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What Did I Learn From the First VC Check I Ever Wrote?

Both Sides of the Table

I became a VC 12 years ago in 2007 when the pace of deals was much slower. As I was trying to figure out the role I wanted to play in the VC world I decided I wanted to focus on businesses that were building deeply technical products to solve problems for business users. Over the past 2.5 Why does that matter? But here’s the big “aha.”

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How Many Investors Should You Talk to in a VC Fund Raise? And How Do You Prioritize?

Both Sides of the Table

The typical VC process is as follows: They say there are three rules in property: Location, location, location. The surest sign a fund-raising process has stalled is when you aren’t getting follow-up meetings or hearing from the VC or hearing from friends that they got a phone call or email asking about you. Same with VC.

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What I Would Look for When Choosing a VC – Knowing What I Know Now?

Both Sides of the Table

Picking a VC is hard. So I thought I’d write about out with what I would look for in a VC knowing what I know now and why. Most VCs are book smart. VCs should be more of a coach than proscriptively telling you what to do. You want a VC who will spar with you but then STFU and let you get on with things.

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This Week in Venture Capital – Episode 2

Both Sides of the Table

I was on This Week in Venture Capital (TWiVC) again this week with Jason Calacanis. You can watch this week’s TWiVC episode by clicking on the link and my summary notes are below. {if Bill Gross is the man responsible for the overwhelming amount of monetization on the web. In my mind, not a typical VC investment.

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This Week in VC with Jim Armstrong of Clearstone

Both Sides of the Table

Had a great chat with Jim Armstrong who is a General Partner at Clearstone Venture Partners today on TWiVC. It was especially fun for me because we got the chance to talk about the VC industry and how entrepreneurs should think about the VC industry in addition to discussing deals. Some summary notes are below.

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Why you should never have a data room — the most counter-intuitive fund-raising advice you’ll ever…

Both Sides of the Table

Or if you’re a VC raising from LPs you have to list all of your deals, your investment value, your carrying value, your multiples, your IRRs, TVPIs, DPIs, etc along with net cashflows plus your previous LPAs. So what does a VC do when he or she isn’t ready to say “no” or perhaps might like to talk with you in a year but not now?

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Turning the Camera on Chris Dixon

Both Sides of the Table

He and I once took different sides of an debate about whether “VC signaling&# in early-stage deals is a serious problem or not. Chris runs a popular web interview series on TechCrunch so is used to being the guy asking the questions. I’ve also found him to not be dogmatic either.