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The Resilient Journey of Matt Hays in Real Estate
In today’s shifting real estate landscape, adapting quickly can mean the difference between growth and failure. Matt Hays’s story is a masterclass in pivoting with purpose. From flipping to long-term rentals to mastering Airbnb strategies, Matt Hays turned setbacks into a resilient business model that generates consistent motivated seller leads and long-term cash flow.
From Flipping to Falling: A Brutal Wake-Up Call
Matt Hays and his wife have been in the real estate game for nearly two decades. They started with land deals, progressed through wholesales, rentals, and flips. For years, everything was going smoothly—until it wasn’t.
Their flipping business, once thriving with over 42 deals under contract, took a massive hit when a hedge fund backed out of buying their renovated homes. The fallout left Matt owning properties mid-renovation, tied up with millions in cash and financing, and no clear exit. It was a financial and emotional blow, one that could have ended it all.
But instead of folding, Matt pivoted. He fire-sold half the properties, fully renovated and sold a portion for retail, and transitioned the remaining into long-term and short-term rentals. It wasn’t easy, but it worked—and Airbnb became the unexpected hero of his portfolio.
The Airbnb Pivot: From Risk to Reward
Airbnb wasn’t Matt’s original strategy. He saw it as a temporary option for properties that couldn’t sell. But as the cash flow began rolling in, the potential was undeniable.
With properties in St. Louis, Kansas City, and Florida, Matt quickly realized that Airbnb wasn't just a short-term fix—it was a powerful wealth-building tool. He developed a simple yet effective rule: properties valued around $300,000 should aim to bring in at least $60,000 in annual gross revenue. With thoughtful design, themed spaces, and amenities that cater to families, many of Matt’s listings outperformed expectations.
How to Choose a Profitable Airbnb Market
Matt's success wasn’t just luck. He strategically avoided oversaturated urban areas with heavy regulations and focused on suburban pockets with high demand and minimal restrictions.
He shares an example of two properties in a town with no Airbnbs but also no restrictions. Despite data sources showing poor forecasts (due to lack of existing listings), he trusted his instincts. The results? Those properties exceeded expectations and became top performers.
Matt emphasizes looking for:
- Suburbs outside major cities
- Unincorporated or regulation-light zones
- Areas with demand from family visits, local events, or conventions
The secret is understanding why people travel to a location. Hotels exist for a reason. If there's a Holiday Inn nearby, chances are there's demand for overnight stays. Airbnb just meets that demand differently.
Avoiding Common Flipping Mistakes
Matt is brutally honest about the mistakes that nearly cost him everything:
- Hiring the Wrong Contractors: Always ask for five referrals and verify W-9s and insurance. Cheap bids often result in expensive rework.
- Overestimating Profit Margins: Inflation and poor workmanship turned $50,000 budgets into $75,000 disasters.
- Underestimating Market Risk: A 10% drop in the market wiped out nearly a million dollars in equity.
- Lack of Daily Oversight: Without a strong management structure, quality control became a nightmare.
He urges investors to run numbers based on worst-case scenarios and only move forward if the deal still makes sense.
Building a Family-Focused Airbnb Brand
Operating under the name Blair’s House, Matt and his wife have created a brand around quality and comfort. Their properties are:
- Designed with families in mind
- Equipped with game rooms, themed bedrooms, and fully stocked kitchens
- Maintained with rigorous post-cleaning inspections by Matt’s wife
They avoid party bookings and focus on guests traveling for family events, conventions, or extended stays. Their commitment to cleanliness and hospitality gives them a competitive edge—and it’s what turns guests into repeat visitors.
Leveraging Technology for Seamless Management
Matt uses Guesty for Pros to sync listings across Airbnb, VRBO, Booking.com, and a direct booking website. This prevents double bookings and simplifies operations.
His process:
- Upload photos and listings via Airbnb’s mobile app (he prefers the mobile interface to streamline setup)
- Perfect the listing details manually
- Import data into Guesty
- Push to all platforms automatically
Automation extends to guest communication too. From check-in codes to checkout reminders, everything is streamlined to reduce workload and ensure consistency.
Superhost Status: Why It Matters
Only 17% of Airbnb hosts are Superhosts. That distinction brings a 24% visibility advantage.
Matt ensures Superhost status by:
- Keeping a 5-star rating
- Responding quickly to guests
- Avoiding cancellations
The result? Higher bookings, better guests, and increased revenue.
What Sets Blair’s House Apart
Blair’s House isn't just another Airbnb host. It’s a curated hospitality experience. From pillows placed perfectly to stocked pantries and toiletries, nothing is left to chance.
Their philosophy: guests form their opinion in the first 30 seconds based on what they see and smell. One bad impression triggers a cascade of complaints. Their solution? Perfection.
They listen to guests, adapt, and maintain an ongoing relationship with every visitor. And most importantly, they never assign guests chores like laundry or excessive cleanup. Hospitality means making the experience frictionless.
Using Airbnb’s AirCover to Protect Your Property
One of Matt’s most practical tools is Airbnb’s AirCover, a built-in protection plan that covers up to $1 million in property damage. He’s successfully submitted claims for cleaning and damage issues, often receiving reimbursement within hours. For investors hesitant about guest damage, AirCover offers serious peace of mind.
Avoiding Oversaturation and Regulation Pitfalls
Matt shared how Kansas City became a cautionary tale: over 10,000 short-term rentals and a crackdown on regulations now mean hosts must get approval from 66% of their neighbors and face $300/day fines if unpermitted. By focusing on suburban areas and understanding local laws, Matt avoids these traps—and helps others do the same.
Designing Airbnb Listings That Deter Problem Guests
Matt and his wife intentionally design their listings to attract families, not party-goers. From bunk beds in themed rooms to Star Wars decor and game rooms, their properties visually signal who they’re for. This strategy helps reduce risk and maintains the quality of their Airbnb brand.
The Power of Guest Feedback Loops
Matt uses automated messaging to check in with guests on the night of arrival, asking if anything is needed. This feedback loop improves guest satisfaction, builds trust, and often surfaces minor issues before they become complaints.
From Ramen to Real Estate: Matt’s Work Ethic
Matt credits his success to unrelenting work ethic. Inspired by Dana White, he emphasizes that today’s generation has every resource at their fingertips. In his words, if you're willing to work hard, outwork the competition, and stay focused, success is "easier than ever"—but only if you show up and grind.
From Property Owner to Coach
Seeing how many others were struggling with Airbnb, Matt launched a coaching program. He offers group sessions, in-person classes, and private mentorship.
His goal? Help others escape the rat race. From working multiple jobs and living on ramen to managing a thriving portfolio, Matt has been there. Now, he wants to help others get there too.
Key Takeaways from the Blog
- Adaptability Is Key: Matt Hays turned a devastating business setback—when a hedge fund pulled out of 42 contracts—into a new opportunity by transitioning to Airbnb and long-term rentals.
- Airbnb as a Long-Term Wealth Strategy: Originally seen as a stopgap, Airbnb became Matt’s most valuable asset class, generating consistent cash flow and preserving his business.
- Profit Rule of Thumb: Properties valued at ~$300K should ideally produce ~$60K in gross annual Airbnb revenue.
- Market Selection Matters: Matt emphasizes avoiding oversaturated and highly regulated urban markets, favoring suburban pockets with demand and fewer restrictions.
- Lessons from Flipping Mistakes:
- Hire qualified, vetted contractors.
- Don’t rely on best-case numbers.
- Budget for inflation and delays.
- Monitor rehabs closely—daily if possible.
- Hire qualified, vetted contractors.
- Blair’s House Brand Philosophy:
- Target family travelers with themed rooms and game spaces.
- Maintain impeccable standards (cleanliness, functionality, ambiance).
- No guest chores—just hospitality.
- Target family travelers with themed rooms and game spaces.
- Technology and Automation:
- Uses Guesty for syncing listings across Airbnb, VRBO, Booking.com.
- Prefers starting listings on Airbnb mobile for ease and speed.
- Automates guest messaging from check-in to check-out.
- Uses Guesty for syncing listings across Airbnb, VRBO, Booking.com.
- Superhost Advantage: Only 17% of hosts are Superhosts. Achieving and maintaining that status results in a 24% visibility edge.
- Airbnb’s AirCover Protection: Matt successfully used Airbnb’s built-in damage protection (AirCover) to file and quickly resolve claims, offering peace of mind for property owners.
- Avoiding Regulatory Pitfalls: Kansas City serves as a cautionary tale, with 10K+ STRs now facing fines and steep neighbor approval processes. Matt navigates around these issues by targeting permissive zones.
- Design to Pre-Screen Guests: Listings are designed to naturally filter for families and deter problematic guests (e.g., bachelor parties) through visuals and amenities.
- The Feedback Loop: Automated mid-stay check-ins help identify and fix issues proactively, creating better experiences and boosting reviews.
- Work Ethic Over Excuses: Matt stresses hustle and resilience. His journey from ramen noodles to real estate success underscores the value of relentless work and focus.
- Coaching and Mentorship: Matt now offers group coaching, in-person classes, and private mentorship to help others replicate his success in the Airbnb space.
- Motivated Seller Leads: By building a strong rental portfolio, Matt not only created steady income but also generated ongoing motivated seller leads—fueling long-term growth.
Final Thoughts: The New Real Estate Blueprint
Matt Hays’s journey is a testament to resilience and reinvention. Flipping may have provided fast wins, but it was Airbnb that built sustainable, long-term wealth. With the right strategy, technology, and guest experience, short-term rentals can generate consistent cash flow and secure high-quality motivated seller leads.
For real estate investors looking to pivot, Airbnb isn’t just a backup plan—it’s a growth strategy.
Ready to Build a Profitable Airbnb Business?
Whether you're new to real estate or looking to scale your portfolio, now's the time to take action. Embrace the systems, avoid costly mistakes, and learn from industry pros like Matt Hays.
Start your journey today. Build your real estate business. Create consistent cash flow. And most importantly, generate motivated seller leads that fuel your long-term success.
