In this inaugural episode, Craig Rosenberg, co-founder and chief analyst at TOPO, switches roles with host Justin Gray, CEO of LeadMD. Craig goes in depth with Justin about his journey and how he came to be a serial entrepreneur and now host of the “How Did I Get Here?” podcast.

Meet Justin Gray

What is your role?

To answer that question succinctly, I am the CEO of LeadMD, but my role is a little more difficult to define because I really do any of the shit that anyone else doesn’t want to do, or can’t do.

What did you want to be when you grew up?

I wanted to be a journalism major for the purpose of becoming a writer.

Along the way, as you got to where you are today, what advice did you receive on how to get there?

The sound advice I got across the board was that there was a very traditional, structured path to success in some regard or another.

What was your major in college?

It was journalism for the first two years, then switched to business with a specialty in marketing.

Who or what has been the biggest influence on your career?

There’s obviously a ton of people that have been influential, but I think the biggest influence for me was becoming part of a startup when I was 26.

What advice would you give to your younger self?

I would honestly not go to work directly. I would say, take some time and try to experience some other things.

Take away quote: "I became disenfranchised with a normal path and started to take interesting approaches to creating my own business."