Garrett O’Shea | Crain's Baltimore

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Garrett O’Shea


PockitShip, an on-demand moving and delivery company, recently expanded to Baltimore after launching in Washington, D.C. in November. The PockitShip website and mobile app connects users with professional delivery drivers who can pick up and deliver just about anything.

The Mistake:

When you’re launching something like PockitShip, you never really accurately project the amount of time you’re really going to need to do something. You think everything’s going to happen quicker.

I originally had a three-month timeframe from concept, to design, to launching beta, to getting proof of concept. I was thinking we could launch a little website, get it done really quickly, and see if customers had an appetite for this. Our data said that people knew what we were offering — an on-demand delivery service — and that people would want it.

But, you have to test it. Original testing didn’t end up taking three months, it ended up taking six months. It didn’t take the budget we set aside, it took double that. We didn’t want customers to have to give us weights or dimensions for their items, so we had to find ways to circumvent that to make it super easy for people.

We had to build a database that basically said 95 percent of items we’re going to move — furniture, appliances, etc. — weigh X and can be carried by Y. And once you start going through the list of how many items are out there and putting it in your database, you realize there’s so much — it’s almost infinite. But, we wanted to make it simple so we could tell customers, “You don’t need the weight, you don’t need the dimensions. What you do need to know is that a small item can be carried by one person, and a large item can be carried by two.”

Figuring all that out took a lot of time. There’s an old saying, “I would have written you a shorter note, had I had the time.” It does take so much time to make things simple.

Budget twice as much, and assume it will take twice as long.

The Lesson:

That was definitely a lesson learned for us — to make it simple took twice as long.

I always tell people, “Budget twice as much, and assume it will take twice as long.” That rule is always in place, but you forget to follow it yourself sometimes.

Because we were pushed back, it cost us more money. At the beginning we were self-funding, so it hurts your wallet. Taking twice as long is definitely a drain on resources.

Everything we do now, we get a lot more information up front. Luckily, now we have a six-person staff so we can delegate responsibilities. It’s better to have a dedicated team so you can delegate things out, and they’re committed to the mission. When we started, we outsourced to a lot of consultants. It’s a little harder to work with consultants, because they’re on the clock, and they’ve got time limits themselves.

Time is the most precious thing that we have. You have to be able to really budget it better.

Now when we take a look at projects, whether it’s a new app release or launching a new market, we really make sure that we have a solid blueprint. You’re never going to get it right, but we have a much better plan before we go into anything new.

Garrett O'Shea is on Twitter at @garrettoshea and PockitShip is at @PockitShip.

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