I Pitched to the CEO of a Billion Dollar Company and This is What Happened…

Minute Read

Only those who will risk going too far can possibly find out how far one can go. – T. S. Eliot

Too many people ignore potential opportunities because the desired outcome is “unlikely”.

The guy doesn’t talk to the girl because the girl is out of his league; the art enthusiast doesn’t apply for the curator job because she doesn’t have the right college degree; the overweight computer engineer doesn’t do sit-ups because a six pack is too far away.

The list of excuses is longer than the list of possibilities - and for good reason. It’s a lot easier to come up with an excuse than it is to go out there and give life your best.

But the reality is, many of the world’s greatest accomplishments have come from situations stigmatized with the word “unlikely”.

You know the stereotypes…

Three hundred Spartans holding off the Persian army until the rest of Greece could be rallied. Christopher Columbus’ sailing across the Atlantic into the unknown. NASA finding a way to send man to the moon.

History books, Hollywood films, and family lore are all filled with stories of the “unlikely” actually happening. The greatest achievements in human history come from people willing to explore new ideas, allowing themselves to ask “what if”, and realizing that the greatest failure is never risking anything at all.

If you think about it statistically, trying low odds activities are often worthwhile. While a particular activity may only have a 5% success rate, if you try that activity once a day for a month, statistically you’ll end up succeeding!

By keeping an open eye for new ideas, and being willing to try “unlikely opportunities” when they present themselves, you may surprise yourself with how much “luck” you can end up with.

My tweet exchange with the CEO of Upwork

I just recently had an opportunity for a short, yet valuable exchange with Stephane Kasriel, the CEO of Upwork, on Twitter.

Because I run SupportNinja, I’m always trying to learn how people manage their outsourcing, and how we can further develop SupportNinja to meet the needs of businesses - from small entrepreneurs to large corporations.

One way I do this is through the use of SproutSocial - a great social media management tool that allows me to automate and integrate a variety of activities. SproutSocial allows me to find and follow people based on their interests, automate direct messages, and track my usage statistics.

With outsourcing being one of the topics I seek out and follow on Twitter, it made sense that Kasriel came up as someone worth following. So I followed him, and he followed me back!

Thanks to SproutSocial, anyone who follows me receives an automatic message asking them what services they outsource and how the results have been.

Stephane responded to my question and I took this as an opportunity to pitch him on my company! Would the CEO of Upwork hire SupportNinja to manage his projects? Probably not, but I thought I would ask anyway.

Here’s our conversation (spoiler alert, he hasn’t hired SupportNinja, yet):


It never hurts to ask

When I first saw Kasriel’s response, the thought of pitching my business to him came to mind - and I thought it was ridiculous. Why would the CEO of Upwork hire SupportNinja?

But then, I thought about it a moment longer and asked myself, “what do I have to lose?”.

Although I don’t expect Kasriel to hire SupportNinja to manage the Upwork hiring process, if he did, it would have a tremendous impact on our business. And if he doesn’t, the only cost is a couple of minutes and a few lines of text.

Are some people just lucky?

In Malcolm Gladwell’s Outliers, he proposes that “natural talent” is almost entirely a myth. What most people chalk up to “giftedness” Gladwell reveals to be the result of extended practice.

One illustration that Gladwell provides is that of professional hockey players in Canada. Are some people just more athletically talented than others? Is that why they become the best hockey players?

According to Gladwell, the majority of hockey players in Canada are born within the first three months of the year. This poses a difficult question. Are people born in January, February, and March just naturally more talented at chasing a puck around on ice skates?

Unlikely. Otherwise, a hockey enthusiast born in August has truly hit a stroke of bad luck! It doesn’t matter how hard he tries, hockey will never be in his future.

Gladwell discovers that the reason behind this mystery is due to the age cutoff for youth hockey leagues in Canada. As it turns out, you qualify for the appropriate league based on the calendar year. In other words, everyone born in 2005 plays in the same league.

This means that someone born in January, and someone born the following December competes against each other.

Although this may not make much of a difference among twenty-year-olds, this 11 month age gap is hugely significant for eight-year-olds. The kids born in January are substantially bigger than those born in December - which results in more play time, which results in more practice. This additional practice is what ultimately leads them on to be national league material.

Really, natural talent doesn’t play much of a role in successful people’s lives. It just happens that someone is in the right place, at the right time.

So, this begs the question - is success purely a result of luck?

Yes and no. It is true that particular people have advantages due to the environment they were born into (such as a January-born hockey player in Canada). However, we can always change our environment.

If an unfortunate December-born hockey player transitioned down to the US for high school, or even college, he would very likely be the best hockey player in town - resulting in more play time and practice.

By changing his environment, this young Canadian is able to pursue his passion and dominate in his environment.

If your goal is to create a massive discount retailer that sells everything under the sun, you'll probably be unlucky. Why? Because Wal-Mart already dominates this market and it would be very difficult to beat them at their own game.

However, if you decide to sell everything via an online platform (Amazon), or if you decide to sell fewer discounted items in smaller stores, at locations Wal-Mart hasn’t reached yet (Dollar General or Family Dollar), you could become very lucky.

Facebook beat out MySpace because it didn’t try to compete head-to-head. Instead, Zuckerberg focused on a platform exclusively for college students (which kept the annoying high school kids and obnoxious parents out of the picture). It wasn’t until Facebook hit critical mass among college students that it opened its doors to the rest of the world.

Yes, Candy Crush has done so well because it was invented at the right time (luck?). But that wasn’t by chance. The designers looked around and took advantage of the time and place they found themselves in.

However, every year there are more successful businesses starting up, more millionaires being made, more athletes being born.

Don't get too hung up about the opportunities you’ve missed though. It's much better to put all your attention figuring out what opportunities you can succeed at based on the time and place in which you reside. If you play your cards right, people will be calling you “lucky” in no time at all.

Three steps to creating your own luck

If you want to find yourself as lucky as Bill Gates, Kim Kardashian, or Barack Obama, stop sitting on your sofa and thinking that it will “just happen”.

Unless you decide to take the initiative and hunt out success, there is no way you'll ever wind up with a successful business, meaningful relationships, or exciting life stories.

If you want to get lucky, then get out there and make your own luck with these three steps.

1. Always remain curious. Seek out “maybe” opportunities.

Yes, timing and location plays a huge role in one’s success. And so if you aren’t lucky enough to be in the right place at the right time, you could miss out on the chance of a lifetime.

Unfortunately, you can’t know where that right place is, and what that right time happens to be.

However, there are places where luck is more likely to find you. If you find yourself in a job that you hate, doing mediocre work, no one is going to walk up to your cubicle and ask you to become vice president of the organization. You must either find motivation to do your job well and enjoy it, or it’s time to leave this company for another profession.

The best thing you can do is to look out for little opportunities that can guide your life in the right direction. Keep a constant eye out for “maybe” opportunities - things that have a minimal chance of working out, but still could.

One of these “maybe” opportunities could become your next million dollar idea.

2. Ask “why not?” and take advantage of low-risk activities.

Some activities have a high opportunity cost. To try one of these means you risk giving up a lot. For example, quitting your job or proposing to a woman are both activities that you want to put substantial thought into.

Meanwhile, activities such as applying for a new job or asking a girl for her number have very low opportunity costs. To fail at one of these causes you minimal loss - but to succeed at one of these activities could change your life.

When considering a low-risk opportunity, don't waste time trying to sell yourself on "why". Instead, ask yourself "why not". If there is no good "why not", then go out there and give it a try.

3. Learn to value practice and persistence.

Most luck is the result of extended practice. And most businesses succeed, not because of a single action, but because they have developed a consistent routine that drives them towards excellence.

Learning to be curious, try new things, and interact with the world around you helps you grow into the type of person who sees opportunities and acts on them. In short, you are practicing “being lucky”.

The only way to increase the number of free-throws you can make in basketball is to step up to the line and practice, consistently. The only way to make a living with your blog is to spend countless hours writing hundreds of blog posts. The only way to have a successful relationship is to continually communicate and learn how to care for the other person.

What could you take a chance on today?

What opportunities are sitting in front of you right now that you might be dismissing as unlikely to succeed?

Is there something you want to try, a person you want to reach out to, or a challenge you want to take on?

Find one of these possibilities that wouldn’t take more than 30 minutes to attempt, and give it a go. You might be surprised by the outcome.