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

This is going to be BIG.

It will be the 105th deal out of Brooklyn Bridge Ventures, the firm I started back in September 2012, and it will be the last deal I’ll be making out of my third fund. It will also be my last venture capital deal. Around that time, I’ll be able to mark twenty years since I started as the first analyst at Union Square Ventures.

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Bad Notes on Venture Capital

Both Sides of the Table

On the phone … Me: So, you raised venture capital? I have never come across a sophisticated A, B or C round venture capitalist who thinks convertible notes are a smart move for entrepreneur or investor. Isn’t that conflicting advice? We raised a seed round. About $1 million. Me: At what price? Me: With a cap?

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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. Many entrepreneurs are reliant on outside funding, whether angel investors, venture capitalists or strategic investors , to keep the venture going. The pandemic of 2020 has tested most sectors of the economy.

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Making Sense of the Stock Market Drops in Relation to Venture Financing

Both Sides of the Table

I’ve seen friends (and family members) lose much of their savings that way over the years because “Black Swans” happen and in 1987, 2001, 2003 & 2008 (just to name a few from my memory) huge market gyrations caused much financial distress to people seeking short-term gains. You don’t have a clue. Neither do I.

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How Attractive is Risk Today?

Revolution

Great advice, but hard to do the “correct” thing when consumed by either of those emotions. Taking extra risk in the 2001–02 and 2008–09 time periods paid off. Not coincidentally, these are often the times that people feel more fearful and risk-averse. That discomfort is the point. The highest score ever was 97.6

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How Attractive is Risk Today?

Revolution

Great advice, but hard to do the “correct” thing when consumed by either of those emotions. Taking extra risk in the 2001–02 and 2008–09 time periods paid off. Not coincidentally, these are often the times that people feel more fearful and risk-averse. That discomfort is the point. The highest score ever was 97.6

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Venture Capital Q&A Session

Both Sides of the Table

We received so much positive feedback from our This Week in Venture Capital show walking through valuation calculations & term sheets that we decided to do a Q&A show this week to address topics that entrepreneurs want to learn about. In fact, far better if you haven’t raised venture capital. This is minutes 8-11.