220. The Tricks and Tips to a $170,000/month Mid-Term Rental Company

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Jan 5, 2026

Jesse Vasquez, an entrepreneur who pivoted from a $200k salary to become a mid-term rental expert, discusses the lucrative world of 30-day stays. He reveals how his portfolio earns over $170,000 monthly by working with hospitals and corporate clients. Jesse shares tips on securing profitable contracts, including leveraging rental arbitrage and strategic outreach to recruiters. Discover practical steps for launching your own mid-term rental business and learn why understanding guest needs is crucial for success.

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ANECDOTE

Travel Nurse Moment Sparked The Business

Jesse first noticed midterm demand when a travel nurse told him she stayed 90 days in a Motel 6.
That conversation revealed companies pay 2–5x long-term rents and launched his strategy.

ANECDOTE

Putting Your Foot In The Door Worked

Jesse literally stuck his foot in a hospital HR door to meet a recruiter and start a relationship.
That awkward action led Misty to say, "we'll work with you," and jumpstarted his bookings.

ADVICE

Reverse-Engineer Demand With Listings

Use Airbnb and Furnished Finder to reverse-engineer which companies and roles come to your market.
Ask guests which company they work for and size your property mix to that demand.

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Imagine walking away from a $200k salary to bet on a gap in the real estate market. That’s exactly what Jesse Vasquez did. Today, his portfolio generates over $2.1 million annually by focusing on the "Mid-Term Rental" (MTR) strategy—a sweet spot between long-term leasing and high-turnover Airbnbs.

In this episode of UpFlip, Jesse reveals how MTRs generate 3-5x the cash flow of traditional rentals. Whether you have zero properties or a full portfolio, Jesse breaks down how to secure contracts with hospitals, insurance companies, and construction firms to keep your units booked for months at a time.

In this episode, you’ll learn:

The MTR Goldmine: Why 30-day stays (mid-term rentals) are the most stable and profitable niche in real estate today.
The "Lead Connector" Model: How to earn 10% referral fees by simply connecting companies to landlords—without owning or renting anything yourself.
Rental Arbitrage 101: How Jesse rents homes for $3,000 and legally subleases them to corporations for $10,000.
The "Extended Stay" Hack: A guerrilla marketing tactic where you drive by hotels to spot out-of-state work trucks and steal their corporate contracts.
The Indeed & LinkedIn Strategy: A step-by-step workflow to find travel nurse recruiters on job boards and DM them to secure direct bookings.
Insurance Housing Secrets: Why insurance companies pay 3-5x market rates to house displaced families and how to get on their radar.
Reverse Engineering Demand: How to use Furnished Finder and Airbnb not to list, but to research exactly which companies are sending employees to your city.
The Perfect Pitch: The exact "money-saving" script Jesse uses when cold-calling HR departments.
Essential Amenities: The under-$100 upgrades (like blackout curtains and noise machines) that are non-negotiable for night-shift nurses.
The Empathy Edge: Why focusing on the human element—like a family needing a dinner table after a fire—will skyrocket your business faster than focusing on ROI.
Timestamps
(00:00) Intro: From "Golden Handcuffs" to $170k/Month
(04:30) The "Foot in the Door" Moment: Landing the First Contract
(08:45) How to Identify the Best Properties for MTR
(16:20) Rental Arbitrage: Making Money Without Owning Homes
(21:00) How to Find Leads (The "Extended Stay" & Indeed Method)
(27:15) The Fan Blitz: Best Upgrades & Mistakes to Avoid

Tags: Property Management, Entrepreneurship, Passive Income, Real Estate, Mid Term Rental, Rental Arbitrage, Insurance Housing, Jesse Vasquez

Resources:Grow your mid-term rental business today: https://www.upflip.com/course/the-mid-term-rental-blueprint

Connect with Jesse: https://www.instagram.com/therealjessevasquez/