Reverse-Engineer Demand and Win Contracts

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/