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Fixing a Missed 83(b) Election

Fixing a Missed 83(b) Election

“You filed your Section 83(b) election, right?” Silence. “Right?” I gave a presentation years ago on how to fix a missed tax code Section 83(b) election. My phone started ringing the moment I returned to my office. Turns out, these get missed. Apparently, founders...
Transferring a Stock Option

Transferring a Stock Option

I occasionally get asked whether it is possible to transfer a stock option. Listed below are relevant considerations.  Does the plan allow for it?  Carefully read the stock option plan and agreement to see if there are any restrictions on option transfer. There...
Year-End Tax Moves

Year-End Tax Moves

You’ve got about three weeks left in 2025, which means there’s still time for some last-minute, tax planning. Here are ten ideas to consider before December 31: 1. Accelerate deductible business payments (cash-basis taxpayers)If you own or operate a cash-basis...
Secondary Purchase plus Exchange

Secondary Purchase plus Exchange

Updated. Originally posted November 3, 2022. Over the past six years, a particular method for providing founder liquidity has gained significant popularity: an investor purchases common stock from founders during a preferred financing at the preferred price. The...
What’s Lurking in Your Cap Table?

What’s Lurking in Your Cap Table?

What’s Lurking in Your Cap Table? A clean capitalization table (or “cap table”) isn’t just good housekeeping—it’s a critical part of maintaining your company’s legal and tax health. Yet many founders discover, often too late, that their cap table hides costly issues...