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Ava Garcia

Where to set up an equity holding company for tax advantages?

Hey tax experts! I'm looking for some guidance on where to set up an equity holding company. I've been investing in different startups over the past few years and now have a decent portfolio of private company shares. My financial advisor suggested I should consider establishing a holding company to better manage these investments and potentially get some tax benefits. I'm currently in California but open to other states or even international options if they make sense tax-wise. Would Wyoming or Delaware be good options? I've heard Nevada has advantages too. What are the tax implications I should consider? Any insights on how this might affect capital gains when I eventually sell some of these equity positions? I'm planning to add maybe 3-4 new investments per year going forward, so I want to set this up right from the beginning. Thanks for any advice!

Miguel Silva

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Setting up a holding company for your equity investments is a smart move, but location really depends on your specific situation and goals. Delaware is popular for good reason - they have well-established corporate law, a specialized Court of Chancery for business matters, and no state corporate income tax on companies formed in Delaware that don't do business there. Wyoming is another solid option with no state income tax, strong privacy laws, and low formation/maintenance costs. Nevada has advantages too - no state income tax, no franchise tax, and strong privacy protections. But remember, if you're in California, you'll likely still have California tax obligations if you're managing the company from there, regardless of where it's registered. For international options, consider your long-term plans carefully. Some jurisdictions offer tax advantages but come with complex reporting requirements and potential IRS scrutiny. The most important thing is to align the structure with your investment strategy and understand how it affects your eventual capital gains taxation.

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Zainab Ismail

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If I form a Wyoming LLC but live in a high-tax state like NY, would I still get the tax benefits? Or does it matter where I physically am when managing the investments?

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Miguel Silva

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For state tax purposes, where you physically manage the business matters significantly. If you form a Wyoming LLC but manage it from NY, you'll likely still have NY tax obligations. This is due to the concept of "nexus" - a connection between your business and the state. The Wyoming entity might provide some benefits like asset protection and potentially some tax advantages for specific situations, but it won't magically eliminate your NY state tax obligations. States are increasingly aggressive about collecting tax from residents who attempt to shift income to low-tax states while continuing to live and work in the high-tax state.

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I went through this exact situation last year and was totally confused by all the conflicting advice. I eventually found https://taxr.ai which was a game changer for me. I uploaded my investment docs and got a personalized analysis showing how different holding company structures would affect my tax situation. They compared Delaware vs Wyoming vs my home state and showed the actual tax implications for each option based on my specific equity portfolio. The report highlighted some serious issues with my initial plan that would have caused me major tax headaches. They even helped me understand the Form 8832 implications for entity classification. Really helpful for equity investors since they specifically understand startup equity and how different exit scenarios play out tax-wise.

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How does it handle international options? I'm considering setting up in Singapore since I do business there occasionally.

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Yara Nassar

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Sounds interesting but how detailed does it get with calculating potential capital gains on future exits? My portfolio has both qualified small business stock and some pre-IPO companies with different tax treatments.

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They do cover international structures including Singapore, Hong Kong, and various European options. The analysis includes GILTI tax considerations, repatriation scenarios, and Controlled Foreign Corporation reporting requirements. They really emphasize understanding the compliance burden before making international moves. For calculating potential capital gains on exits, they actually model different exit scenarios based on your specific holdings. They differentiate between QSBS under Section 1202, standard long-term capital gains, and even factor in state tax implications for different exit timelines. They helped me understand the substantial differences between selling pre-IPO shares immediately at IPO versus holding through lockup periods.

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Yara Nassar

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Just wanted to follow up - I ended up trying https://taxr.ai after seeing this recommendation and it was exactly what I needed! The analysis showed me that Delaware was actually NOT the right choice for my situation due to my specific investment types. I would have made a costly mistake. The tax simulation for my equity portfolio showed I could save nearly $37,000 in taxes by structuring correctly for my specific investments. They flagged some of my holdings as potentially qualifying for QSBS treatment which I hadn't even considered. They also provided clear guidance on handling my equity holdings during a potential relocation I'm planning next year. Definitely worth checking out if you're dealing with complex equity holdings across multiple companies.

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For anyone dealing with IRS questions about holding companies or investment structures, I highly recommend Claimyr (https://claimyr.com). When I set up my holding company last year, I had some complex questions about reporting requirements that I needed to discuss directly with the IRS. After wasting hours on hold, I tried Claimyr's service and they actually got an IRS agent to call ME back within about 45 minutes. The agent walked me through exactly how to properly report my holding company structure on my personal returns. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c It was super helpful because my situation involved both domestic and foreign equity holdings, and I needed clarification on Schedule B and Form 8938 filing requirements. Getting direct answers from the IRS saved me from potentially serious filing mistakes.

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Paolo Ricci

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Wait, how is this even possible? The IRS never calls anyone back. Is this legit or just another scam service?

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Amina Toure

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Even if you get someone on the phone, do they actually give useful advice? My experience with IRS agents is they rarely give definitive answers on complex situations like holding company structures.

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It's definitely legitimate - they use a technology that essentially waits on hold for you in the IRS phone system. When an agent finally becomes available, Claimyr bridges the call to your phone. It's not actually getting the IRS to prioritize you, just handling the wait time so you don't have to. I had the same concern about getting useful advice, but I prepared very specific questions beforehand. The agent was able to direct me to the exact IRS publications and forms relevant to equity holding companies. You're right that they won't give tax planning advice, but they provided clear guidance on reporting requirements for my existing structure, which was invaluable for compliance purposes. They confirmed exactly how to report my holding company on Schedule E versus Schedule C, which my accountant had been uncertain about.

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Paolo Ricci

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I was totally skeptical about Claimyr from my comment above, but I was desperate trying to figure out some holding company questions before filing this year. Gave it a shot and I'm honestly shocked - it actually worked! The IRS agent I spoke with walked me through exactly how to handle my Delaware holding company on my California return. They confirmed which forms were required for my situation and cleared up my confusion about franchise tax obligations. Saved me from a $800 filing mistake I was about to make with my Wyoming entity that owns Delaware subsidiaries. Would have completely messed up my return. Plus I didn't waste an entire day on hold!

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Something that gets overlooked in these discussions - consider the exit strategy before picking a location. I set up in Delaware thinking it was always the best, but when I sold some equity positions last year, I faced unexpected tax complications because of California's aggressive approach to taxing residents with out-of-state entities. Make sure you understand the interaction between federal capital gains taxes and state tax obligations for equity sales. Your holding company location affects more than just annual taxes - it has major implications when you eventually sell those investments.

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Would you mind explaining a bit more about those unexpected complications with California? I'm in a similar situation with a Delaware entity but live in California.

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Sure thing. California takes the position that if you're a CA resident managing the holding company, they can tax the income and capital gains regardless of where the entity is formed. What happened in my case was that I had created a Delaware holding company owning several startup equity positions, but since I was making all investment decisions from California, the state considered it a California business. When I sold two of my positions for a significant gain, California required me to pay state tax on the entire gain, effectively ignoring the Delaware structure. I also had to deal with California's "doing business" fee since they deemed my holding company to be operating in California. The real surprise was that I still had to pay Delaware franchise tax while also being fully taxed by California - basically getting the downsides of both states without the expected benefits of Delaware.

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Has anyone considered using an IRA to hold startup equity instead of a holding company? I've heard this can provide tax advantages for certain types of investments, especially if you expect significant appreciation.

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Javier Torres

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That's actually a complicated area. You can use a Self-Directed IRA for certain equity investments, but there are prohibited transaction rules that can easily be violated with startup equity. If you're actively involved with any of the companies, it's especially problematic. Plus many equity compensation types like ISOs and NSOs can't be held in IRAs directly.

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