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Despite raising $380M and hitting $187M in revenue, Boxed's co-founder owned a low single-digit percentage at IPO and did not achieve significant personal liquidity. This is a cautionary tale against the 'growth at all costs' mindset, which can heavily dilute founders in low-margin businesses.

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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.

Reflecting on his journey with VC-fueled Boxed, the founder argues the startup ecosystem has shifted. He believes the 'growth at all costs' era is over, replaced by a 'peak bootstrap era' that prioritizes capital efficiency, doing more with less, and leveraging AI.

Mark Cuban highlights the conflict for founders with VC funding: VCs need rapid growth for an exit, which can force founders into risky decisions that dilute equity below 50% and risk the company's long-term health.

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.

A business transitions from a founder-dependent "practice" to a scalable "enterprise" only when the founder shares wealth and recognition. Failing to provide equity and public credit prevents attracting and retaining the talent needed for growth, as top performers will leave to become owners themselves.

Chasing high, unrealized valuations is dangerous. It makes common stock prohibitively expensive, undermining the potential for life-changing wealth for employees—a key recruiting tool. It also narrows a company's strategic options, locking it into a high-stakes path where anything less than exceeding the last valuation is seen as failure.

A $33M exit sounds huge, but Scott Galloway only took home $2-3M. This was because he owned just 20-30% of the company and had to split proceeds with his ex-wife. It's a powerful reminder that founder equity and personal circumstances, not the sale price, determine the actual take-home amount.

Despite landing on the Inc. 5000 list, the company was losing money on a massive scale. The 'growth at all costs' mindset meant they ignored profitability, with founders admitting they didn't even know what COGS were.

Even with strong revenue growth, founders should seriously consider M&A offers if their Total Addressable Market (TAM) isn't expanding at a faster rate. A stagnant TAM indicates a future ceiling on value creation, and selling may be the optimal outcome before hitting that wall.

The founder advises against always pursuing the highest valuation, noting it can lead to immense pressure and difficulties in subsequent rounds if the market normalizes. Prioritizing investor chemistry and a fair, responsible valuation is a more sustainable long-term strategy.

Boxed's Founder Owned Just 2.6% at IPO, Highlighting 'Growth at All Costs' Risk | RiffOn