Christopher Mastrangelo

I began my career in the corporate department at McDermott Will & Schulte LLP, where I worked on mergers and acquisitions, corporate finance, private equity and real estate. After several years training under some highly respected attorneys, I knew I was meant to do something different. I left the secure law firm life and ventured into the new and unstable realm of e-commerce.

A client and I collaborated to launch a high-fashion retail e-commerce platform, Karmaloop, Inc. In the beginning I performed every role the company needed: general counsel, human resource manager, clothing buyer, customer service representative and, even at times, office cleaner. Following a $30 million infusion from Insight Venture Partners, the company's growth necessitated my focused attention on the formalized roles of Chief Operating Officer and General Counsel.

In those roles I managed 350 employees, negotiated and monitored over $100 million in third-party contracts (including Google, eBay Fulfillment and Facebook), supervised the fulfillment and shipping of over 40 million packages yearly, and collaborated with outside counsel to accomplish over $100 million in secured debt and equity raises. The company grew to over $130 million in annual revenue and over $1 billion in total sales.

Its growth peaked coincident with declining e-commerce valuations, and both ultimately led to the company's need to restructure. After shepherding it through that complex and painful process, I made my exit. That part of the story matters more than the revenue figure does: I have been in the room when a company runs out of room.