Life Is Good's Bert Jacobs on Optimism The co-founder of the popular lifestyle brand shares kitchen-table wisdom, why attitude matters, and the lesson learned from his biggest mistake with customers.

Bert Jacobs is grounded in the present. "Whatever the challenges are, you've got to find ways to laugh, smile and celebrate every day," says the co-founder of Life is good, a lifestyle brand he started with his brother, John, in 1994.

Although the Boston-based company began as a t-shirt business featuring a stick-figure mascot of positivity named Jake, Life is good now extends to everything from coffee mugs to tote bags sold in more than 4,500 retailers including seven company-owned stores. Annual sales top $100 million.

And while it may come as no surprise that Jacobs is the quintessential optimist, do not mistake his positive attitude as airy fairy.

"Some people have an image of Life is good that we're eating ice cream and throwing a Frisbee around all day and everything comes easy," Bert Jacobs says. "The reality is we're competitive. The fact we're optimistic doesn't mean we don't have moments or days of doubt and fear, like anybody has."

But optimists are different in how they view those fears, as they choose to focus on the positive over the negative. Jacobs says it's what he learned while growing up in Needham, Mass., with five siblings, a dad with a low threshold for complaints, and a mom who is a "tremendous optimist."

"While there were plenty of challenges growing up, my mom focused on what was right in the world and the family," recalls Jacobs, now 47. "I remember her driving John and I to the grocery store and realizing she had no money. She turned the car around and smiled. I asked 'Why are you so happy?' She said, 'It's tough I can't get what I need, but on the other hand sometimes I like running out of money because I don't have to decide what's for dinner.' It was ridiculous and we laughed, but it was about seeing the glass half-full."

In this interview for 'Trep Talk, Bert Jacobs shares insight on what it takes to build a lasting brand, why children are his inspiration, and a kitchen-table lesson he'll never forget. Edited interview excerpts follow.

'Aha' moment: John [brother and co-founder] and I were talking about how the 6 o'clock news always tells us what's wrong with the world and rarely focuses on what's right. So we talked about creating a symbol or hero whose power was optimism. And Brian drew Jake [company's stick-figure mascot] as a result of that conversation, but at that point the 'how' in starting the business wasn't there yet.

Finding the joy in the struggle: For five-and-a-half years we were sleeping in a van selling t-shirts, but those were really good times. People make the mistake of saying that, "Life really sucked when you were sleeping in the van and now life is good." That misses the point. It's not about what you have and where you are, it's about your view and disposition.

Homegrown wisdom: At dinner every night, my mother would start by saying, "Tell me something good that happened today." It was a great life lesson – and business lesson. If you start business meetings and just open the floor, you might get bitching and moaning, but that's not solution-oriented. By starting with what's good, whatever you focus on will grow.

Putting Children First

Life is good is charged with spreading optimism, and it brings that motto to life in its philanthropic efforts for children.

"No matter what we do we're going to be focused on helping kids," says Bert Jacobs, co-founder of Life is good. "There's a unity around that [in our company]. It helps put a bounce in people's step because they've got a bigger purpose."

• Life is good festival launched in 2003, as an annual music and arts fundraising event in Boston for kids in need.

• As part of the company's nonprofit arm, Life is good Playmakersprovides play-based therapy to kids struggling with poverty, violence and illness.

• Life is good launched a customizable fundraising page this spring that makes it easier for anyone to host their own charitable event.

• To date, Life is good has raised more than $8 million for kids in need.

I'm inspired by... children. They are open-minded, the greatest optimists and they believe anything is possible. We were all that way as children and when we get older there's a tendency to lose that.

On taking risks: People talk about starting a business -- developing boards, business plans, and focus groups -- but at some point you have to just put things into action. There's no shame in trying and falling. We've accomplished a fair amount because we're willing to fall on our faces.

Biggest mistake: At first, we were only listening to customers buying our t-shirts. We made one style – a relaxed fit – and noticed college women would walk in the store and say they love the brand, but buy nothing. When I asked why, they'd say: "There's nothing flattering to my body." Seems simple, but we're not fashionistas. So we introduced fitted and semi-fitted t-shirts and brought in customers we never had. Now we speak to different audiences.

Branding tip: You can have the greatest ideas, but the smartest people in the world can't build a brand. Customers build a brand.

On finding ways to give back: Look for a cause that relates closely with your brand. If a cause is important to you but doesn't line up with your business, that's fine but you're making heavy lifting for yourself. We're always going to focus on helping kids. Our message and most of our images at Life is good are very childlike, so it's fitting.

Optimism is... powerful. If you look around and see obstacles everywhere, you'll focus on obstacles and they'll be difficult to overcome. If your disposition is to see opportunities, you'll be drawn to them. It's a self-fulfilling prophecy.

Startup tip: Your business concept should align with who you are as a person. If it doesn't, it will be hard to make it work because you won't be as passionate about it. But if it's authentically part of who you are, it will be second nature to grow the business and make it successful.