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How Failure Can Teach You to Build a Better Business

Three mistakes business owners make, and how to avoid them.
November 07, 2014

We’ve all encountered those who think they know what’s best for us. When you’re an entrepreneur, it seems everyone has a super special gem of advice guaranteed to make your business boom. The only problem with this advice, however, is that it often comes from people who haven’t tried it.

I don’t know about you, but when I seek out advice, I’m on the hunt for wisdom shared by those who have done it—the ones who are full of experience, not hot air.

And that’s exactly what nearly 500 women entrepreneurs got at the OPEN Forum: CEO BootCamp event in Chicago on September 30—rough lessons and honest truths drawn from experience. "The Fireside Chat: Overcoming Challenges in Your Entrepreneurial Journey" session gathered the likes of four entrepreneurial thought leaders and asked them: How can failure teach you to build a better business? The lessons learned might surprise you.

1. You Don’t Have to Be Nice

Genevieve Thiers, founder of SitterCity, thought for years that she had to be nice—until she realized that being nice wasn’t doing her business any favors. Being firm, confident and decisive, said Thiers, changes women from the 16-year-old girl in the room to the leader in the room.

“You don’t have to be nice,” says Thiers. “We grow up and we’re taught to be nice girls. We’re taught that we’re supposed to sell ourselves and we get hit with a whole bunch of stuff that’s not going to help us later.” See, there’s a difference between being nice and being honest and direct (shocker, right?). Being nice is an easy trap for entrepreneurs, especially women entrepreneurs, to fall into. It’s pure bait for failure because being nice doesn’t get you the respect you need to run a business.

Honesty and directness will earn you better colleagues, better customers and better company culture—as well as pave the way for more successes than failures. Simply being nice isn’t doing you or the people you serve any favors.

2. Create a Strong Company Culture

Jessica Brondo (founder,, JJ Ramberg (host, MSNBC’s ​Your Business), and Seth Kravitz (co-founder and publisher, Technori) all agree that company culture isn’t a bandage that can be applied later. It begins with employee one and it’s a key tool to guide a company through times lean and lush alike.

At, Brondo’s team of six has implemented a 100 percent transparency policy for all of their customer service communications. That means that whether kudos or I’ll-kill-yas come across the help desk, every employee in the company sees it. This keeps successes and failures in plain sight, letting the team as a whole know where they stand with every customer, every day.

The lesson? Don’t keep your failures quiet. Parading only success gives everyone a false sense of awesome. Your business can thrive through tornadoes and downfalls if you’re honest about where improvements need to happen. Remember honesty? Yeah. Ditch nice, get honest about your room for improvement and build a company culture powered by transparency and each team member’s ownership in the company’s overall success.

3. Know Your Numbers

When’s the last time you looked at a profit and loss statement? With over one half of small businesses failing inside the ten-year mark, it might be smart to get to know your company’s numbers.

“I feel that if you’re starting a business, you should be getting excited about the finances,” says Brondo. How did she do it? Well, she picked up a copy of Starting a Business for Dummies. Once she read that cover to cover, she then sat in front of QuickBooks for days until she’d gone through all the tutorials.

How can your business succeed if you don’t know where your money is going and coming from? Anything less than a clear understanding of your company’s numbers will make failure a bigger part of your vocabulary than it needs to be.

If your numbers knowledge is lacking, step up and get the knowledge and help you need. Learn the basics so you can ask the right questions. Find your most (and least) profitable business centers, and build a relationship with a trusted team of professionals to help run your finances. You can find online bookkeeping services like Bench for about $125 per month. Successes are powered by teams built on trust and communication. Failures thrive when you allow gaps in your financial strategy.

Strong businesses are products of their nurturing, so don’t be afraid to put a little (or a lot) of tough love into your business. Exude confidence both in your personal role and as a leader, and back that strut up with hard knowledge. The more respect you give to yourself and your employees, the more resilient your company will be against the inevitable ups-and-downs of running a business.

OPEN Forum: CEO BootCamp is designed to help women entrepreneurs reach their full potential as CEOs and grow their businesses. To learn more about OPEN Forum: CEO BootCamp live events, exclusive content and online networking communities visit

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