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Slash Tax

Slash Tax

By: Heidi Henderson
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Slash Tax is your go-to podcast for legal tax strategies, powerful incentives, and tax-advantaged investments. Hosted by Heidi Henderson, this show is designed for high-income earners, business owners, real estate investors, and CPAs who want to cut tax bills, keep more cash, and build lasting wealth. Each episode brings expert insights, actionable strategies, and real-world examples—helping you take control of your financial future.© 2026 Heidi Henderson Economics Personal Finance
Episodes
  • The Roth IRA for Capital Gains Nobody Talks About

    The Roth IRA for Capital Gains Nobody Talks About
    Oct 1 2026
    What if a capital gain could be deferred for five years, partly discounted, and then everything it grows into came back to you tax free?Opportunity Zones started under the 2017 Tax Cuts and Jobs Act to push private investment into underserved communities. The One Big Beautiful Bill Act made them permanent and created a new generation of zones starting in 2027. In Part 2 of her conversation with Todd Lofgren of Alternative Tax Management, Heidi Henderson walks through what Opportunity Zones 2.0 actually changes and who it makes sense for.The original program had one fixed deferral date. The new version rolls. Every investment gets its own five year deferral, a 10% step up in basis if held five years, and 30% if the project sits in a rural zone, which now includes farms, ranches, and agricultural land. Hold for 10 years and the growth can be sold with no tax owed. That is why the industry calls a QOZ a Roth IRA for capital gains.Heidi also raises a difference she says nobody talks about. In a 1031 exchange, every dollar of proceeds has to roll into the next property. With a QOZ, you only reinvest the gain and you keep the rest. For investors who want out of real estate entirely, it works as a second exit after the DST strategy covered in Part 1.Todd covers what qualifies as a gain, why you have 180 days to invest it, and how some funds return capital at year five to help cover the tax bill when the deferred gain comes due. He explains why a gain triggered in the second half of 2026 can end up with close to six years of deferral, and why his team only brings on funds with a track record through multiple economic cycles.Both of them keep coming back to the same rule. Investment first, tax benefit second. A great tax incentive does not make a bad investment good.KEY TOPICSWhat an Opportunity Zone is and how each governor picks the tracts | The $160 billion invested since 2017 and what it did to household income and unemployment | Why the zones are now permanent and what is still unknown about the new tracts | The rolling five year deferral under QOZ 2.0 | The 10% step up in basis, and 30% for rural zones | Why a QOZ behaves like a Roth IRA for capital gains | QOZ 1.0 vs QOZ 2.0 | Why only the gain is reinvested, not the full sale price | 1031 exchange vs Opportunity Zone | Stock, crypto, art, and business sales as qualifying gains | The 180 day investment window | How some funds help investors pay the tax at year five through energy and real estate refinancing | Why business QOZs are rare and most funds are run by developers | Only investing what you can leave alone for 10 years | The biggest mistake: chasing the tax break without vetting the investmentABOUT TODD LOFGRENTodd Lofgren has over 25 years of experience in the financial services industry working with institutional asset managers, providing investment solutions to financial advisors and CPAs. He uses his diverse background to partner with advisors, accounting professionals, and others to deliver tax advantaged solutions for high net worth clients and small business owners. Todd lives in Berwyn, Pennsylvania with his wife Lianne and their three children, and in his free time enjoys tennis, pickleball, golf, and live music.CONNECT WITH TODD LOFGREN & ALTERNATIVE TAX MANAGEMENTWebsite: https://www.alternativetaxmanagement.com/LinkedIn: https://www.linkedin.com/in/todd-lofgren-awm/Email: tlofgren@alternativetm.comResources:Get A Free Cost Segregation Benefit Analysis Here:https://portal.engineeredtaxservices.com/get-started?ref_id=njg2zdvIRS Audit Technique Guidelines:https://www.irs.gov/pub/irs-pdf/p5653.pdfBaselane Affiliate Link:https://baselane.com/engineeredtaxservicesBaselane Promo Code: ENGINEERING6Use promo code ENGINEERING6 to receive 6 months of free Baselane Smart premium tier. Enter the code when prompted to subscribe to Baselane Smart.Links:LinkedIn - linkedin.com/in/heidihendersonInstagram - instagram.com/slashtaxwithheidiFacebook - facebook.com/slashtaxwithheidihttps://app.411core.com/r/XCBLEARN MOREEngineered Tax Services has helped investors and business owners unlock millions in tax savings for nearly 25 years through cost segregation, R&D credits, and energy incentives like 179D and 45L.👉 Visit engineeredtaxservices.comQualified Opportunity Zone funds carry risk, fees, illiquidity, and strict compliance requirements. Any figures discussed are illustrative and not a guarantee of future results. Nothing in this episode is investment, tax, or legal advice. Evaluate any QOZ investment with a qualified tax, legal, and investment professional before acting.Subscribe to Slash Tax | Leave a review | Share with someone sitting on a big capital gain
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    38 mins
  • Sell Your Rentals, Skip the Tax Bill: The 1031 DST Explained

    Sell Your Rentals, Skip the Tax Bill: The 1031 DST Explained
    Sep 23 2026
    You have owned the property for years. It has appreciated. You have depreciated it down to almost nothing. Now you are tired of tenants, tired of toilets, tired of property managers, tired of making decisions about roofs and HVAC systems and lease renewals. So you decide to sell, and then your CPA tells you exactly how much tax you are going to owe.Most investors know a 1031 exchange defers that gain. The catch is that a traditional 1031 puts you right back into another piece of real estate you have to identify, acquire, own, and manage. Heidi Henderson sits down with Todd Lofgren of Alternative Tax Management to walk through the option a surprising number of investors have never heard of. The Delaware Statutory Trust.A DST lets you roll your proceeds into fractional ownership of a professionally managed portfolio of properties. It satisfies the 1031 requirements, it keeps you invested in real estate, and it moves the day to day management to a sponsor. Todd calls it the exit ramp from the managerial role.Todd and Heidi get into the mechanics. What you actually own, how sponsors structure the trust, why the debt on your old property has to come with you, and how distributions come back tax friendly because depreciation starts over. They also cover what you give up: zero liquidity, no control, and a four to seven year hold. If you ever cash out, the capital gains and 25% depreciation recapture from that original property follow you the entire way.Todd also breaks down the due diligence side, which is where most investors are flying blind. Boutique shops with creative marketing and nothing behind the fact sheets. Offerings that hit their capital raise and vanish. Why real inventory matters when your proceeds are ready to move.KEY TOPICSWhat a Delaware Statutory Trust is, its 1988 origin in Delaware, and the 2004 IRS ruling that made DSTs valid 1031 replacement property in all states | Sponsors, accredited investors, and the $100,000 typical minimum | The boot problem and how leftover 1031 proceeds avoid a tax bill | Diversifying across sponsors, locations, and asset classes from multifamily to self storage to net lease | Why the qualified intermediary process stays the same and why constructive receipt kills the exchange | Why a low basis after cost segregation makes selling so expensive | A $500,000 purchase that appreciated to $1 million, and why your debt has to be replaced inside the DST | Monthly and quarterly distributions and why the income is tax friendly | The four to seven year horizon and what happens at full cycle | What it costs to exit: capital gains plus 25% depreciation recapture | The legacy play and the step up in basis for heirs | Zero liquidity in a DST vs UPREIT liquidity windows | How to tell a quality DST from one to avoid | Why calling before you sell beats calling on day 43ABOUT TODD LOFGRENTodd Lofgren has over 25 years of experience in the financial services industry working with institutional asset managers, providing investment solutions to financial advisors and CPAs. Todd uses his diverse background to partner with advisors, accounting professionals, and others to deliver tax advantaged solutions for high net worth clients and small business owners. He lives in Berwyn, Pennsylvania with his wife Lianne and their three children, and in his free time enjoys tennis, pickleball, golf, and live music.CONNECT WITH TODD LOFGREN & ALTERNATIVE TAX MANAGEMENTWebsite: https://www.alternativetaxmanagement.com/LinkedIn: https://www.linkedin.com/in/todd-lofgren-awm/Email: tlofgren@alternativetm.comResources:Get A Free Cost Segregation Benefit Analysis Here:https://portal.engineeredtaxservices.com/get-started?ref_id=njg2zdvIRS Audit Technique Guidelines:https://www.irs.gov/pub/irs-pdf/p5653.pdfBaselane Affiliate Link:https://baselane.com/engineeredtaxservicesBaselane Promo Code: ENGINEERING6Use promo code ENGINEERING6 to receive 6 months of free Baselane Smart premium tier. Enter the code when prompted to subscribe to Baselane Smart.Links:LinkedIn - linkedin.com/in/heidihendersonInstagram - instagram.com/slashtaxwithheidiFacebook - facebook.com/slashtaxwithheidihttps://app.411core.com/r/XCBLEARN MOREEngineered Tax Services has helped investors and business owners unlock millions in tax savings for nearly 25 years through cost segregation, R&D credits, and energy incentives like 179D and 45L.👉 Visit engineeredtaxservices.comDSTs are investments. They carry risk, fees, liquidity restrictions, and specific tax requirements. Any return figures discussed are historical or hypothetical and are not a guarantee of future performance. Nothing in this episode is investment, tax, or legal advice. Evaluate any DST with a qualified tax, legal, and investment professional before acting.Subscribe to Slash Tax | Leave a review | Share with an investor who is ready to stop managing propertyTIMESTAMPS00:00 Tired of tenants, tired of toilets00:40 The problem with selling appreciated real estate01:44 Why ...
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    34 mins
  • Active vs Passive: Why Your Rental Losses Can't Touch Your W-2

    Active vs Passive: Why Your Rental Losses Can't Touch Your W-2
    Sep 9 2026

    You bought the rental. You ran the cost segregation study. Now you have a six figure paper loss sitting on your return and it does nothing for the tax coming out of your paycheck.

    In this solo deep dive, Heidi Henderson breaks down the rule that decides all of it. Active versus passive activity. The IRS treats every rental as passive by default, so those losses get trapped and never offset your W-2 income unless you cross into material participation. You don't get to step over that line. You have to earn your way across it.

    Heidi walks through both routes. Real estate professional status takes 750 hours a year plus more than half of your total working time, which is close to impossible if you have a full time job. She also kills the myth that you need a real estate license to qualify. The short term rental loophole is the far more realistic path. If your average stays are seven days or less, the IRS stops treating the property as a rental at all, and 100 documented hours can be enough to trigger active treatment.

    She also covers the play most investors miss completely. On a joint return, only one spouse has to materially participate for the whole portfolio to go active.

    Then the five mistakes that blow the strategy apart, including the personal use limit that quietly wipes out every dollar of depreciation, and why documentation is the only thing standing between you and a disallowed deduction under audit.

    KEY TOPICS

    • Why the IRS classifies every rental as passive by default
    • The 750 hour rule for real estate professional status and the more than 50% catch
    • Why a real estate license is not required for REPS
    • How the short term rental loophole works and the seven day average stay test
    • The 500 hour test versus the 100 hour test and the "more than anyone else" requirement
    • The married filing jointly strategy that unlocks an entire portfolio
    • Five ways investors destroy the STR strategy: misclassification, stacked lease extensions, personal use over 14 days or 10% of rental days, untracked helper hours, and local bans
    • Why short term rentals depreciate over 39 years instead of 27.5
    • $64,000 versus $795,000 in year one depreciation on the same building
    • Why structure comes first and cost segregation second

    ABOUT HEIDI HENDERSON

    Heidi Henderson is an Executive Vice President at Engineered Tax Services and the host of Slash Tax. She has spent over 25 years in the tax world and is an active real estate investor herself, helping business owners and real estate investors apply specialty tax incentives like cost segregation, R&D credits, and energy incentives, legally and ethically.

    Resources:

    Get A Free Cost Segregation Benefit Analysis Here:

    https://portal.engineeredtaxservices.com/get-started?ref_id=njg2zdv

    IRS Audit Technique Guidelines:

    https://www.irs.gov/pub/irs-pdf/p5653.pdf

    Baselane Affiliate Link:

    https://baselane.com/engineeredtaxservices

    Baselane Promo Code: ENGINEERING6

    Use promo code ENGINEERING6 to receive 6 months of free Baselane Smart premium tier. Enter the code when prompted to subscribe to Baselane Smart.

    Links:

    LinkedIn - linkedin.com/in/heidihenderson

    Instagram - instagram.com/slashtaxwithheidi

    Facebook - facebook.com/slashtaxwithheidi

    https://app.411core.com/r/XCB

    LEARN MORE

    Engineered Tax Services has helped investors and business owners unlock millions in tax savings for nearly 25 years through cost segregation, R&D credits, and energy incentives like 179D and 45L.

    👉 Visit engineeredtaxservices.com

    Subscribe to Slash Tax | Leave a review | Share with an investor whose losses are stuck on paper
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    28 mins
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