Know when optimism turns into fantasy

... and beware of going after shiny objects, says Chris Shipley, co-founder of Guidewire

Chris Shipley, co-founder of Guidewire and executive producer of DEMO, has mentored thousands of startups in her 13 years running the tech conference. In this interview, Shipley shares her advice to entrepreneurs, based on the many mistakes she's observed. As an entrepreneur herself, Shipley admits that often she's better working with entrepreneurs than being one. As she describe it: "It's like a shoemaker's child that goes barefoot."

Here are her pieces of advice (paraphrased):

Focus: The way I think about it, beware of the shiny objects. When you’re company is young, everything looks like an opportunity. At times, you say you'll pursue one thing, and then switch gears and pursue another. For resource-constrained startups, that's not the way to run a business. Avoid being distracted by all of those things that are attractive around the edge. Envision the model B-9 robot in "Lost in Space," who says, "Danger Will Robinson." You have to put the blinders on. 

Be deliberate about your culture: Every company starts out with a vision. They think they’ll be X and they turn into Y. I guarantee you that in 90% of cases, they turn into Y. That’s the nature of the discovery of a new business. The thing you can set before you, however, is not where the company is going to go. But what is the culture? What are our values? How do we want to act with one another and how do we want to act with our customers? What’s the culture? The most successful ones are where the culture is deliberate. This helps drive other decisions. Be deliberate about your culture.

Have balance: We forget often that we’re human beings. We have families and our health. I had a conversation with someone, and talked about how startups make you fat. You lose track of everything. You’re at risk of losing yourself because it’s all for the benefit of the company. Find your balance. Engage your family. Entrepreneurs at times forget they’re bringing along a husband, wife, partner and children. It feels like a touchy/feely soft piece of advice, but you need to be centered and balanced. And, decisions are going to made for the right reason.

Personal setbacks? The number one thing, it’s true in my company, is losing the vision and focus. Where we’ve struggled at Guidewire, we went down an avenue to create products/services, and we weren’t able to bring it to market. What happened is, we were clear on what we needed to do and we just kept trying to achieve it and kept pushing back the end post. But at times, you lose your critical judgment. There’s a time when you have to cut your losses and reset. You have to make practical decisions. The lesson was don’t get caught up in your own optimism. There is a point when optimism turns into fantasy. You better know when that is.