In Hospitable Hosts, a collection of inspiring stories from successful short-term rental entrepreneurs, HostGPO CEO Jeff Iloulian shares his journey from attorney to industry leader. 

His chapter dives into the challenges, lessons, and pivotal moments that shaped his path; from assembling furniture late into the night to eventually founding HostGPO, a buying group for vacation rental hosts. His story is one that many in the space can relate to and hopefully be inspired by. Read how he made the leap and what he learned along the way.

Jeff’s Chapter from Hospitable Hosts

They say that the key to success is often found outside of one's comfort zone. For me, an attorney turned vacation rental entrepreneur, this certainly rings true. 

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When I first heard about lease arbitrage in the short-term rental (STR) industry, I was immediately intrigued. I had been practicing law for several years, but I had always been fascinated by the hospitality industry and loved to travel. In fact, I had just come back from a trip to Copenhagen where I stayed in a stunning vacation rental in the middle of Nørrebro - a hip part of town that has no hotels in it. So, in 2014, when I learned you could make money by renting a house, furnishing it, and creating a vacation rental experience for others to enjoy I decided to get uncomfortable and give it a shot and leased the home directly across the street from where I lived.

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As an attorney, I was used to (1) tracking every minute of my day (billing by the minute) and (2) being an egomaniacal overachiever. I was hyper-aware of how I spent my time. I would wake up early, work a full day as a lawyer, and then do the heavy vacation rental work at night - with some sporadic guest messaging from my phone during coffee breaks and from the watercooler. It was a lot of work, often 14 hour days between the two, but I enjoyed it, and it gave me a taste of being my own boss - where “the sky was the limit.”

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Those grueling months, full of long days, started to take their toll. I was used to valuing my opinion and trusting my gut, but in the vacation rental industry, I had to learn to be humble and learn from my (many) mistakes. I can recall a specific "red pill" moment for me, when I accidentally ripped my suit pants while trying to assemble a coffee table late at night - I was out of my comfort zone and clearly doing things wrong. I had lost track of valuing my time, was stretching myself too thin, and was trying to solve problems with brute force rather than intellect. 

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Back then, there was no vacation rental community and very little industry education material. Fortunately, I had stumbled upon a great business partner who coached me through those months of my STR journey…and helped me buy a new pair of slacks.

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I took a step back to reflect, and then took a leap of faith to hang up the suit altogether  and I am glad I did. I have since managed over 250 vacation rental units, from super-luxury mansions in Malibu to cabins in the woods, and have had tens of thousands, if not hundreds of thousands, of guests with plenty of crazy vacation rental stories (from drug busts to corrupt cops, from checking in A-list celebrities to cooking dinner with a family of 9 from Laos). Even though I started in 2014, which was already 3.0 or even 4.0 in the evolution of the modern vacation rental industry, it still feels like it was the Wild West today.

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As the vacation rental community continues to grow, I have tried to pass on lessons I had learned and to lift others up on their own paths. One of my biggest lessons, which has become the focus of my career now, is educating folks on how to furnish a vacation rental home. In the beginning, I would often pick up items off the street or buy things from big box stores like Ikea. I quickly realized that this approach was not sustainable. Low quality sheets and pillows got guest complaints, and buying cheap furniture from big box stores ended up costing me more time and money in the long run because I had to replace them frequently. 

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While online shopping can be a good alternative, it also has its challenges. There are so many options that it can be overwhelming, and many people end up buying off-brand items that they don't know anything about. I also went through a phase of buying from unknown online brands, but it often felt like playing roulette, with no guarantee of the quality of the items I was purchasing.

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There was one day in particular that changed it all. I was at an Ikea with my team of 16 people, and we ended up with 48 shopping carts full of items to check out. Uncomfortable. The checkout alone took three hours, and when I asked for a discount, the woman just laughed and said it wasn't even close to enough for a “volume” discount. The whole experience was a nightmare, and didn’t end there; we still had to build the furniture. When one of our many U-hauls got into a fender bender, it was the final straw. I swore to myself that I would never do it again.

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After one of the craziest 48 hours of my life, I knew there had to be a better solution. I co-founded HostGPO to provide a curated selection of high-quality, durable furnishings and supplies for vacation rental owners. By leveraging the buying power of a group, we are able to offer better prices and take the hassle out of sourcing and setting up vacation rental units. Our 50+ vendor partnerships were made so HostGPO members always get better rates than the standard trade discount or through other wholesale clubs.

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As a host myself, I understand that there's more to running a vacation rental business than just buying furniture, linens, and supplies. That's why HostGPO has also partnered with service-based companies in areas such as insurance, dynamic pricing software, welcome guides, and more to provide our members with a complete package of support.

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Looking back at my journey, I can confidently say that stepping out of my comfort zone has made that zone bigger. By stepping out of my comfort zone,I have built a successful business managing hundreds of vacation rental units, and I have founded a company that represents hundreds of thousands of units, and am able to help other hosts grow and succeed. I keep pushing myself every day to get even further outside. It has been a wild ride, but I am grateful for every experience and every lesson learned along the way. For anyone thinking about taking a leap of faith - relish the discomfort! You never know where it might lead you.

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