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The Changing Venture Landscape

Both Sides of the Table

In 2001 companies IPO’d very quickly if they were working, by 2011 IPOs had slowed down to the point that in 2013 Aileen Lee of Cowboy Ventures astutely called billion-dollar outcomes “unicorns.” Pre-seed is just a narrower segment where you might raise $1–3 million on a SAFE note and not give out any board seats.

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The Twenty Year Itch: My Last VC Investment Out of Brooklyn Bridge Ventures

This is going to be BIG.

To put that timeframe in perspective, here’s a picture of analyst me taken at USV’s first office in 2005, dressed in khakis and a button-down shirt versus a picture of me, a GP at my own firm, over 100 deals later, now on my latest Zoom board call from my couch at home with my junior analyst of about a year and a half.

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How to Manage a Startup Through Troubling Times

Entrepreneurs' Organization

Like the downturns in 2008 and 2001, this has been a very trying time for entrepreneurs running startups. Sometimes, you don’t feel comfortable describing your fears and frustrations to your cofounders or investors on your board, but a peer group allows you to do this in a safe way. This only makes the stress build up inside you.

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Reading what was written and the VC age question

This is going to be BIG.

When Chantel at chloe+isabel was getting offers from VCs, one of the things I said to her was to try and get as experienced a VC as possible--because she already had the younger product focused/community networked guy on her board. An experienced entrepreneur who has raised money multiple times can be a great board member as well.

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Praying to the God of Valuation

Both Sides of the Table

2001–2007: THE BUILDING YEARS The dot com bubble had burst. Within 5 years I was on the board of real businesses with meaningful revenue, strong balance sheets, no debt and on the path to a few interesting exits. Until we weren’t. Nobody cared about our valuations any more. Hey, we got to raise again next year. Let’s deploy faster!

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Want to Know How VC’s Calculate Valuation Differently from Founders?

Both Sides of the Table

Due to competitive markets we ended up with a pretty good term sheet until we needed to raise money in April 2001 and then we got completely screwed. After valuation in the video we went through Liquidation Preferences, Board Seats, Protective Provision, Voting Rights, Drag Along Rights, Redemption, Anti-Dilution and a few other key terms.

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Should Founders Be Allowed to Take Money off the Table?

Both Sides of the Table

In my first company I had to raise money in April 2001 or die. By then I was still on the board of my first company but it hadn’t yet sold (it ended up selling in 2007 to a publicly traded French company). And importantly you start thinking about your next gig. That’s when the VC has lost. Many term sheets ensued.

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