My first experience with entrepreneurship involved dumpster diving. I was 10 years old and wanted to make some money. There was a warehouse that manufactured stickers close to where we lived, so what did I do? I hopped the fence and dove into the dumpster after the sheets of reject stickers that were smudged or uneven. These were skate and surf stickers with big name brands like T&C (Town & Country) and Vuarnet. I sold them for 25 cents a pop.
My classmates put them on their book covers, Trapper Keepers, and lockers. I used the profits to buy a bike (which, in hindsight, was definitely stolen) and start a paper route. At that point, I was flying. I never realized you could just do something and make money. My eyes were wide open, and by the time I finished college, I had started three businesses.
I want to briefly share a few nuggets about starting these three businesses. I’ll also detail the skills that served me well, what I wish I’d paid attention to back then, and some steps my fellow entrepreneurs can take to prepare themselves as they pursue their ambitions. My hope is that if you’re starting a business (or want to start one), you’ll learn something from my story.
How one business opportunity led to another
At age 13, I started working as a DJ and did that until I was 22. Using money from my sticker sales and paper route, my buddy and I bought some records and rented the tables from a guy named Dom-Unique. That first day spinning in the garage, we were both hooked.
Cesar, the guy who owned Funky Town Records (where we bought records) saw our ambition and took us on as his apprentices. We learned about DJing from watching him spin. When I went to Boston College, I was spinning at top nightclubs in Boston six days a week. My second business came from promoting the nightclubs where I was spinning.
How did I promote these nightclubs? AOL chat rooms, baby! I developed a reputation amongst the club owners as a guy who was blowing the numbers out, so one of the owners asked if I would build a website and chat room for his club. I taught myself HTML in a weekend and started FunkyWeb, which I sold in 1998 for a stock-only deal and with no help from lawyers. As a result, I made zero money. The lesson: use lawyers when selling a business!
The third business came from the second. I was approached to sell golf clubs online. We secured a sick domain, built the website, and launched it. In 2000, I helped sell the business using an iBank—and this time, we used lawyers to help! But then the tech bubble burst, and just like with FunkyWeb, the millions on paper didn’t translate to hard cash.
The skills that benefited me the most
As I reflect back on building these three businesses, several skills proved invaluable along the way. The first one is what professionals call “resourcefulness.” I called it “down to get dirty.” I was literally willing to dumpster dive to make money. I wasn’t afraid to roll up my sleeves and solve problems as I went. It’s the cart before the horse, no doubt, but it worked for me.
Something we’ll discuss later that served me well was getting into a flow state. Before each set, I had a ritual that would trigger flow state, which to me meant a deep state of concentration. I also used this ritual with homework and times when I’d sit down to work on my business. Being in a flow state is what allowed me to do so many things in parallel.
I also learned to spot and make what I would call “adjacent moves.” I went from DJing house parties to DJing school parties to DJing nightclubs. Same product, three different markets. After DJing for nightclubs, I started building websites for those clubs to promote them. Same customer base, new product. Then I moved from building websites for nightclubs to building a website for a golf company. Here again we have the same product, different market.
“If you’re the type of person who has to fulfill your dreams, you’ve gotta be resourceful to make sure you can do it.” – Vin Diesel
The one skill I wish I’d had back then
As I think about my life now and the work I do, one important skill I wish I’d had as I was coming up through college was vision. Here’s what I mean by that: while I was DJing and building websites, I never put the two together. I couldn’t see the connection between what was happening online—Naptser was about to launch—and how it would impact DJs.
The reason I retired from DJing was because I saw no future in it. Had I seen what was coming, I could’ve combined my skills as a DJ and website developer to become a producer twenty years before I actually became one. Producing my own music, or remixing other people’s music, was sitting right there under my nose and I didn’t see it, so I retired instead.
Vision is a crucial skill for an entrepreneur. You can get by in the short-term if you’re resourceful and willing to hustle, but at some point you’re going to have to pivot. If you haven’t been reading the landscape as you go, you might not have anything to pivot to when that time comes.
How you can prepare for this journey
If you’re an entrepreneur yourself or you have aspirations of being one, I hope my story and the lesson I learned inspired you. As we close this article, I want to leave you with three steps you can take to set yourself up for success.
There’s a tremendous amount of advice out there that detail tactics for starting a business, and great resources like Porter’s Five Forces and a SWOT analysis. You should absolutely dig into those, but that’s not where I’d start my journey.
Success with entrepreneurship begins with preparing yourself internally. You want to become the type of person who is capable of building a business before you go out and do it.
With that in mind, here are three steps I’d recommend:
1. Remove your ego from the equation
Your ego is selfish and gives terrible advice. As you begin to observe its running commentary, you can separate yourself from it and avoid making decisions from the ego. Trust your soul instead. You’ll make mistakes, it’s true. But you’ll be capable of rebounding quickly.
“Receive without pride, let go without attachment.” – Marcus Aurelius
2. Manage your energy effectively
When you “recharge” your batteries, you’re actually just restoring the natural energy in your body because, as the first law of thermodynamics tells us, energy cannot be created nor destroyed.
How do we restore our energy? Through proper sleep and regular meditation. You should also hoard energy by preventing energy leaks. When your energy levels are where they should be, time becomes less of a constraint because you’re so effective.
3. Become adept at getting into a flow state
In that state of deep concentration, you’re able to accomplish far more than you otherwise would. Find what triggers flow for you, master that ritual, and use it often.
