plans ghost you — and the mindset shift that makes it manageable
- How to regulate yourself when ad comments or nasty emails make you want to lose it
- The "What Would Destini Do?" framework for navigating messy business moments with boundaries and grace
- What Would Destini Do? Claude Skill — Paste one prompt, describe your messy situation, and get walked through exactly how to handle it: lab.destinicopp.com/what-would-destini-do
Nobody warns you about this part.
Not the client who files a PayPal dispute mid-VIP day because she didn't think you were going to finish on time. Not the customer who buys the domain systemsscammedme.com to build a webinar about you. Not the employee who quits to your ops manager instead of to you — and threatens to burn your business down on the way out.
This is the stuff that happens in the DMs of your mastermind, not on the highlight reel. And because we don't talk about it enough, a lot of founders think they're the only ones it's happening to — or worse, that it means something is wrong with them or their business.
It doesn't.
I recently sat down with five other founders from our mastermind group — what we affectionately call the Weird Hermits — for a roundtable on exactly this stuff. Difficult clients. Refund requests. Payment plans that go dark. The mindset it takes to stop letting it all live rent-free in your head. Here's what came out of that conversation.
The Situations Nobody Posts About
One of the things that struck me most about our roundtable was how casually these stories came out. Like we'd all been sitting on them for years, quietly processing, and suddenly here was a room where it was safe to just say it.
Jordan Gill of System Save Me shared what might be the wildest story I've ever heard in online business. A VIP day client who grew increasingly hostile during the call, filed a PayPal dispute when Jordan suggested rescheduling, then — after losing the dispute — threatened to create an entire webinar called "Celebrity Scammers" featuring Jordan's face, and actually purchased the domain name to back it up. All of this while Jordan was about to launch her signature program, during a pandemic, in what Jordan describes as a client who "went down the crazy."
"I imagine she spent at least three hours buying the domain and building those slides. We had three hours left on the VIP day. She could have used that time to actually get the work done."
— Jordan Gill, System Save MeThe webinar never happened. The domain went unused. And Jordan has had a thriving business for six years since.
Kate Kordsmeier of Success with Soul described an employee who quit without warning, threatened to expose her as a fraud to her industry, and called her names — all while living across the street. It was, as Kate put it, the hardest thing she'd ever gone through in business. Not because of anything the employee could actually prove, but because it was a real relationship that shattered overnight.
Kate also shared something even more recent: discovering that the person who bought her business in 2021 had been quietly stealing from her — ultimately over $25,000 — for years. And that after speaking to three different lawyers, she made the deliberate choice to walk away rather than spend her energy chasing it.
Liz Stapleton stumbled onto a 600-word article that had been written about her membership refund policy — written over a year prior by a member who was upset that Liz upheld her no-refund-on-renewals terms. The article clearly laid out the situation, including the fact that the writer had agreed to the terms. Liz's reaction after the initial sting: "That's actually an amazing article. It puts the world on notice that I set boundaries and stick to them."
The One Warning Sign That Keeps Coming Up
I asked the group if they'd noticed any patterns — early signals that a client might be difficult down the road. The answer came quickly and everyone agreed: love bombing.
When someone comes in extremely hot — "I can't believe I found you, you're going to save my business, you're amazing" — pay attention. That level of intensity before the relationship has even started often signals someone with outsized expectations. And when those expectations aren't met, the energy can flip just as fast.
This doesn't mean every enthusiastic buyer is trouble. But it's worth noting when the praise feels disproportionate, the stakes feel too high, or someone seems to need you to be something more than what you've offered to be.
The Refund Policy Conversation Nobody Tells You to Have With Yourself
Here's the thing about refund policies: the actual terms matter less than whether you've thought through them consciously and committed to applying them consistently.
Our group uses wildly different approaches. Kate has landed on a seven-day no-questions-asked window after testing multiple models over a decade — and she's seen refund requests go down, not up, since implementing it, because buyers feel safer to purchase in the first place. Jordan operates on a strict no-refunds policy and requires buyers to actively check a box at checkout confirming they understand this before they can complete their purchase — which she credits with nearly eliminating disputes entirely. I run a 14-day policy for my B2C HobbyScool brand and no refunds for my B2B offers, because the audiences and purchase dynamics are genuinely different.
What everyone agreed on: case-by-case refund decisions are a trap.
"Without a policy, you end up in this place of deciding whose trauma is bad enough to deserve a refund. It's not fair to anyone — including you."
— Weird Hermits RoundtableWhen you have a written policy that buyers agree to before purchasing, you remove yourself from the emotional negotiation. Your team can handle most of it. You only step in for truly unusual situations. And you're not left wondering whether you made the right call.
Building Systems That Protect You Before Things Go Wrong
The through-line across every story in our roundtable was this: the founders who handled these situations best weren't necessarily tougher or more naturally unbothered. They had better systems.
Terms That Must Be Actively Agreed To
Don't bury your refund policy in a footer. Require a checkbox at checkout that says something like "I understand and agree that this purchase is non-refundable." The buyer can't complete the transaction without it. This one change has dramatically reduced disputes for multiple founders in our group.
A Zero-Tolerance Policy Your Team Can Enforce
You don't have to personally manage every difficult interaction. Build a clear policy — ours is zero tolerance for meanness, period — and give your team permission to act on it without escalating to you. Rude email to support? Unsubscribe and block. Nasty comment on the event page? Remove immediately. No warning required.
Automated Access Removal for Failed Payments
If someone stops paying on a payment plan, their access should be removed automatically — not after you've chased them down through three rounds of emails. Most platforms support this. Set it up once and let the system do the work. Reinstate access only when payments are complete.
A Private Blacklist for Pattern Offenders
Within your trusted network — a mastermind, a small group of peers — sharing names of people who have repeatedly acted in bad faith is a legitimate protective measure. Keep it private (data privacy laws apply to public posts). But knowing that someone has pulled the same move on three other founders you trust is genuinely useful information.
The Mindset Shift That Actually Helps
Systems get you most of the way there. But there's still a moment — when you see a dispute notification, or read a negative article about yourself, or get a threatening email — where the emotional response is real, and you have to do something with it.
A few things that came out of our roundtable that I think are genuinely useful:
Detachment comes from preparation, not personality
Kate described the mindset shift that helped her most with failed payment plans: padding her savings account until the loss of any single payment wasn't a financial crisis. When the money isn't existential, the emotional charge drops. This isn't about being rich — it's about building enough of a buffer that you're operating from stability, not scarcity.
Sometimes giving the refund IS the boundary
Faith Mariah made a point that stuck with me. Sometimes issuing a refund isn't a capitulation — it's a clean exit from a relationship that was never going to work. Closing the loop so you can move on. That reframe changes everything about how it feels to write the check.
Their behavior tells you about them, not you
Kate found out later that the employee who threatened her was in the middle of a divorce with a parent in the hospital. Jordan's client probably had things going on that had nothing to do with a VIP day. This doesn't excuse the behavior. But it does make it easier to stop internalizing it as evidence of something wrong with you or your business.
You can't please everyone, and trying is expensive
Some of the most pointed comments on my ads for a free event came from other businesses — people with something to gain from making me look bad. I had to regulate myself, respond briefly to a couple of them, close the tab, and walk away. That's not weakness. That's resource management.
Not Sure How to Handle It? Ask WWDD.
I built a free Claude skill based on exactly the kinds of difficult situations we covered in this roundtable. Paste one prompt, describe your messy situation — the refund request, the threatening email, the boundary you don't know how to enforce — and it walks you through how I'd handle it.
Get the Free Skill →The Part That Gets Easier
One of the most reassuring things about sitting in a room with founders who've been doing this for a decade or more is how matter-of-fact the stories become. Jordan told hers with the energy of someone recounting a mildly absurd anecdote. Kate talked about the $25,000 theft with hard-won clarity. Liz practically laughed about the smear article.
That's not because these things didn't hurt. They did, and do. It's because with enough time and enough policy infrastructure, these situations start to feel like weather — an unpleasant but predictable feature of running a business, not an indictment of you as a founder.
The goal isn't to never feel anything when this happens. The goal is to have a system that handles most of it before it gets to you, a policy that takes the personal decision-making out of it, and a trusted network of people who have been through it and can remind you that you're not alone.
Because you're not.
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Take the Free Scorecard →Frequently Asked Questions
Document everything and make sure your terms and conditions are airtight before the dispute is filed. If your agreement clearly outlines what was delivered and the client agreed to your terms at checkout, you have strong grounds to win. Send your evidence to the payment processor and let the process play out. Many experienced online business owners also recommend immediately blacklisting anyone who threatens a dispute — regardless of whether they follow through — to protect your business from future interactions with that person.
There's no one-size-fits-all answer, but the most important thing is that you have a written policy and you apply it consistently. Common approaches include no-refund policies (cleanest for digital products since content is delivered instantly), 7-day no-questions-asked windows (can actually increase sales because buyers feel safer), and 14-day windows for lower-cost tripwire offers. Whatever you choose, make sure buyers must actively agree to it at checkout — a required checkbox before purchase significantly reduces disputes.
Set up automated systems to remove access immediately when a payment fails — don't wait for manual follow-up. Make sure your terms clearly state that this is a fixed payment obligation, not a subscription, and that access is reinstated only when payments are complete. Send automated payment failure emails and make it easy for people to update their payment method. Most people who miss payments aren't being malicious — they simply didn't see the notification. That said, anyone who ghosts entirely after multiple attempts should be removed from your ecosystem and noted in your systems.
One of the most commonly cited red flags among experienced online business owners is love bombing — when someone comes in extremely hot with comments like "you're going to save my business" or "I can't believe I found you." Intensity that feels unusual early in the relationship often signals someone with unrealistic expectations who may become difficult if those expectations aren't met. Trust your gut when something feels off before someone even buys.
The biggest mindset shift most experienced founders point to is detachment through preparation — having clear policies, systems, and team protocols means you don't have to personally re-litigate every situation. Building a savings cushion also helps enormously: when you're not dependent on any single payment, the emotional charge drops significantly. It also helps to recognize that difficult behavior almost always says more about what that person is going through than about you or your work.
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Transcript
[00:00:00]
DR. DESTINI COPP
Hi there. Welcome back to the Creator's MBA Show. This is Dr. Destini Copp, and I'm super excited that you are joining me here today. This episode is a little different — it's a recording from one of our Weird Hermit Roundtable discussions. That's our mastermind group. And we sat down to get real about the messy side of running an online business: difficult clients, refund requests, payment plans that ghost you, employees who snap, customers who buy domain names to smear you. Yes, all of that has actually happened, and you're going to hear the story.
DR. DESTINI COPP
The conversation goes deep on refund policies, what boundaries people have set after getting burned, and the mindset shifts that helped us stop letting this stuff live rent free in our heads. And one thing that came up in this conversation — something the group actually called out by name — is "What Would Destini Do?" I put together a free Claude skill based on exactly the kind of situations I have experience with. You paste one prompt into the Claude skill, describe your messy situation — the difficult client, the refund demand, the threatening email, the boundary you don't know how to enforce — and it walks you through the same way I would handle it. To grab this, go to destinicopp.com/wwdd. Alright, let's get into it.
[00:02:00]
DR. DESTINI COPP
Welcome to our guests who are joining us. If you haven't been to one of these roundtables before, this is our mastermind. It's half of the people in our mastermind — the ones who could make it today. We call ourselves the Weird Hermits, and we just like to have these live roundtables to share different topics and our takes. I think it's always helpful to see how other people are running their businesses. So we're going to kick this off by having everyone introduce themselves. Kate, if you want to go ahead and kick us off, that'd be great.
KATE KORDSMEIER
Okay, great. Hi everybody. I'm Kate Kordsmeier. I run Success with Soul, which helps people create high-profit, low-maintenance businesses without social media.
DR. DESTINI COPP
All right, Destini?
DR. DESTINI COPP
Yeah. Hi, my name is Destini Copp and I have two brands that I manage. I have HobbyScool, where we do online learning, virtual summits, and all types of fun hobbies. And then I have my personal brand, which is my Creator's MBA brand, where I help digital product creators get that consistent, recurring revenue in their business.
LIZ STAPLETON
Fantastic. Ruth?
RUTH POUNDWHITE
Hi everyone. I am Ruth and I help people to grow and sell in their business in a way that doesn't require them to be on all the time.
LIZ STAPLETON
Awesome. Jordan?
JORDAN GILL
Hey y'all. I'm Jordan Gill, founder of Systems Saved Me. Right now what I'm doing is helping people build micro tools using AI. Most people understand it as vibe coding if you're in the tech world, but if you're not, it's basically just creating little apps that people will pay you for — apps that will help supplement your other expertise, whether it's services, courses, or whatever.
LIZ STAPLETON
Fantastic. Faith?
FAITH MARIAH
I'm Faith Mariah. You can find me at faithmariah.com. I run a mastermind for women who want to grow their business in community and start making consistent income. We do 90-day planning and basic business strategy as well as mindset.
LIZ STAPLETON
Awesome. And I'm Liz Stapleton. I run Creator Ops Hub, where I help creators build systems that run their businesses so they can scale without chaos. And then over on my other brand, elizabethstapleton.com, I use my background as an attorney to teach on the legal side of running an online business.
[00:04:00]
LIZ STAPLETON
So today's topic for our panel is difficult clients, refunds, and really the dark side of entrepreneurship — which definitely doesn't get talked about as much, even though we all experience it. While we sort out some technical things on my end, let me bring up our first question. If you guys have questions for us, please drop them in the chat. I'll be keeping an eye out for them. First question is: What's the hardest client situation you've had to navigate? Anyone want to kick us off?
JORDAN GILL
I can throw my hat in the ring. Having been in business for 10 years, I would say probably one of the hardest ones was when I was doing VIP days. I had someone who, while I was on the call, just didn't believe in the work I was doing — which is a very strange experience. At the time I was building out people's client management systems, so I'm sitting there talking with her, getting her information, building at the same time, and she just kept saying, "I don't think you're going to get it done in time" — literally throughout the entire call.
JORDAN GILL
We got about halfway through and I said, "Hey, maybe today is just not the day. I'm feeling like something's going on that I'm not privy to, which is totally okay. Let's put a pause on it and reschedule for another day when you feel more confident in the work we're doing together." So we got off the call, and then she proceeded to email me and say, "I'm filing a dispute because you didn't get everything done." And I said, "If we remember the conversation, we agreed to reschedule on a day that feels really good for you." So then she went ahead and filed a dispute anyway. I sent in the information to PayPal and I won — which says a lot, because PayPal never gives you money back.
[00:06:00]
JORDAN GILL
And then she proceeded to say she was going to create — and this was honestly before a lot of people even knew who I was — an entire webinar called "Celebrity Scammers," with my face on it, and share it in a Facebook group of 10,000 people. She actually bought domain names. She went full-on crazy. And what's even crazier is I was literally about to launch what became my signature program the very next week. And also the pandemic was happening. She tried to file another PayPal dispute, and I was like, absolutely not. She said, "If you don't pay me back, this is going live on Tuesday." And I said, "Bring it on." I just stood my ground — because I had been bullied in my younger years, so it felt like I was finally standing my ground now. And she never put it out there. She never did the webinar. None of those things. But it absolutely shook me.
[00:08:00]
JORDAN GILL
I share that story to be like — you're probably going to experience something on the lighter side of this. But also know that I've continued to have a business six years after that. I would say that's definitely in my top experiences.
KATE KORDSMEIER
Imagine if she had put all that effort into actually finishing the day she had with you.
JORDAN GILL
That's what I'm saying! I was like, we have three more hours together. You probably spent at least three hours buying the domain and putting slides together with my face — obsessing over me in this weird way. We could have wrapped this up. We could have made it positive. Apparently not.
LIZ STAPLETON
Does anyone else have a hardest situation they want to share?
KATE KORDSMEIER
Not like that. I feel like Jordan wins that one.
JORDAN GILL
This is not a competition.
[00:09:00]
JORDAN GILL
I'll say — your agreement is what saved me in all the PayPal stuff, Liz. I worked with an attorney on my VIP day agreement, and that's genuinely what saved me. My agreement was a hundred percent what saved me. So guys — have contracts, have policies, and make sure clients have to agree to them before they can buy.
KATE KORDSMEIER
So what you're saying is your next site is going to be called ContractSavedMe.com?
JORDAN GILL
We could collab on that. Me and Liz, tag team.
LIZ STAPLETON
Jordan just shared the perfect example, and as I was going through my own thought process, I remembered times when a client accused me of something or said I only care about money when I upheld a boundary about being paid for work. Or when I've run a summit and someone said, "You are deliberately trying to overwhelm neurodivergent people." That really hit me. But things like that — sometimes in the moment they feel so huge. And then it's funny to reflect on, because when you're saying "oh, what's the worst thing that happened?" I'm like, I don't even remember. That's the really interesting part, right? In the moment these things are so difficult, and we don't know how to handle what feels like an attack on our character. And then it's no big deal when you look back. Like Jordan — I'm sure you were very stressed in that situation, but it's a great story now.
RUTH POUNDWHITE
Yeah. It's all part of the journey, isn't it?
[00:11:00]
LIZ STAPLETON
I think I told you about this, Ruth — where last week I came across an article written about me, a review of "Liz Stapleton's membership." It was a 600-word article. I figured out it was from over a year ago — I just happened to stumble upon it now. They had been in the membership, had a renewal — and by the way, I have things set up so they get notified a week before the renewal goes through. I'm not trying to pull one over on anybody. But in my terms, my refund policy is seven days from the initial purchase, and it does not apply to renewals. They wanted a refund and I said no. And they said, "I'm going to file a dispute." I said, "You're welcome to, but you've already acknowledged in these emails that those were the terms you agreed to." The whole article was clearly trying to smear me. She laid it out and even said, "Look, these were the terms and I did agree to them, but just know — she makes no exceptions." Initially I was a little upset, because I could tell the intent was to make me sound bad. And the more I thought about it... I was like, that's actually an amazing article. It puts the world on notice that I set boundaries with my terms and I stick to them. But the initial emotion was not great.
LIZ STAPLETON
Does anyone else want to share a difficult situation, or do we want to move on?
[00:13:00]
KATE KORDSMEIER
Yeah, I have a long list I could share. But what I'll say is — I can echo everything that's been said. I've had plenty of refund requests. I've had plenty of people threaten to file a dispute. I've won every single dispute except one, and that one was an actual scammer who got into my site, scraped my entire course in one hour, and then filed disputes — they actually went through on three months of payment plans. But I've always won all my other disputes because of my terms and conditions and how explicitly everything is laid out.
KATE KORDSMEIER
I've had people file disputes for things that were clearly delivered exactly as promised. I've had people file a dispute without ever even reaching out to say, "Hey, I'd like a refund" or "I'm not happy with this." They just file a dispute as if it's nothing. And it's like — this has such an impact on small businesses. But the one thing I wanted to share that's different is I actually had an employee situation back in — I think it was 2021. Basically, out of the blue, she quit — to my ops manager instead of quitting to me. She lives across the street from me still today. And she threatened to burn my business to the ground. Literally, those were her exact words. She called me horrible names. She said she was going to expose me for the fraud that I am — which was based on literally nothing. I wasn't actually afraid of anything she could say, but it was the hardest thing I've ever gone through in my business, because this woman was a friend. She was a neighbor. She came to my daughter's birthday party. We worked together for almost two years and had a real relationship. And something snapped in her.
[00:15:00]
KATE KORDSMEIER
I'm not saying I'm totally blameless in the situation, but the way it was handled was so stressful. I definitely remember thinking, "I'm not cut out for this. I should just close my business." And now, five years later, you can almost look back on it and laugh. It's still a little "ouch" — because it was such a close relationship. But I think the moral of this roundtable is that people are unwell, and we have no idea what's going on in their lives. I did come to find out later that she was going through a divorce and her mom was in the hospital. I think oftentimes these things say a lot more about that person than they do about you. Sometimes you just have to let people be wrong about you. I know the truth. As long as I can stand in integrity with how I behaved — even if I made a mistake, how I handled it — sometimes that's just all you can do.
LIZ STAPLETON
Yeah. I like that. Does anyone else want to add anything before we move on?
LIZ STAPLETON
Okay. I'm just curious — have you noticed, or have you come to see, a pattern of early signs that someone might be difficult to deal with later? Anything that jumps out?
JORDAN GILL
Yes. Love bombing. It feels very similar to relationships. Sometimes when somebody comes in real hot and says, "I can't believe I found you. You're going to save me." It feels really good at first — you're like, "Oh my gosh, this person loves me." A lot of times, those people have gone on to be a little... cray.
LIZ STAPLETON
I like that. Anyone else? Alright, moving right along.
Boundaries & Policies
LIZ STAPLETON
So I want to know — what boundaries do you guys enforce now that maybe you didn't before? A lesson learned of having to set a boundary?
DR. DESTINI COPP
I'll jump in here. One thing I'm very clear on — and I tell the contractors working with me that this is something they can enforce — I have a zero tolerance policy for people being mean. So when anybody comes in to one of our free events, and I'll use HobbyScool as an example: if anyone is complaining openly without even contacting us, or they've sent a really mean and nasty email to one of my contractors or our help desk, I give permission to kick them out of the event, unsubscribe them from our email list, and block them from our ThriveCart account so they cannot purchase from us. We don't want those types of people in our world. Same thing if they're posting on social media and being nasty there. We will absolutely just cut them off immediately with no warning. You don't even have to tell them. Don't waste your time responding or explaining.
DR. DESTINI COPP
Now, if they have a valid concern and they're nice about it, that's a different story.
KATE KORDSMEIER
The thing is, you can have in your policies a "no shoes, no shirt, no service" clause. It's the same kind of idea — we have the right to refuse service to anyone. Just make sure it's in there, and that's going to protect you a long way.
FAITH MARIAH
I also love — if anyone even threatens a dispute, I don't care whether they follow through or not. It's an immediate blacklist. I don't want you as a customer in the future. A hundred percent blacklist.
[00:20:00]
KATE KORDSMEIER
One of mine that I was thinking about was — this sounds nuts now, but when I first started my business, we didn't have any policies for refunds and stuff. And I found us always having these conversations — me and my business manager Rebecca, or me and my VA — and it was almost like, whose trauma is bad enough to deserve a refund? That was just really stressful, because if you don't have a policy, I don't think you can be fair. I can't treat everybody the same and then say, this person deserves a refund but this person doesn't, just based on how bad their situation is. So for me, the big boundary has really been having terms and policies that are the same pretty much for everyone, and we just follow the policy. That takes the emotional component out of dealing with this stuff. And it allows my team to handle it without me most of the time. I usually only have to step in if something's really bad, someone's really unhappy, or something's really wrong.
RUTH POUNDWHITE
I think that's so true. Something I heard a few years ago is that it's actually kinder to uphold your policies, because otherwise it's exactly what you said — you're judging people on a case-by-case basis depending on how compelling their story is. Some people will give you all of the reasons. Some people are genuinely struggling but won't say so. Being kind to everyone — including yourself and your own business — is just having a policy and sticking to it across the board. Because just a hundred dollars can make a difference for the customer, and it makes a difference for small business owners too. It goes both ways.
Refund Policies & Philosophies
LIZ STAPLETON
So let's actually dig in. What are your refund policies or philosophies, and has that changed over time? I think we've all touched on having a policy being important — and it doesn't mean you can't find other ways to be generous. In the past, what I've done is say, "Hey, I can't give you a refund — these are our terms. But if this is truly not a product you're going to use, I'd be happy to cancel and give you credit toward something else." That provides a solution while still upholding the policy.
KATE KORDSMEIER
I've tried lots of different refund policies over the last decade-plus, and I feel like I'm in a place now where I've found what feels good for me. There's no one right answer — it really does need to be business owner to business owner. I used to do a refund within a certain period of time, usually two weeks, but you had to prove that you tried it. I think I got this idea from Amy Porterfield way back in the day. I liked that it was supposed to weed out the tire kickers — people who come in and never do anything and then ask for a refund. But I found it made things so difficult. Sometimes people are like, "I didn't need to try — I could tell this wasn't going to work for me." So I got rid of that.
[00:24:00]
KATE KORDSMEIER
I went to a no-refunds policy, period — because a lot of what we sell is digital products, and once I've given it to you, it's yours. It's not like a shirt where you could keep wearing it after you return it. So no refunds felt clean. But then that didn't feel like it was in integrity for me either. So I switched — I think it was last year, maybe two years ago — to a seven-day refund policy, no questions asked. If you get in and take a look and decide it's not for you, you can get a refund. You don't even have to tell us why. Of course we're going to ask for our own feedback, but we're not going to decide your refund based on your answer. And that has felt so much better to me. Interestingly, I think our refunds have gone down, and I think we make more sales because people feel safer to buy. Most people — 98% plus — get in and say, "This is great, I would never want a refund anyway."
JORDAN GILL
I have always had a no-refunds policy, and that's what feels good to me. The reason, going back to when I was starting my business — I was a single woman, and that was my livelihood. If I didn't make money, I wasn't eating. I didn't have anyone to fall back on. And I've re-thought it since then — does this still feel good? And for me, it just does. When I purchase something, I'm never thinking, "How can I back out of this?" I just think: even if I learned one thing from this, will I still be okay sending this $37, this $1,000, this upwards of $24,000? That's a decision I have to make.
JORDAN GILL
I think there have only been two times in 10 years of business where I've even asked for a refund. One had to do with a course that said "instant access" but was actually drip content with a quiz required after every module. I was like, this isn't my learning style. They didn't give me a refund, so I called it a wash. The other time was a values mismatch.
[00:27:00]
JORDAN GILL
I honestly don't remember the last time I got asked for a refund — because on my checkout pages I have a checkbox: "I agree to the terms and conditions of no refunds." You literally cannot buy unless you check that box. That's been the cleanest thing for me, and I'm sticking to it.
LIZ STAPLETON
I will say there is a rule coming out of the EU regarding refunds that's supposed to take effect next month. I need to dig more into it. I know there are exceptions for digital products, but it might be something you need to update your terms to cover — just an FYI to everybody.
LIZ STAPLETON
And that kind of leads into our next question: What systems have helped reduce refund requests? You just said people have to agree to no refunds at checkout. I've actually started using that as well since ThriveCart added that functionality. Does anyone else have systems or policies that have helped reduce refund requests?
DR. DESTINI COPP
I could tell you — on our checkout pages for HobbyScool, and I have to be clear: it is different in the B2C market than it is for my B2B brand. My B2C brand, just the volume there — you're getting a lot of people coming in, people forget, it is just a different beast. But on the checkout page, I put it very clearly: we do refunds within 14 days, and that's been our standard there. I feel good about that because they're having to make a decision quickly on the tripwire. For our VIP passes, it is on the checkout page, and it does say that 14-day deadline.
[00:30:00]
RUTH POUNDWHITE
Some of what Jordan was saying was making me think about how important it is to act in integrity with your own values on this. I'm not someone who would ask for a refund unless there was genuinely something mis-sold. I'm paying for something right now on a fixed term and I'm not using it, and I'm annoyed about it — but I'm going to finish my payments and I'm not going to ask for a refund. Sometimes people are clearly looking at their expenses from months back and trying to claw back money, and it's just really unfair. But the importance of being in integrity — and I know for some people, their version of integrity when they use countdown urgency is to have a refund period, because at least if they're encouraging someone to make a fast decision, they know people can ask for a refund. Personally, I don't offer refunds. It feels a lot easier and cleaner for me right now. But yeah — just think about what integrity means for you as well.
KATE KORDSMEIER
It makes me think, too, about failed payments — which are their own form of a refund. It's not necessarily money you had that gets taken back, but it's money you were counting on that doesn't come in. That might be a good direction to go, Liz.
Failed Payments
KATE KORDSMEIER
I understand that some people really do get themselves into a situation where they cannot make their payments, and when those people communicate that to us and we come up with a repayment plan, that's just cost of doing business. The people that just drop off, or treat what is — to me — a gracious offering of a payment plan like it's nothing... We have terms everywhere on our site saying very clearly: this is not a membership, this is not a subscription — you are legally obligated to complete all payments. And people just ghost you. We have some people who fail every month, then eventually fix it, then fail again. Some people in our mastermind have decided not to offer payment plans for that reason. I get tempted sometimes. But when I look at the data, I can see that we made a lot more sales than we would have made without the payment plan.
[00:33:00]
KATE KORDSMEIER
Because of our policies, if somebody fails their payment, they're immediately removed from the program — completely — and access is not reinstated until they finish out their payments. So I think of it as: I got $200 from somebody that I would have gotten $0 from if I only offered pay in full. And they don't have access anymore. To me, it's still worth offering it. But it is a huge pain.
LIZ STAPLETON
Yeah. I fall into the same thinking. The one thing that pops to mind is: I should really set up a system so that if someone has failed a payment, they can't buy from me again until they've completed it. That's a little trickier to set up. But a lot of times I don't think people are blatantly ignoring the failed payment — they don't see it, or they don't realize until they try to log in and can't. But having that system in place would be great: "Sorry, you still owe me money."
RUTH POUNDWHITE
I wanted to add to this. Way back when I had a business for agents, payments would sometimes fail because I hadn't moved money around, and I used to think it didn't matter — I just thought it would eventually sort itself out. To anyone listening who thinks it's okay and eventually it'll go through — please communicate. I was that person, and I realize it does matter and it makes a difference. I had a situation where I ran a summit last September with an unprecedented number of failed payment plans — on a fairly low-cost offer. People don't always see the emails, so there are always genuine reasons. But if you see a failed payment in your bank app or bank statement, please be proactive. We are never angry when someone contacts us and explains or asks for a different arrangement. We can talk about it. But when you don't respond, it's such an admin burden. So please, if you are like I used to be, don't be like that. Just communicate.
[00:37:00]
JORDAN GILL
I would also like to share — I know all of us have our different attorneys, but when I was running my large group program, one of my attorneys basically keeps a blacklist. She's an attorney for a lot of people across the industry. So if a student was trying to pull one over on me, I'd say, "Hey, can you check this name and email on your blacklist?" And if they aren't on there, she actually adds them with a little note about what happened. There are people who do this across a bunch of businesses. Because she has so many clients in the space, she's able to cross-check and have evidence of patterns. If someone tries to come at people crazy, she can say, "I already have three other clients you've done this to." So people talk. We have a mastermind, and we absolutely name names sometimes. We've all gone and blocklisted those people.
KATE KORDSMEIER
I'm sure everybody here is lovely and would never do anything like this. But tell your friends. Save your friends.
FAITH MARIAH
And do not post it publicly, because you could get in trouble with data privacy laws.
JORDAN GILL
Just in your little groups you can chat about it.
KATE KORDSMEIER
We can gossip — just in secret.
Mindset Shifts
[00:39:00]
FAITH MARIAH
I had a pretty big mindset shift around some of this stuff. It used to be a really big energy leak for me. I've always offered interest-free payment plans and a two-week no-questions-asked refund policy, so I always feel like we're being really generous. And when people were not being generous back and making us chase them down — at the beginning of my business, it felt very personal. Like, this is my work, how could you do this? And now I'm laughing because I'm just so detached from it. I have the policies, the team sends the emails when payments fail. I know some people are not going to finish their payment plans, and I'm okay with that.
FAITH MARIAH
The thing that really helped me was padding my savings account to the point where I don't need that money day to day. I'm a marketer. I believe in my ability to go make other money if I need it. When Matt and I had our Airbnb, our property manager called and said guests wanted a refund. We didn't have to give them a refund at all. And I just told Matt, "Give them their money back." They're going to be in our home, around our neighbors — it's just not worth it. Sometimes giving the refund has been a way of closing things out that actually feels good. It doesn't always have to feel like your boundaries are being pushed over. It can feel like, "Yeah, this is a relationship that needs to end and I'm happy to give you this money back." I really don't feel dysregulated by it anymore.
LIZ STAPLETON
This leads perfectly into the question of what mindset shifts have helped you handle these situations better. Kate?
[00:42:00]
KATE KORDSMEIER
I'll just second what Faith just said. I had another difficult experience in business that wasn't about a refund. Some of you might know — I sold a business in 2021, and the buyer ended up stealing over $25,000 from me over the last couple of years, even as recently as 2025. It was horrible. I contacted her, I talked to the mastermind about it a ton, I spoke to three different lawyers trying to figure out my options. And ultimately I came to the same decision that Faith did: this is not worth my time and energy. I can go make $25,000 faster and easier than I can chase this money down. At a certain point, the energetic leak and how negative and scarce it made my mindset was just — this is not worth it. I've got to walk away.
KATE KORDSMEIER
There was part of me that was like, "This is so unfair. I can't believe I'm just letting this happen." But ultimately it was totally the right call, and I more than made that money back.
RUTH POUNDWHITE
I think you handled it amazingly, Kate. My question to you is — that's a lot of money. That's a huge thing, and there's that sense of justice as well. Did you have to process anger? Shame too, I'm guessing — even though you had no reason to feel ashamed?
KATE KORDSMEIER
Yeah, definitely. It wasn't a one-time thing where she quickly stole $25,000 — there were multiple scenarios and ways she did this over time. But yeah — when one of the situations came to light, my Kartra account was still linked to my old PayPal and I didn't realize it. So all of my sales going through PayPal were getting deposited into her account, and she knew it. I had a panic attack when I first realized what was happening — just a total shame attack of, "How could I have been so negligent? How could I have missed this?" I was so mad at myself. And yes, there was definitely therapy involved. A lot of talking with y'all. I went to lunch with Destini and we really talked through the practical options, weighed the outcomes, and yeah, it was a lot to process. I appreciate you saying I handled it well, because it did not feel like I was handling it well.
[00:45:00]
RUTH POUNDWHITE
I feel like I put you a bit on the spot there, grilling you about it. But I do think it's so important to share how you really felt, and how hard it is. It's really helpful to hear that everyone goes through this stuff. And I'm sure you've learned really important lessons. I've always learned something about myself, my policies, or what I could do differently next time. So thanks for being open. And I hope it's helpful for everyone listening too — to know that we blame ourselves sometimes when we really shouldn't. Let's not blame ourselves for blaming ourselves. It's a human aspect.
LIZ STAPLETON
Yeah. Sometimes the best you can do is figure out how to prevent it from ever happening again, update your policies if needed — which I've definitely done — and then move on. As much as it sucks, sometimes that's the best solution. You already have so much on your plate. To have to carry that as well is just... it sucks. Sometimes you have to stand your ground, but sometimes the best thing is to just make sure it doesn't happen again and move on.
KATE KORDSMEIER
I want to say one quick thing and then I feel like we have to turn this over to Destini for "What Would Destini Do?" mindset — because she's our resident bulldog.
KATE KORDSMEIER
About the beating yourself up: you get a refund request and maybe it's even legit. Maybe you're like, "Dang, that wasn't as good as it could have been" or "I wasn't clear about that" or "I missed this." We all make mistakes. At first I really beat myself up and was so ashamed I had missed it. And then ultimately I was like — of course you're going to miss some things. Some balls are going to be dropped. You're one person managing a whole life and a whole business. Of course stuff like this is going to happen. It's shitty, and I wish this person wouldn't have taken advantage of my honest human mistake, but here we are.
[00:47:00]
LIZ STAPLETON
So we've referenced this a couple of times — but we do have "What Would Destini Do?" And Destini has beautiful boundaries. What we all love so much about it is that Destini is also one of the kindest, most generous people that we know. So it's not that we're saying, "Oh, stick the bully on them" — because Destini has this wonderful way of holding boundaries and being kind. So I feel like you need to share some of your mindset, Destini.
[00:48:00]
DR. DESTINI COPP
I don't know if I'm perfect here for sure, but I'll talk about a situation that happened to me this week because it's just fresh in my mind. Basically, I was going into my Facebook Business Manager for my ads. We were running ads for our event this week — the Eco-Creative Summit for HobbyScool. And people are crazy. I was reading the comments on these ads and one of the images was basically talking about how you can take things around your house and do crafts with them — there were pictures of paper towel tubes and toilet paper tubes — and there were comments like, "You can't use that, there's fecal matter on that." Or: "Why are you using AI-generated images on your ads while claiming to be eco-friendly?" And I'm thinking, oh my gosh, I'm going to lose it.
DR. DESTINI COPP
And then people were saying things about the tripwire offer on the next page after registration, calling it "pressure sales" — "Why are you doing pressure sales on me? You said this was a free event." And I went and looked at who was actually saying that. The comments were coming from other businesses. I had to calm myself down, change my mindset. Some of them I responded to, some I didn't. For some I just said, "It is a free event. You don't have to purchase the VIP pass. But we are a business, and we are here to make money. And a lot of people love having our VIP pass because they get lifetime access to the workshops." Those types of things are going to come up when you have a business. You just have to regulate yourself, respond to some, ignore others, and close it and walk away from it.
FAITH MARIAH
And knowing you, Destini — you are doing so much in your life and your business, you do not have time for it. None of us do. But as Faith said earlier, it is such an energy drain. Even if we're doing other things, when it's in the back of your head and you're stewing over it, it just gets in the way of so much. You can never, ever please everyone. You just can't.
Freebies & Resources
[00:51:00]
LIZ STAPLETON
I think we're going to call it there. So let's go ahead — if you guys want to each share what gift or freebie you have. Kate, I'm going to start with you.
KATE KORDSMEIER
Okay, great. I know we didn't even get to talk as much about trolls and negative comments and how much that can drain you too. So we'll bookmark that for next time. My freebie: you all know I'm the "social-free girl." I created a free tool where you enter your bio and pick a stage of business you're in, and you'll get 10 custom prompts just for your business. They're hyper-specific about how you can grow your business without social media. You can put them into Claude and it will generate different assets to help you. Or if you're not social-free and just want to rely on social media less, it'll give you some ideas too.
DR. DESTINI COPP
All right, Destini. So going back to "What Would Destini Do?" — I did create a Claude skill for you. I pulled a lot of different scenarios based on how I specifically handled those situations. So you can download that Claude skill from the links in the document.
LIZ STAPLETON
Yeah, and I did share that link in the chat. Ruth?
RUTH POUNDWHITE
I have an AI sales toolkit to help you use AI to take some of the cognitive load out of selling, and to help you figure out what you need help with. There's a link in the document.
FAITH MARIAH
My offer is called The Coaching Files, and it is a replay from a coaching call from an event I did a while ago. If you're feeling stuck in your business and need some outside perspective or somewhere to bounce ideas around, we do that in my community. You can watch the call and if you need help, reach out.
LIZ STAPLETON
And Jordan just shared her Instagram in the chat. And then my gift is a little mini eBook on winning payment disputes, which walks you through how to handle them. I have photo evidence included — obviously with any personal information redacted — as an example. So if you're not sure what to put in your evidence while dealing with a dispute, that book will help you. It's also in the doc.
LIZ STAPLETON
So thank you all for joining us today. We are the Weird Hermits, and we run these roundtables every other month. If you have ideas for topics, I put the link in the chat where you can submit them — because we love not having to come up with topic ideas ourselves. Hopefully we'll see you guys at the next one. Thanks everyone!
ALL
Thank you! Bye-bye!
DR. DESTINI COPP
Thanks for listening all the way to the end. I hope you enjoyed this episode today. If you love the show, I'd appreciate a review on Apple Podcasts or your favorite podcast platform. Have a great rest of your day, and bye for now.