"I understood that line intellectually, but I didn't feel the weight of it until I began seeing deals up close. At one firm I worked with, we did what I call "friend deals." These were checks written due to pressure, access or favors. The terms made little sense. The alignment was nonexistent. These deals created years of friction in exchange for a few months of relief."
"No amount of capital can bridge a fundamental philosophical divide. I have witnessed partnerships fall apart because the founder sought a steady, durable business, while the investor pushed for an early exit. Or the founder wanted to prioritize product quality while the investor cared only about margin. I lived this dynamic once while evaluating an investment in a noodle company. The business had traction and even a Walmart contract. The founder had poured in his own savings."
Not all capital is beneficial; misaligned investor-founder relationships cause enduring problems that outweigh immediate financial relief. Checks written from pressure, access or favors often carry terms and misalignment that produce years of friction. Founders frequently regret fast closes when values, expectations, trust or working style differ. Capital cannot bridge fundamental philosophical divides such as differing exit timelines or priorities between product quality and margin. Due diligence on prior interactions and pressure-handling can justify passing on apparently reasonable deals, since alignment and behavioral fit determine partnership durability as much as valuation or speed.
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