From Candy Hustler to Digital Agency Owner

“The world needs that special gift that only you have.” - Marie Forleo

A couple of months ago I was asked what entrepreneurship means to me. I’ve been sitting on this for a minute, kinda bouncing the subject around in the back of my mind. I thought about how I got my start, why I chose this life, and what it has meant for me and my family.

In true Reuben style, my brief answer turned into a story. If you’re in a hurry and want to get to the quick answer, feel free to skip on down to the end.

Dipping My Toes in Entrepreneurial Waters

For me, it probably started back a little bit before middle school. I was always enterprising. From mowing lawns to shoveling driveways, delivering papers and helping out at a local horse farm, I wasn’t afraid to get my hands dirty in the work.

But, my first real taste of entrepreneurship came when I was in 7th or 8th grade. I had come up with the idea to buy candy from the local discount stores and sell it at school for a profit. I saw how much the school store was charging for candy and thought they were selling for a helluva lot more than what I could get them for at the local drug store or corner stores.

I sat down and came up with a plan, then set about working to get a few dollars to actually buy some product. If I’m remembering correctly I ended up riding down to the corner store and buying a couple dollars worth of candy that I could break apart and sell as individual units. I don’t remember everything I bought, but I do remember buying a king size pack of Reese’s Peanut Butter Cups. I remember that specifically because in time Reese’s would be my undoing.

I didn’t have access to much money, but I believed in my idea and often skipped out on lunch, using my lunch money instead as capital to help buy product.

When I went to school the next day I kept what I was doing on the down-low. I kept an eye out for the kids that I thought had some disposable income…you know ‘em when you see ‘em, so did I. I let a few kids know that I had access to candy and then told them to keep it nonchalant because I didn’t want to draw too much attention and have problems with the teachers.

Kids wanted that candy and I had that candy connect.

The candy was a hit. A serious hit. I ended up selling every piece of candy I had. Bubblicious Bubble Gum – sold by the piece. Bubble Yum – sold by the piece. All those jumbo packs were netting me some coin. I was selling each piece of gum in its individual wrapper for 25 cents. That was a great profit from my POV. I probably paid something like 50 cents per pack and there was something like 5 to 10 pieces in each, so I was feelin’ golden.

I took all the money from my first haul’s sales and put it directly into buying more product. Rinse. Repeat. It felt amazing. Kids wanted that candy and I had that candy connect. I was the only one selling the shit they wanted, the flavors they liked. I didn’t want to jeopardize anybody’s lunch or make anyone broke so my prices were extremely reasonable; after a kid bought their candy they could still buy lunch. And for me, that little bit of money was a big deal so I was happy.

Then some other kids noticed what I was doing.

I had created a little economy, but I wasn’t greedy about it so it hadn’t raised any eyebrows with the school staff. The other kids, however, came at the game from another perspective. Instead of selling candy in pieces for 25 or even 50 cents, they were selling entire king size Reese’s Peanut Butter Cup packs for $10 each.

I honestly couldn’t believe what was happening. I didn’t care so much that they were competing with me, just that they were being incredibly flagrant. I knew that kind of money was gonna set off alarms, and piss people off. And it did.

The other candy sellers had been a little too flashy with their profits and soon enough parents started calling the school. Teachers started keeping an eye out for kids who were holdin’ money or candy. And then one day I got the dreaded call to the Vice Principle’s office. A kid who had been caught selling Reese’s for $10 a pop was there too. One of his customers likely felt exploited and complained to an adult.

The VP asked about my operation and I shared it with him. I told him what I was selling and that I didn’t feel I was overcharging anybody. “When kids leave me, they still have their money. I just get a little taste.” He seemed to get that, maybe even respect it. But, with the other kids taking a different approach and selling at exorbitant rates, he had to shut us all down.

A day or so before that I had made my biggest product purchase to date and spent all my earnings on one big buy. I had gone on a long ass bike ride to a bigger candy store that had all kinds of flavors and candy options and went deep into buying all the stuff I knew my customers liked. It was gonna be magic. Until it wasn’t. And I lost everything.

What I Learned

I learned a few lessons from that experience: Entrepreneurship is freedom. You can be you. With a little smarts, some savvy, and a bit of good fortune on your side, you can find your own flow and then work within that to make magic happen.

Don’t over-invest if you can’t afford to lose it all. When I made that last fateful haul, I was looking for a big win that would help set me up for an even bigger operation. I had already been planning to create a candy store, either in the woods* or my parent’s garage, but with the quash on my territory it never panned out.

*I’m well aware (now) that no kid is gonna wanna huff it to some spot in the woods to buy candy, especially after school when their access is no longer limited. But, I wasn’t then. Suburban kids did everything in the woods back then, am I right?!

Supply and demand: Respect it. Understand it. Be smart. Keep your mouth closed. Use your senses.

Those $10 dudes killed the game for themselves and everyone else. They were greedy and it cost us all. Not only did it cost us our ability to make a little bank, it also cost their customers their lunch money. You gotta care about the people your selling to. Like Jay-Z says “Yeah, thanks to all the hustlers. And most importantly you, the customer.” If you don’t care about them, you’re lost, you just don’t know it yet. Figure out where the balances are.

Always know what your next moves look like. Have some contingencies for when shit gets really real. If something goes sideways, how are you set to handle that? Or better yet “Stay Ready, so you don’t have to ever get ready.”

Beyond The Candy Biz

Those days selling candy in school got me thinking in new directions. I never wanted to be a lifelong employee. I didn’t want the 9 to 5 life, a clock or a boss. I wanted to call my own shots. Make my own plans and do it my way.

That wasn’t my last foray into business. Sometime after that, while still a young kid, I tried my hand at a lawn mowing business. Then a bush-whacker. Neither of those had much success. I didn’t understand the various value propositions, the threshold of the market or how I would make a profit after paying expenses, all of which required upfront investment.

In my early twenties, I worked for a friend sealcoating residential and commercial lots. He had a small crew and the pay was pretty good. The goal was to become his partner. Since I was younger, strong as hell, and liked to hustle, I would do the work, he’d run the back office, and we’d both make bank. That was the plan. I had worked my way up to become lead crew person before the sky fell in.

His life hit some significant bumps and he lost his business in the process. Dreams deferred yet again.

I worked a few different jobs after that and made similar attempts to start a business of my own, most of which included labor-intensive work. But by then I’d lost most of the passion I once had for that kind of work. It was no longer something I wanted to do for any real length of time.

Ayo, did someone say technolog-ayo?

My formal education was in tech. I’d left school as a certified drafter, CAD Operator, along with a few other accomplishments, none of which had yet panned out for me. Several years after leaving school I ran into a former classmate. He had been fortunate enough to be working all that time doing CAD, but was now transitioning to the world wide web. He was off to make bank building websites and wanted to know if I’d be interested in taking over his position at a local company.

That was the impetus that got me back into the tech world. I didn’t get his old job, but I was finally able to get a CAD position at another company. More important to this story though was the exchange I’d had with my former classmate, which despite taking a CAD position, had piqued my interest in the world wide web.

At the same time, another friend had been trying unsuccessfully for years to get me into web development. I was resistant, to say the least.

But, between the two of them, and my time in drafting I was finally becoming open to exploring the web. During the day I was still doing CAD work, and at night Sherri & I would be learning everything there was to know about how websites are built.

Then, we jumped. Head first. That was 2001.

So, what does entrepreneurship mean to me?

Entrepreneurship is access; to people, experiences, and opportunities that many others aren’t fortunate enough to have proximity to.

Entrepreneurship is legacy. I’ve always wanted to leave a legacy. Something that says I did something worth doing. I’ve always seen that happening through entrepreneurship. The goal is to use what I can to empower myself, my family, and others around me, while hopefully leaving a lasting impact.

Entrepreneurship is family. My parents worked together a lot, at both day jobs as well as their own businesses. Which may in part be why I’ve always had a desire to work alongside my wife. As adults, we spend so much time working away from home, away from our families. My thinking has always been, why not do that same amount of work, but with someone you actually want to spend that much time with?

Entrepreneurship is an opportunity to inspire our hood. Our culture. Our crew. And build our tribe. Coming from a background as someone who’d aspired to be in the ministry, I’ve always been someone who loves other people. Uplifting them. Inspiring them. Being in the trenches with them. When I left the world of organized religion behind, those values were still very much intact. When Sherri and I approach the work we do today, we’re constantly thinking about the visibility we can give to people who look like us, who come from a place similar to us, and who’ve shared similar experiences. It’s a big part of why I’m so adamant about wanting to infuse our sense of culture in the work that we produce. Entrepreneurship enables that kind of visibility. It lets us help folks in ways that only we can. That’s a really poignant thing right there.

“The world needs that special gift that only you have.” - Marie Forleo

Entrepreneurship is change. It’s the opportunities I get to experience daily with my wife and best friend. It’s knowing that whatever happens, I’ve adapted up till this point…so much so that I know I can handle almost anything that comes my way.

It’s wearing baggy jeans and a fitted to close nice money contracts. It’s cultural representation that stunts with pride and respect for self.

Entrepreneurship is tenacity. It’s hard as fuck. And it’s work….work your soul raw, level work.

Entrepreneurship is pride. It’s family. It’s community. It’s life. Style. Passion. And culture.

It’s all of the above.