Eco-Motors, funded in part by Khosla Ventures, has to decide how to go to market with a new technology for internal combustion engines for automotive and industrial use. The OPOC engine has opposed pistons and is a two-stroke engine, as compared to a more traditional in-line or V-oriented 6, 8, or 12 cylinder gas or diesel engine. A two-stroke engine is cheaper to build and has higher power output than a four-stroke engine but historically has been more polluting. At present in the U.S., two-stroke engines are mostly deployed in lawnmowers and chainsaws with four-stroke engines the leaders in cars, boats, and generators. Should the company be an invention company licensing its technology; an engine designer and manufacturer selling to auto, marine, and fixed OEM companies; or a fully integrated power and transport solution? How is the value chain currently organized, what obstacles are there in going to market, and how can this company thrive with this innovation that is cleaner and cheaper than the incumbent but hard to explain and to deploy?

Simon Rothman had recently been promoted from executive-in-residence to Partner at esteemed venture capital firm Greylock Partners and placed in charge of managing a $100 million early-stage fund commitment dedicated to online marketplaces. In Greylock's view, 2014 was a special moment in time for online marketplaces, the beginning of a boom in the space that was being catalyzed by mobile technology and social identity. Rothman was the right man for the job. An early eBay employee, he had founded eBay Motors and turned it into a multi-billion dollar business and also advised several successful online marketplaces such as Lyft, Wanelo and TaskRabbit. For his first investment as Partner, Rothman was particularly interested in the food delivery space, which was ripe for disruption by online marketplaces. Rothman had five food delivery startup options to choose from, a philosophy on how to analyze marketplace businesses, and a few weeks to make his first ever investment as a Partner at Greylock.