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Have you looked into treating this as a return of capital under Section 301(c)(2) rather than a dividend? If the C-Corp has sufficient E&P to cover the distribution, that's problematic, but if not, you might be able to treat at least part of it as a return of capital up to the shareholder's basis. Also, consider whether the franchise sale could qualify as a sale of a separate business segment under Section 302(e)(2), which would support partial liquidation treatment even without explicit documentation.
We've considered the return of capital approach, but unfortunately the company has substantial E&P that would cover the distribution amount. I like your suggestion about Section 302(e)(2) though. The franchise locations operated as separate business segments with their own management and financial statements. Do you think we could argue this meets the "not essentially equivalent to a dividend" test under 302(b)(1) given the meaningful contraction of the business operations? The corporation went from two operating locations to one, which seems substantial.
The separate business segment approach under 302(e)(2) would be your strongest argument. Since you had two distinct franchise locations and one was completely sold off, this represents a genuine contraction of the business rather than just a distribution of earnings. For the "not essentially equivalent to a dividend" test under 302(b)(1), you're in a tougher position since this is a sole shareholder situation. The test typically looks at whether there was a meaningful reduction in the shareholder's proportionate interest in the corporation, which doesn't happen with a 100% shareholder. However, courts have occasionally looked at other factors in sole shareholder cases, including business purpose and whether there was a genuine contraction. I'd recommend documenting the business reasons for the sale (separate from tax considerations) and showing how the operations contracted. Even without formal documentation at the time, you might be able to establish partial liquidation treatment based on the actual substance of what occurred.
This is a complex situation that requires careful analysis of multiple code sections. Given that the C-Corp already paid tax on the gain but the shareholder received the proceeds directly, you're essentially dealing with a constructive dividend unless you can successfully argue for different treatment. Your best path forward is likely the partial liquidation argument under Section 302(b)(4) combined with 302(e)(2). The key factors working in your favor are: 1) genuine contraction of business operations (50% reduction from two locations to one), 2) complete termination of one business segment, and 3) the distribution was directly attributable to the business contraction. The lack of formal documentation is problematic but not necessarily fatal. Rev. Rul. 75-223 and several Tax Court cases have recognized partial liquidations based on substance over form when there's clear evidence of business contraction. Document everything you can about the business reasons for the sale and consider preparing a detailed memorandum establishing the facts and legal basis for partial liquidation treatment. One additional consideration: make sure to calculate whether the shareholder has sufficient basis to absorb the distribution. If the basis exceeds the distribution amount, the entire amount could be treated as a return of capital under a successful partial liquidation argument. You might also want to consider filing a protective election or amended return with alternative treatments to preserve your options if the IRS challenges the characterization.
I had this EXACT same issue with E*TRADE last year. Different plan numbers for traditional and Roth Solo 401k components. When I filed my taxes, it got flagged for review because it looked like I had two separate plans with different contribution limits. Took 3 months to sort out with the IRS. Had to provide all the plan docs showing it was actually supposed to be one plan. Get this fixed ASAP before tax time comes around - you don't want the headache I dealt with.
Thanks for sharing this! Did you end up getting any penalties from the IRS for having the wrong plan setup? Or was it just a lot of paperwork to fix it?
This is a really important issue that more solo business owners need to be aware of. I went through something similar with my Solo 401k setup at Schwab. The key thing to understand is that the IRS treats a Solo 401k as a single plan regardless of whether you have traditional and Roth components. What you've described - having different plan numbers and names - essentially creates the appearance of two separate plans in the eyes of the IRS. This can cause several problems: 1. Contribution limit confusion - you might accidentally exceed the annual limits if the system treats them as separate plans 2. Required Minimum Distribution (RMD) calculations get complicated when you reach that age 3. Form 5500 filing requirements become unclear if your assets grow The good news is this is fixable. Call E*TRADE's retirement plan department (not regular customer service) and explain that you need to consolidate your Solo 401k traditional and Roth components under a single plan number and name. They should be able to process a plan amendment to correct this. Don't wait on this - it's much easier to fix now than after you've made contributions and have multiple years of statements with inconsistent plan information.
FYI - NJ announced they're taking longer this year due to increased fraud prevention measures. Their official statement says most refunds will take 4-6 weeks minimum, even for simple returns with no issues. They're manually reviewing more returns than in previous years.
Just wanted to add that I'm seeing the same thing with my NJ return filed around the same time as yours. The "no information available" status is really frustrating when you're waiting for your refund. I've been checking daily but trying to be patient since everyone here is saying 4-6 weeks is normal now. At least it's good to know we're not alone in this - seems like NJ is just really backed up this year with all the fraud prevention measures they mentioned.
Just wanted to add another option - I've been using that free open source tool called "Beancount" to handle my investment tracking. It takes a bit of setup initially, but there's a plugin that can directly import from Robinhood and then export in formats compatible with most tax software, including TaxAct.
I've been dealing with this exact same headache! What finally worked for me was a combination approach. First, I contacted Robinhood support through their app (like StarSailor mentioned) and requested an alternative format - they sent me a CSV file that had most of my transaction data in a cleaner format. However, I still had to manually reconcile the wash sale adjustments from the official 1099-B PDF. What I did was create a simple spreadsheet where I imported the Robinhood CSV, then added columns for the wash sale adjustments by cross-referencing the PDF. It's not perfect, but it cut my manual entry time from 6+ hours down to about 90 minutes. For anyone going this route, make sure to double-check that your total gains/losses in your final import file match what's on your official 1099-B before submitting to TaxAct. The IRS cares about the official document numbers, so any discrepancies could cause issues later.
Zara Mirza
One thing I learned the hard way - if you donate a fully depreciated business vehicle to charity, you generally can't claim a deduction based on the fair market value. Since your basis is $0, your deduction is typically $0 as well, unless the charity plans to use the vehicle directly for its charitable purpose. IRS rules for vehicle donations got much stricter after 2004. So while donation might sound nice, it might not give you any tax benefit. Selling or trading in for a new business vehicle is usually more advantageous tax-wise.
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Ava Thompson
I went through this exact situation with my electrician business truck last year. After getting fully depreciated to $0, I was dreading the tax hit from selling it. What ended up working best for me was keeping detailed records of all repairs and maintenance costs in the final years - my accountant was able to use these as additional business deductions to help offset some of the recapture income. Also, timing matters a lot. If you're expecting a lower income year coming up, that might be the perfect time to sell since the recapture will be taxed at your ordinary income rate. In my case, I waited until a slower business year and the effective tax rate on the recapture was lower than it would have been during my peak earning years. One more tip - if you're planning to buy another business vehicle anyway, definitely look into the 1031 exchange option others mentioned. The paperwork is a bit more complex but the tax deferral can be significant.
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Raj Gupta
โขThis is really helpful advice about timing the sale during a lower income year! I hadn't thought about how the ordinary income tax rate would affect the recapture differently depending on my overall annual income. Quick question - when you mention keeping detailed records of repairs and maintenance, were you able to deduct those in the same year as the sale to offset the recapture income? Or did you have to spread those deductions over previous years? My truck has needed quite a few repairs lately and I'm wondering if I should be more strategic about when I actually sell it.
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