The founders of Pipe, once valued at $2B, took significant money off the table via secondary sales before stepping back from operational roles. When the company's performance subsequently cratered amid operational missteps, it created deep resentment among investors and employees who were left holding devalued equity.

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Successful founders prioritize cash upfront over potentially larger payouts from complex earnouts. Earnouts often underperform because founders lose control of the business's future performance, leading to dissatisfaction despite a higher on-paper valuation.

ElevenLabs raised a $100M round entirely for employee secondaries. The CEO's rationale is that by allowing early team members to de-risk and realize financial gains, it solidifies their commitment to the company's multi-year mission rather than creating pressure for a quick exit.

In today's founder-centric climate, many VCs avoid confrontation to protect their reputation (NPS) within the founder network. This fear of being blacklisted leads them to abdicate their fiduciary duty to shareholders, failing to intervene even when a company's performance is dire and hard decisions are needed.

The trend of allowing employees to sell shares in secondary transactions before investors get liquidity is a problem. Lior Susan argues this creates a fundamental misalignment, as historically, employees and investors realized returns at the same time. The system needs rethinking for long-duration private companies.

Taking a small amount of money off the table via a secondary sale de-risks a founder's personal finances. This financial security empowers them to reject large acquisition offers and pursue a long-term, independent vision without the pressure of life-changing personal wealth decisions.

Vested works directly with employees because startups find small, one-off secondary transactions burdensome due to legal fees and cap table complexity. However, this dynamic inverts at scale. Once Vested facilitates millions in transactions for a single company's stock, the startup has a strong incentive to partner on a formal liquidity program.

The rise of founder-optimized fundraising—raising smaller, more frequent rounds to minimize dilution—is systematically eroding traditional VC ownership models. What is a savvy capital strategy for a founder directly translates into a VC failing to meet their ownership targets, creating a fundamental conflict in the ecosystem.

Raising significant venture capital diluted founder Ty Haney's ownership to just 10%. When strategic disagreements arose with the board over growth, she lacked the decision-making control to steer the company, leading to an untenable situation and her forced departure.

The number of founders taking secondary liquidity after their seed round is twice as high as the 2021 peak. While this de-risks the journey for founders, there is almost no parallel liquidity offered to early employees, creating a growing divide in early-stage risk and reward.

Exiting a cash-flowing business swaps a continuous income stream for a finite pot of money. This psychological shift can create deep financial insecurity as founders must now protect capital rather than generate it, even if they are objectively wealthy.