Success Advice
I Built Three Businesses Before I Graduated College – Here’s What I Learned

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.
Have you tried starting a business or side hustle? How has that worked out for you? Share your stories and thoughts with us below!
Entrepreneurs
The Leadership Shift Every Company Needs in 2025
Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”
While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.
Why This Gap Exists
Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.
What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.
Tools and Techniques to Bridge the Gap
Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.
1. Practice Mutual Empathy
Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.
2. Maintain Professional Boundaries
Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.
3. Follow the Golden Rule
Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.
4. Avoid Micromanagement
Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.
5. Empower Employees to Grow
Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.
6. Communicate in All Directions
Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.
7. Overcome Insecurities
Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.
8. Invest in Coaching and Mentorship
True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.
9. Eliminate Favoritism
Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.
10. Recognize Efforts Promptly
Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.
11. Conduct Thoughtful Exit Interviews
When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.
12. Provide Leadership Development
Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.
13. Adopt Soft Leadership Principles
Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.
The Bigger Picture: HR’s Role
Mercer’s global research highlights five key priorities for organizations:
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Build diverse talent pipelines
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Embrace flexible work models
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Design compelling career paths
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Simplify HR processes
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Redefine the value HR brings
The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.
Treat Employees Like Associates, Not Just Staff
When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.
Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.
Entrepreneurs
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Back in July 2017, I attended a business seminar on entrepreneurship in India. With my appetite for learning and meeting new people, I wanted to explore the latest developments in the entrepreneurial world. (more…)
Change Your Mindset
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History shows us that the greatest minds, Albert Einstein, Thomas Edison, Oprah Winfrey, Michael Jordan, Walt Disney, Stephen King, and countless others, faced failure early on. Yet, instead of seeing failure as the end, they treated it as a comma in their story, not a full stop. (more…)
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