Slash Tax

Heidi Henderson
  • 5.0 (1)
  • Investing
  • Updated Biweekly

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.

  1. Sep 9

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

    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 defaultThe 750 hour rule for real estate professional status and the more than 50% catchWhy a real estate license is not required for REPSHow the short term rental loophole works and the seven day average stay testThe 500 hour test versus the 100 hour test and the "more than anyone else" requirementThe married filing jointly strategy that unlocks an entire portfolioFive 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 bansWhy short term rentals depreciate over 39 years instead of 27.5$64,000 versus $795,000 in year one depreciation on the same buildingWhy 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

  2. Jul 8

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

    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 TOPICSTax 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 EGANDevan 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.comInstagram: @realtaxhiveEmail: 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=njg2zdvIRS Audit Technique Guidelines: https://www.irs.gov/pub/irs-pdf/p5653.pdf Links:LinkedIn - https://linkedin.com/in/heidihendersonInstagram - https://www.instagram.com/slashtaxwithheidi/Facebook - https://www.facebook.com/slashtaxwithheidi/https://app.411core.com/r/XCB LEARN 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.com Subscribe to Slash Tax | Leave a review | Share with a business owner ready to stop overpaying TIMESTAMPS00:00 Introduction to TaxHive and Devan Egan03:07 Identifying the gap between compliance and strategy05:55 Why specialized tax knowledge matters for real estate investors09:14 Democratizing the tax code for every taxpayer12:05 The grocery store cashier analogy: CPA compliance vs strategy15:13 How Kevin O'Leary became an equity partner18:15 Maintaining service quality while scaling to thousands of clients27:49 Technology as the backbone of client experience28:53 TaxHive's money-back guarantee and ROI model32:07 Top missed tax strategies: Augusta Rule, S-corp, cost seg, R&D36:27 Navigating complex strategies: Is the juice worth the squeeze?40:34 AI in tax planning: Helpful tool but not a replacement46:07 The onus is on the taxpayer: Why documentation matters49:09 Serving clients nationwide through technology and portals53:32 Outro and how to connect with TaxHive

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

  3. May 27

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

    What if your books were tax-ready every single day without spending hours on spreadsheets, chasing receipts, or juggling multiple bank accounts? "Information is power." 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. "Can you tell me your annual rate of return? There's like one person in every room that can answer that question." Heidi and Mathias dig into how the platform consolidates every LLC, every property, and every transaction into one login. They talk about why most investors can't answer the simple question of what their actual ROI is, and how having clean, organized financial data changes everything from tax strategy to long-term wealth building. Whether you own two doors or two hundred, this conversation covers why the right financial infrastructure is the foundation of every smart real estate investment. "What you get in is what you get out. Garbage in, garbage out." What You'll Learn in This Episode: How Baselane consolidates banking, bookkeeping, and rent collection into one platform designed specifically for real estate investors. Why clean financial data is the foundation of every effective tax strategy and how messy books lead to missed deductions. How AI-powered transaction tagging works and why it's replacing hours of manual categorization. The simple onboarding process for investors who already have existing bank accounts, properties, and years of transaction history. How Baselane's receipt capture tool matches expenses to transactions automatically. Why the platform is free to start and how it makes money without hidden fees. What's coming next with AI-driven financial intelligence that proactively identifies savings opportunities for investors. "A customer needs to get value within the first five minutes." Chapters: 00:00 Introduction to the Slash Tax Podcast and Baselane Partnership 02:59 Why Most Investors Don't Actually Know Their ROI 06:06 How Baselane Automates Banking, Bookkeeping, and Rent Collection 09:03 Onboarding: Bringing Existing Accounts and History Into the Platform 12:15 Receipt Management and AI-Powered Transaction Matching 15:03 Customer Support Built by Real Estate Finance Experts 18:09 The Future of AI-Driven Financial Intelligence for Investors 19:55 Growth, Market Positioning, and Who Baselane Serves 22:03 How to Get Started and Final Takeaways "We want to be a CFO in our customers' pockets." 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=njg2zdvIRS Audit Technique Guidelines: https://www.irs.gov/pub/irs-pdf/p5653.pdf Links:LinkedIn - https://linkedin.com/in/heidihendersonInstagram - https://www.instagram.com/slashtaxwithheidi/Facebook - https://www.facebook.com/slashtaxwithheidi/

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

  4. Apr 30

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

    Summary 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. Key  Topics 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 benefitsTakeaways 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.Red flags include no land value, no site visit, and lack of detail.Choosing a licensed engineering firm ensures audit protection.Chapters 00:00 Understanding Cost Segregation Pricing Variability 03:02 Defining Quality in Cost Segregation Studies 06:00 IRS Guidelines and Methodologies for Cost Segregation 08:52 Key Elements of a Quality Cost Segregation Study 12:11 Comparing Engineering-Based Studies to Basic Reports 15:03 Identifying Red Flags in Cost Segregation Reports 18:14 The Importance of Detailed Engineering in Cost Segregation 21:04 Understanding Partial Asset Disposition (PAD) 23:59 Evaluating Cost Segregation Providers 26:50 The Long-Term Value of Quality Cost Segregation 29:58 Questions to Ask Your Cost Segregation Provider 33:08 The Risks of Low-Cost Cost Segregation Studies 36:04 Final Thoughts on Cost Segregation ResourcesGet 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.pdf Links:LinkedIn - https://www.linkedin.com/in/heidihenderson/Instagram - https://www.instagram.com/slashtaxwithheidi/Facebook - https://www.facebook.com/slashtaxwithheidi/

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

  5. Apr 15

    LLC Structuring Secrets For Real Estate & Digital Nomads: Bobby Casey on International Tax Strategy

    SummaryExplore international tax strategies, entity structuring, and how entrepreneurs can optimize their global presence to reduce tax liabilities and enhance wealth preservation. Featuring expert Bobby Casey, founder of Business Anywhere.io. Key TopicsInternational tax optimizationEntity structuring for entrepreneursLiving abroad and tax benefits GuestBobby CaseyWebsite - https://businessanywhere.ioYouTube - https://www.youtube.com/c/BusinessAnywhere "Income tax fuels almost nothing in local communities""Tax incentives drive economic growth and investment" "The U.S. is the biggest tax haven in the world" Chapters00:00 Introduction to Tax Strategies and International Consulting11:02 Bobby's Entrepreneurial Journey and Tax Optimization19:58 Business Anywhere: Services and Solutions for Entrepreneurs28:03 Living Abroad: Tax Benefits and Opportunities for Americans32:46 Understanding Tax Residency and Vital Interest34:41 Maximizing Tax Benefits for Entrepreneurs36:04 Navigating Foreign Tax Credits and Exclusions38:34 Exploring Global Tax Strategies: Costa Rica and Beyond40:37 Puerto Rico: Tax Benefits and Residency Requirements42:57 Mexico's Unique Tax Residency Rules45:06 The Gray Areas of International Tax Law47:04 Identifying the Ideal Client for International Tax Consulting51:44 The Non-Habitual Resident Tax Regime in Portugal54:42 Complexities of LLCs and International Taxation57:27 The Rise of Digital Nomadism and Remote Work01:00:03 Exploring Business Structures Globally01:00:32 Maximizing Tax Incentives and Strategies01:01:20 Slash Tax (4).mp4 ResourcesBusiness Anywhere.io - https://businessanywhere.ioIRS Form 2555 - Foreign Earned Income Exclusion - https://www.irs.gov/forms-pubs/about-form-2555U.S. Tax Treaties and International Tax Law - https://www.irs.gov/businesses/international-businessesCosta Rica Residency and Tax Benefits - https://costarica.comPortugal Non-Habitual Resident (NHR) Regime - https://portugal.gov.pt/en/services/non-habitual-residents-regimeCongressional Budget Office (CBO) - https://www.cbo.gov

    LLC Structuring Secrets For Real Estate & Digital Nomads: Bobby Casey on International Tax Strategy

  6. Mar 25

    Why Your CPA is Busier (and More Expensive) Than Ever: Inside Public Accounting Data Reveals What's Really Happening

    SummaryThis episode explores transformative trends in the CPA industry, including staffing shortages, growth in advisory services, technological advancements such as AI, and private equity influence. Hosted by Heidi Henderson with Chelsea Summers, the discussion provides valuable insights for CPA firms, business owners, and investors on navigating industry changes effectively. Key Topics Staffing shortages and succession concernsGrowth of advisory and strategic servicesImpact of AI and technology on efficiencyPrivate equity influence on firm consolidationShift towards specialization and niche marketsTakeaways Firms that adapt to pricing, staffing, and specialization stay profitableAdvisory services now generate over 32% of revenue, up from 19% in 2015Technology investments, including AI, are transforming firm operationsPrivate equity-backed firms are more profitable, but not drastically different yetOffshoring is increasingly common, with 47% of firms using offshore FTEsChapters00:00 Introduction to Data and Strategy in Accounting04:47 Shifts in the Accounting Industry08:07 The Rise of Advisory Services09:54 Specialization in Accounting Firms13:14 Impact of Technology on CPA Firms15:17 The Role of AI in Accounting16:36 Staffing Challenges and Opportunities17:20 Trends in Partner Age and Accounting Graduates19:19 Billing Structures and Profitability24:07 Mergers and Acquisitions in the CPA Space26:51 Private Equity's Influence on Accounting Firms32:59 Emerging Trends and Future Outlook ResourcesEngineered Advisory - https://engineeredadvisory.com/Heidi Henderson (LinkedIn) - https://www.linkedin.com/in/heidihenderson/ Guest LinksLinkedIn - https://www.linkedin.com/in/chelseasummers/Inside Public Accounting (IPA) - https://insidepublicaccounting.com/

  7. Feb 18

    Tax Efficient Retirement Planning for High Earners: Rob Burnette on Social Security, IRAs, and Long-Term Care

    SummaryIn this episode of the Slash Tax podcast, host Heidi Henderson and guest Rob Burnette discuss the intersection of tax strategies and financial planning. They explore how to effectively combine smart financial planning with tax-efficient strategies to support long-term goals, particularly in retirement and wealth building. Rob shares his unique journey from engineering to finance, emphasizing the importance of problem-solving in financial consulting. The conversation also addresses the challenges faced by high-income earners, the role of insurance in wealth building, and the impact of legislative changes on taxation. Listeners gain insights into navigating the complexities of financial planning and tax strategies, ensuring they are well-prepared for their financial futures. Takeaways Combining financial planning with tax-efficient strategies is crucial.Engineering problem-solving skills can be applied to finance.Each client presents a unique financial puzzle to solve.There is no one-size-fits-all solution in financial planning.Planning for longevity and healthcare costs is essential.High-income earners face unique challenges in tax planning.Insurance can be a valuable tool for wealth building.Parents should consider the impact of college funding on retirement.Legislative changes can significantly affect tax strategies.Understanding the market's response to political changes is important for investors.Chapters00:00 Introduction to Tax Strategies and Financial Planning03:09 Rob Burnette's Journey from Engineering to Finance05:57 The Importance of Problem Solving in Financial Consulting09:12 Bridging the Gap Between Tax and Financial Advisors12:07 Planning for Longevity and Healthcare Costs15:15 Strategies for High-Income Earners17:55 Tax-Efficient Investment Approaches22:28 Tax-Efficient Investment Strategies24:27 Insurance as a Financial Tool27:57 Planning for Long-Term Care30:44 Funding Education and Wealth Transfer33:01 Navigating Financial Planning for Adult Children35:55 Understanding Legislative Changes and Their Impact40:21 Investment Strategies Amid Political Changes About Rob BurnetteRob leads Outlook Financial Center in case design, investment management, and daily operations. He has worked in financial services since 1985 and is licensed to offer investment advice and insurance products. As a registered tax preparer with the IRS, Rob participates in the Annual Filing Season Program and is certified as a National Social Security Advisor. He graduated from the U.S. Naval Academy with a Bachelor of Science in Electrical Engineering, earned an MBA from the University of New Haven, and holds a Financial Planning certificate from Kaplan University. Rob’s professional memberships include the International Association of Registered Financial Consultants, Million Dollar Round Table - Court of the Table, and Ed Slott’s Master Elite IRA Advisor Group. He has contributed to many publications, including USA Today, Barron’s, Forbes, MarketWatch, WDTN Dayton, and WHIO Dayton. He is a 2017 Alumnus of Leadership Troy, Ohio, and is passionate about supporting kids' sports programs, 4H, and FFA.Connect with Rob BurnetteRob's Website: https://outlookfc.com LinkedIn: https://www.linkedin.com/company/outlook-financial-center/ Facebook: https://www.facebook.com/OutlookFinancialCenterLLC/ Learn 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.comSubscribe to Slash Tax | Leave a review | Share with business owners ready to find better accounting partners Tax strategy isn't just about saving money; it's about finding the right partners who can help you build wealth. Host: Heidi Henderson | Sponsor: Engineered Tax Services

  8. Feb 4

    How to Choose the Right CPA in 2026: Blake Oliver on AI, Private Equity, and Better Tax Advice

    Slash Tax Podcast – Blake Oliver (Earmark CPE & The Accounting Podcast) Join host Heidi Henderson for an essential conversation with Blake Oliver, CPA, founder of Earmark CPE and host of The Accounting Podcast. Blake shares insider insights into the dramatic changes reshaping accounting and their implications for taxpayers and business owners. From musician to Starbucks barista to CPA to tech entrepreneur, Blake's journey gives him a unique perspective on what's broken in traditional accounting and how technology is creating solutions. He reveals why CPAs are retiring en masse, how AI will transform the profession, and what to look for when choosing an accounting partner who can help slash your tax bill. Key Topics The CPA shortage crisis and retirement wave are hitting the profession Why traditional accounting firms burn out talented CPAs  The shift from compliance to advisory services How to evaluate if your CPA is actually saving you money Finding specialized CPAs vs generalist firms AI's role in accounting: Excel comparison and what's comingPrivate equity takeover of accounting firms The rise of fractional CFOs and specialized boutique firms Earmark CPE: Free NASBA-approved CPE through podcasts YouTube and content marketing for professional services Fixed-fee vs billable hour pricing models Why giving away knowledge attracts better clientsAbout Blake Oliver Blake Oliver is a CPA, entrepreneur, and host of The Accounting Podcast. He founded Earmark CPE, a platform allowing accountants to earn free NASBA-approved CPE credits by listening to podcasts—transforming how CPAs stay current. Blake studied cello at Northwestern University and performed with the San Francisco Youth Symphony before the Great Recession redirected him to accounting. After working at Starbucks, he transitioned into bookkeeping, discovered his passion for accounting and technology, worked in public accounting, led firms, and eventually sold his practice to focus on technology, education, and media. He uniquely understands both what firms struggle with and what clients need. Connect with Blake OliverBlake's Website: www.blakeoliver.com Earmark CPE: earmarkcpe.com The Accounting Podcast: theaccountingpodcast.com LinkedIn: linkedin.com/in/blaketoliver/ Twitter/X: x.com/BlakeTOliver YouTube: youtube.com/@BlakeTOliver 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.comSubscribe to Slash Tax | Leave a review | Share with business owners ready to find better accounting partners Tax strategy isn't just about saving money—it's about finding the right partners who can help you build wealth. Host: Heidi Henderson | Sponsor: Engineered Tax Services

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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.

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  • Creator
    Heidi Henderson
  • Years Active
    2025 - 2026
  • Episodes
    26
  • Rating
    Clean
  • Copyright
    © 2026 Heidi Henderson

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