How to Sell Picks and Shovels in an AI World

Emma Lawler started her career as a product designer at Fitbit, staying through its IPO, and has since founded two companies, sold one, worked at a VC fund, and earned an MBA from Chicago Booth. Her current company, Velvet, is building infrastructure that connects growth teams and engineering teams—a "picks and shovels" play for the AI era. Across her winding path, Lawler has developed a clear set of operating principles about when to bootstrap versus raise venture, how to think about exits, and why the most valuable businesses are often the least glamorous.

The VC vs. Bootstrap Decision

Lawler has lived on both sides of the funding divide. Her first company, Moonlight, was half bootstrapped and half venture-backed. She is clear-eyed about the tradeoffs. Bootstrapping lets you build a sustainable business and keep control, but it takes a long time to reach scale. Venture capital, by contrast, forces high conviction and speed: "You have to convince a bunch of really smart people about it and then do something fast. And if it doesn't work, you get to move on to something else." She acknowledges the stress of being a lottery ticket in a game of lottery tickets, but says she likes that pressure: "It makes me better to have a bunch of other people who are also depending on me for their outcome."