Send us a message! Not every guest stay ends with a five-star review. Some leave behind a mess. Some turn into a serious operational headache. And some become the kind of story you end up telling for years. That is the idea behind Pour Decisions: When Stays Go Sideways, a special series presented by Safely. In this series, Alex & Annie sit down with the Safely team and industry guests to unpack the kinds of guest incidents that rarely make it into the marketing copy but often leave the biggest operational impact. Through real stories, practical insight, and a little cocktail-fueled commiseration, the series explores what went wrong, how it was handled, and what operators can do to better protect their homes, teams, and owners. About Episode 1: In this kickoff episode, Alex & Annie are joined by Amanda Martins, Vice President of Business Development at Safely, to introduce the series and set the stage for the conversations ahead. Amanda shares what Safely sees behind the scenes when guest-related damage claims come in and why these stories can be some of the most useful lessons in the business. The episode also dives into one recent case involving a large home that became the site of a 50-person party, complete with police involvement, extensive damage, smoke remediation, and a long list of cleanup issues. Amanda walks through what happened, the documentation that helped support the claim, and what operators should be thinking about when it comes to guest screening, damage protection, liability, and owner communication. It is a practical conversation that sets the tone for the series ahead, showing how real guest incidents can reveal where systems hold up, where they fall short, and what operators can do to better protect their business before the next stay goes sideways. In this episode: 01:41 - Meet Amanda Martins of Safely 03:34 - Why Alex & Annie launched this special series with Safely 08:34 - A real story involving a party that caused major property damage 15:01 - How Safely’s claims process works 16:31 - What happens if an operator does not have damage protection 19:01 - When operators should involve police or pursue legal action 24:06 - Why guest screening can help deter the wrong bookings 28:28 - Protecting homeowners and reducing business risk 30:20 - How Safely works alongside homeowner insurance 36:55 - Why this matters for operators of every size Have a story to share? We want to hear your worst guest stories. If you have a stay that went completely sideways and a lesson to go with it, submit it for a chance to be featured on a future episode. Submit your story here: https://form.jotform.com/261032817700044 Connect with Amanda: LinkedIn: https://www.linkedin.com/in/amandakatmartins/ Learn more about Safely: Website: https://safely.com/alex-and-annie LinkedIn: https://www.linkedin.com/company/safely-stay/ This episode’s cocktail: Checkout 75 A little classy, a little dangerous, and apparently best enjoyed seated. Ingredients: 1 oz tequila0.5 oz GranGala0.5 oz fresh squeezed lime juice0.5 oz fresh squeezed orange juiceSparkling wine, such as prosecco or a dry brut, to topHow to make it: Shake the tequila, GranGala, lime juice, and orange juice with ice. Strain into your favorite wine glass, then top with bubbly. Amanda’s final tip: Don’t stand up too fast when finished. #vacationrentals #shorttermrentals #guesthorrorstories
