After the acquisitions of both ExitEvent and Automated Insights over the last couple years, my life has taken a few strange turns. Nothing earth-shattering and nothing I wasn’t prepared for; Inbox fills up pretty quickly, lots more unsolicited contact, more people know how to pronounce my name.

That last one is nice, but it’s always been pretty simple. Pro Tip: All the Os are long.

One recent turn that sort of threw me for a loop was when I sat down last week for an hour-long interview about my investment strategy.

Because I’ve never really thought about it.

Well, let me walk that back a bit. I’m not new to investing. I’ve been investing in my own endeavors since college, and in other companies for the last 10 or 12 years. There’s just a lot more inbound now. And with inbound comes questions. My answers to these questions usually raise eyebrows, not because they’re necessarily contrarian or zany, but because they’re honest. And maybe because I always feel like I get asked the wrong questions when it comes to investment strategy.

Q: “How did you get started investing?”

A: “A rock band.”

So yeah, that just sounds stupid. But I’ve touched on this before. Forming a rock band is a very good startup learning experience. You put together a diversely-talented founding team, you spend a ton of time perfecting a product, and then when you’re ready, you throw dollars on top of time and make a run at it. I did that sophomore year. Twice.

Towards the end of my college career, I started to apply the same concepts to other pursuits that were a little more based in reality. After college, I founded and funded two companies that went nowhere. Then I joined my first actual startup and got an idea of what the process actually looked like.

Total A-ha moment.

Read the rest at:

http://exitevent.com/article/why-i-suck-at-investing-160414

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