As entrepreneurs, there are a lot of things that we don’t know. It’s challenging to get on a pathway that you believe will bring you to the result you want. I’ll tell you a little secret, that pathway doesn’t exist. Every day you’ve got to get up and face different challenges and pressures in your life. Entrepreneurship is just a continued effort. But one thing that you can do along that path as you iterate and pivot is asking for help.
You can be curious, embrace some discomfort in not knowing the answers, and learn through trial and error. But if you want verification that you’re directionally correct or have a door opened, you have to ask for help. If you do a little bit of research, you’ll find many people out there who want to give back genuinely. Asking for help to take ownership of your career trajectory or the business you’re building is the first step to set you up towards reaching your goal. It’s what Frederick Hutson did while in prison.
Hutson was honorably discharged from the Air Force in 2005. Soon after, he turned one of his business efforts to sending marijuana through the mail. Hutson was caught and sent to prison for over four years. While there, Hutson encountered the difficulty that American inmates have with communicating with their family and friends outside of the institution. This problem sparked the entrepreneur in Hutson, and birthed his idea of Pigeonly. After hours and years of research, one of the first things he did was ask a friend for help.
When he was released to a Florida halfway house, he contacted an Air Force friend, Alfonzo Brooks. Hutson asked for a job to help him get on his feet while working on his business plan. Brooks agreed to hire him. Pigeonly went on to be accepted into Y Combinator and NewMe accelerators, raising over $6M in funding from investors. The founder of Techstars, David Cohen, even encouraged him to attend Techstars’ Patriot Boot Camp after Hutson decided to reach out on the chance that Cohen would advise. Pigeonly has successfully forwarded pieces of mail and facilitated minutes of telephone calls in the millions. Oh, and that Air Force buddy he asked for help? Brooks is now Pigeonly’s Chief Operating Officer.
Hutson would have never accomplished his goals if he never asked. Hutson once told Las Vegas Weekly, “Most people don’t think they have things available to them, so they don’t even bother knocking on the door. If you give someone an opportunity, and they feel like it’s something they can do, they go for it.”
Entrepreneurship — like life — is a moving target. At every level you get to, you’re going to see something, and it’s going to be like, “I want to get here. I want to get here. I want to get here.” Eventually, once you start to attain some of those small wins, you realize the psychology changes. You’ve got to be willing to fail. There is no clear path except the one you connect looking backward. But if you keep asking questions, you might get better results.