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The Harder I Work, The Luckier I Get

Both Sides of the Table

years ago you’d remember RIP Good Times from Sequoia, which still strikes me as having been prudent advice in late 2008. Would Google have become today’s juggernaut without Yahoo! What if Google had paid attention to Dodgeball – would there be no FourSquare today? &#. I started by writing 3-4 times / week.

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Top Ten infoChachkie Entries Of 2011

InfoChachkie

I began publishing my blog in 2008. was published in 2009 and Time Wounds All Heels was written in 2008. Google likes these entries, as evidenced by the significant organic traffic it consistently drives to them. For instance, I was recently asked by Inc.com to write a weekly column. 2011 Rank. Do They Believe?

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Reflections on 2018: Richard Wolpert, The Soul Of A Deal

socalTECH

We do, as of the writing of this in early December, seem to be seeing a correction at this time. There is an all out ground war right now between Amazon and Google for control of voice in the home. I had expected a correction much earlier in the year and I was wrong.

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VC Confessions: We Passed On Twilio’s Seed Round

InfoChachkie

There were no unicorns in sight on April 14th, 2008 when Kevin O'Connor, my Partner Jim Andelman and I met Twilio's Founder and CEO, Jeff Lawson. A true Internet Pioneer, by 2008, Kevin had already founded or co-founded two Unicorns in his own right, DoubleClick (sold to Google $3.1 billion) and ISS (sold to IBM $1.3 billion).

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The Changing Structure of the VC Industry

Both Sides of the Table

We all have one-click purchase power (Apple, Google, Amazon, eBay). Just 3 years ago there was talk of institutional investors “not being able to write small enough checks.” Many pension funds are simply too large to write small checks and favor the ability to write $50-100 million checks to funds.

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What Angel Investing & Florida Condos Have in Common

Both Sides of the Table

And so it happened that between 2000-2008 I was the biggest buzz kill at dinner parties. Argument two says, “big companies can’t innovate anymore so Google, Apple, Microsoft, etc. Remember it was only 2008 where Microsoft and even Google were laying off employees. I will write about some of these topics soon.

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Angel Investing: Skill 3 – Relationships with VCs

Both Sides of the Table

In the latter cases many companies (Flickr, Delicious, Blogger, Writely in 05-08 and lately Invite Media, Aardvark, Dodgeball, etc.) My thesis on why this is happening is that large tech companies didn’t invest enough in R&D between 2008-2010 (Google even went through layoffs!!!)

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