My first Airbnb Investment: From its Start to a (Happy?) End.

Don't we all want to be able to share our most valuable assets with the people we love most? If you are human, you most probably like to be on the giving end. Probably at times, you must have wished you had a larger home to host your siblings, parents, and friends for a weekend.

The average investor tends to live below their means. This translates to living in a regular-sized home and finding space for your loved ones can be difficult.
This was an issue that I was facing in 2019. Trading up to a larger home was not in my budget at that time, but I did want to create a business where I would find some jot.
Coming from the world of commerce, I was getting turned off by the constant need to take out loans just to turn inventory, the constant managing of customer returns which has a great impact on profits as well as the need to constantly push products into consumers hands. Most of the items I was selling were easily available by the competition. Frankly, I wanted something that would create memories and leave people with a good feeling.
After thinking about this for a while, I had an epiphany. What if I can purchase a home and rent it out on Airbnb. Better yet, being the frugal person that I am, I would be able to visit my Airbnbs with my family and not worry about the cost. More than that, I would be able to have family that never thought of vacationing or just going away for a night to finally be able to afford a much-needed break.


After deliberating about the pros and cons, I closed on my first real estate investment in Harriman NY. The condo was 25 minutes away from my home with a very popular outdoor shopping mall nearby. I reached out to the HOA and got their permission to proceed. Right away, booking started to roll in. I remember that my first guest showed up at 2 AM. I nervously reached out to my next-door neighbor to make sure she wasn't disturbed during the night. A bit annoyed she replied, "Jacob, I mind my business and you should mind yours".


Below, is how my Airbnb page looked at the time. My wife, Rivkah, is the profiled host.

I was ecstatic! This was going to be huge. In early June, I started to get bookings through September. After weeks into business, the hammer dropped. Yes, the HOA received a complaint from an old gentleman who lived on the other side of the community. He was unhappy with the flow of guests and triumphantly showed up at the HOA headquarters with a printout of my Airbnb listing. To make a long story short, I was ordered to cease operations come September. I didn't even want to consider finding a long-term tenant. Besides that I would negatively cash flow, it did not interest me in the least.
As soon as the first complaint came in from the neighbor, I immediately went and posted my condo for sale on Zillow. I was hoping to have this turn out in my favor, but just in case it didn't I wanted this off my hands asap.


I got some calls. A few inquiries in, a gentleman who lived in the community reached out. He was looking to scale up from a 1 bedroom to my 2 bedroom condo. I asked him to email me a picture of his ID and remotely buzzed him in. He had a look at the place, we agreed on a price and got the ball rolling. A day before closing in September, I met him there for a walkthrough. This was a few days after I moved out the furniture and decor. Guess what his first comment was?


Guess again!


This looked nicer than it did last time. HAHA! I kinda felt bad but at the same time felt good about how I took a simple apartment and made it look special.

We closed for $190K My purchase price was $170K. I just about broke even after all the closing costs so I wasn't one to complain. 

https://www.zillow.com/homedet...


Key Takeaways.


1. Don't rely on a simple reply from the HOA office that yes, you can run an Airbnb. Get it in writing and make sure there is a precedent for STRs in your community.


2. GOD decides just how much pain you should go through. I was destined to go thru the pain of closing down my first Airbnb. When it came to selling it, it couldn't have been easier.


We did manage to have fun though in the short time we had it. The day before moving everything into storage, I had my wife and kids join me for a sleepover. It was their first and last time staying there. It was an experience we would never forget!


Thank you for reading till here. I hope you enjoyed my first blog post and will continue to post updates and takeaways from my Airbnb journey.