trading in New York and New Jersey, including stints at Salomon Brothers and The Prudential Home Mortgage Company. Then he went back to school and got his law degree from the University of Michigan.
In 1998, Entress made his trek to the Northwest. He took a job in Seattle with Perkins Coie as a securities lawyer, where he worked on IPOs and other corporate transactions on the verge of the most lucrative, and bubbly, moment in stock market history. Given what was happening in the world, it seemed like a good time to start a company. In 1999, he was bitten by the tech startup bug and co-founded UrbanEarth.com, a digital music company where he served as chief financial officer. The firm went belly-up during the dot-com bust, but the experience taught Entress a couple of important lessons that were valuable to him over the ensuing years.
First, setting up basic servers and Web technologies took his team months in 1999, but can now be done in days—that’s why startup costs are so much lower. Second, timing is everything. For instance, UrbanEarth had a term sheet from VCs in the spring of 2000, but the Internet bubble burst, and the money went away. “Being early will kill you,” he says. “I tell entrepreneurs, ‘I’ve seen 50 or 100 companies that were doing something similar—why was the timing wrong when they did it, and what’s different now?’”
Failure at his first startup didn’t scar Entress. On the contrary, he has studied failures carefully and learned a great deal from them. And in fact, he forged one of his close friendships, with Alex Algard, the founder of WhitePages.com, during that hard time. The two would later co-invest in The Coffee Equipment Company in their first deal together.
Still, Entress needed something more challenging, and found it at Madrona Venture Group, where he spent eight-plus years as a VC. But all the while, he never stopped making independent angel investments in a few companies, like PDA Verticals and World Wide Packets in the early days. His biggest hit (so far) would turn out to be Isilon Systems, the data storage firm which he invested in back in 2000, alongside Madrona. The company went public in 2006, raising $108 million in an IPO and making its early investors a lot of money.
What was the most important thing he learned at Madrona, and then Voyager? “I really love early-stage investing—at the earliest stage,” Entress says, because he can “help build something from the ground up.” Some examples from his VC days: He first met Isilon when it was two guys, he says. Redfin (originally called Appliance Computing) was three guys. And he gained a lot of perspective working with companies like BuddyTV, World Wide Packets, Seadragon, ShareBuilder, and SinglePoint. What’s more, his experience with BuddyTV opened the door to another investing partner, CEO Andy Liu, as well as Internet marketing guru Neil Patel and Ben Huh of Cheezburger fame. Later on, with Voyager Capital, he helped advise and build Ground Truth, Elemental Technologies, and most recently, Bonanzle.
DeVore, the co-leader of Founder’s Co-op, says the first time he got to know Entress was around 2007. That’s when DeVore and Andy Sack were thinking about investing in Cheezburger Network (formerly called Pet Holdings) and “foolishly passed,” DeVore says. “He was known as a VC, but what
