Risks and Rewards

Jeffrey Wald

Jeffrey Wald ’95 CIPA ’96 helps the next generation with the ins and outs of startups

Entrepreneur and co-founder of software company WorkMarket, Jeff Wald ’95, MPA CIPA ’96, has built up and sold several technology companies, advises and invests in startups, and regularly speaks to entrepreneurial groups, accelerators, and startups about the ins and outs of the startup world and the future of labor markets.

After graduating from Cornell, Wald earned an MBA from Harvard Business School and worked as an investment banker with JP Morgan and investment firm GlenRock, where he had the opportunity to meet a host of entrepreneurs, including frequent collaborator Jeff Leventhal.

“I was just so enamored with the idea of somebody taking the risk and all the things inherent in that risk to try to bring something new to market, to try to do something better,” he said. “To me, that was the epitome of the American ideal, this notion of: I’m going to go out on my own because I think there’s a better way this can be done and I’ll take the risk and I’ll reap the reward for that risk.”

One key lesson he shares with early-career entrepreneurs: failure is not only an option when venturing into the world of startups, it is the highest probability outcome.

“When it happens, it’s not some massive indictment against you,” he explained. “You’ve got to pick yourself up, dust yourself off, and get back in and try again, and again, and again.”

That is exactly what Wald did when SpinBack, a company he founded with Leventhal in 2006, failed in 2007 and nearly bankrupted him. Wald said at the time he was unprepared for that kind of failure.

“I think it’s important that those of us who have failed talk about the experience,” he said. “People have too-negative an association with failure and those who have failed, and that certainly applied to me when SpinBack fell apart. I didn’t know how to deal with it or what to do. The shame of having failed was challenging. I hope that others who go through it can take some comfort from the lessons of those of us who have been down that road.”

SpinBack was rebuilt in 2010 with the support of Wald and Leventhal and sold to Buddy Media in 2011, which was subsequently sold to Salesforce for around $800 million.

Founded in May of 2010 and acquired by ADP in 2018, WorkMarket is an enterprise software platform that enables corporations to efficiently and compliantly organize, manage, and pay freelancer labor.

Wald described the role of a founder as setting the vision of where the company is heading, setting the path that will bring it to that end point, raising money, and building a solid team, but, he said, the day-to-day of a startup founder is often focused on much more mundane problem-solving.

“In the early days, and this is something I say at a lot of conferences, the most important thing I’ll do on any given day is plunging the toilet,” he said. “WorkMarket is a big company now, but in the beginning we were twenty people in a very rundown, very gritty, grimy building in Chelsea and there’d be cockroaches and mice and the toilet would back up a lot due to old plumbing.”

Now in the Garment District near Penn Station, there are around 160 members of the WorkMarket team.

In addition to serving as WorkMarket president and his speaking schedule, Wald is currently writing a book, The End of Jobs: The Rise of the Agile Company and the On-Demand Worker, which he expects to be out by the end of the year.