How to Be Just the Right Amount of Crazy in Business

Success in business--particularly in technology--relies on a balance between being calculated and being crazy. Here's how you can be both

Some of the most successful companies--especially in technology--were at one point just a crazy idea in the head of what some might consider a crazy founder. But those ideas became a reality because of many calculated moves. As a founder who was once called crazy (by my wife, no less), but approaches tasks with the calculated, in-the-weeds manner of engineer, I think the balance between the two is essential to success. Every crazy business decision has to be accompanied by calculated execution. Here's what I mean:

You have to be crazy enough to make a leap, and calculated enough to do it responsibly. Let's go back to my wife for a moment. When I quit my job at in 2009, my wife thought I was crazy. We were in the middle of an economic downturn and I was doing well as the head of engineering at a prominent public company. But I saw the opportunity to build something foundational and even if that meant working from our apartment in my sweatpants for a year and having some people call me crazy, I knew it would be worth it and I had a plan. I presented my wife with a PowerPoint addressing her concerns in a calculated way, showing her the massive opportunity and how I could take it on responsibly. I built a timeline, went through our finances and how we could allocate funds to take care of life's necessities while still pursuing my dream--I wanted to be clear that this decision wasn't a reckless one.

You have to imagine a market that doesn't exist, and then build it. I spoke at a conference last year, proclaiming that the best ideas are crazy, and usually are the most valuable in the long term. That's often because there's no market cap for a crazy idea because, at first, there's no market. There wasn't a market for SaaS when Salesforce first proclaimed "no software." There wasn't a market for car or apartment sharing before Uber and Airbnb. There wasn't a market for regular human space travel when Elon Musk founded SpaceX. (And maybe we're still in early days there.) But those founders foresaw massive opportunities driven by early trends, and then built products that shaped entire markets. They saw the forest for the trees and then cut them down.

You need to make tough decisions, and ensure they align with your vision. Sometimes you'll have to make unorthodox decisions. So, in a way, what might seem like a crazy decision is actually a very calculated move. Everyone thought Snapchat was crazy to turn down Facebook, but the company's seen massive success since then--largely because even a couple years ago CEO Evan Spiegel knew he had a captive audience that would one day (with the help of eager advertisers) make the company profitable. On the other side of the coin, many thought Instagram was crazy to sell to Facebook. But they've changed their tune and that's because, as Harry McCracken recently explained, Facebook gave Instagram access to tools--from Facebook's recruiting team to its spam-fighting technologies--that helped the company get where co-founders Kevin Systrom and Mike Krieger were planning to go anyway, only faster.

You have to tell an unbelievable story, then make that story a reality. Often successful companies tell their success story before it's a reality. Elon Musk did just that with Tesla, SpaceX and SolarCity--he talked about his companies' change-the-world technologies before they exist. Slack's story is one about the future of work when right now Slack is mainly used for simple office communication. And when Uber was first founded, riders could only summon black cars, but the company told a much bigger story about changing the way the world moves. That story captivated investors and now it's a reality. On the other hand, for a long time, Theranos' story enthralled journalists and consumers, and it fueled Theranos' momentum, but it might have been premature. A crazy, inspiring story can get you places, but you have to be calculated enough to make that story come true before others realize it's not.

Source: The opinions expressed here by columnists are their own, not those of

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