After graduating from Binghamton University, Andy Appelbaum, ‘88, enrolled at New York University School of Law and went on to work at a law firm called Latham and Watkins. However, just one year into his professional career, Appelbaum left the firm to start a dry cleaning delivery service.
His subsequent string of entrepreneurial endeavors included co-founding Seamless, the nation’s largest online and mobile food ordering company. Now, he is a venture capitalist for RiverPark Ventures.
Appelbaum spoke to a group of 30 BU students on Tuesday in New York City, as a part of a full-day trip in which they attended a job fair and heard from various innovators and entrepreneurs.
Thinking back to his days at BU, Appelbaum said he always had a mind for innovation despite his pre-law track.
“I think that deep somewhere down in my heart I was always sort of a version of an entrepreneur,” Appelbaum said. “I used to promote bars in Binghamton. I would hire underclassmen, and people didn’t really care where they went; they just needed to go where everyone else was going to be.”
Appelbaum excelled in his ventures by acting as an intermediary between customers and companies. The dry cleaning delivery business, Cleaner Options, provided a service that benefitted dry cleaning businesses as well as customers, as he would take care of transportation between the two.
“Through the genesis of a lot of these ideas, it was ‘how do I come up with an idea that is scalable’ that will allow me to use someone else’s infrastructure to be able to deliver a product or a service to someone else and connect the two, so I can extract hopefully more than just a transaction fee,” Appelbaum said.
This paved the way for Seamless, which he founded along with his brother, Paul Appelbaum, who also went to BU and graduated in ’95, and Jason Finger, who served as the CEO of the company until it was sold to Aramark in 2006. He said Seamless began as a way to provide an intermediary position as Cleaner Options did, but ended up being very helpful to the customer.
“Ultimately, it changed the way people thought about interacting with ordering,” Appelbaum said. “The unintended beneficiary of this service was the consumer who no longer needed to repeat their order over the phone, who no longer needed to constantly re-give their credit card.”
Appelbaum has sold most of the companies he founded, and at this stage in his life has devoted his time to investing in startups. He began his investment career at AC Angel Fund, in which he learned that his past experiences prepared him for this new job.
“I felt like I was learning from being an entrepreneur what I now take away to be the most important skill in the venture capital world,” Appelbaum said. “I’m definitely not the smartest person when it comes to modeling or analyzing a business plan. I think I’m decent at that, but what I’ve gotten very good at is being able to meet somebody many times and figure out whether or not I want to get on that opportunity.”
According to Appelbaum, the characteristics he looks for when deciding investments are a willingness to learn from mistakes as well as a commitment to by-the-books business practices.
“Being able to suss out who’s going to be good at … putting themselves on the line, not worry about raising money from friends and family, being able to bet their reputation on an idea, being thick-skinned enough to fail multiple times before they succeed … are interesting characteristics that I find are often inconsistent with that textbook-perfect candidate that gets the Goldman Sachs position,” Appelbaum said.
David Ostern, a senior double-majoring in geography and philosophy, politics and law, said that he was inspired by Appelbaum’s willingness to explore different careers.
“I think what we can get out of it is that anything truly is possible, we have potential to do anything, and just because you choose one career path doesn’t mean that you can’t change it and still be successful,” Ostern said. “Utilize the experiences that you’ve had, utilize the skills and relationships that you’ve made along the way and you’re inevitably going to set yourself up for success.”