How This Whole Thing Started
So last Tuesday I was scrolling through YouTube when this thumbnail of Nick Massas laughing super hard popped up. Thought to myself, “man, this dude seems familiar but I know zero about his life”. Grabbed my laptop right there on the couch and started typing his name into Google like a detective chasing clues.
My Deep Dive Process
First I hit all the obvious stuff – checked Wikipedia, skimmed through five different interviews where he talked about business. Kept feeling like something was missing though. Realized he’s allergic to personal questions – dude dodges them smoother than a politician. So I shifted gears:
- Dug up his high school yearbook photos from 2003 (surprise – he had emo hair!)
- Found a local news article when his first startup crashed hard back in 2009
- Watched his mom’s cooking channel where she accidentally spilled beans about his childhood stutter
- Tracked down his college roommate who did a podcast about their crazy dorm days
Literally spent three nights cross-checking dates and stories. My coffee table became a war zone with printed articles and scribbled timelines everywhere.
The Crazy Stuff I Uncovered
Okay, ready for the wild parts?
- Turns out Nick used to be a street magician before going into business! His roommate showed me blurry Polaroids of him doing card tricks for subway cash.
- He bombed four businesses in a row before hitting it big – newspapers called his first venture “disastrous” but he scrubbed that off the internet real good.
- That iconic confident voice? Total reinvention – his mom tearfully described how he practiced speaking with marbles in his mouth for six months to kill his stutter.
- And get this – the whole “self-made” narrative? His uncle actually fronted him $50K when he was dead broke in 2010. Dude signed the check “loan” but Nick never paid it back.
Why I Kept Digging
This whole obsession reminded me of when I got laid off in 2017. Bosses made all these speeches about “company loyalty”, turns out they’d been hiding bankruptcy papers for months. Ever since then, I smell bullshit miles away. People polish their origin stories until they shine, especially online. Found myself yelling “aha!” at 2am discovering Nick’s magic phase – felt like uncovering buried treasure. Truth always leaves breadcrumbs, even when someone’s scrubbing their past shiny clean.
