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Slash Tax

Slash Tax

De : 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 Economie Finances privées
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  • 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 min
  • 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 min
  • Mr. Wonderful's Tax Firm Is Breaking the Mold (Here's How)

    Mr. Wonderful's Tax Firm Is Breaking the Mold (Here's How)
    Jul 8 2026

    This episode breaks down the difference between tax preparation and tax strategy using one of the best analogies we've heard: your CPA is like the grocery store cashier ringing you up accurately, but nobody walked the aisles with you finding coupons and better deals. TaxHive is that missing piece. With their average client saving $60-70K in identified tax savings, a money-back guarantee, and Kevin O'Leary as an equity partner, this conversation will change how you think about your tax team.

    Host Heidi Henderson sits down with Devan Egan, President of TaxHive, a Kevin O'Leary-backed tax strategy firm that's redefining how business owners and real estate investors approach tax planning. Devan shares how TaxHive identified a massive gap between tax compliance and tax strategy, and why most business owners are unknowingly overpaying simply because their CPA was never hired to find savings.

    KEY TOPICS
    Tax strategy vs tax compliance and why most CPAs only do one | How Kevin O'Leary became an equity partner in TaxHive | The grocery store cashier analogy for understanding your CPA | Why 86% of CPA firms have fewer than 10 employees and what that means for you | Most commonly missed strategies: Augusta Rule, S-corp elections, cost segregation, R&D credits, solo 401Ks, oil and gas | Dynasty strategies for high-impact savings | TaxHive's money-back guarantee model | Why AI can help but cannot replace licensed tax professionals | Forward-looking tax planning vs rearview mirror filing | How TaxHive scales with technology while maintaining personal service

    ABOUT DEVAN EGAN
    Devan Egan is an entrepreneur and business strategist serving as President of TaxHive, where he leads the company's vision, business development, and strategic partnerships. With a background in real estate sales and marketing, Devan identified a critical gap between tax compliance and proactive tax strategy for Main Street business owners. He also owns three Club Pickleball USA locations in Utah and leads Club Mastermind, a private network of 125+ clubs across the U.S. and Canada.

    CONNECT WITH DEVAN EGAN & TAXHIVE

    Website: taxhive.com
    Instagram: @realtaxhive
    Email: devan@taxhive.com

    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.

    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

    Links:
    LinkedIn - https://linkedin.com/in/heidihenderson
    Instagram - https://www.instagram.com/slashtaxwithheidi/
    Facebook - https://www.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 a business owner ready to stop overpaying

    TIMESTAMPS
    00:00 Introduction to TaxHive and Devan Egan
    03:07 Identifying the gap between compliance and strategy
    05:55 Why specialized tax knowledge matters for real estate investors
    09:14 Democratizing the tax code for every taxpayer
    12:05 The grocery store cashier analogy: CPA compliance vs strategy
    15:13 How Kevin O'Leary became an equity partner
    18:15 Maintaining service quality while scaling to thousands of clients
    27:49 Technology as the backbone of client experience
    28:53 TaxHive's money-back guarantee and ROI model
    32:07 Top missed tax strategies: Augusta Rule, S-corp, cost seg, R&D
    36:27 Navigating complex strategies: Is the juice worth the squeeze?
    40:34 AI in tax planning: Helpful tool but not a replacement
    46:07 The onus is on the taxpayer: Why documentation matters
    49:09 Serving clients nationwide through technology and portals
    53:32 Outro and how to connect with TaxHive
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    55 min
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