How a Tricky Craigslist Sale Inspired This Moving & Delivery Company

How a Tricky Craigslist Sale Inspired This Moving & Delivery Company

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It was a recumbent bicycle and a sweaty, uncomfortable Craigslist sale that made Garrett O’Shea make the move to become a small business owner.

“I took a big leap of faith to build something, and it’s going pretty well so far,” said O’Shea. O’Shea is the co-founder and Chief Marketing Officer of PockitShip, an on-demand moving and delivery company.

PockitShip aims to help people with small moves like Craigslist furniture sales or appliance deliveries and customers can schedule the move via an app.

“With PockitShip, you can get trucks and delivery service for small moves within 24 hours,” O’Shea said. “It’s similar to an Uber or a Lyft where the order comes in to our system and it’s sent out through our back end to our network of drivers. They look at what’s in the queue and take jobs on a first come, first served basis.”

O’Shea recently shared more about his experience of building a good idea into a national brand. Here’s a Q&A with the PockitShip co-founder on the company’s launch, its growth plan and how he’s been managing the business finances along the way.

From Backyard Barbecue to Budding Business

I worked for 17 years at a company called RedPeg marketing, a nationally recognized firm. I worked with lots of Fortune 500 brands on experiential marketing. My expertise is coming up with creative marketing ideas. It was a great career and I really loved what I was doing.

I had just sold one of those recumbent bicycles to a guy on Craigslist. I had the most awful experience. It was heavy. I had to get it out of my house, drag it through my garage. I brought it out to this guy’s car; he had a Subaru hatchback. We were trying to take it apart so it would fit, sweating all over the place. We ended up getting it in the back of his car, and I gave him two bungee cords because the back wouldn’t close. I remember thinking, “I hope that thing does not fall out of the car and hurt anybody!”

Fast-forward a week later. I had a barbecue with my now-business-partner Steve Senkus. He said, “Hey, I’ve got an idea! I would like to start an on-demand Uber-like moving company where people could just move stuff from Craigslist. There would be an app where you could take pictures of stuff and two guys in a truck would just show up and move it.” I said, “I could have used that a week ago!” A light bulb went on and I said, “There’s nobody out there doing that right now?” Steve’s been in the logistics business for 20 years. His other company is called NonStopDelivery. Likely, if you’ve ever ordered anything large from a big box store through their e-commerce website, his company delivered that to you. He said, “Maybe there’s a way we could build something like this, but I know nothing about marketing.” I said, “Well, I know a little about that!”

I loved the idea and I couldn’t stop thinking about it. I started doing research on it and seeing how many people were like me and could have used the service if they knew it existed. I decided to take a leap of faith and leave my cushy marketing job. That was 2.5 years ago. We just launched the PockitShip app in October and we’ve been up and running for about 1.5 years. We’ve done lots of different orders and have lots of customers. It’s been such an amazing journey. I love that I’ve had the opportunity to build a brand from the ground up.

Managing Business Finances

We self-funded to get the company to a beta and then tested it. From there, we took a few months to start pitching. We raised $1 million in our first round, a seed round, from friends and family and a couple of angel investors. Then, we did another round, which was a bridge of $700,000. Right now, we are pitching for a Series A round. This summer, we’re hoping to raise between $3 million and $5 million so we can take this blueprint that we’ve built and bring it to new markets.

The only credit we have right now is my personal AmEx. (Editor’s Note: American Express is a Nav partner, but this doesn’t result in preferential editorial treatment.) We are using that to pay all of our bills and then we pay it off every month. Probably after this next round, we will do some restructuring and look to see if we can get some credit. At the moment, we’re too early to get credit. We want to bring in some partners at the venture capital level to help us fund our expansion. Eventually, we’re going to have to bring on some debt and get money from other sources.

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Our approach to managing cash flow is that we break everything out into 90-day increments. It’s all about the burn rate. We set very strict budgets – every dollar is accounted for. We have a small amount that’s put aside in case we have an issue.

Business Challenges & Rewards

The most challenging thing is getting the word out. Forty percent of our business right now is referral. That’s the best kind of business you could have, because people are talking about it because they’re happy. At the end of the day, I need hundreds of thousands or people to know who we are to drive that awareness. It’s really education to let people know that this type of service exists.

The most rewarding thing about owning a business is when you make a customer happy and they take the time to leave you a review. It just makes me smile ear to ear because we are doing our job and taking care of our customers. I read every review that comes in and respond to it to say, “Thank you for your business.”

Business Lessons Learned

When you start something from scratch, there are tons of books and gurus and mentors. The reality is you can take all the expertise in the world and think you know where your starting off point is, but things change constantly. We thought we were going to build a business that would only service the Craigslist market. What we found out was that customers wanted a lot more. It wasn’t a mistake, but it changed the model.

I tell my team all the time, don’t just check the box to get something done, but really think about your actions. We really rushed to build our website and realized the functionality needed to be way more complex. It took a lot longer to get that done than we thought it would. We just wanted it to be really simple for our customers, but that took more work to build our algorithm.

With our branding, I always said to my team, “We need to look much bigger than we really are.” We are not building this company to be a local or regional company, but to be a national brand. To me, that was smart, because we are acting the part and building a foundation to be a bigger company.

Advice for New Entrepreneurs

Make sure you understand your marketplace. A lot of people have a lot of great ideas, but it doesn’t mean other people want your idea. Make sure you do the research before you spend a dollar, or spend that first dollar on the research to validate the marketplace.

What’s Next for PockitShip

We plan to raise additional capital so we can take the blueprint and bring it to additional cities. Right now, we’re looking at expanding up the East Coast from Philadelphia to Boston. Atlanta we think is a prime market, as well. By the end of the year, including Baltimore, we’d like to be in five to six cities.

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3 responses to “How a Tricky Craigslist Sale Inspired This Moving & Delivery Company

  1. wow! so cool idea! Its really hard to come up with good idea for sturtup or ecommerce. I know so many people that are intereted in ecommerce business, but have problem with fulfillment services. Effective and cheap delivery is so important.