• by Laurie Sullivan , Staff Writer @lauriesullivan, March 16, 2020

Freckle CEO Neil Sweeney lives by the mantra, “think it forward.” That’s how he became successful at starting several companies during his young career.

Sweeney starts, runs and sells successful startups by recognizing a deficiency in a specific type of business. When it came to offline measurement, the focus turned to how television, search, social and other media supports foot traffic into stores and physical locations.

He also founded companies like Killi, as well as advertising and mobile technology startup Juice Mobile, which he sold in March 2016 to Yellow Pages. And then there was SteamTheWorld, which he co-owned and sold in 2010.

Freckle, which provides location coordinates and data, last week announced an extended partnership with Adsquare a real-time data exchange. The company’s spatial data integrates into Adsquare’s Audience Management Platform and enables ad targeting spanning an eight-mile radius of the physical location.

Sweeney’s many endeavors show the progression of his entrepreneurial path. Data & Programmatic Insider caught up with him last week to talk about business, metrics and the best lifetime advice he received.

Data & Programmatic Insider:  As a kid, did you think you would become an entrepreneur?

Neil Sweeney:  I didn’t think I would become entrepreneur, but I showed an interest in business. I was very entrepreneurial as a kid. If I go back and think about all the little hustles I had going on, it’s easy to connect the dots. I spent a lot of time putting together businesses since I was 12.

D&P:  Would you consider yourself a forward thinker?

Sweeney:  It sounds a bit cocky to say, but I think so. I realized as I got older, we’re good at ‘the next,’ not necessarily ‘the now.’ We’re comfortable incubating new ideas and commercializing and building them. Not everyone is comfortable with staying on the edge.

D&P:  At 12, what was one of the businesses you started?

Sweeney:  I found golf balls in creeks and sold them. I set up something equivalent to a lemonade stand on the ninth hole and sold them as people came by. As a teenager, I was always doing something along those lines. At 18 and 19, I had a company that booked emerging bands at bars around the city.

D&P:  What is the best piece of advice you’ve received during your career?

Sweeney:  The best piece of advice I received in my life, never mind my career, came from my father. When I was a kid, I played a lot of sports, so early in the morning during breakfast, before anyone woke up, my dad and I would talk about business and stocks. He was involved with both. He would read the sports and stock sections of the newspaper every morning, and we would talk about it. It was during those interactions that I became very interested in business.  

One morning after reading something in the business section, he looked up at me. He basically said: ‘It takes a lot of different people to make up the world. It’s up to you to decide your placement in the world. If you don’t, the world will happily place you.’ That was probably the best piece of advice. It’s up to you to decide what you want to be. There’s nothing easy about entrepreneurship, but I don’t suffer from the challenge of being bored or not enjoying what I’m doing.