I grew up poor and in a rough neighborhood in Brooklyn, New York. It might be cliché to say I had lots of friends who were either killed or in jail at some point, but it’s true. And being cliché doesn’t make it any less unfortunate.

While growing up in the ghetto was tough, and I feel incredibly lucky to have made it “out,” there were three really valuable things it taught me that have made me a better entrepreneur.

Do More With Less

After my parents separated, we were poor. I’m talking public-assistance-food-stamp-type poor. I remember being in the sixth or seventh grade and only having two pairs of jeans to wear to school. I got teased by other kids because of it.

Since there was a lack of “resources,” we (my family and I) became accustomed to doing more with less. For example, we ate bologna sandwiches for dinner and made grilled cheese sandwiches out of that nasty, thick government cheese.

Knowing how to do more with less is helpful as an entrepreneur because sometimes you just gotta squeeze every penny out of every dollar you have.

Lord knows I’ve had lots of practice doing this on my entrepreneurial journey.

Creative Hustle

Part of successfully doing more with less is learning how to hustle, and doing so very creatively. People who grow up in the ghetto are not expected to amount to much in life. There weren’t many positive role models around when I was a kid. Luckily, my mom was super-protective and “kept on me” to do the “right thing” and stay out of trouble.

Learning how to hustle is survival 101 for any kid growing up in the ghetto. This skill has served me well, and I’m extremely thankful to know how to get my hustle on.

Skate To Where The Puck Is Going To Be

“I skate to where the puck is going to be, not where it has been.” —Wayne Gretzky

You‘re probably like, “What the heck do hockey and Wayne Gretzky have to do with the ghetto and being an entrepreneur?”

I think about the myriad times in the ’80s I was at a house party in the ghetto, most likely in someone’s basement (thumping bass and sweaty walls to boot), when out of the corner of my eye I’d see an argument or suspicious behavior by a group of guys.

It wasn’t hard to guess what was going to happen next. So before the fighting (or sometimes, the shooting) would ensue, I’d vacate the scene quickly!

The ability to know what’s coming next is a great skill to have as an entrepreneur. Think Steve Jobs.

Offering a product or service that people don’t know they want yet (i.e., innovating and creating a whole new category) is hard because of the lag in  time before mass-market adoption takes hold.

Geoffrey Moore talks about this phenomenon in his book, Crossing The Chasm. This is a great curve that illustrates Geoffrey’s point about the mass-market product adoption lag:

Image source: Jeff Bussgang, Seeing Both Sides

I love the idea of creating a whole new category; it’s exactly what I’ve done with my company. Being ahead of the curve is thrilling, but it’s also challenging because the timing of mass-market consumer adoption affects cash flow in a big way. And in my case it’s taken a bit longer than expected. (I know, I know, it takes twice as long and costs twice as much. Ha!)

So, yep, growing up in the ghetto can be brutal, but it definitely has some benefits. And I feel lucky to have these ghetto-forged skills; they serve me well and will hopefully continue to do so.


This article is an excerpt from James’ book, The More You Hustle, The Luckier You Get: You CAN Be a Successful Parentpreneur. 


  • James Oliver, Jr.

    Twin dad, ParentPreneur advocate, Tech entrepreneur

    James Oliver, Jr. is Co-Founder of the world’s cutest twins, Thaddeus and Zoe. James' purpose is to inspire Parentpreneurs around the world to know they can be both a successful entrepreneur and an amazing parent. James is a self-published author of the book The More You Hustle, The Luckier You Get: You CAN Be a Successful Parentpreneur, which is available at amazon.com, and he's a tech entrepreneur at wemontage.com