Will TBPN Merch Work as an Expense Report? An Investigation
The moment the OpenAI acquisition was announced, someone in our Discord asked a question so pure, so beautiful, so perfectly engineered for the overlap of tech culture and financial optimization that we had no choice but to investigate: "If TBPN is owned by OpenAI, and I work at OpenAI, is TBPN merch now company merchandise? Can I expense it?"
We are not accountants. We are not tax professionals. We are a podcast merch team that now reports to the same corporate umbrella as ChatGPT. But we did what any responsible media organization would do: we asked a lot of questions to people who know more than we do, read some IRS publications that made our eyes water, and produced this semi-authoritative guide to expensing TBPN merchandise.
Disclaimer: This post is for entertainment purposes. Please do not cite "the TBPN blog" in correspondence with your finance department. We are begging you.
Scenario 1: You Work at OpenAI
The Argument For Expensing
TBPN is a subsidiary of OpenAI. TBPN merch features the brand of a company that OpenAI owns. Wearing TBPN merch to the office is, functionally, wearing company merchandise. Many companies provide branded apparel to employees as part of their onboarding. If OpenAI provides OpenAI-branded hoodies (they do), and TBPN is an OpenAI property, then a TBPN hoodie is, by the transitive property of corporate ownership, company swag.
IRS Publication 463 allows deductions for "work clothes and uniforms" if they are required as a condition of employment and not suitable for everyday wear. A TBPN hoodie is... let's say... debatably not suitable for everyday wear if you consider it a uniform. The "required as a condition of employment" part is harder to argue unless your job is specifically to promote TBPN, in which case you might actually have a case.
The Argument Against
Subsidiaries are not the parent company. Disney owns ESPN, but an ESPN hat is not Disney corporate merchandise. If you work at OpenAI's SF office and show up in a TBPN t-shirt, your manager is going to say "cool shirt" not "thank you for repping the brand." There's a difference between corporate swag and merch from a company your company happens to own. Your finance team knows the difference. So does the IRS.
Verdict: Probably Not, But We Admire the Energy
The most likely outcome of submitting a TBPN merch receipt as an expense at OpenAI is a politely confused email from Accounts Payable followed by a rejection. The second most likely outcome is that the email gets forwarded around the finance team, someone screenshots it, and it ends up in an internal Slack channel where it becomes a minor meme. The third most likely outcome — and the one we're rooting for — is that someone in OpenAI leadership sees it and decides to actually make TBPN merch part of the employee swag program. We're speaking this into existence.
Scenario 2: You Work at a Tech Company That's Not OpenAI
The Argument For Expensing
TBPN is a professional development resource. The show covers technology news, business strategy, fundraising, and industry trends. Watching TBPN is research. Wearing TBPN merch is... advertising that you do research? Under IRS Section 162, business expenses must be "ordinary and necessary." If your job involves staying current on technology trends, consuming TBPN content is arguably necessary, and purchasing merchandise from a professional resource could be categorized as a subscription or educational material expense.
This is a stretch. We know this is a stretch. But stretches are what make expense reports interesting.
The Argument Against
A hat is not a subscription. A mug is not a textbook. A bomber jacket is not a conference fee. No matter how much you learn from TBPN, the physical merchandise is apparel, and apparel is personal. If you could expense podcast merch as professional development, every startup employee in San Francisco would have a wardrobe funded by their Series A.
Verdict: No, But Points for Creativity
Your company will not reimburse you for a TBPN hoodie under "professional development." However, if your company has a discretionary "culture budget" or "team morale" line item, buying TBPN merch for your team's watch party is actually defensible. Group viewing of TBPN has become a real thing at tech companies, and outfitting your watch party crew in matching tees is a team-building expense. Frame it right, and it might fly.
Scenario 3: You're a Content Creator or Journalist
The Argument For Expensing
This one might actually work. If you're a content creator who covers tech, and you create content that references, reviews, or discusses TBPN, then TBPN merch is a prop. Props are a legitimate business expense for content creators under IRS guidelines. The t-shirt appears in your video. The mug appears on your desk during your podcast. The sticker appears on the laptop you use in your tech review background.
YouTube creators and podcasters regularly deduct merchandise and props used in content production. As long as the TBPN merch appears in content that generates revenue, and the purchase is documented as a production expense, this is genuinely defensible.
The Argument Against
You have to actually use it in content. Buying a TBPN hoodie, wearing it to brunch, and claiming it as a business expense because you "might film something later" is not going to hold up. The item needs to appear in revenue-generating content. If it's sitting in your closet, it's personal apparel, no matter what receipt you file.
Verdict: Actually Yes, If You Follow the Rules
Content creators covering tech: buy TBPN merch, feature it in your content, document the usage, and deduct it as a production prop. This is legitimate. You're welcome.
Scenario 4: You're an OpenAI Investor
The Argument For Expensing
You own equity in a company that owns TBPN. Purchasing TBPN merch is supporting a revenue stream of a company in your portfolio. Under this logic, buying a TBPN hoodie is essentially reinvesting in your own position.
The Argument Against
This is not how investing works. This is not how expenses work. This is not how anything works. Your accountant will fire you as a client.
Verdict: Absolutely Not, But the Logic Is Beautiful
Scenario 5: Conference Attire
The Argument For Expensing
Here's where things get genuinely interesting. If you attend tech conferences — and if you work in tech, you probably do — what you wear is a professional consideration. Many companies reimburse "conference attire" as a business expense. TBPN merch is increasingly recognized at tech conferences as a tribal identifier. Wearing a TBPN polo to a conference signals industry awareness, cultural fluency, and good taste. It's more than fashion — it's networking infrastructure.
The Argument Against
The IRS has historically been skeptical of clothing deductions unless the clothing is specifically required for work and not adaptable for general use. A TBPN polo is adaptable for general use. You could wear it to dinner. You could wear it to a barbecue. Its versatility is actually its downfall as an expense.
Verdict: Depends on Your Company's Expense Policy
If your company has a broad "conference expenses" category that includes attire, and you wear the TBPN polo to a conference, and you have a receipt, this might actually survive an expense audit. It's the most legitimately defensible scenario in this entire investigation. Not because of tax law — because of corporate expense policies, which are often more generous and less scrutinized than IRS guidelines.
The Real Answer
Can you expense TBPN merch? Almost certainly not in any way the IRS would approve. Should you try? We're not saying yes. We're saying that Fortune 500 companies have expensed significantly more absurd things, and at least a TBPN tee actually looks good.
What we can say is this: TBPN merch is now technically a product of an OpenAI subsidiary. That sentence alone is worth the price of a sticker.
Shop the surprisingly-hard-to-expense collection at the TBPN Store. Browse hoodies, jackets, hats, mugs, and polos. Receipts provided for your totally legitimate business purposes.