It turns out the key to a $100 million lifestyle brand was a mother's positive outlook on life.
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"We actually grew up in a household with a lot of dysfunction and two good parents, but they really both struggled with depression," Jacobs said on "Cavuto: Coast to Coast." "While our father had a hard time kind of ever finding peace with himself ... our mom's coping mechanisms were fantastic."
Jacobs recalled when his mother's dinner ritual where she would ask: "Tell me something good that happened today?"
"It got us focused on what's right with our lives rather than what's wrong with our lives."
Bert Jacobs and his brother John Jacobs graduated from college and "had five years of bad ideas."
But then they started hawking T-shirts in downtown Boston streets.
"We were also selling door-to-door in college dormitories up and down the East Coast," Bert Jacobs recalled.
Bert Jacobs said it was their mother's inspiring dinner routine that really took their side hustle to the next level.
"We did what you do in Boston when you're trying to figure something out," Bert Jacobs said. "We had a good, old-fashioned keg party."
Bert Jacobs said his brother John Jacobs drew a smiley face on the wall which they boiled down to be the logo of their brand Life is Good.
"Two days later, we sold 48 T-shirts in 45 minutes."
Their business exploded, and something unexpected happened along the way.
"We started to hear from people who face tremendous adversity in their lives, and they really surprised us by being the ones who embraced it the most," Bert Jacobs said.
Bert Jacobs said it was those people who inspired them to form a kids' foundation.
For every $10 they make in profit, $1 goes to help children suffering from violence, illness or trying to overcome poverty.
"I think it's a timeless idea that optimism is powerful," Bert Jacobs said.