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Tag: risk

How badly do you want it?

How badly do you want it?

Entrepreneurship is sexy. Or so says the media. Peter Thiel is paying college students to drop out and go build companies. Corporate employees are being encouraged to divorce “the man” and go out on their own. We celebrate the success stories in print, TV and movies. Entrepreneurs are our heroes and celebrities (again).

Even failure is in vogue because it too leads to success. Eventually. Or so they say.

But what isn’t talked about much among the “how I did it” and “how you can do it too” is the one moment every entrepreneur gets to when they have to ask themselves: “how badly do I want it?”

There’s always the moment when you have to make the tough call. When you question whether you’re going in the right direction, whether you should move forward or walk away.

I hit it this week. When I realized that building the company I’ve been dreaming of was going to be more complex than I originally imagined. In a good way. That I wasn’t just going to offer a product but that I was going to create the content around it. It turns out that while building and creating the product, I became an expert on the how-to.

But this means that I need to raise money sooner than expected. And since I want to move forward quickly, I had to ask myself the dreaded question.

And the answer: badly enough to go back to someone I’ve had a tumultuous relationship with, yet someone who has always believed in me and ask him to be my first investor. I’m usually extremely decisive and move like lightening but this time, I paused. I wanted to be sure that opening Pandora’s box wouldn’t have negative ramifications. After all, we didn’t leave on the best of terms.

But I want “it” so I put pride aside and wrote the letter.

The ball is in Mr. X’s court. But at least I’m staying in the game.

You can go home again

You can go home again

I left Toronto for Los Angeles years ago so I wouldn’t have to wear coats or socks. Especially in the winter. I try to go back every summer to see old friends, visit my mother and remind myself what a fabulous city it is.

This year I decided to combine business with pleasure and check out the local startup scene. I was reminded of the other reasons I left. Namely that while everyone and their brother is either involved in or dreaming about a startup in LA and the San Francisco bay area, that’s not the case in Toronto. Sure, there are a few incubators and accelerators (the “fancies” of which is actually supported by government money) but overall while they’re ramping up, I don”t think entrepreneurial fever has hit yet. At least it”s not spreading that fast. And that”s the other reason I left. Because in L.A. everyone has an idea. For a book, a movie or a business. Some never go anywhere but at least the dream is there.

That”s why I chose to leave everything and everyone behind and start fresh. And pursue my dreams, crazy as they seemed. Has it been easy? No. Would I go back? Not on your life.

I miss my friends (I see fewer of them on each visit) but the ones I do see are the ones who believed. That I could. And celebrated when I did. But I don’t miss the culture. The “what makes you think you can do it?” attitude.
Being safe means that my old friends live in beautiful homes and have lovely summer cottages and a great lifestyle. But most don’t love their jobs and regret not pursuing their dreams.

And I have stayed on the road less traveled. Always looking for the next challenge. Pushing the boulder upstream.

There’s no right and wrong. It’s just not what I wanted. The safe route. And now I’m on to the next adventure. I can’t wait to see where I’m at next summer.