Slash Tax

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.

Slash Tax is a business podcast hosted by Heidi Henderson, with 27 episodes on record and a Required Pod Score of 80.

Heidi Henderson hosts Slash Tax, a business show with 27 episodes published.

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  Episode #31

  The Roth IRA for Capital Gains Nobody Talks About

  Sep 30, 202638 min

  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 TOPICS What 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 investment ABOUT TODD LOFGREN Todd 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 MANAGEMENT Website: https://www.alternativetaxmanagement.com/ LinkedIn: https://www.linkedin.com/in/todd-lofgren-awm/ Email: tlofgren@alternativetm.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. 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 Qualified 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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  Episode #30

  Sell Your Rentals, Skip the Tax Bill: The 1031 DST Explained

  Sep 23, 202634 min

  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 TOPICS What 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 43 ABOUT TODD LOFGREN Todd 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 MANAGEMENT Website: https://www.alternativetaxmanagement.com/ LinkedIn: https://www.linkedin.com/in/todd-lofgren-awm/ Email: tlofgren@alternativetm.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. 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 DSTs 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 property TIMESTAMPS 00:00 Tired of tenants, tired of toilets 00:40 The problem with selling appreciated real estate 01:44 Why a traditional 1031 puts you back into another property 02:20 Meet Todd Lofgren of Alternative Tax Management 05:02 Who comes looking for a DST and why 06:32 The boot problem: leftover 1031 proceeds with nowhere to go 07:38 What a Delaware Statutory Trust actually is 07:52 1988 in Delaware and the 2004 IRS ruling that opened it up 09:12 Accredited investors and the $100,000 minimum 09:48 What you actually own and how property type drives distributions 11:25 Diversifying across sponsors, locations, and asset classes 12:37 The qualified intermediary and avoiding constructive receipt 13:47 Why DSTs fill their capital raise and disappear 14:43 When cost segregation leaves you with no basis left 15:12 The due diligence gap most investors never see 18:08 Smaller trusts vs the massive conglomerate funds 20:29 The numbers: a $500,000 purchase that appreciated to $1 million 21:03 Why your debt has to come with you into the DST 22:01 How you get paid: monthly and quarterly distributions 23:42 The four to seven year horizon and expected returns 24:23 Capital gains and 25% depreciation recapture if you exit 24:49 The legacy play: step up in basis for your heirs 26:19 UPREIT liquidity windows vs zero liquidity in a DST 28:05 Why baby boomers are driving DST demand 28:40 What separates a great DST from one to avoid 30:24 When to call: before you sell, or on day 43 if you have to 32:20 How to reach Todd and final takeaways

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  Episode #28

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

  Jul 8, 202655 min

  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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  Episode #27

  Clean Books, Bigger Deductions, More Free Time: The Platform Built Just for Real Estate Investors

  May 27, 202639 minS0

  <p>What if your books were tax-ready every single day without spending hours on spreadsheets, chasing receipts, or juggling multiple bank accounts?</p><p>"Information is power."</p><p>In this episode, Heidi Henderson sits down with Mathias Korder, co-founder of Baselane, to break down the financial platform built exclusively for real estate investors. From automated bookkeeping and property-level banking to AI-powered transaction categorization with 95% accuracy, Baselane is solving the problems that have plagued rental property owners for years.</p><p>"Can you tell me your annual rate of return? There's like one person in every room that can answer...

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  Episode #26

  Cost Segregation Secrets They Don't Tell You: Why Your Cheap Report Could Cost You Everything

  Apr 29, 202644 minS0

  <p>Summary</p><p>Heidi Henderson from Engineered Tax Services discusses the complexities of cost segregation studies, emphasizing the importance of quality, methodology, and supporting documentation to maximize tax benefits and ensure IRS audit readiness.</p><p><br>Key  Topics</p>Cost segregation methodology and standardsDifferences between engineering-based and basic reportsRed flags in cost segregation studiesImportance of detailed documentation and site visitsFuture asset disposition and ongoing benefits<p><br>Takeaways</p>Cost segregation is not a commodity; quality varies significantly.The IRS has no formal standards for cost segregation studies.A detailed engineering approach provides the most support and benefit.R...

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