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/
What this episode covers
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 ...
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How a 22-Year-Old Built 70 Units From Scratch (And Why Arbitrage Is Just the Beginning)
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