How Running Out of Money Made DocSend a $165M Success

Russ Heddleston, founder of DocSend, shares how nearly going bankrupt forced them to rethink everything—turning a failing startup into a product-led rocket ship that Dropbox bought for $165M. From spreadsheets of startup ideas, to the painful lessons of chasing enterprise sales, to doubling their prices and watching conversions skyrocket, Russ breaks down the hard truths behind building a breakout SaaS company. Plus: why he wishes he hadn’t sold, and what he’s doing differently with his next startup.