The Short Term Show

This week, Avery interviews Kassidy Warren, who shares his journey of leaving the corporate world to pursue full-time short-term rentals and van life. Kassidy discusses his background growing up frugal, his transition from an engineering career in the corporate world, to his burnout and desire for a change in direction. Kassidy detailed his initial foray into real estate investing, highlighting hi...

In this episode of the Short Term Show, CPA Ryan Bakey shares his experience defending and winning an audit on the STR tax loophole. Ryan emphasized the importance of having a CPA who specializes in real estate and understands the intricacies of the tax laws related to short-term rentals. They also discussed how critical it is to maintain meticulous records, financial statements, and documentation...

In this episode, Avery had the pleasure of speaking with Jen Dickson, a seasoned short-term rental investor who has successfully navigated multiple markets. Jen detailed their strategic approach to selecting markets, emphasizing the importance of choosing locations they personally enjoy and frequent. They also delved into the financial aspects of their investments. They also discussed the challeng...

In this episode of the Short Term Show, Avery interviews  Adam Czajkowski.  Adam shares his unconventional journey into real estate, starting from a background in baseball to working for the New York Yankees, and eventually transitioning to sales to gain back time and financial stability. They delved into the challenges of finding deals, especially in untapped markets, and the importance of having...

In this episode, Avery had the pleasure of speaking with Bethany LaFlam, the managing partner of Premier Law Group. Bethany shared her extensive knowledge as a securities lawyer, explaining the intricacies of syndications and joint ventures, particularly in the context of short-term rentals. She highlighted the importance of compliance with SEC regulations and provided practical advice on how to a...

This week Avery is joined by Lauren Cecil, an innovative entrepreneur who has successfully transformed her property in West Texas into a multi-faceted business. She shares her journey of transforming her inherited property into a thriving business that includes a campground, a luxury short-term rental, and a Jeep rental service. She talks about the challenges and rewards of managing a remote prope...

This week Avery is joined by Jayla Siciliano, CEO of Atlas Vacations and host of the Seed Money podcast, who shares her experience appearing on Shark Tank in season five. She describes the behind the scenes of Shark Tank and the lasting impact of the exposure gained from the show. Jayla also shared the story of how her foray into real estate began somewhat accidentally, and how that led to her sta...

In this episode, host Avery Carl interviews Ishita and Harshad Lalan, the founders and owners of Ishita Interiors. The couple shares their journey into the world of STRs as investors and how their background in design and engineering has shaped their success in the industry. Ishita and Harshad discuss their unique approach to STR design, focusing on a strategic design formula that includes market...

On this episode, Avery is joined by Neighbor CEO and founder Joseph Woodbury. Joseph shares how Neighbor provides a unique opportunity to maximize income from short term and long term rentals. Joseph also addresses common concerns, such as the types of items allowed and the security measures in place to ensure high-quality renters. He emphasizes the community-building aspect of Neighbor, where loc...

This week Avery is joined by Jim Sheils, real estate investor who specializes in the build-to-rent model. They discuss the advantages of Build-to-Rent, emphasizing its efficiency in reducing maintenance costs and increasing tenant retention compared to older properties. Jim highlights the importance of starting small, and the necessity of understanding the complexities involved in new construction...

In this episode, Avery sits down with AJ Osborne, a self-storage investing mogul and the founder of Cedar Creek Capital. AJ shared his incredible journey from insurance sales to becoming a leading figure in the self-storage industry, and how this asset class played a crucial role during a life-altering personal crisis.  AJ emphasizes the concept of having a "margin of stupidity," as they discuss t...

In this episode, Avery is joined by Craig Curelop to talk about the house hacking strategy and how it can change the tragectory of your life. They discuss the different approaches to househacking, how fluctuating interest rates have impacted house hacking, the most ideal markets for house hacking and more.    How to connect with Craig: https://www.thefiteam.com/ https://invest2fi.com/   @thefiguy,...

In this episode, Avery is joined by guest Bryan Cataldi for a follow-up on his journey of rehabbing a seven-cabin development in the Smokey Mountains. Brian shares his experiences from the project, highlighting the hard work and dedication required in the short term rental business. They discuss some impressive rental stats, his rehabbing strategy for this development, why he prefers one bedroom p...

In this episode, Avery sits down with Philip Kennard, the founder of FutureStay, a property management operating system designed for the modern rentalpreneur. Philip shares his journey from a tech-savvy teenager to a successful entrepreneur who stumbled into the short-term rental industry by necessity. He emphasizes the importance of building the right habits and strategies for success in the shor...

In this episode, Avery interviews Angel Piontek, the head of marketing at Point Central, a smart home technology company. They discuss various smart devices for short-term rentals, including smart locks, smart thermostats, and a few you might not have considered before, such as water sensors, door and window sensors, and smart noise monitors. Angel highlights the benefits of using smart property t...

In this week's episode, Jamil Damji joins Avery to share his journey of self-teaching in real estate wholesaling for over 20 years and how it has shaped his unique approach to the business. They discuss the importance of ethics in real estate as well as the importance of relationships. Jamil shares his extensive experience in real estate wholesaling, offering valuable insights and advice for both...

In this episode, Jamie Lane from AirDNA joins Avery to discuss the recent changes in AirDNA's interface and pricing. Jamie shares insights on how AirDNA tracks short-term rental data worldwide, providing insights on revenue, occupancy, amenities, and more. He highlights the significance of local expertise, as well as the importance of understanding market scores, amenities, and bedroom counts when...

In this episode, Lisa Chastain joins the Avery to delve into personal finance and building healthy relationships with money. Lisa emphasizes her mission to empower women to become financial powerhouses by developing a healthy relationship with money and debt. Their conversation emphasizes the need for clarity, mindset shifts, and practical systems to achieve financial success.   How to connect wit...

This week Avery is joined by two Short Term Shop agents in the Sarasota and Bradenton area, John and Christina McNaught. They go through a brief overview of owning properties in this market, such as what the seasonality is like, what types of properties perform best, why it's crucial to have an agent who is familiar with the area and more.    Check out our 10 episode deep dive on the Sarasota/Brad...

This week Avery is joined by MyOutDesk CEO, Daniel Ramsey. They discuss the relevance of virtual assistants in the short term rental industry, emphasizing the non-stop nature of this business and the need for support that can handle tasks at any hour. They also discuss the benefits of having a virtual assistant and touch on why delegation is crucial for business growth.                How to conne...

This week Avery is joined by franchising expert, Jon Ostenson. They discuss the similarities between real estate investing and franchising, such as building cash flows, enjoying tax benefits, and creating long-term assets. John points out that many real estate investors are turning to franchises to diversify their portfolios, especially in the current market. John also highlights the advantages of...

This week Avery is joined by Sabrina Guler, Techvestor COO and Co-founder. Avery and Sabrina highlight the misconception that the short-term rental business is a passive investment. They also emphasize the importance of making the right investment decisions upfront, such as choosing the right property and considering renovations and amenities. Sabrina also shares how Techvestor goes about choosing...

In this episode of The Short Term Show, the host welcomes Brad Baldridge, a financial advisor specializing in college planning. Brad shares his insights and strategies for navigating the increasingly expensive world of college education, such as putting your kids on payroll. They also discuss the challenges families face and the need for proper planning to minimize costs.   How to connect with Bra...

In this episode, Avery is joined by Shawn Moore, a seasoned investor in the vacation rental industry. Sean has been investing in real estate for over 24 years and has a wealth of experience in the vacation rental space. They discussed the importance of choosing the right market for vacation rentals and how it can greatly impact the success of your investment. Shawn emphasized the need to understan...

In today's episode, Avery has the pleasure of speaking with Ricky Carruth, a seasoned real estate professional with over 20 years of experience in the industry. They delved into the importance of having a backup plan when investing, learning from Ricky's own experience of losing everything in the 2008 crash. Ricky provided insights on current market trends and offered his perspective on where the...