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March 18, 2013

How Sheldon Gilbert Became A Technology Entrepreneur

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Written by: Liane Membis


few years ago, if you owned a retail business and wanted to advertise online to your target market, you bought ads for as cheaply as possible and hoped for the best. You couldn’t use your sales data to pinpoint the users who were most likely to buy. And you couldn’t give the online publisher any additional incentive to show your ad to the most likely buyers.

Today, that old model is changing. Technology now allows retailers to make better case-by-case decisions about which potential customers they should advertise to and how much they should spend to get their message to a particular customer. Retailers buy their ads at an auction and when they encounter a customer who is likely to buy, they can bid high. The company behind this technology is Proclivity Media, run by a St. Lucian immigrant who lives in Harlem.

Sheldon Gilbert founded the company 5 years ago and is one of the black technology entrepreneurs who debunks the myth that there are no black technology entrepreneurs. Tucked away on a side street in Chelsea, Proclivity Media puts a twist on digital ad bidding by using a retailer’s e-commerce data — everything from cash price points to inventory — to best predict and match companies with ad placements that will bring them the most sales. Gilbert declined to specify his revenues, but assured me that sales for his company are strong. On a blistering cold Thursday afternoon, I sat down with him at his company’s office to discuss his unexpected, yet successful path into entrepreneurship and what he believes is the most important asset young innovators should possess.

Q: How did you get here? Did you ever think about entrepreneurship or computer science in college?

A:  At Yale, I was pre-med. I think that science is ostensibly a discipline that is designed to help you understand relationships around variables that is very similar to what I do now. I’ve always been fascinated classifying things and genomes because of their structure and processing.  In the 90s, I went and did research work for a while and then went out to Silicon Valley. I learned a lot there about e-commerce. I learned how to program and really got into data mining, particularly for retailers.

Q: So is that when you got the idea for Proclivity?

A: It was then that I realized that retailers were collecting unprecedented amounts of data but had yet to create any systems to ingest and process it. There is a typical saying that says, “Innovation doesn’t happen from within it happens from outside.” I wasn’t formally trained in computer science, so I didn’t know what rules I was breaking. However, being in that position allowed me to literally think outside of the box. I then decided years ago to build out the company because I felt that there was an untapped opportunity in the market with retailer data that could be leveraged.

Q: So you packed your bags, returned to New York, and started this company on your own?

Yep. It was just me and my bedroom. I deferred grad school in computational genomics to start the company. While I was living in Harlem, I supported myself by tutoring chemistry to kids at private schools. For a year, I basically tutored at night and during the day I’d work on the algorithm. We met a few investors and then raise capital. I also cold-called people. Everything grew from there. We’ve been in business since 2007…about five years now.

Q: And you’ve managed to expand from just yourself in your room to a company with several employees.

A: The company has evolved according to the market. We had one expression of the business when we started and then pivoted from that. I realized there was a huge opportunity about two years ago with people trying to get into online advertising; ever since then business started taking off.

Q: What would you say are your biggest challenges as an entrepreneur?

Being too far ahead of the market. I had an idea for something before it was ever even realized. It’s a dangerous thing to be ahead of the market because “the pioneers are the ones who get the arrows in their back”. But I knew at the core of what we were doing was extraordinarily valuable.

Another natural challenge is securing talent. There is an ongoing debate of whether you want to be in Silicon Valley or Silicon Alley and the thought is that the stronger engineering talent is on the west coast. We had to train a lot of engineers on some of the new constructs and getting engineering talent is a challenge for everyone here in New York City.

Q: So, during those days you never thought to yourself “what am I doing?” and wanted to quit?

A: No, I never wanted to quit. I knew it worked. I knew the business value. I had already done enough experiments with the data to see how powerful and predictive it was. And that’s why I deferred grad school because I knew I was on to something.

Q: What is your advice to young innovators, people who want to create their own businesses?

A: If you are pursuing the creation of your own company for vanity, then you will fail. You have to blindly, unapologetically be obsessed and deeply impassioned about what your doing. Because that will carry you through the troughs and valleys because you will hit them. But believe that what you’re doing makes absolute sense. You also need to understand your market dynamics. Will people really pay you for an app that will turn the light on or off? Is it a company or a feature? Is your market size 10 or 10 million people? People are not just trying to invest in a feature but a company that can scale

Q: And as people pursue building their own companies, what should be among their goals?

A: One of the things I decided when I graduated from college is that I didn’t want to pursue a particular job or career or particular salary. I actually wanted a certain state of mind. A life that involved continuous learning, intellectual engagement, travel, public speaking, teaching, the confluence of art, science and math. I wanted to create that life for myself. This company is a natural extension of that. I get to work with incredibly talented people. Its really what I’ve always dreamed of – being in a very eclectic environment. 

Corrections: This article originally incorrectly stated that Sheldon Gilbert lives in Queens and has 100 employees.

About the Author

Liane Membis


New York City Mayor Michael Bloomberg and NYPD Commissioner Ray Kelly, left to right. Photo courtesy of Flickr/Azipaybarah
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