What if the biggest tax advantage in real estate is one most investors have never heard of?
In this episode, I sit down with Yonah Weiss, Business Director at Madison SPECS, the largest national cost segregation company in the country. Yonah has helped property owners save over a billion dollars in taxes, spent fifteen years as a teacher before getting into real estate, and hosts the top-rated Weiss Advice podcast.
We break down exactly what cost segregation is, how it works, and why it can mean the difference between a massive tax bill and paying nothing at all. Yonah also explains how bonus depreciation works, who can actually use these deductions, and what the short-term rental loophole means for W-2 earners who want to pay less to the IRS.
Timestamp
00:00 Intro
02:58 Why most real estate investors have never heard of cost segregation
04:31 How closing a deal saved me nearly $100,000 in taxes
05:59 What is depreciation and how does it work in real estate investing
07:23 What is cost segregation and how does the engineering study work
10:04 The five year and fifteen year depreciation buckets explained
11:40 What is bonus depreciation and how does it supercharge your tax savings
18:29 How limited partners in syndications benefit from cost segregation
20:21 What depreciation recapture actually means when you sell a property
24:41 What property size makes cost segregation worth doing
26:21 The short-term rental loophole for W-2 earners explained
29:53 Can the short-term rental strategy actually replace your W-2 income
31:26 Active vs passive real estate investing and how cost seg applies to both
32:24 How to build a powerful network in commercial real estate through LinkedIn
What We Cover
- What cost segregation is and how it accelerates your real estate tax deductions
- How bonus depreciation works and what changed with the One Big Beautiful Bill
- Who can actually use cost seg write-offs and the real estate professional status rule
- How limited partners in syndications benefit from cost segregation
- What depreciation recapture means and how to reduce or eliminate it
- The short-term rental loophole and how W-2 earners can use it
- How Yonah built a nationally recognized brand through LinkedIn without a single sales pitch
Key Takeaways
- Cost segregation lets you pull forward years of depreciation deductions into year one
- Bonus depreciation is back at 100% permanently after the One Big Beautiful Bill passed in 2025
- Unless you or your spouse qualify as a real estate professional, depreciation offsets passive income only, not your W-2
- The short-term rental loophole lets self-managing owners use losses to offset W-2 income with just 100 hours a year
- Any property over $200,000 in purchase price is worth getting a cost seg estimate on
- Depreciation recapture does not mean paying back your deductions; it means paying a lower tax rate on a portion of your gain
- Passive losses you never used do not disappear; they can offset gains when the property sells
Connect With Yonah Weiss
- https://www.yonahweiss.com/
- https://www.instagram.com/yonahweiss/
- https://www.linkedin.com/in/cost-segregation-yonah-weiss/
- https://twitter.com/YonahWeiss
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