Sometimes When You Lose, You Win

Life is a funny thing sometimes.

One second things seem to not be going your way. Then mysteriously, the entire universe conspires with you and a previously $h!tty situation turns out in your favor.

This happened to me so many times on my WeMontage journey. Like the time I was in the accelerator and pitching an investor who told me there is no way he would invest in my business, but then ended up doing just that thru an angel group to which he’s connected.

Or this past year when two huge PR opportunities kept getting severely pushed back when I really needed them to happen immediately to help cash flow. In the end, the PR spots hit in the fourth quarter of 2014, when consumers were more likely to buy.

That worked out great.


Another Entrepreneur Weighs In

I wanted to see if other entrepreneurs had similar experiences, so I reached out to Dino Dogan, founder of Triberr, a platform that helps bloggers solve the problem of  writing blog posts that no one reads; it does so by helping bloggers develop a community of sharing and support with other bloggers.

Below is Dino’s story about making vodka-mint lemonade out of lemons:


Imagine having thousands of people tweet you, Skype you, email you, call you, just to tell you that your company is closed down.

What happened?

I forgot to renew

It was probably the stupidest, scariest, most embarrassing thing I’ve ever done…or didn’t do, in this case.

I thought was set to auto-renew but that simply wasn’t the case. The domain expired and luckily there is a grace period which allows you to buy your domain name back. We did, but not before thousands of people got to see a bunch of ugly ads where our homepage used to be.

Things looked bleak that day. But we sent out a newsletter to all our users, published a blog post about it, and instead of a huge backlash, we got a huge show of support from our users. Comments ranged from “this only proves you’re human,” to “thanks for reminding me to check my renewal settings.”

We got a write-up on Yahoo because of it, and almost 2 years later, it’s a kind of cool story to tell. Funny in retrospect, I suppose.


I cringed when I read this story because the thought of losing is horrible. What if someone used a expired domain software to find it and buy it off? I cannot fathom the entire scenario, let alone go through a similar tribulation in life! But, despite the drama of his expired domain, Dino was proactive about letting users know what happened, which is always a smart thing to do.

And he got a feature in Yahoo! Seriously? I can only imagine the amount of increased visibility that gave Dino and Triberr.

The moral of the story is, sometimes when we think things are not going our way and we are “losing,” we need to stay patient because those bitter lemons could turn into a refreshing, tall glass of vodka-mint lemonade!


[Tweet “Sometimes When You Lose, You Win-Thoughts from @dinodogan | #entrepreneur “]


Photo Credit: Feature Image –  Kreg Steppe Winner


  1. Great perspective. I completely agree with you. In life, people often put their head down to fast and give up when they think everyting is going wrong, but in reality if we keep a optimistic look on the situation, we can turn a lost to a win. I enjoyed your article and the piece you have shared on Dino’s story about

  2. This is so true but usually only a lesson learned once you’ve experienced a heart-wretching “loss.” When I was fired from a job I loved (it was the owners I hated!) I was devastated. Turns out, it was the best thing to happen since I opened my own business and was more successful because of it.

  3. Wow I love that triberr shared that story! And I Loved what they did with it. I think people can understand mistakes and even appreciate the humanity behind them.
    And yes, so many stepping stones and lemons but I believe with something really good that you believe in? You can make mountains worth of lemonade!

  4. James I’ve had similar incidents throughout my career and the building of a business. I’ve learned that everything is part of the journey and because I don’t know how it fits…I just say thank you and keep moving forward.

Comments are closed.