Should You Quit Your Job At A Unicorn?

The hosts note that there are about 1,400 unicorns and speculate that perhaps a third will go public successfully. Employees who joined late may have options with high strike prices, which could be underwater if the company is sold below its valuation. Acquisitions may also require employees to interview for their jobs again.

Michael suggests looking at revenue and whether it is growing. He says $50 million to $100 million or more can help justify unicorn status, while a company below $50 million should prompt questions about retention, pricing, and product-market fit. Employees can examine whether customers onboard, keep using the product, and renew.

A recent fundraising announcement may not mean a company just raised money; a round can be announced long after it closed. Michael says employees with experience at a late-stage startup might find more responsibility and equity at an earlier-stage company. One attractive comparison would be an earlier-stage company with similar revenue but a much lower valuation.

The hosts caution that leaving can look like the wrong choice later, so employees should assess the evidence rather than follow hype. They suggest watching whether founders and senior managers are engaged, whether all-hands messages match the facts, and whether capable colleagues are doing important customer work. A departing workforce, make-work, or management dismissing bad numbers may signal trouble.

The hosts warn against switching jobs every 12 or 18 months, which can make it harder to build expertise and a career. If the metrics are excellent, leadership is focused, and colleagues are strong, they suggest staying and considering ways to take on more responsibility or equity. The unicorn label alone does not guarantee a valuable outcome.