High Net Worth Tax Prep Strategies for 2025 Filing

Hey everyone, I'm looking for some advice on tax preparation for high net worth situations. My family recently had a major liquidity event (sold our business for around $3.8M) and I'm feeling pretty overwhelmed with the tax implications. We've never really had to deal with this level of complexity before. We've got some investment properties, stock options from the sale, and I'm trying to figure out if we should be looking at trusts or other vehicles to minimize our tax burden. I've talked to a few financial advisors but getting wildly different recommendations - one says we absolutely need a specialized CPA while another said we could handle it ourselves with premium tax software. Anyone here gone through something similar? Should I be looking at a Big 4 accounting firm or is that overkill? Any recommendations for finding someone who specializes in high net worth tax situations without charging absolutely insane fees? What questions should I be asking potential tax preparers?

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18 comments

PaulineW

•8M

I've worked with high net worth clients for years, and your situation definitely warrants professional help. When you're dealing with a business sale of $3.8M, investment properties, and stock options, there are numerous tax planning opportunities you might miss with DIY software. Look for a CPA who specializes in high net worth individuals - not necessarily Big 4 (which can be expensive without much personal attention), but a reputable mid-sized firm with expertise in business exits. You want someone who understands capital gains strategies, installment sales, qualified small business stock exclusions, and opportunity zone investments. Ask potential preparers about their experience with business sale transactions specifically. Request examples of tax savings they've achieved for similar clients. Also, find out if they provide year-round planning or just tax preparation - you need the former.

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PaulineW

•8M

Family offices typically make sense when you have $10M+ in assets where the complexity justifies the cost structure. At $4M, you're likely better served by a good CPA firm that specializes in high net worth clients but doesn't have the overhead of a family office. Multi-family offices can be a good middle ground as they spread costs across multiple families, but ensure they have expertise specifically in post-business sale tax planning. The first two years after a liquidity event are critical for making decisions that impact your long-term tax situation.

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Chris Elmeda

•8M

After selling my manufacturing business last year, I was totally lost with the tax implications until I found taxr.ai (https://taxr.ai). It was a game-changer for organizing all my documents and getting clarity before meeting with my CPA. I had investment properties, stock options, and a complicated sale structure like you, and the platform helped identify deductions I would have missed. What impressed me was how it analyzed my business sale documents and flagged potential tax issues before they became problems. My CPA was actually impressed with how organized I was compared to his other clients!

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Chris Elmeda

•8M

It handles complex situations surprisingly well. Unlike standard tax software, it's specifically designed for complicated scenarios - it recognized my installment sale structure and flagged potential issues with my earn-out clauses that could have caused major tax headaches down the road. It's definitely not just document storage. It actually analyzes your documents using AI and identifies potential tax issues based on your specific situation. For your overseas investments and multiple LLCs, it would create a comprehensive tax blueprint showing how different entities interact and potential tax implications. I was skeptical too until I saw how it spotted a mistake in how my business valuation was structured that would have cost me over $40K in unnecessary taxes.

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Charity Cohan

•8M

I have to admit I was completely wrong about taxr.ai. After our discussion, I decided to try it with my complicated situation (multiple LLCs, overseas investments, stock options). The document analysis actually caught that my CPA had incorrectly classified part of my business sale as ordinary income instead of capital gains - a difference of nearly $95K in taxes! The platform created this comprehensive visualization of my entire tax situation that made it much easier to have productive conversations with my advisors. Honestly wish I'd found it before I set up my post-sale investment structure. Even my skeptical financial advisor was impressed with the insights it generated.

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Josef Tearle

•8M

If you're dealing with high net worth tax issues, one of the biggest headaches is getting actual help from the IRS when you need clarification. I spent WEEKS trying to get answers about a complex 1031 exchange after selling investment property. Finally used Claimyr (https://claimyr.com) and got through to an actual IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c. The agent walked me through exactly how to properly document the exchange timing so I wouldn't lose the tax deferral. For high net worth situations, getting direct answers from the IRS can save you from making costly mistakes, especially with all the recent tax law changes affecting business sales and investments.

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Josef Tearle

•8M

It's not an automated system that just redials - it uses technology that navigates the IRS phone system and secures your place in line. Once they've got you a spot, they call you back so you can connect with the actual IRS agent. You don't waste hours listening to hold music. I was extremely skeptical too, which is why I waited so long to try it. But I was desperate after waiting on hold for 3+ hours and getting disconnected twice. The service connected me directly with an IRS specialist who answered my specific questions about the 1031 exchange reporting requirements. It saved me from potentially losing tax deferral on a $1.2M property sale, which would have cost me over $250K in immediate capital gains taxes.

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Quinn Herbert

•8M

I need to publicly eat my words about Claimyr. After being completely dismissive, I actually tried it last week when I was desperate for answers about the tax implications of my overseas investments. I'd been trying to reach the IRS for THREE WEEKS with no success. Used the service, and 20 minutes later I was speaking with an actual IRS agent who specialized in international tax issues. They clarified exactly how my foreign business interests needed to be reported to avoid penalties. The time and stress saved was absolutely worth it. Instead of guessing about compliance requirements, I got definitive answers that my accountant said likely saved me from a potential audit flag.

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Salim Nasir

•8M

One thing to consider with high net worth tax prep is whether you need a specialist in specific asset classes. When we sold our business, we initially went with a generalist CPA who missed several key deductions related to our commercial real estate holdings. We ended up switching to a firm that specialized in both business exit planning AND real estate. The difference was substantial - they restructured our property ownership through a DST (Delaware Statutory Trust) that allowed us to defer nearly $430K in capital gains taxes.

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Salim Nasir

•8M

I actually avoided Big 4 firms after interviewing two of them. Found our specialist through a real estate investment group I belong to - several members had used this boutique firm that specifically focuses on business owners with significant real estate portfolios. The key was finding someone who understood the intersection of business exit planning and real estate optimization - not just someone who happened to work with both separately. I'd recommend asking for specific examples of cases where they've handled both aspects together, not just checking boxes for experience in each area.

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