full-time airbnb investing Turning your part-time portfolio into your full-time gig

When to flip the switch to full-time Airbnb investing?

Real estate investing is often thought of as one of the most common side-gigs — the landlord who owns a rental unit, the young couple who operate an Airbnb. It’s infrequent that you come across a real estate investor who skipped the side-gig part and went straight to full-time Airbnb investing. Why’s that?

When you think of real estate investing more generally as a form of entrepreneurship, you’ll realize that entrepreneurs with a side business have long nurtured a side-gig until it’s viability as a main-gig. Side-gigs and passion projects are an affirmation that financial success doesn’t have to come at the cost of personal fulfillment, and that there are other ways to fulfill financial goals, whether that’s a comfortable retirement or a seven-figure enterprise. And it’s that aim, always present from the start, that leads to a startup’s eventual success; Steve Jobs isn’t the only founder to change an industry from inside a garage.

In fact, real estate has been one of the best on-the-side investment strategies for decades. A lot of working entrepreneurs understand the value and opportunity in real estate investing, but feel a barrier to entry that prevents them from exploring it as a true full-time strategy. In the post-COVID landscape, though, the barrier to entry has never been lower.

The magic of short-term rentals

There’s been an overwhelming shift among renters to prefer shorter-term accommodations. The work-from-anywhere adoption, month-to-month leases, and Airbnb-style stays are becoming more and more popular, as professionals opt for a change of scenery and families explore new locales with more favorable living conditions. In this market, anyone with an address has an asset, whether it’s a spare bedroom, a basement apartment, or a full-fledge vacation rental.

full-time airbnb investing work-from-home

Short-term rental management lends itself to the same kind of quantitative analysis as other startups. Owners can invest in an automated owner’s portal that tracks their monthly occupancy, revenue, and expenses. They can outsource the tenant turnover process and automate payments to housekeeping and maintenance professionals. With virtual check-ins and hands-free access keys, owners can manage their property from anywhere in the world. Or, for investors who want to experience the benefits of truly passive income, there are full-service property management partners that will streamline and handle all operations while maximizing your profits, leaving you with more time in your life and money in your pocket.

The short-term rental strategy is scalable, and it allows owners to generate high yields at low levels of risk. Owners can master the art of concurrent listings and track the performance of their property at different price points and stay lengths. The value is twofold—the short-term rental generates immediate revenue, while the value of the property as an asset continues to increase. And with a shortage of supply on the market, short-term rentals are a great way for self-starters to participate in an independent endeavor that has every potential to lead to financial freedom and total lifestyle flexibility. 

Turning your side-gig into your main-gig

Timing is everything

When it comes to translating a side-endeavor into a full-time focus, timing is almost everything. Popular culture glamorizes the grind-until-it-works modality, but so many investment and startup endeavors are better nurtured if the owner is able to keep his or her day job until the fledgling company is fully ready. The Academy of Management published a study that found a 30% greater success rate with startups that are built while the owner is still working full time; real estate investing and property management is no different.

Letting the numbers lead the way

Still, there comes a moment when the time is right to bring a side-focus into the spotlight. This is a decision best supported by numbers, consultations, and business plans; it’s best if an owner is prepared with monetary goals and KPIs before they consider moving into the full-time fast lane. Investors and owners don’t have to re-invent the wheel; this is an important place for founders to reach out to their mentorship networks or to consult with other investors in their local market to learn more about what they need to build a strong portfolio and keep it on its feet.

Another sign that an owner is ready to focus on their real estate strategy full time is the revenue potential of their property. This depends on the market, the owner’s advertising choices, and how much sustained demand the property has seen. With an analytical approach to rental data, the owner can make more informed decisions as they continue to grow their rental business.

full-time airbnb investing data

Setting and checking on your goals

Finally, it’s important that owners understand their goals as it relates to portfolio growth. Not every business is meant to scale quickly. In fact, pre-mature acquisitions can be a major flaw in an early investor’s strategy. Owners should understand their personal goals and have a clear strategy before they go full-time, regardless of the revenue targets for which they aim. 

The impulse toward entrepreneurship has been one of the best drivers of innovation across multiple sectors. One of the best things an early-stage investor can do is keep their rental business on the side. Then, with proper revenue projections, growth plans, and marketing strategy, there could come a time in the investment journey when it’s possible to commit to portfolio management with more focus. At that point—and only then—let the full-time launch begin. 

Looking for help scaling your portfolio? Our proprietary data, sourcing methods, and full-service property management technologies can help. Drop your details below.


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  • Rely on trusted partners (us!) to manage your property for you, giving you time back in your busy day.
  • Enjoy higher yields, powered by our innovative dynamic nightly pricing and flexible lengths-of-stay strategies.
  • Get ahead of an already booming industry, effortlessly.