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Business Advice for Optimists

bert-jacobsBefore The Life Is Good Company was a going concern, let alone a $100 million business selling positive messaging on apparel and accessories, it was two brothers—Bert and John Jacobs—peddling their artwork on T-shirts at a trade show. They had decided to wear suits to look more mature, but toward the end of that day, a customer asked what was with the suits—they didn’t seem like the kind of guys who wore them.

“We explained that we were trying to look like business owners and what he told us turned out to be the best advice anyone has ever given me,” Bert recalls. “He said, ‘All you have to do in life is know who you are and act like that.’”

Bert, now CEO (as in chief executive optimist), hasn’t worn a suit since. And in the footsteps of that helpful customer, he and his brother offer their best advice in their latest collaboration, Life Is Good: The Book/How to Live with Purpose and Enjoy the Ride. Here, Bert shares his business insights from being an entrepreneur for almost 30 years.


“I don’t know anybody who is successful and didn’t take chances. But often people don’t take chances because they’re afraid of failing. So do what we did: take failure off the table. Early on, we decided that the days we didn’t sell anything weren’t failures—they were opportunities to learn. Maybe we had the wrong colors or the wrong graphics, or maybe we were on the wrong street corner or we had bad haircuts. We learned something on those days and they became as important as the days we were selling.”



“First, it’s not easy, so there’s no point in doing it unless you really believe in your product or service. That authenticity and passion will carry you a long way. Also, you’ll work harder, so your chances of succeeding are greater.”

“Second, your prototype or business model is never going to be perfect, and if you wait until you’re 100 percent ready, you’ll never launch your business. Just go out and start selling. The work will teach you how to do it. I’m a big fan of skinning your knees.”



“The thing about optimism is that it’s of great value on your best days—and of even more value on your worst. The reason: optimists make a decision not to pour their resources into obstacles. They pour them into opportunities. So when things aren’t going well, focus on the small light rather than the overwhelming darkness. If sales are bad, don’t spend time trying to figure out what’s going on in the territories that aren’t doing well. Go to the territory where the sales rep is killing it and figure out what she is doing right. Your time is limited, so take what’s working and grow that.”



“I think the best school in the world is the streets of America. You learn every day and what you learn is of greater value than what’s taught in an academic setting because on the job the consequences are real. But if you think an M.B.A. is going to help you get ahead, go after you’ve worked at least five or 10 years in the field. The questions you ask will come from a place of experience, so you’ll get more out of the program.”



“Going into business together isn’t a great idea if you’re just trying to make a buck. You’re going to fight, and you may jeopardize your relationship. It’s only worth it if you have a long-term vision that is much bigger than you. John and I are like oil and water, and no one pushes your buttons like a sibling. But our life values are aligned, and we have zero differences when it comes to what we are trying to do with our lives. We entered the apparel business because T-shirts were a financially accessible place to put our artwork and messages. But they also enabled us to have deep relationships with our customer base and allowed us to learn what matters in their lives. Now we consider T-shirts a tool to run a communication business.”


Bert Jacobs will be a keynote speaker at the 2015 Texas Conference for Women.


► Read more from the October 2015 newsletter.

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