5 Rules of Hustling- Lessons from the Chicago Streets

June 22, 2014


We launched ShipBob, almost two weeks ago in Chicago downtown. Even though we had a subscriber list of around a thousand people before we launched, we decided to hit the streets( very literally!) to learn and build our startup from the ground up.  We reckoned, if we ever become big and famous, we would have grand tales to tell, and sure Chicago streets did not disappoint!.

Our company, ShipBob is the Uber for shipping. Instead of  struggling to ship your packages, finding boxes, tape, printing supplies, running to the post office etc, you let ShipBob take care of everything. We come to your location, in less than thirty minutes, collect your items, pacakge them at our warehouse and ship them out(all for  less than $5). On the backend , we compare shipping rates between different carriers and choose the cheapest ones. Think of us like Kayak for shipping along with the  added features of pick up and packaging. 

So without any further marketing plugs, here are the top five hustling lessons  we have learned so far:

1. Get used to rejections, tonnes of it

Our advisors had cautioned us. We thought we were hardened by our previous start up experiences but seeing your idea and company being rejected multiple times a day by people who are your target audience is brutual. After my first day canvassing outside the post office, I realized why consumer startups are so hard. It is extremely hard to change the way people function. We were pitching our company as a solution to people who had just stood in long lines at the post office. Yet, rejection was a default outcome. On the bright side though, the one person who says "YES" makes it all worth it!.

2. Let them incept the idea

On our second day, we started engaging with the people we met outside the post office. Instead of us directly pitching our idea, we asked them probing questions as to how much time they spent pacakging their boxes, their time spent in the post office lines , the cost of packaging , boxes etc.  We got a huge upswing of positive responses as people realised that our company's value proposition was the time we saved them and now it was easy for them to quantify and put a dollar amount to our service. 

3. Give Freebies which matter

 On our third day, we decided to set up a giveaway of free packaging boxes and tape outside the post office.  We were handing out cardboard boxes in return for people listening to our thirty second elevator pitch. While there were a lot of free loaders, we got some good feedback from this exercise. Infact, this was our must successful effort till date, as we were able to help people right when they most needed it. On the other hand, handing out free greeting cards ( around father's day), was a failure, as we got no feedback and people thought of it as yet another marketing play and refused it outright. As a result, we now have left over father's day cards which have no takers!.

4. Have a positive attitude

It is hard to be positive, when you are turned down so frequently. But positive attitude is contaigous and hard to ignore. The times, when I was laughing and smiling while talking to people, it was rather hard for them to say a no outright. A simple gesture of opening the post office doors, and wishing them a good morning has a far greater impact than you would think. Infact, as we realised it eventually, even though grinding on the streets is hard, once we started enjoying the exercise, our success ratio sky rocketed. 

5. Listen to everyone, follow your heart

When you talk to so many people, there is going to be a lot of feedback. Some days, we felt overwhelmed with the information we were receiving. Some wanted us to add this one little feature before they would use us, some wanted us to remove some piece of functionality completely. We are slowly learning to filter the real feedback from the noise but it is important to differentiate between the two. On a lighter note, we got a lot of feedback from a homeless guy who lives outside the postoffice. He told us the busy times, introduced us to the regulars and became a loud spokesperson for our app!.

We are in week three of our startup journey and loving it so far. We have found Chicago to be an incredibly supportive city to new startups and we are glad we launched here. To close off, a huge thank you to the early adopters and believers whom we met outside the post offices and who provided us with some valuable insights and feedback. You guys are the reason we keep Ship-Bobbing every day!

Image via Shutterstock