12 “Fails” Top CEOs Overcame Before Building Their Brands

entrepreneurshipPersonal Branding

What was your biggest “fail” as a new founder or CEO, and how did you overcome it to focus on building your brand and business instead?

The following answers are provided by the Young Entrepreneur Council (YEC), an invite-only nonprofit organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, the YEC recently launched #StartupLab, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses via live video chats, an expert content library and email lessons.

1. Waiting to Get “Big Enough”

“One of my biggest failures was thinking we should wait until we were big enough before we start doing something. The analogy I use is a professional baseball pitcher waiting to throw an off-speed pitch until he’s in the major leagues. That would be ridiculous. You have to practice doing everything you plan to do once you “make it,” or else you’ll never have the necessary skills.”

Phil Frost, Main Street ROI

2. Sweating the Small Stuff

“I focused on things that didn’t matter. I stressed out about our phone system and our logo, and I ended up setting up ridiculously complicated systems. I took a step back and stripped away everything that wasn’t needed. I had to get out of my own way in order to move forward.”

Brent Beshore, AdVentures

3. Too Much Customer Trust

“I trusted my customers too much. Everybody wishes that we were in a business world where you can take everybody at their word; however, we aren’t. Now, I make sure that things are in writing, and I am very clear about expectations.”

John Hall, Calendar

4. Good Apple, Bad Taste

“We hired an incredibly talented team member and let their negative energy bring down the rest of the team because they were talented. This went on for months until we finally had to part ways. In hindsight, we should have let them go after a week.”

Ben Wagner, LifeKraze

5. Making Too Many Assumptions

“I’ve made poor assumptions in the past on go-to-market strategies. As a first-time entrepreneur who’s just getting started, you can foolishly think you’re right because an idea originated with you. Just because something is working doesn’t mean you’ve found the best way to do it. Overcoming this took seeing someone else do the same thing better, and seeing how to emulate that.”

John Berkowitz, Yodle

6. Saying “Yes” to Everything

“I was ecstatic when I closed my first client deal; unfortunately, the client wasn’t paying, but I didn’t care. A successful case study was all that mattered in my mind. But the client completely consumed our energy and attention because we said yes to every new feature they wanted. I overcame this failure in client-management by firing my client. It was the only way to focus on the big picture.”

Jay Wu, Best Drug Rehabilitation

7. Jack of All Trades, Master of None

“Early on, we took on projects that were outside of our core focus because we were afraid that other opportunities wouldn’t come along. As it turned out, some of those projects took too much time and energy away from our main business focus and set us back by months on our core goals. Once we started focusing, our business became much more successful.”

Allie Siarto, Loudpixel

8. Not Listening to Those Who’ve Come Before You

“One of the biggest mistakes I made was not putting more weight on the suggestions of experienced professionals when I asked their opinions about our website, product, price, etc.. As CEO, sometimes you try to please by taking action on everyone’s suggestions, when you should put the most weight on the suggestion from the person who failed and learned from it thousands of times.”

Derek Capo, Next Step China

9. Poor Pricing Strategy

“With a recent venture I opted for a recurring billing structure, rather than a one time fee. It turns out this particular product didn’t suit itself to that type of fee structure, so I worked the product into a new package and put a flat price on it instead. By not being afraid to change what isn’t working, the product is now much more viable and successful than it was initially.”

Sean Ogle, Location 180, LLC

10. Hiring for Sales, Not Execution

“At the beginning, my responsibilities included customer service, website content, managing relationships with our manufacturer, walking to the post office and more. I focused our hiring on senior people, as I thought we needed more big ideas. The reality is that execution is paramount as a start-up. Only when we hired a junior team member did we free up time for bigger thinking and more growth.”

Aaron Schwartz, Modify Watches

11. Getting Too Comfortable

“My biggest “fail” was getting too comfortable with my success and holding back in areas where I needed to be more aggressive. It was easy to overcome when the competitive landscape got more challenging; it forced me to step up my game and get more creative.”

Charles Gaudet, Predictable Profits

12. Putting Skills Over Fit

“We had high turnover in our first year as we struggled to find the right people. In subsequent hiring, it has been helpful to benchmark candidates’ against the qualifications of people in similar roles at organizations we respect. As we have grown from a team of 5 to a team of 13, it has also helped to analyze the culture within among our core team of leaders to identify people who will fit.”

Garrett Neiman, CollegeSpring