How to cash out in Silicon Valley - without setting off alarms
Briefly

In startup environments, seeking payouts can be perceived as a betrayal. To regain liquidity, both founders and early backers are increasingly utilizing the secondary market to sell portions of their shares. This practice, while necessary, is delicate, as it may incite backlash from stakeholders and suggest a lack of confidence in the startup's future. Investors and founders must navigate the timing, pricing, and presentation of secondary sales to avoid negative market implications and retain investor trust.
In startup land, wanting a payout can look like betrayal. Early startup backers and founders are increasingly turning to the secondary market to get some cash back on their shares.
Cashing out a portion of shares can trigger board backlash, founder resentment, or signal to the market that the rocket ship might be losing steam.
It's not open season for secondaries; timing, pricing, and branding the transaction are critical to avoid catastrophic market signals.
A secondary sale by a Series A lead at a lower valuation sends bad signals. If they lack confidence, why would subsequent investors buy in?
Read at Business Insider
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