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Another common mistake I see with ESPP calculations is forgetting about commission fees. When calculating your total gain/loss, don't forget to factor in any fees you paid when selling the shares. For example, if you sold at $250 but paid a $5 commission, your actual proceeds would be $245. This affects both your ordinary income calculation (since it's based partly on actual proceeds) and your capital gain calculation.
This is partly correct but needs clarification. Commission fees paid when SELLING shares reduce your sales proceeds (as you mentioned), but commission fees paid when BUYING the shares increase your cost basis. Many ESPP programs don't charge commissions for purchase, but if yours does, don't forget to add that to your basis.
Great discussion here! I wanted to add a few points that might help others dealing with ESPP calculations: 1. **Record keeping is crucial** - Create a detailed spreadsheet for each purchase lot that includes offering date, purchase date, FMV on both dates, purchase price, sale date, sale price, and all fees. This will save you hours during tax season. 2. **Watch out for same-day sales** - If you sell ESPP shares on the same day you purchase them, the tax treatment can be different. The entire discount may be treated as ordinary income rather than going through the qualifying/disqualifying disposition analysis. 3. **State tax considerations** - Don't forget that your state may have different rules for ESPP taxation. Some states don't recognize the federal preferential treatment for qualifying dispositions. 4. **Multiple brokers** - If your company switched brokers during the year, make sure you're getting all the necessary 1099-B forms. I've seen people miss reporting sales because they forgot about shares held at a previous broker. The original calculation looks mostly correct once you use the purchase date FMV for the discount calculation as Jean Claude pointed out. Just double-check that you're accounting for all fees and that your company isn't already reporting any of this on your W-2.
This is incredibly helpful, especially the point about same-day sales! I didn't realize that could change the tax treatment completely. Quick question about record keeping - do you recommend using any specific software or template for tracking all these details? I've been using a basic Excel spreadsheet but I'm wondering if there's a better way to organize everything, especially when you have multiple purchase lots throughout the year. Also, regarding state taxes - is there an easy way to find out if your state follows federal ESPP rules or has its own requirements? I'm in California and want to make sure I'm not missing anything on the state return.
Called IRS yesterday about this exact thing. They said 4-6 weeks is standard wait time for paper check after DD rejection. But tbh could be faster depending on your location
called right at 7am EST. Only way to get through these days ngl
Same thing happened to me last year. Took about 3 weeks after the rejection for the paper check to arrive. The annoying part is WMR doesn't update very clearly when they switch to paper check - it just keeps saying "being processed" until it's actually mailed. Hang in there, it should come soon since you're already at the 2 week mark!
thanks for sharing your experience! that's reassuring to hear. yeah WMR is pretty useless when it comes to the switch to paper check - wish they'd be more transparent about the process
A warning from someone who learned the hard way - if you're selling on multiple platforms, they ALL count toward that $600 threshold! I was selling on eBay, Mercari, and Facebook Marketplace thinking each platform had its own separate $600 limit. Nope! You have to combine all your sales across all platforms. Also, some payment processors like PayPal or Venmo might send separate 1099-Ks too. I ended up with THREE different 1099 forms for what I thought was a small selling hobby. The IRS computer systems match these forms to your tax ID, so don't forget to report all of them!
I totally get the frustration @Rebecca! I was in the same boat last year - just wanted to declutter and make a few bucks, then suddenly I'm drowning in tax forms. Here's what I wish someone had told me from the start: keep it simple but organized. Create one spreadsheet with columns for: item sold, what you paid for it originally, sale price, shipping costs, and platform fees. That's literally all you need. The good news is you're only taxed on actual profit, not gross sales. So if you bought something for $20, sold it for $35, and paid $3 in fees, you only owe taxes on $12 profit. All those scary 1099 forms just show gross sales - they don't tell the full story of what you actually made. Don't let the complexity scare you away from selling! Just start tracking everything now and you'll be fine next tax season.
Has anyone here actually completed a reorganization from a single C-corp to an opco/holdco structure while maintaining QSBS eligibility? What software or services did you use to track the reorganization?
We did this last year. Used a combination of Carta for equity management (though it was a bit clunky for the reorganization) and worked directly with a law firm that specializes in tech company restructuring. The QSBS eligibility was the trickiest part. We had to be careful about asset transfers and timing. The key was doing a straight stock exchange under 368(a)(1)(B) which allowed for tacking of the holding period. Our legal fees were about $25k all-in, but worth it given the potential tax savings down the road. Make sure both entities meet the active business requirements, and watch out for the assets test - no more than 10% of assets can be portfolio stocks, real estate, etc. We had to adjust some investments to stay compliant.
This is a great question and one I've been exploring for my own business. From my research, the opco/holdco structure is definitely used in the US, though as others mentioned, it's often called "parent-subsidiary" or "multi-entity" structure here. One thing I'd add that hasn't been mentioned yet - consider the timing carefully if you have any plans for future fundraising. Some VCs prefer cleaner cap tables and might view the holdco structure as adding unnecessary complexity during due diligence. However, if you're planning to bootstrap or are past the fundraising stage, the asset protection benefits can be significant. Also, don't forget about potential franchise tax implications in your state of incorporation. Delaware, for example, charges franchise taxes for each entity, so you'll want to factor those ongoing costs into your analysis. The QSBS preservation is definitely the most critical piece - losing that eligibility could cost you millions in tax savings if you have a successful exit. I'd strongly recommend getting multiple opinions from tax professionals who specifically understand Section 1202 before proceeding.
Anastasia Popov
Just got those same codes last week! lets hope we both get paid soon
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Malik Thompson
ā¢fingers crossed! š¤ keep me updated
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Anastasia Popov
ā¢will do! we're all in this together lol
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Eve Freeman
TC 571 is actually a good sign! It means the IRS is releasing a previous hold or reversing an adjustment. Combined with TC 971, you should be getting a notice explaining what happened. I had the same codes last year and got my refund about 3 weeks later. The waiting is brutal but you're probably in the home stretch now. Check your transcript weekly for TC 846 - that's when you'll see your actual refund date!
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Vincent Bimbach
ā¢Thanks for explaining this! Really helps to hear from someone who's been through it. I'll definitely keep checking for that 846 code. Just hoping the IRS moves faster than usual š¤
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