Matt Higgins, a prominent entrepreneur, investor, and a recurring “shark” on Shark Tank. Matt is the co-founder and CEO of RSE Ventures, a private investment firm that focuses on sports, entertainment, media and marketing, food and lifestyle and technology.   

Today we talk about how to take control of your life, and how to switch your mindset from defence to offense.

Sean Kim:  

You have a fascinating story of how you got started. Talk to us about some of the events that occurred before you decided to drop out of high school.

Matt Higgins: 

I grew up in Queens in a run-down apartment. My mother was single and had severe health issues, doing the best she could. My three brothers and I all slept on the floor on a mattress.

From the age of 10, I took on odd jobs like selling flowers door to door and selling handbags at a flea market. By 13, I got my first job at McDonald’s, and then I worked at a Deli. These were all attempts at trying to piece it together. 

By the time I was 14, I could see there was no way out of poverty on the track I was on. I began to think that if I dropped out of high school and got a high score on my GED and then SAT, I could go to college quickly.  

Guidance counsellors kept telling me I was throwing my life away to drop out when I was 16. Within 3-4 weeks, I took my GED and SATs and was in college at 16. I got a job working for a member of Congress.

That was probably the most crucial chapter of my life. That is when I did what my intuition told me, despite what everybody was saying.  

There are a lot of downsides of going through trauma, including PTSD. But one of the benefits is that it refines your pattern recognition skills when under pressure. Whenever I stretch in my life, I come back to those steps.

Sean Kim:

Tell us about becoming the press secretary for Mayor Guliani and how your career unfolded after that.

Matt Higgins:

I was 26 and still living with and caring for my mom, who was in a wheelchair.  I asked myself: “How can I take this job for a mayor who works seven days a week in a city that never sleeps?”

You don’t get to choose when your moments come. When something incredible is offered, sometimes you have to take it.   

After 9/11, I became a part of the government agency for rebuilding Manhattan. There was no playbook for what we were doing. I spent two years working with people and forging consensus on rebuilding. It was gut-wrenching. I was there within an hour of the planes striking and moved into an apartment on-site for two years.

When that project was finished, I needed a break. The Jets needed somebody who could help them build a new stadium, and they needed somebody who understood land use, government and PR. I had that background.

That was my start. You sometimes find yourself in positions when you don’t know your endpoint.  You just need to make the next best decision. 

After eight years with the Jets, I went out on my own.

Sean Kim:

You co-founded RSE with Stephen Ross, former owner of the Miami Dolphins.  What are the lessons you’ve learned from all these years of working with him?

Matt Higgins:

1. Don’t be a grasshopper.  Don’t jump from one thing to the next, finish what you started.  
2. Winners are hard to come by.  If you spot a winner, go deep.  The less you bet, the more you lose when you win.  

 It’s the difference between an offensive vs defensive mindset. 

When your back is up against the wall, fear can help. It helps you see things that you cannot see when you’re complacent. Fear is a catalyst and a good fuel, but you make much better decisions when you’re playing offence.  

Sean Kim:

What is one actionable takeaway for people aspiring to do something, whether in business or a creative field?

Matt Higgins:

Sometimes people are in a job that they don’t want to be in and are trying to look past that job. 

Make yourself indispensable at whatever you’re doing. Somebody will recognize that gleam of greatness in you and give you the next job.  

If you do that, and you’re not recognized, then don’t be afraid to quit.  Move on and believe there is greatness in you.