I just spent the past few days in San Francisco participating in some great dialog about venture capital, startups, future oriented technology and so forth. I spent time one on one and in a group setting with a billionaire, a number of very smart venture capitalists, entrepreneurs, amazing startup CEOs, etc. A strong group for sure.

Here’s the take-away: take more risk!

Yes, you have heard me say it before and will likely hear it again. Risk is not a bad thing. As a matter of fact it is “not” taking risk that is so scary.

Do you know who VC’s invest in? They back people who want to change the world, create new markets, disrupt the status quo, and solve major problems. Those activities are not done by conservative cubicle dwellers or latter climbers…

Wait, what if you agree, you take a bit of risk and uh oh, YOU FAIL… then what?

I’ll tell you… you are now MORE likely to raise a bigger venture round next time. You are more likely to get hired by another startup or see bigger career opportunities. Why, well, the answer is basically that those who take risks win. Smart people value the experience you have gained, the lessons learned and the fact that you were swinging for the fences on something that mattered. You stand out in a crowd.

My good friend (a successful entrepreneur turned talented VC) said it like this: “we want to back the guy who takes a big swing trying to do something amazing and fails… what we don’t want is the guy who builds a nice cash flowing small business and is happy with it… that isn’t interesting to us”.

So, gut-check… Are you taking enough risk?

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Yours in startups,


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