The Second Answer
What happened after I asked one simple question? A documentary director's reflection on uncovering the stories entrepreneurs rarely tell.
Jace Chong
7/10/20261 min read
One month before filming, I asked Leroy a simple question.
"Was it really that smooth?"
Before that moment, Leroy and his wife had spent almost an hour enthusiastically sharing how enjoyable their business journey had been. It was inspiring—but something felt unfinished.
Leroy looked at his wife, smiled, and then turned back to me.
"You really can't fool a documentary director, can you?"
That was when the conversation changed.
He began sharing one of the darkest chapters of his entrepreneurial journey—a story that never appeared on the surface, but shaped everything that came after. Because he trusted us with that truth, we were able to capture one of the most meaningful parts of his story during filming.
As a documentary director, I'm not interested in perfectly packaged success stories. What moves me is honesty. Sometimes it's in the pauses, the eyes, or the body language that tells me there is still a story waiting to be told.
Thank you, Leroy, for trusting us enough to share what it really took to build the life you have today.
Boss Never Off Season 2 premieres tonight, and I'm excited for everyone to finally meet the people behind these businesses—not just their achievements, but the journeys that made them who they are.
I hope you'll enjoy the first episode as much as we enjoyed making it.
