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Tag: Entrepreneurship

Female CEOs

Female CEOs

On the one hand, I was thrilled to read that GM named a new CEO who is female. The other part of me looks forward to the day when that becomes the norm. When “female” or “girl” or “woman” aren’t the biggest part of the story.

Here are just a few of the headlines:

A woman can dream can’t she?

Eye on the Prize

Eye on the Prize

I’ve been very focused on staying focused. Work. Work. Work. Keep your eye on the prize. Raise money to get to the next milestone.

I’ve limited my lunches and dinners to include only work related meetings (boring I know) but necessary for now.

An old friend who I rarely hear from started contacting me on LinkedIn. She launched a new company and wanted to get together and catch up. I put her off. After all we hadn’t talked for 3 years. And I was “busy.”

But she persisted and I relented. I agreed to meet her for lunch near my office.
It was great to see her and made me realize that being too focused isn’t always best. I loved the idea behind her new company. And when I told her about StashWall, her eyes lit up. She loved everything about it. So much so that she offered to invest.

Why yes, I’ll have a slice of humble pie with that.

Slow and Steady

Slow and Steady

I’ve been living inside my own head a lot this year. Thinking and plotting. Trying to figure out how to turn an idea into a company. Sure, I built a product and have the people in place to go forward but I want to do it right. Now, I’m aware that speed is important in startups as is being first. But I also know from experience that you want to get it right. It’s true that you only get one chance to make a great impression. This whole build it, see what happens and if it doesn’t work, pivot (my least favorite word), may work if you’re a young, first time entrepreneur but it doesn’t work for me.

When I build something, I want it to work. To grow. To succeed. And to do that, especially if it’s something new. An idea that goes against conventional thinking, well, you need to take time to figure out the how.

How will you break through the noise? How will you not only get attention but also create habits? How will you make money? How will you attract smart folks to your team? And how will you do all of that without giving up control because you’re constantly giving away pieces of your company to investors?

And so, I started looking at doing things differently. The idea is exactly the same. It just takes a different journey. Instead of going straight to consumers (expensive given escalating user acquisition costs), I’m creating corporate and strategic partnerships. A win-win.

Sometimes, slowing down can get you there. Just not at the same speed. But then again, this is a marathon. And what matters is getting to the finish line.

Fitting in

I’ve been to over 2 dozen tech conferences and countless meetups since I’ve been on this journey. Not being a geek means that I’m in the minority wherever I go. Being a woman over 40 makes me stand out. Especially if I’m wearing a dress. I’ve often been mistaken for a VC.

While planning for my latest trip to the bay area, I read about a conference that had 2 speakers I’d never seen live – Steve Blank and Mitch Kapor. I immediately signed up not paying attention to the other details.

I arrived at the Orrick building in San Francisco bright and early and saw a table in the lobby with a “Black Founders” sign. Oops, there’s a detail I missed. I hoped I was in the right place. Turns out I was and they couldn’t have been nicer. Even though I stuck out among the crowd.

It was sometimes hard to relate to the speakers who talked about what it was like to be a visible minority. They weren’t complaining, just relating their personal experiences.

As a woman, I’ve never thought of myself as a minority. Maybe because I’m used to being the only woman senior executive in boardrooms full of men. Whether in the beer industry, hotel business or even in Hollywood. I never let it get in the way. I always hoped I’d be judged on my performance and results.

They say that the stats for women in tech are low. We all know about the superstars – Marissa, Sheryl, Meg but where are the founders of billion dollar companies? Well, they’re just not here. Yet.

In the meantime, we have some women running cool startups: Leah Busque at Taskrabbit, Gina Bianchini at Mightybell, Alexa Andrzejewski of Foodspotting, among others. Time will tell as to how big these companies will get. But it’s great to see more women jumping in and creating companies.

I don’t believe that your gender, skin color or age should matter, but let’s face it; investors (angels and VCs) are predominantly male. And they like to bet on people who look like them. There are SO many ideas out there that they have the luxury of choosing the ones that appeal to them. The famous William Goldman line: “nobody knows anything” rings as true in Silicon Valley as it does in Hollywood. It’s a crapshoot where the best you can do is make educated guesses.

So to black founders, women founders and others who don’t come with a pedigree from Stanford, Google or Facebook, just keep at it. If you have a great idea and know how to execute it (by yourself or with a great team) then focus on 2 things: get people to use your product or better yet, get them to pay for it. It turns out that traction trumps connections. Just look at Pinterest.

And stop worrying about fitting in.

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.