Club Penguin's co-founder warns that accepting VC money creates immense pressure to become a billion-dollar company. This often crushes otherwise successful businesses that could have been profitable at a smaller scale, making founders worse off in the long run.

Raising too much money at a high valuation puts a "bogey on your back." It forces a "shoot the moon" strategy, which can decrease capital efficiency, make future fundraising harder, and limit potential exit opportunities by making the company too expensive for acquirers.

While first-time founders often optimize for the highest valuation, experienced entrepreneurs know this is a trap. They deliberately raise at a reasonable price, even if a higher one is available. This preserves strategic flexibility, makes future fundraising less perilous, and keeps options open—which is more valuable than a vanity valuation.

The first question in any fundraising or M&A discussion is always, 'What was your last round price?' An inflated number creates psychological friction and can halt negotiations before they begin. Founders should optimize for a valuation that allows for a clear up-round, not just the highest price today.

Accepting too high a valuation can be a fatal error. The first question in any subsequent fundraising or M&A discussion will be about the prior round's price. An unjustifiably high number immediately destroys the psychology of the new deal, making it nearly impossible to raise more capital or sell the company, regardless of progress.

Valuations don't jump dramatically; they 'sneak up on you.' An investor might balk at a $45M cap when they expected $40M. But the fear of missing a potential unicorn is stronger than the desire for a slightly better price, causing a gradual, batch-over-batch inflation of valuation norms.

A stock price disconnected from fundamentals can be a powerful tool. As seen with Meta in 2022, a low stock price hinders recruitment. Conversely, a high stock price acts as a valuable currency for equity compensation, allowing companies to attract and retain elite employees, even if investors are skeptical of the valuation.

Dan Sundheim argues successful private companies should avoid going public. Public market volatility means stock prices, and thus employee compensation, are driven by sentiment, not fundamental value creation. Being dramatically overvalued can be as harmful as being undervalued, as it misaligns incentives for future hires.

While a high IPO valuation seems like a victory, it can be destructive internally. When the stock inevitably corrects, employees experience the drop as a personal loss due to psychological loss aversion, leading to distraction and depression. CEOs should nudge markets toward sane, sustainable valuations.