Ryan Bakke, CPA

Ryan Bakke, CPA Profile Photo

CPA, Real Estate Investor, Marketer

Ryan Bakke is a CPA and the founder of TaxStrategy365.com, where he specializes in real estate tax strategy for investors. He owns three CPA firms and works with real estate professionals to help them keep more of what they earn through smart, proactive planning. Ryan has a gift for making complex tax concepts feel simple — he’s a natural storyteller who loves breaking down the stuff that makes most people’s eyes glaze over. When he’s not in the weeds of tax law, you’ll find him out on the volleyball court, softball diamond, or somewhere in the woods or on the water hunting and fishing. Oh, and he probably just finished a book.

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May 12, 2026

Short-Term Rental Tax Loophole: Offset Your W-2 Income With Cost Seg

The short term rental tax loophole is how a high-income W-2 earner or business owner can use rental losses against wages and business income without qualifying as a real estate professional. Pair it with a cost segregation study and 100% bonus depreciation, and one property can produce a first-year loss big enough to matter on a six-figure return. In this episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, sits down with Ryan Bakke, CPA, real estate investor, and founder of Tax S...