Madeleine Raiford-Holland: Hey there, I'm Madeleine and welcome to The Luxe and The Short of It podcast. I'm a military wife, mom, and entrepreneur that went from a stressed out nine-to-fiver to now a present-minded seven-figure business owner and investor, all through the power of short-term rentals. Here we believe the Luxe life means having the time and financial freedom to be present for the moments that matter most. And I'm here to teach you the exact mindset shifts, insider expertise, and business strategy to make that a reality for you today. So are you ready to actively create the life you want? I'm Madeleine and this is The Luxe and The Short of It podcast.

[00:01:01] Welcome back to this episode of The Luxe and The Short of It. We have a bit of a fun episode for you guys. Abby is here. You guys know Abby, my marketing director. And we were a little bit bored, if I'm being perfectly honest. And we were saying, what could be a fun podcast episode? And I said, "Well, we should play a game of Smash or Pass Short Term Rental Edition." So Abby did what she does best, even though it's a lot of things. She asked the robot to come up with a list of unhinged things that people may actually ask, and I will decide if I would smash it or pass on it. So without further ado, Abby, let's dive right on.

Abby [00:01:54] This is probably going to be one of the most fun episodes that we have done.

Madeleine Raiford-Holland [00:01:59] If it's not fun, then why do it?

Abby [00:02:02] Exactly. That's what we talked about in the last one. Exactly.

Madeleine Raiford-Holland [00:02:06] Authentic. Let's do it.

Abby [00:02:08] All right, number one. Would you offer a cash back incentive for guests who actually read the house rules?

Madeleine Raiford-Holland [00:02:19] Smash. I would absolutely smash that. And I would choose something like putting all the house rules in there and on the bottom one say if you've made it this far, send me a message with like an obscure word. And I'm going to send you five bucks. Coffee on me. Kudos to you for reading it. So I don't advertise it to the public, but I would absolutely do that. And I may end up doing that in future listings. That would that would be fun, like a fun game, setting the vibe, setting the tone for some fun.

Abby [00:02:53] Nobody ever reads directions, so I think an incentive might...

Madeleine Raiford-Holland [00:02:57] Incentivize people to read it. I mean, they won't know, but it rewards the freaking action takers, the people who do the right thing. I'm here for it.

Abby [00:03:05] Exactly. What else should you do? As you get more loyal customers, they know for the next time they'll be ready. All right. Would you spend $600 on a neon sign for your listing just because you saw it on Instagram?

Madeleine Raiford-Holland [00:03:23] I'm not a neon sign girly personally. It doesn't really fit with my esthetic or my guest avatar. So I personally would probably say pass. However, it could be a smash situation depending on your particular guest avatar. So I want you to know who you're hosting, why they're coming. And with that, I want you to be able to be able to speak to that target person and that demographic. And if you are mainly hosting bachelorette parties or that type of vibe, a neon sign can be a slam dunk and $600 is-- I haven't priced neon signs, but I think it's fairly reasonable, right? Do you know?

Abby [00:04:07] No, that's not too bad for one. I totally agree. Would you outsource guest messaging to your teenage niece for work experience?

Madeleine Raiford-Holland [00:04:21] Is there like a it depends option or is it just smash or pass? Like what's the rules of the game?

Abby [00:04:26] Smash or pass.

Madeleine Raiford-Holland [00:04:27] I want to say pass because well, one, my niece is about to turn one. But in the world of teenagers, you just don't know what you're going to get. Sometimes you've got some really sharp crayons in the box, and then you've got some that are not quite as sharp. So I'm going to say overall, when my revenue is on the line, I'm going to pass on that one unless it's a very extenuating circumstances with somebody who is just super bright.

Abby [00:05:00] I think I know your answer to this one. Would you let your cleaner set their own rates and booking times just to keep them happy?

Madeleine Raiford-Holland [00:05:08] No. Pass. My cleaners already set their own prices. We negotiate that ahead of time. None of them are on hourly. It's all a set fee structure for the cleaning, and that always includes linens, guys. And sometimes that works in their favor if one guest stays and they're barely there and none of the other rooms are touched and all of that. Other times it doesn't work in their favor and they have a full house. It's the same price regardless. That's how we rule things. But my expectation is that regardless of if I have a turnover, my properties are ready at four PM. No if, ands, or buts about it. So pass fully on that one.

Abby [00:05:48] Absolutely. Okay. This one's funny. Would you post a TikTok dragging a guest's insane request and then DM them the link?

Madeleine Raiford-Holland [00:06:03] Well, it wasn't a request, but I absolutely just drugged somebody, a guest, through the through the mud for leaving 100 tiny Jesus statues in my Airbnb and expecting my cleaner to pick it up. That was just a public service announcement for everyone. Do not put those Jesus statues anywhere in anybody's Airbnb. They're choking hazards, first and foremost. Two, it just creates the extra work. I'll get off my soapbox. I pass just because I wouldn't send it to the person. I kind of wanted to send it to that woman, but she was just hateful in general. So I didn't send that. I don't think that stirring up drama is my style so pass, but absolutely I'd post about it on social media.

Abby [00:06:59] It's how you get the views with all the craziness. That's what everybody wants to see.

Madeleine Raiford-Holland [00:07:04] Exactly.

Abby [00:07:05] Okay. Would you build an outdoor shower even if you live in Michigan?

Madeleine Raiford-Holland [00:07:11] I don't know if I've ever been to Michigan in general, but I know it's kind of cold up there and I know they have lakes. So smash if it makes sense for that market. So that's where the market analysis piece definitely comes into play, knowing what your market requires. If it's a lake market that people are in and off boats and in the pool and it's a summer market where people are really loving the outdoors, I would absolutely put an outdoor shower but make sure it was weatherproof in the winter. My Michigan folks may be saying there is no way. That's asking for burst pipes. I don't know, but from my minimal knowledge of Michigan, if the market called for it or if it was a way to differentiate myself and I could do it well and protect it from the elements, smash.

Abby [00:08:00] Would you let your ex manage your STR remotely if it meant not having to deal with any guest drama?

Madeleine Raiford-Holland [00:08:14] It's been a long time since I have had an ex. In January, I will have been married for 10 years, folks. Hopefully water under those bridges to where I could smash that and say, sure-- not smash the ex. Smash the situation. All of my exes are relatively responsible human beings. I want to give myself a little bit of credit that I wasn't with losers. So I'd say smash. Abby, do you want to answer that question?

Abby [00:08:52] I pass hard on that.

Madeleine Raiford-Holland [00:08:56] That's a big old pass for Abby.

Abby [00:09:01] No trust there. All right, next question.

Madeleine Raiford-Holland [00:09:03] No trust.

Abby [00:09:05] Would you use AI to respond to reviews even if it accidentally called someone bro?

Madeleine Raiford-Holland [00:09:14] Smash. Generally, AI responds in the tone, or at least that's how we train our AI to respond in a tone that somewhat matches the guest. I typically wouldn't want to call somebody bro, but if it's one casualty and it does great the rest of the time, smash.

Abby [00:09:40] Okay, would you set up a fake security camera labeled guest behavior monitor just to keep people in line?

Madeleine Raiford-Holland [00:09:48] Pass 100%. That is invading people's privacy and then we would be reported to Airbnb. Absolutely not. We are not hall monitors and I do enough behavior monitoring with the four-year-old and the two year old. I am not trying to get into that business.

Abby [00:10:08] Exactly. Okay. This is funny. Would you reply to a guest's two star review with a custom Canva graphic that says, "Thank you for your opinion?"

Madeleine Raiford-Holland [00:10:23] No. Pass. Pass on that one because I don't think that you can respond with photos, but two, as a lesson, folks, the review response is not for the person that left the review. It is for every future guest who's going through and reading it. We had a client, and I love her dearly, that came to our program and we were auditing her listing on her very first day. And she had a one star review. The review said, "Roaches. No." She launches into this elaborate story with us of how she caught it on camera the guest was bringing in a roach from the outside, put it inside the listing, but her review response literally said, in all caps, first line, "You are a filthy liar." And proceeds to write an entire paragraph explaining why these people were terrible guests, filthy liars, like the whole thing. And I had to say, like, keep a straight face of like we cannot say that. In no scenario is it okay to call a guest a filthy liar because the review isn't for that guest. It is for all future guests. So we need to present ourselves as professional hosts who care about feedback, but also present our side of the situation in a professional manner that lets them know that one, we care, two, whatever happened may not have happened, but not calling people a filthy liar.

Abby [00:12:04] Yeah, it's not okay.

Madeleine Raiford-Holland [00:12:07] So pass. Passive aggression also falls into that no category with the Canva template. So no.

Abby [00:12:15] Definitely a pass. Okay. Would you create an Airbnb profile just to spy on your local competition's response time and pricing? Good one.

Madeleine Raiford-Holland [00:12:27] That is a good one. Smash. I mean, secret shop all day long, folks. Yeah. That's also part of why we have dynamic pricing software because you can see your pricing in the competition without having to go through that trouble. But response time, guest messaging. I'm going to tell you this is some tea. We were going into a new market down in Orlando, Florida. I have since gotten out of that. It was an arbitrage unit, but we were going down there to set up the property. And even though I knew I wasn't going to stay there, I booked the condo next door to the unit that we were booking. It was a gated community. There was a lot of nuances. There were like codes for the pool and all the things. And I wanted to know how they communicated that clearly to the guests. So I booked the condo next door while we were setting it up. And I copied all of their guest messaging instructions because it was putting the easy button. Work smarter, not harder. Leverage those folks. Do not ask them. Do not be one of those people. This drives me insane. And yes, community over competition, but we get people all the time who request to book dates. Your properties look so clean. Would you mind sharing your cleaning people with us? No, we'll not. Period. End of story. I'm getting a little riled up this episode.

Abby [00:13:59] Next is my favorite question. Would you copy and paste a guest's rude message into Chat GPT and ask it to clap back like Cardi B?

Madeleine Raiford-Holland [00:14:17] Smash. If nothing else. Just to have the emotional release and the laugh behind it so that I could respond with a clearer head. Sometimes humor is the best medicine when they are being rude and passive aggressive. Obviously, you can't respond like that, but sometimes you just need to lighten the mood a little bit and having it clap back like Cardi B might give you some good ammo that you can modify to respond professionally.

Abby [00:14:49] Would you use your Airbnb reviews as your dating app profile bio?

Madeleine Raiford-Holland [00:14:55] I think it would be kind of humorous. The whole point is to stop the scroll and interrupt people's thought patterns. It's like this is what my Airbnb guest has to say about me. I'm communicative, very hospitable. Five stars. I don't have an online dating profile. Do you, Abby?

Abby [00:15:18] I do not.

Madeleine Raiford-Holland [00:15:20] Are you sure?

Abby [00:15:22] I'm sure.

Madeleine Raiford-Holland [00:15:24] Would you use it in your dating profile?

Abby [00:15:28] I would. It's unique and it'd be I mean five stars being in this--

Madeleine Raiford-Holland [00:15:37] Conversation starter, right?

Abby [00:15:38] A hundred percent, yeah. It would just show off all my good qualities because that's what we do.

Madeleine Raiford-Holland [00:15:44] Super clean, very communicative. All things check the boxes in a partner.

Abby [00:15:51] Everything. Yeah. Would you name your STR something so unhinged like bread and bougie or the moist manor just to go viral?

Madeleine Raiford-Holland [00:16:03] Oh my gosh. Just because it uses the word moist, I'm going to say pass. You may not know this about me. I have three words that I cannot stand. Three words. And I'm curious if you feel the same way. Like moist, ooze, secretion. They just give me such ick.

Abby [00:16:34] I know a lot of things about you. I did not know what you were going to say there.

Madeleine Raiford-Holland [00:16:42] Gross. I cannot stand that. And the fact that you just said moist manor. Yuck. We recorded a bunch of content a few weeks ago and one of the things was there's an Airbnb host that advertises his listing based on the number of "baby making spots" that are in his listing and his listing photos have arrows pointing to all of those places.

Abby [00:17:16] So smart.

Madeleine Raiford-Holland [00:17:16] It sounds like the moist manner might be right up his alley. But it's also giving me like Kim K bush underwear. I'm all for a viral moment, but that is not on brand for me. So that's going to be a hard pass.

Abby [00:17:38] Here's our last question. So I'm going to ask it and then based on your answer, I think we can tailor it a little bit. So would you spend more on throw pillows than your monthly car payment and feel zero regret? Now if your answer is pass, then I want to know what you would spend more on.

Madeleine Raiford-Holland [00:17:58] Smash because I've done it.

Abby [00:18:01] I know.

Madeleine Raiford-Holland [00:18:03] It depends on the size of the property, but those things like add up quickly if you're-- I've got properties that have two living rooms, four bedrooms. I mean, that adds up in a heartbeat. On an individual throw pillow, absolutely not. But if I'm furnishing an entire property, I've done it more times than I can count or want to admit.

Abby [00:18:30] You have to.

Madeleine Raiford-Holland [00:18:31] Well, this was fun.

Abby [00:18:32] That was fun.

Madeleine Raiford-Holland [00:18:34] I hope that you guys got some knowledge from my answers there and enjoyed listening. Stay tuned. I think we're going to do this again. Abby had the idea to do what was it? Marry, kiss, kill.

Abby [00:18:46] Kiss, marry, kill. That'll be our next.

Madeleine Raiford-Holland [00:18:47] Kiss, marry, kill. So stay tuned for your next fun-filled episode of the Luxe and the Short of It. Shameless plug here. If you want to have me answer questions like this or learn how to run your short-term rental better, join us for our next workshop. We're going to drop the link in the show notes.

Hey y'all, if you're loving the show, be sure to hit the follow button or the plus sign on your podcast app to subscribe. This will ensure you don't miss a single episode and I'll see you next week.