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Stacey St. John

Short-Term Rental Investing

JUNE 26, 2025

I used to live the life I thought I was supposed to want—six-figure salary, leadership role, and a calendar packed with back-to-back meetings. But behind the scenes? I was running on empty. The long hours, constant pressure, and lack of control over my time left me burned out.

That journey—from corporate fatigue to building a thriving short-term rental investing portfolio—was recently featured on Entrepreneur.com. And now, I’m sharing how I replaced my full-time income, built a $2M Airbnb portfolio, and created a life of freedom through vacation rental investing.

Overcoming Burnout and Taking Back Your Energy

For over a decade, I climbed the corporate ladder, celebrated performance bonuses, and showed up as the overachiever. But the truth? I was exhausted and craving something more.

My first shift wasn’t financial—it was personal. I started waking up early to reclaim time before the day began. I journaled, reflected, and created space to figure out what I truly wanted.

That morning rhythm became the foundation for my short-term rental business.

Action Step: Start with 30 distraction-free minutes in the morning. Use that time to define your top three priorities. You’ll be amazed at how much energy and clarity it creates.

Getting Started in Short-Term Rental Investing with $50K

Real estate investing seemed overwhelming—until I found the short-term rental model. With $50,000 in savings, I purchased three vacation rental condos (each under $90,000) in a high-demand tourism market.

This was the beginning of my short-term rental investing journey—and I treated it like a business from day one.

Here’s what I did:

  • Bought affordable, cash-flowing properties: I focused on financial returns, not emotional purchases.

  • Held weekly CEO meetings with myself: I reviewed occupancy, revenue, and reviews, using data to make smart decisions.

  • Reinvested all profits: I funded automation, pricing tools, and hired a revenue-share virtual assistant to manage guest communication and dynamic pricing.

Within two years, my short-term rental income surpassed my corporate salary—and I exited the golden handcuffs for good.

The LIVE BIG Framework: Build a Business That Creates Freedom

I developed the LIVE BIG framework to help ambitious women create profitable businesses through short-term rentals—without burnout or confusion. It’s the same roadmap I used to scale my Airbnb business and help other hosts do the same.

Boss² Up: Step Into Your CEO Role

If you want your Airbnb income to replace your W-2, it starts with treating your side hustle like a real business.

  • Set quarterly goals and break them into weekly and daily actions.

  • Track key metrics: booking pace, occupancy, revenue per night.

  • Reflect on what’s working—and what’s not—every single week.

Pro tip: Your short-term rental investing success will mirror the clarity and commitment you bring to the process.

Show Up: Build Confidence Through Consistency

Confidence comes from showing up consistently, not waiting for perfect timing.

  • Start your mornings with focus and action.

  • Connect with mentors and other women succeeding in STR.

  • Make daily learning part of your identity—real estate, mindset, systems, and marketing.

Remember: You don’t need to know everything—you just need to keep moving forward.

Step Up: Scale Through Strategy, Not Hustle

To grow your short-term rental portfolio, you’ll need to stretch into systems and support.

  • Use Dan Sullivan’s “Who Not How” principle: Hire experts who fill your gaps.

  • Reinvest your profits: Automate operations, optimize pricing, and improve guest experience.

  • Build scalable systems: SOPs for messaging, turnover, maintenance, and revenue management.

Bottom line: Short-term rental investing isn’t about doing more—it’s about doing the right things with the right people.

Your Next Steps Toward Short-Term Rental Investing Success

If you’re ready to start or scale your short-term rental business, don’t wait for the perfect plan. Start with action.

  1. Define your “why”: What kind of life do you want to create through real estate investing?

  2. Protect your power hour: Pick one morning this week to work on your STR business before your day begins.

  3. Choose your first “who”: Find one task to delegate or outsource by the end of the month.

  4. Build your runway: Know your monthly expenses and save 3–6 months if you’re planning to exit your job.

  5. Celebrate your first win: Every step counts. Share it and use that momentum to keep going.

Ready to LIVE BIG?

You don’t need to be an expert, have a massive budget, or quit your job tomorrow to succeed in short-term rental investing.

You just need a roadmap, a little courage, and a next step.

That’s exactly what the LIVE BIG framework is designed to give you.

Explore my coaching programs to fast-track your short-term rental investing journey, or grab a copy of LIVE BIG to start building a life of time and financial freedom—one decision at a time.

 

 

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Hey, you!

If you’re a fan of my show, I want to say THANK YOU. Seriously, from the bottom of my heart – I couldn’t do this without you.

There’s one thing that would make me even more thankful – having your support through ratings and reviews on your preferred podcast player. 

This helps me reach more people (just like you) who are eager to achieve their STR goals and dreams.

It’s super easy – just click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved most about the episode!

Also, if you haven’t done so already, please follow the podcast. 

I’ll be adding a bunch of bonus episodes to the feed and, if you’re not following, there’s a good chance you’ll miss out!

Thanks again, sister – and cheers to your STR success!

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