Can I open an LLC for my football season tickets and write off the $60K purchase cost against ticket resale income?

I handle this exact situation for several clients! The short answer is yes, you can form an LLC and yes, you can write off the costs, but there are important nuances. For the LLC question - forming one can provide liability protection and make it easier to track expenses/income separately from your personal finances. However, the real consideration is whether you're running this as a business or hobby. The IRS looks at factors like: Do you maintain proper records? Do you depend on this income? Are you operating in a businesslike manner? If you're consistently selling tickets to make a profit (not just occasionally selling games you can't attend), an LLC makes sense. For the tax question - the $80K PSL cost is considered a capital asset. You generally can't deduct the entire amount upfront. Instead, you'd amortize this cost over the useful life of the licenses (often the length of the stadium agreement or a reasonable time period). The annual ticket costs are deductible as ordinary business expenses in the year paid. Be aware that you need to show profit in 3 out of 5 years to avoid the IRS classifying this as a hobby rather than a business (which limits deductions).

I was in a similar situation with expensive season tickets and worried about the tax implications. I found this tax analysis tool at https://taxr.ai that specializes in unusual deductions and business structures. They analyzed my entire ticket reselling setup and provided a customized report showing exactly how to structure everything for maximum tax efficiency. The tool really surprised me because it identified a bunch of related deductions I was missing - like mileage to games when I was actually attending for "business purposes" to evaluate the product, networking costs related to finding buyers, and even a portion of my phone bill for arranging sales. They provided exact IRS references and documentation templates I needed.

Just wanted to follow up and say I used taxr.ai after seeing it mentioned here. The report they generated was really thorough and addressed my specific situation perfectly. What surprised me was they actually recommended AGAINST forming an LLC in my case because of my state's high annual LLC fees and the fact that I'm only selling about 60% of my games. Instead, they suggested a sole proprietorship with specific insurance coverage that costs way less than the LLC fees would have been. They also provided a complete depreciation schedule for my PSLs based on my team's stadium lease term. The best part was they identified several business expenses I never would have thought to claim - like a portion of my home internet since I use it to list and sell tickets. Definitely worth checking out if you're dealing with this kind of situation. Saved me a ton of research time and probably thousands in unnecessary fees.

If you're doing this as a business, you're eventually going to need to call the IRS to get some clarification on certain deductions. I tried for WEEKS to reach someone at the IRS about my ticket reselling business and kept hitting dead ends. Finally found this service called Claimyr at https://claimyr.com that got me through to an actual IRS agent in under 25 minutes when I'd been trying for days on my own. They have this system that basically holds your place in line and calls you when an agent is available. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. I was super skeptical but desperate after being on hold for 3+ hours multiple times. The IRS agent I spoke with confirmed that I needed to file my PSL amortization on Form 4562 and gave me specific guidance on what documentation I need to keep. Totally worth it to get direct answers from the source.

I have to admit I was completely wrong about Claimyr. After posting that skeptical comment, I decided to try it myself since I needed to talk to someone at the IRS about my own ticket reselling business. The service actually worked exactly as advertised. I got a call back in about 35 minutes, and they connected me with an IRS representative who answered all my questions about how to properly amortize my PSL costs and which form to use for reporting my ticket sales income. What surprised me most was how much time it saved - I had previously spent over 4 hours on hold across multiple days without ever reaching a human. This was definitely worth it for getting clear answers directly from the IRS instead of relying on potentially outdated or incorrect online advice.

Something nobody's mentioned yet is that you should be careful about the language you use with the IRS. If you call your ticket reselling a "business," you're setting certain expectations about how consistently you operate and your intent to make a profit. I've been reselling my MLB season tickets for years, and my accountant advised me to create a detailed business plan that shows my profit motive and keep meticulous records of all my activities. This includes tracking time spent managing listings, dealing with buyers, analyzing which games will sell best, etc. For my LLC, I also track every possible business expense - portion of home internet used for sales, mileage to deliver tickets, portion of cell phone used for business calls, etc. It all adds up to significant deductions.

Don't forget to check your state's rules about ticket reselling! I have season tickets for the Cowboys and had to get a special reseller permit in Texas. Some states consider regular ticket reselling without proper licensing to be "scalping" even if you're selling at or below face value. Also, if you're going the LLC route, make sure you maintain the corporate veil by keeping totally separate financial accounts. I made the mistake of sometimes using my personal PayPal for ticket sales when my business account was having issues, and my accountant said that could potentially compromise my liability protection.

One strategy I don't see mentioned is differentiating between the PSL and the actual tickets. My CPA structured my ticket business so that I personally own the PSLs as an investment asset (since they can appreciate over time), while my LLC "rents" the right to purchase the annual tickets from me. This way, the LLC can deduct the full cost of the annual tickets plus a reasonable "rental fee" for using my PSLs, and I report that rental income personally. This creates some nice tax flexibility depending on my overall situation each year. When/if I eventually sell the PSLs, I'll be taxed at capital gains rates rather than ordinary income. My CPA said this approach works best when the PSLs have significant value like yours do at $80k.

This is exactly the kind of situation where proper planning upfront can save you thousands in taxes and headaches later. One thing I'd add to the excellent advice already given is to consider the timing of when you set up your LLC and start treating this as a business. If you retroactively try to claim business deductions for years when you were just casually selling tickets, that could raise red flags. But going forward, if you formalize the structure and start operating in a businesslike manner, you'll be in much better shape. Also, don't overlook the potential for other revenue streams once you have the LLC set up. Some of my clients have expanded into buying/selling other events' tickets, partnering with other season ticket holders, or even offering ticket management services. The infrastructure you set up for your football tickets can often support additional activities. Just make sure whatever you do, you're genuinely operating with profit motive and keeping detailed records. The IRS hobby loss rules are no joke, especially with high-dollar activities like this.