Ryan Graves' Billion Dollar Tweet

How one tweet made Ryan Graves a billionaire. "I am a great believer in luck, and I find the harder I work, the more I have of it."

In 2010 Ryan Graves was a recently-engaged Chicagoan who had spent two years at General Electric Healthcare, spending nights and weekends on a startup of his own that never quite got off the ground.

ryan graves tweet

He later spent three months as an unpaid “pseudo intern” working alongside Foursquare’s business development lead by Tristan Walker. But despite what a former colleague calls his “tireless” efforts, Foursquare declined to offer him a permanent position.

Then one day, he spotted a tweet: “Looking for a business development & product badass,” it said.

It was written by Travis Kalanick, a moderately successful entrepreneur (by Silicon Valley standards) who had recently sold his company Red Swoosh for $19 million.

“Here’s a tip,” Graves responded, tweeting back his gmail address.


Kalanick emailed Graves. The two met, decided to work together, and officially launched UberCab a few months later. Graves was CEO, a role he held for about a year as the startup took off. Graves is now SVP of Global Operations.

The end result of that tweet made Graves and Kalanick, along with a handful of Uber investors and employees, very rich. Graves currently has a net worth of around $1.6 billion.

“I found the opportunity with a little bit of luck, a little bit of right time & right place, and a lot of hard work and preparing for an unidentified opportunity,” Graves wrote on his blog.

Ryan Graves and Travis Kalanick
Ryan Graves and Travis Kalanick


Luck is real. Ryan Graves is proof. Richard Branson has 60,000 employees but recently admitted that he just learned the difference between the terms “gross profit” and “net profit.” He’s also pretty lucky. Anyone at the top of their field is a beneficiary of a significant amount of luck.

Of course, luck isn’t the only reason why some people achieve big things while others don’t. If that were true then the C-suite wouldn’t be dominated by white men. Hard work, preparation, grit, and economic and cultural factors are, for better or worse, also part of the equation.

But luck is the most interesting factor. Why is that, you ask?

Because in business, luck is a dirty word. In our capitalistic world it is us who is supposed to control our destiny. Not some fluffy, can’t-be-controlled energy that can make or break us. Chance has no place in capitalism.

Plus, luck is terribly unsexy. Powering through life and conquering the biggest challengers on earth through brute force, charm, and manipulation — that’s sexy.

“Oh – well things just fell into place and I got lucky.” That’s boring. It’s also insulting to a lot of people.

Why don’t the people in middle, those who are working to be successful, talk about luck? Because they work tirelessly, take massive career risks, and give up family time to achieve their life goal. “Hard work and grit is what will get me where I need to go,” they say. Not drawing numbers from a hat.

Luck has nothing to do with their potential success. At least that’s what they want to think.

I’ve noticed that the people who we consider successful are the ones most likely to attribute their success to luck.

Marc Andreessen, an entrepreneur, billionaire and arguably the most successful startup investor ever, said that a big, hungry market is the biggest factor in whether a startup will succeed, not a great product or a talented team.

“The product doesn’t need to be great; it just has to basically work. And the market doesn’t care how good the team is, as long as the team can produce that viable product.”

In other words, factors outside of a team’s control is the biggest factor to success. Luck.

Elon Musk would not be the Elon Musk if he were born 100 years ago. Musk’s first company, Zip2, was created as the internet started taking off. Zip2 put people’s data online, a web version of the Yellow Pages. This wasn’t possible before Zip2 existed. Businesses needed Zip2 which is why Compaq acquired it for $308m.

Zip2 gave Musk the wealth to start PayPal, and PayPal’s success gave him the wealth to start Tesla and SpaceX. While Musk is one of the most disciplined, bold, and intelligent leaders in America, none of this would have happened if he was born even just 20 years earlier. Luck, therefore, played a massive role.

In the legendary management book “Good to Great,” Jim Collins explained that the best CEO’s attribute most of their success to luck, not hard work.

“When good results happen, Level 5 Leaders credit good luck. When results are disappointing, Level 5 Leaders blame only themselves and take responsibility. Other leaders credit themselves when good results come and blame luck or other people for failures.”

The lucky divorce

In Feb of 2015, the oil billionaire Harold G. Hamm made the news because of his unique divorce from his wife. Mr. Hamm, who once had a net worth of $18 billion, refused to give his wife half of his money, arguing that his wealth came largely from forces outside his control, like global oil prices, the expertise of his deputies and other people’s technology.

Mr. Hamm’s lawyers calculated that only 5 to 10 percent of his wealth came from his own effort, skill, management or investment. The case is still ongoing, but many experts believe Mr. Hamm will win.

Harold Hamm with his now ex-wife
Harold Hamm with his now ex-wife

In another divorce case, Chicago taxi magnate David Markin claimed he was “merely a passenger on this corporate ship (that he created) traveling through the ocean,” according to the judge. Another Markin was the CEO of the company, he tried to prove that he was only a small factor in his success. The crew and ship that he helped assemble did the work, not him.

Unfortunately for Mr. Markin, the judge didn’t buy it. His wife ended up with half of his earnings.

Most people will claim their success happened because of luck if it means not giving half their net worth to someone they dislike. But I’d argue that Mr. Hamm and Mr. Markin have a point – luck did play a very important role in their lives.

Of course, these are just stories about luck. Thankfully there’s data that proves how big of a factor luck is in someone’s success (or failure).

“As we know from the research, the performance of a large firm is due primarily to things outside the control of the top executive,” said J. Scott Armstrong, a professor at the Wharton School at the University of Pennsylvania. “We call that luck. Executives freely admit this — when they encounter bad luck.”

Tha Harvard Business Review reported on a 2014 study where a team of professors analyzed more than 3,000 CEO turnovers. They found that CEOs were regularly fired for factors outside their control. Many CEOs were fired because of economic and industry factors that hurt the company. They also found that CEO’s were fired more often during recessions and downturns, which are obviously outside the control of any one person.

In other words, luck plays a massive role in both success and failure.

So what’s the point here?

The thing I want you to takeaway from my ramblings is that it’s terribly important to acknowledge the importance of luck in our lives. Luck can make or break us. It’s extremely uncomfortable to admit because it makes us feel powerless. But it’s true.

But, and this is a big but, this doesn’t mean we shouldn’t just stop trying to achieve. In fact, it means the opposite.

To quote Seneca, “Luck is what happens when preparation meets opportunity.” Acknowledging that luck plays a massive role in our outcome means we have to work are fucking asses off so we’re ready when it comes.

The twist

Before responding to Travis Kalanick’s tweet, Ryan Graves had an interesting career.

In 2008, Graves was a database administrator for GE Healthcare, a job that he said was “unglamorous” and dull. As Graves bluntly put it, “The corporate career — 20 years in the same company — was not really my thing. I can’t be the GE guy.”

So in 2009 he made a radical change. Graves applied for an internship at the Foursquare. This didn’t become a full-time job.

But that didn’t stop him from trying to prove himself. Instead of giving up he spent evenings and weekends pretending to work for Foursquare while still working for GE. He cold called bars around Chicago, explaining the benefits of Foursquare, showing business owners how the app worked, and encouraging them to sign up.

He then emailed that list of new customers to people connected with Foursquare, including investors. Graves was promptly given a full-time position doing business development.

And Graves didn’t stop there. After getting the job he began to relentlessly interact with people in the startup industry, not just at networking events, but through social media. In his words, he wanted to “put himself in the right position to meet as many frickin’ people as possible.”

That’s how he saw Travis Kalanick’s tweet. While at Foursquare, Graves heard Kalanick was tapped into the Silicon Valley and was investing in companies. Graves followed Kalanick because Graves “was watching what was going on…and was trying to put [himself] in the right position.”

When Graves told the Silicon Prairie in 2012, “Uber’s kicking ass and I’m here because I met this guy on Twitter. And he’s not the only person that I’ve met on Twitter. Like, for some reason I make a lot of things happen on Twitter.”

Luck undoubtedly plays a role in every success story, but the great humorist writer Stephen Leacock put it best: “I am a great believer in luck, and I find the harder I work, the more I have of it.”

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