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Why I Look for Obsessive and Competitive Founders

Both Sides of the Table

This blog started from a series of conversations I found myself having over and over again with founders and eventually decided I should just start writing them.It He wants to compete to be the lead drummer in the competitive ensemble and study under Terence, an obsessive instructor who is hell bent on winning competitions for the school.

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The Very First Startup Founder You Need to Invest in is You

Both Sides of the Table

This week I wrote about obsessive and competitive founders and how this forms the basis of what I look for when I invest. I had been thinking a lot about this recently because I’m often asked the question of “what I look for in an entrepreneur when I want to invest?” I had invested in myself for years.

Startup 409
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How I Invest

Both Sides of the Table

During the Q&A I was asked about how I make investment decisions in early-stage businesses. I answered in the same way I always do so I thought I’d just write it publicly. “I I know that sounds trite but it’s the best way I can describe my early-stage investments. If I don’t do both then it’s highly unlikely I will invest.

Invest 254
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Your Product Needs to be 10x Better than the Competition to Win. Here’s Why:

Both Sides of the Table

It was a pleasure to write them myself. Bill doesn’t think you should over invest in them but he does believe in protecting ideas when you have a true invention and many of his companies have done so. His impact has even helped a small country gain admission to the United Nations. Summary notes, as always, provide below.

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Why Venture Capital is So Much More Compelling Now

Both Sides of the Table

It’s not hard to find people willing to write the narrative that “venture capital is not an asset class” or “venture capital has performed terribly.” I hope to publish that deck and a full write up in the next 10 days in partnership with Dan Primack at Fortune (if my write up doesn’t suck, I guess ;-)).

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The Changing Venture Landscape

Both Sides of the Table

I’m over-paying for every check I write into the VC ecosystem and valuations are being pushed up to absurd levels and many of these valuations and companies won’t hold in the long term. On the one hand, you’re over paying for every investment and valuations aren’t rational. That used to be called A-round investing. of the fund.

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What Does the Post Crash VC Market Look Like?

Both Sides of the Table

Even then private market investors can paper over valuation changes by investing at the same price but with more structure so it’s hard to understand the “headline valuation.” No blog post about how Tiger is crushing everybody because it’s deploying all its capital in 1-year while “suckers” are investing over 3-years can change this reality.