Rocky Roads Lead to the Land of Milk and Honey

Gerry Cameron - Aug 20, 2019
. . . when you dig deeper and read stories on successful entrepreneurs, most will say they faced many days filled with panic and many nights filled with dread.

There’s a notable photograph of Ralph Lauren with the caption “People ask how can a Jewish kid from the Bronx do preppy clothes? Does it have to do with class and money? It has to do with dreams.”

It’s a great quote, and there are hundreds of inspiration pieces out there telling you to follow your dreams and passion. But when you dig deeper and read stories on successful entrepreneurs, most will say they faced many days filled with panic and many nights filled with dread.

An article by Frederic Kerrest centers on these successful entrepreneurs who found themselves in situations where most people would have thrown in the towel and walked away. But the low points only tested their fortitude and made them more determined to push ahead and build on their experiences.

The key to success is being totally obsessed with your idea. Amy Pressman and her husband came up with an idea to build a software company to improve customer experience, to change the customer‑experience industry, using customer and employee experience from surveys, social media, and point-of-sale systems. Their first big opportunity was sitting down with Hilton, the huge multinational hospitality company started by Conrad Hilton back in 1919 that manages hotels and resorts. The timing could not have been worse when the meeting took place on September 10, 2001, the day before the 9/11 attacks. Funding was halted, but that didn’t stop Pressman because she knew they were on to something big, and their unwavering faith eventually led to Hilton giving their software program a trial. It was a start that allowed Medialla to build momentum and be the force it is today.

Facing uncertainty and feeling panic-stricken is all too common for entrepreneurs. The key is to stay focused. Ben Horowitz of LoudCloud, one of the first companies to introduce various "clouds" for enterprises and customers to fractionally rent what is needed, rarely had a restful sleep in its early days. In fact, he will tell you that for every six months of good times, he experienced seven and a half years of sheer hell. In 2001, while out of money and finding himself doing a road show to promote his company’s IPO, Horowitz was completely stressed as he watched the Nasdaq fall day after day like clockwork, and to make matters worse, the comparable companies in the industry that LoudCloud was being evaluated against were getting cut in half. And if that wasn’t enough, he gets a call from his father-in-law telling him that his wife collapsed. Horowitz wanted to return home immediately, but his wife pressed him to continue because both knew that bailing out at the time would only lead to bankruptcy. The rest of the road show was a blur. But he focused on what was important, drowning out all the unnecessary noise that had no bearing on his company’s success. In fact, during one meeting, Horowitz was so focused on his presentation that he was not aware his jacket and pants were from two different suits. LoudCloud later became Opsware. In 2007, Hewlett Packard bought Opsware for $1.65 billion in cash.

Reading about Ralph Lifshitz starting a global fashion empire by selling neckties is truly inspiring. But reading about the challenges faced by entrepreneurs like Pressman and Horowitz and more importantly how they pushed on is both educational and inspiring.