Big Swings

One of my twins, Russell, was born a risk taker. When he was a toddler, my wife Sarah and I spent a lot of time sprinting across rooms and playgrounds and driving him to the ER for stitches. When the principal of his elementary school gave an opening tour of a new school building that had just been finished, he pointed to the high fencing on a third story bridge between buildings and told the crowd that this was but one example of how they “Russell-proofed” the building for safety.

It was nerve wracking and I didn’t want him to get hurt, but I knew that I shouldn’t discourage him. I didn’t want to introduce fear where none had existed. And I didn’t want to start down a path where I stifled his curiosity or his ability to execute against his big ideas. I knew that Russell would encounter many people and institutions throughout his life that tried to dissuade him from taking a risk, and I didn’t want to be one of them.

I wanted him to be comfortable taking big swings.

We need to encourage risk-taking in our society. Risk-taking teaches us how to achieve success by working around obstacles. Risk-taking inspires us to take unthought-of approaches to solve problems. With risks of course, there also always comes failure. And that’s good, too. With every miss, there’s a learning one can take away to make their effort stronger, better, faster the next time. It’s rare a batter hits a home run their first time at bat.

As Americans, risk-taking defines us in so many ways. Our country started as a risk — as The Great Experiment in democracy and freedom — that today has grown to a world powerhouse. And it’s what helps us prosper, fix problems, create jobs and create a better world.

The American engine of innovation is directly tied to our willingness to take risks. To have a vision and a passion for how we can cure a disease, put a person on the moon, or launch a product that can make people happier and their everyday lives easier.

Risk-taking and innovation don’t just happen in a vacuum. Countries around the world have tried to emulate and replicate the start-up, Silicon Valley, bet-the-ranch entrepreneurialism for which we are known. Some are certainly making progress. Others have copied what they think is the formula — but none have achieved or surpassed us.

It has taken us generations of thinkers and doers to get to where we are today. And as much as I know it’s the spirit of risk-taking as the cornerstone of innovation, there are other key contributing factors that leaders, companies and organizations should hold fast to make sure we continue to take the big swings.

1. Promote a Culture of “Intraprenuership”

Some of the best ideas can be sparked from within an organization. Employees at too many companies are down in the weeds, caught up in their day-to-day. Great companies are those that foster a culture of internal entrepreneurship or, let’s make up a word, “intraprenuership.” These companies are places where employees are encouraged and expected to step forward with their ideas. It doesn’t happen on its own. Intrapraneurship needs to be clearly laid out in concept and principles within an organization’s mission, vision, and values. And it also doesn’t work without leadership support and a framework for it to take place. It can be encouraged by giving small teams autonomy to work on projects, by giving employees time to get away from the day-to-day through hackathons, and most of all by leaders having an open ear to new ideas.

Bill Gates, Steve Ballmer, and the early Microsoft leadership were huge supporters of intrapreneurship. The first company I founded, Expedia, started as an idea within Microsoft. When I pitched the idea to Bill, I first wanted him to fund it outside of Microsoft. He just laughed, and said, “Start it here. Let’s see what happens.”

2. Set BHAGs (Big Hairy Audacious Goals)

It is just as hard to build something small as it is to build something big. Encouraging employees to swing for the fences can have extremely valuable results. BHAGs are near-term goals that can be specific to each person’s job.

I’ve always set BHAGs for my team. One example is the goal I set out for Zillow’s first director of communications: attract one million users per month by month six, without a dollar of marketing spend. It seemed crazy when I proposed it, but she did it — and then some — we hit one million users in the first three days. In fact, our site crashed that first week because we had so many visitors. Earlier, when I launched Expedia, our BHAG was to become the largest seller of travel in the world — which is now true.

The goal should always be to achieve a BHAG, but the most important part of a BHAG is that the work to accomplish it keeps employees motivated and rowing in the same direction. But, much like Alexander Fleming didn’t set out to discover penicillin, even if BHAGs aren’t accomplished, the discoveries along the way can be invaluable.

3. Promote Big Ideas

Encourage big ideas and create an environment where failing to achieve them is ok. My first boss at Microsoft, Brad Chase, then Group Product Manager of MS-DOS, really drilled into me the idea that we should “take big swings.” When reviewing plans he always asked us, “What’s the really big idea?”

This approach led to some amazing stuff like the launch of the MS-DOS 5 upgrade, for which people camped on the sidewalk outside of Egghead Software in order to be first in line for the midnight sale. It also led to failures, like my ill-fated attempt to breed the software business with the book business. I tried to sell an “MS-DOS 6 Upgrade and DOS for Dummies” bundle at Barnes and Noble for $69.99. It failed fairly miserably and we were stuck with millions of dollars of inventory. Instead of firing me for my dumb idea — as might happen at many companies — Brad said, “Ok, that didn’t work out so well, but it was a big idea. What’s your next idea?”

4. Find Skilled Anglers

It may be scary for company leaders to risk their best talent on a risk-filled start-up within their own company, but that’s exactly what they should do. If Reed Hastings hadn’t stacked the talent deck on “House of Cards” when Netflix’s Chief Content Officer, Ted Sarandos, came to him and pitched the idea of original content, the company might be headed in a radically different direction today. For a crazy idea to succeed, it needs to have the best talent.

So how do we continue to foster and encourage up-and-coming and future inventors to take the big swings? Sure, it starts with not helicoptering over your children, and zipping your lip and crossing your fingers when your two-year-old decides to take on the big kids’ slide. It also means not punishing their failures, but encouraging their effort and ability to jump back at it and try again.

Another Brick in the Wall: Uber Surrenders to Didi in China

As an indirect investor (via Benchmark Capital and Coatue) in both Uber and Didi, it was hard for me not to be happy about the recent announcement that Uber has surrendered to Didi in China in exchange for an equity stake. The battle between Uber and Didi in China has burned billions of dollars and yuan, and investors on both sides were begging the companies to call a truce and stop losing several dollars per ride (over 10 million per day, reportedly) in their hunger for market share. The merger of Uber China with Didi should bring rational capitalism to the giant new Chinese ride-hailing industry, setting it and consumers up for a healthy future.

So, as an investor, I am happy — but as a free-trader and proponent of globalization, I am sad. I was listening to President Obama’s great speech this morning from Singapore in support of the TPP (Trans Pacific Partnership), of which China is not a party, and I was reminded once again of how closed the huge Chinese market is to non-Chinese companies. In industry after industry, countries outside of China have been ripped off or beaten back through a raft of Chinese protectionist regulations and traditions. Yet, Western markets are wide open to Chinese goods and services. It’s simply not fair.

I have some first-hand experience with this in my internet media and commerce businesses. In my interactions with Chinese internet entrepreneurs, I’ve found them to be smart, driven and creative. I also find they are happy to share their experiences and strategies with me and my American companies, which, at first, feels encouraging. Upon further reflection, however, this is probably because they have zero fear of my companies every coming into China and competing with them.

To be clear: I think Trump’s positions on international trade are naive at best and dangerous at worst. However, I do believe the U.S., along with China’s other trading partners, needs to push much harder on the Chinese government to open up their domestic markets to our companies and products. Uber’s capitulation in China is just another brick in the great wall that China has built around its economy to protect it from perceived foreign invaders.

I’ll be voting Yes on I-594. Background checks for gun ownership should be a no- brainer by now.

I will be voting “YES” on Initiative 594 November 4, and I hope you will join me.

yes594It is patently obvious that we should require background checks before a citizen is allowed to purchase a firearm. I am a gun owner and a lover of the outdoors myself, and I have personally donated to support the initiative. The Washington Alliance for Gun Responsibility (@Yeson594), a coalition of concerned citizens and organizations working together to stand up for common-sense solutions, has sponsored I-594.

This isn’t about the right to bear arms. It is a small but important step toward reducing gun violence by requiring background checks on people who buy guns, regardless of where they buy them. The vast majority of Washingtonians agree that background checks should include all firearm sales. Currently, this is not the case. Why our legislature has not yet passed legislation to reflect the will of the people is curious, and incredibly disappointing.

Zillow had a much-loved software engineer named Justin Ferrari get caught in a crossfire at the corner of Martin Luther King Boulevard and Cherry Avenue two years ago. He was driving his mini-van. His kids, who he’d just picked up from the community center pool, were in the car. So were his mom and dad. He died in his father’s lap. Gun violence is an epidemic, and I support making our citizenry safe in their own neighborhoods.

Thanks in large part to the honorable civic activism of Nick Hanauer (who has been instrumental in rallying people to support this initiative with votes and contributions), I-594 actually stands a chance of passing. But only if everyone else who supports responsible gun ownership gets out their vote.

I-594 is democracy at its best. It reflects the will of the people, makes common sense, and can save lives.

I hope my fellow citizens will join me in voting yes on I-594. Join the movement at

YouTube Preview Image

1 2 3 5