Most people think the path is simple: get the degree, climb the ladder, save what’s left. Lame Kinikini did the opposite. He dropped out one year before med school, went all-in on door-to-door sales, then used those skills to build a 9-figure short-term rental portfolio and help high earners legally slash their tax bills.
In this episode, Lame breaks down the real journey behind the highlight reel. From growing up in a Polynesian immigrant family and marrying young, to making $200K in sales and realizing he still didn’t own his time, to burning the boats after his father-in-law passed away unexpectedly. He talks about how he used Airbnb arbitrage to replace his income fast, scaled into management and operations, then shifted into owning the assets and becoming “the short-term rental tax guy” for high-income professionals.
We also dive into the short-term rental tax loophole, why most people misunderstand it, and how smart investors are using it to offset active income while still buying properties that actually cash flow. Lame shares how he structures deals, why bigger and better amenities win in today’s Airbnb landscape, and what changes when you see money as a tool to increase your capacity to serve—not a scoreboard.
If you’re stuck in that “comfortable” $200K income trap, curious about short-term rentals, or wondering how to turn your existing skills into a real portfolio and real freedom, this conversation will give you both the tactics and the perspective shift.
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