Short-Term Rental Investment Tips & Tricks with Tony J. Robinson


By The Hospitable Team

A six-figure salary and a senior position… or scaling up and being there for every of your kid’s basketball games? Let’s all agree – it is a tough decision to make. Tony J. Robinson decided to take that risk and, as a result, his newly-founded Alpha Geek Capital has managed to build an incredible 10 million dollar short-term rental portfolio in just two years. 

Some of you may already know him from The Real Estate Rookie podcast or The Real Estate Robinsons YouTube channel, where, together with his wife Sara, they reveal all the magic secrets behind vacation real estate with a “heavy dose” of Airbnb focus. provided yet another platform for Tony to share his wisdom. Our VP Customers, Matthew, hosted a Hospitable Masterclass together with Tony, where they talked about getting the most out of the world of short-term rental investments.   

Missed the show live? Jump to the bottom of this post to watch the full recording or buckle up as we bring you the selected inspirational insights in our blog format. 

Popularity and legal considerations – your investment deal-breakers. 

“What are the policies and laws surrounding the market you’re about to invest in?” should be the first consideration of any investment decision. In particular, vacation property investors should be looking into the status of the short-term rental industry in their market: banned, free from regulation, operation under certain strict or maybe relaxed legal terms… What is it?

Tony points out that following the principle of “the less regulations the better” is a common misconception. First, no regulations today mean a higher risk of ever-stricter regulations applied by the local council tomorrow. Second, you actually face greater competition in markets with looser regulations due to lower barriers to entry. 

Got a hold of local laws? Let’s see what is trending then. Popularity is the second most important characteristic for the property investor’s judgment. Why? Because popularity equals the market’s ability to support the profitability of investments. In Tony’s own words:

“If a market has 40 listings, I might not move into that market. Because I don’t know if there’s enough demand for my property to be profitable. Typically, I want to see at least 200 – 300 listings in a market for me to even consider analyzing properties. As much as I think that we’ve got a cool design and we are super creative, if the market can’t support it – the market can’t support it.”

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Long-term partnerships – at the core of your success. 

When talking about partnerships, Tony sums it up in one line.

“The sooner the investors realize that real estate is really about relationships, the sooner they’ll find success.” 

Before purchasing property, investors face private money lenders and capital lenders, who either finance the project directly or enter the game through purchasing together. After the deal is done, cleaners, handymen and local vendors step in.

Obviously, the capital front-end is of the most interest here. While there are people ready to invest in short-term rental projects, they do not have the necessary skills, time, or desire to dig into such a business themselves. For those people, your role is a “problem solver.” 

  • Take over the deal
  • Manage the property rehabilitation
  • Fully set up and furnish
  • Take care of the listings long-term 
  • Collect checks from your partners

Great return for your clients and a great business model for you, but how to find those partnerships? It’s 2022 – be vocal about what you do in your own media.

Tony says, “You don’t need a massive following. What you need is consistency. What you need is to provide value to people and, eventually, they’ll raise their heads and say ‘Hey, we would love to work together!’ And that’s incredible.” 

Curious to watch the full masterclass, as Tony provides more insights on driving your investments and analyzing heavy-tourism, local and out-of-state properties?

Get the best pro tips from renowned industry experts in our Hospitable Masterclasses!

Already established a property portfolio and want to earn reservations and generate additional income without sacrificing your free time and energy? 

Hospitable is here to support a world where short-term hosting is just as carefree as simple property investment. Get your 14-day free trial now!

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