A startup job is an investment, after all: Venture capitalists may wager money, but you're staking something more precious - your time. And unlike VCs, you can't spread your risk by betting on a bunch of companies at once. Start with TAM. That's 'total addressable market,' and if it's not big enough, there's no point in talking.

Hubspot's leaders were not heroes but rather a pack of sales and marketing charlatans who spun a good story about magical transformation technology and got rich by selling shares in a company that still has never turned a profit.

There are too many ways that a startup gig can go sideways. If the startup won't agree to hefty severance, pass.

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