Ep - 281 Why Midterm Rentals Are the Smarter STR Strategy with Vivian Yip

Vivian Yip went from corporate burnout at Apple to building a thriving midterm rental portfolio and property management company.

In this episode, she breaks down how she pivoted during the pandemic, why most investors don’t have enough grit, and how mastering calendar discipline can completely transform your rental income.

We dive into:

• Why community changes everything in real estate

• The biggest mistake STR hosts make when pivoting to midterm rentals

• Calendar discipline and how to control guest behavior

• How to use data tools like PriceLabs the right way

• Building multiple income streams without burning out

• Protecting your time while scaling a real estate business

If you’ve been feeling stuck, burned out, or uncertain about the next step in your rental business — this episode will challenge you to think differently.

Timecodes:

00:00 – Intro

03:12 – Why Community Is a Competitive Advantage

05:00 – The Power of Grit in Business

07:02 – Vivian’s Real Estate Journey (2004–2018 Gap Explained)

09:56 – Corporate Burnout at Apple & Transferable Skills

13:05 – Why Most Investors Pivot Too Fast

16:48 – Why Midterm Rentals Make More Strategic Sense

21:41 – The Calendar Discipline Most Hosts Ignore

25:31 – Transitioning from STR to MTR the Smart Way

30:29 – Why Vivian Built Her Own Platform

35:07 – Building Teams Without Burning Out

38:10 – Setting Boundaries & Protecting Your Time

42:05 – The 80% Confidence Rule (Just Do It)

Guest Bio:

Vivian Yip started investing in 2004 but took her journey more seriously after being inspired by a hotel owner she met at a random airport encounter in Chicago. She and her husband started to flip houses in 2018 and ended up making enough to afford to keep the real estate. She always dreamed of leaving the corporate world, so she used her steady paycheck at Apple to support their real estate goals. In 2019, she started her first short-term rental and was forced to pivot in 2020 with the pandemic. Now she runs multiple businesses focused on short-term rentals, mid-term rentals, and corporate housing, and she coaches others on the strategy behind securing profitable leases from Airbnb and beyond.

Guest Link:

Instagram.com/vivianyip_official

[e-mail]

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