153: How to Survive Entrepreneurial Failure with Steve Olsher of liquor.com

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In his lifetime as an entrepreneur, Steve Olsher has crashed, burned, and reinvented himself in the face of tremendous failure. But for Olsher, there was never any other path. If you can relate, he’s got some indispensable wisdom to offer.

“I’ve been an entrepreneur pretty much since I’ve been old enough to pick up a rake and move some leaves around, or grab a shovel and do some snow-shoveling and clear some sidewalks, driveways, that sort of thing. We’re all naturally wired to excel in very specific ways, and for me, I’ve always just been wired to rub a couple of dimes together to make that quarter,” Olsher says.

Olsher has spent his entire life as an entrepreneur, and with it, he has experienced tremendous highs and lows. From opening his own non-alcoholic nightclub at the age of 19, to starting a wildly successful internet business that was slated to go public right as the dot com crash of 2000 hit; and, building a $50 million real estate development company only to lose it all again when the real estate market imploded in late 2007.

But if success is defined by how well you can bounce back from failure, Olsher is one of the most successful people on the planet. Taking the knocks in stride, and embracing the lessons they taught him, Olsher went on to pursue other entrepreneurial ventures over the next six years, before reclaiming the Liquor.com domain and bringing on talented partners to build the business from the ground up once again.

In the years since, Olsher has distilled a lifetime of experience and lessons into helping others gain clarity on how they’re naturally wired to excel and discover, share and monetize their WHAT. He is now the New York Times bestselling author of What Is Your WHAT? Discover The ONE Amazing Thing You Were Born To Do, creator of the New Media Summit and host of the popular radio show/podcast Reinvention Radio.

In this episode you will learn:

  • Hard truths you need to know when bringing on investors
  • The importance of needing good advisors and mentors you can turn to when you need it
  • When you should and shouldn’t listen to your gut as an entrepreneur
  • How to find out what your “what” is, and how to figure out what your purpose is
  • Where to find your winning business idea
  • & much more!


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