What do potato chips, nightclubs, surprise weddings, and volleyball leagues have in common? They’re all part of one entrepreneur’s wild journey through business. Sean Lippert’s story proves you don’t need a perfect plan or a business family to succeed. You just need to start.
It Started With Potato Chips
Sean’s first business happened in eighth grade. He asked his school if he could sell potato chips at lunch. They said yes. His mom helped him buy the chips, and he sold them for a dollar each.
He sold out completely. The school let him keep going after the project ended.
That’s it. No fancy business plan. No market research. Just a kid who asked a question and took action.
Here’s what matters about this story: Sean’s entire family worked as mechanical insulators. Hard, physical work. His dad, brother, and nephew all did the same trade. Nobody in his family ran a business.
You don’t need entrepreneurial parents. You just need to be willing to try things.
Book Your Strategy CallThe Phone Book Approach to Breaking In
At 16, Sean decided he wanted to be a DJ. He didn’t know how to DJ. He didn’t have equipment. He didn’t have connections.
So he opened the Yellow Pages and called the first DJ company listed: Acme DJ Service.
He said: “I wanna be a DJ.”
The owner said: “Alright. Come on in.”
That was it. No resume. No interview process. Just a direct ask.
Most people spend months researching and planning before making a single phone call. Sean just picked up the phone. Within a short time, he started his own DJ company called Executive DJs and hired his friends.
Turning Dead Nights Into Lineups
One of Sean’s best early wins came at a bar called Last Harry’s. Monday nights were dead. The bar had nothing going on.
Sean offered to DJ Monday nights. The bar said yes because they had nothing to lose.
He made special drink deals. He called all his friends. He created an atmosphere people wanted to be part of.
Soon, Monday nights had lineups of 400 people. The slowest night became one of the best nights.
This teaches you something important: find gaps where businesses are struggling and offer low-risk solutions. If it works, everyone wins.
Your Best Skill Might Not Be What You Think
Sean realized something interesting about his DJ work. He was okay at playing music, but his real talent was talking on the microphone.
He was quick, funny, and could work a crowd. Most importantly, he wasn’t afraid to embarrass himself.
This skill led to hosting hot body contests at nightclubs. Companies like Breakaway Tours noticed him and hired him to entertain spring breakers in Florida. He got paid to travel, work with MuchMusic, and hype up crowds before they went live.
He turned one skill into multiple income streams across different industries.
Your main skill might not be what you studied or what’s on your resume. Pay attention to what comes naturally and what people respond to.
The Surprise Wedding That Went Viral
Sean’s wife was stressed about wedding planning. Everyone had opinions about how it should be done. She was running her own businesses and didn’t have time for it.
So Sean planned the entire wedding in secret for one full year.
He casually asked her questions about what she’d want at a wedding. Every answer went into a detailed planner. Guest list, food, decorations, colors, venue – everything.
On their wedding day, she had no idea it was happening. He executed a complete wedding based on her preferences.
His friend filmed it. The video went on YouTube and got 100,000 views in 24 hours. Eventually millions of people watched it. NBC, CNN, CBS, Rachel Ray, and Sports Illustrated all covered the story.
This wasn’t a business move, but it shows how executing a big project with attention to detail creates something people want to share.
Not Everything Works Out
After years of coaching volleyball, Sean became head coach of the University of Windsor men’s volleyball team. He lasted two years before they fired him.
His take? “I guess you gotta win a lot to keep your job.”
The assistant coach took over and the team did really well after that.
Sean talks about this without bitterness or excuses. It didn’t work out. He moved on. The team found success with someone else.
Not every venture succeeds, even when you have experience and work hard. That’s normal. What matters is what you do next.
Taking Over Canada’s Largest Volleyball League
After coaching ended, Sean stayed connected to volleyball. The Windsor Olympic Volleyball League had been running since 1976. The teachers who founded it wanted to retire after 45+ years.
Sean reached out and said he was interested in running it. They handed it over with one condition: keep their philosophies and grow it the way they wanted.
He agreed and now runs the largest volleyball league in Canada.
This shows a different path to business ownership. Sometimes the opportunity isn’t starting something new. It’s taking over something established and keeping it going.
The Philosophy That Drives Everything
Just Do Something
Sean’s advice if you’re not sure what to do: “Just do something because it’s never gonna be what you do, but it puts you one step forward.”
Selling potato chips didn’t lead directly to running haunted houses or volleyball leagues. But each thing taught him something and opened new doors.
Action beats planning every time.
Failure Is Required
Sean is clear about this: “If you’re not failing, you’re not learning. And if you’re not learning, you’re not getting better.”
Failure isn’t something to avoid. It’s part of the process. The only rule is don’t make the same mistake twice. Learn, adjust, and try again.
Stop Overthinking
Sean calls it “paralysis by analysis.” People spend so much time researching and planning that they never actually start.
He’s from the “old way of thinking” – grab it, feel it, touch it, and go with it.
School teaches us that wrong answers lead to embarrassment. So as adults, we’re afraid to be wrong. This fear stops people from taking the risks needed to build something.
Fall in Love With the Process
This might be the most important lesson. Sean has enjoyed every venture regardless of outcome.
“Bingo caller to pumping gas to restaurants to DJing to volleyball, like it doesn’t matter.”
He loves the work itself. The problem-solving. The creativity. The experience of building something.
If you only love the outcome, you’ll quit when things get hard. If you love the process, you’ll keep going because you’re enjoying the journey.
What You Can Learn From This
You don’t need the perfect background. You don’t need a detailed business plan. You don’t need to know exactly where you’ll end up.
You need to start somewhere. Make a phone call. Ask a question. Solve a problem someone has.
You’ll fail at some things. That’s how you learn what works.
The businesses you build in 10 years probably don’t exist yet in your mind. But each thing you do today teaches you something that makes the next opportunity possible.
Stop planning. Stop researching. Pick up the phone and make something happen.
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