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How Investors Kill Their Own Startups

Capital 🖤 Letters1:39

Transcription

First time founders hate this one trick, but seriously, you built a product, you built a company, the team, but you're a first time founder with zero dry powder and your cap table is about to become a crime scene.

Everybody thinks that sweat equity is this impenetrable shield, but when the market starves, your lead investors will execute a weaponized insider round to bury you alive, and I've seen this happen.

When your startup bleeds cash, your sponsors are going to offer you a lifeline, but this is a calculated pay to play extraction. They say, "Hey, instead of raising outside money, let's do an inside round. We can keep more of the equity." And they launch an inside round, forcing you to inject hundreds of thousands of dollars in order to maintain your stake.

They already know that your personal bank account is empty because you can't write a check; the penalty is a brutal, brutal cram down. Because you lack the capital, the mechanics are ruthless. The sponsors force a massive reverse split, sometimes 10 to 1. They convert your preferred shares into common stock, which instantaneously annihilates your liquidation preference. It erases your anti-dilution protections and it strips away your board seat, sometimes. Your legacy equity is systematically dissolved.

The apex predators, they consolidate absolute control over this distressed asset, or sometimes not distressed at all asset, while you just watch from the sidelines of your own game. This is the fundamental physics of distressed corporate finance. When the leverage shifts, sweat equity means nothing without the cash to defend it. The pie doesn't grow; the pie is violently resliced, and because you were broke at the start, you're just left starving.

Look, loyalty ends where leverage begins. You're out of cash. Hey, hit subscribe if you want to know how these things work and how to get term sheets.