The Short Term Show
8 Figure Airbnb and Short Term Rental Real Estate Investor Avery Carl 260 episodes Nov 11, 2026
The Short Term Show focuses on short-term rental (Airbnb) investing and management. Host Avery Carl interviews successful real estate investors and CEOs of Airbnb-related startups to deliver inspirational and actionable content. The show caters to both experienced Airbnb investors and those just starting out. Avery Carl has built a portfolio of over 250 doors and is the founder of The Short Term Shop, a leading Airbnb-specific real estate team.
Episodes
Free Property Management Software for DIY Landlords with Dave Spooner
Avery Carl sits down with Dave Spooner, co-founder of Innago, a free property management platform built for small and mid-size DIY landlords. Dave shares how he went from student-housing startup to landlord with 15 units in Cincinnati, how he handles short-term rentals in the same buildings as long-term tenants, and the three ingredients a market needs
Airbnb’s New Rules Could Leave Hosts Exposed with Katie Johnson
Avery is joined by Katie Johnson, an STR attorney, to break down Airbnb’s latest policy changes and what they could mean for short-term rental owners. Katie explains the potential impact of restrictions on rental agreements, guest ID verification, background checks, guest data collection, and enforceability of house rules, while highlighting legal excep
His Builder Went Bankrupt but His Rental Still Won with Nick Hausmann
On this week's episode, Avery is joined by Nick Hausmann, a short-term rental investor and co-host who built a vacation rental in Fort Morgan, Alabama, from 800 miles away. Nick shares the challenges of his first remote construction project, including a nine-month permitting process, his original builder going bankrupt, lost funds, and a project that st
Stop Chasing Tactics: Grow Your Direct Bookings with Chantell Hammond
On this week's episode, Avery is joined by Chantell Hammond, founder of Strategy Square, to discuss how short-term rental owners and property managers can grow their businesses through smarter marketing and direct booking strategies. Chantell explains why hosts should stop chasing every new social media trend, marketing tactic, or AI tool and instead lo
What It Really Takes to Finance an STR With an SBA Loan with Jamie Folk
On this week's episode, Avery is joined by Jamie Folk, a short-term rental investor who owns properties in New Jersey, Maine, and Orlando, Florida. Jamie shares how he acquired an established waterfront rental in Maine that grossed over $100,000 in his first six months of ownership, then purchased a nine-bedroom, themed Orlando vacation home for $980,00
Are You Actually Paying All Your STR Taxes? with Pam Knudsen
On this week's episode, Avery is joined by Pam Knudsen of Avalara to break down one of the least exciting but most important parts of running a short term rental: staying compliant with lodging and occupancy taxes. Pam explains why STR tax requirements can vary across states, counties, cities, and special jurisdictions, and why using Airbnb, Vrbo, or a
The Future of the Guest Experience Is Smarter Software with Margot Schmorak
Margot Schmorak, CEO and co-founder of Hostfully, joins the show to discuss how property management software is evolving and what hosts should look for when choosing a PMS. She covers Hostfully’s latest developments in home automation, damage protection, accounting, and AI-powered guest communication, including AI that can handle routine guest questions
Why Orlando STRs Are Not Oversaturated with Christian Walston
On this week's episode, Avery is joined by Christian Walston, an engineer and real estate investor who turned an accidental introduction to short term rentals into a successful investment in the Orlando market. Christian shares how he went from buying his first long term rental for just $33,000 to purchasing a seven-bedroom vacation rental near Disney,
The Overlooked Revenue Stream for STR Hosts with Ben Levy
Avery is joined by Ben Levy, co-founder and CEO of Localbird, to discuss how short term rental hosts can turn local experiences into an additional revenue stream. Ben shares how a frustrating vacation in Hawaii inspired him to build a concierge platform that makes everything from private chefs and massages to tours, transportation, and rentals easier fo
Why Melissa Nash Started Flipping STRs
Avery is joined by Melissa Nash, founder of Passively Rich with Rentals, to discuss how she built a portfolio of 20 rental properties after starting with just a $15,000 investment. Melissa shares how she uses short-term rentals to make markets like Southern California work, including buying properties that need some attention, turning them into profitab
Why Sedona Is a Missed Market with Leslie Carbajal
Avery is joined by Leslie Carbajal to explore three Arizona short-term rental markets: Sedona, Flagstaff, and Scottsdale. Leslie breaks down what makes Sedona such a compelling luxury market, including its iconic red rocks, strong tourism, limited pool inventory, and potential for higher revenue, while also explaining why Flagstaff offers a more afforda
100 Hours Could Change Your Taxes with Gian Pazzia
Avery is joined by Gian Pazzia, one of the founders of KBKG and a longtime expert in cost segregation, to break down how short term rental investors can use tax strategies to maximize depreciation deductions. Gian explains the difference between traditional depreciation and cost segregation, how the short term rental tax strategy can allow qualifying in
The Affordable Path to STR Investing with Mary Mueller
Avery is joined by Mary Mueller, a first-time short term rental investor who shares how she and her husband went from feeling priced out of vacation rentals to purchasing and renovating an affordable cabin in the Smoky Mountains. Mary explains how balancing homeschooling, raising three young children, and navigating family health challenges didn't stop
Building a Family STR Business from the Ground Up with Luke and Laura Hintermeister
On this week's episode, Avery is joined by Luke and Laura Hintermeister to share how their family's passion for renovation, hospitality, and outdoor adventure led them to purchase and transform a vacation rental overlooking Lake Superior. The couple explains how years of researching the North Shore market, finding an overlooked value-add property with i
The Design Decisions That Actually Increase Bookings with Courtney Petrovich
Avery is joined by Courtney Petrovich, founder of Denori Designs, to explore how thoughtful design can dramatically improve the performance of short term rentals and boutique hotels. Courtney shares how she transitioned from long-term rental investing into hospitality design after doubling the annual revenue of her own North Myrtle Beach vacation rental
Why Patience Beats FOMO in Real Estate with Lucas Papageorgiou
Avery is joined by Lucas Papageorgiou, a manufacturing consultant and real estate investor who shares how careful analysis, patience, and disciplined decision-making helped him build a portfolio of both long-term and short-term rentals. Lucas explains how purchasing a four-unit property at age 24 allowed him to live nearly rent-free while building equit
The Secret to Scroll-Stopping Listings with Tim Grillot
Avery Carl is joined by Tim Grillot, real estate investor and former Short Term Shop agent who has built a successful vacation rental photography business. Tim shares how his passion for photography evolved into a full-time career, explains why professional photography is one of the highest-return investments a host can make, and offers practical advice
Scaling Without Sacrificing Quality with Lindsey Pleasant
Avery is joined by Lindsey Pleasant, founder of Hostie Vacation Rentals, to discuss how she built one of the largest short term rental management companies in rural Texas by focusing on exceptional hospitality and operational excellence. Lindsey shares how she grew from managing a single property to more than 80 luxury vacation rentals across Round Top
The Underrated Mountain Market with Less Competition with Yok Re
Avery is joined by Yok to revisit the Blue Ridge, Georgia market and explain why it's one of the most overlooked opportunities for short-term rental investors. They discuss what continues to drive demand from Atlanta, Florida, and other nearby metro areas, why Blue Ridge offers less competition than the Smoky Mountains, and the types of cabins that perf
The Lake Michigan STR Strategy That Changed Everything with Jeremy Udovich
Avery is joined by Jeremy Udovich, founder of Sheboygan Vacation Rentals, to discuss how he went from a career in golf and software sales to building a thriving short-term rental portfolio and management company in Wisconsin. Jeremy shares how a single property near Lake Michigan grew into a portfolio of owned and managed vacation rentals, why Sheboygan
The Affordable Gulf Coast Market Most Investors Overlook with Kelsey Ardoin
On this week's episode, Avery is joined by Kelsey Ardoin to break down what’s working right now in the Galveston and Crystal Beach short-term rental market. Using one of her own properties as a case study, Kelsey shares how investors can dramatically improve bookings without spending tens of thousands on major renovations, focusing instead on guest expe
How Chris McKenna Built a 10-Property STR Portfolio and Retired in Just a Few Years
On this week's episode, Avery is joined by Chris McKenna, a former Fortune 500 executive who retired at 49 after building a portfolio of short-term rentals across Alabama, Oklahoma, and Maine. Chris shares how hearing Avery on a BiggerPockets podcast sparked his real estate journey, leading him from a demanding corporate career to owning multiple vacati
The “Regular Guy” Blueprint for Building Wealth with Short-Term Rentals with Lance Lalanne
On this week's episode, Avery is joined by Lance Lalanne, a Louisiana-based business executive and real estate investor who transformed his family's dream of owning a beach condo into a successful short-term rental business. Lance shares how a conversation with a friend, Avery’s audiobook, and guidance from the Short Term Shop team helped him confidentl
How a Bad Realtor Nearly Wrecked Their STR Dreams (And What They Did About It) with Erica and Jon Larson
Avery Carl sits down with Erica and Jon Larson, a former teacher and a VP of sales who turned a career shake-up into a thriving short‑term rental business. They share the real, often messy process of leaving their W‑2 jobs—starting with a tight budget, learning the hard way why you never skip a home inspection, and the nightmare of trusting a realtor wh
Negotiating Deals and Finding Hidden Value in Texas with Stacey Lancaster
Avery is joined by Short Term Shop agent Stacey Lancaster to explore the current state of short-term rental investing across Texas Hill Country and the Austin area. Stacey explains why the market currently favors investors who are willing to negotiate, create memorable guest experiences, and look beyond turnkey properties to add value through design and
Where and What to Buy in Southern Utah
Avery Carl is joined by Short Term Shop agent Cody Roberts to break down why Southern Utah has become an increasingly attractive short-term rental market. They discuss the tourism demand driven by Zion National Park and the surrounding outdoor attractions, the strict permit regulations that help prevent oversaturation, and the types of properties that p
What Actually Triggers an IRS Audit on Rentals ft. Ana Klein
On this week's episode, Avery is joined by Ana Klein, CEO of Tax Boss, to break down how short term rental tax law can help high income earners significantly reduce their taxable income. Ana explains how strategies like cost segregation and bonus depreciation can create large paper losses that offset W2 income, while emphasizing that these benefits only
The Asset Protection Hack That Stops Lawsuits Before They Start with Dohn Thornton
On this week’s episode, Avery is joined by Dohn Thornton, a seasoned real estate investor and short sale expert who has flipped over 3,000 properties and now focuses on advanced asset protection strategies. Dohn breaks down the concept of a spendthrift trust, explaining how it differs from traditional LLCs and trusts by offering greater privacy, lawsuit
A New Way for Property Managers to Get Clients ft. Emily Tunggala
On this week’s episode, Avery is joined by Emily Tunggala. Emily shares how Hospitable is expanding beyond traditional property management software by launching a marketplace that connects property managers with owners looking for help. She explains how the platform uses performance data and insights to match the right managers with the right properties
Tax Savings Won’t Save a Bad Deal with Brian Boyd
On this week’s episode, Avery is joined by Brian Boyd. Brian, a tax attorney and real estate investor, breaks down how the short term rental tax strategy works, explaining how investors can use cost segregation and bonus depreciation to offset active income while building wealth. He emphasizes the importance of self-managing properties, tracking time ac
The Real Chaos Behind Setting Up STRs ft. Kim Fitzpatrick
On this week’s episode, Avery is joined by Kim Fitzpatrick. Kim shares how she went from being a PE teacher and single mom to launching her first Airbnb with an air mattress, eventually scaling into multiple investment properties across markets like the Smokies and Montana. She breaks down how her hands-on experience renovating and setting up properties
The Biggest Due Diligence Mistakes Killing Your Deals with Ari Rastegar
On this week’s episode, Avery is joined by Ari Rastagar. Ari shares how he built a multibillion-dollar real estate firm starting with just $3,500 and explains why real estate is far more operationally complex than most beginners expect. He dives into the importance of risk management, due diligence, and local market expertise, highlighting common mistak
How to Win in Broken Bow Without Overspending ft. Cathy Craig
On this week’s episode, Avery is joined by Cathy Craig, a top agent and investor in Broken Bow, Oklahoma, who shares an inside look at the current market and why now may be a prime time to buy. She explains how prices have come down significantly from peak levels while demand and occupancy remain strong, pushing back on the idea of “oversaturation” and
How to Protect Your Short Term Rental From Lawsuits ft. Katie Johnson
Avery is joined by Katie Johnson, a short-term rental attorney and investor who breaks down the most common legal mistakes hosts make and how to avoid them. She explains key risks like missing deed restrictions, improperly handling LLCs, and failing to secure adequate insurance, along with how to protect yourself from lawsuits tied to pools, amenities,
Turning Construction Skills Into Short-Term Rental Cash Flow ft. Robert Warren
On this week’s episode, Avery is joined by Robert Warren, a real estate investor who shares how decades of experience in building, rehabbing, and developing led him to short-term rentals. He breaks down how he transitioned from long-term rentals and flips into STRs, including buying and optimizing properties in Gulf Shores and the Smokies for stronger c
How Backyard Amenities Turned One STR into a $217K Performer with John and Christina McNaught
On this week's episode, Avery is joined by John and Christina McNaught. The couple shares how they transitioned from long-term rentals into short-term rentals after realizing a small Airbnb unit on their property could cover their mortgage and generate additional cash flow. They discuss investing in the Bradenton, Florida market, including seasonality p
Why Condos Dominate the Branson Vacation Rental Market with David Taylor
On this week’s episode, Avery is joined by David Taylor. David shares how he transitioned from construction and home inspecting into short term rental investing, ultimately choosing Branson, Missouri for its affordability and strong 10-month tourism season. He breaks down purchasing a brand-new three-bedroom condo for $225,000 and generating nearly $53,
Smart STR Upgrades That Actually Increase ROI with Celeste DiRocco and Philip Pane
On this week's episode, Avery is joined by Celeste DiRocco and Philip Pane of Parklin Interiors. They share how they went from buying their first short term rental sight unseen in Gatlinburg to building a six property portfolio across Tennessee, North Carolina, Georgia, and Virginia while designing more than 200 short term rentals nationwide. Celeste ex
Amenity Stacking, Snowstorms and Scaling STRs in New York ft. Josh Briner
On this week's episode, Avery is joined by Josh Briner. Josh shares how he transitioned from a background in education and flipping distressed properties into building a short term rental portfolio in upstate New York, including the Finger Lakes and Buffalo area. He dives into why he prefers value-add BRRRR deals over turnkey properties, how amenity st
Investor Partnerships That Actually Work with Aubrey Carlson
On this week's episode, Avery is joined by Aubrey Carlson, owner of Salt and Sky Lodging Company and a former military helicopter pilot, to talk about building a short-term rental portfolio in both San Diego and Birmingham, Alabama. Aubrey shares how she used a VA loan and a house-hack-style fixer strategy to break into an expensive coastal market, then
Why Passion-Driven Investing Wins in Short Term Rentals with Matt Holmes
On this week's episode, Avery is joined by Matt Holmes of Get Up North Retreats to explore building a short-term rental business rooted in passion, relationships, and outdoor hospitality. Matt shares how his love of fishing, hunting, and family time led him to pivot from land and off-lake cabins into lakefront rentals—and ultimately into owning and oper
Stabilization, Not Saturation: The Truth About STR Performance ft. Kenny Bedwell
On this week’s episode, Avery is joined by Kenny Bedwell to break down what the short-term rental data actually says about the past few years and what investors should realistically expect heading into 2026. They discuss why the industry is experiencing stabilization rather than collapse, how average revenue declines are masking strong performance among
The Credit Card Strategy Most Real Estate Investors Miss with Ross Alcorn
On this week's episode, Avery is joined by Ross Alcorn, founder of Itinerary Boss, to break down how real estate investors can use credit card strategy to turn everyday spend into serious travel rewards or bottom-line value. Ross shares how his background in sales, real estate investing, and trip planning led him to uncover powerful points strategies—fr
Why Last-Minute Bookings Are Reshaping Vacation Rental Strategy with Stacey St. John
On this week’s episode, Avery is joined by Stacey St. John to dig into what’s really happening in today’s short-term rental market, with a particular focus on Myrtle Beach. They discuss how travel behavior has shifted toward more last-minute bookings, why pricing and revenue management matter more than ever, and how investors should think about buying o
Building a Profitable STR Without Hot Tubs or Luxury Finishes with Kira D’Annunzio
On this week's episode, Avery is joined by Kira D’Annunzio to share how she built a highly successful Poconos short-term rental by leaning into branding, storytelling, and knowing her exact guest avatar. Kira walks through her journey from repeated career layoffs to financial independence through real estate, explaining how she used equity, off-market d
Why 2026 Needs to Be Boring for STR Investors with Luke Carl
On this week's episode, Avery is joined by her husband Luke for a candid end-of-year wrap-up on what actually happened in short-term rentals and real estate in 2025—and what fundamentals will matter most going into 2026. They dig into why the market finally feels “boring” again (and why that’s a good thing), how low transaction volume means we’ve effect
Why the Housing Crash Might Already Be Here with Chuck Kramer
On this week's episode, Avery is joined by Chuck Kramer to break down what it could mean if the Fed is truly winding down quantitative tightening and moving toward quantitative easing. They explain (in plain English) how increasing bank reserves and buying Treasuries/mortgage-backed securities can loosen credit conditions and potentially help bring borr
Elevating Guest Experience Through Tech and Design ft. Joe Young
On this week's episode, Avery is joined by Joe Young, an Austin-based luxury short-term rental operator and co-founder of SPRKhost. Joe shares how he and his wife began with a Lake Travis vacation home in 2017 and ultimately turned their primary residence into a single property grossing nearly $500,000 a year. He breaks down how they expanded to managin
Why Naomi Brown Chose a Giant Shoe Over a Normal Rental
On this week's episode, Avery is joined by Naomi Brown, a commercial real estate agent and owner of the iconic Hanes Shoe House in York, Pennsylvania. She shares the wild backstory of the three-bedroom, shoe-shaped home that was originally built in 1950 as a marketing stunt for a local shoe store and how she transformed it from an ice cream shop into a
Inside the Mind of a Revenue Management Pro with Jake Cohen
On this week’s episode, Avery is joined by Jake Cohen, hospitality veteran and founder of Step by Step BNB. Jake grew up running a family bed and breakfast in Lake Tahoe, learned the art of pricing while managing boutique hotels, and eventually built a portfolio of short term rentals before launching his own revenue management company. He and Avery dig
Authentic Growth and Direct Bookings through Social Media with Brittany Magsig
On this week's episode, Avery is joined by Brittany Magsig, the social worker turned short-term rental investor and content creator behind Mountain Mama Cabins. Brittany shares how motherhood, a pandemic trip to the Smoky Mountains, and a desire for freedom inspired her to pivot from education into real estate investing. She opens up about buying her fi
Other People’s Everything: Scaling Your STR Empire Without Burnout with Bethany LaFlam
On this week's episode, Avery is joined by Bethany LaFlam, a “recovering attorney,” community architect, and author of The Power of OPE. Bethany and Avery dive into what it really means to stay in your lane, leveraging “other people’s everything” (money, time, assets, skills) so you can scale without burning out. They break down how to safely and legal
The Guest Experience That Drives 5-Star Reviews with Frank Napolitano
On this week's episode, Avery is joined by Frank Napolitano. Frank shares how he and his family transitioned into short-term rentals in the Smokies, leveraging bonus depreciation and cost segregation to maximize tax advantages. He discusses what makes their property stand out—like a pool, tiki bar, and ADA accessibility—and how small touches such as hol
Stop the Scroll: $20–60k Makeovers That Double Revenue ft. Joe DelGrosso
On this week's episode, Avery is joined by Joe DelGrosso. Joe shares his journey from working in TV production to owning short-term rentals and why his first Smokies cabin proved that thoughtful refreshes can outperform flashy, high-cost amenities. He explains his boutique management approach at Southern Sons Hospitality, focusing on capped inventory, s
The New PriceLabs Features Every STR Owner Should Try with Thibault Masson
On this week’s episode, Avery is joined by Thibault Masson, Head of Product Marketing at PriceLabs. They unpack Booking.com’s challenges in the U.S. versus Europe and how Airbnb’s fee changes are reshaping the playing field, before diving into PriceLabs updates like Dynamic Minimum Stay, the new Listing Optimizer, and a free revenue-management course. A
Insurance Lessons Every STR Investor Must Hear with Toni Boer
On this week’s episode, Avery is joined by Toni Boer. Toni shares how she and her husband turned a $200k family getaway into a cash-flowing STR, eventually building an eight-property portfolio along Kentucky’s Bourbon Trail plus a new Florida beach house. She opens up about losing a riverfront property to a historic flood, the hard lessons she learned a
From Caregiver to Condo Investor with Tamara Brown
On this week’s episode, Avery is joined by Tamara Brown. Tamara shares how she stumbled into real estate while caring for her grandparents, turning multiple family homes into rentals before purchasing her first STR in Destin, Florida. She explains how she analyzed her numbers, leaned on mentorship, and embraced the “enemy method” to size up competition.
The Truth About Buying “Ugly” Cabins That Cash Flow with Amy Morehead
On this week’s episode, Avery is joined by Amy Morehead. Amy shares how turning a family chalet in the Smokies into an STR during her mother’s Alzheimer’s caregiving season sparked a value-add strategy focused on “hot-mess” properties, smart renovations, and self-management. She explains why high-impact finishes beat flashy amenities for appraisal value
How HelloHost AI Levels Up Your Hosting with Annie Li
On this week’s episode, Avery is joined by Annie Lee to dig into Hello Host, an AI “autopilot” for guest communications that plugs into PMS tools like Guesty, Hostaway, and Hospitable. They discuss how it learns from past conversations and listing data, makes judgment calls on escalations, and pings hosts when a human decision’s needed. Annie shares whe
The Truth About Material Participation Rules with Karlton Dennis
On this week’s episode of The Short Term Show, Avery interviews Karlton Dennis. The two dig into how the short-term rental tax strategy actually works today, including what “material participation” really means in an audit. They cover using cost segregation and (current) bonus depreciation to create paper losses, the do’s and don’ts of hour-tracking, an
Why Hosting 30 Guests at Once Can Be Easier Than Hosting 2 with Andrew Llewellyn
On this week’s episode, Avery is joined by Andrew Llewellyn to unpack how he built a thriving short-term rental business in Louisville, KY. He shares the pivot from an almost-bakery to 10–30 guest stays, the data-driven playbook behind tiered calendar openings and last-minute pricing using throughput accounting, and why in-house cleaning and EOS/Tractio
What Falling Rates Mean for Real Estate Investors with Brenna Carles
On this week’s episode of The Short Term Show, Avery interviews Brenna Carles. They unpack what Powell’s recent signaling means for mortgages, why lenders “pre-price” ahead of Fed meetings, and how the 10-year Treasury, inflation, jobless claims, and non-farm payrolls flow through to rate sheets. Brenna shares where DSCR and conventional rates are landi
From Data to Deals: How to Pick Winning STR Markets Faster with Jae Seok An
On this week's episode, Avery is joined by Jae Seok An, founder of Airbtics, to dig into smarter market selection and the realities of STR data. They walk through Airbtics’ draw-your-own-market mapping, listing density by bedroom count, and the Market Explorer—tools aimed at helping newer investors compare many locations, budgets, and regulation profile
Turning Short‑Term Rentals into a Bigger Hospitality Business with Rashmi Bhat
On this week’s episode, Avery is joined by Rashmi Bhat. Rashmi shares how she went from opening a restaurant at 21 to falling in love with Airbnbs, quickly building a multi‑market STR portfolio and scaling management in the Texas Hill Country to dozens of units through systems and a VA team. She and Avery dig into why the Hill Country still has room for
Special Episode: A deep dive to PriceLabs with Wayde Hall
On this week's episode, Avery is joined by Wayde Hall from the Short Term Shop for a hands-on walkthrough of how he uses Price Labs Market Dashboards to analyze properties in detail. Wayde demonstrates step-by-step how to filter for specific property types, review counts, and amenities, then sort by revenue to identify top performers and pinpoint areas
Wayde Hall’s Secrets to Spotting Winning Short-Term Rentals
On this week's episode, Avery is joined by Wayde Hall, a Short Term Shop agent in the Smoky Mountains, to dive into how he uses Price Labs Market Dashboards for short-term rental analysis. Wayde explains how this tool offers highly granular data—like occupancy rates, cleaning fees, and guest capacity—allowing investors to spot performance patterns rathe
Bobby Birch’s $98K First Year in a “Saturated” Market
On this week’s episode, Avery is joined by Bobby Birch, a new investor who’s crushing it with his very first short-term rental in the Smoky Mountains. Bobby shares how he and his wife bought a one-bedroom cabin in late 2023—at the peak of interest rates—and still grossed $98K in their first ten and a half months. He breaks down how thoughtful amenities,
Running STRs from Anywhere: Adrienne Green’s Full-Time Travel Lifestyle
On this week’s episode, Avery is joined by Adrienne Green, a real estate investor, former teacher, and full-time world traveler who built a self-sufficient short-term rental business with the help of virtual assistants and great systems. Adrienne shares how she went from house hacking her basement to building a portfolio of long- and short-term rentals
How to Time Your STR Strategy for Maximum Tax Savings with Barbara Schreihans
On this week’s episode, Avery is joined by Barbara Schreihans, founder of Your Tax Coach, to dive into the powerful intersection of real estate investing and tax strategy. Barbara shares her insights on how short-term and mid-term rentals can be leveraged strategically depending on your income year, explaining how to maximize the short-term rental looph
Why Branding, Bedrooms, and Buying Off-Market Are Chad Gallagher’s Secret Weapons
On this week’s episode, Avery is joined by Chad Gallagher, a tech-turned-real-estate entrepreneur who’s built and sold a 5,000-door property management company, owns over 200 long-term rentals, and now focuses on acquiring what he calls "iconic" short-term rental properties. Chad shares the details behind his high-end STR portfolio—including a 9-bedroom
Jane Ng’s Path to Financial Freedom with STRs and Co-Hosting
On this week's episode, Avery is joined by Jane Ng, a Bay Area-based investor who pivoted into real estate after her daughter's health challenges made traditional work unsustainable. Jane shares how she grew her portfolio to include long-term rentals in Arkansas, four profitable short-term rentals in California, and ten co-hosted properties—all while ra
Crushing It with Condos: Tammy's $200K Year in PCB Rentals
On this week's episode, Avery is joined by Tammy Gibbons, who shares how she and her husband transformed their 120-acre Wisconsin family farm into a thriving short-term rental business through a 1031 exchange. Tammy discusses how they landed on Panama City Beach as their market, the decision to self-manage while balancing full-time careers and parenting
Poker Sheds and Above-Ground Pools: Unconventional Wins in STR Investing with Taylor Jolly
On this week’s episode, Avery is joined by Taylor Jolly, founder of Roam Free Vacation Home Rentals, to discuss how he transitioned from construction project management to profitable real estate investing. Taylor shares how he’s made co-living and large short-term rentals cash flow in expensive markets like Austin, leveraging creative strategies like ha
Depreciation, Documentation, and Dodging Mistakes with Brandon Hall and Nathan Sosa
On this week’s episode, Avery is joined by Brandon Hall and Nathan Sosa of Hall CPA to dive deep into the short-term rental tax loophole and how investors can legitimately use it to offset W2 and business income. They discuss the origins of the loophole, how to qualify through material participation tests, and what documentation is necessary to survive
Why Every Short-Term Rental Investor Needs a Tax Strategy with Yonah Weiss
On this week's episode, Avery is joined by Yonah Weiss, an expert on cost segregation and a favorite among real estate investors. They break down what a cost segregation study is, how it allows short-term rental owners to accelerate depreciation and save on taxes, and who qualifies to benefit from this strategy. Yonah explains how to navigate bonus depr
From Abandoned Campground to $7.8M Glamping Empire with Heather Meuer
On this week's episode, Avery is joined by Heather Meuer, a Missouri-based real estate investor who transitioned from running an auto parts business to building and managing RV parks and glamping resorts. Heather shares how she and her husband turned an abandoned campground into a thriving $7.8M resort in Branson, complete with glamping tents, RV pads,
How Melissa & Chris Jones Turned a “Turnkey” Nightmare into a Thriving STR Portfolio
On this week's episode, Avery is joined by Melissa and Chris Jones, a dynamic investor duo who share how a simple desire for a second home evolved into a thriving short-term rental business and boutique co-hosting company. They walk through their journey from renovating a “turnkey” townhome in Galveston to scaling up with high-performing properties in B
How Nathan St. Cyr Turned an $821K Hostel into a $5.2M Hospitality Powerhouse
On this week’s episode, Avery is joined by Nathan St. Cyr, a hospitality innovator who’s redefining budget travel through upscale hostels. Nathan shares how he stumbled into the hostel space in Maui and turned a $821K property into a $5.2M valuation in just 18 months—all while achieving over $824K in annual NOI. He breaks down the operational and financ
How Isaac French Built a Viral Cabin Camp—and Sold It for Millions
On this week’s episode, Avery is joined by Isaac French, a creative powerhouse who went from bookkeeper to hospitality developer and Instagram sensation. Isaac shares the remarkable journey behind Live Oak Lake, a Nordic-inspired micro resort he designed and built from scratch in Texas—achieving 95% occupancy in year one and ultimately selling to an ins
Why Your Evenings and Weekends are the Secret to Real Estate Success with Matt Krueger
On this week's episode, Avery is joined by Matt Krueger. Matt shares his journey from working dead-end jobs to becoming a full-time real estate investor with a portfolio of 11 properties across Iowa. He dives into his strategies for blending long-term and short-term rentals, financing deals creatively with home equity lines of credit, and how local mark
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