Idea · carried by 1 source
Hire Second-Time Employees
Target employees who are on their second (or later) company — not new grads. Second-timers have been through six funding rounds and four pivots with nothing to show for it. They understand dilution, preference stacks, and the real math of equity. The value proposition of no-dilution equity and annual liquidity resonates instantly.
Where it comes from
William Hockey, explaining Column's hiring strategy, in highlights/william-hockey-bet-on-yourself (~25:19): “We target people that this is their second company. Like we are probably not the best place for a new grad to land.”
How it works
- New grads follow social proof: They look at “where all of my friends going. What is the number one company in Hacker News I read all the time.” They can't evaluate equity structures properly.
- Second-timers have scar tissue: They understand dilution and preference stacks from experience. “It's a hard story for a 21-year-old. It's actually a pretty easy story for a 25-year-old that's been through like six rounds and four pivots at their previous company and don't have anything to show for it.”
- The equity story lands: “We go to people and we're like, 'Hey, we're super fast growing, but we provide you yearly liquidity. Oh, by the way, here's some very basic math on preference and dilution. And here's why you can actually make way more money for the same equity value.'”
- Prior experience is leveraged, not wasted: “If you could [fail forward] on somebody else's dime, amazing.” Working at an early-stage company before founding is “like you just get fail forward all the time.”
- Almost no regretted attrition: “We have almost close to no regretted attrition, which means people that we'd like to stay end up staying.”
The best hires aren't the ones dazzled by a big valuation number — they're the ones who have learned through experience that equity on paper and equity in the bank are two different things. Sell them on what they'll actually take home.