If you’ve never thought about investing in real estate, this power couple might just change your mind. Meet the Kutchers. Jenna and Drew Kutcher run a successful business in Hawaii from their home in Minnesota. They own 2 rental properties on the island of Kihei that they rent out to vacationers through Airbnb.

The couple decided to embark on this journey when they decided they loved Hawaii too much not to own a place there. They loved it so much that they wanted to live there for 1 month out of the year to relax, disconnect, and spend time with family.

Once they had this idea to relocate for 1 month, they started crunching the numbers. If one month at a resort in Hawaii would cost not much less than what a down payment would be on a condo, why not go for it?

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It wasn’t long after this realization that they decided to buy a property in Hawaii. “We visited the island, fell in love, and knew we wanted to have a place we could escape to annually but more importantly, a place where we could give YOU, our friends, the full Maui experience,” the Kutchers explain on their Airbnb website.


How They Started:

Like any major financial decision, they sat down and had a proper conversation about it. If they were going to do this, they were going to do it right.

They ran the numbers, calculated the expenses, reviewed taxes, and looked at property rates. The next few weeks of their lives consisted of mass amounts of research. This research process is extraneous, but 100% necessary if you want to make profits from the real estate and run a successful rental property.

Some of the KEY things to consider before buying:

LOCATION: is this a popular place to visit?

PROPERTY TYPE: do you want an apartment, condo, townhome, etc.? Which is most financially efficient in the area you’re in?

BUDGET: what are you willing to spend? How long will it take to start earning back money?

RENOVATIONS: do you need to update the property?

FURNISHING: how much new furniture, decor, paint, etc. will you have to invest in?

MAINTENANCE: who is going to maintain the property overtime and in between visits? Do you need to hire outside help?

RATES: what are you going to charge for your property?

MARKETING: how are you going to market your property and get people to stay there?

LEGAL: each state has different property laws that are important to know before purchasing real estate.


They bought a property. Now what?

Once they bought the property, it was go time. They had to start renting this property out ASAP if they wanted to start earning money back on their investment. Without renters, you are only losing money, which is a risk Jenna and Drew were willing to take.

But being successful business owners, they had a plan to ensure they were booked for months at a time.

Jenna has a successful photography business, blog, and podcast that she was able to use to her advantage when promoting their Airbnb. Being and avid brander, Jenna decided to create a website and instagram for what they call, “The Kutcher Condo.” These platforms are filled with information, resources, and recommendations while you’re on the island.

Just visiting these sites gives you a peak into what staying at their condo might be like. It allows guests easily find their condo and access all the information they could need about a potential vacation.

“The website serves not only as a place for people to check out our space but also shares our favorite things about Maui — adventures, restaurants, beaches, and activities. We wanted to have one landing page for when people ask us for our recommendations and it was fun to put it all in one spot with a beautiful branded website. Because duh, it’s me,” Jenna writes on her blog.

This is a huge attraction for people looking for somewhere to stay on the island. How many Airbnb hosts do you know who create a separate brand for their home? This creative edge is what really makes their condo stand out from the rest. Jenna and Drew have been profitable every single month of owning. They are on pace to start earning all profits off of the property within 8 years.

“Knowing that we could be under 40 and be making an income from this property was a huge incentive for us,” explained Jenna.

So what’s the secret sauce to running a successful Airbnb?

The answer is to always go above and beyond what your guests expect of your Airbnb. Underpromise and overdeliver is the philosophy behind both of Jenna and Drew’s Hawaiian properties. Not only do they have an abundance of information on their personalized website for their properties, but they also ensure that the condo itself is filled with the necessities. They keep beach chairs, towels, sunscreen, aloe, coolers, and more on the property at all times for vacationers to use as they wish.

When you see the time and effort they put into their condo, it shows how much they care about their guests. The little touches here and there set them apart and make people want to book a stay, come back, and recommend to their friends. 

Create a space that you would be proud to call home, and open it up to travelers to enjoy. Airbnb can be a fun and rewarding investment that may just start you on the path to financial freedom.

Looking to start your own Airbnb business? Here’s a guide for how to save for your first home!