Rollover vs Traditional IRA: Key Differences

Self-directed IRAs [SDIRAs] are powerful But they’re not a free for all A Self-Directed IRA lets you invest beyond stocks and mutual funds in things like ✅️ Private lending ✅️ Real Estate ✅️ Precious Metals ✅️ Tax Liens & Tax Deeds ✅️ Private Equity Great tools But here’s the part many people miss The IRS has very specific rules about what’s allowed and who you can do business with Break those rules You can blow up the entire IRA That means Taxes Penalties And a very bad day SDIRAs are incredible wealth-building tools But like any powerful tool You have to know how to use it

100% bonus depreciation is back. It changes acquisition math — and it changes which DSCR terms actually serve the strategy. If your tax plan depends on a specific hold period, your loan terms need to align with that. Prepayment structure, IO periods, and rate adjustment timelines all interact with a depreciation strategy. Most lenders present the loan in isolation. The structure conversation includes the full picture.

I’m seeing some #deals where the earnout isn’t paid in cash, but extra shares. 🤔 That raises a surprisingly tricky #tax question. The deal structure looks like this: at completion, the seller receives shares plus a contingent earnout. If the earnout is satisfied, the seller is paid in further shares. The big question becomes whether those future shares can also enjoy scrip‑for‑scrip treatment. As we all know, applying two tax regimes is more fun than just one. If the earnout qualifies as a look‑through earnout right (LTER) – think future benefits not reasonably ascertainable, underlying asset was an active asset, benefits within 5 years, contingent on economic performance etc. etc - the answer is usually yes. The #ATO says so in PBR 1052214930033. They’ve also confirmed that the ‘single arrangement’ requirement can be satisfied when shares are exchanged in two stages (ATO ID 2002/274). But when the earnout doesn’t qualify as an LTER, things get less friendly. The earnout becomes a separate CGT asset under TR 2007/D10. That separate asset is treated as ‘ineligible proceeds’ (ATO ID 2002/100), meaning it’s carved out of the rollover 😬. 📌Takeaway: Earnouts can absolutely be paid in shares — but they’re only tax‑effective if they qualify as an LTER. Otherwise, you’re outside the rollover, and nobody enjoys that. #AustralianBusiness #DealMaking

I see this mistake all the time with 1031 exchanges. Most investors think it’s just about avoiding taxes. It’s not. It’s about keeping your money working instead of giving a big portion away in capital gains. Another big mistake? Waiting too long to plan. If you don’t structure it before you sell, it’s already too late. And many people rush to buy any property just to meet the deadline, instead of using the exchange to move into something better. A 1031 isn’t just a tax move. It’s a strategy move. If you’re selling a property soon, make sure you’re thinking about it the right way.

I see this mistake all the time with 1031 exchanges. Most investors think it’s just about avoiding taxes. It’s not. It’s about keeping your money working instead of giving a big portion away in capital gains. Another big mistake? Waiting too long to plan. If you don’t structure it before you sell, it’s already too late. And many people rush to buy any property just to meet the deadline, instead of using the exchange to move into something better. A 1031 isn’t just a tax move. It’s a strategy move. If you’re selling a property soon, make sure you’re thinking about it the right way.

Most investors take bonus depreciation… but forget about depreciation recapture when they sell. Learn how Cost Seg + 1031 + Step-Up can legally eliminate it. Full breakdown here: https://lnkd.in/g8mNrBGy #RealEstateTax #1031Exchange #DepreciationRecapture

Depreciation recapture myths. Many investors believe that a 1031 exchange eliminates depreciation recapture. That is not the case. Section 1031 allows investors to defer depreciation recapture when selling investment real estate and reinvesting into qualifying property. Deferred does not mean eliminated. The only way depreciation recapture may be removed permanently is through estate planning and the step up in cost basis when the property passes to heirs. Understanding the difference between tax deferral and tax elimination is an important part of long term real estate planning. #DST #1031Exchange #RealEstateInvesting Disclosure: DST investments are speculative, illiquid and can expose investors to risks including the potential loss of the entire investment principal, potential property value loss, foreclosure and loss of management control. Past performance is not a guarantee of future results. Securities offered through 1031 Securities Inc., member FINRA / SIPC. 1031 Securities Inc. and 1031 Financial are unaffiliated. See “About” or “Intro” for further details.

🏗️ Creative Tax Deferral: Mastering the Dual-Note Exit Strategy When selling a high-value asset, the tax bill can be the biggest hurdle to compounding your wealth. Mitch McGinley and Brett Swartz discuss a sophisticated solution that combines traditional installment sales with a Deferred Sales Trust. By structuring the exit with two distinct notes—one for immediate stabilization and a second for long-term deferral—sellers gain unmatched flexibility. This strategy allows you to bridge the gap during a "cash-out refi" phase while keeping your capital working for you rather than the IRS. Key Takeaways: How to use dual-notes to maximize flexibility during a business exit. The benefits of combining a trust strategy with traditional seller carry-back. Coordinating a cash-out refinance to satisfy notes without triggering immediate tax. #TaxStrategy #ExitPlanning #BuildItToBillion #MitchMcGinley #WealthManagement #CapitalGains #BusinessBrokerage #DualNote

Tax season and rollover shouldn’t feel like an all-hands fire drill. 📃 With the right platform, Q1 can run on automated processes rather than manual work. A calmer, more predictable busy season is ahead. See Elevate in action: https://bit.ly/4tcCBgy

There is absolutely no need to have service volumes spike after the new year. If you administer #HSA,#FSA or #HRA plans and struggle with these issues, give us a call. These are the things that kill margins and client satisfaction, one bad month can ruin an entire relationship.