Alex and Annie: The Real Women of Vacation Rentals

Send us a message!In this episode, Alex & Annie sit down with Frank Bosi, Senior Director of Partnerships at Hostfully, to unpack what it really takes to build a tech company that people trust.Frank’s journey began in luxury hotels long before short-term rentals became a professionalized industry. That hospitality foundation now shapes how he approaches partnerships, leadership, and growth inside one of the most culture-driven PMS brands in the space.This conversation explores why culture scales faster than software, how AI can actually bring hospitality back into operations, and what property managers should be focusing on as expectations rise across the industry.You’ll also hear a behind-the-scenes look at Hostfully’s approach to partnerships, onboarding, and product development, including how real user feedback influences what gets built next.Episode Chapters:00:00 – Welcome to Alex & Annie: The Real Women of Vacation Rentals05:00 – Frank Bosi’s role at Hostfully and his focus on partnerships, education, and industry visibility09:40 – Frank reflects on his hotel background and why consistency, care, and service still define great guest experience21:17 – Inside Hostfully’s day-to-day culture, trust, flexibility, and leadership principles15:14 – Why Hostfully feels different to operators and how people shape the product experience10:43 – Using AI intentionally to preserve brand voice, personalization, and hospitality40:28 – The biggest challenges operators are trying to solve right now16:36 – Collaboration, ecosystem thinking, and why relationships still matter in tech36:28 – How Hostfully supports operators at every stage of growth26:00 – Hostfully’s funding story and choosing partners aligned with long-term valuesFrank also shares his perspective on industry consolidation, rising professionalism among operators, and why modern property management systems have become the backbone of scalable operations.This conversation explores what happens when technology is built around people, not the other way around.Connect with Frank:LinkedIn: https://www.linkedin.com/in/frank-bosi-375a5817/ Connect with Hostfully:LinkedIn: https://www.linkedin.com/company/hostfully-inc-/ Website: https://www.hostfully.com/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).👉 Click here to get started: https://cal.mixmax.com/frankbosi/demo #vacationrentals #shorttermrentals #PMS

Send us a message!Welcome to the 1st of the year special episode. Alex & Annie are kicking off 2026 by looking back at the moments that shaped 2025, the lessons they’re carrying forward, and the intentions guiding the year ahead.They share how the podcast evolved over the past year, including more on site recordings and conference conversations than ever, plus why storytelling is becoming a bigger advantage for vacation rental brands right now. You’ll also hear Alex’s personal announcement, perfectly timed for the Year of the Horse, and the top episodes of 2025 that listeners loved most.Episode Chapters:00:00 Welcome to the First Episode of 2026  01:05 Why This Annual Episode Matters  02:45 Reflecting on the Moments That Defined 2025  06:10 Taking the Podcast On Site and Into Conferences  08:50 Travel Stories, Italy, and Unexpected Highlights  13:20 What’s Coming in 2026 for the Podcast  16:45 Words of the Year and Personal Intentions  27:30 Alex’ Personal Announcement and New Chapter  35:50 The Top Episodes of 2025  52:10 Gratitude, Community, and Looking AheadWhat’s your Word of the Year for 2026? Send Alex and Annie a message on LinkedIn. They genuinely want to hear what you’re focusing on this year.✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).👉 Click here to get started: https://cal.mixmax.com/frankbosi/demoGet 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.#vacationrentals #shorttermrentals #strindustry

Send us a message!In this episode, Alex & Annie sit down with Arlen Busenitz to talk about his unconventional path from a Kansas farm to pastoring a small-town church, volunteering as an EMT, working with NASA through a defense contractor, and ultimately becoming CEO of Destin Dreamers. Before he was running a luxury vacation rental company on Florida's Emerald Coast, Arlen was hauling 500-pound rocks in a 1976 Jeep pickup to pay for college. It's an unlikely origin story but one that laid the foundation for everything he's built since.Packed with practical frameworks, hard-won wisdom, and what Annie coins "Arlenisms," this is the story of how grit, perspective, and a relationship-first philosophy built a standout brand in one of the most competitive vacation rental markets in the country.We cover:1️⃣ Why people do not buy stays, but experiences, outcomes, and peace of mind2️⃣ How calm leadership changes the way teams, guests, and owners respond under pressure3️⃣ Why simplifying operations is the real foundation for scalable growth4️⃣ How to identify owner fit and why saying no protects your team and your culture5️⃣ Practical frameworks for preventing issues and responding clearly when they arise6️⃣ How Destin Dreamers balances systems, structure, and human judgment7️⃣ Where AI fits in guest communication and where it should not8️⃣ What it means to lead in a competitive market without panic or burnoutConnect with Arlen:LinkedIn: https://www.linkedin.com/in/abflorida/Website:https://www.destindreamers.com/ Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.#vacationrentals #shorttermrentals #propertymanagement

Send us a message!In this unfiltered conversation, Sarah Bradford joins us once again to break down the most common and costly mistakes she sees vacation rental operators still making today.Drawing from more than two decades in the industry and her experience building, scaling, and ultimately selling two successful vacation rental companies, Sarah revisits pivotal moments that shaped her leadership, operations, and decision-making. This episode is practical, direct, and rooted in real situations. From financial missteps and weak owner communication to outdated technology, unhealthy competition mindsets, and tolerating the wrong homeowners, Sarah shares what she would fix immediately if she were starting again today.As the industry heads into 2026, this conversation offers a timely reality check on what needs to change and what operators can no longer afford to ignore.We cover:1️⃣ The financial habits that quietly put operators at risk2️⃣ Why trust accounting, budgeting, and clean books are non-negotiable3️⃣ Common owner relationship mistakes that lead to unnecessary churn4️⃣ How silence from homeowners can signal problems long before complaints5️⃣ Why competing on commission is rarely the right move6️⃣ The danger of delaying technology and PMS upgrades7️⃣ How weak company culture shows up in performance and retention8️⃣ When to say no to homeowners9️⃣ Why outdated homes hurt your brand more than you think🔟 What operators should fix now to stay competitive heading into 2026Connect with Sarah:LinkedIn: https://www.linkedin.com/in/sarah-bradford-032129b1/ Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.#vacationrentals #shorttermrentals #propertymanagement

Send us a message!This episode was recorded live at DARM 2025, right in the middle of the event, while the conversations were still unfolding and the energy was still fresh. Alex & Annie sit down for two fireside chats with Alex Cisneros (StayTerra) and Dennis Goedheid (Casiola) to talk through what’s showing up in the industry right now, and what operators are being asked to decide even when the path forward is not perfectly clear. If you were at DARM, this conversation will likely put words to what you were feeling. And if you weren’t, it offers a clear window into the discussions that mattered most this year.What you’ll hear in this episode:1️⃣ Why StayTerra targets reputable, community‑rooted operators2️⃣ Where centralization helps, and where local teams must stay empowered.3️⃣ Why multi-brand scale starts with getting data into one place4️⃣ Why loyalty is still tough to crack in vacation rentals.5️⃣ A more grounded take on luxury: less formality, more ease.6️⃣ How Casiola is building growth through partnerships and ambassadors.7️⃣ AI guest service that anticipates needs and raises expectations fast.8️⃣ The next challenge: being discovered when AI gives only a few options. Connect with Alex Cisneros:LinkedIn: https://www.linkedin.com/in/alexjcisneros/ Website: https://stayterravaca.com/ Connect with Dennis Goedheid:LinkedIn: https://www.linkedin.com/in/dennisgoedheid/ Website: https://www.casiola.com/ Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.#vacationrentals #shorttermrentals #DARM2025