MONEY

Lose Better: 3 Leadership Lessons From a Total Screw-up

A serial entrepreneur lost a fundraising pitch last week, but came away with some useful management techniques.
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Last week I competed in Swim with the Sharks, a fundraising pitch contest run by the local New York Entrepreneur's Organization. Five finalists went head-to-head in front of a panel of judges and a live audience of 300 entrepreneurs, similar to the ABC hit show Shark Tank.

I had rehearsed several times and believed wholeheartedly that I had crafted the perfect pitch. Though I had recently already closed a seed round for Likeable Local, I fully expected to come to this event and win. I had worked very hard, I'm very competitive, and I simply expected to win. I always win.

Not this time. The event host, FUBU founder Daymond John, announced both a "People's Choice" winner and a "Judge's Choice" winner. I was neither. I emerged a loser--or at least I felt like it. I was devastated. I felt like I wasn't good enough, smart enough, or talented enough. I sulked for hours.

Then I realized I had lessons to learn from this experience, from losing:

Humility makes a difference.
I had gone into the event feeling too confident, perhaps even cocky, and that probably showed. The truth is, everybody loves an underdog, and nobody likes a cocky attitude. As Geoff James said here, "Humility is probably the business world's least-appreciated emotion." It's always important to be confident, but humble at the same time. It makes you more likeable and likely more successful.

Practice doesn't always make perfect.
While practice does make you better, it doesn't make you impeccable. There are no guarantees of success. I practiced more for this presentation than I've practiced for most things in my entire life--and I still didn't win. I had a strong presentation, but upon review of a video of it, I see I definitely could have been better. For instance, I could have made the presentation more about the problem my new comany is solving, and less about me.

There's success other than 'winning.'
You don't always have to win to achieve positive outcomes. A pessimist says, "I lost." An optimist says, "I didn't win, but what can I learn from this? What can I take away from this experience?" As it turns out, I landed a meeting with Daymond John, made some great new contacts, and walked away with a fine-tuned fundraising presentation. Most importanty, I learned how to lose better.

Despite my ultra-competitive nature, I learned that winning and losing isn't always so black and white. In this case, I may have been a loser, but the only thing I really lost was an unduly cocky approach.

What have you learned from losing? Tell me about it in the comments section below.

Last updated: Jun 17, 2013

DAVE KERPEN | Columnist | CEO, Likeable Media

Dave Kerpen is the CEO of Likeable Local. He is also the cofounder and chairman of Likeable Media and the New York Times bestselling author of Likeable Social Media and Likeable Business. Want to learn about how to grow your business using social media in 2 minutes? Click here.

The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.



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