The tiny start-up challenging the big FedEx machine

Gibbon, 31, eventually put his engineering background to use to find a solution (he had previously developed the price-comparison iPhone app called ShopAround, which shut down despite having garnered a top 100 iOS App Store ranking.) Sensing capital would be easier to raise in California, Gibbon moved to San Francisco in 2012 and took a friend’s offer to work at as a software engineer. He worked there for a year before he started focusing on launching Shyp.

In 2013, he “threw together a landing page” asking potential customers what they needed to ship and played the role of courier himself in just one Zip code area of San Francisco.

“I’d collect the shipments, pack them up back in my garage and send them off. I still had to deal with the shipping piece, but now somebody was giving me money to do it.”

That formula continues to pay off, though Gibbon is no longer your pickup guy. In Shyp’s four markets (San Francisco, New York, Los Angeles and Chicago), the company has 245 employees, including couriers, packagers and warehouse technicians who are counted as W-2 employees rather than 1099 contractors. Gibbon believes full-timers, though pricier, represent businesses better than freelancers.

Shipping starts with the Shyp app, available for free on iOS and Android. Users take a photo of their items, request a pickup, and a courier arrives at a prearranged time or within 20 minutes in markets with an on-demand option. The deliverables are then scanned into Shyp’s system and brought to a local warehouse for packaging before being handed off to a carrier, such as UPS, FedEx or the U.S. Postal Service. All for $5, plus the cost of shipping.

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