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Jonathan Haaswritingnowusesabout

The Secondary Celebration: A Founder's Perspective on VC Liquidity Events

April 16, 2025·2 min read

During my morning LinkedIn scroll, I came across yet another post from a venture firm celebrating a massive return multiple from a secondary transaction.

#entrepreneurship#founder-advice#investor-dynamics#liquidity-events#secondary-transactions#startup-culture#venture-capital

A venture firm posts a LinkedIn celebration: massive return multiple from a secondary transaction. Impressive metrics. Enthusiastic self-congratulation. An afterthought mention of the founders who made it possible.

The founders, meanwhile, are still locked in. No liquidity. Full concentration risk. Same existential pressure they've carried for five years. The investor's victory lap is, structurally, a celebration of extracting value from an outcome the founders haven't reached yet.

The Asymmetry

The core problem is risk distribution. VCs spread bets across a portfolio. A single company's failure is a write-off, not a career-ending event. Founders concentrate their entire professional and financial risk in one venture. When a VC realizes gains through a secondary sale years before the founder can access meaningful liquidity, the misalignment isn't theoretical. It's economic.

I've watched this play out in board meetings. The room's energy shifts the moment an investor starts calculating their return multiple from a proposed secondary arrangement -- right in front of the person who sacrificed five years to build the thing being valued. One founder told me afterward that their life's work felt reduced to a spreadsheet cell. That image hasn't left.

The Signaling Problem

How you celebrate reveals what you value. When a firm broadcasts "fund-returning" multiples while founders remain fully exposed, it tells current and future founders something specific: this firm optimizes for its own liquidity timeline, not the company's outcome.

Returns matter. They're how venture capital functions, and communicating them to LPs is a fiduciary obligation. But there's a difference between reporting returns to your investors and broadcasting them to the ecosystem. The first is business. The second is positioning -- and it positions the firm as a financial intermediary, not a company-building partner.

The Practical Implication

For founders evaluating investors: look at how firms communicate their wins. Do they center the company's achievement or their own return? Do they acknowledge the asymmetry or ignore it? This is a reliable signal of how the relationship will feel when it matters -- at the board table, during a down round, when the secondary opportunity arrives.

For VCs: consider how your celebration posts read to the founders still building the company that delivered your returns. The best investor-founder relationships are built on the recognition that your liquidity event is their ongoing risk. Communicating accordingly isn't PR strategy. It's respect.

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