How to Build a $100M+ Company with Optimism at it's Core - Anne Mandler
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How to Build a $100M+ Company with Optimism at it’s Core

John Jacobs

How to Build a $100M+ Company with Optimism at it’s Core


This interview is a part of ANNE Magazine’s initiative to collectively inspire, cultivate and pave a better future for the next generations of female leaders and founders. To read more interviews, please visit

Anne Mandler interviews John Jacobs, CCO of the Life Is Good Company, and talks about Life is Good and heroes of optimism for Issue No. 2 of ANNE

ANNE: Welcome everyone to ANNE Magazine. I’m thrilled and honored to have my new cohort, John Jacobs with me, he is the Chief Creative Officer, oh, Optimist. I almost had it, Optimist of …

JOHN: You nailed it …

ANNE: Of Life is Good. I’m correcting myself, and he’s joining me here at the Watermark Conference in San Jose, CA, to talk to us about his company, Life is Good. You made a clear performance/speech. I see where you did some Frisbee. John threw some Frisbees to the crowd, and I was jealous that I was sitting in a backstage room, and I couldn’t try to catch one. We’re going to talk about Life Is Good, and we know some about your story, John, how you got started with the T-shirts. You and your brother and ‘The Enterprise.’

JOHN: Yeah, The Enterprise.

ANNE: Yes, will you talk for a minute for people who aren’t familiar?

JOHN: Sure, we (John and his co-founder and brother, Bert Jacobs) were looking for a way to combine art and business. We were just getting out of college ourselves, and we saw t-shirts as an accessible way to blend the two. So we got out on the streets of Boston, where we’re from, and I would say we were wildly unsuccessful for many years, but we also bought a van which Anne referenced, called The Enterprise. We told each other we would boldly go where no T-shirt company had gone before. And, I’d say we did that but that doesn’t mean that we sold many shirts. We went up and down the East Coast, door-to-door in college dorms selling t-shirts, and the real important part of it, seriously, was how much we learned, even when we were rejected. Like, why people didn’t like the message or the graphic or the price or anything, and we just kept taking notes. That was five years of sleeping in the van and living on basically peanut butter and jelly. We had a good time, but it was discouraging at times, and there was a lot of doubt about whether this could be, actually, sustainable living. Meanwhile, in short, – there was a conversation that came up a lot about how negative the news had become, and we wondered if we could create a rallying cry for optimists. That lead to one drawing which our friends, when we got back to Boston responded to very positively, and they encouraged us to put it on a shirt. We sold our first Life is Good shirt 23 years ago. And, that one shirt, that one phrase, just changed our lives.

ANNE: What’s incredible now is thinking about 10 years back. I would see the shirts, and I would see products and smile every time I walked past them because that is just the most optimal slogan/philosophy/tagline I’d ever heard. But now you’re in airports. You guys are everywhere. What is your scope? Can you talk a little bit about growth and how you’ve grown?

JOHN: Sure, very grassroots at first. A lot of Mom and Pop stores. We learned about having sales reps and all of this by talking to people, and trial and error. Then we learned about teaming up with some larger retailers and creating our website. None of this is rocket science, rather it was just learning as we go. We don’t have a formal background in business. Bert studied Communications (that’s my brother). He’s the CEO, and I’m the Chief Creative Optimist. I studied Art and English, so we made a good combo, and we had a lot of trial and error, but really it was the power of the message that carried us through all our mistakes. People just want to rally around something positive even in the worst times.

ANNE: Do you think it would be different if it wasn’t all in the family? Do you think that you could have a different business partner?

JOHN: Definitely, and the cool thing and the really positive thing about being in business with someone that you know that well is that you don’t beat around the bush. You’re just very direct with each other. And we grew up in bunk beds. We fight, like all brothers – we still do. But it’s usually over minor details. We share the long-term vision, and that’s the important thing. Whether you’re related or friends or not, if you’re in business together, you want to be synced up on the long-term picture. Then, everything else is just sort of like playing a sport – what offense are you going to run, what play are you going to run? That’s the easy, fun part – even if you have squabbles over it. Yet, if you’re not aligned on the long-term game, you’re going to end up having really big clashes, so we challenge each other all the time, and we respect each other’s abilities. But that unity on the mission to spread the power of optimism – that’s really the foundation for everything we do.

ANNE: That’s great. I’m a complete optimist myself, and I think that’s a great way to live if that’s in you. I think the world can use a little nudging in the way that you guys do it. Tell, me, so you ever think, “Life is Bad”? Do you guys ever have a bad day at work? You guys are always happy?

JOHN: No, I think all humans have to practice optimism or you should. We recommend practicing gratitude. None of us live it 24/7. I and everyone we work with has moments of frustration. You get into petty stuff, you know. All sorts of negative things. You know, it’s a matter of how you respond and how quickly you can shift to some foundation that gets you on the right path. For us, gratitude is really central to that, and I mentioned in the talk today that the phrase “Get To”, that we learn from our customers but it’s really – you can take something to work as “I HAVE TO go to a meeting” or “I GET TO go to a meeting because I have a job”. “I HAVE TO go grocery shopping” or “I GET TO go grocery shopping”. I’ve got legs that will carry me, you know; I live in a land of abundance where this food is available. I’ve got my health. And, we’ve heard this and learned this from people who have been through the worst adversity – cancer, losing loved ones, and they come back to that foundation of being able to recognize the simple things that they are thankful for every day. Every breath of air – I don’t want to sound corny, but it’s very real to us. Especially when you hear from people who have basically been through hell and know that they’re lucky just to have a friend, to have a sandwich, to be able to walk. I mean, that’s when you recalibrate and say, “Okay, I’m not going to bitch about some little silly detail of my day”.

ANNE: Yes. 

JOHN: Or the traffic, or the weather, you know?

ANNE: Indeed. It seems like you have also done a fair amount within your company, not just organically, but with a mission to help people. You’re giving back as an organization. So, what is something that you’ve done to give back recently? Then tell me about what you expect in terms of the next five years of Life Is Good. An inspiring note – something to wrap up for people who are not here at the conference today who really want to experience a little bit of inspiration.

JOHN: Well, we think kids are the ultimate optimists. Especially young, healthy kids who view the world as wide open. They want to engage and explore. They’re curious, and unfortunately, some kids have things that happen to them that are not their fault. For example, any form of trauma, poverty, violence, illness that makes it really hard to live. Instead, they’re in fear every day, and that’s how we created the Life is Good Kids Foundation. It’s a lot to get into right now, but it’s working with child care providers who are in the trenches every day to help them to maintain their sense of joy, optimism, enthusiasm, so that they can give that to the kids every day. And, we’re now positively impacting about 120,000 kids a day through the Kids Foundation, and it’s a big reason why we exist. It’s just another way to spread the power of optimism.

And then, your last question. We see on the horizon a lot of new vehicles. T-shirts have been our thing, and then we expanded to different kinds of apparel. We see a lot more education, specific classes on optimism. Training corporations. Movies. More publications. We put out a few books around our values and our response has been great – people are hungry to find happiness, really and to enjoy the ride and to find meaning in their lives. So, we try to combine all those things into every initiative and those things like film and education. There are just other domains in which we’ve just dabbled and we – they’re a big part of our future.

ANNE: Well, thank you so much, John. This is exactly why we’re talking today, and if anyone wants to reach out, it’s

JOHN: is the place, and that’s also where there’s a lot of positive content starting to bring in stories, heroes of optimism. They’re very uplifting to share with friends, so I encourage you to come visit us.

ANNE: Excellent. Thanks so much. Life is Good.

JOHN: Thank you, Anne.

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