How a 22-Year-Old Built 70 Units From Scratch (And Why Arbitrage Is Just the Beginning) episode artwork

EPISODE · Mar 6, 2026 · 36 MIN

How a 22-Year-Old Built 70 Units From Scratch (And Why Arbitrage Is Just the Beginning)

from STR Like The Best · host Michael Chang

Most people wait until they feel "ready" to build something real. Hailee Marie started at 19, during a pandemic, when everyone else was running the other way.In this episode, I sit down with Hailie Marie, short-term rental operator and angel investor, to talk about how she scaled a 70-unit remote arbitrage portfolio from scratch and why she's now using that cash flow to build long-term wealth.Hailie built something most operators never do: a business that runs without her. Nine VAs, a full tech stack, 24/7 coverage, and AI handling guest communications around the clock. She did it starting with three units in Austin at 19 years old.We break down:How Hailie scaled from 3 units to 70 using arbitrage as a tool, not a destination, and what she's building toward nextThe exact tech stack running her remote portfolio, including HostAway, PriceLabs, TrueV, Bestie AI, Kendo AI, and Phantom AIWhy she uses 9 VAs to run 70 units remotely and how she structured 24/7 coverage without burning out her teamHow AI is training her customer service and cold calling teams in real time, and why she says it improves humans rather than replacing themThe one habit every operator should start now: recording everything, because your future AI tools will need that dataWhy her tax bill was the wake-up call that's pushing her from arbitrage into ownership, and what bonus depreciation changes everythingThe bottom line: Arbitrage can make you cash flow. But the operators who win long-term are the ones using that cash flow to buy assets, build systems, and invest in things that compound.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most people wait until they feel "ready" to build something real. Hailee Marie started at 19, during a pandemic, when everyone else was running the other way. In this episode, I sit down with Hailie Marie, short-term rental operator and angel investor, to talk about how she scaled a 70-unit remote arbitrage portfolio from scratch and why she's now using that cash flow to build long-term wealth. Hailie built something most operators never do: a business that runs without her. Nine VAs, a full ...

NOW PLAYING

How a 22-Year-Old Built 70 Units From Scratch (And Why Arbitrage Is Just the Beginning)

0:00 36:45

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of STR Like The Best?

This episode is 36 minutes long.

When was this STR Like The Best episode published?

This episode was published on March 6, 2026.

What is this episode about?

Most people wait until they feel "ready" to build something real. Hailee Marie started at 19, during a pandemic, when everyone else was running the other way.In this episode, I sit down with Hailie Marie, short-term rental operator and angel...

Is there a transcript available for this episode?

Yes, a full transcript is available for this episode. You can read the complete transcript on the episode page.

Can I download this STR Like The Best episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.
URL copied to clipboard!