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Lara Woods

What tax shelters can high earners actually use besides the standard options?

So I recently got a substantial promotion and now I'm making way more than I used to - around $225k annually. I've already maxed out my 401k, set up 529 plans for my kids, and contribute the max to my HSA, but I keep hearing about "high earner tax shelters" from colleagues. What other legitimate options do high earners have to reduce tax liability? Are there specific investment vehicles or strategies that make sense at this income level? I feel like I'm missing out on something beyond the usual stuff everyone talks about. My CPA hasn't been super helpful - just keeps saying "max your retirement accounts" which I'm already doing. There's gotta be more to it when your income jumps into a higher bracket, right? Would appreciate any insights from folks who've been in similar situations.

Adrian Hughes

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The main strategies beyond the basics you've already covered (401k, HSA, 529) would include: 1) Backdoor Roth IRA - Since you're over the income limit for direct Roth contributions, you can make a non-deductible traditional IRA contribution and then convert it to a Roth. There's no income limit on conversions. 2) Mega Backdoor Roth - If your employer plan allows after-tax contributions (not just Roth), you may be able to contribute up to the total 401k limit ($69,000 for 2025) minus your standard contributions and employer match. 3) Cash value life insurance - Specifically properly structured policies can provide tax-advantaged growth and tax-free access to funds. 4) Qualified Opportunity Zones - These allow you to defer capital gains tax by investing in designated economically distressed communities. 5) Real estate investments - The depreciation deduction can offset income, and strategies like 1031 exchanges can defer capital gains tax.

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Lara Woods

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Thanks for these suggestions! I've heard of backdoor Roth but wasn't sure if it was worth the hassle. Do you know if there are income limits on the mega backdoor Roth option? And regarding cash value life insurance - isn't that usually considered a poor investment compared to just investing directly in the market?

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Adrian Hughes

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There are no income limits on the mega backdoor Roth, which is what makes it attractive for high earners. The only limitation is that your specific employer plan must allow both after-tax contributions (beyond the regular 401k limit) and in-plan Roth conversions or in-service distributions. Cash value life insurance gets a bad reputation often because many policies are poorly structured with high fees. However, a properly designed policy (typically a whole life policy from a mutual company or an indexed universal life policy with the right parameters) can be quite effective as a tax strategy rather than as your primary investment. It's all about how it's structured and ensuring it's not commission-heavy.

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After struggling with similar tax questions when my income jumped last year, I tried this AI tax advisor at https://taxr.ai and it was actually super helpful for my situation. I uploaded my previous returns and answered some questions about my new income, and it gave me a personalized tax strategy report that identified some options my accountant hadn't mentioned. For my situation, it suggested a combination of a defined benefit plan (since I have some self-employment income on the side) and some specific charitable giving strategies using appreciated securities. It also flagged that I was approaching the NIIT threshold and suggested some strategies to manage that. Basically gave me a roadmap I could take to a better CPA.

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Ian Armstrong

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Did it actually give specific advice or just general concepts? I've tried other "AI tax tools" before and they just spat out generic info I could find on Google.

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Eli Butler

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How does it work with more complex situations? I have W-2 income plus a side business LLC that's taxed as an S-corp, plus some rental properties. Would it handle all that or get confused?

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It gave surprisingly specific advice based on my situation - not just generic concepts. For example, it calculated exactly how much I could contribute to a defined benefit plan based on my self-employment income and age, and showed the tax impact over 5 years. For complex situations like yours with multiple income sources, it actually seems designed for that. The questionnaire was pretty detailed and had specific sections for business income, pass-through entities, and rental properties. It asked about my S-corp's profit distribution strategy and whether I was taking an appropriate salary. Then it modeled different scenarios showing tax implications of various approaches.

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Ian Armstrong

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I was initially skeptical about taxr.ai since most "tax tools" I've used have been garbage, but I decided to try it after seeing this thread. It actually identified some significant opportunities I was missing. The biggest one for me was that I could establish a Solo 401k for my consulting side gig (even though I have a day job with a 401k already), which opens up another $69k in potential tax-advantaged space. My previous CPA never mentioned this! It also recommended a specific strategy for bunching charitable deductions in alternating years to get over the standard deduction threshold, with detailed calculations showing the actual tax benefit. Now I'm looking for a new accountant who can help implement these strategies for 2025.

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If you're dealing with IRS issues around any of these high-income strategies, getting actual IRS clarification is crucial but nearly impossible with their phone lines. I spent WEEKS trying to get through about a similar situation last year. Finally used https://claimyr.com after seeing it mentioned here, and they got me connected to an IRS agent in about 15 minutes. You can see how it works at https://youtu.be/_kiP6q8DX5c - it's basically a service that navigates the IRS phone tree and waits on hold for you, then calls you when they have an agent on the line. Ended up getting clarification on how the IRS treats specific depreciation scenarios for my real estate investments and confirmation about a mega backdoor Roth strategy I was considering. Saved me thousands in potential penalties from doing something incorrectly.

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Lydia Bailey

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Wait, how does this actually work? Do they have some special access to the IRS or something? Seems sketchy that they can get through when regular people can't.

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Mateo Warren

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Yeah right, nobody gets through to the IRS. I've been trying for months about an audit issue. This sounds like snake oil - you probably work for them.

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They don't have special access to the IRS - they just use technology to automate the calling and waiting process. It's like having a robot assistant that keeps calling back when disconnected and navigates through all the prompts for you. When they finally get a human, they connect you with that person. I was skeptical at first too. I tried calling the IRS seven times myself and got disconnected each time after waiting 45+ minutes. I was desperate and figured it was worth trying since my tax situation with the real estate depreciation was potentially a five-figure difference. It's designed for exactly these situations where you need official clarification on more complex tax strategies.

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Mateo Warren

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Alright, I need to publicly eat my words here. After my skeptical comment yesterday, I tried Claimyr this morning for my audit issue. Not only did it work, but I got connected to someone in the IRS audit department who actually resolved my case on the spot. Turns out my documentation HAD been received but wasn't properly processed in their system. I'd been stressing about this for months and having it resolved in one 20-minute call is honestly life-changing. I would've continued to get penalty notices and potentially had my accounts levied. For anyone dealing with complex tax situations that require IRS clarification - especially around high-earner strategies that might trigger audit flags - being able to actually talk to someone makes a huge difference.

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Sofia Price

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Don't overlook investing in oil and gas partnerships - they come with significant tax advantages for high earners through depletion allowances and intangible drilling costs (IDCs). In some cases, you can deduct up to 80-90% of your investment in the first year, which can significantly offset other income. Obviously there are risks involved, but if you're in a high tax bracket and have some appetite for alternative investments, it's worth considering as part of your portfolio. Make sure you work with a reputable company though, as there are plenty of sketchy operators in this space.

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Alice Coleman

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Are these still worthwhile with the changing climate policy landscape? I've heard these investments could become stranded assets if we transition away from fossil fuels too quickly.

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Sofia Price

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That's definitely a valid concern and something to factor into your risk assessment. The current tax advantages remain substantial regardless of future policy changes, but the long-term value of the underlying assets could certainly be affected by climate policy. Some partnerships are hedging by diversifying into renewable energy projects that also offer tax advantages through credits, though these typically don't provide the same immediate deduction benefits as traditional oil and gas. It really depends on your time horizon and risk tolerance - these work best as a smaller portion of a diversified strategy rather than your primary tax shelter.

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Owen Jenkins

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For truly high earners ($500k+), consider a Private Placement Life Insurance (PPLI) policy. It's basically a tax shelter wrapped in life insurance that allows you to invest in alternative assets like hedge funds and private equity with tax-free growth and tax-free access through policy loans. Minimum investments usually start at $1M though.

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Lilah Brooks

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I've read about these but always assumed they were for ultra-wealthy ($10M+). Any resources on how to find legitimate providers that work with merely "wealthy" vs "ultra-wealthy" clients?

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These sound too good to be true. If they're so great, why doesn't everyone use them? Is there a catch the sales materials don't mention?

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At your income level, you should also look into defined contribution plans beyond just the basic 401k. If you have any self-employment income (consulting, side business, etc.), you could set up a SEP-IRA or Solo 401k for that income stream, which opens up additional contribution limits. Another strategy worth exploring is tax-loss harvesting in your taxable investment accounts - systematically realizing losses to offset gains and up to $3k of ordinary income annually, while using the wash sale rule strategically. For charitable giving, consider donating appreciated securities directly instead of cash - you avoid capital gains tax on the appreciation while still getting the full deduction. If you're not already itemizing, bunching multiple years of charitable contributions into alternating years can help you exceed the standard deduction threshold. Also look into qualified small business stock (QSBS) investments if you're comfortable with startup risk - under Section 1202, you can exclude up to $10M or 10x your basis in gains when you sell qualifying small business stock held for 5+ years. The key is finding a tax professional who specializes in high-earner strategies rather than just basic tax prep. Many CPAs aren't familiar with these more advanced techniques.

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Miguel Harvey

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This is exactly the kind of comprehensive advice I was hoping to find! I do have some consulting income on the side (maybe $15k annually), so the Solo 401k option could be huge for me. Quick question - can I contribute to both my employer's 401k AND a Solo 401k for the consulting income, or do the contribution limits interact somehow? Also, you mentioned finding a tax professional who specializes in high-earner strategies - any tips on how to identify those vs the standard tax prep folks?

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Yes, you can absolutely contribute to both! The limits are separate as long as the Solo 401k is for genuine self-employment income. For 2025, you could max out your employer 401k ($23,500) AND contribute up to 25% of your net self-employment earnings to the Solo 401k (with a combined employee/employer contribution limit of $69,000 total across both plans). With $15k consulting income, you could potentially contribute around $2,800-3,000 to the Solo 401k depending on your net profit after self-employment taxes. Not huge, but every bit helps when you're in a high bracket. For finding the right tax professional, look for CPAs or EAs who advertise "high net worth tax planning" or "advanced tax strategies." Ask specifically about their experience with strategies like mega backdoor Roth, QSBS, and alternative investments. Many charge higher fees but it's worth it - a good one should save you way more than they cost. You can also check if they have additional certifications like PFS (Personal Financial Specialist) which indicates more sophisticated planning knowledge.

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Another strategy worth considering at your income level is a Deferred Compensation plan if your employer offers one. These plans let you defer a portion of your current salary (and the associated tax liability) to future years when you might be in a lower bracket. The downside is you're essentially lending money to your employer unsecured, so there's credit risk if the company goes under. Also look into Conservation Easements if you're interested in land conservation and have significant tax liability to offset. You can donate development rights on property (land you own or purchase specifically for this purpose) and potentially get a charitable deduction worth several times your investment. However, the IRS has been scrutinizing these heavily lately, so make sure any program you consider is well-established and conservative in its valuation approach. For your existing investments, consider tax-efficient fund placement - holding tax-inefficient investments in your tax-advantaged accounts (401k, IRA) and tax-efficient index funds in taxable accounts. This can meaningfully reduce your annual tax drag on investment growth.

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ThunderBolt7

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The deferred compensation point is really interesting - I hadn't considered that option before. Do most large employers offer these plans, or is it typically just executive-level compensation? Also, regarding conservation easements, I've heard horror stories about people getting audited over aggressive valuations. Are there any red flags to watch out for when evaluating these programs, or specific questions to ask to ensure they're legitimate?

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Ethan Moore

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Deferred compensation plans are typically offered by larger companies (Fortune 500 type) and are often restricted to higher-level employees or those above certain income thresholds - usually $130k+ annually. They're not as common as 401k plans but worth asking HR about if you work for a sizable company. For conservation easements, the red flags include: programs promising deductions of 4x+ your investment (the IRS considers these "too good to be true"), newly formed partnerships without track records, and any program that guarantees specific tax outcomes. Ask for independent appraisals from MAI-certified appraisers, references from previous participants who've been through IRS audits successfully, and make sure the conservation organization has been operating for at least 5+ years. The legitimate ones typically offer more modest deductions (1.5-2.5x investment) and can provide detailed audit defense support. Honestly, given the current IRS scrutiny, I'd be very cautious with conservation easements unless you have significant tax liability ($50k+ annually) and can afford to defend an audit. The juice might not be worth the squeeze at your current income level.

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Consider looking into Captive Insurance Companies (CICs) if you own a business or have significant business income. Under Section 831(b), you can elect to have your captive taxed only on investment income, not insurance premiums, for captives with less than $2.3M in annual premiums. This allows you to deduct legitimate business insurance premiums paid to your own captive, while the captive accumulates wealth in a tax-advantaged structure. Another often-overlooked strategy is investing in Qualified Opportunity Zone funds, which allow you to defer capital gains taxes by investing those gains into designated economically distressed communities. You get a 10% step-up in basis after 5 years, 15% after 7 years, and if held for 10+ years, any appreciation in the QOZ investment itself is tax-free. For immediate tax relief, look into Cost Segregation studies if you own any commercial real estate or rental properties. This allows you to accelerate depreciation on certain components of buildings (like flooring, lighting, landscaping) from 27.5-39 years down to 5-15 years, creating significant upfront deductions. Finally, consider establishing a Charitable Remainder Trust (CRT) if you have highly appreciated assets. You get an immediate charitable deduction, avoid capital gains tax on the sale of the appreciated assets within the trust, and can receive income payments for life while ultimately benefiting charity.

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Aria Park

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This is incredibly comprehensive - thank you! The Captive Insurance Company strategy is completely new to me. Is there a minimum business income threshold where CICs start to make sense, or specific types of businesses where they work best? I'm curious about the operational complexity too - do you essentially have to run a legitimate insurance operation, or can it be more passive? The Opportunity Zone concept sounds interesting but I'm wondering about liquidity concerns with the 10-year hold requirement. Have you seen good quality investment opportunities in these zones, or are most of them pretty speculative real estate plays? Also, regarding Cost Segregation studies - roughly what's the minimum property value where the study costs justify the tax benefits? I have one rental property worth about $300k but wasn't sure if it would be worth the expense of hiring specialists for the analysis.

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