In this installment of the CEO Supper Club, we talk about fundraising and the importance of leverage.

We notice a correlation: Young Aaron Levie of Box has the most gray hair and has also raised the most money at a whopping $160 million. “There’s a new patch for every round I’ve raised,” he says.

Comparatively, Atlassian was bootstrapped for eight years, and Jive was bootstrapped for six. That gave them enviable leverage when it came time to raise funds. Atlassian president Jay Simons tells the story of that epic funding round…sort of. I tell the story of taking a newborn baby on the fundraising trail, and we try to explain the concept of an amuse-bouche to Levie.

(Here are our earlier segments about Phablets and industry consolidation.)