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Secrets of Success: Dave Kashen

There are some “rules” of business success most entrepreneurs abide by. But many also have their own “secrets”—things they do or believe that helped them achieve success. In “Secrets of Success,” a weekly interview series here at’s Small Business Forum, I ask some of today’s smartest, most innovative, most successful business owners to share their insights and success secrets with you.

Meet: Dave Kashen, the cofounder & CEO of WorkLife, an online tool that improves the efficiency and productivity of business meetings. Before starting WorkLife, Dave founded Quantum Leading, a premier leadership and culture development firm for startups. He’s coached CEOs and trained leaders at many of Silicon Valley’s fastest-growing technology companies, including Facebook, Google, Twitter, Indiegogo, Kiva and many others. Before that, Dave cofounded an online health company called Wellsphere, which grew from zero to 7 million monthly visitors.

Rieva Lesonsky: What did you want to be when you grew up?

Dave Kashen: I wanted to build a toy company. I loved toys, so I thought it would be fun to make the toys I wanted, and get to play with them all day long. I guess I had an entrepreneurial spirit even back then.

Lesonsky: Why did you start your own business?

Kashen: I have spent the last 10 years working for businesses I started. I love the idea of building something from nothing and in each case I saw a problem that I thought needed solving. In the case of WorkLife, I realized that almost everyone who works in corporate America suffers through frustrating, wasteful meetings, and was inspired to build software to transform meetings into a productive, even enjoyable use of time.

Lesonsky: Did you experience a pivotal moment on your way to success?

Kashen: My most pivotal moment was when I decided to leave the world of finance in favor of entrepreneurship. I realized that my passion was around creating something from nothing, and left an extremely high-status, high-paying job to start from zero. It was scary, but ultimately I think you have to follow your heart.

Lesonsky: What’s the best small business advice you ever gave and/or received?

Kashen: Make more [money] than you spend. Other than that, solve a real problem that matters to you. It takes so much energy and persistence to build a business that if you’re not passionate about the problem you’re solving, it will be way harder to keep going when times get tough.

Lesonsky: What’s one “best practice” more entrepreneurs should be embracing?

Kashen: Define your values early. Most entrepreneurs don’t appreciate the importance of getting the culture right from day one—and hiring for values, as much as skills and talent.

Lesonsky: Do you have a 2015 small business prediction?

Kashen: I think here will be an increase in the number of people who work in flexible arrangements rather than full-time jobs. This will be both an opportunity and a challenge.

Lesonsky: What’s your favorite book?

Kashen: The Power of One by Bryce Courtenay.

Lesonsky: Is there a quote you find particularly inspiring?

Kashen: “If you have built castles in the air, your work need not be lost; that is where they should be. Now put the foundations under them.” —Henry David Thoreau

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Rieva Lesonsky

Rieva Lesonsky is CEO of GrowBiz Media, a media and custom content company focusing on small business and entrepreneurship. Email Rieva at [email protected], follow her on Google+ and, and visit her website,, to get the scoop on business trends and sign up for Rieva’s free TrendCast reports.