Fresh out of college with big dreams and a crisp business degree, Luigi landed what he thought was his golden ticket: a position at a prestigious securities firm.

He had visions of becoming the next Chris Gardner from The Pursuit of Happyness – climbing from the bottom to financial success through sheer determination. 📈

Plot twist: Luigi wasn’t Chris Gardner.

After spectacularly failing in the high-pressure world of finance, Luigi did what any rational person would do: he fled to Maui.

For two years, he traded his business suit for board shorts, swapping stock portfolios for serving plates at a beachside restaurant. While his college classmates were climbing corporate ladders and perfecting their water cooler talk, Luigi was perfecting his tan and learning that “aloha” doesn’t pay student loans.

Then came the phone call that changed everything. A friend back home was “absolutely killing it” running his own roofing company. “Dude, you should totally start your own business,” he said.

“How hard could roofing be?”

Famous last words.

Luigi returned to his home state and launched “Over Your Head Roofing” – a name that would prove more prophetic than he intended. As it turns out, “over your head” came to represent what it’s like to run a roofing company when you don’t know:

• the first thing about running a business, and
• you’ve never actually been on a roof.

Today, Luigi serves as the perfect sidekick for Justin, and it is yet to be determined if he can be a successful entrepreneur.