From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like episode artwork

EPISODE · May 29, 2026 · 47 MIN

From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like

from STR Like The Best · host Michael Chang

From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks LikeMost high-income couples know they're overpaying on taxes. Very few actually do something about it.In this episode, Michael sits down with Ashish and Smita, a Bay Area dentist and finance professional, to walk through their first 9 months in the STR Like The Best program, from their first property in Colorado to filing the most satisfying tax return of their lives.This isn't a highlight reel. It's the real story, including the self-doubt, the market search, the launch, the guests who left the hot tub uncovered, and the moment their CPA told them to expect a very large refund.We break down:How a $180K tax bill during Ashish's nose surgery recovery sent them down a rabbit hole that changed everythingWhy they chose Colorado over Hawaii, and how the mentorship helped them stop overthinking market selection and just moveWhat their first season actually looked like, covering the mortgage in off-peak months and heading into their best month everHow they got $94K back in federal taxes and $16K from California in their very first year with one propertyWhy "done for you" STR programs legally cannot qualify you for the tax benefits, and what the IRS actually requiresThe 4 things Ashish and Smita would tell their pre-July 2024 selves if they were still on the fenceThe bottom line: the STR tax loophole is real, it works, and it works best when you stop waiting for the perfect moment and just do the work.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/

From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like Most high-income couples know they're overpaying on taxes. Very few actually do something about it. In this episode, Michael sits down with Ashish and Smita, a Bay Area dentist and finance professional, to walk through their first 9 months in the STR Like The Best program, from their first property in Colorado to filing the most satisfying tax return of their lives. This isn't a highlight reel. It's the real...

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From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like

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This episode is 47 minutes long.

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This episode was published on May 29, 2026.

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From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks LikeMost high-income couples know they're overpaying on taxes. Very few actually do something about it.In this episode, Michael sits down with Ashish and Smita, a Bay...

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