Winner of The Shortyz 2026 Best Travel Influencers of the Year

Videos

June 4, 2026

How To Make Vacation Rental Marketing More Personal With AI

How To Make Vacation Rental Marketing More Personal With AI

Guest data is only valuable when it helps teams take action. For many vacation rental operators, the challenge is turning the data they already have into the right message for the right guest at the right time. In this clip, Orlie Benjamin shares how that workflow can become more streamlined…

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June 4, 2026

Live at Short Stay Summit 2026 | Hospitality Elevated: Where Tech and Human Connection Work together

Live at Short Stay Summit 2026 | Hospitality Elevated: Where Tech and Human Connection Work together
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June 3, 2026

From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki

From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki

The vacation rental industry has gone through major waves of change over the last two decades, and AI is quickly becoming one of the biggest shifts yet. In this episode, we welcome back John Suzuki, Chief Technology Evangelist at Staylist, for a conversation about the evolution of vacation rental technology,…

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June 3, 2026

From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki

From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki

The vacation rental industry has gone through major waves of change over the last two decades, and AI is quickly becoming one of the biggest shifts yet. In this episode, we are joined by John Suzuki, Chief Technology Evangelist at Staylist, for a conversation about the evolution of vacation rental…

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June 1, 2026

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Can we stop marketing properties and start marketing to people? That is the question at the center of Episode 2 of First of the Month Wrangle, brought to you by Lasoh. In this conversation, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to talk…

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June 1, 2026

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Turn every guest interaction into more revenue with Lasoh. Apply to become a Founding Member and/or get 20% off Lasoh products with code AlexandAnnie. Valid through July 31, 2026. 👉 Learn more: https://explore.lasoh.io/alex-annie In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are…

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June 1, 2026

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered. This…

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May 29, 2026

Are You Building a Business or Buying Market Share?

Are You Building a Business or Buying Market Share?

It is easy to look at a lower management fee as a way to stay competitive. But for vacation rental operators, the real question is not just whether the fee helps win the property. It is whether that fee can support the level of service the owner and guest expect…

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May 27, 2026

Why Invited Home Bet on Ski Markets Instead of Bigger Scale with CEO, James Smith

Why Invited Home Bet on Ski Markets Instead of Bigger Scale with CEO, James Smith

Growth is exciting, but in luxury vacation rentals, more does not always mean stronger. The real test is whether the business can keep delivering the level of service promised to owners and guests. In this episode, James Smith, CEO of Invited Home, joins Alex & Annie to talk about why…

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May 27, 2026

Why InvitedHome Bet on Ski Markets Instead of Bigger Scale with CEO James Smith

Why InvitedHome Bet on Ski Markets Instead of Bigger Scale with CEO James Smith

In this episode, we are joined by James Smith, CEO of InvitedHome, for a conversation about focused growth, luxury vacation rental operations, and what it takes to build a more sustainable business in high-end destinations. James shares how InvitedHome evolved from a broader multi-market vacation rental company into a luxury…

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May 26, 2026

Outsourcing Guest Support the Right Way

Outsourcing Guest Support the Right Way

Scaling guest support takes more than adding more people to the phone. The team representing your business needs to understand your standards, your properties, your guests, and the situations they may need to solve in real time. In this clip, Amanda Szubert shares how Call Center Solutions approaches that process,…

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May 22, 2026

AI Can Answer Questions, But Trust Takes People

AI Can Answer Questions, But Trust Takes People

AI has a place in guest communication, but the goal should be better hospitality, not less of it. In this episode, Paul Wohlford of Call Center Solutions shares why the future of guest support will likely be a hybrid model. AI can help teams move faster. It can answer common…

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May 20, 2026

Smarter Staffing, Stronger Service, Better Guest Experiences with Paul Wohlford and Amanda Szubert

Smarter Staffing, Stronger Service, Better Guest Experiences with Paul Wohlford and Amanda Szubert

Guest support is often treated as a back-office function, but every missed call, slow response, or poorly handled question can become a missed booking opportunity. In this episode, Paul Wohlford and Amanda Szubert of Call Center Solutions join Alex & Annie to talk about what vacation rental operators need to…

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May 20, 2026

Smarter Staffing, Stronger Service, Better Guest Experiences with Paul Wohlford and Amanda Szubert

Smarter Staffing, Stronger Service, Better Guest Experiences with Paul Wohlford and Amanda Szubert

In this episode, we are joined by Paul Wohlford and Amanda Szubert of Call Center Solutions to talk about staffing, guest services, AI, and the growing need for reliable support in vacation rental operations. Paul and Amanda share how Call Center Solutions grew out of a real hospitality staffing challenge…

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May 15, 2026

The Real Value of AI in Revenue Management

The Real Value of AI in Revenue Management

AI is becoming a practical advantage for vacation rental revenue teams. Property managers are working through shifting demand, owner expectations, pricing decisions, market data, and portfolio performance every day. The real challenge is turning all of that information into clear, confident action. In this clip from our first Revenue Reality…

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May 13, 2026

Direct Bookings Aren’t Dead, But Your Strategy Might Be | with Chris Walker of Direct Booking Tools

Direct Bookings Aren’t Dead, But Your Strategy Might Be | with Chris Walker of Direct Booking Tools

Getting guests to your website is only half the job. The bigger question is whether your website gives them enough clarity and confidence to take action. In this episode, we sit down with Chris Walker, Owner of Luxury Homes of Hilton Head and CEO of Direct Booking Tools, to talk…

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May 13, 2026

Direct Bookings Aren’t Dead, But Your Strategy Might Be | with Chris Walker of Direct Booking Tools

Direct Bookings Aren’t Dead, But Your Strategy Might Be | with Chris Walker of Direct Booking Tools

Many vacation rental operators are working to grow direct bookings, but the real opportunity is not just driving more traffic to their website. It is understanding what happens once guests get there. In this episode, we are joined by Chris Walker, Owner of Luxury Homes of Hilton Head and CEO…

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May 11, 2026

How AI Is Disrupting Hospitality Marketing

How AI Is Disrupting Hospitality Marketing

AI is changing the way travelers search, and hospitality brands are having to rethink what visibility really means. In this clip, Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide, shares why traditional digital marketing is being disrupted by AI, from SEO and keyword search to the way…

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May 8, 2026

Is PMS Only for Larger Operators?

Is PMS Only for Larger Operators?

Property management software is often seen as something operators adopt later, once the business is bigger or more established. In this clip, Pierre-Camille Hamana, founder and CEO of Hospitable, explains why the right tools should help operators get there sooner. For many smaller operators, the hesitation is understandable. Software can…

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May 6, 2026

How Marriott Vacations Worldwide Thinks About Loyalty with President, Mike Flaskey

How Marriott Vacations Worldwide Thinks About Loyalty with President, Mike Flaskey

Loyalty is not built through one booking. It is built through every touchpoint that gives guests and owners a reason to stay connected. In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide, for a conversation on how one of the biggest names…

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May 6, 2026

How Marriott Vacations Worldwide Thinks About Loyalty with President, Mike Flaskey

How Marriott Vacations Worldwide Thinks About Loyalty with President, Mike Flaskey

In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide. Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value. The conversation looks…

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May 5, 2026

How AI Supports Smarter Revenue Decisions

How AI Supports Smarter Revenue Decisions

Revenue management comes with a lot of moving pieces. Events shift demand, acing changes quickly, owner questions need clear answers, and sometimes, getting to that answer means digging through more dashboards than anyone would like to admit. In this clip from our first Revenue Reality Check episode presented by Beyond,…

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May 4, 2026

Why Are So Many Vacation Rentals Still Not Software Connected?

Why Are So Many Vacation Rentals Still Not Software Connected?

Why are so many vacation rental operators still managing without software? In this episode, Pierre-Camille Hamana, founder and CEO of Hospitable, shares why software adoption in the short-term rental industry still has a long way to go. Tools like CRMs, payroll systems, and accounting platforms are widely used by small…

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May 1, 2026

Introducing Revenue Reality Check Presented by Beyond, with CEO Julie Brinkman

Introducing Revenue Reality Check Presented by Beyond, with CEO Julie Brinkman

Revenue strategy does not happen on autopilot. Markets shift, booking windows move, owners ask harder questions, and guests become more price sensitive. For vacation rental managers, the strategy that worked last month may need a second look today. That is the focus of Revenue Reality Check, a 6-part bimonthly series…

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