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Drew Pierce

Updated: May 20

The goal of Hardly Hustle is to provide inspiration, drive and motivation in a 10 minute read or less. What you see is what you get. This is hot off the press without an editing team. Drew Pierce is up.

Drew Pierce

Who are you and what do you do?

My name is Drew Pierce. I'm the Co-Founder and CEO of Sage Vacations. Sage Vacations partners with investors to purchase real estate for the purpose of listing on Airbnb and similar websites. Sage Vacations does the market research, purchases, manages the property and guest experience. Creating a passive form of investment for investors.

What did it take to get your first handful of customers?

I started with my close friends and family members, those I knew would trust me with the kind of cash necessary to make such a large investment.

Have you had to pivot the business to get to where you are today?

When it comes to working with investors, that has never changed. However, how I purchase properties and how I market the properties on OTA's have changed several times.

What drives/motivates you on a daily basis?

First, investors have trusted me with a lot of money, I feel a great deal of pressure and responsibility to deliver great returns. Second, family vacations were a very happy part of my childhood and I want to create great guest experiences so that their families can have those same kinds of memories. Third, providing a great life for my kids and lead them by example.

When will you know that you've "made" it as an Entrepreneur?

I think I felt I was a legitimate entrepreneur as soon as my vacation rentals reached $100k in annual revenue in my first full calendar year. For whatever reason, that was the number in my mind that proved to me that this was more than just a side hustle, this was something real. I reached that mark in 2020 and now, in 2023 I'm expecting to reach $500k+ in annual revenue from Airbnb. The longer I'm on this journey, the more I realize how far I have to go still. I'm not sure I will ever feel like I've finally "made" it because there is always more that you can do.

What has been the hardest part of your business journey?

In May of 2022, I had just closed on 2 properties with investors. At this time, Airbnb released their summer update which made mine (along with several other properties on the platform) take a nosedive in bookings. For 10 - 12 days we didn't get a single booking for ANY of our properties. I didn't know what happened or what to do. So I prayed and fasted then went to work. I did a deep dive into what Airbnb's summer release was and how I could navigate that minefield. In this release, Airbnb released categories. Hosts had no way of finding out what categories they were placed in or how to change it. I knew from this that Airbnb had to be scraping data from listings to place inside these categories. So I updated the captions for all of my photos and stuffed them with keywords like, "OMG" and "beautiful", "scenic", etc. to see if I could get placed into as many categories as I could. The second thing Airbnb did is remove titles from listings when guests were searching in an area. The title was what really helped us sell our listings, such as, "Private Fishing Pond | 10 Minutes to Gatlinburg". Now, all they saw was a small cabin that didn't stand out from the rest. So I created an account on Canva and created a 4 photo collage with a big white gap in the middle of it so that I can place the title inside my cover photo. This helped us instantly stand out in search results and has become the new standard. The third and final thing I did was lower my prices. Our listings were so far out of rhythm at this point it needed a quick jolt of bookings in order to have Airbnb push our listings to the top of search results again. Within a few days, we had over 30 new bookings and every property was booked for the next 30 days.

Who or what has helped you the most in your journey so far?

Willingness to adapt/pivot. I modified my pricing model and even fired my cleaning company in one of my markets to offer no cleaning fees several months ago. As the market continues to shift this way, some hosts are finally making the adjustment but most aren't and are choosing to complain instead and will likely soon join the 30% and climbing number of failed Airbnb hosts from this past year alone.

What are a few resources that you'd recommend?

"Get Paid for your Pad" podcast, AirDNA, Wheelhouse, iGMS, TurnoverBnB


List the founders

Drew Pierce, Teresa Wood

How many hours a week do you work on this hustle?


# of Employees?


When did you start?

May 2019

How much did it cost to launch?


What were your funding methods and ballpark amount raised?

I raised money $50k from investors for the down payment and upgrades/furnishings.

Annual revenue?


Projected revenue?


Any call to action?

If you'd like to invest in an Airbnb but don't know how or don't have the time, I'm looking for more investors to join my team.


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