Guides

Start with what happened

• You’re harvesting losses before year end: Tax-loss harvesting checklist: the positions your brokerage can’t show you
• The founder stopped answering: The startup I invested in went silent. Can I write it off?
• The founder answers, but never with a date: The founder says they’re still exploring options. What does that mean for my position?
• You’re weighing the three ways out: Selling vs. abandoning a dead startup position

Start with what you hold

• Startup stock: Worthless-security deduction or sell it: which is better?
• A SAFE: My SAFE never converted. Is that a tax loss?
• A convertible note: How do I write off a failed startup investment?
• An LLC, LP or fund interest: I keep getting an all-zero K-1 that’s never marked final. How do I get it off my books?

For investors

If you hold a position that stopped reporting, these start where you are.

• The startup I invested in went silent. Can I write it off?

  No K-1, no 1099, no dissolution notice — just silence. What that means for claiming a loss, the two paths available, and what your advisor will need from you.

• How do I write off a failed startup investment?

  There are two ways a loss on a private investment reaches a tax return: claiming it worthless, or selling it. What each requires, and how to tell which case you’re in.

• My SAFE never converted. Is that a tax loss?

  A SAFE that never turned into shares has no conversion event and no maturity date. What that does to a loss claim, and why a sale is often the only dated event available.

• I keep getting an all-zero K-1 that’s never marked final. How do I get it off my books?

  An LLC or fund interest that’s dead but still files: why the zeros keep arriving, what they cost you, and the two ways a partner stops being a partner.

• Tax-loss harvesting checklist: the positions your brokerage can’t show you

  A year-end loss-harvesting checklist that starts with your brokerage screen and ends with the private positions no screen reports — SAFEs, notes, angel stock, LLC interests — and the three ways a loss on one can reach a return.

• The founder says they’re still exploring options. What does that mean for my position?

  The company didn’t go silent. The founder still answers — “exploring a few options,” “some acquisition interest” — and never gives a date. Why that’s harder than silence for a loss claim, and what a sale asks of the founder: nothing.

• Selling vs. abandoning a dead startup position

  An advisor may raise three paths for a dead private position: a claim with no transaction, an abandonment, or a sale. What each one is, and what each involves in practice.

For advisors

The mechanics of a documented sale, for the person preparing the return. The white paper is the long version.

• Worthless-security deduction or sell it: which is better?

  A side-by-side of the two ways a loss on a dead private investment reaches a return — what each requires, what each avoids, and where each one fails.

• The white paper

  The reporting mechanics of a nominal-consideration sale and the authorities relied on, in full.

For founders

If it’s your company they’re asking about.

• You haven’t closed the company. Maybe you never will. Your investors don’t need to wait for a formal closure.

  Your investors keep asking when you’ll dissolve the company. You haven’t, and maybe you never will. They don’t need to wait for a formal closure. A guide for founders whose company stopped but never formally closed.