Short Term Rental Success Stories

I had the honor of speaking with Steve Milo, founder and CEO of Vtrips, a full service vacation rental management company with over 1500 properties throughout the U.S. In this episode, Steve shares his journey from 0 to 1500 properties, how he grew his team, the strategy to increasing direct bookings, how Steve prices his properties, and the impact of advocacy on vacation and urban short term rental markets.

I had the honor of speaking with Zac Rushton, co-owner of Great Dwellings, a short term rental management company based in DC. Great Dwellings has 80 managed and 10 master leases. In this episode, Zac shares his experience of joining Great Dwellings when they had 20 properties and stuck being unable to grow, and how by joining their team they were able to take on an additional 80 properties in a few short years.

I had the honor of speaking with Darik Eaton, founder of Seattle Oasis Vacations, a management company that operates 30 units in the Seattle Washington area. Darik's portfolio currently consists of 28 managed and 2 master lease. In this episode, Darik shares his journey of starting his short term rental business using Craigslist, his battle and the outcome of fighting a condo association on their regulations, how he grew his portfolio inside of condos and HOAs, how he helped stop the city of Seattle from enforcing even stricter regulations, and much more.

I had the honor of speaking with Alice Horn, CEO of My Villa Key, a vacation rental management company in the Orlando Florida area. My Villa Key has 80 properties under management. In this episode, Alice shares her journey and struggles of entrepreneurship when starting a company, how she positions her management company to help children on the autism spectrum and other development disabilities, and how she has been able to compete in the highly competitive Orlando market.

Today I had the pleasure of speaking with Ray Licardo. Ray is a short term rental operator based in the San Jose area. Ray has 10 total properties under management, 6 of them being master lease and 4 cohosted. In this episode, Ray shares his experience quitting his sales job to pursue short term rentals full time, how Ray pivoted his business to cater towards corporate rentals, and how he has been able to create a profitable business netting $700 - $1000 per property by only doing monthly rentals.

Today I had the honor of speaking with Jennifer Frankenstein-Harris, CEO and founder of Great Ocean Condos, a vacation rental management company located in New Smyrna Beach, FL. Jennifer's company has grown to 265 rentals since 2008 and is grossing $6 million a year. In this episode, Jennifer shares her experience of falling into vacation rental management, what it was like to scale, the obstacles along the way, and her unique approach to growing her management company.

I had the special honor of speaking with TJ Tijani. TJ is a BRRRR investor and a STR manager based out of Houston area who has 14 units total, 7 which are owned and 7 master leased. In this episode, TJ shares his journey of BRRRR investing to master lease investing, how to stand out in a crowded market, and the costs associated with buy and hold investing vs master lease.

In this episode, I have the special honor of speaking with Andrew LeBaron, founder of Buymoretime.com, a management service that charges as low as $99 a month for short term rentals as opposed to a revenue share model. In this episode, Andrew shares how he is able to keep costs so low for his services, his unique way of automating the business, his process for streamlining client onboarding, and how he has been able to outsource everything to virtual assistants.

I had the special honor of speaking with Tom and Sofia Sharkey. Tom and Sofia are the owners of Lemon Tree BnB, a short term rental management company in Kansas City, MO. Tom and Sofia got started after buying their first personal home in a trendy area of town in 2018 which was quickly turned into their first STR. A year later they got their second property in the same neighborhood using the rental arbitrage strategy. Tom left his speech therapy career to pursue his dream of building wealth through real estate and a short term rentals. Over a six month period their STR portfolio expanded from two to twelve listings using diverse strategies of buy and hold, partnering, rental arbitrage, and management. In this episode, Tom and Sofia share their journey on starting and then scaling to 12 units in a six month period, their unique strategy to finding true value add rental arbitrage properties, and how they have been able to scale through investor partners.

I had the special honor of speaking with Rich Munroe, founder of Diamond Edge Properties, a tax lien real estate investment company that has shifted it's focus to primarily short term rental management and master lease investing in the Atlanta, Georgia area. In this episode, Rich shares his experience of starting his real estate flipping company, how tax lien investing works, why the switch to focus on short term rental management, and why Rich's strategy involves acquiring the largest properties in the area to master lease.

Today I had the honor of speaking with Anurag Verma, the Co-founder of Pricelabs. Pricelabs is a dynamic pricing tool for professional short term rental operators helping over 3,000 properties around the world maximize their Airbnb income. In this episode, Anurag shares his backstory on starting Pricelabs, how dynamic pricing works, different markets and how they are responding, and how to analyze a market to see how it is recovering.

Today I had the honor of speaking with Mark Simpson, founder of Boostly.co.uk, the 'one-stop-shop' to helping you get direct bookings through website building and education. In this episode, Mark shares the most important aspects of increasing direct bookings and how to drive more traffic to your business.

I had the special honor of speaking with James Burrows, one of the co-founders of Rentals United, a channel manager that helps property management companies market their listings across 60+ channel partners. In this video, James explains the difference between channel management and PMS, how Rentals United was formed, and the importance of channel diversification.

I had the honor of speaking with Peter Plourde, owner of North Conway Property Management. Peter has 2 properties that he owns and 8 properties that he cohosts all in the White Mountains of New Hampshire. Peter started his property management business and in one month scaled from 2 properties that he owned/managed to now cohosting 8 properties.  In this episode, Peter shares his story of how he first got into short term rentals and how he has been able to scale to managing other people's properties during Covid-19. 

I had the honor of speaking with Brian Tibbs, the owner and CEO of “My Short Term Home,” located in Meridian and Boise, Idaho.   In this episode, Brian shares how he's been able to acquire 19 rentals through buy and holding investing, how he manages properties while living in South America, and how he has been able to survive the covid-19 pandemic. 

In this episode, I had the special honor of speaking with Anthony Keen who is based in Western Cape South Africa. Anthony started his own short term rental property management business 7 months ago and has scaled up to 21 cohost properties. Anthony has been doing volunteer work full-time for 10 years. He managed his parents' apartment for about 4 years from a distance to help them with their income. He learned the ropes on that one listing and he maintained a Superhost status for 3 years. Anthony thought that since it worked pretty well, maybe he can manage other owners' properties too and that is when he and his wife started looking for owners. In this episode, Anthony talks about how important it is to take time and be thorough during the listing stage so that you don't work hard and have hassles at the reservation stage.

I had the special honor of speaking with Julie George who we had on episode 30. Julie is the author of the Million Dollar Host and the founder of Host My Home, a short term rental management company that she grew to over 100 properties in 3 years and then sold to Hometime, which is another management company that was looking to expand in the area. In this episode, Julie talks about how other people can build their short term rental business to be able to sell it to the right buyers. We discuss how to value a short term rental business as well. Julie shares what the process of building your business to sell entails and how to achieve what she calls the "ultimate payday".

In this episode, I had the special honor of speaking with Scott Shatford, founder and CEO of AirDNA.co which has over 10,000 active subscribers and analyzes 10+ million properties. With 15 years of experience as a data analyst, Scott realized he wanted to discuss data instead of buying properties. In this episode, Scott talks about what rental arbitrage looked like in 2012, and how AirDNA started. He also talked about how they are pulling information, what kind of information people can be expecting to see on the platform, and how they can utilize those data to successfully run a short term rental business.

In this episode, we have the special honor of speaking with Matt Landau. Matt is the Founder of VRMB, Vacation Rental Marketing Blog, and the Inner Circle which is an online training resource, where he’s been working with hosts and helping them generate more bookings. Matt entered the vacation rental space in the middle of 2006, pre-Airbnb, and owned and operated the only luxury accommodations in Casco Viejo, the historic district of Panama city where he lived. Without any hospitality training, educational resources, and guidance, Matt did everything wrong. Matt shares with us the things that owners and managers should do right now during this crisis and how they can take advantage of this time to be able to sustain their businesses.

I had the honor of speaking with Tim Touchette. Tim is the President and Owner of Stay Attache, a corporate housing company that has over 290 units in the DC area. When Tim and his wife first started in 2011, they placed $200-text only classified ads in the Washington Post. Back then, it was quite challenging to get businesses interested in a small company. Tim had gone through a couple of economic downturns; the 9/11, the 2008 recession, and now, the COVID-19 pandemic. In this episode, Tim talks about what corporate housing is, how they are able to meet the expectations of both the property owners and business clients, and how their business is affected during this time.