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10 Key Steps For Aspiring Billionaire Entrepreneurs

Startup Professionals Musings

Everyone recognizes a great entrepreneur when they work with one, but most entrepreneurs don’t know what to look for in themselves that will drive that perception by others. The points are great, but can be made even simpler and more actionable by adapting then to the world of the entrepreneur: Demonstrate character.

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Top Ten infoChachkie Entries Of 2011

InfoChachkie

I began publishing my blog in 2008. By early 2010, I found my stylistic voice and identified my audience of emerging entrepreneurs and thus dropped my penname. was published in 2009 and Time Wounds All Heels was written in 2008. For instance, I was recently asked by Inc.com to write a weekly column. 2011 Rank.

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

socalTECH

Editor's note: As we head into the new year, we've been featuring reflections on 2018 from notable investors, entrepreneurs, and others from Southern California's technology community. We do, as of the writing of this in early December, seem to be seeing a correction at this time.

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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.

Startup 391
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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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As Populist as it May Feel, 98% of VCs Aren’t Dumb

Both Sides of the Table

After all, I am no stranger to the publicly expressing the frustrations of dealing with the downside of this industry as I wrote about in 2006 when I was an entrepreneur. In the original version of his post, Andy writes. 2008 App ecosystem on iOS = $0. The best VCs don’t try to help entrepreneurs.

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Angel Investing: Skill 3 – Relationships with VCs

Both Sides of the Table

This is the third article in a series on what it takes to be a great angel investor (and why this should matter to entrepreneurs). I should say that I agree that naive optimism in entrepreneurs can produce higher beta (upside or flops) and that’s good from an investment standpoint if you’re looking for big returns.

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