Alex and Annie
326 episodes listed below
Vacation rental talk from inside the business.
Alex and Annie is an interview-led vacation rental show built around operators, software leaders, brand builders, and messy real-world stays. Its strongest episodes turn industry relationships into useful working knowledge about revenue, marketing, guest risk, loyalty, inventory, and local identity.
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Alex and Annie covers vacation rentals from the operator’s side of the desk. It is interview-driven, warm, and unusually embedded in the business relationships that make the industry move. The conversations often start with familiar rapport, then settle into detailed questions about growth, technology, guest behavior, owner expectations, and the realities of running properties at scale. That mix gives the show its texture. It can talk to Mike Flaskey about loyalty, regional training, and seasonal staffing without losing sight of the people who have to execute the plan in Hawaii, Orlando, Myrtle Beach, or Hilton Head. It can ask Julie Brinkman about revenue strategy and AI without turning the answer into buzzword theater. The useful question is usually practical: what does this mean for managers trying to keep pace with changing markets? Software episodes follow the same pattern. Pierre-Camille Hamana’s discussion of direct bookings, payments, insurance, guest verification, and chargeback risk becomes a plainspoken look at why building your own booking platform is harder than it sounds. Property episodes bring the business back to guest experience. The Vrbo Vacation Rentals of the Year conversation with Tim Rosolio spends time on seasons, lake houses, hot tubs, winter quiet, and technology that should feel intuitive rather than flashy. The show also makes room for the less polished side of hospitality. Pour Decisions turns property damage, claims, police involvement, and guest misconduct into operational lessons with a lighter tone. The first-of-the-month wrangle with Orlie Benjamin presses on marketing, revenue management, and the tension between growth-minded and operations-minded leadership. Awayday’s conversation with Jakob Dwyer adds another recurring concern: scaling a portfolio without bringing in the wrong inventory and damaging the brand. Tom Stewart’s Resort Realty episode grounds the discussion in legacy markets, direct booking strength, OTA overlap, and steady growth. Across episodes, Alex and Annie favor concrete stories over tidy slogans. The result is a show for people who already know vacation rentals are complicated and want smarter language for the problems they face every week.
Made for: For vacation rental property managers, owners, suppliers, revenue leaders, marketers, and operators who want candid industry conversations tied to daily decisions. It also suits hospitality people tracking software, channel strategy, guest risk, and portfolio growth.
What sets it apart: The show pairs friendly industry access with operator-level specificity, so major platform and business conversations keep returning to training, inventory quality, pricing, guest experience, and owner outcomes. Its recurring formats give serious business topics room for both tactical detail and lived-in stories.
With more than 35 years of combined experience in vacation rentals, Alex Husner and Annie Holcombe have teamed up to connect the dots between inspiration and opportunity, seeking to find the one story, idea, strategy or decision that led to their guests big A-HA moment. Join them, as they highlight the REAL stories behind the people and brands that have built vacation rentals into the 100 BILLION dollar industry it is today.
This is where chargebacks and balcony-launched furniture become your continuing education.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A focused revenue check in on the pressure, tools, and timing behind vacation rental pricing decisions.
Revenue strategy is the center of this episode, but the real pull is how closely it stays tied to the daily squeeze vacation rental managers feel: shifting booking windows, tougher owner conversations, and guests who watch price more closely than before.
Rob Walling on bootstrapped SaaS growth, plateaus, and exits — with founders who lived them.
Abbey Ashley's playbook for turning your job skills into a virtual assistant business.
Naval Ravikant on epistemology, startups, and crypto, from David Deutsch to Vitalik Buterin.
Alex Theuma interviews SaaS founders and investors on scaling to $10M-plus ARR.
Guy Raz traces founders' origin stories and fields live advice-line calls from entrepreneurs.
Alex Blumberg interviews guests like Megan Phelps-Roper and Shane McAnally about failure and reinvention.
Revenue strategy gets a gut check.
Hospitable founder and CEO Pierre-Camille Hamana explains how hosting 450 to 500 Airbnb guests in Brussels led him to build messaging automation in 2015.
Alex and Annie interview Tim Rosolio, Vrbo’s vice president of vacation partnerships, about selecting 80 Vacation Rentals of the Year from roughly two million properties across eight countries.
Alex Heuter and Annie Holcomb launch the Safely-presented series with Amanda Martins, Safely's vice president of business development, using guest damage claims to examine short-term-rental risk.
Jakob Dwyer, CEO of Awayday, tells Alex and Annie how RealJoy Vacations grew from zero to 1,200 properties in seven years and later merged with Villager Realty under private equity firm Light Bay.
Orly Benjamin, CEO of Lasso and a former marketer at American Airlines and Victoria's Secret, says PMS platforms handle only inventory, channel distribution and payments, leaving no single source of truth for guest contact data.
This episode features an interview with Sally Lockard from Hostiva discussing their partnership with BookingPal and strategies for expanding reach in the vacation rental industry.
Hosts Alex and Annie interview Tim Hubbard, CEO of Corsley, about his background in real estate and short-term rentals, and his current project building a boutique resort in Colombia.
Hosts Alex and Annie interview Jeff Hurst, CEO of Furnished Finder, about his career in the short-term rental industry and the company's role.
Hosts Alex and Annie discuss the vacation rental industry, featuring a sponsor segment about Nocturne Luxury Villas' acquisition model.
This episode features an interview with Scott Wiseman, discussing business growth and acquisitions in the vacation rental industry.
An interview with franchise owners discussing their experience and success with Grand Welcome in the vacation rental industry.
This episode features a testimonial from a vacation rental owner about how Track software improved her business operations and revenue.
A podcast about the vacation rental industry, featuring a sponsor testimonial on property management software Track.
An interview with Skyron's Senior Director of Location Support about their partnership with Marriott Homes and Villas and the benefits of working with professionally managed inventory.