You can bootstrap your business to scale, but you’ll have to make your own luck. Nobody knows this better than Mailchimp’s Ben Chestnut. He used a DIY ethos to grow a $600M company without ever raising a dollar of outside funding. The Mailchimp story is the exception to Reid’s rule (Generally: Raise more money than you think you need!). The episode explores a range of options for those who don’t fit the VC-funding mold for any set of reasons. Cameo appearances: LeVar Burton (Star Trek, Reading Rainbow, LeVar Burton Reads), Don MacKinnon (Milq), Karen Cahn (iFundWomen).
Early-stage startups are a lot like pirate ships – they need a buccaneering spirit to survive. But every startup needs to shed its pirate nature at some point, and evolve into something more akin to a navy – no less heroic, but more disciplined. Dara Khosrowshahi, as Uber CEO, took on the most extreme pirate-to-navy transition in startup history. Though Uber blitzscaled to become the most valuable startup in the world, it was also notorious for its toxic culture – and Dara turned the company around. His method? Truth-telling and doing the right thing. Cameo appearances: Arianna Huffington (Thrive Global) and Ben Chestnut (Mailchimp).