Washington, DC startup PockitShip helps you move that heavy thing you just sold on Craigslist

By Tina Irgang

Getting Started

You’ve finally put your old exercise bike on Craigslist, and someone actually wants to buy it. How do you get the thing out of your house? The buyer doesn’t have a pickup truck, and neither do you. Renting a U-Haul seems excessive. So what do you do?

That’s exactly the situation Garrett O’Shea found himself in about three years ago. “The guy came to my house to get it,” he says. “It took half an hour getting it out of the basement, and we ended up taking the thing apart. I gave him bungee cords to keep his hatchback shut. I just prayed the thing wasn’t going to fall out of his trunk. It was just a terrible experience, but there really wasn’t any other way to move it.”


PockitShip co-founders Garrett O’Shea (left) and Steve Senkus

A few days later, O’Shea ended up talking to a neighbor, Steve Senkus, at a barbeque. “He had been in logistics for 20 years, and we were talking about this idea he had of creating an on-demand delivery service for big, heavy stuff,” O’Shea recalls. “He said, I don’t know anything about consumer-to-consumer plays, or how to market to people about this idea, but I think there’s something good here.”

Still remembering his recent Craigslist experience, O’Shea agreed. And as luck would have it, he had the skills to help with the marketing angle. At the time, O’Shea was a principal at RedPeg Marketing in Alexandria, VA, working with brands such as Enterprise, Geico and Anheuser-Busch.

Together, Senkus and O’Shea decided to take the leap, and PockitShip was born.

(Wondering about the company’s name? “I came up with the name sitting at my dining-room table with my wife,” says O’Shea. A branding company had supplied several names, but O’Shea and Senkus weren’t crazy about any of them. “In the end, I said, where’s your phone? In your pocket. What do we do? Ship.” The unusual spelling of “pocket” came about because the URL pocketship.com was already taken at the time of the company’s founding.)

How it works

Most startups like to think of themselves as “the Uber of …” But in PockitShip’s case, that description is more apt than usual.


The PockitShip app prompts customers to supply a few simple pieces of information about their move.

The company uses a network of contracted drivers to go to customers’ houses and move their heavy items. The contractors are mostly small, mom-and-pop moving operations.

“We’re giving them business that they wouldn’t have had on their own,” says O’Shea. “They’ve got one or two trucks, and they’re struggling to market themselves. They just want the work.” On average, he says, PockitShip drivers have seen their overall business increase by about 15 percent.

Much like Uber drivers, the company’s independent contractors — numbering between 30 and 35, O’Shea estimates — can still work at any other job, and pick up PockitShip moving jobs on a first-come-first-served basis if they happen to be in the area where the move is set to take place.

It’s a point of pride for O’Shea that 95 percent of the drivers who signed on with PockitShip on day one are still part of the company’s network.

Another similarity with the Uber model: Each customer’s move is coordinated through PockitShip’s apps. There’s an app for the customer and one for the driver, both of which are available in iOS and Android formats.

Making the move easy

For customers, putting in an order is relatively easy, says O’Shea. As long as the move takes place within PockitShip’s service area — which currently includes the Washington, DC and Baltimore metro areas — there is a flat fee for each item. For items up to 250 pounds, pickup from an outside location is $99, and pickup from an inside location is $139, according to PockitShip’s website. For an extra fee, the drivers will assemble or disassemble items, or dispose of them at a landfill. PockitShip will also move items to a different floor within the same home.

“People just put how many items, take a picture, tell us where it’s located, and we give that information to our drivers,” says O’Shea. “The drivers see that automatically on their app. … They go and deliver it in the window the customer has requested.” PockitShip can even accommodate same-day service if there’s an available driver nearby at the time the order comes in.

At the end of the move, customers receive a survey asking them to rate their experience with everything from the app’s interface to the driver’s service. PockitShip uses the Net Promoter Score model, which rates how loyal a company’s customers are, on a scale from -100 to +100. “Right now, we have a +78,” says O’Shea. “If you look it up online, that’s the top 1 percent of all companies.”


PockitShip’s office in Falls Church, VA

The Uber comparison begs another question: How does PockitShip make sure its drivers are thoroughly vetted? “It’s actually harder to drive for PockitShip than it is for some of these ride-share companies,” says O’Shea. “Once you cross the threshold and go into someone’s home, it’s a different game. So we background-screen them, and we make sure they’re held to our list of criteria and our expectations. They are all under contract to meet those expectations.”

PockitShip makes sure every driver’s insurance is up to date. The company also expects drivers to take pictures if any problems occur on a job, and to involve customer-service reps back at PockitShip’s office in Falls Church, VA.

How to start a business

Of course, like any startup, PockitShip was a little rough around the edges at first. At first, the company incubated inside the offices of NonstopDelivery, another shipping business Senkus owned, in Chantilly, VA.

“I just had a desk in the corner and started googling ‘how to start a business,’” says O’Shea. He educated himself on the Craigslist market and the moving business, and hired a part-time programmer to start working on the app.

“We then sent out an email blast to friends and family — hey, would anybody like to move anything? We’ll do it for cheap. Lo and behold, a day later our first order came in.”

The idea was to use NonstopDelivery trucks for PockitShip business at first, but it turned out that all the trucks were busy on existing jobs, so O’Shea had to rent a U-Haul and do the first job himself, along with his part-time programmer.

“It was good, because you’ve got to know what it’s like to meet a customer face to face,” says O’Shea. “I did that about a dozen times until we finally had a driver who was dedicated to us.”

Moving into new cities

In PockitShip’s first year, O’Shea and Senkus managed to raise $1 million in seed funding, which allowed them to do a beta test, build a website and generally prove out the model.


Five-star Yelp reviews serve as inspiration on the walls of PockitShip’s office

About a year later, the co-founders raised another $700,000, which helped them fully build out their driver and customer apps.

Once the apps were rolled out, business rolled in. In 2016, PockitShip completed more than 1,100 orders, and business is already up 125 percent year over year. In addition to Senkus and O’Shea, PockitShip has five full-time employees dedicated to operations, quality control, design, marketing, social media and customer service.

The company started in the DC area, but expanded to Baltimore March 13. Over the next 18 months, O’Shea has plans to move into Philadelphia, Atlanta, Boston, Chicago and New York.

“Every three to four months, we’d like to launch a new market,” says O’Shea. “Our goal is to build a consistent brand that people can rely on wherever they are.”

Getting Started tells the stories of companies with less than five years in business. To be considered for Getting Started, email tina@smartceo.com.