The mechanics of a Cal.com tender
A tender offer is a company-initiated opportunity for employees and investors to sell a portion of their shares back to the company (or to a designated third party) at a set price during a defined window. The window is usually 20 business days under SEC Rule 14e-1. The price is typically set at the most recent preferred round or a discount to it.
How much to tender
The math starts with your concentration percentage. If Cal.com stock is more than 40% of your net worth, participating at meaningful size is usually correct. If it is under 15%, the calculus shifts to tax rate and expected IPO timing; holding through an IPO typically produces a better after-tax outcome if the tender window is priced at a discount to the expected IPO range.
Tax treatment
Same as any secondary sale. Capital gains on shares held more than one year past vest or exercise; ordinary income on disqualifying-disposition amounts. $
Frequently asked
- Is Cal.com stock publicly tradable?
- No. Cal.com is a late-stage private company. Shares can only be transferred through private sales subject to the company’s transfer restrictions; no active secondary market has been confirmed publicly.
- When should I exercise ISOs at Cal.com?
- The answer depends on the current 409A, your own AMT capacity, and the probability of a liquidity event in the next 12-24 months. Model AMT before any exercise larger than $50k of bargain element.
- Does QSBS apply to my Cal.com stock?
- Potentially, if Cal.com was a C-corporation at issuance with under $50M in gross assets, and you acquired the stock at original issuance (or via ISO/NSO exercise) and will hold it five years from acquisition. Request a QSBS attestation letter from the company before you need it at sale.
- Should I participate in a Cal.com tender offer?
- Usually yes for some portion, to reduce concentration risk. The full-stack question is: what percentage of your net worth is in Cal.com? What's the tender price versus 409A? What's your tax rate on the gain? Run the secondary-sale calculator before responding.