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29. From Accidental Host to Real Estate Powerhouse with Ashley Lang
Airbnb Roadmap Accelerator Course
Hey, it’s Brittany! In this episode of The Airbnb Roadmap, I sit down with Ashley Lang—a powerhouse real estate investor with a diverse and thriving portfolio. Ashley shares how she stumbled into short-term rentals by accident and ended up scaling to over 30 furnished rentals, most of which are now midterm stays. We talk about the transition from vacation to midterm rentals, how she built a full team to support her, and the mindset shifts that helped her (and her husband) take the leap into real estate full time.
Whether you’re a first-time investor or dreaming of scaling your portfolio while working less, this episode is packed with lessons from someone who’s built it step-by-step—and done it with intention.
Key Takeaways from My Conversation with Ashley Lang
Ashley’s first Airbnb was meant to be a weekend getaway—but high demand flipped the script.
Even back in 2018, Ashley’s thoughtfully designed space stood out and stayed booked. Her advice? Don’t underestimate the value of great aesthetics and guest-ready amenities.
After starting with short-term rentals, Ashley found her groove in midterm stays—less wear and tear, lower management needs, and consistent income.
Ashley shares how she gradually built a “mini army” of VAs, assistants, revenue managers, and marketers to take tasks off her plate so she could grow the business.
Ashley’s mix of long-term, midterm, short-term rentals—and flips—gave her stability and options during market shifts.
One of Ashley’s top tips? Surround yourself with people doing what you want to do—and work on your mindset like it’s your job.
We talk about the power of believing in your goals, visualizing success, and stepping into the version of yourself who already has what you want.
Why Listen to This Episode?
If you’ve ever wondered:
Then this is your episode.
Ashley shares a behind-the-scenes look at how she grew her portfolio and team while staying aligned with her goals—and how you can too.
Mentioned in the Episode
Let’s Connect
Thinking about building a midterm or short-term rental portfolio? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.
Work With Me
Want help buying, analyzing, and launching your first (or next) short-term rental? Visit frontporchrealtyco.com or check out my course at airbnbroadmap.com.
Chapters
00:00 – Intro & Ashley’s accidental start
02:30 – From one rental to two (and then thirty!)
05:00 – Design, demand, and why midterms won
11:00 – Building her dream team
14:00 – Scaling with intention
18:00 – Why they diversified the portfolio
23:00 – Buck’s journey from W2 to full-time investor
25:00 – Top advice for first-time STR investors
28:00 – Manifestation and mindset shifts
30:00 – Where to find Ashley
Subscribe and Share
If you found this episode helpful, hit that subscribe button and share it with a friend who’s thinking about diving into real estate investing. You never know who needs to hear it today!
View all episodes
By Brittany Wenninger
Airbnb Roadmap Accelerator Course
Hey, it’s Brittany! In this episode of The Airbnb Roadmap, I sit down with Ashley Lang—a powerhouse real estate investor with a diverse and thriving portfolio. Ashley shares how she stumbled into short-term rentals by accident and ended up scaling to over 30 furnished rentals, most of which are now midterm stays. We talk about the transition from vacation to midterm rentals, how she built a full team to support her, and the mindset shifts that helped her (and her husband) take the leap into real estate full time.
Whether you’re a first-time investor or dreaming of scaling your portfolio while working less, this episode is packed with lessons from someone who’s built it step-by-step—and done it with intention.
Key Takeaways from My Conversation with Ashley Lang
Ashley’s first Airbnb was meant to be a weekend getaway—but high demand flipped the script.
Even back in 2018, Ashley’s thoughtfully designed space stood out and stayed booked. Her advice? Don’t underestimate the value of great aesthetics and guest-ready amenities.
After starting with short-term rentals, Ashley found her groove in midterm stays—less wear and tear, lower management needs, and consistent income.
Ashley shares how she gradually built a “mini army” of VAs, assistants, revenue managers, and marketers to take tasks off her plate so she could grow the business.
Ashley’s mix of long-term, midterm, short-term rentals—and flips—gave her stability and options during market shifts.
One of Ashley’s top tips? Surround yourself with people doing what you want to do—and work on your mindset like it’s your job.
We talk about the power of believing in your goals, visualizing success, and stepping into the version of yourself who already has what you want.
Why Listen to This Episode?
If you’ve ever wondered:
Then this is your episode.
Ashley shares a behind-the-scenes look at how she grew her portfolio and team while staying aligned with her goals—and how you can too.
Mentioned in the Episode
Let’s Connect
Thinking about building a midterm or short-term rental portfolio? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.
Work With Me
Want help buying, analyzing, and launching your first (or next) short-term rental? Visit frontporchrealtyco.com or check out my course at airbnbroadmap.com.
Chapters
00:00 – Intro & Ashley’s accidental start
02:30 – From one rental to two (and then thirty!)
05:00 – Design, demand, and why midterms won
11:00 – Building her dream team
14:00 – Scaling with intention
18:00 – Why they diversified the portfolio
23:00 – Buck’s journey from W2 to full-time investor
25:00 – Top advice for first-time STR investors
28:00 – Manifestation and mindset shifts
30:00 – Where to find Ashley
Subscribe and Share
If you found this episode helpful, hit that subscribe button and share it with a friend who’s thinking about diving into real estate investing. You never know who needs to hear it today!