This is the Leadership Journey series on the Choosing Leadership Podcast.

I believe we all have a lot to learn from each other’s stories – of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name.

In this conversation, Tom shares how he started his company while still in college and how that has been an advantage – when it comes to culture, leadership, and working remotely. He reflects about the difficult times he faced early on and the important role of transparency in organisations.  

You can find Tom at the below links

In the interview, Tom shares

  • So this has been my only real job to date. I was not one of those kids growing up that like always knew I was gonna be an entrepreneur.
  •  I always wanted to be a doctor. My grandfather’s a doctor. He’s 82 years old and still practices in his small town outside of Boston where he grew up. And I always loved science and school.
  • I went to college in Boston, at Boston College. I got there in 2009 and I was, I, pre-med major, working in the lab, getting ready to take the MCATs. All of those things you’ve gotta do to go become a doctor in the US.
  • my roommates were in the business school, and our business school had a business plan competition. You could pitch a Shark Tank style pitch in front of judges and you could win $10,000 for your business idea. And so I decided to do that competition with my friends just for fun
  •  freshman year, we submitted our first year of college, we submitted an idea to the business bank competition, and we didn’t make it past the first round. Our second year, we came back with a new idea, which ended up being the start of the idea for Jebbit, although we changed the idea a lot and we ended up winning the competition with that idea. 
  • I was mentally ready to drop outta school after that summer and go do the business full-time. And the thing that made it an easy decision for me was I talked to both my dean at my college and I talked to the dean I was gonna have at the medical. And I just asked them both for a one year leave of absence and they both said, sure 
  • My current challenge is everything around culture and communication and getting everyone internally at Jebbit g rowing in the same direction, fully in sync with each other.
  • One of the things I hear a lot from new employees when I get their feedback is they’re shocked at how transparent me and my management team are.
  • We spend a lot of time trying to get people in person and getting the right combos of people in person. So we get the whole company together twice a year now for a three day offsite. Once in January and once in July.