Episode 36 | How Optimism Turned $200 Into $100 Million

with Life is Good Chief Optimist Bert Jacobs

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Bert Jacobs, Life is Good Chief Executive Optimist

Life isn’t easy. Life isn’t perfect. But life is good.

That’s the motto that has propelled Life is Good – the lifestyle clothing brand that celebrates optimism – from a $200 initial investment in 1989 to a $100M company today.

This week, our Awesome Office guest is none other than Life is Good co-founder and Chief Executive Optimist Bert Jacobs. In the interview, Bert shares how he and his co-founder/brother John conceived of the company, and why placing optimism at the core of the brand has helped it reach millions of people.

As Bert tells it, before it was ever a company or a t-shirt, “Life is Good” was a spirit personified by Bert and John’s mother, Joan, an eternal optimist who taught her children to turn the music up, enjoy the moment, and always remember to focus on the good things in life.

Ultimately, the pair took her message to heart, and made the spread of positive energy their lives work. In addition to the brand’s uplifting message, Life is Good achieves spreads good vibes by donating 10% of net profits to the Life is Good Kids Foundation, and by holding events like the Life is Good music festival, which is set to return to Austin, TX in June of next year.

Bert was an incredibly honest, good-natured, and fascinating guest. He told us why he believes our disposition determines our happiness, why employee engagement is so important to his organization, why work/life is balance is an inherently flawed concept, and why the people who have the hardest row to hoe tend to gravitate toward the Life is Good brand the most.

Speaking to Bert put us in a great mood and taught us a lot about leadership and business, and we think listening to him will have the same effect.  

Key Takeaways

  • Bert shares the origin of the company’s motto, and why “life is good” isn’t simply an appeal for blind cheerfulness.  
  • Bert explains why optimism is like shooting foul shots (hint: it involves hanging out with American Ninja Warriors).
  • Bert describes the early influence of his mother on his and John’s outlook, and how her spirit inspired the philosophy that eventually became the Life is Good brand.
  • Bert relays a seeming paradox about the LIG brand – that the people who have the hardest road in life tend to resonate with the brand the most – and why he thinks that’s the case.
  • Bert explains why our disposition determines our happiness, not the other way around.
  • Bert demonstrates why work/life balance is a flawed concept, and makes a case for bringing what you love the most into the office with you everyday.
  • Bert posits that companies don’t have a responsibility to help employees find their purpose (or to be purpose-driven at all), but instead makes a business case for it.
  • Bert talks about why so many companies are scared to have fun, and why they should consider integrating more fun into their business.
  • Bert explains why a company’s growth is limited by its leader’s ability to get out of the way, and explains why leadership is more successful when they act more like grandparents than parents.
  • Bert describes how, in his view, organizations and businesses have a “natural rhythm,” and what happens when businesses fall out of rhythm. 

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