Why Jason Calacanis channels ‘Indiana Jones or James Bond’ as an investor and entrepreneur

Photo via: https://www.facebook.com/jasoncalacanis/

Jason Calacanis is an investor, entrepreneur and thought leader — but he also likes to think like an action movie star.

Wilson Sonsini Goodrich & Rosati recently interviewed Calacanis as part of their Q3 2015 Entrepreneurs Report. Here’s an excerpt:

What’s your view of the overall state of the broader venture market beyond just seed-stage capital?

There’s never been this many companies executing at such a high level, which is leading to a lot of good, deserving companies not getting funded. There are companies not getting funded today that five years ago would have had no problem closing an A round or even a B round. The goal posts have moved. We’re no longer playing a hundred-yard game — it’s a thousand-yard game.

The stakes have gone up, but the number of investors and VCs is not growing as fast as the number of companies. At the same time, you have this new class of super angels, like me, who are helping. Then you’re seeing a lot of this seed, seed-plus, seed-plus-plus. And I’m advising a lot of people, saying, “Hey, imagine a world where you can’t get an A, but you do have $1 million in revenue. What does that look like? How do you get alternate sources of funding?”

From my 20 years of experience as an entrepreneur, I always like to have multiple strategies for getting out alive. I look at it like Indiana Jones or James Bond. You’re in the middle of the evil lair and you should have more than one exit possibility, because when the shit hits the fan — which it inevitably does — you want to have options.

A lot of entrepreneurs don’t think that way. They just think, “I’ll go back to my existing investors, where Sequoia’s going to give me my A round and Andreessen’s going to give me my A round.” That’s just not realistic anymore. You have to have that A-plus round or that C-plus round. You have to be able to go to those existing investors and ask, “Hey, what do I need to prove to get you to match what you previously put in?”

That’s why I’m only investing in people who agree to do a monthly update. Not because I’m a control freak, but because if you’re updating investors monthly, the chances of them investing in you again when you do hit inevitable roadblocks go up exponentially. You have a 10 times better chance if you’ve kept people informed. If you haven’t, and the next time they hear from you is when you’re out of money, that’s not going to go well for you.

I have frank discussions where I say, “Are you okay with sending me an update every month where the first line is how much cash you have, how much you’re burning, and how many months are left? Are you okay with sending me a revenue chart, or monthly active use charts, even if it’s bad?” Just be candid and honest.



December 2, 2015